Author's Note: This is essentially a chastity humiliation story where Teddy is the dominatrix. I do not own the series or characters.
The story does contain incest, if that offends you do not read any further.
Written via request by one of my reader's and friend rbk2009. If you happen to like it, please vote and comment. Enjoy!
Because apparently a lot of people are going to hate it. But you know what, no one made you click on this...
Gabe Duncan always had a crush on his big sister.
Teddy already had a reputation as a major influencer. It only amazed Gabe how he never knew exactly how much she accomplished or anything, only that she was able to support herself immediately after high school. Now 18, she'd already left for college and moved into her own place, much to the mixed chagrin and relief of their parents, who continually remarked that her free-spirited life wouldn't last forever...
But God did she have those heart-stopping looks.
Teddy's breasts bulged against whatever she was wearing, eye-catching and appealing, and yet not flamboyant. No matter what she wore, it seemed to fit snugly against her rack, which always exposed at least a hint of cleavage. Her hair was usually dirty blonde, though she had recently dyed it brunette to look like Claire Foy for a shoot.
There were always video chats, done with her new friend Victor or ex-Beau, who helped out a lot with the family and remained a close friend. Gabe would've killed for theirs or even Spencer's view and time, having seen Teddy's previous boyfriends enter the bathroom with her dozens of times carrying a small bottle of lube or even a bra. Spencer once operated as the head of her entourage, a gaggle of preppy popular girls and handsome looking boys that orbited around Teddy nearly constantly.
While 15-year-old Gabe was on the outside.
After being cajoled by their parents, Teddy decided to rent her guest bedroom. Mom and Dad sent a few hundred bucks every month, leaving Gabe to contribute two hundred. And Teddy made sure to remind him what a favor it was...
Not that Gabe needed it.
God, every moment was like a special form of self-imposed agony. Every second, Teddy exuded sexual grace. Occasionally, Gabe was treated to the image of her walking around the apartment in her underwear or even in just a towel. She always relished in the attention, giggling and smirking whenever Gabe wasn't quite able to hide his obvious teenage infatuation.
There was no escape. Online, Gabe could see dozens of her Facebook photos, breasts barely concealed by a hand, or a light-weight jacket, dressed for orientation, seminars, dances, any outfit someone in a movie would love to see. Attached to every profile was a link to her blog, where a special contribution let those wanting to see just a little more pay for private pictures.
Gabe had never brought himself that far.
But he'd lost track of the times he'd masturbated to her. His adolescent mind had a whirlpool of scandalous images, swimsuits, dresses, spaghetti tops with her breasts spilling out. The whale tail of her thong peeking as she bent over. The time they went to a local water park and she lost her top on the slide, stepping up completely unembarrassed as she flashed those perfectly pink nipples.
Gabe couldn't help it.
He would start stroking, then his mind would drift back, putting these images into his brain. It became too much. Gabe was regularly watching pseudo-incest porn. There was this one that seemed almost plausible, and too easy to replicate in his small way. A stepsister who looked a lot like Teddy first caught her brother snooping through her dirty panties, then after an awkward laugh, decided to let him fuck her right on the bed.
It didn't take long until Gabe thought of acting out the fantasy.
Gabe didn't think about getting caught. It wasn't his plan to surprise her. He wasn't that desperate or dumb. But he guessed he didn't much care if she did. Outside of class, video gaming and dreaming of Teddy, there was some but not a lot of social interaction in Gabe's life, and certainly no sexual interaction. Besides, Gabe thought he could get away with it. Visiting at her place, he just waited until she left with Victor, rushing into the door and grabbing a small, pink thong from her dresser drawer.
The excited teen pulled down his pants and boxers to his ankles, already hard, stroking himself rapidly. It wasn't enough, so Gabe gripped the panties around his cock, thinking about what it would be like to feel his sister's cheeks bouncing back and forth as he drove his hard dick into her.
It was so soft, so frilly, Gabe had to sit on the bed, his bare big ass enjoying the feeling of her soft, clean sheets. He leaned back, rubbing himself with her underwear, lost to the world. Gabe was so close, so ready to cum in his sister's panties...
Suddenly the door opened.
Her right hand went to her mouth, covering her lip as her face transformed into a cold, condescending smirk. She was still dressed as Claire Foy, her hair expertly styled to stand up on the side, her breasts bulging out against the suspenders. Our eyes met and to Gabe's deepening shame, but he kept going, so close that he couldn't stop.
Then she looked down at her brother's cock, almost entirely hidden by his hand.
"Oh my God..."
Now his sister let out a small chuckle at the size of Gabe's penis.
"Well go ahead and finish BIG little brother," Teddy said. "That chubby cute thing must not get much attention huh?"
Gabe couldn't believe what he was hearing, and yet he couldn't stop himself, relishing in her attention. She looked at him almost as though bored, barely even considering his penis.
"Can I help you out?"
She shrugged, her hands clasping around her breasts. It was clear by the way she moved, there wasn't a bra underneath that chocolate-brown shirt. With one hand, she squeezed herself. The other finger went to her mouth, almost like she was modeling just for her brother.
Then Gabe remembered, he'd seen her put this very pose on Instagram.
"Or do you wanna see more..."
Her hands went forward, unbuttoning her cut-offs slowly, stretching out the fabric. She teased Gabe, moving the hem of the shorts down little by the slightest inch. His sister wasn't wearing underwear, and Gabe could see the smooth descent down where her pubic hair should've been. Just an inch or so more and the boy was certain he would see her vagina...
"That's all you get baby brother," Teddy said. "It's so sick you know, wanting to see your sister's pussy. But you wanna do more than just see huh? You want to fuck me, you really..."
Gabe came in front of her, spraying all over her panties and his red-black plaid shirt, his pants and underwear still around his ankles.
"Wow, that's a big load coming from such a chubby thing," She said with a wink.
"Are you sure you've everything Teddy?" Victor called from the other room.
"Yeah just a minute," Teddy winking. "Don't worry, we can talk later."
*****
"So how into me are you?" Teddy said, seated on the corner of Gabe's bed. "Are you like, in love? Have you carved our names into anything?"
"L-look, I'm really sorry Teddy," Gabe said.
"You're sorry?" Teddy said. "I just watched you cum! I mean, I knew you were like, looking at me and stuff, or that you had. But I kind of figured you'd grow out of it by now."
"I guess I never did..." Gabe said. "I'm sorry, I'll go home if you like."
"Don't be so melo-dramatic!" Teddy said reaching out to Gabe bidding him to pause.
She wasn't dressed like an actress now, though her hair was still brunette. Her pink robe was clasped around her, hiding much more than he had seen earlier.
"Pretty much everything on is some sort of family member," Teddy said. "I think it's like, all those hormones bashing against your horny brain, and being forced to live with each other, you know?"
"Yeah, plus you're like, gorgeous," Gabe said.
She laughed, and Gabe thought maybe this could be cool.
"I'm trying to be an actress," Teddy said. "So, what're we gonna do about this? Because Gad, not to be mean, but I don't really want those panties back for real."
"Yeah... I'm really sorry," Gabe murmured.
"Is it gonna stop at panties?" Teddy said. "Because I'll for real kick your ass if you cum in a bra. That shit's expensive."
"I won't, I swear..."
"You know, I kind of liked it," Teddy said. "Is that weird? Oh fuck it, it's totally jacked up weird, but you're the one who wants to fuck me."
She just kept going, somehow able to normalize her brother's perversion.
"It's like the fact that I'm so hot that you just have to take me. That you would do anything to please me. It's really, I don't know. I mean I've had sex before, but nothing like that kind of dirty power."
"I... I haven't had any..." Gabe whispered.
"You've never had sex?"
Then the eldest Duncan daughter reconsidered.
"No, you're right. I guess I knew that. So, I guess my question is did that help or make things crazier?
"I already masturbated thinking about it," Gabe said, way too quickly.
"Fuck, really?" Teddy said. "How many times can you cum?"
"I dunno, like six or so," Gabe said.
"Six or so? Wow, just when I thought your dick couldn't get any bigger!"
Gabe looked down, sheepishly.
"Right, I'm sorry, but there's no need to be so shy. There could be something in it for you."
"What... what's that?"
"Well, okay Gabe, I don't really want to have sex with you," Teddy said. "There's just something about the eww factor... but..."
"But what?"
"I just feel bad that you're a virgin. I think if you'd been fucked before, you might be able to stop being such a loser about things."
"So... can we?"
Suddenly Gabe thought he was about to get some, the desperation soaked into his teenage voice.
"Can we have sex Teddy? Just once?"
She laughed.
"I don't know," Teddy said. "This is so fucking weird. But I guess what gets me the most excited, what nearly got me there earlier, was seeing how desperate you were. There's something about driving you to the dirty place. If I was going to have sex with you..."
"Yeah?"
"If... and it's a big if, Teddy said. "I'd want to be in control. Like a full-on queen thing."
"You can be in charge!" Gabe agreed readily.
"Gabe," She said sternly. "I'm not trying to be mean, but you'll have to satisfy me in other ways. I'm talking about every embarrassing, humiliating thing I can think of. It's going to be a thousand times worse than when I made you be my slave as a kid. I'm going to decide when and where you cum, and who gets to know what a weird pervert you are."
"Anything!" Gabe said. "I'm serious, Teddy, anything, I'll be your slave."
The boy's impatient cock was already stiffening.
"Good."
She left the room abruptly, and Gabe reached into his boxers, pulling out the head of his 6" cock. He just got a stroke or two in before she came back, causing him to quickly shove his dick back inside his Hanes underwear.
"Oh I like that," Teddy said. "You're gonna ask permission from now on before showing me your cock, do you understand?"
"Yeah," Gabe said.
"Call me queen," Teddy said.
"Yes my Queen," Gabe said.
Her left hand reached out, showing him the pink underwear from earlier, a little crusty with his cum.
"Put it on," She said.
"What?"
"Put it on and I'll let you cum in front of me," Teddy said.
"Yes queen!" Gabe said, peeling off his boxers.
"One last warning!" Teddy said. "If I see that pathetic fat prick one more time without you asking permission, your queen's gonna slap you on those shriveled little balls."
Gabe gulped at this, then he nodded, crossing his legs and hiding his shaft as he slid the dirty panties up his thick legs, turning away from her so that the thong rode up his butt.
"You've an ass like Ivy's," Teddy said. "Has anyone told you that?"
Gabe blushed, not sure what to think of her comment.
"Roll over," Teddy said.
It should've been embarrassing how quickly he obeyed. Gabe's egg roll-sized prick was completely engorged, already bulging against the fabric of the panties. If it hadn't been so fat, he was sure it would've stuck out the top of the tiny triangle. Instead, a sticky trail of cum was already collecting on his penis, pressing against the tight fabric.
"You know a lot of kids use weird stuff to masturbate the first time," Teddy said. "You know I used a banana. Today is your turn."
Gabe's butt cheeks tensed up, bare in the dirty thong, completely exposed to his sister. She reached in between his crack to slide the tiny strip of fabric aside. With one hand she spread Gabe's ass, teasing him with the smooth skin of the barely ripe banana she revealed from behind her back. The boy shuddered, not sure what he should do.
But Gabe was too turned on to stop what was about to happen to him.
Gabe bit down on his lips, his brown eyes welling up with tears even before she pushed it into him. There was no lube, little compassion, just the twisted experimentation of his gorgeous sister, too accustomed to the way the world treats beautiful people to consider anyone else.
"OW! FUCK!"
It felt like it was drilling up inside of him, splitting him in two.
He'd never even thought about putting anything in his ass before. Gabe tried to force it out, shaking and thrusting but all it did was push his ass further down on the fruit.
"It'll be so much easier for you if you play with yourself," Teddy said. "I always do when I get fucked in the ass."
The image of her taking it in that perfect behind made the teen squirm with jealousy. Gabe's right hand moved to his cock, hiding behind the frilly little underwear he'd stolen from his sister. He masturbated desperately, pulling on himself as discreetly as possible.
But she noticed, letting out that teasingly lovely laugh.
But Gabe found that despite his initial reluctance, he didn't hate it. There was something about being pushed down by her on a banana. Something in the sensual feeling inside of his hole, in the tip of the fruit pushing up against his prostate.
"Fuck yourself," Teddy said, letting go of the banana. "I'll let you see my tits but you've gotta fuck yourself like a gay dude."
She let go of the banana and the boy's hand reached up involuntarily, grasping at the tip to drive the long fruit deeper. Gabe's face was still against the bed, his mouth wide-open in the beginnings of ecstasy.
Gabe didn't dare move from his position. He was almost humping his hand, pounding his hips against his wanton grasp as he looked up to watch his sister playfully teasing him, opening and closing her robe strategically so that Gabe could just make out the beginning of those beautiful curves.
She smirked, seeing his gaze, then she dropped the rope, standing completely naked in front of her brother. Gabe's face pressed against the bed, his aroused body gyrating against his hand, as if the force from the fruit was building the pressure inside his cock. The boy groaned in excitement. He couldn't help it, coming up close to the edge. Gabe stared at her bare pussy, small and dainty, just a little slit extending between her legs.
She bent over, hiding her sex from his view as she moved her breasts within inches of Gabe's face, teasing him by their proximity. She hadn't explicitly said it, but Gabe knew this was a look and don't touch situation.
"Oh, right," Teddy said. "I guess you've never seen a vagina in person before."
Mercifully she tilted back, spreading her legs to let Gabe see as she absently moved her finger over her lips, not to play with herself just to tease him into nulled submission.
It was all Gabe could take. He let go into his hand, bucking a few more times with the thrust of his hips, the warm, sticky, shameful semen spilling out into his sister's underwear with a force he'd never experienced before. Gabe quaked on the bed, clenching down on the banana stem inside of him, suddenly all too aware of the foreign fruit inside his virgin hole. He shuddered, the last few weeks of cum sliding out of his dick, splattering against her underwear.
Teddy let out a playful giggle, and left Gabe like that, the banana sticking out his ass like a new award she had claimed.
"If I'm gonna do this, there's gonna be some ground rules first," Teddy said.
"Whatever you want," Gabe begged. "I'll dress up however you want. You can put whatever you want in my ass please. Please, I can't stand being a virgin anymore."
"You must be quick, of course I don't think that's a problem." Teddy said.
"I'll be quick," Gabe said.
"I wanna make sure," Teddy said. "It has to be fun for me..."
"Whatever you want," the boy said.
"Well... There is something," Teddy said. "I don't want you to come for a week before."
"Okay..."
"No, no, I can't trust you to do that," Teddy said. "I can't even trust you to stay out of my underwear drawer."
"What can I do?" Gabe pleaded.
"Teasing you is the only fun thing I get out of this. So, I want you to wear a cock cage."
"A what?"
She explained, then drove us to a local adult store, where Gabe had to tell the clerk what he wanted... and why. He croaked out the words, explaining that he was too horny not to sneak into his sister's room to masturbate in her underwear. The aged disinterested clerk just rolled his blue eyes and pointed the product, apparently used to being unwillingly involved in freaky adolescent sex games.
The cage was small and plastic, with a bunch of interlocking bars. There was no way Gabe could possibly remove the thing from his penis. They had to try more than a few times; his penis kept getting hard with his sister's hand running along the shaft. Frustrated, she got an ice cube from the refrigerator and put it on the head of his cock and balls, giggling at his reaction until Gabe deflated enough to fit into the tiny sheath.
"Wait how the fuck am I gonna piss?" Gabe asked.
She laughed. It was strange how erotic Gabe was finding her mocking side..
"Like a girl, sitting down like a little girl."
There was a lock at the top of the shaft, a cruel looking miniature padlock with a key that Teddy hung around her neck.
With that, the longest week of Gabe's teenage life began.
One week of chastity and Gabe would finally have the curse removed from around his neck. Of course, there were so many other things distracting him, keeping his mind perpetually riveted on his perverse fascination with his sister's pert ass, perky breasts, and her bare jaw-dropping pussy.
God, I want her! I would've put up with anything to have her….
The sore, swollen head of his cock surging against the cage certainly proved that.
The hardest part to get used to was sitting down every time Gabe needed to piss. The urine didn't come out in a steady stream, instead it sprayed along with a slit in his sheath, sometimes dribbling down over his balls so that he had to use a piece of toilet paper to light between his legs, like a girl. Gabe didn't mind it so much at home but out in public...
His sister used the week to torture every inch of flesh, precious as they were, to drive him crazy. With Gabe locked up out of reach, she stopped wearing clothes around her apartment, rarely putting on more than panties or a shirt. After every shower, she let him dry her off, always brushing Gabe aside from his greedy hands reached down towards her pussy.
Teddy told him if he was good she would supervise a few showers to make sure that he kept his promise while he washed himself. Gabe now learned that being good meant willing to put a dildo into his ass on command.
At first, Gabe resisted, not sure how he would take it without being able to get hard.
"Oh, that's fine then Gabe," she said. "I guess you don't have to fuck me then."
Already, Gabe was stammering over himself, willing to accept everything, to be fucked by whatever she wanted. She could've put a Wii controller my ass, I'm so desperate!
"Not good enough little brother," Stacy said. "I'm gonna have to punish you."
She made him bend over her lap, taking a wooden table tennis racquet from the Rec room to his ass like some people in pornos did. Only she beat him red until Gabe started crying, tears spilling down his face. Then she spread his legs even wider, hitting him hard on the testicles with the racquet until every last piece of dignity shattered from his self-image.
The next day when she asked Gabe to fuck the dildo she bought for him, he actually ran into his bedroom to fetch it. Gabe looked at her the entire time, hoping that he had fucked himself good enough to avoid another punishment.
Luckily, he had.
There was a strange feeling as Gabe pushed the head of the toy into his ass. To the teen's surprise, it didn't hurt as much now. If anything, after nearly twenty minutes exploring his tender hole, Gabe felt strangely satisfied even without exploding into an orgasm.