"Um… Dora?" Diego said as he walked up to her as she folded laundry. He hugged her from behind. She knew it was because he didn't want her to see his face.
"Yeah baby, what'd you need?" She said and kept folding. He let his hands clasp in front of her stomach and let his chin rest on her shoulder.
"Can…. Can we do… it… Thursday. You have the day off…" Diego said quietly, like a secret. He squeezed her a little bit and she put down the shirt she folded and squeezed his hands and patted them.
"Sure sweetie! Do you want me to help you with prep or do you want to do that by yourself?" She asked. She wanted to make sure he knew that it was a good thing to ask and that it was okay to want this.
"…by myself…" He mumbled and let go of her. He turned to leave but she caught him by the elbow and spun him around to face her.
"Okay well that's the day after tomorrow so I'll get everything tomorrow. Thank you for telling me." Eudora said and kissed his forehead. Diego smiled and nodded. There was a low spark in his gut, he was so excited and nervous.
Eudora did as she told him and bought the remaining supplies needed for this adventure the next day.
"Mommyyyy it feels weir-weird! I don't think I can-can do this… will you help m-m-me please? I kn-kn-ow know it's icky and all so if you don't want to you don't have t-to…" Diego mumbled from the bathroom.
He was attempting to use the small enema Eudora had bought but it felt so strange. The water was cold and he didn't know how far he needed to put it in and he needed to hold it at a weird angle and he was just having trouble.
Eudora smiled and walked to the unlocked bathroom. She had been double checking everything, everything was cleaned and sanitized and everything was where it should be.
Diego was sitting on the toilet holding the enema below his ass and looked so pitiful sitting in just his thick cotton socks and his black sweater. He pouted and looked so frustrated and embarrassed. Eudora thought it was the cutest thing she'd seen in a while. She went over to him and pulled his arm up and kissed his forehead.
"It's okay baby. I'm sure it can be hard all by yourself. I don't mind at all. How about you stand up and grab the back of the toilet. Good boy. Good job." Eudora said and took the small bottle from Diego as he stood and turned around. Diego's arms shook a bit.
Eudora ran her hand down his hip a few times when she saw how tense he was. Diego breathed deeply a few times and slowly relaxed.
"Good boy. Relax Diego. Big breath in, and out." Eudora said and when Diego let the air out she slowly pressed the thin white end all the inside until the tip was fully inside. Diego whined and wiggled his hips back and forth a little bit but Eudora grabbed his hip.
"Still. I'm gonna fill you and when I pull this out you keep it inside. Do not let it out until I tell you. Understand?" Eudora says and got a grip on the small bottle. Diego hummed but Eudora pinched his hip which caused him to yelp but nod and answer.
"I understand mommy." Diego says and groans as the chilly liquid floods his insides. It felt strange and loose and he really doesn't like it. He whimpered and sniffled and groaned.
"I don't like this! It's cold and it feels… gross." Diego whined and Eudora shushed him and slowly pulled the tip out.
"Hold. It. In. I know it doesn't feel too good but keep it in. I'm going to go finish what I was doing and you don't let a single drop out. Be good." Eudora said and watched Diego clench right after the tip finally slipped out. He whined but nodded.
"Okay, I'll do my best." Diego said and smiled fakely. Eudora kissed his face and ruffled his hair. His skin was hot and she felt the tension radiating off of him.
"Perfect. Perfect boy. Just hold on for a few minutes." Eudora said and kissed him again and left the bathroom. She didn't shut the door because Diego needed to know he was being watched, he was being looked after even alone.
Eudora finished putting the bedding folded to the side. There was only a sheet and a few pillows left on the bed, they had read that if the one receiving could be propped up on pillows it would help. She walked back into the bathroom and Diego looked at her hopefully but she shook her head.
She thought he might just break out in tears, his face was red with effort and his back end was tense. She quickly grabbed a towel and laid it out in the middle of the bed. No need to lay in cum and whatever might spill.
She stood there for a moment just to make Diego suffer just a little bit more.
"Okay sweetheart keep it in and sit down and then relax. Don't spill any on the floor." Eudora instructed him as she pulled the door shut. Diego quickly moved. After a moment she heard him whining and flushed the toilet. He opened the door and pouted, his legs shook slightly and he was moving back and forth shifting his thighs and ass.
"Do I really have to do that again? Isn't once enough?" He pleaded. He really didn't like it but… it wasn't too bad. It wasn't intolerable. He just really didn't want to do it again.
Eudora came over and grabbed his chin between her thumb and pointer finger gently lifting his head.
"I'll do it for you and I'll use nice warm water. Don't you just wanna get it over with so I can eat out that cute little ass. After this I can get my mouth on you." She says and stares into his eyes. He lets out a shaky breath and nods. He steps back to get in the same position.
"Thank you, mommy…" He mumbled quietly. Eudora hummed and smiled when she noticed his cock growing heavy. She took the now used enema and tossed away the now dirtied tip and grabbed the clean new one from the box. She turned the tap on and waited for the water to grow warm but not hot. She filled the bottle up and screwed on the new tip.
"Diego, baby, you're doing so well. This one is going to go halfway and then you let it out and do the other half. You don't need to hold it in very long. Do you want me to stay in here or close the door?" Eudora asked and used her hand to spread his cheeks again. Diego tensed and then relaxed.
"You can stay… Please don't watch." Diego says and Eudora slips the tip back in. It was much easier this time. She gave it a short squeeze and then pulled it out. Diego thought it felt kind of… not bad. Not good , but not bad.
He stood still for a few moments before Eudora patted his back.
"Go ahead and let it out." The submissive quickly moved and looked down, blushing fire red. Eudora refilled the small bottle with more water. There was a short splashing noise and then Diego wiped and flushed.
"Mommy… um… Can I ask you something?" Diego said nervously as he cupped himself where he stood. Eudora cocked her head and looked at him.
"Yeah baby, always. What's wrong?" She says and keeps her distance. Diego just keeps his eyes down as he speaks.
"I… don't think I want you to… to put your mouth there. I just want your fingers and and my toy. I'm sorry Mommy." Diego says nervously. She had just done all this work so she could eat him out but he feels… he doesn't want it. He feels like he's still dirty and gross even after the long shower and the washing out.
Later he realized he didn't feel dirty because of anything actually dirty but because of the hair around his hole.
Eudora steps forward and kisses him. She lets her hands lay on his hips for a moment before slipping them down to grab his ass. He gasped and she slipped her tongue into his mouth. He let out deep little moans as she ran her hands up under his shirt. She lifted it up as she ran her hands up his back.
This was the start. The peeling away of his last safety layer.
They pull away and Eudora pants while Diego just looks at her with unfocused eyes. She quickly flicks the shirt up off of his body and he lets his arms wrap around her under her arms. He pressed his own nudity against her.
She was clad in a lacey see through bralette and a pair of nice matching black lace panties. He groaned and pushed his chest up against hers. He always liked the feeling of lace rubbing on his chest or on his cock, plus in his foggy dumb little brain
Eudoras boobs were the best things ever in the whole world. The way the soft skin moved and the way her nipples hardened when he rubs on them.
"Hey~ Diego~ Earth to baby~" Eudora said and lifted up his chin where he had been staring down at where their chests met as he pulled back and squished her breasts back up. He looked at her and nodded. He was ready.
Eudora grabbed his hand and walked him to the bed.
"Do you want to get your collar or do you just want to be my baby without it?" Eudora asks quietly as she stepped into the strap on. Diego shook his head and got on his hands and knees on the bed. Eudora situated the straps and knelt behind him.
"You look beautiful like this. Really beautiful but…" Eudora said and pulled on Diego's elbows so he fell onto his forearms. He was face down, ass up now. He whined and thought about how embarrassing it was. He was out on display, his cock hung heavy between his thighs, his hole was just out and open and still kinda wet…
Eudora bent down and kissed his right cheek and then bit it. Diego jumped and whined as Eudora licked the spot.
"Even better. So perfect. You look perfect. Now this may be cold but it'll warm up." Eudora said and popped open the cap on the small bottle of lube. She slicked two of her fingers and ran her pointer around his hole. She had done this a few times now while giving him reach arounds or blowjobs.
He hummed in pleasure and relaxed, easily letting the finger sink into him. Diego clenched a little bit but relaxed again as Eudora started to thrust her finger in and out.
"Gotta get you all slick, you're so hot inside. Look at your little prick, it's already dripping! Dirty boy." She said and slipped in the second finger. Diego moaned and sighed and stayed relaxed. His cock was hard and red and oozing a steady little stream of precum dripping down connecting his tip to the towel under his hips.
When Eudora bent her fingers and tapped slightly on the spot Diego moaned loudly and pushed his hips back and clunked his forehead down between his clenched fists.
"Momm-mommy… ah ah mommy that's my sp-spot!" Diego cried out and Eudora pulled her fingers out. She opened the lube bottle again and let a few drops fall right onto his hole. Diego tensed and whined.
"I know that's your spot. Look at your prick, all drippy and wet. Are you gonna cum from just me pushing this inside? Huh when I fill you up?" Eudora says and sits up and rubs the tip of the dildo around his entrance, fueling his moaning. He rubs back onto it and tries to push himself back on it. Eudora grabs his hip with one hand and taps his hole with the soft silicone for a moment.
"Please mommy! Please, please, please, please I'm gonna cum!" Diego cries out and yells out loudly as Eudora pushes through the slick rings of muscle. Diego trembled and tensed up he let out loud ' Ah ah ah' s. Eudora pulled back but Diego quickly tried to grab behind him and grab her.
"No! No more! I can't again…" He whimpers. His entire body shook and his back heaved with deep struggled breaths.
Eudora instantly held still and tried to figure out what was wrong. Did it snag a hair? Did it hurt? Not enough lube?
All the questions she answers ended when Diego slowly pulled himself off the toy and flumped onto his side. His thighs still trembled. His eyes were fogged and dazed and he was sweating. Eudora looked at him to see if he was hurt but…
"Aw~ Baby boy, did you cum? You really cam… I didn't think you'd actually be able to cum just from… the back. Wow… okay, okay, okay breathe easy and let me just clean up a little." Eudora said. Diego's cock was slowly softening and his spend was covering the towel.
Diego didn't answer, he just laid there and closed his eyes.
Eudora was in awe as she folded the towel and put it on the floor and took off the strap on. She unfolded their blanket and pulled it up over the man. She laid down and pulled the pillows that hadn't even had the chance to get used up to the head of the bed. She reclined against them and pulled the dazed man up to straddle her and lay against her chest. She gently rubbed his back up and down.
An hour later Diego perks up from where he was sleeping on his side of the bed. He was wrapped up in the blanket still naked. He sat up and winced. His ass hurt . He stood up and found a pair of his sweatpants. He walked out to see Eudora looking at something on her laptop. She stood up and came over to him once she noticed him.
"Hey there's my little porcupine. How do you feel? Come sit down, let me get you a drink." Eudora says and cradles his face in her hands. Diego nods and yawns as he goes to sit down on the couch. He sits down and winces again and ends up leaning against the arm of the seat.
Eudora returns with a glass of water and sits down next to him on the couch. She sat down and rubbed his feet while he took a bid drink.
"My ass hurts kinda… sorry I kinda ruined the fun…" He said quietly and flashed his eyes up to her.
"You didn't ruin anything. That was probably the hottest thing I've ever seen. Now for your bottom, how about you go get a nice long hot bath and that should help. Did you have fun, though?" Eudora said and Diego fidgeted a bit before answering.
"I had fun… I feel kinda…" Diego said and trialed off and put his hand on his lower stomach. Eudora thought she might know what he was wanting.
"Kind of what, baby?" Eudora prompted him to finish. Diego drank the rest of his water and handed it to his girlfriend.
"Empty. Can you… Will you put my plug inside? Just for my bath. I can take it out after by myself." Diego said and blushed again. Eudora smiled and got up.
She put the glass in the sink and walked to the bedroom. She came back with the bottle of slick and the small plug. Diego took a deep breath and tried to calm the fire that was starting in his belly. He felt excited, very excited.
"Hands and knees, only for a second. While you sit in the bath I'm gonna make a snack run so we can just relax and watch a movie after dinner. Want me to get you some M&Ms?" She said as Diego rolled over and up onto his knees, holding onto the armrest.
"Yes please… and some Twizzlers please." Diego said and Eudora hummed a yes and pulled down the sweatpants. She spread him open with one hand and rubbed a bit of slick around the outside of his hole and then pressed the cold plug up to his hole. He jumped and clenched up.
" Cold! " He whimpered and she kissed his lower back.
"Sorry baby. Remind me next time to warm it up. Now relax and it'll only be cold for a little bit." Eudora said in a pity laced voice. Diego sighed and relaxed his hole and let the metal slip into him.
His breath caught in his throat and he tensed as Eudora pulled his pants back up. She patted his butt and stood up to find her shoes. She was just going to the convenience store so the sweat pants and old ratty T-shirt were fine. Diego moved to stand and stumbled.
"Are you okay? Does it hurt?" She said and came to his side. His hands were shaking slightly.
"Feels… heavy. Nice. It feels nice." he stuttered out and his eyes flashed up and then he breathed out. He stands up and walks awkwardly to the bathroom.
Oh yeah… Eudora is definitely going to have to explore more about this new side of her baby...