Random futa things

by Jokiba

Just as the title says pure smut

18. Collared mom

Stories of a Collared Mom ChroniclerInTheDark (Fsyco)

Summary:

A collection of short stories about Naomi, a collared mom who will do anything her children ask of her.

Notes:

I tried something new for this one, let me know how you like it. I plan to write all future entries in this style, since it was fun and I think it works well.

(See the end of the work for more notes.)

Chapter 1: Naomi's Typical Saturday

Summary:

Naomi chats with a friend about her weekend, but is interrupted by a visit from her sons.

Notes:

Update: I went through and made some improvements after talking with my partner.

Chapter Text

Naomi sits down to her computer in the family's living room with a sigh. In spite of how busy she's been, she has a smile on her face. A glass of ice water sits on her desk, covered in a layer of condensation. She starts up her favorite chat client, and gets a message from a friend as soon as she logs in.

Session Start

[14:00] TheFool Hey there, Naomi!

[14:01] CollaredMom Hello, Terry :) How are you?

[14:01] TheFool Good, how are you? No party at Megan's this weekend?

[14:02] CollaredMom I'm well :) Sadly, no, haha.

[14:02] TheFool Next weekend, then?

[14:02] CollaredMom Hopefully :)

[14:04] TheFool Do anything exciting today? How are the kids?

[14:04] CollaredMom Nothing in particular, haha.

[14:05] CollaredMom They're well :)

[14:06] TheFool Emily still wearing her collar?

[14:07] CollaredMom She is!

[14:08] CollaredMom She almost never takes it off anymore except to go to school, haha

[14:08] TheFool Wow

[14:09] TheFool And she still has to follow the same rules you do while it's on?

[14:11] CollaredMom Correct :) No clothes in the house unless otherwise ordered, and must comply with any and all requests made of her, no matter what, when or wherever it is made of her.

[14:11] CollaredMom Although, unlike me, she can take hers off whenever she likes, haha

[14:11] TheFool Bet the boys are keeping her busy

[14:11] CollaredMom Nothing she can't handle ;)

[14:12] CollaredMom Actually, I admit it is nice having someone to share the load with, so to speak

[14:12] TheFool I think you mean share the loads, plural

[14:13] CollaredMom Well, yes, that too ;) haha

[14:13] TheFool Speaking of, how many loads have you both had today?

[14:14] CollaredMom I've had 3, I believe she's had 4 :)

[14:15] CollaredMom We each had two this morning. Master and the boys wanted blowjobs while they had breakfast, you see ;)

[14:15] TheFool Wow. Was that what you two had for breakfast?

[14:16] CollaredMom Haha, we had real food. After we finished sucking cock. ;)

[14:16] TheFool What about the other loads?

[14:18] CollaredMom My third one wasn't terribly exciting. I bumped into Jake while I was cleaning his room, so he ordered me onto his bed and fucked me doggystyle :) Then he went back to playing video games.

[14:19] TheFool That sounds pretty exciting to me

[14:19] TheFool How about Em's?

[14:20] CollaredMom I went to the kitchen for a drink and saw that Jason had bent her over a counter, haha. She claims she was 'ambushed'

[14:21] CollaredMom Jake was hanging around and said he wanted a turn with her, which is why I believe she's had 4

[14:21] CollaredMom I suppose I could ask her if you like, haha :)

[14:21] TheFool Sure, if she doesn't mind

[14:22] CollaredMom One moment, then :)

[14:27] CollaredMom I'm back :) The kids all say hello, haha

[14:27] TheFool Welcome back!

[14:27] TheFool Hi, kids

[14:28] CollaredMom She confirmed that 4 is correct :)

[14:28] TheFool Busy girl

[14:29] CollaredMom My sons, however, think our numbers are a little low, unfortunately. :(

[14:29] TheFool Oh no!

[14:30] TheFool Are they going to run away from home? I know I would if I were that ashamed of my parents

[14:30] CollaredMom Haha, no, nothing so drastic :)

[14:31] CollaredMom I'll turn the webcam on ;)

A video feed goes live, showing a nude, middle-aged woman seated at a desk. She has pale skin, large breasts, and is a little chubby. She has shoulder-length brown hair, green eyes, a chain connecting the rings in her pierced nipples, black nail polish, and a black leather collar. Her four children stand behind her, smiling and waving to the camera. Their voices are audible as they say "Hi!"

Her three sons are fully clothed. Her daughter, with longer hair, more petite build, and smaller bust size, is also nude save for a black leather collar identical to her mother's.

[14:31] TheFool Hey there, everyone!

Emily: Hi, Terry!

Naomi: They were excited when I mentioned that you were online.

[14:32] TheFool I had no idea I was so famous

Jake: How are you doing?

[14:32] TheFool I'm okay

[14:32] TheFool You?

Jake: I'm okay too, about to get way better, though!

[14:33] TheFool Yeah, I can see that

[14:33] TheFool Your day seems to be going a whole lot better than mine

Jason: Hey Mom, get up. Jake, when you're done bragging, can you make sure the webcam has a good view?

Naomi: Of course, dear.

Jake: Heck yeah!

Naomi stands up from her chair. Jake, her youngest son, moves the chair and adjusts the webcam so it has a better view of the floor. Jason and Jeremy, Naomi's oldest and middle sons, respectively, start taking off their clothes.

Jason: Mom, get on the floor, doggystyle. Make sure the camera can see everything, cause I feel like showing off! [He grins and does finger guns to the webcam, then immediately starts laughing]

Naomi: As you command.

Naomi drops down to the floor and gets on her hands and knees. She is in profile, so the webcam can see her from the side. The chain linking her nipple piercings dangles against the floor.

[14:35] TheFool Looking good, Naomi!

Jeremy: Em, get on your knees next to mom.

Emily: Fine. [She sounds mildly annoyed]

Emily kneels down next to Naomi. She appears behind her mother on the webcam. She's facing the same direction as Naomi, but her head appears some distance above her mom.

Jason: How's it looking for you, Terry?

[14:37] TheFool Looks really good to me!

Jason checks the text feed and gives the camera a thumbs up.

Jeremy wordlessly gets behind Naomi, grabs her hips, and thrusts inside her. At the same time, Jason moves in front of her, and she starts to suck his cock. Naomi moans loudly, but is muffled by the dick in her mouth.

Jake approaches the kneeling Emily, who is waiting with an open mouth, grabs her by the back of the head, and starts to fuck her face. She looks surprised at first, but quickly seems to adjust. She looks up at her brother, and does nothing to resist him.

[14:39] TheFool Go go go! Give it to 'em!

The audio feed picks up the wet slapping of Jeremy fucking his mom, and the 'glug-glug-glug' noise Emily makes as her face is fucked. Occasionally, a sharp smack rings out, either from Jeremy spanking Naomi, or from Jason slapping Naomi across the face. Both leave red marks visible on the camera feed. There is also the regular sound of gasping as Emily is given a break for air. Light glistening off her saliva is visible in the video feed, which has coated her brother's cock and dripped onto her chest.

[14:42] TheFool *My* mom would kill me if I smacked her like that

After going at this for some time, Jake is the first to cum. He thrusts deep into Emily's mouth as he cums, audibly grunting and groaning as he pulses and throbs inside her tight throat, shooting his jizz directly into her stomach. His cock is still twitching when he pulls it out, and Emily starts coughing violently.

[14:49] TheFool You okay there, Emily?

Emily: I'm good! [She coughs again] I'm good! [In spite of her coughing, she looks satisfied, and gives a thumbs up to the cam era]

[14:49] TheFool You had me worried there for a minute!

Jeremy is next to cum. He thrusts into Naomi as deep as he can as he unloads his seed. He lets out an audible "Fuuuuck yeeeaah" as he cums. Naomi makes a satisfied moaning noise as she feels a spreading, sticky warmth deep inside her. He pulls out, and drops of semen can be seen falling out of her shortly afterwards.

Jason is the last to cum. He pulls out of Naomi's mouth and jerks himself off. White streams of cum can be seen splattering Naomi's face.

Jason: That was awesome! Mom, show Terry your facial!

Naomi: Yes, dear.

Naomi turns her head and scoots closer towards the camera. Her face is covered in thick, white ropes. Her left eye is closed, and a stand of cum lays across her eyelid. It feels warm and sticky, and Naomi can feel it rolling all down her face.

[14:51] TheFool Damn, that's a really good cumshot

Naomi turns to her eldest son.

Naomi: May I clean up, young master?

Jason: Hrm. Not yet. [He grabs his phone from somewhere off screen and snaps a picture of Naomi's face]. Okay, now you can clean it. After you're done talking to Terry.

The three brothers lean awkwardly into frame and wave while saying "goodbye". They then leave the camera's field of view.

Naomi: Just as well, the laundry won't do itself. It was lovely seeing you! Take care!

[14:53] TheFool You too! TTYL

Session Close

Chapter 2: Naomi Goes Partying

Summary:

After an eventful weekend, Naomi recounts a party she and her family attended.

Chapter Text

Session Start

[19:00] CollaredMom Good Evening :)

[19:02] TheFool Hey you!

[19:02] TheFool How's you?

[19:03] CollaredMom I'm well, and yourself?

[19:03] TheFool I'm alright

[19:04] TheFool How was your weekend?

[19:04] TheFool Party at Megan's this weekend, right?

[19:05] CollaredMom So you remembered ;) Can't imagine why, haha

[19:06] CollaredMom But yes, that's correct. Another usual Megan shindig :) Very fun, although we're all still a little tired from it, haha

[19:06] TheFool And sore?

[19:07] CollaredMom Well, yes, that too ;) Nothing I can't handle, though, haha

[19:07] CollaredMom Don't know how Megan handles it all the time…

[19:08] TheFool So when did you go? What happened when you got there?

[19:09] CollaredMom We arrived around 6 in the evening :) A few of my sons' friends managed to come along! They were very excited, as you can imagine ;)

[19:11] CollaredMom We were a little early, haha, so it wasn't *wildly* exciting when we got there. Everyone there was saving themselves for the main event :) Us included, of course

[19:12] CollaredMom Of course, Emily and I stripped down to just our collars and had our leashes attached as soon as we stepped inside ;)

[19:12] TheFool I don't know if I could hold out for that long

[19:13] CollaredMom Haha, well, you wouldn't want to embarrass yourself once the main festivities start, would you?

[19:14] TheFool Point taken

[19:15] TheFool So, what, you just hung out and made small talk while waiting for people to show up?

[19:15] CollaredMom Essentially :)

[19:16] CollaredMom We stayed with my sons, naturally, since they were holding onto our leashes, haha

[19:16] TheFool Makes sense

[19:17] TheFool How long were you waiting? Megan usually starts at… 7 if memory serves?

[19:17] CollaredMom I'm surprised you remember! Yes, it was around an hour before things kicked off

[19:18] CollaredMom Once there were enough people, we all gathered in Megan's living room. She'd made quite a bit of space for everyone, haha. She gave a little speech to kick things off, so to speak, and then the boys were upon us :)

[19:19] TheFool How many people were there?

[19:19] CollaredMom 7 sluts, around 20-30 boys, including us. My estimation might be off, though, haha. I'm dreadful with numbers.

[19:20] CollaredMom I had 3 on me right at the start, haha. Went for all my holes at once. It was… rather intense ;)

[19:20] TheFool I bet

[19:21] CollaredMom Master actually got some footage, haha. He's working on splicing it all together into a good video, but I *do* have some highlight reels I've been instructed to share ;)

[19:21] TheFool Ooo! I'm very excited!

[19:21] -CollaredMom- Sent 4

The video starts with Naomi sitting on a couch. She is nude, save for her black leather collar. Her son Jeremy sits next to her, holding onto her leash and talking to someone else just out of shot.

Frank [from behind the camera]: Are you ready for tonight?

Naomi: I'm always ready, Master. [She gives a little smile to the camera]

The video suddenly cuts to Naomi being triple penetrated, her holes filled by boys who look like they're in middle school. She's on her hands and knees; one boy is beneath her, one is behind her, one is in front of her. The boys are rough and aggressive with all her holes, and Naomi lets out muffled moans. The boy fucking her ass gives her leash a hard tug. Naomi's breathing becomes notably more strained as she's choked, but she does not struggle or ask him to stop.

The video cuts to a brief shot from behind of Naomi's holes, showing cum dripping out of them.

The video cuts again, this time showing Naomi getting fucked in the ass from behind, letting out choked moans as the boy fucking her tugs hard on her leash.

The video cuts a final time, this time showing Naomi giving a boy a titfuck. Her large breasts are pressed together, giving the chain between her nipples a lot of slack. They're soft and glistening with lubricant. Suddenly, he cums, spraying Naomi's neck and chest with his seed. He pulls away, and his cum starts to dribble down to her tits.

[19:27] TheFool Damn! That was really good! Those boys were rough with you! You alright?

[19:28] CollaredMom I'm fine, haha :) I actually rather enjoy being choked, I'll have you know. It gives me an exhilarating sense of powerlessness, and really puts me in my place ;)

[19:29] CollaredMom It also helps whoever's fucking me feel powerful, which means they fuck me better. :)

[19:31] TheFool The boys have fun, too?

[19:31] CollaredMom Naturally ;)

[19:32] -CollaredMom- Sent 4

[19:32] TheFool I love that file name, lol

[19:33] CollaredMom Master named it, haha

The video opens with Jake, Naomi's youngest, and another boy fucking Megan, the party's hostess. Megan is a tall woman in her late 40s or early 50s with dirty blonde hair, wearing black nylon stockings and a pair of black open-toe heels. Jake is going to town on her asshole while the other boy fucks her pussy. Megan moans and screams loudly, although her face is not visible. Jake looks at the camera and pumps his fist.

The video cuts to show Jeremy, Naomi's middle son, with Megan's daughter, Juli. Juli is a petite, busty girl in her early 20s with platinum blonde hair, wearing a fishnet body stocking. Jeremy is roughly fucking her face. Juli lets out loud "glug glug glug" noises as her face is fucked, and saliva is dripping down both his cock and her chin. From the calm look on her face and the buildup of her spit, it seems she's been at this a while. Jeremy briefly pulls out of her mouth to give her air, and Juli smiles up at him.

The video cuts again to show Jason, Naomi's oldest, receiving a footjob from Tanya, Megan's wife. Tanya is a curvy black woman in her mid-40s with black hair, wearing only an anklet and a few toe rings. Her nails are painted purple, and she skillfully rubs Jason's cock with her toes, using her big toes to stimulate his sensitive head. Shortly after the scene starts, Jason climaxes, adding an extra white coat to Tanya's purple nail polish as he oozes cum onto them.

[19:37] TheFool I'm jealous of your boys

[19:38] TheFool Does Emily have a highlight reel, too?

[19:38] CollaredMom Master is working on it, haha

[19:39] CollaredMom I'll be sure to send you the full video whenever he's done with it ;)

[19:39] TheFool Looking forward to it

[19:41] TheFool Sadly, I should be logging off soon so I can get ready for bed. I got w*rk tomorrow morning and it's late here

[19:41] CollaredMom Aw :( Well, it was lovely seeing you :) Take care!

[19:41] TheFool You too!

Session Close

Chapter 3: Consolation Prizes

Summary:

As Naomi and Emily return from a party, they stop by a friend's house to drop him off. However, they find some boys who were unable to attend inside.

Chapter Text

Session Start

[13:00] TheFool Hey hey!

[13:00] CollaredMom Good Afternoon :)

[13:01] TheFool How you doing?

[13:02] CollaredMom I'm doing well, and yourself?

[13:03] TheFool I'm okay. Pretending to work right now

[13:03] CollaredMom Oh no :(

[13:04] CollaredMom I'm home alone at present. Waiting for the laundry to finish :)

[13:05] TheFool The kids at school?

[13:05] CollaredMom Correct :)

[13:06] TheFool How selfish of them

[13:06] CollaredMom Quite, haha

[13:07] CollaredMom Alas, if only they could stay home and fuck Mommy all day ;)

[13:08] TheFool You need to petition your congressman so we can have a law letting them skip school to take care of you

[13:09] CollaredMom I suspect it'd end up more with me taking care of them, haha ;)

[13:10] TheFool It's a sure winner! What politician *wouldn't* want to champion families supporting each other?

[13:11] CollaredMom I'm not sure that would work, haha. Something tells me people might take issue with that sort of thing

[13:12] TheFool I can't think of a bigger family value than incest, tbh

[13:12] CollaredMom Your logic is ironclad ;)

[13:13] TheFool Maybe *I* should go into politics

[13:14] TheFool "A collared mom in every home!"

[13:14] CollaredMom Ha!

[13:15] CollaredMom Well, you have *my* vote :)

[13:16] TheFool I appreciate it. With your vote, we'll make America a better place

[13:19] CollaredMom So, not to swerve entirely away from your burgeoning political career, but I had something you might find interesting :)

[13:20] TheFool Please, I'm sure your thing is way better than mine

[13:20] CollaredMom Can you watch videos?

[13:21] TheFool Yeah, that's fine

[13:21] CollaredMom Excellent :)

[13:22] CollaredMom I mentioned the party we went to the last time we spoke, I believe

[13:22] TheFool You did!

[13:23] CollaredMom Well, we brought a few of my sons' friends, including a boy named Rag. Unfortunately, not all of their friends could come along with us to Megan's place.

[13:24] TheFool ...his parents really named him 'Rag'?

[13:25] CollaredMom It's a nickname, haha. His family is Indian, his full name is quite a mouthful for most of us

[13:25] TheFool OH

[13:25] TheFool Okay that makes more sense

[13:26] CollaredMom Anyway, we went to go drop him off on our way back, but Master told Emily and I to go inside with him for a little bit

[13:27] TheFool This seems like a common setup for you two

[13:28] CollaredMom Indeed, haha. I'm rather good at catching onto when something is up these days. Not that it makes it any less fun. ;)

[13:29] CollaredMom So we follow him inside, and we're met with 4 of the boys who couldn't come along to our party :) They seemed rather eager to see us

[13:30] TheFool Take it they didn't just want to have a chat over tea?

[13:30] CollaredMom Haha, well, see for yourself ;)

[13:31] -CollaredMom- Sent 4

The video shows a large front door with opaque glass panels on either side. A group of four boys hangs around by the door. The door suddenly opens, and Rag, a boy of Indian descent, walks inside, followed by Naomi and Emily. Naomi is wearing a sundress, Emily is wearing a blouse and a miniskirt. Both have on matching black leather collars.

Naomi: Oh my. Hello, boys.

Emily: I knew it.

Without saying a word, two boys approach Naomi and Emily. They take each girl to either side of the front door and turn them around. Naomi and Emily press themselves against the opaque glass. Naomi's dress and Emily's skirt are both hiked up, and the two boys start to fuck them. Rag joins the other two boys and watches.

Boy 1: [While fucking Naomi] Hey, Mrs. S.

Naomi: [While moaning] Happy to -ah!- see us?

Boy 1: Happy to see this pussy

Emily: [While moaning] Sorry you -ah!- couldn't come with

Boy 2: [While fucking Emily] At least we can cum now! [Emily groans at his joke]

Footsteps are heard from off screen as Sai, Rag's mom, approaches.

Sai: [From off-screen] Rag, are you home?

Rag: Yes, mom.

Sai enters the camera's field of view. She's a beautiful Indian woman in her 40s, wearing a blouse, a pair of jeans, and flats. She speaks with a notable accent.

Sai: Are you having fun ambushing Naomi?

Boy 1: Yeah!

The boy fucking Naomi gives her butt a hard spank, creating a loud, sharp noise. Naomi lets out a yelp in response. Sai walks up between Naomi and Emily.

Sai: Nice to see you Naomi, Emily.

Naomi: Nice to -ah!- see you too, Sai!

Emily: Heya-ah!-, Mrs. A!

Sai: Honestly, I don't know how you two put up with this.

Naomi: You -ah!- get used to it.

Emily: It's -ah!- not so-

Emily is interrupted as the boy inside her cums. He thrusts deep into her, pumping her full of his seed, then pulls out. Emily's hole is only unoccupied for less than a minute, though, as another boy approaches and starts fucking her.

Sai: Well, as long as you're having fun. [She looks over and sees the camera, then turns to Rag] You could at least make yourself useful and help with the camera stuff.

Rag: It's fine, the camera has a good view of everything.

Sai: Look, it's static! You're only getting one angle! You should at least do a second angle! Who taught you boys how to record a sex tape?

As Sai and Rag bicker, the boy fucking Naomi cums as well, and is replaced by the other boy who was waiting as soon as he's finished with his turn.

Sai: Here, you should get some closeups.

Sai walks over behind the camera and picks it up. The camera moves closer between Emily and Naomi, showing closeup side-on views. The camera then shows a closeup of Naomi's holes. Cum drips out of her gaping pussy as her asshole gets pounded roughly. The camera then moves over to Emily, showing a cock making a cummy mess of her pussy as it slams into her.

Sai: See, that's a much better shot.

Rag: If you say so, Mom.

Sai: You boys should try pulling out and doing a cumshot to finish, that will look much better on camera.

Boy 4: [While fucking Naomi] I wanna cum on her face!

Naomi: As you -ah!- wish.

After a few minutes of the two of them getting fucked, the boy fucking Emily announces he's going to cum. Sai brings the camera over to show him pull out of Emily and stroke his cock. He sprays cum all over Emily's ass, and it starts to drip down her skin. After he's done, he pulls her skirt back down, and it sticks to some of the semen on her butt.

Emily: I can't wait to get home and clean that up.

A few moments later, the boy fucking Naomi says he's close. He pulls out of her, and Naomi dutifully turns around and kneels before him. Naomi closes her eyes, and cum sprays all over her face.

Sai: That looks pretty good. You were really pent up.

Naomi: Thank you, sir. Sai, be sure to send us a copy, won't you?

Sai: Of course.

[13:52] TheFool Damn, that was hot

[13:52] TheFool Those boys didn't even say hello to you

[13:53] CollaredMom They don't invite me over for my conversational skills ;)

[13:54] TheFool That's a little sad, you're fun to talk to

[13:54] CollaredMom Thank you, haha

[13:55] CollaredMom We were sent in as 'consolation prizes', you see, since they couldn't come to the party :)

[13:55] CollaredMom Master and Sai worked together to organize it. They thought it was unfair that everyone couldn't attend.

[13:56] TheFool I'm surprised his mom was cool with that

[13:57] CollaredMom Sai is a very interesting woman, haha

[13:57] TheFool Does she play with any of you at all?

[13:58] CollaredMom Alas, she does not

[13:58] CollaredMom Maybe one day :)

[13:59] CollaredMom My laundry is nearly done, I should be off. Do take care :)

[14:00] TheFool You too, take care!

Session Close

Chapter 4: Naomi Gets Bred By Her Brood

Summary:

Naomi's boys make a mommy of her again as they try to expand the family by using their mother for breeding.

Notes:

(See the end of the chapter for notes.)

Chapter Text

Session Start

[21:00] CollaredMom Good Evening, Terry :)

[21:01] TheFool Hey you! How are you, Naomi?

[21:02] CollaredMom Quite well :) rather excited, I must admit

[21:02] TheFool Oh? If something has you excited, it must be good

[21:04] CollaredMom Well, I don't know if you remember, but Master talked about having our sons breed me at least once. He said he wanted to start after getting a vasectomy, if you'll recall.

[21:05] CollaredMom So, he's had it today :) I'm also officially off my birth control as of today, as well!

[21:05] TheFool Wow, that's some dedication!

[21:06] CollaredMom Thank you :)

[21:06] TheFool I'm impressed you're going through with it

[21:07] TheFool So how does this work, exactly? Are you still going to go to Megan's parties? Are the boys' friends still allowed to come over?

[21:08] CollaredMom It's not terribly complicated, really. The boys will mostly just be fucking my pussy :) and maybe thinking fertile thoughts, haha

[21:10] CollaredMom Friends are still allowed over, but they have to use a condom until I'm confirmed pregnant. There's a few weeks until Megan's next party, and if it hasn't taken by then… well, we'll figure something out :)

[21:11] TheFool Good for them, although I might be a little miffed if I had to use a rubber all the time

[21:11] TheFool Well, good luck! I hope it goes well for you!

[21:12] CollaredMom Thank you :)

[21:12] TheFool How about Emily, is she doing this too?

[21:13] CollaredMom Not at present

[21:14] CollaredMom She hasn't expressed any interest in it. Just as well, she'll be handling some of my duties while I'm indisposed, haha.

[21:15] TheFool Oh yeah, I imagine it would be hard if both of you were out at the same time

[21:16] CollaredMom Precisely, haha :)

[21:18] TheFool Well, I'm very happy for you! Sadly, I gotta get going, you actually caught me a little bit before I was gonna head off. Good luck and keep me updated!

[21:19] CollaredMom Good night :)

Session Close

It was a particularly lazy Sunday, and Naomi was in the laundry room showing Emily how to fold and put away clothes, as well as the specific settings best suited for each load of clothing. Somewhat ironically, they were both nude. Emily opted to wear her collar, and as such wasn't permitted to wear other clothes. Naomi had much less of a choice in the matter.

"I thought this would be harder." Emily remarked as she watched her mother work.

"It's really not that difficult." Naomi agreed. "It just takes a little care and-"

"Hey, Mom!" Jake called out as he entered the room, carrying a leash. "Whatcha doin'?"

"Emily, can you be a dear and finish folding these?" Naomi asked. "Don't forget to move along the next batch, too.

"Sure thing." Emily answered.

"Thank you, dear." Naomi said, before turning to face Jake. "Am I getting bred by one of my wonderful, handsome sons?"

"Nah, you're getting bred by the loser one." Jake replied. Emily stifled a laugh at his dumb joke. Naomi let out an amused sigh as she leaned down so that he could attach the leash to her collar. "Hey, Em, can you go get Jer and Jason?"

"Sure thing." Emily answered, and hastily left the room.

"How would you like to take me, then?" Naomi asked.

"Let's see…" Jake said as he looked around the room. He spotted a table against the wall, which had a few cleaning products scattered on the top. Jake led his mother to the table and bent her over it. Her fat, curvy ass was now right in front of him. Jake quickly unzipped his pants and let them fall to his ankles. He was already rock-hard, and he knew his mom would be ready to receive him. Naomi never needed any prep; she was always wet for her boys.

Jake placed his hands on her hips, the leash handle around one of his wrists, and thrust into her. She was indeed soaking wet, and she moaned loudly as her son slammed into her. Jake gave a harsh pull on the leash, and Naomi's moan became stifled as she was choked.

"Dad's right, fertile pussy is the best! " Jake exclaimed. He gave the leash a little slack, but then gave a hard smack to Naomi's ass.

"Are you -ah!- excited to put a baby in Mommy's -ah!- womb?" Naomi asked, interrupted by the occasional moan.

"Heck yeah!" Jake replied. He gave her another smack as he fucked her, leaving a red mark.

"Hey, I heard we're fuckin' Mom?" Jason asked as he, Jeremy, and Emily entered the room.

"We're not fucking her, we're breeding her!" Jake said. "Right, Mom?"

"Mmm, yes!" Naomi moaned, her voice coming out choked. "Mommy needs you to -ah!- breed her!"

"That's the same thing, though." Jeremy said.

"No, dude, it's all about, Idunno, attitude or somethin'!" Jake argued. "Oh, dang, I'm really close…"

"Shoot it de- ach!" Naomi started, before being cut off by a sudden pull of the leash. Jake thrust as deep as he could into her, and Naomi felt him twitch and throb as his seed flowed into her, hopefully taking root in her womb.

"Heck yeah, that's good…" Jake panted as he pulled out. "Remember what Dad said! Get it in deep so you're more likely to knock her up. Which one of you wants to go next?"

"Me." Jeremy said. Jake handed him the leash, then left the room.

Emily did her best to focus on moving the laundry along as she listened to her mom get fucked. At least Jeremy was relatively quiet. The rhythmatic "slap! slap! slap!" noises were almost soothing, although Naomi's loud moans and screams certainly weren't. She occasionally glanced over to watch, but mostly kept to the task at hand. Dammit, this is making me horny. She thought to herself. I wanna get fucked like that. Ugh, I'll have to wait until later. Lame. She left the room with a basket of folded laundry, and putting it away at least gave her a brief moment of peace.

When she returned to drop off the basket and start the next load, Jeremy was nowhere to be seen. In her absence, he'd finished, and handed Naomi's leash to Jason.

"I'm gonna knock you up so good, you whore!" Jason shouted as he fucked her roughly. He was causing her ass to jiggle forcefully, and one leg of the table was occasionally slamming into the ground. "Then we're gonna fuckin' do it again!"

"Mmm, yes! Yes!" Naomi screamed. "Mommy is your breeding sow! I belong to you!"

"Fuck yeah, I'm gonna…" Jason growled, being interrupted as he came. Like his brothers, he plunged deep into his mother's pussy, planting his virile seed into her womb alongside his brothers. He grunted and groaned as his cock pulsed inside her. When he was done, he took a minute to catch his breath.

"Thank you, Jason." Naomi panted.

"Yeah, okay, good girl." Jason panted back. He reached over, unhooked the leash from her collar, then walked out of the room to go play video games.

"Emily," Naomi said breathily, "did you have any trouble with the laundry?"

"Uh, nope, all good." Emily answered.

"Very good, then." Naomi said. She slowly got up from the table, took a minute to steady her footing, then headed to the kitchen. Dinner wasn't going to prepare itself, after all.

Session Start

[13:12] TheFool Hey!

[13:14] CollaredMom Hello :)

[13:15] TheFool How are you?

[13:15] CollaredMom I'm well, and yourself?

[13:16] TheFool I'm okay

[13:16] TheFool Any updates?

[13:17] CollaredMom Yes, actually :) My latest test came back positive!

[13:17] CollaredMom It would seem that one of them found their mark :) I'm pregnant, at least for now

[13:18] TheFool Congratulations!

[13:18] TheFool For now?

[13:19] CollaredMom Yes, well, it's still a bit early. We're going to give it a few more weeks to make sure it 'sticks', you understand.

[13:20] CollaredMom If something were to go awry, it would be within the first month or so, if memory serves

[13:20] TheFool Ooooh, I see

[13:21] TheFool So what's that mean for you?

[13:22] CollaredMom Well, we won't be making any official announcements for a while yet, but it seems I'm clear to party at Megan's again ;)

[13:23] CollaredMom Oh, yes, and our sons' friends won't have to use protection anymore. Just as well, we went through quite a few condoms…

[13:24] TheFool Congratulations to them!

[13:24] TheFool So, any idea which of your boys is now a father?

[13:25] CollaredMom None whatsoever :) And we intend to keep it that way

[13:25] TheFool Wow

[13:26] CollaredMom If all goes well, I should be able to bear them several more. I'm sure they'll each be able to get a turn to get me pregnant at least once ;)

[13:27] TheFool Damn, lucky boys

[13:29] TheFool So, how are you feeling? Physically, I mean

[13:30] CollaredMom I'm feeling fine, haha :)

[13:31] TheFool No, like, idk, morning sickness or whatever?

[13:32] CollaredMom I only had that when I had Jason, haha. The others were much easier :)

[13:33] TheFool Oh, that's good to know

[13:34] CollaredMom I appreciate your concern about my well-being, though, haha

[13:35] TheFool Just wanna make sure my favorite MILF stays happy and healthy!

[13:36] CollaredMom Aw, that's very sweet of you, Terry :)

[13:37] CollaredMom Although, a cynical individual might think you're just trying to butter me up so that I'll let you visit ;)

[13:38] TheFool Perish the thought!

[13:39] CollaredMom I kid, I kid :) Not that I'd be *opposed* to such a thing. Perhaps I'll bring it up to Master, haha ;)

[13:40] TheFool That would be amazing, but you really don't have to

[13:41] TheFool Hey, I gotta get going. Great seeing you again!

[13:42] CollaredMom You too, take care :)

Session Close

It was a quiet day, and Naomi lay on the living room couch. She was a few months along now, and the bump on her stomach was rather prominent. Her breasts had also noticeably grown a bit, and she occasionally leaked milk onto her piercings.

She had some rare time alone. The kids had the day off, but they were out spending time with friends. And so, she found herself home by herself, watching some trashy daytime TV. It wasn't particularly good, or even interesting, but it was an amusing guilty pleasure of hers.

Suddenly, she heard the front door open, and a few sets of footsteps started to approach the living room. From the sounds, she could tell it was Jason, his friend Rag, and Emily. Her suspicions were confirmed when the door opened and the three of them stepped through.

"Hey Mom!" Emily called out. This time she was wearing normal clothes, having decided to forego her collar for the moment. "You mind if we use the TV?"

"Go right ahead." Naomi replied. "Do you need me to move?"

"In a bit." Jason answered as he unzipped his pants. Instinctively, Naomi rolled onto her side and lifted one of her legs.

"Of course." Naomi said.

As Emily and Rag set up their game console, Jason knelt on the couch, straddling one of her legs and taking hold of her other leg for support. In a single, quick motion, he thrust into her soaking wet pussy, and started to fuck her like he owned her, which as far as Naomi was concerned, he did. Naomi did her best to keep quiet as she got fucked, trying not to disturb Rag and Emily. The loud, wet "plap-plap-plap" sounds made as Jason collided into her were almost drowned out by the music and sound effects from the racing game they were playing.

Naomi had noticed that once her stomach had started to grow, her boys treated her differently. They fucked her with a primal intensity that they hadn't before. Her pregnancy had awoken something in them, as if the child in her womb was a mark of ownership permanently branded onto her; the bump on her belly seemed to scream to the world "This whore is property of her sons". They fucked her rougher and came harder with her than they ever had before, and it made Naomi proud to be their mother.

"Yes!" Emily cheered as she won a race against Rag. " In your face! "

"You just got lucky." Rag retorted. "Hey Jason, almost done? Or should we start without you?"

"Also, I want the couch." Emily added. "It's more comfortable."

"Almost done…" Jason panted. A moment later, he was close, and he pulled himself out of Naomi's pussy. After a few quick strokes, he shot cum onto her bulging stomach. Ropes of hot, sticky semen landed on Naomi's belly in thick spurts, before rolling down her stomach.

"Thank you, young master." Naomi said, panting to catch her breath. "Will that be all?"

"Yeah." Jason answered. "Go clean up before this gets on the couch."

"Of course." Naomi replied. She slowly stood up off the couch, then made her way to the bathroom to wash herself off, and the kids immediately claimed the couch for video gaming the second she left.

Notes:

Hey everyone, I just wanted to make a note here to say that I didn't really plan on adding Naomi's baby as a character in future stories, or really going through with a story about her giving birth (that's not really my thing). I also didn't really plan for this to change the dynamics of her family permanently, so don't expect the events of this story to shake up the status quo much. Pregnant Naomi may show up again though in future fics as a sort of...alternate "mode" for her, for lack of a better word. Let me know what you'd like in the future from this series!

Chapter 5: Naomi Gets Set Up

Summary:

Naomi's summoned by her sons' friend, Rag, for a quickie at his place, but things take a sudden turn for the unexpected when his house proves less empty than she thought

Chapter Text

Naomi sat in her car, having just parked outside the house of her friend's son, Rag. Rag had texted her earlier, saying that Sai, his mother, would be out for a while, and that Naomi should come by for a quick hookup. Naomi hadn't thought too much of it, and was always eager to please her sons and their friends. Naomi saw that Sai's car wasn't parked in the driveway, confirming that she was, in fact, out. Satisfied that it was safe, she stepped out of her car.

Naomi walked up to the front door and rang the bell. She wore a red sundress with a floral pattern on it, and a cute pair of sandals that showed off her black nails. She also, of course, had her collar on. She never took it off, and what it signified wasn't immediately obvious to anyone who wasn't in the know about her lifestyle. She hadn't bothered putting on a bra or panties before she left the house; they would only impede access.

"Hey there, Mrs. S." Rag said as he opened the door. "Come in, come in."

"Thank you, Rag." Naomi replied as she stepped inside. "And just 'Naomi' is fine." She looked around a little bit as Rag closed the door behind her. "Will your mother be gone long?"

"We'll be done before she gets back." Rag reassured her. "Here, let's go to the living room."

The living room was close to the front door, separated only by a short hallway. A big couch sat near the middle of the room, in front of a large TV. A desk with a computer on it sat off to one side, next to a bookshelf with various books and miscellaneous items on it.

"Hey, Naomi, take off your clothes." Rag instructed.

"Don't want to waste any time, I see." Naomi replied. She took off her sandals and then stripped off her dress, revealing the ring piercings in her nipples. "How would you like to take me, then?"

"Uh, y'know, the usual." Rag answered. "Doggystyle on the couch."

"Very well." Naomi said. She got onto the couch and got onto her hands and knees. It was second nature to her at this point. Rag got behind her. She heard a zipper being undone, felt his hands grab her hips, and then felt him thrust into her. Rag didn't waste any time getting into a rhythm. He'd had plenty of experience with Naomi by now.

It all felt right to Naomi. She was serving what she felt was her purpose. There was also the added thrill of being in someone else's house. She let out several loud moans, feeling herself get lost in her own libido.

"Hello, Naomi." Sai said, leaning against the door frame with her arms crossed. She looked at Naomi with a cold, unreadable expression. Naomi looked up at her and started to panic. She felt exposed. The weight of her swaying breasts felt unbearably heavy in the moment, and she instinctively moved her arms to cover her chest. Rag hadn't stopped, and it occurred to Naomi that the two of them must have planned this. "I thought Rag was exaggerating when he said how compliant you were. Don't worry, you're not in trouble."

"H-hello, Sai…" Naomi panted. She took it as a good sign that Sai didn't seem angry, and that she intended to let Rag finish. Rag had slowed down a little, trying not to make too much noise or overwhelm Naomi too much. He showed no sign of stopping, or any hesitation.

"Honestly, you could stand to be more discreet." Sai continued. "It wasn't particularly difficult to guess you were up to something. I wanted to ask you about it, but I assumed you'd play coy. Now, you can't really do that."

"I see." Naomi replied quietly. She wasn't entirely sure how to respond. Indeed, she would have liked to brush off Sai's questions, but she was naked in Sai's living room and Sai's son was balls-deep in her pussy. There was a lot she could talk her way out of, but certainly not this. A painful silence permeated the room as Sai stared at her, broken only by the soft, rhythmic "slap-slap-slap" as Rag continued to fuck her.

"You didn't notice the camera, either." Sai pointed out, gesturing vaguely towards the bookshelf with her head. Naomi followed, and saw a small camera that had been set up on the bookshelf. Dammit. Naomi thought to herself. "You really are rather careless, Naomi. I don't have plans for this little home movie, yet, though. I just like having the leverage. It keeps people compliant."

"What -ah!- do you -ah!- want from me, then?" Naomi asked. She found it hard to keep her cool while also getting fucked. She suspected that it was deliberate on Sai's part.

"I guess I just wanted to ask if it was true." Sai continued. "You really just let your boys fuck you whenever?"

"Yes." Naomi answered.

"That's dedication." Sai replied. "Admirable, I suppose. And you really don't wear clothes at home, either?"

"That's co-" Naomi started.

"Fuck, I'm cumming!" Rag groaned. He thrust deep into Naomi and filled her with warm, sticky cum. Naomi would have savored the sensation if she weren't in her current predicament.

"Take your time." Sai said.

"Mom, don't make this weird." Rag panted as he finished his orgasm. He pulled out of Naomi and then zipped his fly up.

"This is already pretty weird, Rag." Sai shot back. "Grab that bowl off the shelf and put it under her, then you can go." Rag went over and grabbed an empty dog bowl sitting on the bookshelf, placed it under Naomi, and then left the room. Sai turned her attention to Naomi. "You, stay there."
"Do you have anything else you want from me, Sai?" Naomi asked. There was a slightly uncomfortable pause as Sai thought of an answer, or at least pretended to. Naomi felt the cum start to flow out of her, and was a little startled by the sound of a metallic "splat!" as a drop landed in the bowl.

"I'm enjoying just watching you, to be honest." Sai replied eventually. The cold expression on her face did not indicate enjoyment to Naomi. "Your little nudity rule applies at my house too, now, of course. You can do as you please here so long as you clean up your messes."

"I appreciate your hospitality." Naomi replied, her tone slightly bitter. Cum continued to drip out of her, forming a little puddle in the bowl. "May I go, then?"

"I don't want you dripping in the house." Sai answered. "Finish pushing my son's cum out, first."

"As you wish." Naomi said. She spent a minute straining and pushing, and the last of Rag's cum fell into the bowl in long, sticky globules. "I think that's most of it."

"Good." Sai replied. "Now lick it up, and then you can go."

"I… what?" Naomi asked, taken aback.

"You wear a collar, don't you?" Sai asked. "You know, like a dog. I want to see you lick out of a bowl like one." Sai stared at her expectantly, her expression unchanging. "You're not in a position to refuse."

"Very well." Naomi replied. She turned herself around, bringing her head over the bowl. Naomi steadied herself with a deep breath, then brought her face down close to it. She stuck her tongue out and started lapping cum out of it. It was sticky and salty on her tongue, although it had cooled down a little and wasn't quite as warm. She licked and slurped obediently, not leaving a drop in the bowl. With all the cum swallowed, she turned to Sai, seeking approval.

"Ha, that was great." Sai said. "Alright, you can go. I'll be in touch." Sai walked out of the room, leaving Naomi alone. Naomi, feeling a little rattled and yet also quite horny, quickly threw her clothes back on and left Sai's house, before driving straight home, unsure what to tell her Master about what had happened.

Chapter 6: When Terry Met Megan

Summary:

After hearing many stories and seeing more than a handful of video clips, Naomi introduces Terry to her friend Megan, a MILF with an insatiable lust, a surprisingly sharp wit, and the occasional oddball tendency. Megan ends up sharing some footage from a daring endeavor at the local high school's last homecoming festival.

Chapter Text

Session Start

* Now talking in #meetup

TheFool has joined #meetup

[21:00] CollaredMom Good evening, Terry :)

[21:00] TheFool Hey! Is Megan joining us?

[21:01] TheFool I'm really excited to meet her

[21:01] CollaredMom Give her a minute :)

[21:02] CollaredMom She should be on soon. Megan is punctual if nothing else, haha

OrgyMom has joined #meetup

[21:03] CollaredMom Speak of the devil…

[21:04] OrgyMom and I shall appear!~

[21:04] TheFool That's a hell of a nick

[21:05] OrgyMom Thank you~ I picked it to get attention!

[21:05] OrgyMom Then it worked too well and I got overwhelmed by messages from randos and so I stopped coming online

[21:06] TheFool Oh. I'm honored you decided to come back just for me

[21:06] OrgyMom As you should be!

[21:06] CollaredMom I've seen Megan's messages before, haha. She's quite popular :) More popular than me, if you can believe it!

[21:07] TheFool I can, strangely enough

[21:07] OrgyMom Terry, right? I'm Megan, nice to meetcha o:

[21:08] TheFool Yep, that's me! Nice to finally meet you. I've heard stories

[21:08] CollaredMom And seen videos ;)

[21:08] TheFool Those too

[21:09] OrgyMom I hope I'm everything you hoped and dreamed o:

[21:09] TheFool You already are, from what I've seen

[21:10] OrgyMom So, why "TheFool"? Doesn't seem all that flattering to yourself

[21:11] TheFool It's a really lame pun. "Terry" sounds kinda like "tarot", and The Fool is the first major arcana

[21:11] OrgyMom HOLY FUCK

[21:11] CollaredMom Ah, so *that's* where it comes from. Clever, haha :)

[21:12] OrgyMom THAT'S SUCH A GOOD FUCKING PUN I'M SO MAD I DIDN'T GET THAT

[21:12] TheFool Lmao! Thank you!

[21:13] CollaredMom It seems you'll have to step up your wordplay, Megan :)

[21:14] OrgyMom No, it's fine, I'll just file a cease and desist. Puns are my trademark, you're infringing, Terry D:

[21:15] TheFool I don't think that's legal

[21:15] OrgyMom I'm a lawyer, I can confirm that it would be 100% legal

[21:16] TheFool Lmfao. Wait, are you actually?

[21:16] OrgyMom Yep! Haven't been to court in a while, tho. Still got my license~

[21:16] TheFool Wow

[21:17] CollaredMom I was blown away when you told me you used to work in a big law firm, haha. You're very unlike what I imagined a lawyer to be :)

[21:17] TheFool So, did you ever have any dangerous clients? Maybe give them one last chance for pussy before they go to prison?

[21:18] OrgyMom No, I wasn't that kind of lawyer ;P

[21:18] TheFool Upstanding and squeaky clean then, huh?

[21:19] OrgyMom No, like, I did property law, my dude. It was all civil stuff. Our "clients" would be, like, big organizations looking to buy land

[21:19] TheFool Ooooh

[21:20] OrgyMom Although, I'm pretty sure there was a woman at our firm who was sleeping with someone on one of the local school district's boards when we were working with them. That bitch had a few screws loose.

[21:21] TheFool Would that be LAUSD?

[21:21] OrgyMom I can neither confirm nor deny

[21:22] CollaredMom Oh dear, it wasn't on *our* local school district, was it? Is it someone I know?

[21:23] OrgyMom Oh, have I not told you this story, Naomi? Ask me about it sometime next time you see me!

[21:23] TheFool Did you ever have sex at work?

[21:24] OrgyMom Not as much as I would have liked ;P but yeah, more than once~

[21:24] TheFool Ever sneak in any boys?

[21:25] OrgyMom No, but *god* I wish I had. Building security was pretty tight, though, and I could never think of a good excuse to smuggle them in .

[21:26] CollaredMom You could have said it was an internship program :)

[21:27] OrgyMom There's a whole fucking process for getting interns, don't even get me started!

[21:27] TheFool A fucking process, you say?

[21:28] OrgyMom No, not like that D:

[21:28] OrgyMom It's a lot of very unsexy paperwork and whatnot

[21:29] TheFool You can't just have them get you coffee?

[21:29] OrgyMom Not officially .

[21:30] OrgyMom Also, I think the interns we *actually* had tended to be pre-law undergrads

[21:31] TheFool In other words, too old for you?

[21:32] OrgyMom . . OKAY LOOK IT SOUNDS REALLY BAD WHEN YOU PUT IT THAT WAY

[21:33] CollaredMom I imagine the actual problem was that Megan would then have to befriend college students in addition to her current roster :)

[21:34] OrgyMom Yeah!

[21:34] OrgyMom I mean Terry has a *bit* of a point cause it's not as thrilling with them . BUT STILL

[21:35] CollaredMom Our local high school is much more lax about visitors, haha ;)

[21:35] OrgyMom Hell yeah ^.~

[21:36] TheFool Can't bring the boys to you, so you go to the boys?

[21:36] OrgyMom I fuck smarter, not harder

[21:37] OrgyMom I fuck pretty hard, though, tbf

[21:38] CollaredMom Oh, that reminds me, the school homecoming festival is coming up soon

[21:39] CollaredMom Megan, have you made arrangements with you-know-who? :)

[21:40] OrgyMom Oh yeah, I forgot, thanks for the reminder

[21:40] TheFool "You know who?"

[21:41] OrgyMom One of the teachers there knows, uh, about us. He's a total sleazeball, but he's useful

[21:42] OrgyMom So when the homecoming festival rolls around, we do a little favor him, and he lets us use his room for "storage" during the festival ;3

[21:43] TheFool What kind of "favor"?

[21:43] OrgyMom The kind that makes his dick feel big ;P

[21:44] CollaredMom At least he never takes too long, haha ;)

[21:46] OrgyMom So, a bunch of the boys set up a stand outside his room selling bacon for the festival, and we keep extra food supplies and stuff in Sleazeball's classroom. We also just keep some sluts there too for the boys in the know ^.~

[21:46] TheFool Amazing

[21:47] CollaredMom He teaches science, as well, so he has rather thick curtains and lab tables in his room :) It's quite spacious

[21:48] OrgyMom I miiiight have a little footage of last year's if you wanna see that, Terry

[21:49] TheFool I'm always willing to see what you have to share!

[21:49] CollaredMom It's true, he is :)

[21:50] TheFool No pressure, though, if you can't find it

[21:51] OrgyMom Found 'em! Uh, gimme a minute to do a little editing magic and stitch these together so I'm not sending you a ton of different clips

[21:52] OrgyMom There's not a good one of the entire thing, sadly ;-; there was just a few clips some boys recorded

[21:53] CollaredMom We could get Henry to be our cameraman :)

[21:53] OrgyMom And deny those kids his sweet bussy?

[21:54] TheFool 'Bussy'?

[21:54] OrgyMom Boy-pussy! (it means his butthole)

[21:55] CollaredMom You have such a way with words, Megan :)

[21:55] OrgyMom Hell yeah!

[21:55] TheFool That's a new one

[21:56] OrgyMom The young people teach me their slang in exchange for MILF pussy

[21:57] CollaredMom So youthful and hip with the kids :) Truly I envy you

[21:57] OrgyMom I'm like a decade older than you, Naomi :x You could be as cool as me!

[21:58] CollaredMom Perish the thought! I'd hate to infringe on your coolness :)

[21:59] TheFool That's right, she did threaten to sue me over puns, I'm sure she'd take legal action to protect her coolness, too

[22:00] OrgyMom Fuck yeah, gonna take you both to Megan's Sex Court

[22:01] CollaredMom Is that like Judge Judy but with more sex?

[22:02] TheFool I'd be down for that

[22:03] OrgyMom No, it'll be like that one game my daughter likes, where the trials are all a sham and they're run by an evil talking teddy bear. Except with fucking instead of murder. And I'm the bear.

[22:04] TheFool Can't say I'm familiar with that

[22:05] OrgyMom Hang on, I'll call Juli over, she can explain it

[22:06] OrgyMom (I'm waiting for the thingie to finish compiling or w/e, I will not have my daughter explain her weird anime bullshit)

[22:07] TheFool I thought compiling was for code. Don't videos "render"?

[22:08] OrgyMom Idk I'm not a nerd

[22:09] OrgyMom Ok, done! Sorry if it's a little disjointed. I threw in a couple pics we took, too~

[22:10] TheFool I'm sure it will be fine!

[22:10] -OrgyMom- sent 4

The video file starts with a still image of Megan, her wife Tanya, her daughter Juli, and Naomi, standing fully clothed in a classroom, with their arms around each other and smiling to the camera. Megan stands around 5'8", has dirty blonde hair, blue eyes, blood red nails, a slight tan, and is wearing a dark red shirt and a pair of jeans. Tanya, a dark-skinned black woman with black hair, brown eyes, and purple nail polish, standing around 5'9", is wearing a dark blue blouse and a matching skirt. Juli stands around 5'6", has pale skin, platinum blonde hair, deep blue eyes, dark blue nail polish, and is wearing a tank top and miniskirt combination that shows off a lot of her skin. Naomi, the shortest of the group at 5'4", has chestnut brown hair, green eyes, black nails, her usual black collar, and is wearing a red sundress.

The video then transitions to another picture, of the same four women in the same spot, but wearing less clothing. Megan has changed into a black corset, black nylon stockings, and a pair of shiny black 5-inch heels. Tanya is wearing blue fishnet stockings and a clear plastic pair of high heels. Juli is wearing a fishnet body stocking that covers her entire body, and has two bar piercings through her nipples. Naomi wears only her collar, and has a chain connecting the ring piercings in her nipples.

The video then cuts to a view outside, showing a busy crowd bustling around an outdoor high school campus. The video seems to be shot on a phone by someone standing behind a table with a griddle on it. Bacon sizzles loudly on the griddle as an older boy keeps a careful eye on it, flipping pieces over and taking cooked pieces off. A long line of people stands in front of the table.

Boy 1: [From behind camera]: Everybody loves our bacon!

Boy 2: Hell yeah, man. The bacon stand is always super popular. [Pause]. Think, uh, think you could go grab another pack for me real quick? I'm runnin' low here.

Boy 1: Of course, of course!

Boy 2: Don't take too long, we got customers!

Boy 1: I gotcha, I gotcha!

The camera turns around, showing a classroom building immediately behind the stand. The camera moves as the boy walks past an opening and heads for a room near the back of the building. The journey takes less than a minute before he opens the classroom door.

The room has blackout curtains drawn, and the lights are on. Desks have been moved from the rear half of the room, creating an open space that has been filled with soft mats. Megan and Tanya are side by side each straddling a boy, with each one also having another one behind them. They hold hands as they're both double penetrated, doing their best to keep quiet as the boys excitedly fuck both their holes. Juli and Naomi are both on their hands and knees being spitroasted. Naomi's moans are muffled as she sucks the dick in her mouth; Juli makes audible glugging noises as her face is fucked roughly.

Boy 1: Any of you almost done? They need more bacon up at the front.

No one responds for a few seconds.

Megan: Guess you're SOL.

Boy 1: Ugh, fine, but I'll be back.

The video suddenly cuts to a different clip, showing a POV shot of a boy fucking Tanya's ass doggystyle, gripping her hips with one hand. Her ass is round and soft; it jiggles and produces a loud, satisfying slapping noise as he thrusts into her. Other sex sounds can be faintly heard in the background. The clip ends when he seemingly drops the phone. It is immediately followed by a still shot of cum dripping out of Tanya's asshole.

The next clip shows Megan and Juli sitting next to each other on top of a lab table, each giving a different boy a footjob. Megan and Juli work their respective cocks with expert dexterity; years of practice are evident in their technique. They both have the cock wrapped between the arches of their feet, stroking them up and down effortlessly. Precum leaks profusely from both cocks. Megan and Juli flex their toes for the camera, showing off their red and blue nails, respectively.

Boy holding camera: Wow, I wonder who's gonna win?

Juli: This isn't a competition.

Megan: Me.

Juli: We'll see about that, Granny.

Megan: Granny's gonna get her dick-suckin dentures. [Chuckles burst out from the room]

After a minute, Megan does indeed win. The boy between her feet grunts and bucks, letting out loud groans as he shoots his cum. It lands on Megan just below her tits, covering her stomach in warm, sticky cum. She quickly wipes it off with a rag.

Megan: Told ya! You got a ways to go, Jules.

Juli: One day I'll pass you, Shisho.

Megan: You kids and your anime. Do people still go Super Saiyan?

Boy holding camera: Yeah, actually!

Megan: Huh, good for them.

Megan gets off the table and squats near the boy fucking Juli's feet. Juli shifts her 'grip' so that she's stroking the shaft with her toes, rubbing against the head with her big toes. Megan takes the tip, as well as Juli's toes, into her mouth, swirling her tongue around the sensitive head and sucking gently. He barely lasts ten seconds, and lets out an ecstatic moan as he orgasms. Cum floods Megan's mouth, but then slowly oozes past her lips, running down the boy's shaft and adding an extra white coat to Juli's blue nail polish.

The video's final cut shows a still image, with a picture of Megan, Tanya, Juli, and Naomi on their knees, each with cum on their faces and chests. Megan and Tanya are flashing big smiles and peace signs. Juli's giving a thumbs up. Naomi just looks like she's happy to be there.

[22:23] TheFool Wow. You're *good*. I'm amazed you don't get caught.

[22:24] OrgyMom I'm super duper sneaky! Like the Solid Snake of sluttiness

[22:25] CollaredMom There you go again with your references :)

[22:26] CollaredMom Oh my, I didn't realize how late it had gotten. I need to be heading off. Do take care, everyone :)

[22:26] OrgyMom OH SHIT! Me too!

[22:27] TheFool Oh fuck I forgot I have work tomorrow…

[22:28] CollaredMom It's much later where you are, isn't it, Terry?

[22:28] TheFool Yep. C'est la vie.

[22:30] OrgyMom Well, it was very nice talkin' to ya, Terry~ I'll be sure to come by again and bug you about stuff!

[22:31] TheFool It would be no trouble at all! You're a very lovely woman, Megan.

[22:31] TheFool You too, Naomi.

[22:32] CollaredMom Thank you, haha :) Take care!

[22:32] OrgyMom TTYL!~

[22:32] TheFool Bye!

Session Close

Chapter 7: Rag's Week in Chastity

Summary:

Sai and Rag decide to experiment with chastity and cuckolding, and Rag keeps a journal for the 5 days he's locked up.

Notes:

(See the end of the chapter for notes.)

Chapter Text Day 1: Monday

Mom and I decided to start experimenting with chastity stuff, and as part of that she says I have to keep a journal of it. Oh boy. I hope I don't regret this by the end. I can last a week, I think.

Today wasn't too bad, but we only just started. Mom put some cold water on my dick so I wouldn't get hard, then put the chastity cage on me before I headed to school. I can definitely feel it, but it's not very obvious when I'm wearing pants or something. It hurts a little when I try to get hard, but it's not as bad as I thought it would be.

My friends Jason and Brian know about what we're doing, so they didn't have any questions. Mom sent all three of us pictures, though. The ones she sent me were just 'suggestive', with nothing actually exposed, but my friends got full-on nudes. I was a little jealous, but I tried not to think too hard about it. I just focused on school stuff and getting through the day.

I had to go straight home after school without visiting Naomi first, which kinda sucked. I couldn't help but think on the walk home what I was missing out on over at their place. It passed quickly, but I imagine this could get worse over the week…

At least Mom was pretty merciful today at home. She didn't act much different from usual, although she did ask me how the cage was. Her outfit was also a little more revealing than usual. She didn't wear a bra under her top, and wore a short skirt instead of her usual jeans. I can tell she's got much more in mind for later, though, knowing her.

The hardest thing today was that Jason kept sending me pictures from his place to show me what I'm missing out on. They were mostly just pictures of his mom naked, some with cum dripping out of her. I have never wanted to fuck Naomi more than I do now, since I can't fuck her for a week.

Mom said she was going to work from home for the rest of the week, too, so she wouldn't have to worry about leaving work and getting home on time to see my friends. This is certainly gonna be an interesting week for both of us.

Day 2: Tuesday

Today started off okay. Mom didn't send me anything while I was at school, and my friends who know about it, Jason and Brian, didn't tease me about it either.

Things started to get "hard" (pun intended!) right as school ended. Instead of going to Jason's place, Jason and Brian walked home with me from school. They didn't say anything, or even really mention it, but I knew they were coming along with me because they wanted to bang my mom. Thinking about it was really exciting, and it made me get hard in my cage.

When we got home, things were- damn, I'm getting hard again just thinking about it! Ugh, I can't wait for this to be over already! Well, anyway, we get home, and I knew they were gonna do something with Mom. Like, eventually. I didn't think it would happen so fast, or be so intense.

Mom was waiting in the living room when we got home. Without saying anything, Jason just walked up to her and smacked her in the face! She'd kill me if I did that. In fact, I thought she was gonna kill him for it, too, but he didn't actually do it all that hard, and she seemed into it (I'm pretty sure they agreed on it beforehand, now that I think about it). Mom said she was willing to experiment with letting Jason treat her like he treats Naomi, his own mom. I got really, really jealous! She said it was only for the week, too, which stung, but in kind of a good, sexy way? I got so hard I thought I might break the cage.

Jason whipped his dick out, and Mom just started sucking it without any hesitation. I could hear her moaning with it in her mouth, and she kept looking up at him like she was really horny for him. It was so hot! I really wanted to jerk off, but I couldn't.

Mom told me to do my homework in the living room, and I couldn't exactly say no. Right after she said that, Brian came up, slid her jeans and her panties down, and started fucking her while she sucked off Jason. I tried my best to concentrate, but it was hard. Having my mom suck and fuck my friends in the same room was, to put it mildly, a little distracting. Mom was pretty loud, between the moaning and how Jason was making her gag.

I at least got a little 'break' when they came and had to recharge for a bit, although I still felt really worked up. Even when it was over, it was all I could think about, and I knew they'd start doing more stuff with her again.

Jason was back up first. Mom was laying on the couch with her phone, and Jason just lay on top of her and started fucking her. She got really into it; she wrapped her legs around him, clawed at his back, they even made out for a little bit. Personally, I don't really wanna make out with my own mom, but I was still kinda jealous.

Brian got basically the same treatment. I wasn't paying that much attention, to be honest. I got stuck on a tough math problem and I kinda lost track of what was going on around me. I actually didn't even notice when he finished… I mean, at least my homework got done.

Things got quiet after they left, which was nice. I was really worked up, but at least I finished all my homework. I'm about to go to bed. I wonder what's in store for me tomorrow…

Day 3: Wednesday

Ugh, I woke up feeling really horny this morning. I woke up early, too. I could have rubbed one out if I didn't have this cage on. I read one of my textbooks until it went away, that seemed to work.

School wasn't so bad, although Jason and Brian teased me more than they had yesterday, at least when I saw them. They told me it was hot having Mom act submissive for them, and how it was too bad she wasn't going to do that for me. That was… very distracting. I was able to hold it together until it calmed down later in class, but it was hard to pay attention. I'm starting to get turned on by the way it hurts a little when I try to get hard.

I didn't see Jason after school, which I didn't think too hard about at the time. Brian said he'd left early to go home, and, well, I can't say I blame him. Brian left to go to Jason's place, probably to fuck Naomi, so I decided to walk home by myself. I figured they'd come by my place later to do stuff with Mom.

In a twist I probably should have seen coming, Jason was already at my place, and he'd also brought his two younger brothers, Jeremy and Jake. I learned this when I opened the front door and heard moaning and slapping coming from inside the living room. Mom was on the couch, getting fucked doggystyle by Jake. Part of me was annoyed, but it also made me really horny. Jason waved and said "Hi" to me; Mom didn't even seem to notice I was there. Jeremy said they'd been taking turns with her for around half an hour, and that they were planning to stay for a couple more hours. I throbbed in my cage when he said that. I've seen these three in action, they can keep a train running for a long time. Naomi gives them a lot of practice.

I tried focusing on my homework, but I lasted all of 20 minutes before I couldn't take it. I gave up and just stared as Naomi's boys took turns with my mom. It was really hot to watch. All three of them have a lot of experience already, and the contrast in skintones between them and Mom was a big turn-on.

Since I couldn't concentrate, and Mom caught me staring, I had to go finish up my homework in the dining room. That didn't make it much easier to concentrate though, since I could hear *everything*. All the slurping, moaning, grunting, slapping, smacking, and all the dirty talk, mostly from Mom (not that I could understand all of it, since Mom never taught me Hindi).

I tried jerking off through my cage by tugging on it, but that didn't help. If anything, it made it worse, since I kept expecting to get stimulation. Part of me felt like I'd be able to cum if I kept doing it, even though I knew it was useless.

After what felt like forever , Jason and his brothers left. Mom was an exhausted mess on the couch, and they got cum fucking everywhere. Mom told me to go get a towel and wipe it off her. It was so degrading, but it turned me on even more.

I don't know how I'm going to sleep tonight, I feel really worked up. Mom seemed to notice. She said I can have a ruined orgasm through my cage tomorrow if I behave myself. I'm… sorta looking forward to it, but I'm not sure how much that'll help.

Day 4: Thursday

I cannot wait for this week to be over! Today was the worst one yet.

When I got to school, I got a text from Jason. I opened it, and he had a picture of himself in our living room, sitting next to Mom! Part of me was jealous, part of me also realized that they were going to send me stuff all day. I felt a lot at once. I was a little annoyed and preemptively frustrated, but more than that, I got *really* horny, and that overrode everything else. I had a feeling that concentrating on school stuff was gonna be impossible, and I really wish I'd been wrong.

First period wasn't too bad, although that's mostly because I wasn't checking my phone in class. I'm a very good boy. Usually. I really wanted to check, and it felt like my phone was burning a hole in my pocket, but I was able to keep my focus long enough to make it through class.

Then I made the mistake of checking on my way to my second period class.

They only sent me two pictures, and neither of them were too explicit. But I think that was worse, because I wanted to see more. It left a lot to the imagination, and my imagination went wild. The first picture just showed them kissing. The next picture, sent maybe 10 minutes later, was a closeup of Mom showing her mouth, her neck, and the upper part of her chest. She was clearly topless, but her boobs were just out of the camera's sight, and there were a few trails of cum near her lips. Along with that pic was some text saying they'd send me more later in the day.

I got hard, painfully hard. I wanted to see more, I needed to see more. I sent a reply asking if I could do anything to get Jason to send them sooner. Right as I got to my next class, just before the bell rang, I got a reply from him that showed the upper half of my Mom's bare back, as if she was in doggystyle, with the text "Busy taking more pics and vids rn".

I almost came in my pants when I saw that. I thought I was gonna explode. I didn't just want more, I needed more! I started writing a message begging for more pictures, but I was snapped out of it by the ringing of the bell. My 2nd period teacher is pretty strict about phone stuff, so I begrudgingly put it back in my pocket.

Not being able to check made me want to check even more. It was all I could think about. I don't even remember what the teacher was talking about. I had to try really hard to pretend I was taking notes. Ugh, I'm gonna have to ask someone else for what we covered.

I pulled out my phone as soon as class was over. I got a text from Mom saying to make sure I paid attention in class and was a good student. She also sent a picture with what looked like cum covering her dark purple toenails. She knew exactly what she was doing.

I couldn't help myself in third period. At least my teacher for that class doesn't seem to care much about people using their phones. I sent messages to Jason and Mom asking for more pictures. I didn't care what was going on in class. Jason was totally in on it with Mom, though. He told me to be a good boy and pay attention, and that he'd send way more stuff during lunch. He included a picture of him and Mom naked in my bed. I asked if they'd just done it or were about to do it, but he didn't respond. I checked my phone every 30 seconds or so after that, but he never got back to me.

Right before my last class before lunch started, Mom sent a selfie she took while sucking Jason's cock. I was so horny, and the way the cage bit into me when my cock tried to get hard turned me on even more. I wanted to jerk off so bad. I wanted more, so, so bad. She said that was the last thing she would send before lunch, though. Not that it helped me pay any attention in that class. It was agonizing waiting for the lunch bell to ring.

When class was finally over, I made a beeline to the table where I usually eat with Jason and Brian. I sat down and pulled out my phone, and saw a bunch of new messages. Right as I got my earbuds out, Brian sat down next to me. Jason had told him about the stuff on my phone, and Brian wanted in on it too.

Mom and Jason had sent a few video clips, although they only went from around 10 to 60 seconds each, with the promise of seeing the full vids later. It didn't matter that they were short, I was so happy to have them.

The first clip showed Mom giving Jason a blowjob. She was going at it really hard, and his cock was really shiny and slick with her spit. I didn't care that it was only 20 seconds; in that moment, it was the hottest thing I'd ever seen! I… I admit that when I saw it, I was so overwhelmed that I came in my pants. It didn't feel very satisfying because of the cage, but it helped a little bit. I told Jason that the BJ clip was so good I creamed my pants, which felt extra humiliating.

The other couple clips were good, and got me kinda horny again. The next one showed Jason cumming onto Mom's face. There was a short clip showing the end of a footjob Mom had given him, ending with him cumming on her feet. The last two clips they sent showed Jason fucking Mom from behind. In the first one, Jason was fucking her really hard, and Mom was moaning like crazy. The second clip started right as he came inside her, and then showed some of his cum dripping out once he pulled out of her.

The last two periods of the day felt like torture. I could barely focus. I kept looking at the clock and sneaking peeks at my phone, but Mom and Jason didn't send anything. I was so out of it that I nearly missed getting called on in one of my classes. I thought about ditching class and heading straight home, although I'm sure Mom would have punished me for that…

After school finally ended, I raced home. I couldn't wait to see Mom and Jason in person.

When I got home, I didn't see anyone around at first. After going inside, however, I heard some loud noises coming from my bedroom. They were obviously having really loud sex inside, but the door was locked, so all I could do was knock and wait patiently outside.

Eventually, they finished, and after a few minutes, Jason opened the door. He and Mom were both fully clothed, and he said he was going to leave! It felt so unfair, I really wanted to watch! I was disappointed, but I figured at least I'd get to watch the full videos. However, Mom said that since I'd already cum today, there wasn't any need for that, and that I could see them after the cage was off.

At least there weren't any interruptions for my homework, although I still couldn't concentrate on anything else.

Tomorrow is the last day of this before I'm unlocked. I can't wait, it feels like it's been forever!

Day 5: Friday

I'm almost free! After I finish writing this, Mom's gonna unlock me. I'm so fucking ready for this.

Before I left for school, Mom said to go home with Jason to Naomi's place, and that we'd meet there. I was thinking about that all day! It wasn't as bad as yesterday, and she didn't send me anything (probably so that I'd pay more attention at school), but it was still very distracting. The school day went by sooo slowly . I didn't pay a ton of attention in class today, either. I really wanted school to be over so I could go to Naomi's place.

Eventually, after what felt like forever , school was over, and we all got to go home. I walked to Naomi's place with Jason and Brian. All three of us were stoked. Pretty sure they were hard the whole way home. I wanted to be, but, y'know, cage. I hoped that once we got there, Mom would unlock me, and that would be the end of my week in chastity. I thought it would suck not being able to join in, and that Mom wouldn't be that cruel.

Turns out I was actually very wrong.

When we got there, Mom, Naomi, and Emily were in the living room. Jeremy, Emily, and Jake had gotten home before us, and they'd brought their friends. Naomi and Emily were both getting fucked on the floor in their collars, but Mom was sitting on the couch looking cool as ever. She had the usual black lacey lingerie she wore whenever she went to 'party' at Naomi's place. She was wearing the key to my chastity cage on an anklet.

I asked if she would unlock me, but she said "not yet". Mom said I had to sit out the initial 'wave' to be on cleanup duty for her. When someone came in or on her, I had to clean up the cum to get her ready for the next boy. With my mouth. Once everyone had a turn and there was a lull in the action, she said she'd unlock me.

I knew she might have made me do something like this. I prepared myself. It was so humiliating, but in kind of a hot way, so it wouldn't be too bad, I guess. I'd never eaten cum before, but I figured it couldn't be that bad.

We started by taking our clothes off. The other boys were all naked, but I still had my little cage on, as a pretty stark reminder of all the action I wasn't getting. I was leaking pre out of it, and I was super hard. I couldn't wait to be unlocked.

A bunch of boys were interested in Mom, and she had to take on several at once to keep up with demand. They practically swarmed her, and she had one in each hole really quickly. All I could do was sit quietly and watch, tugging uselessly at my little cage. I felt really anxious as I waited for the first one to cum.

I wasn't sure how long it took, but eventually, the first boy came. Specifically, he came up her ass. Once he was done, he called me over and spread her cheeks apart. I took a deep breath, and buried my face in Mom's asshole. I nervously probed my tongue inside her butt, licking out cum as she squeezed and pushed it out. Only a few inches below, her pussy was getting fucked, and I realized I'd have to clean out that hole too.

It was, as I expected, really emasculating. Feeling the cum fill my mouth, tasting it on my tongue, and then feeling it slide down my throat when I swallowed, it was all really fucking humiliating, and it turned me on so much. The actual taste wasn't too bad. Kinda salty, left a weird feeling in my throat.

After I finished cleaning her ass, someone else came by and started fucking it. Jason and Brian cheered for me and called me a "champ". After getting the first time out of the way, it wasn't so bad, and I was looking forward to the next one.

Good thing I got so into it, too, because holy shit did everyone have a lot of energy. I kept count: I ended up eating 2 more loads of cum out of her ass, 3 loads off her butt, 4 loads out of her pussy, 3 loads off her face, 2 loads off her tits, and 1 load off her feet. That's sixteen loads people pumped into or onto Mom, and sixteen loads of cum I ended up cleaning off her and swallowing. I'm kinda surprised I'm not feeling full from it. Maybe I could go for more…

Well, whatever, I'm done for now. Mom's gonna unlock me, and I'm gonna fuck her face so hard when I'm free!

…Not gonna lie, I wouldn't mind doing this again sometime, though, despite all my complaining.

Notes:

Hey everyone! I tried for a journal format this time around, I hope you all like it!
It's been a while, huh? Nearly 2 months to the day since I posted my last story! I'm sorry I left you all hanging for so long, I feel you deserve an explanation.
The short version is that I decided to work on two other stories before starting the next chapter of my current ongoing project (y'know, the stuff I work on when not writing this), which I expected to be short but each one ended up taking much longer to write than I expected (that's also sorta true of this one, but not nearly to the same degree). Also, between global news, my own personal anxiety, and Elden Ring, I wasn't as productive as I normally am.
To compensate for the long wait, I have another story that I'm going to start working on right after I post this one. Hopefully this little double-feature will tide you all over and make up for the long delay.
Stay safe,
Chronicler

Chapter 8: Le Petite Morte d'Jake

Summary:

Jake shows off a little project he's been working on: A quest to bang every slut he knows up the butt.

Notes:

(See the end of the chapter for notes.)

Chapter Text

Session Start

[13:00] JakeTheSnek Heya!

[13:00] JakeTheSnek It's Jake, if that wasn't clear

[13:02] TheFool I never took you for a pro wrestling fan

[13:03] JakeTheSnek wait wut

[13:04] TheFool There used to be a wrestler named Jake "The Snake" Roberts, he wrestled for the WWF

[13:05] TheFool They're the WWE now, they had to change it after the World Wildlife Foundation threatened to sue

[13:05] JakeTheSnek REALLY?! LMAO THATS AMAZING

[13:06] TheFool Yeah, it was a wild thing

[13:07] TheFool Jake The Snake used to enter the ring with actual snakes, it was pretty awesome. He'd come out with a big ol' python hanging around him

[13:08] JakeTheSnek I dont think Mom will let me get a python D:

[13:09] TheFool Really? I thought she let you show your 'python' off pretty frequently around the house

[13:09] JakeTheSnek No, she hates snakes

[13:10] TheFool That's not what I hear…

[13:10] JakeTheSnek OH YOU MEAN PENISES!

[13:11] TheFool …yes, lmao

[13:12] JakeTheSnek My dong cant bite tho..

[13:12] JakeTheSnek i dont think it hisses, either

[13:13] TheFool If it does that, you should see a doctor

[13:14] TheFool So is Naomi taking good care of your python?

[13:14] JakeTheSnek yeah o: its been pretty busy

[13:15] TheFool Where is she, anyway?

[13:16] JakeTheSnek idk, kitchen, i think?

[13:17] TheFool Tell her I said hi

[13:17] JakeTheSnek will do!

[13:19] JakeTheSnek oh! I completed my little collection recently o:

[13:20] TheFool Oh? What do you collect? Stamps? Does anyone still collect stamps?

[13:20] -JakeTheSnek- sent

The image shows a collage of butts, each freshly fucked with some cum dripping out of them. Each one has a label, indicating the butt's owner. There are 9 in total: "Mom", "Emily", "Megan", "Juli", "Tanya", "Jamie", "Henry", "Claire", "Sai". They all seem to have been taken in different rooms with different lighting, probably on different days, with the butts' owners in different states of undress.

The one labeled "Tanya" appears to be outside somewhere, and Tanya herself has a hiked up blue dress and lowered panties.

The one's labeled "Jamie" and "Henry" appear to be in the same room, on the same bed. Jamie is totally nude, while Henry is wearing a pair of black nylon stockings, heels, and a blonde wig.

The others seem to have been taken either at Megan's or Naomi's house.

[13:22] TheFool Woah! That's really impressive, congrats! Are those all your handiwork?

[13:23] JakeTheSnek thanks! And yeah, I did all those ;D

[13:24] TheFool It's like a quilt, each image tells a story

[13:24] JakeTheSnek heh, i guess some of them do

[13:25] JakeTheSnek I have video clips i took for some of them! Those tell a story better cause they have sound ;p

[13:26] TheFool Should I expect to see your work at the next Oscars?

[13:26] JakeTheSnek I dont think so, but never say never!

[13:27] JakeTheSnek I think the Tanya one is my favorite! Bumped into her totally on accident

[13:28] -JakeTheSnek- sent 4

The video seems to start mid-conversation, and shows Tanya standing in what looks like a parking lot on a sunny day while wearing a purple sundress and holding her purse.

Tanya: …that's kinda- [Suddenly notices the camera] Oh, are you recording this? I thought you just wanted a picture after.

Jake: [From behind camera] Heck yeah!

Tanya: I mean, more power to ya, but I don't know if there's really a good spot around here. [She looks around] Don't wanna get your hopes up-

The video suddenly cuts to a first person shot behind Tanya, who is pressed up against a wall with her dress hiked up. Jake is rapidly thrusting into her ass, causing a loud "Plap-plap-plap" noise. Both Tanya and Jake are doing their best to be quiet. After showing this for around 10 seconds, the video ends.

[13:30] TheFool Damn, that was impressive. I like the hard cut, lmao

[13:30] JakeTheSnek thx! I thought it was funny, heh ;P

[13:31] TheFool What spot did you find, if you don't mind me asking? I'm curious now

[13:32] JakeTheSnek uh, like, next to a dumpster. It didnt really smell so it wasnt a mood killer, and it was pretty out of the way

[13:33] TheFool Don't they usually put cameras near dumpsters to stop people from illegally dumping?

[13:34] JakeTheSnek do they? Dad throws stuff in dumpsters all the time, he just says we have to be fast…

[13:35] TheFool …Your dad is a braver man than I. Maybe California is just really lax about that stuff.

[13:36] JakeTheSnek I have another video! If u wanna seeee o:

[13:37] TheFool I'm always willing to see what you have to share!

[13:38] -JakeTheSnek- sent 4

The video opens in a well-lit bedroom. Jamie, a 5'3" girl with pale skin, dyed black hair, and blue eyes, sits completely nude on the edge of the bed. Jake stands just off to the side, also undressed. Jamie turns to address the camera.

Jamie: Babe, you ready to record?

Henry: [From behind camera] Ready, mistress.

Jamie: Good boy! I'll do the same for you when it's your turn. [She turns to face Jake] How bout you, stud? You ready? [She looks at his erect cock] You look ready!

Jake: Heck yeah!

The video cuts to a shot showing Jamie and Jake from the side. He's fucking her doggystyle, thrusting into her quickly with youthful vigor. Jamie moans loudly as she gets fucked. The camera moves closer and shows a closeup of Jake's cock pounding her asshole.

Jake: [From offscreen] Damn, your girlfriend has a tight ass!

Henry: [From behind camera] Does she? It's been a while…

Jake: Yeah? When did you fuck this ass last?

Henry: Uh… I think like 6 months ago.

Jamie: 8 months!

Jake: Dang, I don't think I could go that long…

Henry: Guess I know what I'm asking for when I get uncaged next. Just a few more weeks.

The video cuts a final time, showing cum leaking out of Jamie's asshole. Jake seems to be holding the camera, since Henry's face is visible close to her butt. He's wearing a blonde wig, and with his soft features, he makes for a cute girl. He leans in and, with no hesitation, starts licking the cum off his girlfriend and eating it out of her gaping hole.

Jamie: Good boy, good boy…

[13:40] TheFool Jamie's hot, although, I don't know how I'd feel about having her boyfriend around like that.

[13:41] JakeTheSnek its weird, but its also pretty fun!

[13:41] TheFool You don't feel weird about it at all?

[13:41] JakeTheSnek Nope!

[13:42] JakeTheSnek fun stuff is fun! Juli says its only weird if you make it weird

[13:42] TheFool I suppose you have a point there

[13:43] -JakeTheSnek- sent 4

The video opens in the same bedroom as before, except with Henry sitting on the edge of the bed, still in the same wig. He's wearing the same nylon stockings and heels as in his picture from the collage, and there's a tiny metal chastity cage on his cock. Jake's sitting next to him, also nude.

Jamie: [From behind camera] Ya ready, babe?

Henry: Yes, mistress.

Jamie: Yeah? Gonna be a good boy for me and Jake?

Henry: Yes, mistress.

Jamie: Ugh, you're no fun to bully! You could resist a little .

Henry: Oh, sorry. Uh, I mean, totally, grr, how could you do this to me, et cetera.

Jamie: Jake, you buyin' this?

Jake: Nope! Sorry, Henry, you're too much of a slut to be convincing.

Henry: Heh, thank you.

The video cuts to a closeup of Jake fucking Henry. Jake has a firm grip on Henry's hips, and is slamming into him at a hard but steady pace. Henry lets out quiet moans and groans as he gets fucked. The camera zooms out to show Henry on his hands and knees, and then zooms over to his face.

Jamie: He's good, isn't he, babe?

Henry: Yes, mistress.

Jamie: You like gettin' fucked by boys half your age?

Henry: Yes, mistress.

Jamie: Me too! So young and yet he's already way better at this than you ever were.

Henry: Yes, mistress, I serve better as a slut.

Jamie: Good boy!

The video cuts again, showing a closeup of Henry's chastity cage, which rocks back and forth as Jake fucks him. Henry's quiet groans are drowned out by the wet slapping of colliding skin. Suddenly, the cage starts twitching, and cum starts leaking out of it. It drips and oozes onto the bed below in long, sticky strands. After maybe ten seconds have passed, and a few strands have fallen, the twitching stops.

The video cuts a final time, showing Jake thrusting rapidly into Henry's ass. Jake suddenly plunged deep into Henry, grunting as he empties his balls. Jake pulls out, and the camera zooms in to show Henry's open asshole leaking Jake's cum.

[13:47] TheFool Woah, good job there!

[13:47] TheFool …You know, I'm starting to see the appeal of this whole cuck and crossdressing thing…

[13:48] JakeTheSnek heck yeah! And yeah, maybe I'll see if Jamie or Henry wants to chat sometime. They know a little about you lmao

[13:48] JakeTheSnek they make a great case for their kinks ;D

[13:49] TheFool I have to admit I'm kinda looking forward to it

[13:50] JakeTheSnek Okay I think im gonna head out for now, I wanna go find Mom cause sending you this stuff got me hard again lmao

[13:51] TheFool Have fun, tell her I said hi!

[13:51] JakeTheSnek will do! Bye!

Session Close

Notes:

Thanks for sticking with me, everyone! This took a little more time than I would have liked (Elden Ring has *really* eaten into my productivity lmao, but I think I'm finished with it). Hope this helps make up for the long wait~ Not sure when the next story will be, but hopefully I won't keep you waiting *too* long

Chapter 9: Short and Sweet Release

Summary:

While in the middle of her Sunday chores, Naomi is summoned by her kids to the living room, and finds some unexpected guests have arrived hoping to borrow her for a short (very short) while.

Notes:

(See the end of the chapter for notes.)

Chapter Text

It was just before noon on Sunday, and Naomi's day had been progressing routinely. She'd woken up, made breakfast, drained her sons' balls, and had started on the household tasks that needed doing. Naomi was in the middle of putting away some freshly dried towels in one of the bathrooms when she heard someone approaching.

"Hey, Mom." Jake, her youngest son, said, poking his head through the door. "Come to the living room. Won't take long."

"Of course, dear." Naomi replied. "May I finish this first?"

"Yeah, that's fine." Jake answered, before abruptly leaving.

Naomi took a few minutes to finish putting away her towels, then quickly made her way to the living room. Odd that he didn't just want a quickie in the bathroom. She thought to herself. Oh well, as my sons wish, I shall obey. As she got closer, it sounded like they had a video game on the TV, and she could hear what sounded like Emily moaning.

There was a little bit of surprise when Naomi got to the living room. As she walked in, she saw her daughter, Emily, on her hands and knees on the floor getting fucked by her older brother, Jason. Emily looked pretty nonplussed about it, messaging her friends on her phone as she got railed. Emily's twin brother, Jeremy, was sitting on the couch playing a video game, with Jake sitting next to him providing advice.

This, however, was all normal. What was out of place was that two family friends, Jamie and Henry, a young couple in their early 20s, were sitting on another couch. The two of them waved at Naomi as she entered the room. Jamie was the only girl in the room, or indeed the entire house, wearing clothes and not wearing a collar.

"Hey, Naomi!" Jamie said, giving a little wave.

"Hiya." Henry said, a little meekly.

"Hello, both of you." Naomi said. "I didn't know you were coming over today. To what do I owe the pleasure?"

"Henry's due for his once-a-month release." Jamie said. Naomi nodded. Henry wore a chastity cage full time, but Jamie let him out once a month for precisely one no-strings-attached orgasm doing whatever he wanted. It was an arrangement that both of them enjoyed. "He wanted to spend it with you this time around. I asked your kids, they said it was fine if I borrowed you for a bit."

"We did, it's true!" Jake chimed in.

"Of course, so long as my masters approve." Naomi said with a little chuckle.

"Don't worry, he doesn't last all that long anymore." Jamie said. Henry blushed a little and averted his gaze. "Right, babe?"

"Y-yes, Mistress." Henry answered.

"Very well." Naomi said. "How would you like to have me, Henry?"

"I, um, y'know, doggystyle, seems like the most popular thing around here." Henry answered, glancing over at Emily and Jason, who were still going at it.

"It certainly seems like the house specialty, haha." Naomi chuckled. She made her way next to Emily, and got down on her hands and knees. As she did so, Henry quickly stripped his clothes off. Jamie unfastened the anklet she was wearing, which is where she kept the key to her boyfriend's chastity cage. With a swift, practiced motion, she took off the small cage, freeing Henry's cock for the first time in a month. He'd already been straining against his cage with anticipation, although it took him a little bit to get fully hard.

"Hey, Mom." Emily said breathily between moans. She rocked a little back and forth as she got fucked.

"How are you, Emily?" Naomi asked.

"Been worse." Emily answered.

Once he'd gotten hard, Henry approached Naomi from behind. He was already leaking precum, and throbbing with anticipation. Jason looked over at him.

"Hey, man, weird seein' you on this side for once." Jason said, without breaking his rhythm as he fucked his sister.

"Guess it is, huh?" Henry replied. He placed his hands on Naomi's hips, and after taking a second to line up, he thrust inside her. He fucked her frantically, eagerly, like a man lost in the desert chugging the first bottle of water he'd come across in days. Naomi moaned as she rocked with his movement. He may not have been particularly big, but there was a desperate neediness to his thrusting that Naomi enjoyed.

Sadly, he did not have the stamina to back it up. The anticipation and buildup always made him sensitive, and gave his cock a hair-trigger. Always he tried to savor it, and always he failed spectacularly. A small wave of disappointment and despair washed over him as he approached orgasm, having lasted, at most, a minute, and not being able to indulge in anything like it again for another month.

"No… shit…" Henry groaned under his breath as he came. He unloaded a month's worth of cum into Naomi's pussy. He throbbed intensely as a powerful orgasm hit him like a truck. His whole body shook and twitched as he grunted and emptied his balls.

"Damn, that was fast." Jason remarked.

"Better luck next time, dude." Emily quipped.

"Not likely." Jamie said. "You all done, babe?"

"I, um, yes, mistress…" Henry answered meekly, pulling his rapidly softening dick out of Naomi. He sat down next to Jamie, who started to put his chastity cage back on.

"Thanks for letting me borrow your mom." Jamie said as she finished locking Henry's cock back up.

"Anytime." Jake said.

"Always happy to be of service." Naomi said as she stood up.

"Sure you don't wanna stick around, Jamie?" Jeremy asked.

"Would love to, but we got stuff to do." Jamie answered. "Next time, though!"

After a few short goodbyes, Jamie and Henry left, and Naomi went back to attending to the laundry.

Notes:

Hey everyone! I've been juggling a bunch of longer projects lately, so you might see Collared Mom updates slow down for a bit while I work through all my other story ideas.
People seem very fond of Henry and femboys/chastity in general. Do you all want to see more of him? I have some ideas, but lemme know what you think~

Chapter 10: Boys' Night In

Summary:

Naomi and her husband have a social function to attend. By happy coincidence, their friend Jamie has a date planned that night, and her femboy cuck boyfriend, Henry, can watch over Naomi's kids. Will they be good kids and listen to their babysitter, or will they fuck his brains out instead?

Notes:

(See the end of the chapter for notes.)

Chapter Text

"You kids be on your best behavior and listen to Henry." Naomi said, standing alongside her husband near the front door. She was wearing an elegant black dress. Frank, her husband, had a nice suit on. The two of them were about to leave for a work event Frank had to attend.

"Don't give Henry too much trouble now." Frank added.

"Yes, Dad." Jason, Jeremy, Emily, and Jake all said in unison.

"That's uncanny." Frank noted, eyeing them suspiciously. "You rehearsed that, didn't you? Well, anyway, your mother and I will be back in a few hours."

"Now, Henry," Jamie said, standing a few feet from Frank and Naomi, "you be on your best behavior and listen to those boys, got it?"

"Yes, Mistress." Henry answered. He seemed dress more to serve rather than lead. He wore a red wig, a black blouse with a red checkered miniskirt, black stirrup leggings, and a pair of 5 inch high heeled sandals that showed off his bright red nail polish.

"Good boy!" Jamie replied. She leaned over and gave him a quick kiss. "I'll let you know how my date's going, okay? You have fun!"

Jamie, Naomi, and Frank all left. There was an awkward silence in the house as the occupants listened to the sound of receding footsteps, followed by the sounds of cars starting and then driving away. Those left in the house made their way to the living room. Jake and Jason sat on either end of the larger couch, with Henry in between them. Emily and Jeremy sat on the smaller sofa.

"I don't think we've ever hung out just with you, Henry." Jason, Naomi's oldest, noted.

"I guess you haven't, huh?" Henry said. "Me and Jamie usually come as a package deal."

"Since it's just us, we could do, like, Guy Stuff!" Jake suggested. "Emily can do Guy Stuff too if she wants."

"I'm not really dressed for particularly masculine activities, if you hadn't noticed." Henry said with a dry smile. "But, y'know, we can do pretty much whatever."

"You're still wearing your thing, right?" Emily asked. "Don't you wanna take it off?"

"My cage?" Henry asked. He lifted up his skirt, showing off a metal chastity cage locked firmly around his cock. He wasn't wearing anything else under his skirt. "I mean, honestly, sometimes, but I really like what I have with Jamie."

"Imagine all the pussy you could be getting without it, though!" Jake said.

"I, uh, don't really need to imagine very hard." Henry replied. "I used to be pretty active before I was caged full-time." His cock tried to get hard as he recalled the memories; he strained futilely against his cage, with the pain only serving to remind him of the things he couldn't do anymore.

"Woah, really?" Jeremy asked.

"Yeah. Used to just be, like, another guy who'd show up to Megan's place to get my rocks off. When I started wearing it, it was usually only for some of Megan's weekend parties." Henry explained. "They used to let me out after, too, and I got to do stuff with the girls once I was out. Then I tried wearing it for longer and, uh, now here we are."

"I don't think I could give that up." Jeremy said.

"Maybe he liked hanging around sluts like Megan because he wanted to be a slut." Jason suggested.

"That's not inaccurate." Henry said. "Being a slut is definitely fun, if you're into it."

"I'd like to get into some sluts." Jake said. "Although we only really have the one slut, since Emily isn't wearing her collar."

"Is that my cue, then?" Henry asked. He sat up and repositioned himself on the couch to lay on his side, exposing his butt to Jake. It also, rather conveniently, placed his head near Jason's lap.

"I hadn't really decided, but now I have! And it was." Jake said. The three boys stood up and quickly started to shimmy out of their clothes.

"Oh, hang on, I'll be back in a bit." Emily said. She stood up and headed upstairs while the others undressed.

"Mom and Dad left money for delivery, right?" Jeremy asked. Jason and Jake sat back down on the couch once they were completely nude.

"They did, yeah." Henry answered. "I guess I could try cooking if you real- " He was interrupted as Jason grabbed him by the head. "Guess we'll ta-" He was cut off as Jason stuck his cock into Henry's mouth. Instinct kicked in, and Henry began sucking on it eagerly.

"Cooking would leave you with less time for other things." Jason said.

"Like video games!" Jake added as he sidled up behind Henry. Once he was in position, he pressed the tip of his cock against Henry's ass, and thrust inside. "Jamie always preps you so well. It's cute!" Henry let out a muffled moan against Jason's dick.

"You wanna join in, bro?" Jason asked.

"Nah, I'll wait for an open hole." Jeremy answered.

Jason and Jake quickly got into a steady rhythm with Henry. Jake kept up a rapid pace, filling the room with loud, satisfying slapping sounds as he thrust into Henry's tight hole. Henry moaned quietly as he got fucked, doing his best to focus on sucking the cock in his mouth. It was slick and shiny with his saliva. He strained in his cage from the excitement of it all, twitching uselessly as he dribbled precum out of it.

After a couple minutes, Emily came back down the stairs, totally nude but wearing a large, bumpy strapon. Her brothers shot her curious looks.

"Finally gonna get to use this on someone other than Mom." Emily said, proudly showing off the toy.

"You could probably use it on Megan if you asked." Jeremy, her twin brother, pointed out.

"Yeah, but I wanna use it on a guy!" Emily protested. "Megan and Jamie say it's a lot of fun!"

"I think I'm almost done for now." Jake said with a groan. "You can have your turn soon!"

"Yeah, me too, actually…" Jason added.

Jake and Jason managed to pump cum into Henry from both ends at the same time. Henry obediently swallowed every drop of Jason's cum as he felt Jake spurt a hot load inside his gut. Jake quickly pulled out, leaving Henry's hole with a small gape as cum dribbled out of it.

"Hey Jer," Emily said, turning to her brother, "you think Henry can fit both of us in one hole at the same time?"

"My record back there is three, although the positioning is kinda hard." Henry said. "Also, uh, maybe get some more lube, please. Absolutely can do, though."

"I was expecting you to be more hesitant." Emily said as she picked up a bottle of lube.

"I get that a lot." Henry replied. "Jamie says it makes me no fun to bully."

"Maybe that just means we need to bully you harder." Jeremy said.

"Jamie says the same thing." Henry said. "Although, and no offense, she's meaner than any of you."

"Oh yeah?" Emily asked. "We'll see about that!"

Jeremy sat down on the couch, and Henry straddled his lap so that they were facing each other. Henry lowered himself onto Jeremy's cock, and it slid in easily. Emily came up behind him, and after applying a little extra lube to the toy, pressed the tip of the dildo against the edge of Henry's hole. After giving it a little bit of a push, it slid inside him alongside Jeremy's cock.

"Holy fuck!" Henry groaned as his asshole stretched to accommodate both twins. Even with the extra lube, it was an intense feeling. He could feel the cock and the toy sliding against each other inside him as Emily and Jeremy got into a rhythm.

Henry could only take a few seconds of it before he came. He made a pained groan as he bucked his hips, feeling the cage bite into his cock as he tried his best to cum. The pink head was visibly straining against the tight metal enclosure; the entire cage twitched as his cum oozed out of it.

"You're gettin' jizz on me." Jeremy noted, although he didn't sound particularly annoyed.

"S-s-sorry…" Henry mewled. "Oh my God…" His whole body shuddered as the orgasm started to fade.

"We break you already?" Emily asked.

"N-no, I can take more." Henry answered.

"This is actually pretty intense." Jeremy said, grunting a little as he spoke. "There's… kinda a lot… goin' on."

Jeremy lasted a few minutes more, but the intensity of feeling his cock rub against a textured toy inside a tight hole eventually won out. The intensity got worse as he came; Emily kept hammering away at Henry's ass, providing more sensation than Jeremy thought he could handle. He grabbed Henry's hips for dear life as he shot cum into the tight hole, his orgasm prolonged by the dildo rubbing against him. He involuntarily shuddered from the overstimulation, and pulled out at the first opportunity.

Emily eventually got tired. She wasn't quite used to being the one doing the thrusting. After vowing to get in more practice, she pulled out of him and took the dildo off.

Nobody bothered to put their clothes back on. The kids started up their game console and took turns playing games for a while, occasionally taking a break to pump a load in their femboy babysitter.

"I think you run away for the first two, then dodge into it for the third." Jake said as his sister died to a boss.

"I mean, you have to already be a few feet away before she even starts it, it's kinda bullshit." Jeremy added.

"A frozen pot will interrupt her." Henry offered. "Just gotta hit her with it when she starts the telegraph."

"Oh, do we have that recipe?" Jason asked as Emily handed him the controller.

"It's not hard to find." Henry explained. He idly grabbed his phone when he heard a notification go off. "The ingredients are- Oh, hey, text from Jamie."

"Ooo, how's her date going?" Emily asked.

"She sent a video and not a cry for help, so probably well." Henry replied. The video thumbnail showed the interior of someone's living room, although he didn't recognize it.

As the video started, he could hear moaning from off-camera. Familiar moaning. The camera panned over, showing Jamie, half-clothed, bouncing on someone's dick on a couch. Henry didn't recognize the guy she was with.

"Does your boyfriend know what you're up to?" A woman's voice asked from behind the camera. Henry recognized it as Jamie's best friend, Juli.

"I told him I was just going on a date." Jamie answered as she continued riding the guy she was with. "Which is kinda true!"

"Partying it up with me hardly counts as 'a date'." Juli said. She briefly panned over to a group of guys who looked like they were recharging. Henry counted at least six.

"Sorry, babe." Jamie said. She blew a kiss into the camera. "Hope you're not mad!" He wasn't. He was painfully hard again in his little cage.

"Can't believe you've left him all by himself just to get some dick." Juli said, playfully chiding her friend.

"Hey, he's not alone!" Jamie protested.

"Oh yeah, you saddled him with watching Naomi's kids." Juli replied. "You're evil ."

"I know." Jamie said. She gave a loud, exaggerated moan as she briefly picked up her pace. Then, she gave a quick look into the camera. "And I know you love it." She said with a sly wink, before the video ended there.

"Damn, you're right, she is mean." Emily said.

"Told you." Henry said. "Now I'm horny again, goddammit…"

"Me too, that was hot." Emily replied.

"Well, you've got me for the whole night." Henry said. "Your wish is my command~"

Notes:

Wow, 10 whole entries in Stories of a Collared Mom! This is technically the 12th story if you count the first two, but I think it's still worth celebrating!
Thank you to all my readers for sticking with me, your support means a lot~

Chapter 11: Emily On Top

Summary:

After getting just a little tired of her brothers' shenanigans, Emily decides to blow off a little steam with her parents.

Chapter Text

Emily lay on the couch, panting heavily. She was sweaty and sticky with cum. She'd come down from her room for something , and made the mistake of going through the living room. Her brothers decided to run a train on her, and since she'd been wearing her collar, she'd had no choice but to comply. She didn't even remember what she'd come out for by the time they were finished.

"Alright, I need a break." Emily said as she undid her collar.

"Aw, alright." Jeremy, her twin, replied.

Emily got off the couch and stood up, holding her collar in her hand. Feeling vaguely lost and unsure of what else to do, she decided to go look for her mother. She decided to check her parents' bedroom first; even if Naomi wasn't there, Emily could still use their shower to clean herself up.

"Hey, Mom." Emily said as she walked into her parents' room. Naomi was lying on her bed, totally nude save for her collar, reading a book. It sounded like the shower was running in the adjacent bathroom; Emily guessed her father was in there.

"Hello, dear." Naomi replied. She closed her book and set it down on the nightstand. "Do you need something, Emily? Or did your brothers send for me?"

"The first one." Emily answered. She set her collar down on the nightstand and climbed on the bed.

"The boys make a mess of you again?" Naomi asked.

"Yeah, pretty much." Emily replied as she straddled her mother's face. "So now you get to clean me up."

"Of course, dear." Naomi replied, looking up at her daughter. Emily lowered herself onto Naomi's face, and Naomi dutifully opened her mouth, sticking her tongue out into her daughter's slit, eliciting a moan from Emily. Emily grabbed Naomi by the head and started riding her mom's face, occasionally bumping her clit against Naomi's nose. Naomi sucked on Emily's pussy as she tongue-fucked her daughter, feeling her sons' cum flow into her mouth. It was still fresh and warm, and Naomi swallowed it obediently.

"Fuuuuuck!" Emily moaned. "You're so good with your mouth, Mom." Naomi would have smiled if her mouth wasn't busy. She prided herself on how well she served her children.

It didn't take too long for Naomi to clean up all the cum out of Emily. Emily, however, wasn't quite done. She continued riding her mom's face, moaning loudly as she did so. She was already wet again, and Naomi's face was covered in her juices.

"Heya, Em." Frank, her dad, called out as he emerged from the bathroom, still naked and mostly dried off. "I'm not interrupting, am I?"

"No, Master." Emily replied.

"You don't have to call me that if your collar's not on, Em." Frank said.

"Put it on me, then." Emily suggested, pointing to her discarded collar on the nightstand.

"Well, if you insist." Frank replied. He walked over to the side of the bed and picked the collar up off the nightstand. Emily stopped moving as her father fastened the collar back around her neck.

"Thank you, Master." Emily said. She leaned over and kissed the tip of his cock.

"In the mood to ride, are you?" Frank asked. He walked around to the other side of the bed and climbed in, laying down next to Naomi and Emily.

"Yes, Master." Emily answered.

"Good, then come over and hop on." Frank ordered, patting his lap.

"Hell yeah!" Emily said as she climbed off Naomi. "I mean, uh, yes, Master."

"'Hell yeah, Master' has kind of a weird ring to it." Frank said. "It suits you, though."

"You think so, Master?" Emily asked as she climbed on top of her father's lap. She reached down and grabbed Frank's cock by the base, lining it up with her pussy before lowering herself onto it. Despite how wet she was, it was still a bit of a tight fit. " Fuck , you're so big, Master!"

"I'm just bigger than your brothers." Frank said.

"Don't sell yourself short, Master." Naomi chimed in, rolling over to snuggle up against Frank's side. "You're certainly above average."

"I suppose you'd know, you have quite the experience now." Frank replied, turning over to look at her. Naomi smiled back at him. "Of course, she's also tighter than you."

"Hell yeah I am!" Emily declared. She'd quickly gotten into a steady rhythm, bouncing up and down on her master's cock. She let out high-pitched moans as she rode him, and her tits bounced along with her. "Cause I'm not as big a whore."

"For now." Naomi said. She leaned over and gave Frank a quick kiss. Her lips tasted like Emily's pussy. "Although, I recall you being rather busy yesterday when you kids visited Rag."

"Hey, I didn't invite all those people over!" Emily protested.

"You seemed like you were having a good time, though." Frank said.

"Yeah, alright, it was fun." Emily admitted. She suddenly came to a stop; her body was covered in sweat, she was panting hard, and she had a vaguely pained look on her face. "Actually, still kinda sore. Uh, permission to do something else, Master?"

"Sure." Frank said. "Get a strapon and help me spitroast your mom."

"Sure thing, Master!" Emily said enthusiastically. She leapt off the bed and checked the closet

"Oh, fun." Naomi said. "How would you like to have me, Master?"

"Get on your back and open wide." Frank ordered.

"Of course, Master." Naomi said. Naomi repositioned herself so that she was laying on her back, with her head hanging off the edge of the bed.

"Good girl." Frank said as he made his way to her upside-down head. He pressed the tip of his cock to her lips.

"Thank you, Mas-" Naomi started, before her husband thrust into her mouth. Naomi opened her mouth wide, and he slid easily into her throat. She reached up and clung tight to him, and he wasted no time in going to town on her throat. A loud, wet "glug glug" noise came from Naomi's mouth, and her own saliva started to flow down her master's cock and drip onto her face.

As soon as Frank paused to give Naomi a quick break for air, Emily came back with a strapon equipped. Naomi dutifully spread her legs for her daughter. Emily got on top of Naomi and lined the tip of her toy up against Naomi's slit. She and her father both thrust into her at the same time, eliciting a muffled moan from Naomi.

Frank and Emily were merciless. Emily had quite a bit of pent-up aggression to work out, and she fucked her mom just as fast and hard as any of her brothers could. She could see the ripples in Naomi's body as she fucked her mom. In spite of this, Naomi didn't lose much of her concentration for taking her master's cock in her mouth. Even as she ran out of air and needed more, Naomi always thought about how her master's cock felt.

When he was finally done, Frank thrust deep into Naomi's throat. She felt his entire dick pulse inside her mouth, and felt his hot, sticky seed land in the back of her throat. Naomi made sure to swallow, so that the muscles would massage just a few more drops of cum out of her master's shaft.

"Alright, I'm good." Frank said as he pulled out of his wife's mouth. "Although maybe I need another shower to wash all that off."

"Thank… you… Master…" Naomi panted. Emily was still fucking her, even as she tried to catch her breath.

"Still going strong, Em?" Frank asked.

"Actually, a shower sounds good about now." Emily said. She and her mom had both cum a few times already; the strapon was quite wet in more than a few places. Emily stopped and started taking off the toy.

"I suppose I could use some cleanup as well." Naomi said.

"You two have fun in the shower, then." Frank said. "I'll go tell the boys you're both busy."

"Thank you, Master." Naomi and Emily said in unison.

Chapter 12: Naomi Gets Soaked

Summary:

[Contains Watersports]
A short little story about Naomi being chained up in a local school bathroom.

Notes:

(See the end of the chapter for notes.)

Chapter Text

Naomi knelt on the floor of the school bathroom, with her wrists and ankles chained to a pipe behind her. As usual, she was completely nude, save for her collar and the cuffs. She'd been there all day, and the lunch break was nearly over. Despite having some initial reservations, she found herself having a surprisingly good time.

A few boys stood around her with their flies unzipped. Naomi didn't know these boys, she was pretty sure they didn't know her kids, but that didn't seem to matter. Forceful streams of warm urine came out of their cocks, coating her in their piss. Some aimed for her face, others for her tits. One aimed directly for her open mouth, and she drank it futifully in spite of the salty taste.

Naomi had been doing this all day, and she was positively soaked. Her tits, her face, and especially her hair, had all been drenched in piss for hours, and it was the only thing she'd been able to taste since starting. The boys at school had used her as a urinal all day, although things were much busier during lunch. It was humiliating, and Naomi loved every second of it.

As a few of the boys finished, new ones approached, and Naomi spotted a familiar face: her eldest son, Jason. He waved as he approached his mother, holding a water bottle in his other hand. With her mouth not being a target at the moment, she decided to say something.

"Hello, Jason." Naomi said.

"Hey, Mom." Jason replied. "How ya doin'? I brought you some water."

"I'm doing well, thanks for asking." Naomi replied, as fresh piss rolled off her chest. "How thoughtful of you!"

"Yeah, but while I'm here…" Jason said, unzipping his pants. "Open wide, stick out your tongue."

"Of course, dear." Naomi replied. She did as she was told, sticking out her tongue conspicuously. Jason aimed right for it and let his stream loose. It hit her tongue full force, coating her taste buds before most of it flowed off the tip and onto the floor. Some of it splashed up into her mouth. As he finished, she swallowed without a moment's hesitation, her mouth tasting intensely of piss. "Thank you, sir."

"Anytime." Jason said. He opened the water bottle and tipped it into her mouth. Naomi drank deeply of it instinctively, although even with the entire bottle, the taste hadn't quite been washed out of her mouth.
"I appreciate it." Naomi said.

"Alright, gotta head to class, see you after school." Jason said, waving as he left, and yet another boy came up to take his place.

Notes:

So, uh, I've never really written anything like this before. It's not normally my jam, but the stars kind of aligned recently and I decided to give this a shot.
Please let me know what you think of it! Terrible betrayal of your trust I should never repeat? Okay execution of a good idea? Think I should do *more* watersports? Let me know!

Chapter 13: Collared Mom Mailbag Special

Summary:

Naomi and her friends and family answer questions submitted by you, the readers!

Notes:

(See the end of the chapter for notes.)

Chapter Text

Hello, everyone! Naomi here! A few of you sent in some questions for us to answer, and I thought it might be fun to make a little special of it! If you enjoy this, perhaps we'll do it again sometime! I hope you all like it. :)

Q: "For Naomi and Emily, who's the best lay in the family?"
Naomi: Don't you know it's unfair to make a mother choose between her sons? All three of my boys are perfectly good at making Mommy cum. :) Especially if they work together, haha. ;)
Emily: My brothers have strength in numbers, but Master has the most experience. He's probably the single best person at actually fucking me.

Q: "Which of the boys is horniest?"
Naomi: A little hard to say, but I think my youngest, Jake. He's quite adventurous and always willing to try new things, and he's always the most eager when other women are around and available.

Q: "For the boys, would you ever let the girls top you?"

Jason: I don't know, Emily seems like she'd be a little mean about it…

Jeremy: I'll admit I'm a little curious about it. I suppose if Emily promised not to take it too far. Mom wouldn't really go for it, though, but she might if we asked her to try…

Jake: What do you mean "would I"? I've let her do it before, it's fun! I didn't think anyone was really interested in that, though. I thought most of you were here to see us dominate the girls, but I'm totally open to the reverse if you'd like to see it!

Q: "For Sai, what's the easiest way to get you hot and bothered?"

Sai: Depends. If I already like you and trust you, a good slap across the face gets me in the mood, especially if my son is around to watch.

Q: "For Naomi, which of your sons is the easiest for you to 'deal with'?"

Naomi: Easiest to deal with? I suppose that depends on precisely what you mean. I think Jake is the best about communicating what he wants, although sometimes it takes a little work to accommodate him. Jeremy is the most considerate, always willing to let me finish something else or wait until a convenient time before he makes use of me. Jason is the least considerate, and sometimes rather unvocal; sometimes he just comes up to me and starts fucking me with no warning, and we don't say anything (until I thank him when he finishes). That makes it easiest to multitask, though, and requires the least effort on my part.

I hope that answers your question sufficiently. :)

Q: "For Sai, what's your ideal sub?"

Sai: Someone who resists a little, but is otherwise obedient. Not an outright brat, but I want to feel them chafe a little under my power. It's no fun to bully them if they don't react properly, don't you think? Like how I can sense my son Rag gets annoyed when he's locked in chastity and I'm fucking his friends (or complete strangers) merely a few feet away. He doesn't intervene or do anything about it, but he radiates a frustration I find palpable. It's very enjoyable.

Q: "For Naomi, how many boys can you suck off?"

Naomi: Haha, I'll try my best to answer. If you mean "at once", I can fit two in my mouth, although it takes a little effort and it's a bit uncomfortable for everyone involved. Looks impressive, though! If you mean in a single setting, I can do about 10 in a row before I need to give my mouth a little rest.

Q: "For Emily, how do you decide whether to put your collar on or not?"

Emily: I don't really have, like, a formal process for it. Honestly, I usually keep it on most of the time, and then take it off if I feel like I need a break or if I'm not really in a submissive mood.

Q: "For the boys, which collared girl is your favorite to play with?"

Jason: Mom! She's more naturally submissive and isn't all that feisty, so I feel like I can be rougher with her. Also she has bigger boobs.

Jeremy: I'm a little biased because Emily is my twin, but she tends to be a little more lively when we fuck her than Mom.

Jake: They're both good! They're like different flavors, and it's hard to say one is better than the other when they do different things. Sometimes I prefer Mom's obedience and "yes sir" attitude, other times I prefer Emily's more bratty, sassy style.

Q: "For Naomi, what do you always hope to be used for?"

Naomi: I'm happy as long as I'm used in a way that satisfies my boys. :) However, if you'll permit me to be a little selfish, I most enjoy getting fucked from behind. Sounds a little basic, I know, but there is something about it that makes me feel very… "used".

Q: "For Naomi, Emily, and Sai, have you ever been to a glory hole?"

Naomi: Yes, I have! I have some reservations about it, but I go when Master orders me. Sometimes he takes me, other times he'll tell me to go at a certain time and I'll record myself for him. I suspect he might send people to them when he knows I'll be there, but I can't quite confirm that, and I think that's part of the appeal. :)

Emily: I haven't. It seems like fun, but I'm a little worried about sucking off a total stranger. Don't know where they've been, y'know?

Sai: Yes, I go regularly. This might come as a surprise, but I actually quite enjoy anonymous sex with complete strangers. Illogical and dangerous, sure, but it's also hot. On a similar note, I also enjoy having meetups arranged on my behalf with people I don't know and am likely not to meet again. And if I can bring my son Rag so he can watch, that's icing on the cake.

Q: "For Jamie, how small is Henry?"

Jamie: Haven't really measured. He was pretty average back before I kept him locked up all the time, although I'm pretty sure his dick has shrunk from lack of proper use. It certainly feels smaller than it used to, although that might just be because his stamina and ability to get hard are both totally dead, and it's just kinda vestigial and useless now.

Henry: Thanks, babe, I love you, too.

Q: "For Jamie, how do you reward Henry when he's been especially good?"

Jamie: Good boys get rimjobs that end in prostate orgasms. That's about as much as I'd be willing to give him. He has no chances for an extra unlocked orgasm outside of what I already give him.

Q: "For Jamie and Henry, how much does Jamie control what Henry does? Does Henry get to make requests?"

Jamie: He's my full time sub and I can order him around whenever I want, but I also don't micromanage his life. Like, he doesn't need my permission to, say, do certain things in his free time or go to the bathroom. I do make him do non-sexual things for me (make me food, give me massages, let me use him as a footstool if you don't consider that overtly sexual). I'm 100% in control of our sex life, though.

Henry: I only get to make suggestions (usually, sometimes I'm not allowed even that), which Jamie is free to ignore. The only real "requests" I get to make are when she uncages me. At all other times, I'm pretty much at her mercy.

Q: "For Henry, what is one thing you miss about before you were caged? Is there anything about before you'd like to bring back now?"

Henry: Well, if I'm being totally honest, I do miss getting to be "one of the guys" and getting to fuck all these hot girls basically whenever I want. If we'd met Naomi before I was caged, I'd probably be making pretty frequent visits to see her. But, the fact I miss it and can't do it anymore is something I like about our current arrangement, if that makes sense? It's a very emasculating feeling, and the humiliation is something I enjoy. So missing out on it is enjoyable in its own way, if that makes sense.

Anything I'd like to bring back? Well, when I first started my… I guess what you might call "slut training" or maybe "cage training", I got to take my cage off after a party was over and do whatever I wanted with the other sluts. "The plan" was always for me to keep my cage on even after a party was over, but I did really start missing it once I was further along with my training. I've asked Jamie about maybe bringing that back again, and while she hasn't outright said it'll never happen again, she hasn't budged on it, either.

Q: "For Henry, how often do you get to fuck people who aren't Jamie?"

Henry: This is going to depend on what you mean by "fuck". I'm quite the slut, and it makes my mistress happy when I put my holes to good use. So, uh, that happens pretty frequently. Several times a week, usually.

Jamie shares me with other women if they want a subby femboy to play with. They all seem to like making me wear a strapon, and beyond the novelty of it, I'm pretty good with it.

As for actually getting to use my real cock? Well, I do get to pick whatever I want when I get my monthly release, and that includes doing things with other women. I'd say about half of them are with girls who aren't Jamie. She's teased me about limiting it, but so far hasn't actually implemented anything.

Q: "How old are each of you?"

Naomi: Quite a few of you have asked this, so I suppose you're due an answer. I'm 42, my Master is 44.

Jason. I'm 15.

Jeremy: 13, and Emily and I are twins.

Emily: Yeah, what he said!

Jake: Lucky number 11! 11 is the lucky one, right?

Sai: Isn't it rude to ask a lady her age? 38, if you must know.

Rag: I'm also 15.

Megan: I stopped having birthdays after 29. Just kidding, I'm 50 and I've still got it!

Tanya: I'm 45, and I can confirm Megan and I both absolutely still got it.

Juli: I'm 23! Jamie and Henry were my classmates, so they're the same age as me.

Jamie: Yeah, we were! Time flies, huh? Although I'm a little younger than you by a few months.

Henry: Actually, I'm 24, but that's close enough.

That's all for now! If you have anything you'd like to ask, feel free to send it our way, and we might do this again if people enjoy it!

Notes:

Hey everyone! In case you're wondering: yes, these were real questions submitted by friends in my Discord server! If you'd like to submit a question for Naomi and co, feel free to leave a comment here, or send it to me on Twitter ( /ChroniclerInThe). I had a lot of fun doing this, and I hope I can do another one of these in the future!

Chapter 14: Emily's Obedience

Summary:

Emily may be a brat with her brothers, but she shows off just what a good girl she is with her Master.

Chapter Text

Session Start

[17:00] CollaredDau Hey! Guess who!

[17:02] TheFool Man, I'm stumped

[17:02] TheFool This is a real brain teaser…

[17:03] TheFool Is it Naomi's time-displaced younger self?

[17:03] CollaredDau You got it! This internet witchcraft is frightening me D:

[17:04] TheFool How are you doing, Emily?

[17:05] CollaredDau Good, hbu?

[17:05] TheFool I'm fine

[17:06] TheFool Is that nick just for show or are you actually collared today?

[17:07] CollaredDau I'm collared most days ;p but yeah I got it on rn

[17:08] TheFool Careful your bros don't interrupt us

[17:09] CollaredDau it'll be fine. Jeremy says hi btw

[17:09] TheFool Oh yeah? Why's that?

[17:10] TheFool Hi, Jeremy!

[17:11] CollaredDau my twin has helpfully offered to keep the others away while i chat with you :3 so you can have my full attention!

[17:12] TheFool How selfless of him! Truly he is the modern picture of chivalry

[17:12] TheFool What does he want in exchange?

[17:13] CollaredDau to dump a load in my pussy ;3

[17:13] TheFool How's that going for him?

[17:14] CollaredDau he says very well!

[17:15] TheFool Seems like it might be a distraction, though

[17:16] CollaredDau true, but Master said he wants me with a fresh creampie when he gets home, which should be soon-ish

[17:16] TheFool Anything for Master, hrm? I'm still surprised how obedient you are with your dad.

[17:17] CollaredDau yeah, you mentioned that last time!

[17:18] CollaredDau actually, I told Master about it, and he agreed to make a little video to help explain! Thats why i came on actually, its done!

[17:18] TheFool Oh? I'm excited!

[17:19] -CollaredDau- sent 4

The video starts with a sidelong view of Emily sitting on a couch, completely nude except for her collar. The sound of a door opening is heard, and Emily stands up and smiles.

Emily: Hey there, Master!

Frank: Hey, Em.

Frank walks into the shot, wearing his work clothes. He leans down a little, and Emily gives him a quick kiss on the lips. Then, she reaches down and unzips his pants, and quickly pulls out his cock. She leans over and gives the tip of his penis a quick, enthusiastic kiss. The video cuts as the two start conversing about his day at work.

The video cuts to a shot showing Naomi's front door from the inside. As the door opens and Frank steps inside, Emily walks into frame from offscreen. Again, she is naked except for her collar. Frank is wearing more casual clothes.

Emily: Welcome home, Master!

Emily leans up and gives him a kiss. Again, she unzips his pants and leans down. As she goes in to kiss the tip of his cock, Frank reaches out and puts a hand on her head. After kissing the tip of his dick, instinct takes over, and she takes it in her mouth to begin dutifully giving him a blowjob.

Frank: [Turns to camera as he gets his dick sucked]: So, Mr. Terry, when I touch her head like that, she'll start sucking my dick until I cum or tell her to stop. Took quite a bit of training to get her there, but I think the result was well worth it, don't you?

The video suddenly jumps ahead, showing Emily intensely sucking Frank's cock. He starts to grunt a little as he cums inside Emily's mouth. As soon as he's done, Emily stops, swallows, and looks up at him.

Emily: Thank you, Master.

The video then cuts to show the inside of Emily's bedroom. Emily is on her bed on her hands and knees, wearing nothing but her collar. The camera shows her from a side on view, and her head is turned to address it.

Emily: Hey, Terry! [She waves] So, Master said he'd be home soon. He's stopping by the store on his way home. He sent me a text just saying "Your Bedroom. Doggy." So here I am! Normally that would be it, but he followed up with "Set up the camera for your friend". We might not use this take, though, we've done quite a few.

The video jumps a bit, and a door can be heard opening.

Frank: Nice to see you waiting for me, Em.

Emily: Welcome home, Master!

Frank walks over and leans down so she can kiss him. He starts taking off his pants, and Emily leans over to kiss the tip of his cock. With that done, he goes behind her and penetrates her. He fucks her roughly, giving her the occasional spank, and Emily moans loudly as her body forcefully rocks back and forth.

The video then cuts a final time, showing a closeup of cum dripping out of Emily's pussy.

[17:30] TheFool Wow. That was hot!

[17:31] CollaredDau I hope that clears everything up!

[17:31] TheFool Idk, I think I need more lessons. Are there other takes you didn't use?

[17:32] CollaredDau Yeah. I'll talk to Master about getting you more videos~

[17:32] CollaredDau Speaking of which, I think he's nearly home. Gonna log off so I can be ready for his special kiss. G'nite, Terry!

[17:33] TheFool Good night, Emily. Tell your dad I said hi!

Session Close

Chapter 15: Collared Mom Mailbag Special 2: Electric Boogaloo

Summary:

Naomi and friends answer more reader-submitted questions!

Notes:

(See the end of the chapter for notes.)

Chapter Text

Hello again, Naomi here! It appears there were yet more questions for us, so we've compiled another set of questions and answers, since people liked it so much the first time.

Q: "For Emily, if you were to later have a boyfriend, how do you think that might impact the family dynamic you have with your mom, master, and the other three?"

Emily: We've talked about that sort of thing, actually! It would depend on what specifically my boyfriend was like. I wouldn't date someone I'd have to hide our lifestyle from, so they'd have to be okay with it at the very least. The rest would depend on how dominant or submissive they are. If I were to date a guy who is dominant enough, he'd become my new Master, but if he was more submissive, then I'd have Master and my boyfriend!

Q: "For Naomi, out of the family, who do you think will become the one to be able to sexually please a woman or man the most?"

Naomi: In the entire family? Well, I do hate to brag, but I imagine I'd be at the top of the list. I'm submissive and I have the most experience pleasing partners, haha.

If you mean among my kids, I'd suppose either Emily or Jake. Emily gets in quite a bit of practice and has some "training", so to speak, and she's quite versatile in her skillset. Jake, on the other hand, seems naturally curious and is willing to try anything, and he takes to new experiences fairly quickly. Quite the little ladykiller we've raised, haha.

Q: "For Sai, since you've been considering the lifestyle Naomi has more and more, what do you think the most fun aspect of it will be? Caging your son as his friends fuck you? Rewarding him perhaps?"

Sai: I don't know if I'd want to be like Naomi full-time. I don't want to get into the specifics, but I have a somewhat stressful job and I've to be very assertive and aggressive to get where I am today. Being able to relinquish control in a reasonably safe manner is what I look forward to the most. From my experience, caging my son is very fun, and rewarding him at the end is equally as fun, but my favorite aspect is definitely the exchange of power and control.

Q: "For Rag, what do you want most out of this sexy lifestyle with your mom? Sai, would you give it to him?"

Rag: I feel like I'm answering one of those college admission essay things. Um, I don't know! I guess I just want to try new things. I think what I like most about it is feeling like I can experiment with things and not have to hide behind my mom's back when it comes to sex.

Sai: Well, I am a big proponent of learning and letting people learn by doing, so I'm always happy to let Rag try new things. This is all a learning experience for me, too, really, so it would be hypocritical of me not to.

Q: "For Sai, how do you reward Rag?"

Sai: His reward for putting up with chastity is getting to dominate me for a time after. I'm rather accommodating for whatever he'd like to do as "revenge".

Q: "For Rag, what kind of things do you do with your mom when you're 'in control'? Sai, do you like it?"

Rag: I basically treat her the way I treat Naomi while it lasts. I can be just as mean as she is. I'll interrupt her when she's doing other stuff, ambush her out of nowhere without saying a word, or make her stay near me so I can use her whenever I get hard. I'd like to surprise her with a gangbang, but she's good at figuring those out. I take a lot of pictures and videos, too.

Sai: Yes, I like it. Not that I'd ever tell him.

Q: "For Henry, how did you become a femboy cuck slut? What got you interested in chastity?"

Henry: Oh, wow, this is going to be kind of a long one. I think I should say at the start that nobody forced me into any of this, and I was actually the one who first suggested any change in our relationship. I'm very grateful to Jamie and our friends for being so supportive of me.

So, I guess to start, Jamie and I are friends of Juli's, and her mom (Megan) throws these big gangbang parties on the weekend that we got invited to when we were in school. So, uh, I'm bisexual, as you might be able to guess, and I got increasingly curious about what it would be like to be "one of the girls". Not just bottoming when experimenting with friends, but being a dedicated bottom at one of these parties that receive more than they give. Eventually I brought it up to Jamie (we were dating already), and she said she would support me no matter what I wanted to try doing.

After that is when my, for lack of a better word, "slut/cuck training" started. It wasn't really a cohesive training regiment so much as it was just us trying stuff and piling it on top of each other, but I'll try my best to explain it coherently.

So, the first order of business was getting used to anal. Not just taking it but being able to take it, uh, "sustainably". Jamie and Megan helped me with that, they'd use toys on me and peg me to help me build my endurance up. They were pretty nice and gentle with it at first, too, to ease me into it. Didn't take too long before I was able to cum from it.

The girls helped me pick out cute outfits for crossdressing, too, since I was interested in that (and I thought it would make me more appealing). I tried wigs, lingerie, and makeup, and found some stuff I liked.

The next step was for me to actually try to be a slut at Megan's parties. That went pretty well! Our friends were understanding and they liked my look, and I had a lot of fun. So, at first, I would go and suck and get fucked until I needed a break, and then I'd join the other guys and fuck the other girls. After getting some experience in, I was able to go longer and longer before I needed a break, and my breaks where I used my dick became shorter and shorter.

The chastity stuff came in around when I wanted to try bottoming for an entire party. Funnily enough, it was originally supposed to be a temporary thing. I'd just wear the cage for a party so I didn't get any ideas about abandoning my duties as a slut, and then take it off after the party was over. Then once I'd been trained enough, I wouldn't need it anymore. Thing is, it turned out I actually really liked it and enjoyed the emasculating aspects of it, and after talking it over with Jamie, we decided to progress towards trying to do it full time.

So, at first, I just wore a cage to Megan's parties. It was humiliating and hurt a little, but it was fun. Jamie would tease me about it, too, which was also the start of how we got into cuck stuff. After the parties, though, I'd get to take it off, and I could basically do whatever I want during the "after party". That was a lot of fun, and sometimes I wish I could do that again.

Eventually, I started wearing it during the week when not at Megan's. First just for a day or so, then a few days, then about a week. Jamie started hooking up with other friends outside of Megan's parties, too, while I was locked up. We took to that pretty quickly. I got some advance notice for the first couple times, and I was always there to watch. Soon after, she started dragging me to them without any notice, and I'd just sit there and watch like a good boy. Not long after that, she'd hook up with them and then not tell me about it until after. I didn't mind it at all, since I trust her a lot.

So, yeah, the next obvious step was wearing the cage for longer and longer. That meant going a few weeks with it at a time. That meant for some parties, I didn't get uncaged afterwards anymore. It wasn't every party, but some of them. I'd be able to go a full week, then two weeks, until eventually I was able to do it for a month at a time before we stopped.

Then, after we were comfortable enough with it, we decided to take the last big step. She locked me up full time, and that's basically where we are now. After some discussion, we agreed that she would unlock me once every month, at a time of her choosing, and I'd get to have one uncaged orgasm doing whatever I wanted. And that's basically where we are now.

I guess the final piece was some "extra" slut training, so that I can cum without touching my cock like a good little sissy. Again, no real training regimen for this, we just tried stuff we liked. These days, I'm able to cum from the following: anal, being stimulated through my cage, cock and ball torture (including being repeatedly kicked there), having my chest stimulated, fucking someone with a strapon, and sometimes just from watching Jamie get fucked.

Q: "For Naomi's family, what is everyone's favorite kinks (besides free use)?"

Naomi: Besides free use? Well, I do rather enjoy being choked, or having my leash tugged on. The powerlessness is exhilarating, and helps keep me in my place. ;)

Frank: Humiliating Naomi is great fun.

Emily: Free u- Wait, can't pick that one. Fuck. Not sure if this is a "kink", but I do prefer having other people around. Maybe I'm an exhibitionist, but I just generally like more of a party/group atmosphere.

Jake: Anal! Is anal a kink? I'm always down to fuck a pretty girl up the ass! Or a pretty guy! Ass is ass!

Jeremy: I don't know if I have a single favorite. Um, I really like boobs? That feels like a lame answer, and not very kinky. Are titfucks lame? I like them, I'll go with that.

Jason: Hrm. Well, I like a good footjob, so I guess I'll go with feet.

That's all for now! If you have anything you'd like to ask, feel free to send it our way!

Notes:

Q: "Chronicler, why do you keep doing these mailbag specials? Is it because you're busy with big projects and this is the best way you've found to get new stuff out so your fans don't forget about you?"
Chronicler: Yes. You have seen through my clever ploy. For real, though, I hope these aren't terribly annoying. I think getting out more stuff faster would be better to my older system. Anyway, these were once again real questions I got from readers! If you have a question you'd like answered in a future mailbag special, feel free to send it my way! I don't have a regular "cadence" planned for these, but I got enough material from these questions that I figured it was enough. Nobody complained last time, either, so I'm happy to keep doing these if people are still into them!

Chapter 16: Bit of a Stretch

Summary:

Jake introduces Terry to Claire, one of his family's more unusual friends. Despite being an oddball, Claire proves why she's the size queen of the group with a clip of her horsing around.

Notes:

(See the end of the chapter for notes.)

Chapter Text

Session Start

[14:00] TheFool Hey there, Jake

[14:00] JakeTheSnek Terry! Hi! Hru?

[14:01] TheFool I'm good, how bout you?

[14:01] TheFool Enjoying your summer break?

[14:02] JakeTheSnek Yeah! It's awesome!

[14:02] TheFool What are your mom and sister up to?

[14:03] JakeTheSnek Dunno, I'm not at home right now

[14:03] TheFool Visiting Megan?

[14:04] JakeTheSnek Actually, no! Visiting our friend Claire! O:

[14:05] TheFool Oh, is she the redhead one? I've seen a few pictures of her, but I haven't heard much about her.

[14:06] JakeTheSnek Yeah! She's great! I thought it would be cool to come visit her and she said yes so here I am!

[14:07] TheFool Tell her I said hi!

[14:08] JakeTheSnek She wants to know if you want to say hi yourself o:

[14:09] TheFool Oh. Sure, if she's offering.

[14:09] JakeTheSnek Cool, I'll make a room!

* Now talking in #jakescoolhangout

TheFool has joined #jakescoolhangout

[14:11] JakeTheSnek Okay, give her a minute

ClaireBear has joined #jakescoolhangout

[14:12] ClaireBear Hi!

[14:13] TheFool Hello, Claire. I think I've seen your username before, but I didn't know you were the same Claire.

[14:13] ClaireBear Yeah, probably! I come on here sometimes, but not that often. I usually just chat with friends, everyone else thinks I'm kind of weird.

[14:14] JakeTheSnek You're not weird! You're great!

[14:14] TheFool So how are you doing, Claire? Doing anything fun?

[14:15] ClaireBear I'm good, thanks for asking! Just got my ass fucked, now I'm talking to you!

[14:16] TheFool Oh, wow, sounds fun. I like your style!

[14:16] ClaireBear Thanks!

[14:17] TheFool Is it just Jake at your place?

[14:18] ClaireBear Yeah, my apartment is a little out of the way for everyone else, and it's not as convenient for sex as Megan's place.

[14:19] JakeTheSnek True, gotta be a little sneaky around here

[14:20] TheFool So you usually go to find your partners instead of making them cum to you?

[14:21] ClaireBear Yeah! Usually Megan's place, but I'll visit any of our other friends, too!

[14:22] TheFool So you two are in the same room right now?

[14:23] ClaireBear Yeah!

[14:23] JakeTheSnek Yea! Hey, Claire, wanna turn your webcam on? Then we could just sit around your laptop

[14:24] TheFool If you're comfortable with it, I'd appreciate that.

Claire's webcam goes live, showing Claire sitting next to Jake. Claire is a redhead woman in her late 30s, with shoulder-length red hair, freckles, bright red nails, and large breasts. Neither she nor Jake appear to be wearing any clothing.

Claire: [Waving to the camera] Hi! Is this working?

Jake: [Looking at his phone] Yeah, I can see it.

[14:25] TheFool I can see you too. You look lovely!

Claire: Aw, thank you! You're sweet!

[14:25] TheFool Do you normally hang out naked at home?

Claire: Actually, no! I figured Jake and I would have sex again later, though, so I didn't see any reason to put my clothes back on.

Jake: Maybe sooner rather than later, hehe.

Claire: [She turns to him, sounding almost concerned] Oh, are you ready to go again?

Jake: Uh, maybe!

Claire: [She turns back to face the camera] Hey, is that okay? That's not considered rude, is it?

[14:27] TheFool Nope, that's fine with me!

Claire: Oh, okay!

[14:28] TheFool You don't seem to have much shame, I like that.

Claire: Oh, thank you! A lot of other people find it really off-putting.

Jake: It's charming!

Claire: Thanks, Jake! [She pats his head] Yeah, I suppose it is. I know I sound really weird and naive to people.

[14:29] TheFool You do sound very bubbly. I agree with Jake, it's charming!

Claire: Aw, thanks! I'm actually a terrible flirt! I have no game, and sometimes people think I don't even know what sex is!

Jake: I can confirm she does know what sex is.

[14:30] TheFool I would say you should confirm it for me, but I think I've seen proof enough by now…

Claire: [She turns to Jake] Hey, what have you shown him of me?

Jake: Just some of the clips we've made.

Claire: Oh, I have some way better stuff! [She turns back to the webcam] If that's alright with you, Mr. Terry?

[14:31] TheFool I'm happy to look at anything you want to share.

[14:32] TheFool What sort of stuff is it?

Claire: I'm a total anal size queen, so I've got a couple videos of my butt getting stretched to its limits!

[14:32] TheFool That explains why you get along so well with Jake

Jake: I'm an ass man, it is true. Or ass boy, I guess.

Claire: Yeah, we've got really compatible tastes!

Jake: Claire's always down for anal. It works out!

[14:33] TheFool Would you say your butt is your best ass-et?

Claire: Yeah, definitely!

Jake: That's a good pun.

Claire: Oh, yeah, it's a good pun, too!

[14:34] TheFool So, sorry if this is a stupid question, but isn't Jake a little… small for a size queen? In fact, most of Megan's boytoys seem like they wouldn't be on the bigger end.

Claire: Oh, it's fine! I like it for the taboo of it!

Jake: We're smaller so you can fit more of us in you!

Claire: Yeah! And if I'm really in the mood for size, normal human penises don't really fit the bill, anyway.

[14:35] TheFool So, what, you fuck monsters?

Claire: Horses, actually! Or some big toys if they're not available.

[14:35] TheFool …Huh. Something tells me you're not joking.

Claire: Oh, I'm not! I can show you if you'd like, but I know not everyone is okay with that.

[14:36] TheFool I gotta admit, I'm very curious…

[14:36] TheFool Never met anyone into that before, or at least anyone who was willing to admit it.

Claire: Oh, awesome! I love talking about it! Happy to share and answer questions!

[14:37] -ClaireBear- sent 4

The video opens with a shot of Claire standing next to a large horse. She's wearing a professional-looking suit dress and a pair of red high heels which show off her pedicure. She has her usual big smile.

Claire: Hey! I'm Claire, this is Rudolph [She pats the horse]. They're still doing some setup, but we're gonna see if we can get a load out of Rudolph and into me! [She turns to him] You excited, boy? [She turns back to the camera] He's probably excited!

The video cuts, showing a nude Claire mounted to a device so that her large ass is exposed. In a moment, Rudolph starts to mount her. An assistant reaches over and helps line up the tip of his cock with her asshole. Once it's found purchase, Randolph roughly thrusts into her.

Claire: Fuck! I'm good, I'm good. Oh fuck yeah…

Randolph thrusts into her with rough, uneven strokes, getting deep into her. Her asshole stretches to accommodate the thick, massive cock. Claire moans and pants as the horse fucks her ass.

Not long after, Randolph makes grunting noises as he starts to cum.

Claire: Oh, oh yeah, he's cumming. You pent up, buddy? Oh, that's a lot. Okay, okay I think he's done now.

Randolph dismounts her, and a torrent of cum pours out of Claire's ass as his cock pops out of her. The video ends abruptly as the last of the cum dribbles out of her.

[14:41] TheFool Wow. That's impressive. Would have expected him to last longer.

Jake: Yeah, at least I got him beat there!

Claire: I think it's a biological thing. They wanna cum and get their seed out there quickly. Still, he did a good job!

[14:42] TheFool So, what's that feel like?

Jake: Damn, watching that got me horny.

Claire: You need me to take care of you?

Jake: Sure! Hey, let's move the laptop over to the bed.

There's a brief flurry of activity. When it's over, the laptop is on Claire's bed, and Claire is on her hands and knees, facing the camera.

Claire: Hey! We're back! [She waves]

[14:44] TheFool Welcome back.

Claire: So, to answer your question, it feels really good!

As Claire talks, Jake appears behind her and starts fucking her. Her large breasts start to sway a little from the motion.

Claire: You can feel it pretty deep in you, and it's very, like, big and powerful! You're just totally at this creature's mercy. It feels amazing!

[14:45] TheFool I see

[14:46] TheFool And how does Jake compare?

Claire: He's not as big, but he does just fine!

Jake: You're hurting my feelings, Claire!

Claire: Am I actually?

Jake: No, I'm joking.

Claire: Okay, I have trouble telling sometimes.

[14:47] TheFool How's Jake feel back there now?

Claire: Good! Very enthusiastic! I can tell he likes my butt!

Jake: Heck yeah, your butt is awesome! Not too loose, not too tight! The Goldilocks of butts!

Claire: Thanks!

[14:48] TheFool You two are cute together.

[14:49] TheFool So what happened when Jake came over? Did you greet him naked and just get right to it? Did you talk first?

Claire: I didn't greet him naked, but we basically got right to it!

Jake: I think our clothes are still by the door… Holy fuck this ass is so good…

[14:50] TheFool And he just… stuck it in your butt?

Claire: Yeah!

Jake: Yeah!

[14:51] TheFool You two are really in sync.

[14:52] TheFool Oh shit, I have something soon I gotta go take care of. Bleh.

[14:52] TheFool It was great seeing you two!

Claire: Aw, okay! Take care!

Jake: Bye!

[14:53] TheFool You two have fun fucking. Hope to see you around again, Claire.

Claire: You too!

Session Close

Notes:

Hey all! So, fun behind the scenes trivia: Claire was the last character in my roster I wanted to introduce, but I never really felt like I had a solid reason to, and I didn't want to clutter things up. I was struck with a little inspiration, and now she's finally out there! Hope you all like her~

Chapter 17: Visiting Aunt Megan

Summary:

Megan gets a visit from her sister, and agrees to look after her two young nephews.

Notes:

(See the end of the chapter for notes.)

Chapter Text

"Thanks so much for looking after the boys, Megan." Karen, my sister, says. She has a vaguely desperate look about her; I can tell she hasn't been sleeping well. We're standing near the front of my house. I'm standing in the doorway, she's standing just outside on my front porch, with her two sons behind her.

"Don't worry about it." I say. My nephews walk past me and head inside my place. I'm a little annoyed, because my sister visiting means I can't have my usual 'guests' over, but I suppose family stuff is important. At least she didn't come over unannounced.

"You boys listen to Aunt Megan and Aunt Tanya, y'hear?" Karen calls out.

"Yes, Mom." The two of them reply, using that sulky sort of tone only teenagers can truly use properly. They head inside further into my place.

"Listen, I'm not sure how long it'll take to work out this whole thing with Phil-" She starts. She seems on the verge of tears, so I decide to cut her off before the waterworks start.

"Hey, take all the time you need." I reply, putting on my most reassuring, gentle voice. The sort of thing I used to use on coworkers when I wanted to seem supportive. If I were more petty and bitchy, I'd rub her face in a million "I told you so's" about her deadbeat husband and his descent into weird conspiracy insanity, but I ultimately don't think that would be helpful. "Take care of yourself, okay?"

"Okay…" She replies. She sniffles a little and then goes for a hug, and I hug her back. "Thanks again, Meg."

"Hey, what are sisters for?" I say to her. She seems to take my little quip as a reassurance that everything will be alright. Without saying much else, she leaves, heading back to her car. I close the door behind me before I can see her car pull away.

It's hard to be a respectable authority figure as an aunt when your nephews know your big secret. I made an effort to keep things normal, asked how they were feeling, if they needed anything, had any questions.

"Normal" lasted all of five minutes, and within ten, they were inside me and my wife.

Well. That's just kinda how all their visits tend to go. Easy pussy is a big perk of visiting Auntie Megan.

Tanya and I are next to each other on our knees, holding hands as we both get fucked from behind. We moan loudly for them, begging them to fuck us harder.

They're not the best at it. It's actually kinda obvious they don't get nearly as much experience as my other regulars. Oh, but they want it . They fuck us with a desparate need. We're the only pussy they get, and it's been weeks since we saw them last. They pound our pussies like they need to get all their bang for their buck.

Can't say I blame them. Last time they visited, they had about 20 minutes to get off with my wife and my daughter while I kept my sister distracted. This is the first time they've had quite so much alone time with us. Must be hard to adjust.

We can feel just how pent up they've been when they cum. They're slaves to their own orgasms, grunting and thrusting like they're in pain. They make the cutest little noises when they thrust deep into us like rutting animals, their cocks twitching uncontrollably as they empty their balls. I worry the one inside me is going to burst a blood vessel or something from the intensity, but they both seem alright afterwards.

"Damn, don't tell me you're done for the day already." I say. The two of them are collapsed on the couch, panting and covered in sweat.

"I think they just might be." Tanya adds.

"Guess we'll have to call for backup." I reply as I grab my phone and start texting my regulars. I also make sure to let the other sluts know my place is open for business again. "Don't you boys worry, Auntie Megan's friends are gonna take real good care of you."

Notes:

This was a bit of an experiment for me, I was trying to see how well I could do first person narration. Also always interested in doing more flash fiction, hence why it's short. Hope you like it, don't know if I'll do more stories in this vein!

Chapter 18: Two for One Special

Summary:

Naomi and Emily tell their friend Terry about their first time trying double vaginal.

Chapter Text

Session Start

[13:00] TheFool Hey there, Naomi!

[13:00] CollaredMom Hello, Terry :)

[13:01] TheFool How's you?

[13:01] CollaredMom I'm well, and yourself?

[13:01] TheFool I'm okay.

[13:02] TheFool How's the family?

[13:02] CollaredMom They're well :)

[13:02] TheFool What are the kids up to?

[13:02] CollaredMom At a friend's :) Emily says things are fun.

[13:03] TheFool Tell her I said hi!

[13:04] CollaredMom Done, but she'd like you to tell her yourself, haha.

[13:05] CollaredMom Give me a second :)

* Now talking in #collars

TheFool has joined #collars

CollaredDau has joined #collars

[13:07] TheFool Heya, Em!

[13:07] CollaredDau HI!

[13:08] CollaredMom Hello :)

[13:08] TheFool What are you up to, Emily?

[13:09] CollaredDau at megan's!

[13:10] TheFool Ooo, fun! Taking a little break?

[13:10] CollaredDau nope!

[13:11] CollaredDau i've had a train run on me for 30 minutes it's great!

[13:11] TheFool Wow.

[13:11] CollaredMom You're not still sore from yesterday?

[13:12] CollaredDau lil bit ;p but i have 2 holes!

[13:12] TheFool What happened yesterday?

[13:13] CollaredMom Master wanted us to try double vaginal, haha. It was… rather intense.

[13:13] CollaredDau it was fun tho ngl

[13:14] TheFool Oh, wow. Two cocks in your pussies?

[13:14] CollaredDau yeah

[13:14] CollaredMom Correct :)

[13:14] CollaredMom Claire came by to give us some pointers, haha.

[13:15] CollaredDau yeah, claire is cool!

[13:16] TheFool Sounds like you two had a hell of a time

[13:17] CollaredDau mom do you have the video?

[13:18] CollaredMom Yes, just found it, haha.

[13:18] -Collared Mom- sent DV_ 4

The video starts with their friend Claire, a busty redhead, completely naked on her hands and knees on the floor. Frank, Naomi's husband, is underneath her, also nude.

Claire: Okay, so, the first part is easy. You wanna make sure your hole is well-lubricated. Don't try to get both in at once, do one and then slide the other in.

Frank reaches over and spreads her cheeks apart, then slides his cock into her pussy. Claire lets out a quiet moan.

Claire: Yeah, okay, like that, that's good. Jake, you ready?

Jake: Yeah! [He approaches from off camera and kneels down behind Claire]

Claire: Okay, so, what you wanna do is put the tip near the edge of the hole, then press down and slide in.

Jake: Uh, okay, I think I got it.

Jake does as he's told, pressing the tip of his cock against the edge of Claire's filled pussy. He presses down moving the other cock and creating an opening for him to slip inside.

Jake: I'm in! Fuck, that feels weird!

Claire: Yeah! Good job! Don't go too fast, let me know if you need more lube!

Frank and Jake slowly start to fuck her, moving in and out of her together.

Emily: [From behind camera] How the hell do you keep your cool like that, Claire?

Claire: I don't know, honestly. But staying relaxed is important to keeping comfortable.

Naomi: [From off-screen] It certainly makes you a good instructor, haha.

Claire: It feels good, you guys are doing fine! You could also try alternating your thrusting, it creates a little more friction.

Jake: I think this is good enough!

Frank: Emily, Naomi, you two think you got this?

Emily and Naomi: [In unison] Yes, Master.

Frank: Okay, good.

The video suddenly cuts, showing Naomi and Emily positioned on the floor the same way Claire was. Emily is straddling her master, while Naomi is on top of Jason, her oldest son. One cock is already in each of their pussies, and soon after the cut, Jake and Jeremy force their own cocks into Naomi and Emily, respectively. The two girls let out loud, pained moans.

Claire: [From behind camera] There you go! Remember, relax!

Naomi: Oh, fuck!

Emily: Holy shit, that's fuckin' big!

Frank: You okay, Em?

Emily: Yes, Master. [She lets out a grunt]

Claire: Here, let me give you a little more lube. [Her hand reaches out from behind the camera with a lube bottle, and she squirts some onto the two cocks in Emily's pussy. She reaches over and does the same for Naomi]

The video skips ahead a little to when the guys have reached a steady pace. Naomi and Emily both scream loudly as they get fucked, drowning out the wet sounds of slick cocks slamming into their holes.

Claire: Alright, seems like you got the hang of this!

Frank: Say "thank you", girls!

Naomi: [While trying not to moan] Th-th-thank you, Claire!

Emily: Th- fuck! Thanks, Clai- ah! Oh my fucking god!

Claire: Aw, anytime!

The video then cuts to show Naomi and Emily from behind, presenting their asses side by side. Their pussies are gaping wide open, and cum is dripping out. The two girls are audibly panting as they catch their breath, giving occasional relieved sighs.

Frank: [From off camera] I think we got the basics down, we'll just need to give you two more practice.

Emily and Naomi: [In unison, sounding exhausted] Yes, Master.

[13:32] TheFool Wow, that looked intense.

[13:32] CollaredMom It certainly felt intense, haha. I'm still a bit sore

[13:32] CollaredDau im also sore!

[13:33] TheFool So what did that feel like?

[13:34] CollaredMom It's an intense, strange feeling, haha.I'm not sure how to describe it. It was quite the sensory overload, but it was also unique having two cocks inside me.

[13:35] CollaredDau i felt like i was gonna rip in half!

[13:36] CollaredMom We cut it from the video, but it was a little awkward when the first cock came and the second one was by itself, covered in cum, haha.

[13:36] TheFool Easy, just get more cocks. Problem solved!

[13:37] CollaredDau way ahead of ya! ;p

[13:37] CollaredMom I suppose that's certainly *a* solution, haha.

[13:38] TheFool Did Claire leave after that?

[13:38] CollaredDau nah she stuck around

[13:38] CollaredMom Jake's not going to pass up an opportunity to have a turn with her butt, haha ;)

[13:39] TheFool I imagine he wouldn't!

[13:39] CollaredDau dad made her give him a BJ so she wouldn't talk lmao

[13:40] TheFool …Did he really?

[13:40] CollaredMom Her… peculiarity is a little off-putting to some, haha.

[13:40] CollaredMom They get along fine, of course :)

[13:41] TheFool Aww, well that's good. I think I'd like her if I met her.

[13:41] CollaredMom Perhaps one day you can test that out ;)

[13:42] TheFool Not today, though.

[13:43] TheFool W*rk stuff soon, gotta head off. Nice seeing you! Bye!

[13:43] CollaredMom Take care, Terry :)

[13:43] CollaredDau bye, terry!

Session Close

Chapter 19: Emily's Afternoon Obligations

Summary:

Jake, Jeremy, and Jason return home after hanging out at a friend's place, but instead of their mom, Naomi, they find their sister, Emily, waiting for them, with orders from her father to take care of her brothers.

Chapter Text

It was a wonderful summer afternoon, and three boys approached the front door of a house. After spending most of the day at a friend's place, Jason, Jeremy, and Jake returned home. They chatted amongst themselves, all of them excited to be home and see their mother, Naomi.

They entered the front door and made their way to the living room. In an unexpected turn of events, they found their sister, Emily, sitting on the couch, looking at her phone. She was totally nude save for her collar, and had her leash in her hand.

"Sup, nerds." Emily said, putting her phone down.

"Hey, Em." Jason, her older brother, said back. "Where's Mom?"

"She's out, had to go buy some stuff." Emily explained. "Master sent me out here to take care of you."

"Oh no!" Jake, her younger brother, lamented in a melodramatic voice. "What are we going to do if Mom's not here?!"

"I just said-" Emily interjected, before being interrupted.

"You're right, Jake!" Jason added, in a voice that wouldn't have sounded out of place in an infomercial. "If only there was some way to drain our balls while Mom is out!"

"There has to be a better way!" Jake replied.

"Yeah, guys, real mystery for the ages." Jeremy, Emily's twin, said dryly as he approached the couch, taking hold of his sister's leash. "Hey, Em. Bend over. Also, how was stuff at home?"

"It was cool." Emily answered as she got on her hands and knees. Jeremy quickly took off his pants and approached her from behind, sliding into her as he kept a firm grip on her leash. "It was, ah, fun to, ah, hang out with Master. How was, ah, your thing?"

"Good, no pussy though." Jeremy answered. He fucked her harder and tugged on her leash.

"How come you're so much nicer to Jer, Em?" Jake asked.

"Yeah, the blatant favoritism really hurts." Jason added.

"Be…cause…" Emily answered, her words choked by the tightened collar, "he's… my twin… and… not… a dork…" Jeremy gave the leash some slack, and Emily panted to catch her breath. "Oh, fuck that's good!"

"Yeah, well, at least we were out having fun." Jake countered, pouting a little.

"Keeping, ah, Master's balls empty is, ah, also fun." Emily moaned. "I got laid more than you."

"She has us beat there." Jason admitted.

"Hell yeah I-" Emily started, before her twin violently jerked the leash, cutting her off. He let out a few quiet groans as he thrust into her, filling her with his cum.

"Holy shit, I needed that." Jeremy muttered. He pulled out of her and let go of her leash. "Thanks, Em."

"Alright, you two take your turns." Emily insisted. "Master said to get a load out of each of you, so, y'know, don't keep him waiting."

"What, like, at once?" Jake asked.

"I mean, if you want." Emily answered. "The collar means I'm at your mercy."

"Spitroast?" Jason asked.

"I call her mouth!" Jake said.

The two boys took off their pants and approached their sister from either end. Emily opened her mouth, and began dutifully sucking her younger brother's cock as her older brother picked up her leash and started fucking her from behind. Emily let out muffled moans as she got pounded.

"Y'know what my favorite thing about getting a blowjob from Em is?" Jake asked.

"Not having to hear her complain?" Jason guessed.

"Heck yeah!" Jake answered. The two of them high-fived. Jake looked down and saw Emily looking back up, giving him a vicious stink eye. She popped her mouth off his cock for a brief moment.

"If I weren't collar- Mmf!" Emily started, before Jake shoved his dick back in her mouth.

"Well, you are , so no talking until I cum." Jake said. "That's an order!"

They fucked her in silence for a few more minutes, the living room full of slaps, grunts, and muffled moans. Jake and Jason finished almost at the same time; Jake grabbed her head as he came into her mouth, with Emily obediently swallowing his salty loads as they hit her tongue. She felt Jason's cum fill her pussy, and drip out of her once he went soft.

" Man, that was awesome." Jason said. "Not as good as Mom, though."

"Fuck you both." Emily said, glaring at him.

"You just did, yeah." Jake said.

"Well at least that's overwith." Emily said. "See you nerds later." With that, she got up off the couch and returned to her parents' bedroom to rejoin her Master.

Chapter 20: The Challenge Stream

Summary:

Jake has an idea for a special gaming challenge to do on stream, with help from his mother, Naomi! Can he beat Super Mario Bros while she distracts him?

Notes:

(See the end of the chapter for notes.)

Chapter Text

Jake sat at his desk, feeling a little anxious. A couple days before, he told his friends that he'd be streaming online. It was nothing major, he decided to stream himself playing some games on his Switch. Naomi, however, had come into the background of his camera, though, fully nude. Nobody seemed to complain; if anything, they were supportive and wanted to see more of her. Nobody seemed to think that they'd get banned or that the steam violated any rules. After having tested that particular boundary, he decided to push it farther: he announced on Twitter that he was going to do a "special challenge stream" starring him and his mom. His friends promised to watch it, and they'd spread it enough that there seemed to be a little bit of buzz. Now, the promised hour was nearly upon him.

"You're not too nervous, are you, dear?" Naomi asked. She was kneeling in front of Jake. His chair was facing towards the TV where the Switch was instead of his actual desk.

"It feels weird." Jake said. He looked over his setup one more time; he had a camera on his face, one aimed at Naomi's, and one dedicated to the game capture. "Are you ready? We're live soon. You remember everything, right?"

"I'm ready." Naomi answered. "External cumshots for the camera!" She said with a smile.

"Okay, and we're live in 3, 2, 1…" Jake said. He took a deep breath, then set his stream live. "Hey, everyone, it's me again, your boy Jake! So, uh, today I promised a, um, special challenge stream starring my mom, since a lot of you asked about her last time. Mom, say hi for the camera."

"Hello." Naomi said, giving a little wave. Incoming chat messages seemed to approve of Naomi and her exposed breasts.

"So, today, we're going to be doing something I came up with called the Super Mammary Bros challenge!" Jake announced. "Okay, it's not great , but, y'know, it seemed like fun. Alright, so, for my part of the challenge, I'm just going to play the All-Stars version of Super Mario 1, with rewinds allowed. But, we have a complication, obviously! Mom, care to explain your part of the challenge?"

"My job is to provide distraction." Naomi said. She grabbed her boobs, lifting them up a little to show them off, along with the chain attached to her nipple rings. "I'll be working Jake's cock while he plays, so he has to focus harder to play well. The challenge ends when Jake either wins or is too worn out to continue." People in the chat cheered.

"Alright, so, um, let's go ahead and get started!" Jake said. A bunch of his friends had tuned in, so he was sitting at around 20 viewers. Jake had already started the game on his Switch, he just had to resume it. As Jake started the game, Naomi unzipped Jake's pants and snaked out his cock. He was flaccid due to anxiety, but Naomi quickly got him hard by stroking him. Jake took a deep breath to calm himself down.

Naomi applied some lube to Jake's cock, and some to her tits. Once Jake was sufficiently hard, she slid his cock between her breasts. It was nice and soft, as always, and she quickly got into a slow rhythm. Jake concentrated on finishing 1-1; everyone knew this level by heart. His concentration didn't slip much, although he was also trying not to wonder what would happen.

"This isn't so hard, so far." Jake said.

"I would disagree, you seem quite hard already." Naomi said. The chat responded with various expressions of laughter.

"The fact I haven't cum all day is probably helping that." Jake said. He glanced over at his computer as he cleared 1-1. There were nearly a hundred viewers now, too many to just be friends and friends-of-friends. Total strangers were watching him get a titfuck from his mom, which felt exciting. "You liking it so far, chat? There's a bunch of you here." The chat generally indicated that they liked it.

Since disaster hadn't struck, Jake calmed down. He made his way through 1-2, his concentration starting to falter.

"Okay, starting to feel the distraction." Jake said. He mis-timed a jump and then fell down a pit. "Aw, damn!" He said. He rewound to a bit before and proceeded. "Doing a really good job there, Mom."

"Thank you, dear." Naomi said. "Are you close at all?"

"I, um, might be." Jake said. The chat indicated that they were excited to see a cumshot. "You guys wanna see me cum, huh? Well, that shouldn't be too long- oh fuck, I hate Lakitu." He ran through 4-1, desperately dodging spinies. "Okay, okay, I think I'm close." He said as he felt the feeling welling up in him. Naomi started working his shaft harder. "I, uh, I really wanna finish this level before I burst." He tried to hold it in, but felt his willpower was nearly at the end, though.

Right as he touched the flag, he lost control. He let out grunts and groans as he started to orgasm, coating Naomi's tits in warm, thick cum. Quite a lot of it came out; it hit her neck first, but then dribbled down to her breasts. Jake took a moment to pant and look at his handiwork before checking the chat.

"Alright, first cumshot of the stream!" Jake said. The chat seemed excited by this development. "You guys liked that?" He asked. They affirmed that they did. " Fuck that was good."

"Happy to be of service." Naomi said. Jake's cock softened and slid out from between her tits. This was a good idea after all. Jake thought, feeling much less anxious than before.

The rest of the stream wasn't particularly long; Jake managed to get to the warp area in 4-2, skipping all the way to world 8. Jake realized that he might not have thought this all through as he got to World 8-4, although he'd died plenty. Naomi was working his cock with her tits again, which threw off his focus in the harder levels. After much trial and error, though, he got to the end of 8-4, and managed to beat the game.

"I did it, chat!" He shouted. "I win!" Then, he noticed a question in chat that he hadn't considered: "what do you get if you win?". "Uh, what do I get if I win? I don't know, I hadn't thought about that."

"I assume you want to fuck me." Naomi suggested.

"Hrm. I think we should save that for a different stream." Jake said. "Hey, chat, do you want to watch me fuck her face?" He asked, turning to the camera. Chat expressed enthusiasm for this prospect. "Alright, facefuck it is!" He reached down and put his hands on the back of Naomi's head. "Okay, Mom, be a good girl and open up."

"Yes, sir." Naomi said, taking his cock into her mouth. She went down to the base, taking into her throat. Jake grabbed her head and thrust in and out of her mouth. Naomi made a wet glugging sound, and saliva dripped down Jake's shaft.

Naomi held her breath for as long as she could, but it turned out that she wasn't going to need an air break; her earlier work had gotten Jake plenty riled up. Jake pulled out of her mouth and started jerking himself off, and Naomi kept her mouth open as she obediently awaited his load. He soon came, and covered her face in warm, white spurts of cum. Chat went wild.

"Okay, woo, that was awesome!" Jake said, panting. "That's it for today! Follow me on Twitter for announcements on my next stream!" With that, he ended the broadcast.

Notes:

For the 20th Collared Mom story, I decided to do something a little special! This is actually something I wrote about 2 years ago from what I planned to be a longer story, but I don't really want to finish it. This scene was good, though, and it'd be a shame to let it go to waste~ Hope you liked it!

Chapter 21: Sai's Livestream Debut

Summary:

Jake and Jason are doing a game livestream, when their friend Rag and his mom, Sai, come by their place.

Notes:

(See the end of the chapter for notes.)

Chapter Text

Jake and his older brother Jason are seated at the desk in the living room, streaming to an audience of about 100 people. Jake plays as Jason provides commentary.

Jason: I think it'd be smarter to fully upgrade an item you already have before taking a new one.

Jake: Nah, I wanna take it while it's there, so I don't have to fight with the RNG later.

Jason: You can just reroll to get what you want later.

Jake: No, see, I need to save my rerolls so I can take Mad Groove when it comes up. That's a really vital part of this strategy.

Jason: Remind me which one that is?

Jake: Spawns all items near you every two minutes. That way I can get the rings early on and make sure they're upgraded before the time limit's up.

Jason: Oh, oh yeah, that's important. Carry on, then!

Jake: Still not getting the Laurel. Could you say a prayer to RNGesus for me?

Jason: [ he clasps his hands and lowers his head, speaking in an exaggerated Southern accent ] Lord, please grant my brother the item he needs to kill Death this run.

Jake: Amen, broth-

Both boys are distracted as they hear footsteps approach. From offscreen walks Sai, an Indian woman in her late 30s, and her son, Rag. She looks coldly at them and their setup.

Sai: What are you boys doing?

Jake: We're live streaming!

Sai: Oh. So, there's people watching you?

Jason: Yeah, like a hundred of them.

Sai: And they're specifically watching you play video games? [ she raises an eyebrow ] Couldn't you do something more interesting?

Jake: I mean, sometimes we fuck.

Sai: You do? Great. [ She starts taking off her clothes ]

Rag: M-mom! There's people watching!

Sai: What's the matter? Afraid people will know your mom's a slut for white cock? Besides, I like having an audience.

Jason: [ blushing ] Hey, uh, y'know, you don't have to make it, like, a race thing.

Sai: You're right, I don't. [ Now nude, she raises her leg to step on Jason's chair, placing her foot gently on his crotch ] I choose to. What are you going to do about it, white boy?

Jake: Can we say that on stream? We might get banned.

Sai: If you can fuck on stream without issue, my mildly spicy raceplay is probably not going to get you banned.

Jason: I feel a little weird about it.

Sai: Your cock doesn't seem to feel that bad about it. [ she leans forward to apply a little more pressure with her foot ]

Jake: Hey, we have a better setup for that by the couch! [ He pauses the game ] Rag, you're a cuck, come switch the cameras and keep an eye on the chat and stuff.

Rag: Fuck you. [ He sits down at the computer ]

Sai: Language, Rag.

Rag: Yes, Mom.

There's a few minutes break in the action, with a "We'll be right back!" screen displaying all the while. When the stream returns, Sai is laying on the couch, and the two brothers are devoid of clothing. The camera angle shows off Sai's dark purple nail polish, as well as her anklets and the rings she wears on a few of her toes.

Jake: We're back! We're back, right?

Rag: [ From off screen ] Yeah, you're back.

Jason: So, uh, Sai, do you want to explain why you've got all that jewelry on y-

Sai: What's there to explain? It makes my feet look pretty, and makes you want to cum on them.

Jason: [ blushing ] Y-yeah, but, our viewers-

Sai: Your viewers don't need the lore of why I wear certain things explained to them.

Jason: I suppose not… [He sits down on the end of the couch, and Sai places her feet in his lap. She uses her toes to grab his cock and start stroking it up and down.] Damn, you're good at this.

Sai: I know.

Jake: Alright, make room! [He approaches the other end of the couch, and Sai reaches out to grab his cock. She pulls him closer and takes his cock in his mouth.] She's less scary when her mouth is fu- Ah! [He's silent as he suddenly feels teeth pressing against the skin of his shaft.] I'm sorry!

Jason: Guess she's not in a very subby mood.

Sai: [ She pulls the cock out of her mouth and starts stroking it with her hand .] You two look so pale next to me. It's beautiful, don't you think?

Rag: Your chat certainly seems to think so.

Jason: It certainly looks great to me.

Jake: It'll look better when we cum!

This continues for a while; Jason having his cock rubbed by Sai's feet, and Jake being stroked and sucked by her. There's moans, grunts, and slick noises and Sai expertly works their cocks, a look of intense focus on her face. Their white cocks contrast against her brown skin and purple nail polish.

Jason: Oh, shit, I'm really close! [ He cums soon after, releasing an explosive spray of semen that lands on Sai's stomach, before dribbling out more onto her toes. ]

Sai: Hrm. Not bad. Maybe next ti- [ She's interrupted as Jake starts to cum, covering her face with thick, sticky ropes of his seed ]

Jake: Oh, fuck… Uh… sorry about that.

Sai: Don't apologize. I've always wanted to do one of those cumwalks, you know? Where someone walks around in public covered in cum?

Rag: Mom, no-

Jason: Oh, yeah, that'd be hot! I'd help.

Sai: I guess having some virtual onlookers will do for now. [ She stares into the camera ] Did you enjoy that? I trust you did. And if not, well, tough shit.

Jake: Okay, uh, guess we're cutting the stream early! Uh… man, I still don't have a sign off. Um. Don't… get… urgh, I can't think of anything! Anyway, see you all later! Might post footage if I get anything good. Bye!

Instead of ending with his usual outro, the stream abruptly cuts off.

Notes:

Hey all~ Been a while since I've done anything with Sai, figured I should bring her back for something!
Gonna start a longer fic so it might be a while before the next CM update, although I do have a Halloween special mostly ready to go I'll release later in the month~ Be well, friends!

Chapter 22: Chastity Loves Company

Summary:

Henry and Rag, the cucks of the group, have a heart to heart about their chastity lifestyles, while trying not to get *too* distracted by their nearby mistresses.

Notes:

(See the end of the chapter for notes.)

Chapter Text

"So, uh, your mom seems cool." Henry said, trying to break the awkward silence between him and Rag. The two of them sat inside Rag's house, seated in the hallway just outside the master bedroom. The only thing either was wearing was a chastity cage, each one a little messy with precum.

"Yeah, uh, I guess she is." Rag replied. "She seems a little scary, but-"

"Oh my fucking God!" Jamie screamed from inside the bedroom. " That's so fucking good! " The hallway was full of moans, slaps, and the rocking of furniture emanating from the bedroom. It spooked both Rag and Henry into embarrassed silence.

"So, uh," Rag started, "do you, like, know any of those guys Jamie brought over?"

"I don't know them super well, but I've seen them around." Henry answered. "That's part of the fun, right?"

"Is it like that for, um, all the other guys Jamie… 'knows'?" Rag asked.

"Not really, there's a big variety-" Henry started.

"Fuck me harder, you pussy!" Sai shouted in the other room. "We'll put you with the cucks outside if that's the best you can do!"

"Damn, your mom is intense." Henry whispered.

"Yeah, although she only really gets loud when I'm around and locked up." Rag replied.

"Yeah, that's normal." Henry said. "Jamie's like that, too. She's extra loud when she wants me to hear it, but she can be quiet if she doesn't."

"Does she, um, normally let you watch?" Rag asked. "Mom usually doesn't hide it when we're home."

"It depends." Henry answered. "Sometimes, she-"

"Holy shit, knock me up!" Jamie screamed.

"Ahem, so, uh," Henry continued, blushing a little, "yeah, like I said, most times she has me watch. If she hooks up with someone without me knowing, she'll usually take pictures at least. It's kinda fun being locked out of the bedroom, though."

"Does she, uh, mean it?" Rag asked. "That thing about getting knocked up?"

"Well, not right now." Henry answered. "We've talked it over, though, and, um, I'm not gonna be the father if we ever have kids."

"You two are hardcore." Rag said, admiration in his voice.

"Heh, thanks." Henry replied. "We definitely are, but it's all about what you're personally comfortable with. Speaking of which, what's your arrangement? Jamie made it sound like you were thinking of taking things further."

"We've been doing it for one week of every month." Rag answered. "I get locked up during the week, then it comes off and Mom has to listen to me during the weekend. We're thinking of making it more regular, but we're-"

"Fuck, you got it all over my tits!" Sai shouted. "Are you not jerking off regularly?" There was a muffled, sheepish response.

"Hey, our cucks can just clean it up!" Jamie added.

"So, um, fuck, where was I?" Rag asked. "Oh, right. So, yeah, we were thinking of either changing off weeks with who's in charge, or keeping the current thing permanent where she has weekdays and I have weekends. It's kind of a big commitment, though."

"Very true." Henry said. "At least you're still gonna have some power. I only get to cum, like, once a month without my cage. Some people only do once a year."

"Damn." Rag muttered. "So, uh, now what? Like, what do we do while they, um, finish up?"

"I usually do stuff around the apartment." Henry answered. "Cook, clean, or maybe play games or something. Wanna see a new one I just got?"

"Yeah, sure!" Rag answered.

It was a couple hours until Henry and Rag were called into the bedroom. They had to wait for the men to finish shuffling out, who looked at the two of them with a mix of pity and smug satisfaction.

Jamie and Sai both lay on the bed, both of them covered in semen. It dripped from their holes and coated their skin, giving them an unnatural sheen. The two of them looked exhausted, panting furiously as the boys stood over them.

"You two have a good talk?" Jamie asked.

"Yes, Mistress." Henry answered.

"Good." Sai said. "I imagine it was a great meeting of the minds. Now come clean us up, you worthless maggots."

"Yes, Mistress." Henry said.

"Yes, Ma'am." Rag said.

Henry went to his task with enthusiasm. He licked, kissed, and sucked on Jamie's body, starting at her face and working his way down.

"Y'like that, babe?" Jamie asked. "Those other guys' cum taste good?"

"Yes, Mistress." Henry answered quickly.

Rag did not quite relish his task the same way, although by now he'd overcome his hesitation and cleaned the cum off his mother dutifully. It was salty and left a strange aftertaste in his throat, but he didn't particularly mind it anymore. His only hesitation was that these were complete strangers.

"You're such an obedient little cuck." Sai mused with an evil grin.

"I'll get you back for this." Rag replied.

"I'm looking forward to it." Sai said. "Careful, you missed a spot."

Notes:

Happy Locktober!~ Consider this my Locktober special. I've also got some spookier stuff in the works, as befits Spooky Month.

Chapter 23: The Kindness of Strangers

Summary:

Sai indulges herself at a glory hole

Notes:

(See the end of the chapter for notes.)

Chapter Text

"Mmm…" Sai moaned as she finished swallowing another anonymous load. She was on her knees in front of a glory hole, and looked a little out of place in such a seedy, run down little booth. "How many is that, Rag?" She asked, as the softening cock retreated back into the hole.

"Five loads, ma'am." Rag answered. He was painfully hard in his cage. "Can we go now?"

"Let's see." She knocked on the wall. A few seconds later, another cock emerged. "No, seems they're not done yet."

"How many of them are there? " Rag wondered.

"I don't know, but I'm staying until they're all taken care of." Sai replied. With that, she took the newcomer past her lips and started to bob her head. She relished his taste; they each tasted so similar, yet so subtly different. The personalized mix of musk and precum was unique for each cock she sucked. It gave her such a thrill, sucking off a complete stranger in public. It was one step closer to letting one of them fuck her.

It gave Rag a thrill, too. Though he complained, it was very hot to watch. Not that he could complain much; he was under strict orders not to talk while Sai had a dick in her mouth. The indignity of it made him strain in his cage. He occasionally gave it a futile tug out of instinct, although it didn't bring him any closer to cumming.

After a few minutes experiencing Sai's tongue, her unknown companion was finished. Sai felt his cock twitch in her mouth, felt his cum hit her tongue. Each load tasted slightly different, too. She took a few seconds to relish the taste, then swallowed it down.

"And now?" She asked, turning to her son.

"Six loads, ma'am." Rag answered. Can we go now? "

"We'll see." Sai replied. She gave the wall a knock, and a moment later, another cock poked through.

"Not again ." Rag sighed.

"Get comfortable," Sai said, as she prepared to work this cock, "we might be here all night."

It was late by the time Sai was finished. She drove home under a dark night sky, with the moon in full view. The road was bathed in shadows, with only the occasional headlights of a passing car providing extra visibility.

"Remind me," Sai prompted, "what was the final count?"

"Twenty-two." Rag answered, knowing full well she hadn't forgotten.

"I think that's a new record." Sai noted.

"They must have figured out when you show up." Rag said.

"I must be getting a bit of a reputation there." Sai said. "Good. Maybe I'll see about getting even more out of them…"

"Fuck! I'm cumming!"

Sai kept returning to her new favorite spot, and after working up the courage, she now found herself blindfolded in a room, shackled to a mount. Cum leaked out of her, having formed a trail down the back of the mount all the way to the floor.

" Fuck… " Sai panted under her breath. "How many is that, Rag?"

"That makes ten, ma'am." Rag answered.

"You need a break?" Number ten asked.

"No, I'm good." Sai answered. "Send the next one in."

Notes:

Unplanned second Locktober special! Felt suddenly inspired and I threw this together, hope you all enjoy it~

Chapter 24: Friends That Go Bump In The Night

Summary:

While walking home alone at night, Jake has an unexpected encounter and makes an unusual new friend.

Notes:

(See the end of the chapter for notes.)

Chapter Text

Man, I'm never out this late.

Jake was alone, walking home late at night. He'd had a fun little adventure at a friend's house, but now it was time to head home. It was dark out, although streetlights provided ample illumination, and he occasionally saw other people or cars drive by. His little suburb wasn't particularly dangerous; if anything, he liked the change of pace.

As he made his way back, Jake noticed another boy up ahead. Is that guy… lost? The other boy looked very out of place. Not only was he standing around by himself, he was dressed strangely. Jake could only recognize it as a vaguely East-Asian costume. Halloween's not for a while…

"Uh, hey there." Jake called out. Wouldn't be right to just leave him by himself, would it? "Are you lost?" The other boy froze.

"Have…" The boy replied in a quiet voice, "have you seen… my friend?"

"Uh, I don't think so?" Jake replied. "What's he look like?"

"He looks…" The boy replied, before suddenly turning around, "like this! "The other boy was no boy at all; he had gray skin, a single, large eye and a tongue over a foot long.

"Aaah!" Jake screamed, although he quickly calmed down.

"Gahahaha!" The little imp laughed. "Oh, the look on yer face!" His voice was a bit more gruff than it had been. "Hey, uh, why ain't ya runnin' away?"

"So is that a costume, or are you an actual monster?" Jake asked. He looked at the imp with fascinated curiosity.

"100% real yokai! Hitotsume-kozō desu!" The imp answered. "But, ya can just call me an imp. The name doesn't exactly roll off the tongue for you Westerners."

"Oh, that's cool!" Jake replied. "What's your name? I'm Jake, by the way."

"Nice to meetcha! The name's Hitoshi." The imp replied. "I like ya, kid! Yer one of the good humans, I can tell."

"So, uh, what are you doing out here?" Jake asked. "You seem like you're a long way from home."

"What can I say, I like to travel!" Hitoshi answered. "Came here with some pals from back home. Heard there's some real hottie somewhere around here. Real freak who never says no, y'know?"

"Hey, that sounds kinda like my mom!" Jake said. He got out his phone and pulled up a picture of Naomi.

"No kiddin', that does match the descriptions I heard." Hitoshi muttered as he looked at it. "Alright, kid, lemme go get my pals, and we'll follow ya home!"

"Real nice home ya got here, Miss Naomi." Hitoshi said, before giving Naomi a harsh smack on the ass. "Thanks for yer hospitality!"

"Nice fuckin' holes ya got here, too!" Satoshi, another imp, added. The two of them were fucking Naomi on the floor, with Satoshi in her pussy and Hitoshi in her ass. They had surprisingly large, thick cocks for their size, and pounded both her holes with wild abandon.

"Th-th-thank, ah, you…" Naomi moaned. Her brain felt overwhelmed, both from the pleasure and the strange circumstances she found herself in. Still, she had her orders from Jake, and despite her misgivings, she was not about to disobey her son. Besides, they were good . Satoshi was swirling his long tongue around her breasts, leaving trails of his saliva. Hitoshi occasionally used his as a makeshift whip, smacking her ass and back as he fucked her from behind.

"You said you found these guys while walking around?" Frank asked, leaning over towards his son Jake as he watched two yokai fuck his wife. "They're unusual, but they seem nice."

"Yeah!" Jake said. "What do you think, Em?"

" Fuck yeah! " Emily shouted. A massive oni with thick, leathery burnt-orange skin had grabbed her by the waist with one hand, fucking her like a Fleshlight as her legs dangled helplessly in the air. The creature had impaled her on his cock, and was grunting furiously as he pounded into her. Emily was letting loose a mixture of delighted and pained screams as he repeatedly rammed into her. "Oh my fucking God, this thing's gonna split me in two! It's awesome! "

"Hiryu's a big, scary-lookin' guy," Hitoshi said, "but he's a big softie at heart! Ain't that right, Hiryu?"

"Hiryu like human-friends." The oni grunted. "Hiryu like little human-friend's pussy. Good, tight!"

"Thanks!" Emily panted. "I like your dick, too!"

"His mastery of English doesn't seem that great." Frank muttered.

"Neither's his Japanese!" Satoshi chimed in.

"How you doin' there, hon?" Frank asked. "Enjoying yourself?"

"Oh-oh yes! " Naomi answered.

"Yer wife's a real well-trained slut!" Hitoshi said as he continued to plow her ass. "Need to get me a girl like her back home."

"She's certainly a very good girl." Frank replied. "You can't take her back, though!"

After a while, the yokai started to cum. Hiryu hilted inside Emily; she could feel him throb with her entire body as he emptied his balls into her, filling her so much that she immediately started to drip his cum back out down his cock. Never before had she felt so powerless; she felt like she was at the mercy of some ferocious, primal beast as it filled her with seed.

The two imps finished a little later at the same time. They went deep into their respective holes, twitching and grunting as their cum splashed inside Naomi. When they pulled out, Hitoshi took a minute to admire his handiwork, watching the cum leak out of Naomi and drip onto the floor below.

"Hey, thanks a million, friends!" Hitoshi said. "That was even better than I expected!"

"Nice to meet you too, Mr. Hitoshi." Frank said. He extended a hand, and Hitoshi reached out to shake it. "You and your friends come back anytime!"

"Anytime, huh?" Hitoshi asked. "Might just take ya up on that! Bring over some real freaks next time, hehehe!"
"Well, as long as you don't bring over anyone evil, that's probably fine." Jake said.

"I wanna meet the weird freaks!" Emily chimed in, laying collapsed on the floor with exhaustion.

"Don't you worry, Hitoshi only rolls with fun-loving mischievous yokai!" Hitoshi said. "None of those scary Rising Moon guys!"

"The… what ?" Frank asked.

"Don't worry about it!" Hitoshi said. "Nothin' you humans need to know!"

With that, Hitoshi and his crew left the house, sneaking off to disappear into the night.

"I wonder what other monsters are real…" Jake mused, stroking his chin.

"I hope they at least fuck half as good as your yokai friends." Naomi panted.

Notes:

The first of two Halloween specials I have planned! I'll release the second one some time next week! Hope you liked it~ If there's particular demand, I might introduce more monsters and fantastical elements in future fics. Or maybe this is a non-canon one-off if nobody likes it. Who knows?

Chapter 25: Dick or Treat

Summary:

You're a trick-or-treater on Halloween, and you're about to visit the house in the neighborhood with the best treats

Notes:

(See the end of the chapter for notes.)

Chapter Text

It's Halloween, and you're out trick or treating with three of your friends. You've got a decent haul in your plastic pumpkin-shaped basket. You and your friends are excited, because you're about to go to the house with the best treats: the Amaranth house.

You feel a little nervous as you stand on the sidewalk, looking at the walkway to the door with your friends. This is where Megan Amaranth lives, a beautiful, somewhat eccentric older woman, along with her wife and her adult daughter. You've been looking forward to hitting this house all day.

Your friends approach the door. One of them, feeling courageous, rings the doorbell, before the rest of you are entirely ready. Your heart pounds in your chest as you hear footsteps behind the door.

"Trick or treat!" You all say in unison as the door opens.

"Merry Spookmas!" The woman behind the door greets you. You barely recognize her in her costume; it's Megan's daughter, Juli, dressed in a faithful recreation of Malenia's outfit from Elden Ring, although the bowl of candy she holds looks a little out of place. "Nice costumes!" She grabs handfuls of treats and starts handing them out to your buckets.

"Do you, um," you ask nervously, "do you have any candy buttons?" You have no idea what a candy button actually is. Juli grins as she hears the question, narrowing her eyes at you.

"Candy buttons, huh? Yeah, I think we have some inside." She answers. As soon as she's handed out your candy, she steps back into the house, inviting you in. Your friends walk inside, and she closes the door behind you. "You can leave your candy here if you want." Juli points to a collection of three candy buckets on the floor. You and your friends drop your buckets off before heading deeper inside the house.

As you head down the hallway, a group of boys, smaller than yours, heads the other way towards the entrance. They look satisfied as you walk past each other, and one of them gives a thumbs up.

As you enter the living room, you see Megan, her wife Tanya, and their friend Naomi lined up on the floor on their hands and knees. Megan and Tanya have matching black lingerie, and pointy witch hats attached to their hair with clips. Naomi, as ever, is only wearing a collar, but she's also been given a pair of cat ears. Jamie, Juli's best friend, sits on the couch, looking at her phone. There's the indistinct remains of a costume on the floor, although you can't tell what it was.

"I suppose I spoke too soon." Naomi says as you enter. "Happy Halloween!"

"Hell yeah, more trick-o- treaters!" Megan cheers, turning her head to look at you. "Hey, perfect, four of ya! Jamie, get down here." The four of you start fiddling with your costumes to get at your zippers.

"Sweet." Jamie says. She puts down her phone and joins the lineup.

"Help yourselves!" Megan says.

You're the first to unzip your pants. You hastily take out your cock as you approach Megan from behind. Despite being nearly five times your age, she's still smoking hot. Disregarding the cum dripping out of her, you grab her hips and thrust into her. Your friends claim the other girls shortly after.

Megan's pussy feels fantastic. She's always warm and wet, and every time you've met her, she's always got someone else's cum on her. You thrust into her hard, causing her body to jiggle as you fuck her. The entire room is filled with moans, grunts, and wet slapping noises as you and your friends finally get the pussy you've been looking forward to all night.

"You boys having a good Halloween?" Megan asks, not even bothering to turn around to look at you.

"Yes, ma'am!" A few of you answer.

"I'd say they're havin' a real good one now, if they weren't already." Tanya adds.

"Fuck!" Jamie shouts. "You boys are all so pent-up tonight!"

"They are, it's nice." Naomi adds. "Good thing we're here to provide them relief."

You're not sure how long you spend fucking them, but it never feels like long enough. Maybe the anticipation got to you, or maybe time just flies when you're having fun. At least you're not the first to cum; one of your friends beats you to it by cumming inside Tanya. You don't last much longer after, though. You grab onto Megan's hips for dear life as your hips start to buck, forcing you balls-deep as you fill her with your seed. The orgasm is so good you almost feel like you're going to pass out.

You pull out, admiring your handiwork as you zip yourself back up and get your costume back into place. Your cum leaks out of Megan's pussy, flowing down to her clit before dripping onto the floor. Megan and Tanya turn to kiss each other, whispering things you can't quite catch. You decide to rest on the couch as you wait for your friends to finish.

Once all of you are done, you bid Megan farewell and head back to the front entrance. You pick up your buckets, and Juli opens the front door for you.

"Hope you boys enjoyed yourselves." Juli says as you walk outside. "Stay safe, and Happy Halloween!"

"Happy Halloween!" You say to her as you leave.

As you make your way back to the sidewalk, another group comes by you. You listen as they knock on the door and get candy from Juli. You're soon out of earshot, but you catch one last sentence before you're out of range.

"Is this the house with the candy buttons?"

Notes:

Happy Halloween, everyone! This is my first time trying a reader/character story, I hope it came out okay~

Chapter 26: The NTRVember Special

Summary:

Megan tells Terry and Naomi about an underappreciated tradition, NTRvember.

Notes:

(See the end of the chapter for notes.)

Chapter Text

Session Start

* Now talking in #meetup

TheFool has joined #meetup

[19:00] TheFool Evening, ladies.

[19:01] CollaredMom Good evening, Terry :)

[19:01] OrgyMom Heya, Terry! Happy NTRvember!

[19:01] TheFool How are both of you?

[19:02] TheFool …what on earth is NTRvember?

[19:02] CollaredMom I'm well, thanks for asking! :)

[19:03] OrgyMom NTR! Netorare! Tis the month for all things infidelity! Cheating, cuckolding, the works!

[19:03] CollaredMom I believe it's a Japanese term, haha

[19:03] TheFool I didn't realize you were Japanese.

[19:04] OrgyMom I'm not .-. my wife and daughter are both colossal anime nerds so I just pick this shit up through osmosis

[19:04] CollaredMom It certainly suits you :) You've taken to it quite enthusiastically

[19:05] TheFool Naomi, are you in on this too?

[19:05] CollaredMom I've been dragged into it, haha. Jake thinks it's fantastic.

[19:06] TheFool He sure is an adventurous youngster.

[19:06] TheFool So why not call it Cuckvember or something?

[19:07] CollaredMom You'd have to ask the individual who coined the term, haha

[19:07] OrgyMom I have, it's cause he's also a weeb

[19:07] OrgyMom I am surrounded by weebs D:

[19:08] CollaredMom You say this as if you're not quite the anime aficionado yourself, Megan :)

[19:08] OrgyMom Idk what you're talking about, I've never even heard of a Love Live

[19:09] TheFool What's Love Live?

[19:09] OrgyMom Don't know, never heard of it!

[19:09] CollaredMom I'm not sure that's grammatically correct. Wouldn't it be "Love Life"?

[19:10] OrgyMom No, cause "live" means concert and it's about jpop idols doing a big concert competition, the "Love Live" is the event they're trying to win

[19:10] TheFool You know an awful lot about it despite claiming to never have heard of it.

[19:11] OrgyMom DAMN YOU NAOMI D: FOILED BY YOUR WILY TRICKS AGAIN

[19:11] CollaredMom I have no idea what you're talking about, I assure you :) I'm not clever enough to trick anyone

[19:12] TheFool Okay, so, like, how do you "celebrate" NTRvember?

[19:12] OrgyMom Tanya and I turn it into a competition!

[19:12] TheFool …A cheating competition?

[19:13] TheFool You don't seem to have a particularly monogamous relationship to begin with, does it really count as cheating? Seems like business as usual…

[19:13] TheFool Same goes for you, Naomi.

[19:13] OrgyMom Yeah but we're *dramatic* about it!

[19:14] CollaredMom I don't understand any of it, I just do as I'm told, haha ;)

[19:14] OrgyMom We lie about it and then pretend to be shocked when the other's deception is revealed!

[19:14] OrgyMom ALSO TANYA'S BEATING ME ALREADY ;-; I'm down 2 to 1! She's already got a head start!

[19:15] CollaredMom Oh my, whatever will you do?

[19:15] TheFool Seems like you still have plenty of time to catch up…

[19:15] TheFool Also, how are you scoring these?

[19:16] OrgyMom That's not the point! The point is I'm losing!

[19:16] OrgyMom Uuuuh we score by number of hookup sessions, plus there's bonus points at the end for style

[19:17] CollaredMom Style points, how fancy :) How do you assign them?

[19:17] OrgyMom …okay *usually* we forget by the end of the month BUT STILL

[19:17] CollaredMom Oh, the boys were so happy about helping Tanya score a point, though…

[19:18] TheFool They must be heartbroken. Look at what your carelessness has done, Megan!

[19:18] OrgyMom TRAITORS D: Three little Judases you've raised, Naomi!

[19:19] TheFool How'd they score this point anyway?

[19:20] OrgyMom O, Terry, listen to my tale of woe! I took my beautiful, faithful wife out to enjoy a luncheon meal at a fine dining establishment, when she stepped away to fetch some chapstick from our automobile! I was none the wiser to her deception, until I received, upon my mobile phone, photographs depicting my beloved engaged in lewd acts with Naomi's sons out back by the dumpster!

[19:20] CollaredMom Carl's Jr is "fine dining" to you, Megan? Haha

[19:20] TheFool Shakespeare's got nothing on you, Megan.

[19:21] OrgyMom What did Carl's ever do to you?

[19:21] OrgyMom It's true, Shakespeare never wrote about his wife getting spitroasted behind a fast food joint by a couple of brats. The lazy hack.

[19:22] TheFool So then what happened?

[19:22] OrgyMom I just kinda had to wait there. Ngl I kinda wanted to go join in . *someone's* gotta watch the stuff tho

[19:23] OrgyMom She came back like 15 minutes later and just smiled at me all smug n shit D:

[19:23] OrgyMom The hate sex that night was *fantastic*

[19:23] CollaredMom Can't say I've ever tried hate sex, personally

[19:24] CollaredMom The boys were certainly proud of themselves ;)

[19:24] TheFool Heartbreaking. How'd she score the other point?

[19:25] OrgyMom Oh, the *betrayal!* My lovely wife and I had a splendid evening out (not at Carl's Jr before anyone asks) and had planned to partake of the cinematic arts!

[19:25] OrgyMom BUT WOE! I went to use the room of rest, and upon my return, found that she'd had a gentleman caller waiting outside, and snuck him in in my absence! I found him taking her roughly from behind!

[19:26] TheFool Oh no! Although I guess you could have watched your thing after they finished.

[19:26] OrgyMom I mean, she brought enough to share

[19:26] CollaredMom How thoughtful of her, haha

[19:27] OrgyMom Also we were just gonna riff on some bad Halloween specials

[19:27] OrgyMom So we put those on and got fucked together, it was super romantic~

[19:28] CollaredMom Getting fucked together is certainly quite the bonding exercise, in my experience, haha ;)

[19:28] OrgyMom Did you know there's a Grinch Halloween special?

[19:28] TheFool Get a lot of mother-daughter bonding done that way, Naomi?

[19:28] TheFool I did not know that

[19:29] OrgyMom That's cause it FUCKING SUCKS

[19:29] OrgyMom The sex was fantastic tho -w-

[19:29] CollaredMom We do, as a matter of fact :) Although we have less control over it than Megan and Tanya, naturally ;) haha

[19:30] CollaredMom So you wouldn't recommend it, then, Megan?

[19:30] OrgyMom What, sex? I'd reccomend sex, gets two big thumbs up from me!

[19:30] TheFool How many stars do you give it out of 5?

[19:31] OrgyMom 5, easily!

[19:31] TheFool Also, didn't you say you had a point yourself? How'd you get that?

[19:31] OrgyMom .

[19:31] OrgyMom .

[19:31] OrgyMom I didn't even plan that one some kid just bumped into me while i was at Target

[19:32] CollaredMom You, caught unawares? You always seem so in control, though, haha

[19:32] OrgyMom Gave him a quick blowjob in a changing room, decided it counted and claimed my point :3

[19:32] TheFool Now just 2 more to go until you have a lead!

[19:33] CollaredMom I'll be cheering you on, Megan :)

[19:33] OrgyMom I'm gonna tell your kids to make you wear a cheerleader outfit :x

[19:33] CollaredMom I think I'm a little old to pull that off, haha

[19:34] TheFool So, Naomi, how many points do *you* have?

[19:34] CollaredMom Master and I weren't intending to have a competition in that regard, haha. We only really made a "thing" of it once, and that was more Jake's doing

[19:35] TheFool So no score being kept?

[19:35] CollaredMom Master doesn't quite seem to get it, I confess neither do I

[19:35] CollaredMom He was more confused than anything when Jake started making a thing about it after Master walked in on us, haha

[19:35] OrgyMom WAIT I DIDN'T HEAR ABOUT THIS

[19:36] OrgyMom FUCKING LMAO

[19:36] TheFool Wow, Jake really taking the lead there

[19:36] CollaredMom Admittedly, he was rather distracted with my pussy at the time ;) his explanation was not the most coherent

[19:37] TheFool So, what, did Frank just shrug and leave him to finish fucking you?

[19:37] CollaredMom No, he waited patiently for Jake to finish, and then got a slightly better explanation, haha

[19:37] OrgyMom OMFG

[19:37] OrgyMom IT KEEPS GETTING BETTER

[19:38] CollaredMom Master humored him for a bit, but still didn't quite get it

[19:38] CollaredMom Although I got "punished" later for my infidelity ;) I certainly learned my lesson, haha

[19:38] OrgyMom Oh is *that* where those marks were from?

[19:39] TheFool What was your punishment?

[19:39] CollaredMom I got spanked and slapped around :) It was very fun!

[19:39] TheFool So he's not planning any revenge-cheating?

[19:40] CollaredMom Why would he need to? He already cuckolds me with other women, especially Emily and Sai, haha

[19:40] TheFool Having your daughter as your husband's mistress is really erotic, I think.

[19:40] CollaredMom I agree ;)

[19:41] OrgyMom Idk, Woody Allen's ex might argue with you on that one

[19:41] TheFool Oh God, I forgot about that…

[19:41] CollaredMom Always quick on the draw, Megan :)

[19:42] TheFool Well it was lovely chatting with you ladies, but it's really late here and I have w*rk tomorrow.

[19:42] OrgyMom Nini!

[19:42] CollaredMom Good night, take care!

[19:42] CollaredMom Just as well, I should help empty the boys' balls before they go to sleep ;)

[19:43] OrgyMom Dirty girl o:

[19:43] TheFool Talk to you all later! Bye!

Session Close

Notes:

Merry NTRvember, everyone! Just a heads up that there might not be a ton of CM this month, cause I've got some comms and other things lined up.
Hope you enjoyed this, I went for something a little more focused on dialogue and personality over just The Sex!

Chapter 27: The Collared Mom Christmas Special

Summary:

Naomi's family is celebrating Christmas, when they get a visit from a special someone who teaches them the true meaning of Christmas.

Notes:

(See the end of the chapter for notes.)

Chapter Text

Christmas had come to Naomi's household, and everyone was in a festive mood. The Christmas tree was decorated with lights and ornaments, with plentiful presents underneath. The whole family gathered around it, listening to the same handful of Baby Boomer Christmas songs that everyone plays every year. The boys had on suitably festive Christmas sweaters to really sell the atmosphere; Naomi and Emily were just wearing their collars.

"Can you guys believe it's been an entire year since our shenanigans were first posted to Archive Of Our Own dot org?" Jake asked.

"Has it really? " Naomi asked. "I'm amazed we're still going, honestly."

"Yeah," Emily chimed in, "like, you'd think the 'family with a free use mom' would run outta steam after, what, four fics? How much can you do with that?"

"A year's worth, at least." Jason said. "Although you're free use, too, dummy." Emily stuck out her tongue.

"Do people complain?" Jeremy asked. "About, like, our whole shtick being kinda… y'know… sexist?"

"That would require people to leave comments." Frank pointed out. "They don't complain about anything! "

"Well, I'm certainly happy to entertain our fans however they'd like." Naomi said.

Just then, they heard a noise from the fireplace as something started sliding down the chimney. The five of them watched as a short little one-eyed imp emerged from the fireplace, and grumbling in Japanese. He had on a red velvet santa outfit, complete with hat and fake beard, although he was too short and thin to be remotely convincing.

"Hey, it's Hitoshi!" Emily said.

"What? Nah, it's me, Santa Clause!" Hitoshi said. "Ho ho ho! I came here on my flying sleigh!"

"Oh, have you got any flying reindeer?" Naomi asked.

"I, uh, yeah." Hitoshi answered. "Actually, we ain't got those in Japan, I had to make do with flying tanuki."

"Did you actually fly here?" Jake asked.

"Nah, I just climbed on yer roof." Hitoshi explained. "Anyway, Merry Christmas! Now, I hope ya got the traditional MILF and cookies yer supposed to leave out for Santa!"

"I believe it's actually milk and cookies, traditionally." Naomi said. "However, I do hope I might count as a humble offering for you, 'Santa'."

"I think I saw a porn thing called 'MILF and Cookies' available on a hotel pay-per-view thing once." Frank mused. "It was like a decade ago, on a business trip."

"Was it any good?" Jake asked.

"Dunno, seemed like kind of a waste of money." Frank answered.

"Yare yare, stop overanalyzing my joke!" Hitoshi demanded. He found an open chair and sat down in it. "Alright, how about ya come sit on Santa's lap, Naomi?"

"Are you sure that's wise?" Naomi asked as she approached his seat. "I'd hate to squish you…"

"Ya raise a good point." Hitoshi replied as he undid his belt and whipped out his dick. "Although, I kinda had in mind a little more motion goin' on, y'know?"

"Ah, well, who am I to refuse?" Naomi said with a smile. She turned around and started to sit on his lap, stopping when she felt one of his hands grab her waist. Hitoshi took a second to line his cock up before lowering her down onto him. He gripped her hips with both hands and started thrusting up into her, causing her tits to bounce and the chain connecting her nipple rings to jingle.

"You kids are so lucky." Hitoshi said. "Ya got this grade-A pussy on tap! Hardly fair!" He used his long, whiplike tongue to smack Naomi's ass, eliciting a squeal.

"Hey, we have two grade-A pussies on tap!" Jason corrected.

"I, um, thanks?" Emily said, scrunching her face in confusion. "Not sure how to feel about that, but I think it was a compliment."

"You should feel so happy about it that you come over here and give me a blowjob." Jason replied, giving his sister a shit-eating grin.

"That's not really how I feel, though." Emily replied.

"Em, go suck your brother's dick." Frank ordered. "Actually, make sure all of them get a turn."

"Yes, Master." Emily said. Jason undid his zipper as Emily knelt in front of him. She obediently grabbed his cock and took it into her mouth, bobbing up and down on it as Jason grabbed the top of her head.

"Man, you guys are such a cute family!" Hitoshi said as he continued his thrusting. "Ya got real lovely kids, Naomi."

"Th-thank you, ah, Mr. Hitoshi." Naomi moaned.

"Don't thank me yet, I ain't given ya my gift! " Hitoshi cackled.

A few minutes later, Hitoshi groaned as he thrust his candy cane deep inside Naomi, pumping her full of warm Christmas cheer from his bountiful sack. He pulled out of her, and his member started to soften as he caught his breath.

"Thank you for the present, Santa." Naomi said, standing back up. Cum dripped down the inside of her thighs.

"Heh." Hitoshi panted. "Alright, I got a real present for ya." He said as he fished around in his pocket. Frank and Naomi watched with curiosity as he pulled out what looked like an unfinished house key. The head of the key was silvery and metallic, but the shoulder and blade were unnaturally black.

"What is that?" Frank asked.

"Ya don't need to know the particulars, but that key will letcha go visit more exotic locales." Hitoshi said. "Tested it myself, shouldn't be dangerous!"

"How does it work?" Naomi asked, tilting her head.

"Easy! Ya just stick it in any door and open!" Hitoshi answered. "You'll know what to do after that."

"Woah," Emily said, "that sounds- mmf!"

"Hey!" Jason said as he grabbed her head and forced his cock into her mouth. "You're not done! Nobody said you could talk!" Emily gave him the stink eye as she went back to sucking his dick.

"Naomi, go help our poor daughter." Frank said.

"Of course, Master." Naomi replied. She bowed, then moved to kneel in front of Jeremy on the couch.

"Alright, Santa's got other houses to visit, if ya catch my drift." Hitoshi said as he got up out of his seat. "Merry Christmas, and enjoy your new gift!"

"I'm sure we'll put it to good use." Frank said as he picked the key up. With that, Hitoshi left, leaving the living room in silence, save for the sounds of Emily and Naomi sloppily sucking cock.

Notes:

Merry Christmas, everyone! Can't believe it's been a whole year of Collared Mom. Crazy.
I never expected Naomi and her family and friends to be so popular. I'm grateful to all of you who have stuck with me.
I'm a little busy with other projects at present, but I do have some future ideas. Might do some stories in a bit more fantastical direction (sorely tempted to do a little crossover with another fic I have in the works~)
Thank you for your continued support, and here's to another year of Naomi's incest shenanigans!

Chapter 28: Training Day

Summary:

Terry talks to Emily and Naomi about how you actually "train" a free use slut.

Notes:

(See the end of the chapter for notes.)

Chapter Text

Session Start

* Now talking in #collars

TheFool has joined #collars

[11:00] TheFool Hey, ladies! How are you both?

[11:00] CollaredMom I'm well :) Nice to see you, Terry!

[11:00] CollaredDau I'm good! Hbu?

[11:01] TheFool Good to hear! I'm also doing well.

[11:01] TheFool Still a little surprised you both showed up on time, heh.

[11:02] CollaredMom Master said we would. We're not ones to disappoint. ;)

[11:02] CollaredDau Y'know, somehow I doubt he's gonna just stop at wanting to chat with us now that he has a taste of Master's power ;p

[11:02] TheFool Maybe I'll try seeing what else I can get away with now that Frank and I talk outside of here.

[11:03] CollaredMom Be careful, Terry! You might feel a little spoiled once you try some well-trained sluts ;) You may never be able to go back

[11:03] CollaredDau He could always train them himself ;p

[11:03] TheFool I think that's a risk I'm willing to take.

[11:04] CollaredDau Why am I not surprised? Lmao

[11:04] TheFool Actually, I've been meaning to ask: is there any actual "training" involved?

[11:04] CollaredMom Yes. :)

[11:04] CollaredDau Yea!

[11:05] TheFool …I'm really curious now.

[11:05] CollaredMom About? ;) You know we're not shy, haha

[11:06] TheFool I know, but I still feel weird asking.

[11:06] TheFool Okay. What kind of 'training' do you both undergo?

[11:07] CollaredMom Well, I suppose you could broadly break things down into skill, obedience, and endurance. My training with Master wasn't particularly formal, haha.

[11:07] CollaredDau Mine was, lmao

[11:08] CollaredMom By the time we started our current arrangement, I already had plenty of 'practice' with Master, haha. The only thing I was really lacking was any sort of endurance training, but Master and Megan were more than happy to help me with that ;)

[11:09] TheFool You mean with her, uh, parties?

[11:09] CollaredMom Exactly, haha. She had her 'guests' keep me busier and busier for longer and longer, per Master's wishes. I can quite comfortably handle a cock in each hole for a while now. :)

[11:10] TheFool Wow, that's hot.

[11:10] TheFool Em, you said you had more formal training?

[11:11] CollaredDau Yeah, after I said I was interested in possibly wearing a collar fulltime

[11:11] CollaredDau Master said it would be mandatory if I agreed ;p which I did, mwehehe

[11:12] CollaredMom She had quite the catching up to do, not having my experience ;)

[11:12] TheFool Oh yeah, Naomi *would* have the advantage there…

[11:13] CollaredDau Yea. I had to get a lot of practice in ;p

[11:13] CollaredDau Master and Mom spent a lot of time teaching me how to suck cock. They'd give me pointers n stuff, it was actually super helpful!

[11:14] TheFool Oh, wow, I was picturing something more harsh.

[11:14] CollaredDau Nah, Master's pretty chill

[11:14] TheFool Yeah, I've noticed!

[11:15] CollaredDau 'course, once I had the basics down, I had to improve ;p

[11:15] CollaredDau They started timing me. Master would time how long it took me to make him cum, and I'd also have 'competitions' with Mom with my bros

[11:16] CollaredDau That was also part of the obedience stuff, cause training was on a schedule I had to adhere to ;p

[11:16] TheFool Oh, how strict was it?

[11:17] CollaredDau Training sessions with Master were daily until I was down to a 10 minute average

[11:17] CollaredMom I'm still very proud of you :)

[11:18] CollaredDau But it was also on a schedule, I had to show up on time and be ready n' stuff

[11:18] CollaredDau …its kinda fun ;p

[11:19] TheFool …Man, I shouldn't talk to you two while I'm supposed to be working. You're very distracting!

[11:20] CollaredMom You picked the time, Terry. We merely obliged. :)

[11:20] CollaredDau Yea, you kinda did this to yourself, lmao

[11:21] TheFool …I cannot argue with you there.

[11:21] TheFool Truly I am hoist by my petard.

[11:22] CollaredDau I thought we weren't supposed to say that word anymore? ;p

[11:22] CollaredMom No, dear, it's a Shakespeare quote :)

[11:23] TheFool I believe it's a type of explosive device used for breaching walls.

[11:23] CollaredDau Ooooooh! Idk we didn't get to that one yet in school

[11:23] CollaredMom Oh, is that what that is?

[11:24] TheFool I believe the original meaning is that someone is 'hoisted' into the air by their own petard, ie, it blows up in their face.

[11:24] CollaredMom Ah, that makes sense :)

[11:25] CollaredDau Wow, ur so smart, Terry o:

[11:25] TheFool Have you really not covered Hamlet in school?

[11:25] CollaredDau Nope! I think that's senior year of high school

[11:26] TheFool Oh, that actually makes sense. It's pretty long.

[11:27] CollaredMom I was always fond of MacBeth for its brevity, haha. And it's easy to follow :)

[11:27] TheFool I think you mean The Scottish Play.

[11:28] CollaredMom I think it's only bad luck if you say the name inside a theater, haha.

[11:28] TheFool All the world's a stage, Naomi!

[11:29] CollaredMom Ah, I hadn't considered that :) Clever!

[11:30] TheFool Alright I have actually important work stuff that needs my attention. Chat with you ladies later, okay?

[11:30] CollaredDau Bye, Terry!

[11:31] CollaredMom It was lovely seeing you, Terry! Take care :)

Session Close

Notes:

Hey everyone! Probably the last one of these for 2022, thank you all for sticking with me! Have a Happy New Year~ I've got some... *interesting* ideas for 2023, so keep an eye out!

Chapter 29: Megan and Naomi's Excellent Adventure

Summary:

Naomi brings the key she got for Christmas to Megan, and the two decide to give it a try. Continuation of the Christmas Special!

Notes:

(See the end of the chapter for notes.)

Chapter Text

"Okay, hang on," Megan said, rubbing her temples as she gathered her thoughts, "you're telling me that a little imp guy visited your house and just… gave you this key? And it's supposed to lead to other worlds?"

"I believe so, yes." Naomi answered. They were sitting in Megan's living room, sitting on the couch and looking at a strange key left on the coffee table. "We haven't really felt up to trying it out, though."

"Can't imagine why strange keys from imps would be suspicious." Megan quipped, picking up the key. The blade looked unfinished, and was an unnaturally black hue, while the head was shiny and silver. "Alright, well, I'm always up to try new things. You wanna give it a whirl?"

"I would feel a little safer using it if I was with you." Naomi admitted.

Megan stood up from the couch, and Naomi followed. After giving her wife, Tanya, a quick kiss goodbye, Megan approached the door to the kitchen. She stared at the door, then at the key.

"So, we just… stick this in the keyhole?" Megan asked. "That's how it works?"

"That's what we were told." Naomi answered.

"Okay, well, here goes nothing." Megan said. She tentatively pressed the tip of the key against the door's keyhole. To her surprise, the blade turned into a soft, gooey substance, and easily slid into the lock. The edges around the door glowed with a strange energy, evidently no longer leading to the kitchen.

"I suppose that means it worked, then." Naomi said. She looked at Megan, and Megan looked back at her.

"Yeah, I guess it does." Megan said. "Now I guess I just…" She turned the key, and felt something unlock inside the door. It certainly didn't feel like the usual lock. Megan took a depe breath, and then pushed the door open.

On the other side of the door was a large room in what looked like an old mansion. It was mostly empty, save for a table next to the door. Another door stood across from the one they'd just opened. It was eerily quiet, with nary a peep coming from this strange place.

"It looks safe." Megan said. She removed the key from the door, and tentatively stepped inside. Her heels clicked loudly against the floor, but nothing else seemed to happen. She poked her head in and peered around, before stepping fully inside. "Alright, well, guess there's-"
"Hey, Naomi, that you?!" A voice called out. "Be with ya in a bit!"

"Is… is that your imp friend?" Megan asked.

"It sounds like him." Naomi said. She stepped inside the door, before closing it behind her.

"Hey, welc- Oh, ya brought a friend!" Hitoshi said as he opened the other door. He was wearing a yukata and little else. "Nice to see ya! Was wonderin' when ya'd give the key a try."

"It's nice to see you, too." Naomi said with a bow. "Hitoshi, this is my friend Megan. Megan, this is Hitoshi."

"Heya, Mr. Hitoshi." Megan said. "Or, uh, konnichiwa, Hitoshi-san."

"Konbanwa, Megan-san." Hitoshi replied. "My English is real good, though, dont'cha worry!" He motioned to the door he'd just come through. "C'mon, come inside! Been waitin' to give ya a bit of an introduction!"

"Have you?" Naomi asked, as she and Megan followed him inside the mansion.

"Yeah, wouldn't want ya bumpin' into anything dangerous." Hitoshi said. "Now, the mansion's safe, and everything for a few miles around should be safe, but don't wander too far away cause the Rising Moon's got people stationed, and they ain't fond of the living."

"These would be the less friendly yokai you mentioned the first time we met?" Naomi asked.

"Yeah. That's kinda all ya need to know." Hitoshi continued. "Dickheads, hate the living, led by a big spider. Avoid at all costs!"

"Like, a gross spider, or a sexy spider?" Megan asked.

"Empress Sayoko is beautiful ." Hitoshi answered. "But ya don't wanna see her. Trust me. Alright, now where is…" He stopped in front of another door, with a small, messy table next to it. He rifled through the things scattered on its top until finding a folded piece of paper. "A-ha! Alright, ladies, here ya go." He handed the sheet over to Naomi, who tentatively took it and unfolded it.

"This looks like some kind of map." Naomi noted. The sheet depicted what looked like the top view of a long hallway, with several doors labeled in black ink. At the end of one hallway was another room, with three more doors inside. These were marked in red.

"That's cause it is a map!" Hitoshi explained. "Now, beyond this door is my little hallway full of doors that are attuned to safe, fun locations. Ya can go anywhere there, say you're a friend, and you'll be fine."

"What about these ones at the end here?" Megan asked, pointing to the extra doors marked in red.

" Those are…" Hitoshi replied, pausing as he struggled for a word. "More business than pleasure, let's say. Less sexy, and some of 'em can be dangerous."

"I must admit you've piqued my curiosity." Naomi said. "And you've still labeled them."

"Dunno if I wanna find out what lives in 'The Crawler's Burrow' or 'The Hornet's Nest', personally." Megan noted. "Not gonna lie, though, I kinda wanna see what 'Zyx'ithel' looks like, though. Like. The fuck is that?"

"Actually, that one might be safe." Hitoshi said. He furrowed his brow as he thought about it. "Still, I wouldn't go unannounced if I was you. Besides, the other places are a lot better! Go, try 'em!"

"So, do we uh, 'owe' you for your generosity, Hitoshi?" Megan asked, looking curiously at him.

"Not at all!" Hitoshi replied. "I actually got somewhere to be soon, anyway. But if ya do feel like lettin' your favorite imp have a go with ya, I'd certainly take a rain check."

"Y'know what, I like you, why not!" Megan said.

"Have fun, girls!" Hitoshi gave a quick wave and then departed to attend whatever his business was.

"Well then, I suppose we should decide where to visit." Naomi suggested. She and Megan looked over the map they'd been provided. "I think that door leads to our world." She noted, pointing to one that was just labeled "Naomi".

"What do you think 'Ring of Lust' means?" Megan asked. She pointed to a door labeled "Zak'var (Ring of Lust)".

"I've no idea." Naomi confessed. "I'm curious too, now…" She looked at Megan. "Are you sure it's safe?"

"Well, your little imp buddy said any of these should be, so probably." Megan reasoned. She approached the door, double checked that it was correct on the map, then opened it.

On the other side of the door was some kind of building made from wood and stone, with a messy desk and a few chairs. The floor was made from stone, with animal pelts serving as rugs. Megan guessed it was an office, a guess further solidified by the presence of a woman seated at the desk staring at her and Naomi.

"Are you… friends of Hitoshi's?" The woman asked. She was unlike anything either Naomi or Megan had ever seen. She had brown skin and dark hair tied up in a ponytail, brown eyes, and what appeared to be small tusks protruding from her lower lip. She wore a rather skimpy outfit made of wolf pelts. Even though she was seated, Megan and Naomi could tell she was rather tall.

"Yeah, he said we could just go nuts." Megan said. "I'm Megan, by the way, this is Naomi."

"Zakyra, it's a pleasure to meet you." The woman replied. "Are you… humans? You look like humans."

"Yes, yes we are." Naomi answered.

"Sorry if we're, uh, underdressed ." Megan said. She was wearing little more than a corset, black nylon stockings, and a pair of high heels. Naomi, as was her wont, wore only her collar.

"No, no, you'll fit right in." Zakyra replied. "Welcome to Zak'var."

"Will we? Oh, that's good to hear." Megan said. "So, uh, I take it you're not a human, then?"

"I'm an orc, as are most of the other inhabitants." Zakyra answered. "Although, we've got races from all over Draenor living here."

"Draenor, huh?" Megan asked. She leaned over and whispered to Naomi. "Holy shit, Naomi, we're in World of Fucking Warcraft! That's a fucking orc! "

"Do you know much about this place, then?" Naomi whispered back. "I thought orcs were green."

"Nah, this place isn't in the game." Megan answered. "Look, I'll explain the lore and shit later." She returned her attention to Zakyra. "Thank you so much for having us! So, uh, what's the deal around here? Don't suppose you could give us a tour?"

"Sure," Zakyra answered, "just give me a moment to-"

"Zakyra, are you in your office?" A woman's voice asked, quickly approaching the room. "The expedition to Highmaul has-" The speaker stepped inside, caught off guard by the presence of Naomi and Megan. She looked positively satanic, with red skin, goat-like horns, black hair, glowing green eyes, and hooves. She stood nearly 7 and a half feet tall, and was adorned in intricate metallic armor. "More humans? Someone tell Violet, she'll be thrilled ."

"Hey there, beautiful." Megan said. "We're, uh, tourists, visiting for the first time. I'm Megan! And my collared friend here is Naomi."

"H-hello." Naomi said weakly, giving a little wave. Although she hadn't set foot inside a church in years, Naomi still felt an instinctive fear of what was very clearly a demon.

"Bold, I like you." The demon replied with a grin. "I am Raxicas. Once a commander in the Burning Legion, now but a humble announcer for the Ring of Lust."

" Oh , so it's like an arena, then?" Megan asked.

"We were wondering about that." Naomi chimed in.

"Hey, how about you give the two of us a tour of your little town?" Megan asked, winking at Raxicas.

"Yes, I suppose that's in order." Raxicas said. "Or I could bend one of you over Zakyra's desk here and now."

"Oh, we are so down for that you have no idea." Megan said. "Right, Naomi?"

"I do as I am ordered." Naomi said. "Although, I must say, I've not often been bent over by a woman …"

"I think you'll find that," Raxicas started, before quickly removing her armor and revealing a large, equine cock, "I'm not like most other women. I trust this will not be a dealbreaker?"

"Of course not!" Megan replied. "We're big on trans rights and all that!"

"I am yours to command, Lady Raxicas." Naomi said with a bow.

"Wonderful." Raxicas said. "Your friend, is she always this subservient?"

"Oh, she is." Megan replied. "Naomi, go be a good girl and rim our new friend."

Without saying anything, Naomi made her way behind Raxicas and dropped to her knees. She reached up and grabbed the demon's firm, muscular cheeks, spreading them apart to reveal her hole. With no hesitation, she buried her face in the demon's ass, probing at the ring with her tongue.

"She's not half bad." Raxicas mused. "Well-trained, I can tell."

"We make sure she gets a lot of practice." Megan said. She slowly approached Raxicas, eyeing her rapidly hardening cock. "Although, seems like it might not be enough for a big girl like you." Once she was close enough, she reached down to touch it, placing a hand on the shaft. The two locked eyes, grinning hungrily at each other.

"You say that as if you're not dying for a taste." Raxicas replied.

"Was it that obvious?" Megan asked as she got to her knees. Precum was dribbling out of the tip, and Megan started by flicking it with her tongue. She planted a kiss on it, before continuing to lick the flared head. It felt soft and warm and tasted suitably salty. She opened her mouth, just barely able to take the head past her lips.

"Don't… hurt yourself down there…" Raxicas moaned. She felt a little distracted; Naomi's tongue had worked her hole looser, and Raxicas could feel it as Naomi's tongue slipped inside. Naomi wriggled her tongue and swirled it around, eating the demon's ass like she was starving. Naomi focused on her task with single-minded obedience, her face buried even more firmly in the demon's large red cheeks.

Megan felt the massive cock twitch in her mouth, continuing to leak pre as Naomi worked her magic. Megan, not even bothering to try to take it down her throat, focused on the head, swirling her tongue around it as she gently bobbed her head. She reached out a hand and fondled the demon's balls with her fingers.

Unbeknownst to either Megan or Naomi, Raxicas had been busy of late and was a little pent up. Their two-pronged assault advanced more quickly than anyone expected, and after only a few minutes, Raxicas started to cum. She reached down and clutched at Megan's head, grunting and groaning as she filled Megan's mouth with cum. It came out in thick, massive spurts, which caught Megan off-guard. The cock throbbed so hard it threatened to pop out of Megan's mouth, but she kept it firmly in place as she swallowed the demon's seed.

"Was my service satisfactory, Lady Raxicas?" Naomi asked, having finally stopped eating out Raxicas.

"I suppose… it was…" Raxicas panted.

"Y-yaay-" Megan started, before coughing. "Oh good lord, that was a lot ."

"So are you gonna give them that tour, then?" Zakyra asked, barely looking up from her desk. In their passion, they'd forgotten they were in someone else's office. If it bothered Zakyra, it didn't show on her face.

"Give me a few minutes." Raxicas said. "I'm not quite done yet."

"I'm home!" Naomi announced as she stepped into the living room. Her son Jeremy was sitting on the couch playing video games. Her youngest, Jake, was fucking her friend Claire up the ass.

"Hey, Mom." Jeremy said.

"Hey, welcome, ah, back!" Claire said.

"How was your trip?" Jake asked.

"I trust the boys behaved themselves." Naomi said, giving a sly smile as she watched Jake and Claire.

"They've been, ah, perfect little angels!" Claire said.

"Yeah!" Jake added, giving Claire's ass a smack. "Angels!"

"So, like, did the key thing work?" Jeremy asked.

"Oh, yes, it's perfectly safe." Naomi answered. "I'll bring you all along next time. I think we're overdue for a family vacation, anyway."

Notes:

Hey everyone! First fic of 2023 and boy what a doozy, huh?
I'll probably do a couple other ones in this vein, I *miiight* do a 'real' story across multiple parts (you'll still get your classic Collared Mom shenanigans thought, don't you worry!~). Mostly I just want to see what kind of weird things I can get away with before people start complaining. Cause I can make this *go places*.
This fic is also a bit of a crossover with a WoW one I published recently, called Ring of Lust! ( /works/43489332) It's got gangbangs and orcs! I'm also tempted to bring Zakyra and her friends in for some other stuff, I've had a few ideas. Unless someone loudly yells at me that they don't want this, they'll probably show up at *some point*.

Chapter 30: Aunt and Auntonomy

Summary:

Megan and Terry catch up about some changes in her life, including the arrival of her nephews!

Notes:

(See the end of the chapter for notes.)

Chapter Text

Session Start

[14:00] TheFool Hey you!

[14:00] TheFool How's you? Been a while, Megan

[14:01] OrgyMom Heya! Things have been weird lately but I'm good, hbu?

[14:02] TheFool I'm okay. What's been weird?

[14:03] OrgyMom Well, my nephews moved in with me, so that's been an adjustment!

[14:03] TheFool I didn't know you had nephews.

[14:04] OrgyMom I don't usually talk about my family, we don't get and it's distracting from the sexy stuff people care about :P

[14:04] TheFool Is everything okay?

[14:06] OrgyMom I think so. It's kind of a long story, but my sister and her… ex, I suppose, are having a spat and things got kinda heated and scary, so she left them with me. They're good boys, kinda shy. Things were weird at first but I think they're kinda used to it by now.

[14:07] TheFool Oh, I'm sorry to hear that. Does your sister know about your, um, lifestyle?

[14:07] OrgyMom Nope, but uh, the kids did beforehand. Perk of visiting Auntie Megan ;P

[14:08] TheFool I see. So how were things weird, then? They a little iffy with the sex stuff?

[14:08] OrgyMom It's a little bit of that, but I popped their cherries a while ago. More just kinda uncertain and inexperienced than unwilling, you know?

[14:09] TheFool Makes sense.

[14:09] OrgyMom But also like I said, kinda shy. Feel a little weird around other people. But they're getting used to the party atmosphere! Everyone's been nice to them :D

[14:10] TheFool That's good!

[14:10] OrgyMom They're fans of Jake's streams, too, and have been thrilled to meet him!

[14:10] TheFool Hard to dislike his streams, even I watch them.

[14:11] TheFool Actually, I think he mentioned last time that he was going to try to have you on sometime…

[14:11] OrgyMom Yeah! We're thinking maybe next week, I got some stuff set up for it, mwahaha.

[14:12] TheFool Oh? What kind of 'stuff'?

[14:12] OrgyMom Wanna see? ;3

[14:12] TheFool Sure!

A live feed of a camera starts, showing a top-down view above Megan. She's sitting backwards on a chair, wearing nothing but black stirrup leggings and a pair of high heels. She wiggles her butt a little for the camera.

[14:13] TheFool Oh, that looks cool!

[14:13] OrgyMom Thanks! I can control it a bit, too!

The camera zooms in, focusing on Megan's ass. It pants a little to show her back, then the top of her head, and pans back to her butt again before zooming out.

[14:14] TheFool Very cool. I don't hear any sound, though.

[14:15] OrgyMom Yeah, still working on a good mic setup. The one I normally use isn't really streaming quality.

[14:15] TheFool Ah, makes sense.

[14:16] OrgyMom And if you'll gimme a second…

The camera view switches to show a side-on view of Megan's butt.

[14:17] TheFool Ooo, fancy!

[14:17] TheFool Given it a proper test yet?

[14:18] OrgyMom Not online. Why, you wanna help? ;3

[14:18] TheFool Well, if you need the help, I'm always happy to pitch in.

[14:19] OrgyMom Regular paragon of self-sacrifice, you are

[14:19] OrgyMom Like my personal Jesus Christ

The camera switches back to the top-down view, and Megan turns to address someone else.

[14:20] TheFool Who's over?

[14:20] OrgyMom My nephews and a couple boys. The party's not for a while ;P

[14:21] TheFool Guess it's good to test the system out without being swarmed

[14:21] OrgyMom Yeah! Wanna test it out before putting it under load

[14:22] TheFool Or under loads, as the case may be.

As Megan types her response, a boy comes up from behind her and grabs her hips. He hesitates a moment, then shoves his cock into her pussy and starts fucking her.

[14:23] OrgyMom Why would you put the camera *under* the loads? D: it will get wet! And sticky!

[14:24] TheFool Good point!

[14:24] TheFool Tell your friend I say hi.

[14:25] OrgyMom its my nephew o:

Megan turns her head and says something.

[14:25] OrgyMom he says hi back ;P

[14:26] TheFool How's he doing? Looks pretty good from here.

[14:26] OrgyMom doin a good job!

The camera zooms in closer, focusing on Megan's ass. There's a closeup of her nephew's cock going in and out at a steady pace.

[14:27] OrgyMom how's it look on ur end?

[14:27] TheFool Looking good!

[14:28] TheFool I kinda wish I could hear it, sound would add a lot.

[14:29] OrgyMom so picky ;P

[14:29] TheFool Just saying!

[14:29] OrgyMom i know, rofl

The camera switches to a side view, showing Megan getting fucked in profile. Her nephew is more clearly visible; he has short brown hair, and looks to be about Jake's age. From this view, the camera catches the sway of her breasts as she gets pounded.

[14:30] TheFool Also looks good!

[14:30] OrgyMom thanks!
[14:31] TheFool You should tell him to put some more 'oomph' into it, though! It would look better for the camera!

[14:31] OrgyMom for the camera or for you? ;P

Megan turns her head and says something. Her nephew suddenly starts picking up the pace, gripping her hips tight and jackhammering into her pussy. Megan's face is ecstatic, and her whole body rocks back and forth much harder from the force.

[14:32] TheFool Looks like that was better for you, too!

[14:32] OrgyMom fuck you have no idea

[14:33] TheFool Surprised you can still type like that.

[14:33] OrgyMom im a woman of many talents ;3

With little warning, Megan's nephew suddenly thrusts deep inside her. The camera switches back to the top view, showing him balls deep inside her.

[14:34] OrgyMom Damn, he really liked that! One of the more powerful orgasms he's had o:

[14:34] TheFool You measure?

He suddenly pulls out, and cum begins to leak out of Megan's pussy.

[14:34] OrgyMom I mean, I can feel it, lmao

[14:35] OrgyMom What good aunt *wouldn't* make sure her nephews are having a good time?

[14:35] TheFool You raise an excellent point.

[14:36] OrgyMom They're both a bit of herbivores atm ;p little meek even once they're out of their shells. But they seem to like getting to play the carnivore every now and then.

[14:36] TheFool I imagine most boys their age do.

[14:37] OrgyMom We'll see if I can get 'em more comfortable with it ;P they're still a little too polite to really *take* what they want. Or even ask lmao.

[14:37] TheFool Best of luck!

[14:38] TheFool I, uh, I'm feeling a little spent after that, and I should clean up.

[14:38] OrgyMom Go wipe up your cumstains then ;P Nice seein ya!

[14:38] TheFool Take care!
[14:39] OrgyMom You too!

Session Close

Notes:

Hey everyone! Thank you all for 100k hits on Stories of a Collared Mom! I'm really grateful to all my friends and fans!
I didn't really have anything special in mind to celebrate, I was just working on this idea I had and the timing just kinda worked out. So I guess this is the 100,000 hit special? Also 30th chapter, that's kind of a milestone!
Next entry will probably be something with more of a real 'plot'. Also I'm a little undecided on if I want to flesh out Megan's nephews as characters, or if that would make too many people to keep track of. They'll appear in some capacity later, though!

Chapter 31: Butt Buddies

Summary:

Claire returns to explain pegging to Terry. Fun times are had by all.

Notes:

(See the end of the chapter for notes.)

Chapter Text

Session Start

[11:00] TheFool Heya, Claire! How you been?

[11:01] ClaireBear Hey! I'm good! How about you?

[11:01] TheFool I'm okay. At w*rk.

[11:02] ClaireBear Get off soon?

[11:02] TheFool Depends how this conversation goes.

[11:02] TheFool That was a pun.

[11:03] ClaireBear Oh, I see it now! That's clever!

[11:03] ClaireBear I'm off today, at least. Work's been picking up, lately.

[11:04] TheFool In a sexy way or in a not as fun way?

[11:04] ClaireBear In a more serious way, mostly. The boss has a lot of meetings!

[11:05] TheFool "Mostly"? Now I'm curious.

[11:06] ClaireBear Well, I'm his personal assistant, not one of the escorts, so I don't really do much sexy directly. Guests and clients find me a little off-putting!

[11:06] ClaireBear A lot of the sexy stuff I do is on my own time!

[11:07] TheFool Oh, so you're not, like, the official Horse Ball Drainer?

[11:08] ClaireBear Nope! I do that entirely for fun!

[11:08] TheFool But that's such an important task!

[11:09] ClaireBear I think they get their balls drained pretty regularly without my help!

[11:09] TheFool Do they get many visitors?

[11:10] ClaireBear The horses? Yeah, there's a few clients who really love them.

[11:10] TheFool I'm sure they'd appreciate having more regular visits!

[11:11] ClaireBear They probably would! Takes me a bit to prep for it, though.

[11:11] TheFool How long do you think it'd take you to drain all of them in one go?

[11:12] ClaireBear Oh, I've done that before! Honestly, they don't last very long, so that usually takes 20-30 minutes tops. It'd go faster if they formed orderly lines! Although if they were sentient enough for that, they might ask to go again.

[11:13] TheFool Wow. That's impressive. Ever think about doing stuff like on one of Jake's streams?

[11:13] ClaireBear We've talked about it, actually! But it'd be hard, we'd have to work out logistics. Might just pre-record stuff or something, I'm not sure.

[11:14] ClaireBear Speaking of Jake, he's coming over after he's done with school today!

[11:14] TheFool No doubt for a wholesome session of tutoring and watching a movie together.

[11:15] ClaireBear I mean, we might? Although, usually we just fuck each other in the ass.

[11:15] TheFool Sounds like the better date activity to me, tbh.

[11:15] TheFool Wait, each other?

[11:16] ClaireBear Yeah! Oh, maybe I wasn't supposed to mention it. Actually, I don't think he'd mind.

[11:16] TheFool Like, with a strapon? I've never been bold enough to try that…

[11:17] ClaireBear Yeah, a lot of guys find it emasculating. Which is a shame, it feels really nice!

[11:17] TheFool And he's into it? How'd you talk him into that?

[11:18] ClaireBear Oh, he asked Megan to try it at some point, I think. I wasn't the first one to peg him.

[11:18] TheFool Makes sense, the lad *is* pretty adventurous.

[11:19] ClaireBear He loves it! I'm not half-bad with a strapon, either, and he always cums a lot from it!

[11:19] TheFool So are you rough with him? Take 'revenge' on him at all?

[11:20] ClaireBear I don't think I fuck him that roughly? He's not delicate, so it's not like I hold back, but I don't try to break him either.

[11:20] TheFool Oh, makes sense.

[11:20] TheFool How do you decide who goes first? Coin toss?

[11:21] ClaireBear Oh, Jake always fucks me first. I prefer to receive, honestly, so it works out for both of us! Plus it's easier to get his first load out of the way like that.

[11:21] TheFool Oh, interesting. Sorry if I'm being nosy, by the by.

[11:22] ClaireBear Oh, you're fine! I don't mind at all!

[11:22] TheFool Well, if you'll indulge me another question…

[11:23] TheFool How do you know when to stop? Since your cock isn't real and can't cum, presumably.

[11:23] ClaireBear Oh, well, it stimulates me a little, but yeah you have a point. Usually I stop when either he cums or one of us gets tired and wants a break. Then we switch after!

[11:24] TheFool Makes sense. You two seem cute together.

[11:24] ClaireBear Thanks!

[11:25] TheFool Do you ever consider having 'real' dates with him?

[11:25] ClaireBear Honestly, not really. I can't do normal relationships very well, so just having a bunch of friends with benefits is pretty nice. They're all accepting of me, too!

[11:26] TheFool Oh, I see. Well, I'm glad that's working out for you, at least.

[11:26] ClaireBear Thank you!

[11:27] TheFool Hang on, isn't he streaming later today?

[11:27] ClaireBear Is he? Oh, maybe he is!

[11:28] TheFool Hopefully I'll see you on there!

[11:28] ClaireBear Yeah, that'd be cool!

[11:29] TheFool Okay, well, I gotta head back for now! It was great seeing you! Hope to see you soon!

[11:29] ClaireBear You too! Byeee!

Session Close

Notes:

Hey all, I know this was a little short, but I hope you like it! Next entry is gonna be longer, so look forward to that in the next week or so~

Chapter 32: Naomi's Family Vacation Into the Unknown

Summary:

Naomi brings her family along to Hitoshi's hideout, but an carelessly open door leads to a strange world where nobody seems to mind their lifestyle. Well, *almost* nobody.

Notes:

(See the end of the chapter for notes.)

Chapter Text

Session Start

[20:00] TheFool Heya, Jake!
[20:00] JakeTheSnek Hey!

[20:01] TheFool How have you been? Loved your new stream by the way.

[20:01] JakeTheSnek Thanks!

[20:01] TheFool Any fun weekend plans?

[20:02] JakeTheSnek Yeah, actually! Mom got some weird key thing and we're gonna go on an adventure!

[20:03] TheFool What?

[20:03] JakeTheSnek Oh did she not mention it? Like at all?

[20:04] TheFool Nope. I don't know anything about a key.

[20:04] JakeTheSnek Uh. Do you know about the imp guy?

[20:05] TheFool …imp guy?

[20:05] JakeTheSnek Yeah, he came here from another dimension!

[20:06] TheFool …what.

[20:07] JakeTheSnek Okay, I know it sounds insane, but it's true! Some little imp dude visited us and he gave mom a little key-thing for Christmas that lets us also go to other dimensions?!

[20:09] TheFool …That's a lot to take in.

[20:09] JakeTheSnek Yeah, its nuts. Mom said she met a demon last time, it sounded awesome!

[20:10] TheFool Well. You'll have to tell me everything after your visit.

[20:11] JakeTheSnek I'm gonna take pictures, it'll be awesome!

[20:11] TheFool Maybe invite a demon to stream with you!

[20:12] JakeTheSnek I'll ask! I bet someone'd be interested.

[20:12] TheFool So is that sort of thing safe?

[20:13] JakeTheSnek Yeah, we've got a list of places safe to go to

[20:13] JakeTheSnek And also 3 places we're not supposed to go!

[20:14] TheFool Good thing I'm not you, I'd immediately try to sneak into those places. Do you know what's in there?

[20:14] JakeTheSnek Nope!

[20:15] JakeTheSnek I mean, I can guess what lives in the "Hornet's Nest" and the "Crawler's Burrow"

[20:15] JakeTheSnek …altho now I kinda wanna actually see what's in there myself…

[20:16] TheFool Well, fortune favors the bold!

[20:16] TheFool Actually, the guy who said that proceeded to sail a boat into a volcano and die, so maybe that's not a good motto.

[20:17] JakeTheSnek Still!

[20:17] TheFool You know what they say about curiosity!

[20:18] JakeTheSnek They call me curiosity cause i kill pussy

[20:18] TheFool LMFAO

[20:19] TheFool I shouldn't reward that. Anyway, be safe, don't do anything dumb!

[20:20] JakeTheSnek Okaaaay. If I'm on tomorrow, I'll tell you all about it!

[20:20] TheFool Woo!

[20:21] TheFool Its kinda late for me, so I'm gonna head to bed. Seeya!

Session Close

"Is everyone ready?" Naomi asked, standing in front of a closet door. Her family stood behind her, and an excited buzz seemed to emanate from them. Naomi and her daughter, Emily, were wearing only their collars. Her husband and sons were dressed casually.

"Ready as I'll ever be." Frank, her husband, answered. "Kids?"

"Yeah!" Emily said. "I'm excited!"

"I hope nothing eats our faces." Jeremy said.

"We should be fine." Naomi said. "Hitoshi gave his word that everywhere on this map is safe."

"Except the three bad doors." Jake said.

"Yes, well, except those." Naomi said. "Alright, well, no time like the present!" She stuck the key into the lock and opened it. It once again led to the inside of the abandoned mansion Hitoshi called home. Naomi stepped inside, followed cautiously by her family.

"Uh, Hitoshi?" Jason called out.

"Little imp-buddy?" Jake added.

"He might be further inside." Naomi said.

The six of them headed further into the house, but saw no sign of Hitoshi. Undeterred, Naomi led them to the hallway of doors she'd visited last time with Megan. Frank and the kids stared in slack-jawed awe of them as Naomi consulted the map.

"I suppose we could go back to the Ring of Lust, since we already know people there." Naomi mused. "Or we could try somewhere new."

"Where's that one lead?" Jake asked, pointing to a door at the end of the hall left ajar. It didn't look particularly mystical.

"Oh, that one leads to the room we're not supposed to go to." Naomi said.

"Why's it open?" Emily asked.

"Can we go see what it looks like in there?" Jason asked.

"Well, I guess there's no harm in looking …" Frank said. "Alright, just a quick peek."

They crept to the end of the hallway and peered inside the open door. As depicted on the diagram, three doors stood on the opposite wall, each painted red. One door, the one on the right, was also slightly ajar, and light was pouring in from the crack.

"I think perhaps it's best we head back." Naomi suggested.

"Don't you wanna know what's behind that door?" Jake asked. "Which one is that one?"

"'Hornet's Nest', according to the map." Naomi answered.

"I suppose we should go close it." Frank said, entering the room. "Maybe I'll take a little peek inside before I do that, though.

"Be careful, Master." Naomi cautioned.

Frank slowly walked up to the door, the floor creaking beneath his every step. The other four watched nervously. The tension felt thick and hot, and their hearts pounded in their chests as they watched Frank reach the door and poke his head in. He looked confused, then poked his head into it.

"Dad, is it safe?" Jeremy asked.

"What do you see?" Emily asked.

"It looks… normal. " Frank said. He motioned for his family to come over and opened the door.

On the other side sat a parking lot in the noon sun, adjacent to a street with a few cars going by. There were a couple pedestrians on the sidewalk, who didn't seem to pay Frank any mind. It looked like a normal scene from somewhere in Southern California, although none of them could immediately place exactly where.

"This place doesn't seem all that scary." Jake said, looking through the door.

"Hitoshi did say that they only might be dangerous…" Naomi said.

"Do you think we could, um, get away with stepping outside?" Emily asked. "Y'know, with the lack of clothes and all?"

"Well, I guess there's only one way to find out." Frank said. "You two, outside!"

"Yes, Master." Naomi and Emily said in unison.

They tentatively stepped out into the parking lot. A few people glanced at them, but nobody seemed particularly bothered or unnerved by their nudity. Naomi turned around to the door.

"I'm not sure anyone cares, Master." She said.

"Alright, well, maybe we'll have a little jaunt here." Frank said. "Seems like we can get away with a lot."

The boys stepped out of the door, joining the girls. Together, they made for the sidewalk and started walking with the other pedestrians. Absolutely nobody paid them any mind besides cursory acknowledgement of their existence.

"So, we're not ghosts in this world, right?" Jake asked. "I think people can see us."

"I think so." Jason replied.

"I admit, I've always wanted to try walking around in public without clothes." Naomi said. "Rather more dangerous, back home, of course."

"Maybe we can do more than just walk around naked." Emily suggested.

"Not sure how we'd find out without-" Frank started, before stopping as something caught his eye. His family stopped with him, confused at first, but understanding once they followed his gaze.

Someone , it seems, had noticed their peculiarity. A woman heading the opposite direction was staring at the six of them, looking very concerned. She was tall and chubby with a bit of a tan, and wore a large red hibiscus in her black hair. She had on a blue sundress with a berry pattern on it and a pair of sandals, and held a bag full of junk food in one hand.

"Um, hello there, Miss." Frank called out.

"Uh. Heya." The woman replied cautiously. She continued to stare at them.

"You seem to be the only one who thinks we're unusual." Naomi said. "I'm Naomi, by the way. What's your name?"

"Max," the woman answered, "and, uh, yeah, that makes sense. Not, uh, terribly self-aware, this bunch."

"Do you know Hitoshi?" Jake asked.

" Oh , are you friends of his?" Max asked. "I, uh, figured he'd have told you not to wander in here."

"Well, he did …" Jake admitted.

"He left the door open and we just poked our heads in." Frank explained. "It didn't seem all that dangerous, at least."

"He didn't really say what was in here." Naomi added. "Forgive me, but do you know more about this place?"

"Or the other two?" Emily asked.

"I… see…" Max mumbled. "So. Uh. Did Hitoshi tell you about The Accord?"

"I don't believe he's mentioned it." Naomi answered.

" Fuck ." Max muttered. "Okay. Didn't bring up The Accord. That's. Hrm." She looked down at her bag, emitting a strange noise with her mouth as she mentally calculated whether or not it was worth it to tell them.

"Is that like the Rising Moon?" Naomi asked.

"Okay, he did explain that , at least." Max said. "Alright. So. Short version: The Rising Moon is a god that wants to kill everyone and turn them into monsters and zombies. The Accord is a group of three gods and their various friends who would rather everyone not be monsters and zombies."

"Oh, so they're like, the good guys, then?" Emily asked.

"Eh. I guess." Max answered. "Although they're not all… great . And you, uh, kinda wandered into the stamping grounds of the worst one."

"It doesn't seem so bad here." Jason said.

"Yeah, I thought there'd be a bunch of bugs from the name." Jake added.

"I mean, there are if you know where to look." Max said. "Grand Inquisitor Vespa lives in a big ol' fort over that way. She and her underlings can turn into bugs, hence the name."

"What's so bad about her?" Jake asked.

"Uh. She's a really violent thug?" Max responded. "Although you're… probably safe. She's not exactly omniscient."

"What about these people?" Naomi asked. "Who are they?"

"Uh, Her Unholiness kinda got lazy when making her little pocket dimension, so they won't respond to much." Max answered. "So, y'know, do whatever it is you're into, they're not gonna care. They just kinda wander around to fill up space."

"So, what are you doing here?" Jake asked.

"None of your business!" Max answered in a strangely cheerful tone. "Speaking of which, I got a thing to go do and I don't wanna be late. Seeya." She set off at a brisk pace, continuing along her path without so much as a wave.

"I suppose we probably shouldn't come back after we're done here." Frank said.

"True, although since we're here and we're probably fine, might as well make the most of it." Jason suggested. He took a quick look around, and noticed that they were standing next to a small strip of grass in front of a little building. "Mom, Em, get on your hands and knees on the grass over there. Make sure you're facing the road."

"Yes, sir." Naomi and Emily said. They did as they were told, dropping to all fours on the soft green grass. They watched nervously as people walked by, barely paying attention to them. Their hearts pounded, afraid that at any moment the crowd would suddenly turn on them and become unpleasant.

"You're sure they're not gonna care?" Emily asked.

"Only one way to really find out!" Jake said as he unzipped his pants and got into position behind his mom. Emily did not find this reassuring.

"I think if anything bad was gonna happen, it would have been with that Max girl." Jeremy said. He took up a position behind his twin sister; Emily found the feeling of his hands on her hips strangely comforting.

Both boys pushed inside, and nervously started thrusting. Some people walking by looked over at them curiously, but otherwise they didn't seem to care.

"Little weird to be able to do this without needing a lookout this time." Jason said to his dad.

"Yeah, it's pretty surreal." Frank agreed. "How are my girls holding up?"

"Very, ah, good, Master!" Naomi replied as she got fucked.

"Kinda weird, but I'm, ah, okay, Master!" Emily added.

"Boys, c'mon, you can do better than that!" Frank said. "Put some 'oomph' into it! Don't be so nervous!"

"Alright, fine! " Jake said. "Here goes nothin'!" He started slamming into Naomi harder, causing her to moan louder. A passing pedestrian gave him a cheer. Jeremy quietly shrugged before increasing his tempo to match his brother.

"Ah, fuck! " Emily shouted. " God , that's so good!"

"Attaboys!" Frank said. He turned to Jason, his eldest son. "Wanna make it a pair of spitroasts?"

"Sure, which one do you want?" Jason asked.

"I'll take my wife, you take your sister. Sound good?" Frank suggested.

"Deal!" Jason agreed.

The two of them got their cocks out and approached the girls from the front. Frank grabbed Naomi's head forcefully and started to fuck her face. She gagged a little, and let out muffled moans as she got fucked from both ends.

"Take it you're, ah, not just gonna, ah, watch?" Emily asked as she saw her older brother draw closer.

"Nope!" Jason answered. He pressed his cock to her lips, and Emily obediently started sucking on it.

"We should take more trips like this!" Jake said.

"Yeah, doing this outdoors is fun." Jeremy added.

"Nice to see people appreciating some wholesome family bonding." Frank noted as he looked around. He waved at a passerby, who waved back and smiled. "This is my kinda place!"

The excitement of it all got to them sooner rather than later, and after a few minutes, the guys started cumming. Jake grunted as he unloaded his balls into his mother, before quickly pulling out and flopping onto the grass. Jeremy followed soon after, and both mother and daughter were left side by side with cum dripping out of them as they sucked cock in broad daylight.

Frank and Jason both shot their loads into Naomi and Emily's throats a couple minutes later. Both girls swallowed dutifully, then collapsed onto the soft grass once they were done.

"Dang, I forgot to take pictures…" Jake lamented. "I promised Terry!"

"Well, if you promised him, I suppose we should really give you another opportunity to take some." Naomi panted.

"We can probably stay a little longer." Frank said. "C'mon, let's go find a park!"

"Any questions, Inquisitor?" Hitoshi asked in his native Japanese. He was seated at a table across from a woman in a dark coat with an orange lining, and a capotain with a firefly emblem on her head.

"No further questions." The woman answered curtly, peering over her glasses. Her Japanese was more formal next to the country bumpkin Hitoshi. "The Inquistion will consider your debt repaid."

"That's good!" Hitoshi said. "Well, if that concludes our business, am I free to go?"

"Hi-to-shi!~" A voice called out in English as its speaker entered the room. A black-haired woman wearing a red hibiscus and a berry-patterned sundress walked in, holding an open bag of pretzels. "Guess what I just ran into!"
"Uh, what, Max?" Hitoshi asked nervously.

"Well, it was the weirdest thing!" Max continued. Hitoshi's anxiety only grew as she kept talking. Max was using a sort of unnatural innocence in her tone, the kind that usually preceded a violent outburst. "There was some family that had made their way outside, but some of them were naked! They didn't have clothes! And it was the girl-ones, too! They had collars on, Hitoshi! That was weird! "

"Oh, uh, I see ya met Naomi, then." Hitoshi replied. "She's, uh, a friend o' mine!"

" She's the one you gave our key to, huh?" Max asked, tilting her head as she stared down at Hitoshi. "I wonder why you'd do that!"

"I-I didn't mean any offense, Your Unholiness." Hitoshi pleaded. "S-s-still, even if you, uh, don't condone her lifestyle-"

"Y'know who does condone her lifestyle?" Max asked, before she started shouting. "A couple hundred fucking people on AO3, that's fucking who!"

"W-what's that have to do with-" Hitoshi started.

"Have you seen the kind of hits her stories get?!" Max screamed. "She's up to six fucking digits! It's no fair! I want a hundred thousand hits! She doesn't even have nearly as much backstory as I do!"

"That's probably what people like about her, Maki-chan." The other inquisitor added. Her voice became softer, and her English had a slight accent to it. "People like things that are easy to understand, and the 'submissive mom' angle is pretty easily digestible. We're a little more complicated . We don't have that kind of simplistic appeal!"

"Grr…" Max let out a low growl, baring her teeth. "I'd have fucking offed the lot of them if that wouldn't get me remembered as 'the weird OC nobody likes who killed the character we do like'."

"You're so violent , Maki-chan!" The other woman said with a smile. "There's other ways of bringing down your enemies."

"So, what would you do, Mugi?" Max asked.

"Oh, easy." Tsumugi answered. "There's one thing guaranteed to kill a long running series." She continued. She pushed up her glasses along the bridge of her nose, causing the lenses to reflect the a bright white light that hid her eyes. " Rewrites. "

Notes:

I feel I should make a disclaimer that Max's opinions are her own.
Hope you're all finding this amusing, cause I'm enjoying writing this!

Chapter 33: Fancy Footwork

Summary:

Jason and Sai have some footjob fun~

Chapter Text

Sai was sitting on the couch, working on her laptop, when she heard the front door open. Her eyes glanced over to the clock on her computer. School's out, hardly noticed . The corner of her mouth curled into an imperceptible smile as she heard two sets of footprints approach the living room.

"Hey, Mom." Rag said as he walked in. He sat down at a desk and started taking homework out of his backpack.

"Heya, Sai." Jason said as he approached her.

"Hello there, boys." Sai said, closing her laptop and looking up at them. Jason stood over her.

"How, uh, are you?" Jason asked.

"That depends, is this a genuine inquiry as to my well-being, or a conversational nicety?" Sai asked.

"Second one, if I'm being honest." Jason admitted.

"In that case, I'm horny." Sai answered matter of factly. She lay down on the couch; Sai was wearing a slightly frilly blouse and a pair of jeans, cut off a few inches above the ankle. It showed off her shiny purple nail polish, and the rings she wore on her toes.

"Me too!" Jason said as he sat down on the edge of the couch and unzipped his pants. "We're so in sync. Rag, are you also horny? You could add in 'me three'."

"I hate you sometimes." Rag replied, not looking up from his homework.

"No one's saying you can't join." Sai said. She grabbed Jason's erect cock with her feet, stroking up and down along the shaft with her toes. "You might even cum if I suck on your cage."

"I'm not falling for that." Rag said.

" For now ." Sai added. "You always seem to give in eventually."

"Kind of a shame you won't join us, man." Jason said as Sai worked his cock with her feet. "Your mom's really good at this!"

"Not like he'd get much out of it." Sai chimed in. She gripped the base of his shaft with the toes on her left foot, and rubbed the bottom of her right all over the slick head.

" Fuck , that's so good!" Jason groaned. "Oh, yeah, you got a point! It's one of his caged weeks."

"You two are terrible together." Rag muttered.

"I don't see you leaving." Sai pointed out.

"Oh, I told him he had to stay." Jason said.

"And I thought I was the evil one here." Sai remarked. "Then again, I've seen how you treat your own mother."

"Hey, if she wants to be a whore, I'm gonna fuck her like one." Jason replied. "Not that you treat her any better."

"Oh, I wasn't judging you." Sai clarified. "It's why we make such a good couple."

"For the last time, I'm not calling him 'Dad'!" Rag exclaimed.

"What's wrong, son?" Jason asked with a smug grin. "Ah, shit, I'm getting close…"

Sai used her toes to work the head of his cock to orgasm. Jason started to grunt and groan as he came, oozing his seed all over Sai's feet. It got all over her toes, adding an extra white coat to her purple nail polish.

"You're so much better than Mom at that, it's almost scary." Jason said.

"You should make her practice more." Sai suggested.

"Okay, are you done now?" Rag asked, looking up from his homework.

"Not quite yet." Jason said. "Haven't managed to get you to beg to join us, after all."

Chapter 34: Return of the Max

Summary:

Naomi and her family are planning their next trip, but get a sudden visit from an unexpected guest with a grudge. Will Naomi and her brood save the day, or will they succumb to Max's petty revenge?

Notes:

(See the end of the chapter for notes.)

Chapter Text

Naomi and her family sat around in their living room, discussing their next outing across spacetime. It had been a few days since they'd gotten back from their journey into the supposed "Hornet's Nest", and they'd been talking nonstop about what to do next ever since. Nothing had been quite like it, and the possibility of even more strange and exotic destinations enticed them.

"Mom, you said one of them has like, orcs and demons and stuff, right?" Jake asked. "I wanna see that one!"

"You think the orc girl will let us bang her?" Jeremy asked.

"Megan and I got the impression she was amenable to the idea." Naomi answered. "Or at least, she wouldn't say no."

"Could we go see her?!" Jason asked.

"Right now?" Naomi asked. "We should at least wait for your father to get home."

"Maybe we should ask Megan to come with, too." Emily suggested.

"She would make for a good diplomat to new people and places." Naomi agreed. "She's certainly the most sociable in our friend group!"

"This is gonna be so much-"

Before Jake could finish, the door to the hallway suddenly opened. Everyone's heads turned to watch, confused looks on their faces. From out of the doorway stepped a familiar woman, tall and stocky with a red flower in her hair. Instead of her cute little dress, though, she wore a dark blue jacket, leather gloves, and a dark pair of long pants.

"Howdy there, friends!" Max announced as she walked in. "Whatcha up to today? Weird incest stuff?"

"What are you doing here?" Naomi asked, standing up to confront Max. A long-dormant instinct stirred within her at the presence of this intruder.

"What, your old pal Max can't stop by and say hi?" Max asked, feigning hurt. As she spoke, a second woman stepped through the door, wearing a capotain, a black coat with a thin orange lining, a pair of boots, and white gloves. Her eyes looked stern beneath her glasses. "Oh, I brought my girlfriend! Her name's Tsumugi!"

"Who are you really ?" Naomi asked, narrowing her eyes.

"I told ya, I'm Max!" Max replied cheerfully. Her smile became a cruel grin. "Maxine Antoinette Vespa, Grand Inq-"

"Your middle name is 'Antoinette'?" Jeremy asked. "Like. Your parents really named you that?"

"N-nuh-uh!" Max replied defensively, immediately deflating the tension in the room. "I picked it myself!"

"You named yourself that?" Emily asked. " Why? That's worse!"

"C-cause it…" Max replied, looking awkwardly at the floor as she mumbled incoherently.

"Sorry, what?" Jake asked.

"Look, it's not important!" Max insisted. "What's important is that I've lived in your shadow for too long! You guys get way more hits than I do! It's not fair! "

"And what precisely do you intend to do about it?" Naomi asked.

"Well, I can't just bump all of you off, because a) you're popular and everyone would hate me for killing you, and b) you probably have plot armor, anyway." Max explained. "But I don't have to-"

"Have you considered that you're less popular because you kill people?" Jason asked.

"It is rather off-putting." Naomi added.

"Murder is a wholesome, time-honored pastime!" Max countered. "Not that you're any better, what with all your incesting and your being underage! But that's okay, cause Max is gonna make it all better! Nobody's gonna want any more Collared Mom by the time we're done with you! It'll be all Max's Happy Funtime Brigade! Guh-huh-huh!" Her laughter sounded sickly and ghoulish, chilling Naomi to the bone. Her kids immediately recognized that it was a lame King Boo impression, however, and were not particularly affected.

"But, like, how? " Jake asked.

"Inquisitor Komatsuzaki, if you would do the honors." Max said with a grin. Tsumugi stepped forward, and everyone else suddenly became aware of the sheathed katana and massive revolver on her hip.

"It's simple, really." Tsumugi explained. "With my powers, I can emit rays of light that your brain interprets as-"

"Oh, I found another reason nobody likes you!" Jake said. "It's cause you have too much stuff to explain!"

"Yeah, like, we have cool sex." Emily added. "Pretty easy to understand. You seem to require more, uh, what's the word? Exposition?"

"This is all very confusing." Naomi said. "Do you all have powers, then? I'm very unclear."

"Mugi, do the thing!" Max ordered, having grown impatient.

"Hai, hai." Tsumugi sighed. She used her finger to push up her glasses, then fixed her eyes on Jake. Jake stared back at her.

"Why are you doing tha-" Jake started, before a bright flash of light came from the inquisitor's eyes. Jake recoiled, covering his eyes. "Ach! What the hell, that's so bri-" Jake suddenly clutched at his head, starting to feel dizzy. Memories and thoughts not his own started playing in his mind.

"What did you just do?!" Naomi demanded.

"I'm just bringing him in line with the more family-friendly image that Her Unholiness wants you all to live up to." Tsumugi started. "She's hoping to work you in as supporting characters in a series about her wacky slice-of-life shenanigans. Of course, since you have access to other worlds, we'll also be able to work in an isekai angle. Those are very popular right now, we have to cash in before the trend die-"

"Onee-chan!" Jake shouted, using slightly questionable pronunciation. "Bet you've got a really lewd body under that coat, huh, Onee-chan?"

"W-what?!" Tsumugi asked, looking shocked. "Th-that's not supposed to-"

"Mugi." Max said, using all her might to contain her anger. "If you did what I think you just did, I'm going to be very unhappy."

"J-Jake?" Naomi asked. Her son didn't seem to pay her any mind. "What did you do to my son?"

"Something must have gone wrong with the personality impla-" Tsumugi started.

"It doesn't 'go wrong'!" Max countered. "Also, that's very clearly your crappy hentai dialogue coming out of his mouth!"

"Hey, my dialogue is fine!" Tsumugi insisted.

"You shouldn't be hiding a body like that, Onee-chan!" Jake said, running up and grabbing Tsumugi's tits. "That's no good!"

"Oh my god, this is hurting my ears." Max muttered, burying her face in her hands. "Y'know what, this is my fault, I forgot you're into the whole shotacon thing."

" No! We can't do that!" Tsumugi protested. "You're too young, Jake-kun! And I only like girls!"

"You just haven't had the right cock yet, you stupid dyke!" Jake replied, pushing her to the ground. Tsumugi pretended to put up a fight, although was hampered by Jake's somewhat underwhelming physical strength.

"Jake wouldn't say anything like that!" Naomi protested. "Give me back my son!"

"It's fine, it'll wear off." Max said. "I'll never understand why you like the orientation-play stuff."

"You have such huge tits , Nee-chan!" Jake said as he pulled down her top, freeing her large, soft breasts. "Your body's so lewd! "

"Oh my fucking god, I hate that so much." Max groaned. "Y'know what, I'm leaving, I'm not staying to watch while I get NTR'd by some snot-nosed brat." She turned to leave and opened the doorway, before pausing to turn around and point an accusatory finger at Naomi. "This isn't over! I'll get you next time, Gadget! Next time! " Before anyone could say anything, she left.

"What… just happened?" Emily asked.

"I bet you're already dripping wet for my underaged cock, you slut!" Jake said as he started taking off the inquisitor's pants.

"Your girlfriend has a point, Ms. Komatsuzaki." Naomi said. "Your dialogue could use a little work."

"Urusai!" Tsumugi ordered as Jake slid down her panties. "It's not my fault it sounds weird translated!"

"Get ready for my cock, bitch!" Jake said as he prepared to thrust into her. "I wanna see Nee-chan's lewd face!"

"What does that mean?" Emily asked.

"Stop asking questions, I can't focus!" Tsumugi replied angrily. "You're so big , Jake-kun! It's sho good! "

"He does get in quite a bit of practice." Naomi said.

"Your girlfriend can't compare to my shota cock!" Jake shouted. Tsumugi winced for a moment. Urgh, I should find a way to program in better pronunciation…

"I'm turning into your shota cock slut, Jake-kun!"

"Have you considered learning to write more natural-sounding English dialogue, Tsumugi?" Naomi asked.

"Jake is gonna be so embarrassed once he comes to." Jason said with a mischievous grin. He'd pulled out his phone and had been recording for a while now.

"I'm gonna cum!" Tsumugi shouted. "Nee-chan's lewd pussy is cumming on your shota cock, Jake-kun!" She pulled him close as she started to orgasm, bucking wildly as it tore through her body. Her loud screams triggered something she'd implanted, and Jake started to cum, too. "Your semen's so hot and sticky, I'm gonna get pregnant!"

"Are there non-lewd pussies?" Naomi asked, curiously. Tsumugi continued ignoring her. "Also, please do not get pregnant, I don't think I'd like to have you as a daughter in law."

"Yeah that's right, bitch," Jake started as he finished, "I'm- ugh, my head…" He clutched at his temples and then stumbled to his feet, leaving Tsumugi a collapsed, sweaty mess on the floor.

"Heya sport, how you doing?" Frank asked. "Heard you got brainwashed today."

"I feel… okay." Jake answered. "That stuff I said was so embarrassing! "

"Do you think we should take him to the doctor?" Naomi asked. "I'm not sure how we'd explain what happened, though…"

"You still feel woozy?" Frank asked.

"No, I'm fine." Jake answered. "It's probably gonna be okay."

"Alright, but if something feels wrong, you let us know, okay?" Naomi said.

"Okay." Jake replied. "Thanks, Mom and Dad." He sat up and left to go rejoin his siblings, leaving his parents alone.

"So, it seems we have an arch-nemesis." Frank said. "I knew you got up to fun without me, but this is a new level."

"I would not describe that as 'fun'." Naomi said. "I think we'll be safe, at least. She seemed disinclined towards violence, if nothing else."

"Well, that's good at least." Frank said. "I suppose we might have to keep an eye out for her on our next little trip."

"You still want to do those?" Naomi asked.

"If the worst we're gonna run into is an incompetent Saturday morning cartoon villain, I think we're gonna be just fine." Frank reassured her. "Say, don't you still owe us a trip to see your orc friend?"

"Oh, yes, I suppose I do." Naomi replied with a relieved smile. "I'll get on it at once, Master."

Notes:

Thank you all for putting up with my shenanigans! This is probably one of the stupidest things I've ever written, but it was funny and my friends liked it so maybe some of you will like it, too.
Just to explain something since I think there was some confusion: Collared Mom isn't going anywhere, this is not in fact the end of the series. I just had some dumb ideas and wanted to write them (I miiight do another entry in this little 'arc' but I'm not quite committed yet, I had one other stupid idea I'm very tempted to do). The power of incest has banished the wicked inquisition, and the world of Collared Mom is at peace! For now, at least...

Chapter 35: Wonder Twins

Summary:

A contemplative meditation on the nature of being and whether the pursuit of meaning in life is inherently pointless.
Just kidding, it's a quickie between my two twin characters, Emily and Jeremy! I wasn't sure how to summarize it though.

Chapter Text

"Hey Em, you busy?" Jeremy asked as he peered into the bedroom he shared with his twin sister, Emily.

"Uh, not really." Emily answered. She was laying on her bed, wearing only her collar and scrolling through her phone. "Why, am I about to be?"

"Just here for a quickie." Jeremy said. "Shouldn't be too long."

"Sweet." Emily said. "Hey, can we do it doggystyle? I don't want my phone to fall on my face."

"Yeah, that's fine." Jeremy answered as he undid his pants.

"Awesome." Emily said as she got on her hands and knees, sticking her butt in the air. "Jason and Jake could learn a thing from you."

"Mom doesn't seem to mind." Jeremy replied as he made his way onto the bed. "Neither do you , really."

"Well, it's fun sometimes." Emily admitted. "But it's nice that you're polite about it." She felt her brother grip her hips, then slide inside her with practiced efficiency. "Oh, fuck …" Emily muttered.

"I feel bad just yanking you away from something." Jeremy said as he fucked his sister at a steady pace. "Even if I can doesn't mean I should , right?"

"Yeah, that's, ah, fair." Emily replied, doing her best to talk coherently. "Y'know, you're kinda like, ah, Master."

"What, seriously?" Jeremy asked. He stopped for a second to process it. "Do you, uh, wanna have this talk after -"

"It's, ah, fine." Emily replied. "You're not doing it, ah, that hard anyway."

"Oh yeah?" Jeremy asked. He tightened his grip and started slamming into her, filling the room with wet slapping sounds. Emily grabbed a pillow and pressed her face into it, screaming into it to muffle the noise. She wasn't particularly ashamed, but the noise might have attracted her other brothers.

"Oh my God, yes! " Emily muttered. "Fuckin' fry my brain!"

Soon after, Jeremy started to cum. Emily let out a slightly disappointed "aww" as she felt his seed blast inside her. Her twin pulled out, and fell onto the bed as cum started to leak out of her and run down her thigh.

"Was that it?" Emily asked.

"I said it'd just be a quickie." Jeremy reminded her. "Anyway, what were you talking about earlier?"

"Oh, uh, that." Emily said, taking a minute to recollect her thoughts. "I just meant that, like, you and Master both have a kinda cool aura about you. Like, he's in charge and doesn't need to flex it, you know? Doesn't really take by force either, not the way Jake and Jason do."

"Oh, I guess I see what you mean." Jeremy replied.

"I think you could pull that off if you wanted." Emily said.

"So, what, should I make rules for you, too?" Jeremy asked.

"I'd be so down for rules from you, you have no idea." Emily admitted.

"What, seriously?" Jeremy seemed taken aback by the idea, then started to think. "Man, I'll have to think of something…"

"So, you want me to kiss your cock the way I do for Master, and if we're alone in our bedroom, I have to present myself for you?" Emily asked. "That's it?"

"Well, yeah, as standing rules." Jeremy said. "Plus, I'll try that stuff with more complex orders the way Dad does it."

"Yeah, alright." Emily said. "So, did you want anything else while you're here?"

Naomi came by her twins' room with a basket full of laundry ready to be put away. She knocked on the door, and Jeremy told her to come in. Inside, she found Jeremy sitting on the edge of his bed, and Emily on her knees obediently sucking his cock.

"Ah, there you two are." Naomi said. "Nice to see you having fun. Emily, could I ask you something?" Emily didn't acknowledge the question. Jeremy looked a little awkward.

"Well, you could , if you really-" Jeremy started.

"Ah, no, I understand." Naomi said with a smile. "'No talking until you're done', right? A slut's duty comes first." She winked at her son. "It's a better use for her mouth, anyway."

"Heh, thanks, Mom." Jeremy replied.

Chapter 36: The Pickup

Notes:

(See the end of the chapter for notes.)

Chapter Text

"Hey, honey!" Frank's voice rang out on the speakerphone as Naomi drove. "I managed to sneak out of work a little early. I'm already at the restaurant. Have you and the kids left already?"

"I've left, Master." Naomi answered. "The kids are at Sai's. I was just on my way to pick them up before heading over to meet you."

"Ah, alright." Frank replied. "Hope to see you soon, then! Give Sai my love!"

"Looking forward to it." Naomi replied. "And of course, Master."

A few minutes later, Naomi parked outside Sai's house. She stepped outside, wearing a modest dress and a pair of flats. She had on her collar, but it didn't look that conspicuous to passing observers.

Naomi approached Sai's front door and knocked. She heard approaching footsteps, then saw the door open to reveal her oldest son.

"Hey, Mom." Jason said. His clothes looked a little hastily put on. "You wanna come in?"

"Hello, Jason." Naomi said as she stepped inside. "Where are your brothers?"

"Living room, balls deep in Sai." Jason answered. "Wanted to get in one last bit of fun after we got your text."

"Ah, of course." Naomi said. "Well, I suppose your father would want them to wrap that up before heading to dinner." She paused briefly to look around. "Well, I suppose I should say hello."

Naomi made her way to the living room. Jason had been right after all; Sai was on the couch, getting double penetrated by her other two sons, Jake and Jeremy. Sai was moaning up a storm, and didn't seem aware of Naomi's presence. Sai and the boys were totally nude, although she had on the special little anklet she wore in lieu of a collar when it was her week to be submissive to her son. A more obvious piece of evidence that it was Rag's week in charge was that Emily, Naomi's daughter, had her lips wrapped around his uncaged cock.

"Hello, Rag." Naomi said. "Enjoying your freedom for the week, I trust?"

"Hey, Mrs. H!" Rag replied. "Jason said you guys were going somewhere?"

"Yes, we'll be going out to dinner after this." Naomi answered. "Is Emily's performance satisfactory?"

"Yep, she's doing a great job!" Rag said. "You guys have her really well-trained!"

"That's good to hear." Naomi said. "Emily, are you enjoying yourself, sweetie?" Emily raised an arm and gave a thumbs up, never breaking the rhythm as her head bobbed up and down in Rag's lap. "Wonderful."

"Look, boys, your whore of a mother is here." Sai said, turning her attention towards Naomi. Jake had a firm hold on her hair and was pulling it back, but she still somehow maintained her icy aura.

"Hey, Mom!" Jake and Jeremy said in unison as they continued pumping away at Sai's holes.

"Nice to see you too, Sai." Naomi replied. "Frank sends his love."

"How sweet of him." Sai replied.

"Alright, well, I'll wait out in the-"

"No." Sai ordered. "You stay here and watch your sons fuck me."

"Very well." Naomi replied. "You're rather assertive during your submissive week."

"Even as a sub, I'm above a slut like you." Sai said.

Naomi watched in obedient silence as her two younger sons fucked Sai. Sai moaned and screamed as both her holes got pounded. Her boys looked pale and pasty next to Sai's dark brown skin. Their cocks certainly stood out next to her wet, well-used holes.

After watching for a bit, Jake and Jeremy managed to cum at about the same time. They thrust deep into her and unleashed their loads, grunting and groaning as they throbbed inside her. Naomi smiled; she was glad her boys were enjoying themselves.

"All done, then?" Naomi asked as her two sons went to go put their clothes back on. She also saw Emily wearing her clothes, and having taken off her collar.

"Not yet." Sai said. "Your boys made a mess in me. Clean it up."

"Yes, Mistress." Naomi said. She opened her mouth and slipped her tongue into Sai's pussy. Naomi sucked and Sai pushed, forcing Jeremy's cum out of her hole. The taste was intoxicating, and Naomi started to get wet under her dress. Mindful of the time, though, she only did as she was ordered. After swallowing the cum from Sai's pussy, she moved to Sai's ass and swallowed Jake's cum.

"Very good girl." Sai said.

"Thank you, Sai." Naomi replied. "It was nice seeing you."

"You too." Sai replied. "And tell your husband I said hi."

Notes:

Hey, everyone! Been a while since the last update, huh?
Sorry it's been so long, I've been dealing with a lot of stuff IRL. It kinda hampered my mood to write more with these characters.
In better news, I also made a crappy little Collared Mom CYOA thing in twine about a month ago! It's an html file you'll have to download if you wanna 'play' it, and I recognize that this probably sounds sketchy as hell, but I promise I'm not gonna try to steal your identity or hijack your machine. Download is available here: file/d/1FlfE0bTbxvmhWPv1CNB4kcqK1ygQ6Kc2/view?usp=share_link
Hope you're all doing well and hanging in there. Hopefully there will be more regular CM content again going forward, but I can't promise anything. (Note: The series isn't going to *end*, but updates might get more sporadic)

Chapter 37: The Collared Mom Mother's Day Special

Summary:

Naomi's boys try to figure out what to get their mom for Mother's Day

Notes:

(See the end of the chapter for notes.)

Chapter Text

"So, like… what does Mom want for Mother's Day?"

Jason, Jeremy, and Jake sat in the living room pondering this question. Mother's Day was just around the corner, and they'd yet to procure any sort of present for her.

"You think maybe we should just… ask? " Jeremy suggested.

" Asking would defeat the whole point!" Jason said. "It would show we're not thoughtful!"

"Yeah, aren't presents supposed to be surprises?" Jake asked.

"Mom and Dad ask us what we want for birthdays and Christmas." Jeremy countered.

"I mean, I guess! " Jason conceded.

"Mom's just gonna say she wants us to be happy and that we don't have to get her anything." Jake said. "It makes getting her presents hard."

"Yeah, like, what would she actually find useful?" Jason asked. "Cooking stuff? Cleaning stuff? We can't buy alcohol…"

"You think she'd want sex toys?" Jake asked.

"I don't know, that feels like something more for us than her." Jeremy pointed out.

"Yeah, but she'd enjoy it too, right?" Jake asked.

"Yeah, and it's not like we have any better ideas." Jason said.

"We could do breakfast in bed!" Jake suggested.

"No, that's Emily's thing." Jeremy said. "She's the only one of us that knows how to cook."

"Well, I'm out of ideas." Jason said.

The three of them sat around making "hrm…" noises at progressively increasing volume as they failed to come up with any actual ideas. They assumed good poses for thinking, but it did not help them have useful ideas.

Then, Jeremy had an idea. It was a stupid idea, but it was the best one any of them had had. He stood up and looked for Naomi. It didn't take long; she was cooking in the kitchen, which made distinct noises and pleasant smells.

"Hey Mom, tell me what you want for Mother's Day." He said. "And that's an order."

"Oh, well, there's not really much I want for myself." Naomi mused. "As long as I can make my boys happy, that's enough for me."

"I knew you'd say that." Jeremy said. "That doesn't really help us pick out a present for you, though."

"You really don't need to." Naomi replied. "A good enough present would be an experience we can all enjoy together, don't you think?"

"Idunno, seems like kind of a bad present to me." Jeremy said. "'Hey, it's a special day to celebrate you, so here's your gift: my orgasm!'. Seems a little selfish."

"Oh, sweetie, your orgasms are all very precious to me." Naomi replied. Jeremy looked at her, she looked at him back. Jeremy started to giggle first, followed shortly by his mother.

"It sounds weird when you put it like that, but thanks. I think."

"Anytime, dear." Naomi said, returning to her cooking. Cooking being one of the few activities her sons weren't allowed to interrupt, Jeremy left to go report back to his brothers.

Naomi lay in bed reading a new book her husband had bought her when she heard the door open, accompanied by a vaguely metallic jangling sound. Her oldest son, Jason, stood in the doorway, holding some kind of chain.

"Hey, Mom." He said nonchalantly. "Happy Mother's Day! I got you a present."

"Oh?" Naomi asked, looking up at him. "Is that a new leash I see?"

"Yeah, we don't have any metallic ones." Jason said as he approached the bed. "I thought this might be a nice change of pace. Sit up, I wanna give it a try."

"Ooo, of course, sir." Naomi said. She put down her book and sat on the edge of the bed. Jason reached down and attached the leash to his mother's collar. He took a firm grip on the chain, giving Naomi only a few inches of leeway. "Shall I get your zipper for you?"

"Aw, aren't you a considerate whore?" Jason said. "Do it."

"Thank you~" Naomi smiled up at him as she undid his zipper with practiced efficiency. His rock hard cock sprang free, less than an inch from her face. Jason tugged the collar towards himself, and Naomi took the hint. She opened her mouth and started sucking her son's cock.

Jason pulled on the leash, forcing his mom to the base of his cock. Naomi let out a muffled noise of surprise as his cock slid into her throat.

"Hope you like the present." Jason said. "Seemed like a new leash would be the best way to celebrate you being such a slut. Don't you think so, Mom?" He looked down and gave her a slap across the face, leaving a red mark. "Can't think of a better present for such a depraved whore."

He let her up for air, and she panted hard to recover her breath. His cock was slick and shiny with her saliva, with a few strands connecting the tip to her lips.

"Alright, good enough." Jason said, forcing her back down on his shaft. With one hand firmly gripping the leash and the other clutching the back of her head, he started to fuck her face. There was a loud, wet "glug glug glug!" noise as he slammed into his mother's mouth. Saliva flowed past her lips and down onto his balls, which kept slapping against her chin. He pulled harder on the chain, and Naomi felt her collar pressing against her skin. Her mind felt fuzzy as it started to cut off blood flow.

Naomi wouldn't be long without air, though. Jason suddenly gave the leash a hard yank towards himself as he thrust into her mouth, forcing his cock into her throat as he started to cum. She felt the familiar pulse and throb against her tongue, and felt as his seed landed at the back of her throat. Jason kept her head in place with a strong grip for a few seconds, before finally letting her up for air. She coughed and sputtered as she got her breath back.

" Damn, that was good." Jason said. "So, uh, enjoy your present?"

"Oh, it was-" Naomi started, before being interrupted by a cough. "Sorry. It was wonderful! You boys should really slap me around more, haha."

"Noted, I'll pass that along to the Jake and Jer." He said. "Love you, Mom."

"Love you too, sweetie."

Notes:

Hey everyone! Happy Mother's Day!
Still dealing with stuff IRL so updates are gonna continue to be slow until things are settled.

Chapter 38: Wonder Twins 2: 2 Twins 2 Furious

Summary:

Emily and Jeremy hang out and have fun. Another quick one with them~

Notes:

(See the end of the chapter for notes.)

Chapter Text

Emily sat at her desk in her bedroom, surfing the net on her computer. She was supposed to be working on a school project, but had gotten distracted and fallen down a rabbithole on Wikipedia. Not much progress had been made, but she had learned quite a lot about various types of grasshoppers.

"Knock knock." Jeremy, her twin brother, said as he entered the room they shared.

"Who is it?" Emily asked, not looking up from the screen.

"Me, dummy, who else?" Jeremy replied. He set his stuff down by his bed then stood next to his sister, peeking at her screen.

"Oh, I wasn't sure if you were doing a knock-knock joke."

"Those are the lowest form of comedy."

"Idunno, I think some of them are clever." Emily finally looked over at him. "How was your thing? You guys have fun looking at rocks or whatever?"

"Eh, it was kinda interesting." Jeremy answered. "Wouldn't have gone if someone hadn't asked me to tag along."

"Not as fun as hanging around at home, huh?"

"Yeah, those rocks were a lot less sexy than you and Mom."

"Thanks, I think." The two of them laughed. "So, you just here to chitchat?"

"Well, I guess." Jeremy said. "You don't have your collar on, so, y'know…"

"So?" Emily grinned at him.

"Well, I figured you wouldn't wanna be bothered if you're not wearing it." He said. "You seem really into this grasshopper thing."

"Well, it's fine if you do it, Master." Emily said with a wink. "The collar's really just for Jake and Jason."

"True, but it still feels a little weird."

"Yeah, but that's why I trust you with it." Emily said. "You could put my collar on me if that'd make you feel better."

"Well, if you don't need it…" Jeremy stroked his chin as he looked contemplatively at his sister. "Get your tits out for me."

"Yes, sir~" She replied as she lifted up her shirt, revealing her breasts. "Hey, did we ever decide if you wanted to be 'Sir' or 'Master'? Or do you not really care?"

"Both of those work." He answered as he unzipped his pants. "I think Dad said it didn't really matter if I didn't want a specific thing." He reached down and grabbed her head with both hands.

"How about 'Your Majesty'?" She asked, looking up at him. "Or 'Your Holiness'?"

"Nah, too formal." He said. "Alright, open wide."

Emily opened her mouth, and Jeremy forcefully shoved his cock past her lips. He started to roughly fuck her face, causing her mouth to emit a loud, wet "gluk gluk" sound. His balls slapped against her chin, and her saliva quickly coated his shaft and flowed down to his nuts. She looked up at him, and he looked back down at her.

After a minute or so, he stopped to let her get some air. Emily panted heavily, her chest heaving as she caught her breath.

"Why do you keep staring me in the eyes?" He asked.

"Where else am I- cough , am I supposed to stare?"

"Fair point, actually. You good?"

"Mhm."

He went back in and started pounding her mouth again, filling the room with wet noises and covering her tits in her own saliva. Emily stared up at him stoically; her dad and brothers had fucked the gag reflex out of her a while ago. She reached down between her legs with one hand and started to rub herself through her panties.

After a few minutes, Jeremy thrust deep into her mouth and started emptying his balls down her throat. Emily tried to swallow, although it didn't do much besides stimulate the head of her brother's cock. His cum flowed directly into her stomach.

" God damn. " Jeremy muttered. "Alright, uh, good girl?" He said as he pulled out.

"You good?" Emily asked, before coughing.

"Yeah, I think so."

"Alright, well, if that changes, you let me know." Emily panted. "My duty to keep your balls empty, you know."

"Yeah, yeah." Jeremy said. "Hey, wanna see a cool rock I found?"

Notes:

Hey gang, happy Pride month!
I've got a few ideas for things, so expect a couple more stories this month~ Still dealing with things, but they're getting under control. Sorry again for the lack of updates (although I expect to have another story out later today)

Chapter 39: Like Mother, Like Son

Summary:

Jason pays a visit to Rag and Sai's place, but hooking up with his best friend's mom takes an unexpected turn when she suggests the two boys play together as well...

Notes:

(See the end of the chapter for notes.)

Chapter Text

"Hey, man." Jason said as he stepped into Rag and Sai's house. "How's it going?"

"I mean, besides the whole chastity thing, it's going okay." Rag said. "And, honestly, it's not that bad."

"I assume you wouldn't keep doing it if it wasn't kinda fun for ya." Jason said. "Where's your mom? Living room?"

"Yeah."

The two of them walked into the living room, where Sai was waiting on the couch. She had on a skimpy tank top and a skirt that went down to the middle of her thighs. She briefly glanced up from her phone at Jason, and patted a spot next to her to invite him to sit down as she typed something on her phone.

"Nice to see you, Jason." She said, eyes glued to her screen.

"Nice to see you too, Sai." He replied as he sat down.

"Give me a minute, then we can cuck my son."

"Should I watch, then, or can I go?" Rag asked.

"You always just watch." Sai noted, finally putting her phone down. "That's a little sad, don't you think? Maybe you should have a little more active role."

"Active… how?" Rag asked.

"You know, sucking cock, getting fucked, that sort of thing." Sai said matter-of-factly. "Seems like a pretty logical next step, like that nice Henry boy."

"I, uh, I don't know how Jason would feel about that…"

"Well, that'd be a new one, but I'm game." Jason admitted. "You don't really crossdress the way Henry does, but I guess this wouldn't be my first time with another dude."

"Well, I guess mine neither, but that'd still be… kinda gay, right?" Rag asked.

"You've swallowed his cum out of my cunt without complaining." Sai said. "This doesn't seem that much worse."

"Yeah, like Megan always says, who cares if it's gay as long as you're having fun?" Jason added.

"That is a good point…" Rag mused. "I, uh, didn't think you'd be so gung-ho about this, Mom."

"What? I don't care if you're gay." Sai said. "I'd have had more fun if I'd lezzed out some more when I was your age. Go nuts."

"O-okay…" Rag said, feeling at a loss. "So, uh, what do I do?"

"Strip." Sai ordered.

"Then come suck my dick." Jason added.

"Jeez, you don't have to be so pushy about it." Rag joked as he took off his clothes. His body was still mostly smooth; any body hair he had was more of a loose fluff. His small, plastic chastity cage stood out against his brown skin. Despite his trepidation, he was visibly straining against the cage. "Guess, uh, here goes nothing?" He said as he got down on his knees.

"Bet you'll be a natural at it, just like your mom." Jason said.

"What's that now?" Sai asked, glaring at him. Jason met her gaze.

"You heard what I said." He replied. " Slut. " They stared at each other for a few awkward moments.

"The balls on you." Sai replied, cracking a smile. "This is why I like you." She reached down and placed a hand on her son's head, forcing him into Jason's crotch. "Rag could learn a thing or two from you."

"Yeah, like how much he likes sucking dick." Jason replied.

"You two are awful together." Rag muttered. He took Jason's cock into his mouth; he expected it to have a stronger taste, but it wasn't particularly unpleasant. As he was getting used to having a hard dick in his mouth, he felt his mother's hand on his head again, gently pushing down.

"Suck that dick like you mean it, Rag." Sai ordered. "Don't make me look bad."

"Maybe you oughta go down there and show him how it's done?" Jason suggested. "You're doing great, buddy!" He added, turning to look at Rag and giving him a thumbs up.

"How greedy of you." Sai replied. "Oh, I suppose I should… "

Sai leaned down and, instead of providing any instruction, started licking Jason's balls. Jason leaned back and put a hand on each of their heads. Rag, having quickly adjusted, sucked on the shaft like a pro. Both Jason's shaft and balls were soon coated in saliva.

"You two work great together." Jason muttered.

"Thanks." Rag replied, lifting himself off his friend's dick. "Mom, wanna switch?"

"Actually," Sai said as she grabbed the shaft, "I have a better idea. You take one side of the head, I'll take the other."

"Wait, what?" Rag asked.

"Here." Sai started licking one side of Jason's tip. She swirled her tongue all around it, occasionally pressing her lips to it to kiss or suck on it. Rag tentatively followed suit, putting his mouth against the other side. As he licked it, his tongue occasionally bumped against his mother's. He felt weird about it at first, but it soon seemed as normal as anything else.

Under their combined might, Jason didn't last much longer. He suddenly started to groan as his cock throbbed between Rag and Sai's lips. Sai made sure her lips covered the tip, and Jason's powerful jets of cum sprayed in her mouth, landing on her tongue. As soon as Jason had finished, she pressed her lips to her son's, sticking her tongue in his mouth, much to Rag's surprise. She swirled it around a little, making sure to get the cum onto his tongue, before she pulled away.

"Be a good boy and swallow." Sai ordered. Rag did as he was told.

"Yes, Ma'am."

" God damn …" Jason muttered. "Well, thanks both of you!"

"You ready for round two, or do you need a minute?" Sai asked.

"Actually, I told Mom I'd be back soon." Jason admitted.

"Next time, then." Sai said. "I imagine your visits here are going to get a lot more fun…"

Notes:

Happy Pride Month!~
Next story will be #40, I might do something special for that, if I can think of something sufficiently cool.

Chapter 40: Talk Dirty to Me

Summary:

Megan and Tanya use the power of dirty talk to coax their shy nephews out of their shells!

Notes:

Hey all!
Just wanna give a heads up that I made an updated version of the Collared Mom CYOA Twine Game! I added more sex scenes to it!
Would anyone be interested in more projects along those lines? They're very fun for me to make :3
You can download it here (it isn't a virus, i promise!): /file/Ytl1WSbA#TQNDWVPI2TQakQs5Ei44RinaXsvaurr2Npl744JaIG0

Chapter Text

It was a quiet morning in the Amaranth household. Tanya lay in bed reading manga on her laptop. She heard footsteps quietly approaching her room and looked up. They sounded too light to be Megan or Juli's. Probably one of my nephews. She reasoned.

Sure enough, it was the younger of her two nephews, a blonde boy named Tommy. He and his older brother, Brady, had been staying with Megan for a while, although the boys were still rather shy. They enjoyed themselves well enough at parties or when friends were over, but clammed up a bit by themselves.

"Good, um, good morning, Auntie Tanya." Tommy said shyly. He was still in his pajamas, and an erection was visible through his pants.

"Good morning, baby." Tanya replied. "What can your auntie do for you?"

"W-well, I, um, I wanted to, um, ask if you could help take care of this…" Tommy said sheepishly, pointing to his crotch. "It's driving me nuts…"

"Aw, of course!" Tanya said. Man, these kids really gotta learn some self-esteem… "Whattya want?"

"U-um, like, on your back works…" Tommy said.

"Alright, can't go wrong with the classics!" Tanya replied as she lay on her back and spread her legs. Tommy threw his clothes off and climbed onto the bed, before climbing on top of Tanya.

"Thanks, Auntie." Tommy mumbled as his cock slid inside Tanya.

"Yeah, you like that, baby?" Tanya asked. She reached down and cradled his head. "It feel good?"

"Y-yeah, yeah it does…"

"You like fuckin' your Auntie Tanya's big black ass?"

"Y…yeah…" Tommy muttered. His thrusting paused for a bit.

"Lemme hear you say it."

"I… I like fucking my Auntie Tanya's big black ass…"

"Like you mean it!"

"I love fucking my Auntie Tanya's big black ass!"

The excitement got to him, and he started to cum. Tanya held him close as he emptied his balls.

"H-holy…" Tommy muttered as he caught his breath.

"You should try dirty talking more often, since you like it so much." Tanya said.

"B-but, um, I don't know, I don't wanna say anything weird…" Tommy said, "or, um, racist…"

"I'm gonna let you in on a secret, little man." Tanya whispered in his ear. "If your heart's in the right place, there's a lot of stuff you can get away with sayin'. Especially to your aunts!"

"O-oh, really?" Tommy asked. "Okay…"

"Alright, now how about you go get dressed, hrm?"

"Aw, that's cute!" Megan said as Tanya finished recounting her encounter with Tommy that morning. The two of them were talking in the kitchen, and neither was wearing much besides a pair of heels and their preferred stockings. "You think it'll stick?"

"Well, it might." Tanya said. "If not, maybe I just gotta repeat that lesson a couple times." They suddenly heard a tentative pair of footsteps approach the kitchen.

"Maybe you had some luck with it after all." Megan said.

Brady and Tommy stepped inside the kitchen. The former looked antsy, the latter looked nervous. In spite of that, Tommy put on a brave face.

"A-auntie Tanya…?" Tommy asked.

"What is it, baby?" Tanya replied.

"Is, um…" Tommy took a deep breath to steady himself. "Is that big black ass of yours free?"

"Oooo!" Megan and Tanya both looked at each other with excitement, before returning their gazes to Tommy. "And if it is?" Tanya asked, leaning down. "What do you wanna do with it, hrm?"

"I… I wanna bend it over the counter and fuck the shit out of it!"

"Mmm, now that is some powerful language there, little man." Tanya said as she stood up from her seat and faced the counter. "See if you can put your money where your mouth is!"

Tommy breathed a sigh of relief and climbed up on the chair. He gave Tanya as forceful a push over the counter as he could give her, then slid his cock into her pussy.

"Mmm, how's that big black ass treatin' you?" Tanya asked.

"So good!" Tommy answered. "I love how it jiggles when I fuck it!" There was a brief pause as he worked up the courage for what he wanted to say. "H-how's this white cock treating you?"

"Mmm, fuckin' amazin', baby!" Tanya said. "You fuck me so good!"

Brady looked at the pair of them, then looked over at his aunt Megan. He was pitching a tent in his pants.

"I can't believe that worked for him…" He muttered.

"You'd be surprised what you can get if you just ask, hon." Megan said with a wink.

"W-well then…" Brady muttered as he gingerly reached over and grabbed Megan's butt. "I… wanna fuck you doggystyle!"

"Sure thing, hon~" Megan said. She got on her hands and knees on the floor, and Brady came up behind her and started eagerly thrusting into her.

"Y-you're such a whore, Aunt Megan!" Brady said, not quite with the confidence of a shout. "This pussy's always getting fucked…"

"You're goddamn right I am!" Megan shouted. "Your Auntie's a whore for dick from little boys!"

A loud cacophony of shouting, moaning, and slapping noises filled the kitchen until the boys started to finish. They left Tanya and Megan as drippy, cummy messes. Both women stayed there after the boys pulled out, savoring the feeling.

"You boys should do that more often." Megan said.

"Yeah, you kids got hidden talent!" Tanya added.

"Th-thanks…" Tommy said.

"We'll, um, we'll try!" Brady added.

Chapter 41: Emma and Anna's Visit to LA

Notes:

Hey all, two things I want to say up at the top:
1) This story features two characters who belong to a friend of mine, Emma and Anna. I've written them before for comms, and I wanted to write this for them as a freebie. They will (probably) not be regular cast members, but I miiiight do a followup (if my friend is okay with it).
2) Per my friend's tastes, this fic contains depictions of (consensual) orientation play, use of slurs, and tit-punching. Reader discretion is advised!

Previous fics with Emma and Anna can be found here:
/works/40871118
/works/41979354
/works/47676388

Chapter Text

Session Start

[19:00] VillageSlut Hey, Jason! Just the guy I wanted to see!

[19:00] Jasunami Hey, Emma! What's up?

[19:01] VillageSlut Oh, nothing much ;) Just chilling with a glass of water. Added some lemon juice to help get the taste of piss out of my mouth.

[19:01] Jasunami Is it helping?

[19:01] VillageSlut I think so!

[19:02] VillageSlut Anna says hi :D

[19:02] Jasunami Hi back!

[19:03] VillageSlut How's your mom?

[19:03] Jasunami Good! Fucked her about an hour ago.

[19:04] VillageSlut Nice! We've got company over, they're taking a little rest atm

[19:05] Jasunami Nice! Take it you'll be busy tonight

[19:05] VillageSlut Hopefully ;)

[19:06] VillageSlut Oh, so, the reason I wanted to talk to you is that me and my girlfriend have a work thing in LA soon. You're near there, aren't you?

[19:06] Jasunami Mommy says not to meet strangers on the internet

[19:07] Jasunami But yeah, I am!

[19:07] VillageSlut I knew it!

[19:07] VillageSlut Idk, I've talked to your mom and she seems to like me ;P

[19:08] VillageSlut But yeah, things will be a little dull for us without any boys to keep us company. Don't suppose you and your brothers would mind stopping by our hotel room?

[19:09] Jasunami Hrm. So, I'm down, not entirely sure how my bros would feel about it. Jer's a bit of a softy, I don't think he'd be comfortable with some of the stuff you two are into. Jake's a little more adventurous, he might go for it.

[19:10] VillageSlut That's very fair! I wouldn't want to make them uncomfortable or anything. We can tone down some of the more extreme things, if you'd prefer.

[19:11] Jasunami Idk, I'm curious. Plus, uh, I get pretty rough sometimes. I'd definitely like to try some of the harder stuff you two are into!

[19:11] VillageSlut Alright! I'm looking forward to it!

[19:12] Jasunami Me too! I'll talk to my brothers about it too, but no guarantees.

[19:12] VillageSlut Appreciate it!

[19:13] VillageSlut Alright, our guests are ready for another round, so I'll be logging off for now. I'll send you the details as things get closer!

[19:13] Jasunami Okay, have a nice night! Tell your friends I say hi!

[19:14] VillageSlut They say hi to you, too! Bye!

Session Close

"Ugh, these are so boring! " Anna complained as she flopped into a chair in her hotel room. She'd stripped off her clothes the second she'd gotten back to the hotel. "It's hot and stuffy in those rooms, too!"

"At least it's over." Emma said. She kept on most of her dress suit, but decided to take off her pantyhose before putting her heels back on. "For today, at any rate."

"I miss the boys back home." Anna stared at the ceiling, then turned to face Emma. "Are your internet friends coming by, babe?"

"It's only one I actually talk to." Emma corrected. "Although he said he'd try to talk his brothers into it."

"You don't think they're gonna flake on us, do ya?" Anna asked. "That always happens when we venture too far from home."

"Not always. " Emma replied. "I guess a lot of guys are more vanilla than they're willing to admit."

"Maybe we scare them." Anna suggested.

"We probably do to some ext-"

There was a knock at the door, and the pair froze. Emma and Anna looked at each other with a hopeful glint in their eyes. Emma slowly approached the door and peered into the peephole. A grin spread across her face as she saw, through the distorted lens, two boys she recognized from pictures and videos she'd seen. Trying to contain her excitement, she made sure not to open the door too hastily.

"I don't remember ordering room service." Emma said, unable to suppress a smile. Jason's lips curled into an equally involuntary grin. "It's good to see you, Jason! Glad you could make it."

"Good to see you, too." Jason replied as he looked up at her. "You're taller in person."

"The heels add some extra height." Emma said. "I didn't think you'd mind. Come in, come in!"

"This is my younger brother, Jake." Jason said as the two of them entered the room.

"Heya!" Jake gave a little wave.

"Ooo, it's that kid from those livestreams!" Anna said as she noticed him. "You have a bunch of fans back home! I might have to get your autograph later."

"Your other brother couldn't make it?" Emma asked.

"Said he wasn't comfortable punching a girl." Jason said.

"I take it that means you two are? " Emma asked.

"I'm open to trying." Jason said.

"Me too!" Jake added.

"That's what we like to hear!" Anna said.

"So, you need a minute to get ready?" Emma asked.

"What I need ," Jason answered, "is for you to take your top off so I can use your sweater puppies as boxing practice."

"Yes, sir." Emma replied, smiling at him. She sat down on the edge of the bed and crossed her legs, slowly undoing the buttons on her top. "Oh, by the way, we got fresh pedicures before we arrived." She said as she showed off her shiny black nail polish. "I thought you might appreciate that."

"It's a little odd , don't you think?" Jason asked. "You care so much about what boys want, despite having a girlfriend."

"You think so?" Emma asked as she finished taking her top off. She reached behind herself to remove her bra. As it came off, Jason realized just how busty she was in person. "Well, there's some things boys just do better , I think." Emma gave him a wink.

"Like this?" Jason asked as he slapped her across the chest. Emma let out a delighted squeal as he smacked her chest.

"Nice warmup." Emma replied with a smirk. "Not too scared to use a closed fist, are ya?"

"No." He lied, trying to keep his cool. Alright, he thought to himself, here goes nothing. He wound up his arm and swung at her chest with all his might. His fist landed with a loud smack, which sent Emma reeling.

" Oh fuck! " She shouted

"Did I do it right?" Jason asked quietly.

"I am so fucking wet for you right now." Emma answered.

As Jason readied himself for another punch, Jake stood by Anna as the two of them watched. He looked at Anna, and Anna looked at him invitingly.

"Wanna give it a try, little guy?" Anna asked. She pushed out her chest invitingly.

"Sure, why not!" Jake answered. "It seems like fun!"

Jake threw a couple jabs in quick succession. They didn't land with a lot of impact, but he kept it up for a while. His fists moved quickly; he decided against shouting "ORA ORA ORA" as he punched Anna.

"I like the way your tits jiggle when I do this." Jake said.

"Prefer slow and steady to all at once, huh?" Anna asked. Jake threw a hard punch at her right breast. "Ow! Not bad, kid, not bad!"

"I could play with these all day." Jake remarked. "Or at least all night. Hey, I got an idea…"

Meanwhile, Jason's second punch had distracted Emma for long enough that he was able to grab her wrists and pin her against the bed. Emma made a token effort to resist, just enough to make Jason work for it. He looked down at her, and she looked back up at him.

"Aw, look at you putting up a fight." Jason said. "We both know you're gonna submit to me anyway."

"Oh yeah?" Emma asked. "Pro- Ah! " She was interrupted as Jason thrust inside her. He fucked her like an animal, showing her pussy no mercy. "Oh fuck , that's good!"

"God, you are wet for me." Jason muttered. "For a lesbo, you sure love cock."

"You gonna fuck me straight, Jason?" Emma asked.

Jason took a moment to mentally prepare himself. He had a response ready, but saying it felt vaguely wrong. Part of him worried he was about to go too far.

"Yeah I am, dyke ." The word felt awkward in his mouth.

"Yeah, c'mon and fuck the dyke out of me!" Emma begged. Jason took this as tacit approval.

"You say that like this loose, slutty pussy hasn't been reamed out by more boys than you can count." Jason replied. "It's a wonder you've got any tightness here at all, whore."

As the two of them carried on, Jake had moved Anna to the other side of the bed and was about to sit on her face.

"If you need air, I'm like half your size so just push me off." Jake said.

"You got it, boss!"

Jake sat down, burying Anna's face in his ass. She reached up and spread his cheeks apart so she could more easily tongue his hole. She licked at it hungrily, probing his ring with her tongue to try and slide it in. As she ate his ass, Jake punched straight downwards into her chest.

"Ya like that?" Jake asked. Anna nodded and gave an "mhm!". "Ya like eating boys' asses while they smack you around?" Anna gave another, more enthusiastic "mhm!", and Jake punched her again. She let a muffled yelp each time, followed by a low moan. "Oh, I get it, you're not really a lesbian, you just need the practice with your tongue for when you need to eat guy's asses." Anna squirmed, and Jake sat down harder on her face. "If you're a good girl, I'll cum on your tits!"

The two brothers went on abusing their partners like this for a while. It was intense, unlike anything they'd ever done before. They'd dominated and slapped around their mother and various other partners, but never before to this degree.

Jason growled like an animal as he came, thrusting deep into Emma and biting her neck. He wanted to breed her, to mark her as his with his seed. He'd had a line planned about that, but forgot about it in the throes of orgasm.

As the ecstasy passed, he found himself staring down at Emma, the two of them panting at each other. Jake and Anna were still going at it next to them.

"How are you feeling?" Emma asked.

"Kinda weird, to be honest." Jason admitted. "I feel a little bad about some of the things I said."

"That's normal." Emma replied. "You did a real good job, though! I enjoyed that a lot."

"I did?" That made him feel a little better. "Thanks. That was… certainly different from what I'm used to."

As the two of them talked it out, Jake started to cum. True to his word, he sprayed his hot, sticky jizz all over Anna's tits. Anna wriggled her tongue furiously inside him as he came, using one hand to play with his balls. As soon as he was done, Jake got off her to let her catch her breath.

"Man, I've always wanted to sit on someone's face." Jake said. "Thanks!"

"Mine's always free!" Anna replied enthusiastically.

"Y'know, I, uh, respect women and stuff." Jake said. "Just so you don't get-"

"Relax, I know." Anna said. "We can tell if you're an actual creep! The difference is stark! "

"Is it actually?" Jason chimed in.

"Yeah, it is." Emma said. "You two are good kids."

"Thanks, I think." Jason replied. After a moment, he realized something. "Dang, I have to pee."

"Peeing after sex is good for you." Emma said. " During is a little more fun, personally. Although, I'd be happy to serve as your urinal if you'd oblige me."

"You, um, sure that won't make a mess?"

"I'm a good girl, I won't waste a drop." Emma replied with a wink.

"Welp, okay, why not?" Jason said. "So, what do I-"

"Here, let's just-" Emma directed him to sit on the edge of the bed. She got down on her knees in front of him and put her lips around his flaccid cock.

"Alright…" Jason said as he tried to get over his performance anxiety. "Here goes nothing…"

He closed his eyes and started to empty his bladder. The warm, salty stream hit Emma's tongue at full force. She swallowed hungrily as it filled her mouth; not a single drop made it past her lips. Once he was done, Jason opened his eyes to the sight of Emma gulping the last of it down and smiling up at him.

"You're well-hydrated, that's good." Emma said.

"Lucky you, babe!" Anna said. "I'm a little jealous."

"I suppose I should share." Emma said as she stood up and made her way over to Anna before planting a sloppy kiss on her lips. Their tongues visibly writhed and intertwined.

"You two are cute!" Jake said.

"Thanks!" Anna replied.

"Are you staying the night, then?" Emma asked. "We have another day of this tomorrow, and we'd appreciate your company…"

"If I have to hear the word 'mission' one more time, I'm gonna fucking scream!" Anna grumbled as she and Emma made their way back to their room.

"I wonder how much all this summiting is costing the company." Emma mused. "Considering just how many people they're paying to sit around listening to this drivel for three days straight, it must be a pretty penny."

"That's Finance's problem." Anna said. "And it's two and a half days! We're outta here tomorrow at noon."

"They also have to pay for everyone's travel and hotel expenses." Emma added. "Finance is not going to be happy."

"Why couldn't we have a ski trip or something?" Anna whined. As they got closer to their room, Anna's mood improved. "So, you think our new pals are waiting for us?"

"Maybe, although we probably have to feed them first." Emma said.

"I could go for room service." Anna said as they approached the door.

"We'll see how they feel." Emma said as she put her hand on the door and started to open it. "Might not be a great idea to take them out-"

"Welcome back, sluts!"

Jason and Jake sat on the edge of the bed, both in the nude. Jason had set a chair up across from him. The pair had also set up a camera on a tripod, aimed roughly at the spot in front of them.

"You're not streaming this, are you?" Emma asked.

"Nah, this is a souvenir for us." Jason answered. "I thought you wouldn't mind."

"Oh, you know us so well." Emma said. "So, what are we doing for you boys today?"

"I never did give you a chance to show off that pedicure for me yesterday." Jason replied.

"How thoughtful of you." Emma said as she stepped out of her heels and sat down. She brought her legs up, able to comfortably place her feet in Jason's lap. She scrunched her toes to show off her shiny black nail polish again.

"We, uh, only had the one chair." Jake said, looking at Anna. "But, y'know, I'm not super picky!"

"Fine with me!" Anna said as she threw off her clothes. She came up to him and sat down on his lap, facing away from him. "Pussy's good, right?"

"Pussy's always good!" Jake said as he slid his cock into her.

"Ah!~ I like the way you think, kid!"

As the two of them started fucking, Emma used her feet to work Jason's cock. She rubbed her big toes against the sensitive head, which leaked precum all over.

"Sorry if my technique is a little lacking." Emma said. "This isn't quite as popular, back home."

"You're pretty good at this." Jason said.

"Thanks!" Emma looked over at the camera and grinned. "A proper free use slut should be able to make a guy cum with any part of her body, don't you think?"

"Amen to that." Jason replied.

"You boys should come visit us sometime!" Anna shouted as she bounced on Jake's cock. Her giant tits bounced with her in a way Jason found mesmerizing.

"Mom would probably like it." Jake said.

"So would you." Emma added. " All the women are free use, you know. Not just us!"

"We'll talk to Mom about it." Jason said.

The four of them talked idly, almost forgetting they were being recorded. Emma and Anna told them more about their small town, and Jake and Jason recounted some of their adventures with their mother and her friends. I might edit this out. Jason thought to himself.

"I'm getting close." Jason muttered. He was bucking his hips between her feet.

"Gonna give me a pretty little cumshot for your video?" Emma asked.

Instead of answering, Jason sprayed cum all over her. The first spurt hit Emma in the face, the rest landed on her chest and stomach. Only the final few dribbles got on her toes.

"Think the camera got all that?" Emma asked.

"I hope so." Jason panted. "You are good at that."

"Nearly done, too." Jake called out.

"Get the camera and go record your girlfriend getting creampied." Jason ordered.

Emma stood up and picked up the camera, then moved in front of Anna and Jake. She focused the camera on his cock slamming into her pussy. When he started cumming, Jake thrust deep inside her and grunted. His balls visibly flexed on the camera. When he pulled out, his cum dribbled out of her and ran down her thighs.

"How does that look, babe?" Anna asked.

" Gorgeous. " Emma answered. She lingered for a moment, then stopped recording. "Alright, anyone else hungry? Room service is on us, it's the least we could do."

Chapter 42: Recognized in Public

Summary:

Megan takes Naomi to a favorite bakery of hers, but Naomi finds a surprise waiting for her inside.

Notes:

(See the end of the chapter for notes.)

Chapter Text

"How have you never been to Charlie's?!" Megan asked as she parked her car.

"Well, there's quite a few bakeries nearby." Naomi replied. "I'd never known I was supposed to go to this particular one."

"Alright, fair, but Charlie's a friend!" Megan said. "And his cupcakes are to die for!"

It was early afternoon as Megan and Naomi approached the small bakery in a local stripmall. The lunch rush had just died down, and the place was empty save for the middle-aged Chinese man standing behind the counter and a boy sitting at one of the tables with his laptop open. Naomi thought he looked familiar.

"Megan! So nice to see you!" Charlie said. To Naomi's surprise, he didn't have an accent. "Who's your friend?"

"Heya! So, this is Naomi!"

"Nice to meet you, sir." Naomi said, giving a little bow.

"Ah, Naomi, I've heard so much about you!"

"Y-you have?" Naomi felt a little confused. "Good things, I hope."

"Of course, of course!" Charlie seemed ecstatic. "My son goes to Megan's parties, I hear nothing but good things about you."

"O-oh, I see, haha." Naomi laughed nervously.

"Eric! Look who's here!"

The boy sitting at the table took out his earbuds and looked up. Now getting a better look at him, Naomi did indeed recognize him from Megan's place. He waved at her enthusiastically.

"I don't think I've ever seen you with clothes on before." Eric said. "It feels kind of weird, like seeing your teacher at the grocery store."

"I imagine, haha." Naomi was at a loss for words. "Well, I assure you I do wear clothes at least sometimes."

"Hey, Dad," Eric asked, "can I take her to the kitchen?"

"Sure, it's fine with me!" Charlie answered. "Just be careful in there!"

Eric grabbed Naomi by the hand and led her behind the counter to a door that led to the kitchen. It was a small, somewhat cramped room, with tile flooring and shiny metal appliances. Eric left the door open a crack, and Naomi could hear Charlie and Megan talking.

"You let your boys order you around whenever they want, right?" Eric asked. "I wanna fuck you from behind!"

"Very well, sir." Naomi said as she got on her hands and knees. The floor was cold and hard, not nearly as comfortable as the carpet at home. Still, she didn't complain.

"Wow, I'm so jealous of your kids." Eric said as he lifted up her dress and slid down her panties.

"Haha, I hear that one pretty oft- ah! " Naomi let out a quiet moan as Eric's cock slid into her. She tried to keep herself quiet, although Eric certainly didn't seem mindful of it. The kitchen was full of wet slapping noises as his hips rammed into her ass. "You seem, ah, a little pent up…"

"I haven't jerked off all day!" Eric said. "You should let me come over so I can fuck you more!"

"I'll, ah, talk to your father about that, haha…"

Meanwhile, Charlie and Megan were talking in slightly hushed tones.

"She really does anything? " He asked. "Eric didn't even ask for her permission!"

"Yeah, she's a real freak like that." Megan replied. "Sometimes her kids don't even give her a heads up."

"...Do you think she'd let us come over sometime?"

"Probably!"

"And her husband is okay with all this?"

"Encourages it!"

"Your friends are very interesting, Megan."

The wet slapping noise in the kitchen stopped, and a few moments later, Eric walked out of the kitchen, looking like he'd just exerted himself. Naomi stepped out shortly after, her hair and clothes slightly disheveled but looking none the worse for wear.

"All done?" Charlie asked.

"Yeah! Thanks, Naomi!"

"Anytime, haha."

"Here." Charlie said as he handed a cupcake to Naomi with a wink. "On the house."

"Are you sure?" Naomi asked.

"A friend of Megan's is a friend of mine!" Charlie said. "I do hope you'll come again sometime."

"Oh, don't you worry," Naomi replied, "I intend to."

Notes:

Hey everyone, I've been in a little bit of a slump with CM stuff lately. Is there anything in particular you want to see from me?
I might do another story arc thing, I had some dumb ideas but nobody seemed to really mind last time I did that.

Chapter 43: Special Bonds

Summary:

Jason decides to make use of his mother, but seems to catch her in an unusually romantic mood...

Chapter Text

Jason sat at his desk, idly playing a tower defense game while listening to a podcast. He was getting a little bored when he heard footsteps outside in the hall. Sounds like Mom. He thought. His mother, Naomi, was always naked around the house. Thinking about it, he started to get hard, so he decided to go drop in on her.

As he opened the door, he saw her standing in the hallway adjusting a picture on the wall. She was indeed naked, with only her collar on. The only other arguable piece of clothing was the little chain connecting her nipple rings. She looked over at him and smiled.

"Good morning, Jason." She said.

"Hey, Mom." He replied. He reached out and hooked his finger on the chain, giving it a little tug. Naomi let out a little "ah!" and let out a hiss of air. "Watcha doing?"

"Mmm, careful with that." Naomi said.

"I'm always careful, aren't I?" Jason asked, giving the chain another little tug.

"God, you're so good at this." Naomi muttered, before suddenly leaning over to kiss him. Jason felt startled.

"I, uh, I thought you only did that with Dad…?"

"I don't think he'd mind." Naomi said. "We've discussed it, and it's not like he does that exclusively with me, either."

"O-oh. Okay." Jason said. "So that's just… on the table now?"

"Well, for you ." Naomi said, leaning in closer to him. "You're my oldest, after all. I like to think that gives us a special bond."

"I mean… I guess that makes sense…"

"That, and," Naomi paused, lowering her voice to a whisper, "you fuck me best."

"Do… do I actually?"

"You're quite the little sadist." Naomi said. "I'm very proud of you, you know."

"Aw, thanks!" Jason replied. His eyes darted around awkwardly. "Kind of, uh, killed the thing I had going, though. S-sorry."

"We could take this to your bedroom, if you'd like." Naomi suggested. "If you'd still like to make use of me, of course."

"Well, yeah. "

Jason grabbed his mother by the hand and led her into his room, closing the door behind him. Naomi sat on the edge of his bed as he quickly stripped his clothing before taking a seat next to her. He was rock hard, but he felt a little unsure of himself.

"Have you done this sort of thing before?" She asked.

"Uh, just with Sai a few times." Jason admitted.

"I suppose I don't have to teach you the basics, then." Naomi said. "Not that you have to if you don't want to. I'm yours to do with as you wish."

Jason grabbed Naomi and pressed his lips to hers, forcing his tongue into her mouth. Naomi let out a moan and reciprocated. Oh, he's a natural. She thought. Naomi put her arms around him and pulled him closer. She reached down with one hand and started to stroke his cock. They let out soft moans into each other's mouths for a bit before breaking the kiss.

"Damn, can't keep your hands off my dick, can you, slut?" Jason asked.

"Of course not." Naomi answered. "What kind of mother wouldn't want to keep her sons' balls empty?"

"Your pussy would do a better job of that, whore." Jason said, putting a hand around her throat. He pushed her onto her back, slowly tightening his grip as he got on top of her. "Not too tight, is it?"

"Little harder?" Naomi asked, spreading her legs. Jason tightened his grip further, and Naomi gave a strained smile.

"Of course you want it harder, slut." Jason said. He thrust into her; Naomi was already soaking wet, and let out a choked moan as he started to fuck her. "You're just a bunch of holes for your boys to use, aren't you?"

"Yes, yes!" Naomi gasped. "Mommy's such a slut!"

"You're always so fucking wet for me." Jason slapped her across the face, leaving a red mark on her cheek. It instantly brought her to orgasm, causing her to writhe under her son as she squirted on his cock. "Did you just cum from that?!"

"Mommy likes the pain, sweetie." Naomi choked out.

"I should be rougher with you, then."

"You should! "

Naomi wrapped her legs around Jason, pulling his hips closer to hers. He fucked her hard and deep, his cock threatening to poke against her cervix as he slammed into her. His bed rocked violently, although the sound was drowned out by the moans and screams of his mother.

Eventually, Jason came, He thrust all the way into her as his seed poured into her. His cock throbbed and pulsed, emitting powerful spurts of cum into Naomi's pussy. Naomi clung to him tightly, making sure he couldn't pull out until he was all done.

The two of them stared at each other as they caught their breath, looking into each other's eyes. Naomi reached up and gave him a quick kiss. Jason blushed.

"Satisfied, sweetie?"

"You haven't called me that since I was in like 3rd grade."

"Do you want me to stop?"

"I didn't say that." Jason said, averting his gaze. "And uh, yeah. That was good. Thanks, Mom."

"Anytime." She said. "And I mean that quite literally."

Chapter 44: Escort Mission

Summary:

Naomi's in need of a last minute babysitter to watch the kids, but Megan's a little busy. However, Megan's daughter Juli just so happens to be free that night.

Notes:

(See the end of the chapter for notes.)

Chapter Text

Session Start

[13:00] CollaredMom Good afternoon, Megan :)

[13:00] OrgyMom Heya! What brings you on?

[13:01] CollaredMom Had a little time to myself, haha. I was hoping to catch you, actually!

[13:01] CollaredMom Although, if I'm being a distraction I can just text you later :)

[13:02] OrgyMom Nah, I can multitask ;p

[13:02] OrgyMom the boys here say you should come over more often!

[13:02] CollaredMom Haha, perhaps. Full house already?

[13:03] OrgyMom Mhmm. and full holes! Me, tanya, and juli been busy today!

[13:03] CollaredMom But not so busy you can't chat? Haha :)

[13:04] OrgyMom hey, im taking a little break ;p sorta

[13:04] CollaredMom Sorta?

[13:05] OrgyMom just one cock counts as a break, right?

[13:05] CollaredMom I admire your dedication ;) And stamina!

[13:06] OrgyMom so whatd ya need from lil ol me?

[13:06] CollaredMom Francis and I will be out tonight, I was wondering if you could watch the kids?

[13:06] OrgyMom sure! Gonna drop em off?

[13:07] CollaredMom You're a bit out of the way from where we're going, sadly. If you can't, I understand.

[13:07] OrgyMom gimme a sec

[13:08] OrgyMom Alright, nice and fresh creampie~

[13:08] OrgyMom Yeah this is a bit last minute, and leaving Tanya by herself would be a little unfair to her :P And Jules is probably busy

[13:08] CollaredMom I understand, no worries. :)

[13:09] OrgyMom Oh, hang on! Juli's free tonight!

[13:09] OrgyMom Want me to put her on?

[13:09] CollaredMom If she's not wildly busy :)

[13:11] OrgyMom Hey Naomi! Just tagged mom into a triple penetration ;3 Heard you need a sitter?

[13:11] CollaredMom Oh my, sorry to drag you away from your fun! :( And yes, I do

[13:12] OrgyMom Don't worry about it~ What time should I show up?

[13:12] CollaredMom Does 5 work for you?

[13:12] OrgyMom Sure does! Had tonight's client cancel last minute so I'm basically free. Wooo!

[13:13] CollaredMom Okay, thank you so much! I'll let you get back to it, then :)

[13:13] OrgyMom Okay! Seeya tonight!

Session End

"Thank you so much for coming on short notice." Naomi said as she opened the door. She had on a nice dress for her party later that evening. "They didn't tell us this was a social event with spouses allowed until last night."

"Not a problem!" Juli said as she stepped inside. She had on a miniskirt and a cute little tank top, with a pair of sunglasses in her platinum blonde hair. Her sandals showed off her dark blue nail polish.

"Juli!" Naomi's kids called out as they rushed to hug her.

"Hey, guys!" She replied. "Man, I haven't been to your place in forever! "

"You kids behave yourselves and listen to Juli." Frank said as he and Naomi headed for the door.

"Everything will be fine!" Juli insisted. "Go have fun with your work stuff!" Naomi and Frank left, and shortly after they heard the sound of a car starting and driving away.

"What have you been up to?" Jake asked. "I feel like we never see you anymore!"

"I been hella busy with work!" She answered. "You guys wanna see pictures?"

"Yes." All four answered in unison.

"Well, c'mon, gather round! Gather round!" Juli said as she sat down on their couch and got out her laptop. She opened up a folder and started showing off pictures. "So this guy usually likes the whole girlfriend experience, but sometimes our 'dates' are a little… one-sided." She opened up a picture showing herself laying nude on a table.

"Is that… sushi on you?" Emily asked.

"Yeah! He's pretty into that. It's kinda hot, being used as a platter like that."

"Is that sanitary?" Jeremy asked.

"Are you insulting my hygiene, good sir?" Juli asked, feigning offense. "I kid, I kid! I shower beforehand so it's fine."

"Does it leave any weird residue?" Jake asked.

"Nope! Not the stuff he orders, at least."

"Do you get to have any?" Jason asked.

"Heh. Sometimes."

"I assume you fuck afterwards."

"Also only sometimes!" Juli explained. "Well, more often than not, but not always . The sex is kinda vanilla, anyway. Pays well, though."

"I'd have thought you'd do more parties."

"I love parties, but then you need a client that is both throwing a party and can afford the extra entertainment." Juli navigated to a different folder and pulled up a picture of her in a bikini by the side of a pool.

"Man, I wish we had a pool."

"That looks really good on you!"

"Thanks!" Juli said as she moved on to another picture, showing her and Jamie with their arms around each other in the water.

"Is, uh, Jamie a 'professional' like you, too?" Emily asked.

"Not really. She just tags along for some of these party gigs." Juli said. "Good way to earn some scratch and tease her poor boyfriend, hehe." She moved on to another picture, this one showing her and Jamie riding guys on pool chairs. They looked like they were talking to each other.

" Damn …" Jake muttered. "That looks like fun."

"I mean, I'd hope you'd remember from experience that it doesn't just look fun." Juli teased.

"I don't know, Jules." Jason said. "Been forever cause you keep neglecting us! I think we need a refresher!"

"I swear I remember seeing you guys at Mom's place like two weeks ago." Juli said.

"You only remember seeing us?" Jeremy asked.

"I mean, I assume we fucked." Juli said. "I'm kinda bad about keeping track of that stuff." There was a brief pause as the boys thought of what to say, but Juli cut them off. "You… you guys know we're gonna fuck tonight, right? Like, a lot? Whole reason I came over here, sillies."

"I don't know if we can afford your rate, though." Jake joked.

"Pfft. Dork. You get the friend discount, obviously!" Juli gave him a gentle bop on the head. "So, you guys need a little more inspiration , or are you ready to make some new memories?"

It was the dead of night by the time Juli got back home. The house was a lot quieter, unnaturally so. As she walked in the front door, she found Megan at her computer and one of her cousins playing video games on the couch.

"Have fun, Jules?" Megan asked.

"Man, those kids can fuck ." Juli said.

"You didn't burn their house down, did you?"

"Pretty sure it was fine." Juli said. "Unless they burnt it down and rebuilt it while I was out cold."

"Y'know, Juli, not to tell you how to do your job or anything, but generally you're supposed to be awake to watch people's kids."

"Oh, it's fine, I let Jason choke me out." Juli said. Megan looked impressed.

" Damn! Does he do that to his mother?"

"Yes, apparently." Juli said.

"I keep forgetting Naomi's a freak." Megan said. "She's just so unassuming."

"No, no, I get that." Juli agreed. "She's got a churchmom-ness about her. It's part of her charm, though!" She looked around a bit then started to head for her bedroom. "Alright, I wanna go to bed. Night, Mom!"

"Nighty night, Jules."

Notes:

Hey everyone! Dunno how well people remember Juli. She used to be a bigger part of this little 'verse but I kinda kept neglecting her. Oops. Hopefully people remember her and this doesn't feel like a new character coming out of left field.

A couple notes from me:
1) I marked the series as "complete", but it isn't actually "over" for now. I'm just not really building to anything in particular. Updates will continue whenever I have ideas.
2) My passion for this series has been in a bit of a lull lately, not helped by certain events I don't particularly want to get into. When I started Collared Mom, I had this idea that I'd alternate and do one CM entry between my other work. Updates are now just gonna be whenever I feel like it and have an idea I feel like sharing. It's not over, not by a longshot, and previous lulls have passed when I get invigorated.

Chapter 45: Afternoon Delight

Summary:

Naomi and Terry catch up during a particularly lazy afternoon

Notes:

(See the end of the chapter for notes.)

Chapter Text

Session Start

[15:00] TheFool Hey there! Good to see you, Naomi!

[15:00] CollaredMom Nice to see you as well, Terry :)

[15:01] TheFool How's the family? The boys keeping you well-fucked?

[15:01] CollaredMom They're well, and of course ;)

[15:02] TheFool Up to anything fun today?

[15:02] CollaredMom One of Jake's friends had parents out on errands today, so we swung by for a little bit of an impromptu party :)

[15:02] TheFool You do seem to go to an awful lot of parties

[15:03] CollaredMom Ha, I suppose, although there's a rather broad spectrum of what seems to constitute a "party"

[15:03] TheFool Oh yeah? Not all parties made equally?

[15:04] CollaredMom Haha, well, they differ based on their hosts, of course. But I'm not sure it's particularly well-defined. The word seems to be used somewhat loosely

[15:04] TheFool Better call up ISO and get them on that! Unless they already have a standard and you're just not using it…

[15:05] TheFool Actually that's a good point, what do you all call a "party"?

[15:06] CollaredMom Well, Megan's weekend shindigs count, naturally. And I daresay my sons and their friends can throw a decent party when they want to. But this thing we went to today didn't feel like much of a proper party, haha.

[15:06] TheFool Not enough hors d'oeuvres for your liking?

[15:07] CollaredMom Ha, well, the boys were in a bit of a rush. They wanted to finish while they had the chance.

[15:07] TheFool Not much small talk, then? The best part of a party, imo!

[15:08] CollaredMom Not really. My mouth was full for most of it, and they didn't seem wildly talkative ;)

[15:08] TheFool Not even so much as a hello?

[15:09] CollaredMom Well, they said *that*, haha. But they quickly hurried me to the living room floor and had me strip. They talked amongst themselves, at least :)

[15:09] TheFool Aren't Megan's parties pretty to-the-point like that, sometimes?

[15:10] CollaredMom True, but it's a bit more intense, which I prefer ;) Sometimes they strip off my clothes for me rather aggressively

[15:10] TheFool They don't rip your clothes off, do they? Like physically tearing them?

[15:11] CollaredMom Haha, no, but they do manhandle me a little during the process. Not that I mind, of course~

[15:11] TheFool Oh, that sounds like fun!

[15:12] CollaredMom I'd let my sons rip my clothes off, but, well, I usually don't wear any at home, haha. Disadvantage of my enforced nudism.

[15:12] TheFool But you're allowed to wear some if they tell you to, right? How often does that actually happen?

[15:13] CollaredMom Hrm. Couple times a month? It's not terribly often, haha. Although, I think Jason's been more willing to take advantage of it lately.

[15:13] TheFool I suppose if I was them, I'd mostly wanna keep you naked, too.

[15:14] CollaredMom It certainly makes our free use arrangement easier, haha!

[15:14] TheFool I have to admit, though, I'm curious what you actually *do* wear when you have clothes.

[15:15] CollaredMom Well, I dress surprisingly modestly when I go outside. I tend to favor longer dresses or jeans. I'll wear sundresses in the summer, though, haha.

[15:15] TheFool That makes sense based on what I know about you but also feels kinda wrong. I guess not everyone knows what a freak you are, though.

[15:16] CollaredMom Quite ;) And I much prefer it that way!

[15:16] TheFool And what about when you're home?

[15:17] CollaredMom Precisely what you'd expect, haha. I have some lingerie, stockings, a few pairs of heels. One corset I got from Megan. Master's bought a few costumes but sadly they don't get much use.

[15:17] TheFool Kind of a pity. What sort of costumes?

[15:18] CollaredMom There's a sexy nurse one I've worn a few times. I don't remember the others, haha.

[15:18] TheFool I guess when I was their age, I mostly just wanted to see naked girls or bikinis and heels. I think you get an appreciation for sexier clothing as you get older.

[15:19] CollaredMom Entirely possible, haha. I do like my nudity best, though. It fits our dynamic the best :)

[15:19] TheFool It does look nice, from the pictures you've sent me.

[15:20] CollaredMom Should I send you more? ;)

[15:20] TheFool Fun as that would be, I'm at work and want to avoid awkward questions. Got something I need to go do in ~15 minutes, just a heads up.

[15:21] CollaredMom Oh dear, sorry to hear that :(

[15:21] CollaredMom I suppose I shouldn't get you worked up or distract you, then? ;)

[15:22] TheFool You shouldn't, but will that stop you?

[15:22] CollaredMom Oh, Terry, how hurtful! I'm a very good girl, I'll have you know. ;) Master and my boys say so! I can ask them if you don't believe me!

[15:23] TheFool What are they up to, anyway? And where's Emily?

[15:23] CollaredMom Master and Jason are out, I believe. The other kids are in the living room playing games.

[15:24] TheFool Give them my love!

[15:24] CollaredMom One moment, I'll pass that along :)

[15:26] CollaredMom They say hello back :) And that they hope your work thing isn't too boring

[15:26] TheFool Thanks! It probably will be, but oh well.

[15:26] TheFool Are they behaving themselves? Giving you any trouble?

[15:27] CollaredMom Oh, Emily and Jake asked me to pass along that they're fucking. :)

[15:27] TheFool Hot damn. Did you walk in on that?

[15:28] CollaredMom Actually, no! I brought you up and then knowing glances were exchanged, haha.

[15:28] TheFool Your kids are devious. I approve.

[15:28] TheFool How are they positioned?

[15:29] CollaredMom Doggystyle, the house favorite! Jake's going at it quite enthusiastically.

[15:29] TheFool And you're being left out?

[15:30] CollaredMom I've been reassured I'm in for it as soon as you leave ;)

[15:30] TheFool Damn. I almost wanna leave earlier just for that.

[15:30] CollaredMom Well, don't feel rushed :)

[15:31] TheFool I actually *should* be responsible and log off soon. Don't wanna be late. Plus… I like the idea of controlling when you get fucked.

[15:31] CollaredMom Do have fun :)

[15:31] TheFool I will! I'll be entertained by thoughts of you and your daughter getting fucked together. Take care!

Session Close

Notes:

Hey gang! First new fic in a while. I hope this one wasn't too rambly. Hope you all had a happy Halloween!

Chapter 46: Tommy Tells All

Summary:

Terry catches up with Tommy and Jake, and learns how Tommy and his brother are adjusting to life with their Aunt Megan

Chapter Text

Session Start

* Now talking in #bestestchannelever

TheFool has joined #bestestchannelever

[16:02] TheFool Well, that's certainly an eye-catching title.

[16:02] JakeTheSnek well its obviously true cause its full of cool people!

[16:02] Tomcat theres just us, tho

[16:03] JakeTheSnek we're all cool!

[16:03] Tomcat even me?

[16:03] TheFool I don't believe we've talked directly before, Tommy. Nice to meet you!

[16:04] Tomcat nice to meet you too!

[16:04] TheFool How are things at Megan's? You and your brother getting settled in?

[16:05] Tomcat yeah it was a little weird at first but now its a lot of fun and everybody is super nice to us!

[16:05] JakeTheSnek yeah! You and Brady are awesome!

[16:05] TheFool That's really good to hear!

[16:06] Tomcat i thought u guys would think we were lame D:

[16:06] JakeTheSnek what? Why?

[16:07] Tomcat cause u guys are cooler and kinkier

[16:07] JakeTheSnek youre plenty kinky!

[16:08] TheFool Do Megan and Tanya give you special treatment?

[16:08] Tomcat sorta! Since me and my bro live with her we get to, um, do stuff with them more often

[16:08] Tomcat not like Naomi tho cause we usually ask

[16:08] JakeTheSnek more like demand ;p

[16:09] TheFool Oh? You get to order your aunts around?

[16:09] Tomcat …well a little but only cause Aunt Tanya said she likes it

[16:09] Tomcat like instead of "can i have a blowjob?" she likes when we just say "i want a bj"

[16:10] JakeTheSnek its not like Megan says no to you lmao

[16:10] TheFool What about Juli? See her often?

[16:10] Tomcat sometimes shes busy but when shes home we do stuff with her too! Shes super cool

[16:11] Tomcat actually we both used to feel kinda bad about bothering our aunts for stuff and theyd tell us not to worry about it

[16:11] Tomcat but i got really into it with Aunt Tanya and then… we just kinda kept doing it a lot lmao

[16:11] TheFool Oh? Into what, exactly?

[16:12] JakeTheSnek its teh dirty talk isnt it ;P

[16:12] Tomcat well… yeah… but she also told me the other stuff she and Aunt Megan are really into…

[16:12] TheFool What kinda stuff do you say to her? I'm curious now.

[16:13] Tomcat ... like she'll say "do you like fucking your aunties big black ass" and i'll… y'know… say that yeah i do like fucking her fat ass

[16:13] Tomcat omg im so embarassed

[16:13] TheFool That's understandable. Stuff that's fun can feel embarrassing afterwards.

[16:14] Tomcat when she told me to try that i liked it a lot and we started doing it… a lot

[16:14] Tomcat she let me fuck her a lot every day. It made me feel really good!

[16:15] TheFool Was Megan jealous?

[16:15] Tomcat a little bit but then Brady started doing it with her

[16:16] TheFool Nice! So are you two still sticking to your preferred aunt for now?

[16:16] Tomcat no we do it with them equally now!

[16:16] TheFool When did you last fuck one of them?

[16:17] Tomcat …right before i got on here hehe

[16:17] TheFool Oh, nice. Megan and Tanya busy?

[16:18] Tomcat yeah, there's a lot of other boys over right now

[16:18] TheFool Full holes?

[16:18] Tomcat yeah!

[16:19] TheFool Nice.

[16:19] JakeTheSnek Mom says hi to both of you!

[16:19] TheFool Hi, Naomi!

[16:19] JakeTheSnek hi mrs h!

[16:20] TheFool Hope you're keeping her well-fucked.

[16:20] JakeTheSnek we are! Cause i'm about to fuck her again

[16:20] Tomcat lucky!

[16:21] TheFool Says the guy who lives with Megan and Tanya.

[16:21] Tomcat yeah but theyre busy!

[16:22] TheFool So what other stuff do you do with them?

[16:22] Tomcat oh, we get a lot of footjobs from them. They're so good at it! And it looks really pretty with their nail polish!

[16:23] Tomcat oh and they both love being fucked in both holes which is good cause there's two of us so we can just do that whenever they want

[16:23] TheFool I envy you.

[16:23] Tomcat oh sorry

[16:24] TheFool No, it's good! Enjoy them while you can!

[16:24] TheFool I need to get back to work. Nice chatting with ya!

[16:25] Tomcat you too!

Session Close

Chapter 47: The Year Without a Collared Mom

Summary:

Naomi's feeling down because people have forgotten the true meaning of incest, and her kids set forth on a quest to bring back the spirit of the holiday!

Chapter Text

"Doctor, what is it?" Frank asked as the doctor finished examining Naomi. He was doing a housecall like in old-timey movies because I'm ripping off The Year Without A Santa Claus and that also started with a doctor showing up at Santa's house.

"Well, I'm afraid your wife's suffering from a lack of holiday cheer." The doctor said. "Not enough people believe in the spirit of incest anymore. You're going to have to cancel incest this year, I'm afraid."

"No…" Naomi said. "You don't mean-"
"That's right. This'll have to be a year without a collared mom!" The doctor declared. "Now get plenty of rest and you'll feel better in no time."

"Oh, alright…"

As the doctor left, Naomi's kids came in to see her.

"I'm sorry, kids." Naomi said. "It seems that nobody wants incest anymore, so we'll have to cancel it this year."

"I suppose we'll have to do normal family stuff now." Frank said. "What do normal families do? Board games?"

"More like bored games!" Jake, her youngest, chimed in.

"Yeah, video games are where it's at." Jason, her oldest, said.

"Think of all those poor moms that will go unfucked this year…" Jeremy, her middle son, lamented.

"Well, I guess we gotta get used to it now." Emily, Jeremy's twin sister, added.

"You kids run along and let your mother rest, alright?" Frank said. "I'll have to call the newspapers, we'll need to put out a press release saying incest is canceled this year."

The kids made their way to the living room and sat on the couch. They pulled out their phones as they thought about what to do.

"People… don't care about incest?" Emily asked. "I wonder what's gotten into them."

"Maybe they've just forgotten the true meaning of incest." Jake suggested.

"Hrm. How can we help?" Jeremy pondered.

"What if we go and remind people why it's so great!" Jason suggested. "We can go out and save incest!'

"And our mom!"

"But none of us are old enough to drive, and Southern California's public transport is in shambles." Jeremy pointed out. "And Dad's probably not gonna drive us around, since he's busy with stuff."

"Wait, I have it!" Jake shouted as he rushed outside. His siblings stood up and looked outside the window. They watched as Jake pulled up a sleigh out front.

"Where did you even get that?" Jason asked.

"Internet." Jake said. "Amazon had a great deal on them. Anyway! We can use this!"

"Don't we need an animal to actually pull the sleigh?" Jeremy pointed out. "It's not gonna go anywhere by itself."

"We can have Em do it!" Jake said.

"W-what?"

"Oh and you gotta do it naked." Jake added.

"But it's cold!"

"How are we gonna spread holiday cheer if you're wearing clothing?!" Jason asked.

" Fine! " Emily let out a sigh and stripped off her clothes. She took a moment to put on her collar, and then her brothers hooked her up to the sleigh.

"What are you kids doing out here?" Frank asked as he stepped outside.

"We're gonna go teach people the true meaning of incest!" Jason said.

"Alright, best of luck, kids!" Frank said. He waved them off as Emily started running, and the sleigh took off from the ground. As they disappeared into the sky, he went back inside to tend to his wife.

"What was all that commotion?" Naomi asked.

"Oh, the kids decided to go around the world and see if people have really forgotten the true meaning of incest." Frank said.

"They left on their own?!" Naomi asked, bolting upright in bed.

"I think they'll be fine! There's 4 of them, and they have cell phones."

"Francis, there's a monster on the loose!" Naomi said as she got out of bed. "We have to go after them and make sure they're safe!"

"What monster?"

"You don't remember?! It was… the Abominable Tsuchisnowko! "

"So, like, where are we going?" Jake asked.

"Good question." Jason said. "Jer, where are we going?"

"I don't know." Jeremy answered.

"I thought you were navigating!"

"What? Oh, no, I was just whipping Emily for the fun of it." Jeremy said.

"You should do some more of that!" Emily called out as she pulled the flying sleigh.

"Can I do it?" Jason asked.

"No, you're gonna do it too hard. Jeremy does- Ah! " She let out a sudden yelp as Jeremy's whip lashed against her skin. "Mmm! Yeah, like that!"

As the kids had their fun, they approached a conspicuous mountain poking into the clouds. Little did they realize they were upon the lair of a fearsome beast- the Abominable Tsuchisnowko!

On the peak of the mountain sat a short, chubby little snake. It was maybe a foot long, and its scales were a pale, icy blue. Its eyes tracked the approaching sleigh. It opened its mighty jaws and let loose a powerful hiss. Unfortunately, being a small snake quite a ways away, nobody heard it. Realizing this, the Tsuchisnowko instead started up a nearby gramophone it kept for just such occasions.

"Do you guys hear that?" Jason asked.

"Yeah, it sounds like a recording of Godzilla's roar on a vinyl record."

"What is that?"

Suddenly, a snowball came flying at their sleigh, narrowly missing the side.

"Where'd that come from?" Jake asked.

"I think something's throwing them from the mountain." Emily said. "Wait, there's another one!"

But it was too late. The snowball hit her in the tits. It didn't really hurt, it was just kind of annoying.

"Alright, I'm gonna land!" Emily shouted. "This sucks!"

The four of them landed their sleigh in the middle of a nondescript town somewhere in America. There was a chill in the air and snow on the ground, and nearby they spotted a group of kids playing in the snow. They were sitting in a circle, talking amongst themselves. A few of them turned their heads to look at Naomi's kids.

"How come you're not wearing any clothes?" One kid asked Emily.

"Uh, cause it's kinky?" Emily answered.

"Yeah! We're celebrating Incest!" Jake chimed in.

"Pfft, incest! Didn't you hear that incest is canceled? They said the Collared Mom put out a statement in the paper."

"I don't even believe in Collared Mom, anyway." Another kid added.

"You… don't believe in someone… who made a statement to the newspaper?" Jeremy asked.

"Ha! Look at this nerd acting like plot holes are a serious critique!" One of the other kids said.

"You guys aren't into incest?" Jason asked.

"No way, incest is super lame!" One kid said. "We're really into Pathfinder!"

"I'm a bard!" Another kid said. The kids then went back to playing their alleged game.

"Wow…" Jason said with a sigh. "I guess people really have forgotten what the season is all about."

"Um… excuse me…" A timid boy, a little younger than Jake, approached the group. "I… I think incest is cool, too! And I believe in Collared Mom! But all my friends would rather play things like Lancer instead."

"Well, you don't have to tell your friends!" Jake said. "You just have to believe!"

"I wanna tell my mom, though!" The boy said. His name's Kevin, I've decided. "I don't know what to say to her, though…"

"Don't you worry, Kevin! We'll help!"

The group made their way to Kevin's house, where Kevin's mom was watching TV in the living room. She looked over curiously at the other kids.

"Who are your new friends, Kevin?" She asked.

"I'm Jason."

"I'm Jeremy."

"I'm Emily."
"I'm Jake."

"They came from-"

"Hang on, you're Naomi's kids!" She suddenly lit up seeing them. "Oh, I love following your exploits! What are you doing out here?! I heard incest was cancelled!"

"We're trying to prove that people still remember the true meaning of incest!"

"Oh, that's so sweet!" She let out a wistful sigh. "You know, I'd love to celebrate, but I don't think Kevin would go for that. He and all his friends are really into Dungeons and Dragons, if you hadn't noticed."

"A-actually, Mom…" Kevin said sheepishly, "I'd… I'd love to do that stuff with you!"

"R-really?!"

"Y-yeah! I wanna get sucked off and then cum on those big tits of yours! I wanna bang you on the couch while we watch TV together!"

"W-well, I want to do that, too!" She said. "Well, I would … but it's been really cold lately. I don't really want to take off my clothes."

"Aw, dang, my weiner is basically frozen, too." Kevin said.

"Damn." Jason muttered. "If only we could do something about the cold…"

"There you kids are!" The kids turned to look as their parents came rushing in the house. "We've been looking all over for you!"

"Mom, what are you doing out of bed?" Jake asked.

"I couldn't let my kids get eaten by the monster roaming around!"

"What monster?"

"The Abominable Tsuchisnowko, of course!" Naomi answered. The kids looked at each other with confusion.

"Y'think that's the thing that threw snowballs at me earlier?" Emily asked.

"Maybe it's causing all the cold." Jeremy mused.

"Then we'll have to confront it if we want to save incest!" Jake said. "C'mon, everyone!"

The family made their way up the large mountain to the lair of the Abominable Tsuchisnowko. It was an icy cave, with large icicles dangling from the ceiling. There, they found the Tsuchisnowko eating a snow cone.

"Woah, visitors!" The Tsuchisnowko said. "Okay, hang on, I have something for this!"

The Tsuchisnowko put on a straw hat and started doing a musical number introducing itself. He wiggled and shimmied his little body to the beat, despite not having any legs. Nobody had the heart to tell him that musical numbers don't really work in a text-based medium, and they all applauded him when he was done.

"Anyway," The Tsuchisnowko said as he tossed his hat aside, "what brings you all the way up here?"

"Please, Mr. Tsuchisnowko, it's far too cold, and people aren't willing to take their clothes off to celebrate incest!" Naomi pleaded.

"But… you're naked." The Tsuchisnowko pointed out. "There's two of you without clothes."

"Not everyone's as dedicated to the whole submission thing as us." Emily explained.

"But if it's cold, then I can sell my Abominable TsuchiSnowCones!" The Tsuchisnowko showed off a box with its face on it. "They come in 6 flavors!"

"Wouldn't most supermarkets be able to store them in a freezer, anyway?" Naomi asked.

"Oh. Yeah. I guess they would." The Tsuchisnowko conceded. "Okay, fine, I'll ease up on the snow."

"Thank you so much, Mr. Tsuchisnowko!" Naomi reached down and gave the little snake a hug.

The family got back in their sleighs and flew down to the nearby town. As they soared through the air, they saw a beautiful sight below. Everyone was fucking a blood relative. Sons pounded their moms, daughters blew their dads, and cousins sixty-nine'd. It filled their hearts with joy.

"This is way better than those dumb tabletop games!" One of the kids on the ground shouted.

"Yeah, Dungeons and Dragons is shit, actually! This is way better!"

"We were going to do this joke before the layoff announcement, so it's not tasteless!"

Their mission accomplished, Naomi and her family flew back home.

"Merry Incest to all," Naomi shouted, "and to all, a good night!"

Chapter 48: Sai's Stress Relief

Summary:

When something at work keeps Sai late, Jason and Rag are called upon to take her mind off it once she gets home

Notes:

(See the end of the chapter for notes.)

Chapter Text

"You're locked up this week?" Jason asked. "I thought you did that last week."

"Mom wanted to do it full-time, remember?" Rag asked. "I'm starting to think you're just pretending to forget on purpose."

"What?! You really think I'd do that?"

"Yes. That's very you."

"Damn." Jason looked down at his phone. "Picked that trick up from Jamie."

"I mean, I assume you came over just to hook up with her."

"That is not true! I came here to spend time with my best friend. You're like a brother to me, Rag. A brother I'd commit incest with."

"...You don't already do that with your actual brothers?"

"No? That would be weird."

"You guys fuck your mom together, that seems like… committing incest with them. In a broad sense."

"I… don't know if that counts, actually." Jason asked his brothers via text their opinion on this debate. "So, like, where is Sai? It's a little late."

"Uh, work probably." Rag checked his own phone. "Sometimes things run late. She didn't text me anything so she's probably fine. Might be stuck in traffic."

A few minutes later, they saw headlights as a car pulled into the driveway. An annoyed looking Sai emerged from the car, holding some bags of fast food. Jason decided to get the door for her.

"Hey, Sai."

"Hi, Mom."

"I work with such fucking idiots ." Sai groaned through gritted teeth as she stepped inside.

"Do you, uh, wanna talk about it?" Jason offered.

"No." Sai put the food down on the coffee table. "What I want is to get fucked so hard I pass out."

"I, um, okay! Can do!" Jason said as he started to take off his clothes.

"You too." She said, pointing at Rag.

"Oh, me? I thought I was in chastity until the weekend."
"Your cock belongs to me," Sai explained as she reached down to take off the anklet with Rag's key, "so I can unlock it whenever I see fit."

"O-oh, yeah, I guess that makes sense…" Rag took off his pants, revealing his caged dick. Sai fiddled with the lock, then hastily removed the cage once it was unlocked. Rag helped his mother take off her top, and Jason removed her high heels and pants.

"Now let's see if he remembers how to use it." Sai shot her son a smug look.

"Sounds like someone needs to be put back in her place." Jason said as he forced her onto the couch, onto her stomach.

"Yeah? You think you're gonna be the one to do it?" Sai looked back at him. "I'd like to see you-" She stopped as he put her in a chokehold.

"Rag, get over here." Jason ordered. "We can break her together!~"

Rag went over to the couch and sat down. Jason repositioned Sai so that she was on top of Rag. The two of them slid inside her waiting holes, with her son claiming her pussy and Jason claiming her ass.

"Doin' it for ya, slut?" Jason asked as he pounded into her asshole.

"Not bad… for children." Sai managed to get out. "Not that you'd measure up to real men."

"Don't act like you don't love it." Jason tightened his grip around her throat and fucked her harder. "I've seen you fuck hordes of boys, and most of them are younger than us!"

"Kinda cute when you pretend not to be a slut, Mom."

"Oh yeah?" Sai fixed her gaze on Rag. "Your mom's pussy feel slutty? Can you feel all the cocks I've fucked? All the cum I've taken? Like this little taste of what you usually miss out on?"

Before Rag could answer, Sai started to scream. Rag reached up and covered her mouth to muffle the sound. Her body writhed violently between the two of them, causing Jason to tighten his hold even further. She squirted enough to leave a wet patch on the couch.

"Cum already?" Jason asked. "God, you're easy. And we're just getting started…"

"Thanks for dinner." Jason said as he bit into a burger. "Do you, uh, wanna put something on?"

"Not really, no." Sai answered. She was still in the nude, with cum leaking from both her holes as she ate. "It's my house, why bother?"

"Fair enough, I suppose."

"Your mother doesn't usually dress for dinner, does she?"

"Oh yeah, good point."

"So, uh, do I need to put the cage back on?" Rag asked.

"Hrm. Later. After I've had… dessert."

Notes:

Happy 2024, everyone! People kept saying that wanted more Sai stuff!

Chapter 49: Unraveling Riddles of the Ages

Summary:

Jason sets out to investigate why anime girls keep getting stuck in washing machines

Chapter Text

As Naomi walked by the laundry room, she heard noise coming from within. The machines weren't running, but someone was definitely in there doing something. Curious, she peeked inside. She found Jason, her oldest son, examining the washing machine. The door was open, and he was peering around inside.
"Is something wrong with the washing machine?" Naomi asked.
"No, I just wanted to check something." Sensing his mother would like an explanation, he continued. "You know that cliche of anime girls getting stuck in washing machines?"
"Not particularly, but I'll take your word for it."
"Well, I wanted to know how they keep getting stuck." Jason stuck his head inside. "It seems pretty spacious…"
"One needn't stick their entire upper body in there to empty it, either." Naomi stepped closer. "Although, I suppose Japanese washing machines might have smaller doors."
"Oh, that might be it…"
"So, what happens after they get stuck?"
"They ask their stepbrothers for help and then get fucked."
"Ah, I see. Quite a lot of step-relatives in porn, I've noticed."
"It's like diet incest if you can't handle the real thing."
"Do they ever elaborate on the mechanism by which is a girl is un-stuck from the washing machine? Do they just pull on her?"
"I don't know, I assume they don't really get into the specifics."
"How disappointing." Naomi looked at Jason, then looked at the washing machine. "I suppose you'd like to give it a shot, then?"
"Only if you call me 'stepbro'."
"You know," Naomi said as she stuck her head in the washing machine, "there's something to be said for asking your mother to pretend to be your stepsister."
"Is it Freudian?" Jason asked.
"I've no idea." Naomi took a deep breath and then tried her best at acting. "O-oh, stepbrother, I require assistance! I've gotten stuck in the washing machine… somehow…"
"I'll unstick you, mo- stepsister! With my penis!"
"Oh, that's… logical…"
Jason quickly got his cock out and stuck it in his mom's exposed pussy. He grabbed her hips and started going to town. Naomi felt the drum move as he thrust into her. Part of her worried she might break it.
"Are you, ah, enjoying yourself?" Naomi asked. Her moans echoed a bit inside the washing machine.
"It's… alright…" Jason said. "And you?"
"It's not… wildly pleasant in here…"
"Yeah, okay, well," Jason said as he pulled out of Naomi, "at least we tried it. Stuck-in-washer sex, actually kinda mediocre." He closed the machine's door after Naomi removed herself from it.
"An important discovery for science." Naomi said with a smile. She looked down at her son's still-hard erection. "Shall I take care of that for you, since we're here?"
In lieu of an answer, Jason pushed Naomi against the washing machine and started sucking on one of her tits. He lifted up one of her legs and quickly slid back into her, fucking her with wild abandon. Naomi wrapped her arms around him, pulling him into her chest.
"Thank you, ah, for freeing me, stepbrother…" Naomi struggled to keep a straight face. Jason looked up at her, and expressed his disapproval by biting her. Naomi let out a sudden gasp. "Fuck, that hurts so good…" Naomi muttered.
Jason fucked her for a while yet. Once he'd had his fill, he hilted into her and unloaded his balls. When he pulled out, cum started to drip down Naomi's thighs.
"Satisfied, dear?" Naomi asked.
"For now."
"Happy to be of service~" With that, Naomi left to go clean herself and carry on with her day.

Chapter 50: Differences of Opinion

Summary:

Megan and Naomi discuss the different ways they approach their similar lifestyles

Notes:

(See the end of the chapter for notes.)

Chapter Text

Session Start

* Now talking in #PerfectlyNormal

TheFool has joined #PerfectlyNormal

[16:00] TheFool What an inconspicuous channel name you've chosen.

[16:00] CollaredMom Megan's creativity strikes again :)

[16:00] OrgyMom Nobody else will think it's weird or wanna try to join!

[16:01] TheFool Indeed. We can chat about stocks!

[16:01] CollaredMom I'm afraid stocks are outside my area of expertise, haha

[16:01] OrgyMom Gamestop announced their earnings call and MOASS hasnt happened :x

[16:02] TheFool …What is "MOASS"?

[16:02] OrgyMom a bunch of weirdos think that if they buy gamestop stock, it will destroy the economy and make them all rich

[16:02] TheFool Oh. Not going well, then?

[16:03] OrgyMom not yet, but any day now!

[16:03] TheFool So, you two staying well-fucked?

[16:03] OrgyMom fuck yeah!

[16:03] CollaredMom Of course!

[16:04] TheFool Do you two ever make a competition out of who can handle more cock?

[16:04] CollaredMom No, haha. I'd get crushed soundly :)

[16:04] OrgyMom idk, you could beat me if you really wanted :p

[16:05] TheFool You think so?

[16:05] OrgyMom Naomi's just inefficient

[16:05] CollaredMom Haha, well that's not quite how I'd put it…

[16:05] TheFool Oh? How so?

[16:06] OrgyMom i prefer getting all my holes stuffed, but naomi usually just goes one at a time

[16:06] CollaredMom That's not entirely true, haha. I operate at capacity whenever I'm at your place ;)

[16:07] TheFool Come to think of it, you do seem to go one at a time in a lot of the videos I've seen of you…

[16:07] CollaredMom I admit there's something about it I enjoy ;)

[16:08] TheFool Because it's easier?

[16:08] CollaredMom Hrm. There's that, but it feels very… ritualized? I'm not sure how else to explain it, haha.

[16:09] TheFool Oh! Okay, I think I see what you mean. I see the appeal now.

[16:09] CollaredMom It helps emphasize the feeling that I'm being used, haha.

[16:09] TheFool So, the kids back from school yet?

[16:10] CollaredMom Indeed they are, haha. Got back a while ago!

[16:10] OrgyMom yeah, the first big rush is over

[16:10] TheFool What are your sons and nephews up to?

[16:11] CollaredMom Homework, haha. But they've come to say hello :)

[16:11] OrgyMom mine also say hi! They're waiting for their turn to fuck me now ;p

[16:12] TheFool Who's fucking you now?

[16:12] OrgyMom dunno his name, lmao

[16:12] CollaredMom how like you, haha

[16:13] TheFool How come Naomi never has this problem?

[16:13] CollaredMom i suppose i do, but usually i dont message you at the time, haha

[16:13] OrgyMom dont judge me, its hot ;D

[16:13] TheFool I thought you knew the boys in your group pretty well?

[16:14] OrgyMom sorta, but im bad with names, lmao. I know faces better.

[16:14] TheFool Oh, that's what you meant. I have to imagine hookups with strangers are difficult in your lifestyle.

[16:15] CollaredMom …but not impossible ;)

[16:15] OrgyMom Getting creamed ^.~

[16:15] TheFool Nice!

[16:15] CollaredMom Congrats!

[16:15] OrgyMom But yeah, it *can* happen if you're lucky!~

[16:16] TheFool Like… boys you don't know? Or old farts like me?

[16:16] OrgyMom i meant boys ;p

[16:16] TheFool How does that work?

[16:17] OrgyMom well, when you have enough… notoriety, sometimes rumors spread and guys wanna join the action. altho those guys usually wanna become regulars when theres milfs offering free pussy

[16:17] CollaredMom i also get recognized on occasion by local 'fans', haha. I've had a similar effect by having the boys bring over friends i didnt know

[16:17] OrgyMom i mean i encourage that sorta thing around here

[16:18] CollaredMom ah, i meant more that i didnt know they knew about our lifestyle. Or id been told they *didnt* know…

[16:18] OrgyMom OMFG THATS HILARIOUS

[16:18] TheFool Oh, that sounds stressful.

[16:18] CollaredMom it was rather scary the first time, haha

[16:19] TheFool I imagine it was! What happened?

[16:20] CollaredMom jason had a friend over id never met, so i had on clothes and was playing everything safe. Then this friend rather suddenly asked me for a blowjob and got his dick out, haha

[16:20] OrgyMom damn, thats kinda hot

[16:20] TheFool …So, did you give him one?

[16:21] CollaredMom of course :) then he wanted to fuck me several times before he actually left, haha

[16:21] OrgyMom who wouldn't wanna?!

[16:21] TheFool Amen to that.

[16:22] CollaredMom You flatter me. :) Also, just got filled!

[16:22] TheFool Megan, do Tommy and Brian ever bring over friends?

[16:22] OrgyMom recently they have, although i wouldnt let them bring over brand new ppl uninvited ;p

[16:23] OrgyMom but once i know them, i dont mind 'em droppin over uninvited ;3

[16:23] TheFool I imagine that happens alot. I know if I'd known someone like you at their age, I'd have come over every chance I could!

[16:24] OrgyMom things are picking up here, so im gonna have to take a break for a bit to put my holes to use, unless you two wanna log off?

[16:24] TheFool …I should *really* get back to work.

[16:24] CollaredMom take care then, you two :)

[16:25] TheFool Nice seeing you both!

[16:25] OrgyMom bye!

Session Close

Notes:

Hey gang! Wow, number 50! Crazy we've made it this far.

I don't want to make any promises, but I've been feeling a bit more in the mood to write Naomi and her antics again, so you might be seeing more Collared Mom in the near future.

Actually, maybe I should explain where I've "been". I haven't posted much fanfic of late due to working on other personal projects (i may or may not be trying to write a book). I just got a little burnt out writing porn and decided to switch to something that came to me more naturally. The ideas for fics (both Collared Mom and other general fanfics) ran kinda dry for a while, and I really had this urge to write this other thing I just couldn't shake. I'm in a bit of a porn mood again, though, so if nothing else you'll probably get new entries here and in Ring of Lust.

Chapter 51: Mother's Mercy

Summary:

Terry has a little chat with Rag and Sai, but the two have unexpected company over

Notes:

(See the end of the chapter for notes.)

Chapter Text

Session Start

* Now talking in #Room137

TheFool has joined #Room137

[17:00] TheFool What happened to Rooms 1-136?

[17:00] Saiclone no one's really sure.

[17:00] Ragged I think it's a science joke…

[17:01] TheFool Oh, science was never my strong suit.

[17:01] Ragged I'm pretty good at it!

[17:01] TheFool So, what are you two up to? I just got home.

[17:02] Saiclone good question. rag, what are we up to?

[17:02] Ragged I'm watching you get fucked, Ma'am.

[17:02] TheFool You certainly don't waste time…

[17:02] Saiclone you can provide more detail than that.

[17:03] Ragged I'm watching you get railed from behind by Jason in some lacy lingerie.

[17:03] TheFool Damn. Sounds like a good time.

[17:04] Saiclone do i sound like i'm having a good time, rag?

[17:04] Ragged You're moaning pretty loudly, Ma'am.

[17:04] Ragged Jake and Jeremy say hi, Terry.

[17:05] TheFool I'm flattered by all the effort you went to for me!

[17:05] Saiclone i know what you like.

[17:05] TheFool Rag, are you going to get a turn? I forget if it's one of your locked weeks.

[17:06] Ragged No, I'm locked full-time during the week.

[17:06] TheFool Oh, right, I think I remember hearing about that. So, still locked up for a few more days?

[17:06] Ragged Yeah, I get unlocked on weekends.

[17:07] Saiclone i tried having him fulltime for a bit, but i felt bad he couldnt play with his friends

[17:07] TheFool Aw, how generous of you!

[17:07] Saiclone i am a paragon of benevolence

[17:08] Ragged You sure are, Ma'am.

[17:08] TheFool Do kids still call their parents "sir/ma'am"?

[17:08] Saiclone this is purely a sex thing for us

[17:09] TheFool Oh, so he doesn't do that on accident in public?

[17:09] Ragged No, lmao. I'm careful!

[17:09] Saiclone rag, get ready.

[17:09] TheFool For what?

[17:10] Ragged Jason's about to cum.

[17:10] TheFool Oh!

[17:11] Ragged He was fucking her *really* hard, then came inside her. They both made a lot of noise. He just pulled out, and I can see the creampie starting to leak out. I'm gonna have to go clean it up.

[17:11] TheFool Oh, that's hot!

[17:11] Saiclone He's pretty enthusiastic about cleanup these days. All the practice has made him good with his mouth.

[17:12] TheFool Oh, I bet.

[17:13] Ragged Back. Jake's fucking her now.

[17:13] TheFool How's he doing?

[17:13] Saiclone fantastic.

[17:13] TheFool Rag, does it feel weird swallowing other guys' cum? I don't think I could do that.

[17:14] Ragged It used to, it doesn't anymore.

[17:14] TheFool Do you like doing it?

[17:14] Ragged …Honestly, yeah. It's humiliating, but also really hot.

[17:15] TheFool Does it taste funny?

[17:15] Ragged Just kinda salty.

[17:16] TheFool You know, I'm suddenly feeling kinda tired.

[17:16] Saiclone you just came, didn't you?

[17:16] TheFool …No comment.

[17:17] Saiclone you were jerking off thinking of me getting fucked, there's no shame in that.

[17:17] TheFool And Rag helping out!

[17:18] TheFool I wasn't into the cuck thing at all until I met all of you. You guys have corrupted me.

[17:18] Saiclone you're welcome.

[17:19] TheFool I actually should rustle up some vittles. It was great seeing you!

[17:19] Saiclone take care.

[17:19] Ragged Bye, Terry!

Session Close