Jack was in love with Jenny, and Jenny knew it. It went unspoken between them but not unacted on. Jenny was a shameless tease. Normally the guys she teased asked her out, sooner or later, and she was able to tease them more intimately, but Jack was different. Jack was shy geeky, and he knew his chances were slim to none with the hottest girl on campus. Still, he figured, every second they spent with her was another tiny chance.
A year of chances later, this was as close as he got to fucking his dream girl – watching her waltz in and out of the room in a series of outfits, asking him to pick which she looked best in. He got to say, out loud, how hot she looked, instead of just thinking it in his head over and over. He didn’t need to worry he was staring too much – indeed she’d ask him, specifically, how her tits looked, her ass, her legs. He told her over and over how badly he… any man would… want her. It was as close as he got to getting it.
Then, one night, something happened that was just too much for poor Jack.
“You look… perfect. Every man will want to be near you.” he told her, honestly, as she modeled a red halterneck for him.
“Oh Jacky… you’re so sweet. I love that we can do this and it not be a problem.” She leant over him, tits in his face, and whispered “It’s like you’re just one of the girls, you know?” She pecked his cheek and walked away “I’m gonna try one more babe, k?”
The door was barely closed before Jack’s dick was in his hand. He came in a half dozen strokes, then deliriously zipped himself up, astonished at his own lack of control. Then he sat and waited nearly five minutes for Jenny to return.
When she did, it was as if she could tell something was different. She looked at him oddly and asked him if he was feeling OK.
“You look flustered, is all.” she told him “Out of breath.”
That was almost a month ago, and it had happened again twice since. Both times he’d nearly been caught – Jenny seemed to return much more quickly and suddenly now, usually to pick up some vital object she’d ‘forgotten’. He should stop agreeing to help out. Yet here he was, in her bedroom again, his small but painfully hard dick throbbing against inside his jeans as she twirled.
It was the night’s third offering, a shockingly tiny, sparkly silver strapless dress that had been designed for a woman with her waist but much smaller breasts. They looked constantly in danger of escaping – though fifteen minutes of jumping, wiggling and jiggling had proven to Jack that they would stay covered.
It’s fair to ask why Jack, a bright man who excelled in his studies, did not see anything unusual in this beautiful woman shaking her body in his face. Part of his naivety came from a belief that there was no chance Jenny could want any kind of sex life with a boy like him. Even the most explicit display had to be an accident. It’s also fair to say that Jack, like many men, became very stupid when he was turned on – giggling at her jokes, tripping over himself to agree with her and stuttering out what little sense he could muster as he let himself be mesmerised by her.
“It’s g- gr-… It’s-”
“It’s great, yeah.” Jenny said “Imma just try one more.” Jack followed the curve of her legs, heel-to-thigh, as she left..
He had to get some relief. It would only take a second…
Jack undid his fly and let his little stiffy poke through the hole. He gripped it and began rubbing it… two, three, four strokes. Five, six, seven. He closed his eyes and imagined Jenny leaning over him, her cleavage almost touching his nose…
“What the fuck are you doing?” Jenny towered over him. She was taller than him by six inches in bare feet, let alone with him sat down and her in heels. She looked amused more than she did angry, but Jack nearly leapt out of his own skin regardless.
“N-N-N-Nothing!” he yelped, simultaneously letting go of his dick and doubling over in an attempt to hide it.
“Really? Was it ‘n-n-n-nothing’” Jenny teased, sitting down next to him and unexpectedly reaching between his legs. He was still hard despite the shock. His penis was quivering slightly in time to his heartbeat, dripping cum as it pulsed. He’d been hard around her so often it had gotten to feel normal – one of the few advantages of a truly tiny dick was nobody noticed it. This was new, though. She’d never touched it before though. Her perfect, sequinned fake nail felt sharp against his sensitive skin. She poked the base of his stiff little dicklet and began scraped upwards, all the way to the tip. She swirled her nail round his foreskin, gathering up his precum scooping up a little precum as she went. “Well… almost nothing. Look…” she held out her finger, undeniable evidence of his passion glistening on its tip. She didn’t seem surprised,. “See that? Your dick is crying. Probably because its so small.”
Jenny delivered the line almost absent mindedly, like a fact no one could take issue with, Jack’s entire body tensed up as his worst fears came true. His head swimming, he didn’t register the smile on Jenny’s face
“You you you… have a tiny dick. It’s OK. I’ve known a long time. Since you got hard when I sat on your lap in the back of the car. Before that I thought you were gay because I could never make out a bump down there, even when you should have been throbbing. That car ride it finally made sense… you were just too small to notice.”
Jack had always been embarassed about his size. He knew many men felt the same way – and some were twice as big as him – but Jack’s fears had been realized over and over. From the woman who told him size didn’t ‘usually’ matter, to the high school sweetheart who cheated on him, he’d brought five women to bed and each had left him a virgin. It was part of why he’d never asked Jenny out – he really loved her, and he couldn’t ask her, of all people, to pretend three hard inches was big enough.
“You’re sorry – for what, baby? For having a tiny dick, or for playing with it behind my back?”
Jack looked down, unable to look her in the eye. Like a lioness with a cub she grabbed him firmly, her clean hand on his jaw. Jack started up into the emerald pools of his best friend’s eyes for a moment that felt like eternity.
“Shhhh.” before he could finish apologising, Jenny’s precum-slick finger was pressed against his lips. “Suck it clean. Suck the mess you made off my finger while I tell you how we fix this.”
Jack tried to nod as she pushed her finger into his mouth. He could taste himself on her. Her eyes weren’t cruel – just demanding, and maybe a little spoiled. They were the eyes of a woman who would one day inherit eight figures in property, shares and cash, but never paid for her own drinks on principle.
She grabbed something from under the bed. It was a box, black wood with gold lettering: ‘PetKeeper-S’.
“A present. For you. For both of us.” she purred “Open it.”
Jack was sucking her finger like a pacifier as he peeled off the lid.
“Have you seen one before?”
It was smaller than the ones he’d seen online, and those ones had been metal grey, not bubblegum pink, but he recognised the chastity device instantly. It felt like the bottom was falling out of his world. Jenny watched his pupils dilate as he tried not to react.
“I thought you might recognise it. Ever seen one for real before. I have almost a dozen – I usually get a new one for each new guy. With you I had no choice – the cages I’ve got would be way, way too big. I talked to your ex, Cara, just to be sure.” Jenny giggled at her friend’s shock, then pulled her finger out of his mouth and stood up.
“I… couldn’t help myself.” He told her, meekly.
“I know. And I’m not mad. But I can’t hang out with you if you’re gonna be gross.” Jack nodded, downcast but understanding.
“Will I wear it forever?” he asked. Jenny shrugged.
“Nothing’s forever, but if you want to be my friend I need to trust you.
“W-w-will I be your b-boyfriend?”
“Yes. You’ll be a boy who’s my friend. Just like now. Or, by all means, leave now and jerk off over me all you want. Just don’t contact me again.” Jack gulped, the taste of precum vivid in his mouth as he swallowed.
“S-so nothing will change between us?”
“Oh, I wouldn’t say that. If you’re locked I won’t need to worry about you getting overexcited. Remember when I danced with you at the spring ball? I felt you have that little accident against my thigh.” Jack’s face blossomed an ashamed purple “So I stopped dancing with you. This would mean no more worrying about accidents like that. I might even try new stuff on you.”
“So I’d be almost like a secret boyfriend?”
“I guess. Just don’t ever call yourself that, particularly not round any of my friends, unless you want me to tell them the truth.”
“Did you keep the others s-secret?”
“My other pets? No. You’ve met a couple actually. The difference is, sooner or later, I ended up fucking all of them. With those guys I knew it was always a matter of time… but like I said, you’re special.”
Jenny pushed Jack backwards so he was lying on the bed “Because you’re a real pushover, Jack. The stuff you do for me… shopping, buying me dinner, carrying my purse. Usually guys don’t do that stuff till they’re wearing this.” She pulled down his jeans and began squeezing his balls through the ring “Say if you want me to stop by the way.”
Jack opened his mouth but no sound came out.
“You’ll like being my pet, mostly. All the others did… till they got naughty after I gave them too much pussy. You see, that’s why you’re perfect. I’m only human, and sooner or later I want to feel a guy’s cock inside me… but you won’t give me that problem. I mean look at this thing, jesus. It’s the hardest, tiniest dick in the world. Like a beach pebble. I will never, ever be tempted to fuck your itty bitty thing.” Jack’s head was throbbing, her words distorting in his mind. She was saying such hurtful things but she made them sound playful, almost loving. “Plus I kinda like that you’re a virgin. All mine.”
“Anyway, it’s make your mind up time. If you say yes without pretending like you need to think about it i’ll let you see these…” she nodded downwards “I know how much you like them. Anyway, your choice.”
Jenny was still wearing the same sparkly dress, so low cut he thought he could see the edges of her areola. As was often her habit, Jenny went braless, and tonight her nipples threatened to tear through the already strained fabric stretched across her bust. Jack stared at them, unaware of time, hypnotised by their size and perfect, swollen roundness, feeling their heave command the tiny, firm need between his legs. He nodded and moaned something unintelligible as he stared.
“Was that a yes?”
“Good boy” She pinched his dick at the base, inspecting it “Cara was right, it’s fucking adorable. Such a sweet, tiny, cute little dick. I’m gonna want to get it out sometimes just to look at it. Right now, though, I need it soft.”
Jenny flicked the underside of Jack’s penis firmly three times, just where the head meets the shaft. His erection withered within a minute, his dick shrivelling down like a candy wrapper in a fire.
“Don’t get used to this” Jenny told him as she rubbed spit and precum all over his soft dick, lubing him up for the chastity tube “I’m gonna want you to learn to DIY. You’re absolutely sure about this, no going back? Just stare helplessly if you agree.”
Jack stared helplessly.
Jack felt the belt tighten as she pushed the pieces together and forced the padlock closed. For a few moments his dick felt like a tube of toothpaste being finished off, then nothing.
“Do you feel that?” she asked, laying next to him
Looking down, Jack saw her pretty nails clambering all over the stiff pink shell imprisoning his penis. He felt like he might cry as he tried to imagine what it would feel like without the cage between her hand and his shaft. No… not his. Not any more. On some deep primal level he felt like he no longer owned the most sensitive parts of himself. They were hers now, her property to own, manage, indulge or ignore. He felt terrified by his own excitement.
“I- I- uh I-..” He bit his lip. He’d been about to say he changed his mind, but he couldn’t do it. He couldn’t bring himself to disobey her, disappoint her. Surely it would end badly. He’d always prioritised her happiness, of course, but now she owned those precious parts of him, pleasing her seemed utterly vital.
“Relax” Jenny said, her voice as casual as if they were sharing a drink on the quad. She held him close for a moment, pulling him off of his back to face her, then she shuffled round so they were spooning. She made no effort not to rub against his caged dick… in fact, she kept rubbing against him even when she was clearly comfortable. Grinding herself into him with a reckless nonchalance that made Jack’s pulse pound.
“I bet you can feel that… when I make it move up and down.” Jack could feel it, his dick moving slightly inside the cage, like he was getting the worlds gentlest hand job. He wanted to scream in frustration and beg for more at the same time.
“Oh God… Jenny… when will I get to cum again?”
“When I unlock you, I guess. Haven’t really thought about when I’ll do that. Probably when I’m in a real good mood. Unzip me.” Jack obeyed, unzipping the silvery dress. She pulled it down just far enough to free her tits.
“Do you want me to turn round?” Jack could smell her perfume as he stared at the back of her neck. He knew she was half naked next to him, and he had never felt smaller in his life. He’d never been so turned on either but his dick was a soft, useless inch. “Are you shy, back there? If you want me to turn round, kiss my neck.”
He kissed it, sweetly and passionately. She moaned with pleasure, power and satisfaction and she kept teasing his locked dick with her big round ass. When she’d had enough of his petting, she turned round, hands covering her tits in a playful burlesque. At the apex of her cleavage sat a tiny gold key attached to a chain round her neck.
“I bet you looked at these before you looked at my face. I noticed you staring at them. Before we were friends…and after.” she pulled her hands away, exposing herself to him. Her breasts seemed impossibly big to him, rising and falling in time with her breath. He stared and stared as every other thought in his head evaporated.
“You can look all you want Jack. I don’t mind. But hands to yourself. We wouldn’t want this key getting lost would we?”
“No! Please… I won’t!”
“I know you won’t. Not unless I say so. I think you need to learn a few things about consent, if we’re going to keep hanging out.” Jack nodded at her breasts “Consent means I’ll never make you do stuff you don’t want to. You can always say no. But it also means you don’t interact with me or my body unless I give you permission.”
“I understand” said Jack, barely able to comprehend
“So, for example, I won’t ‘make’ you tidy my dorm up while I go out clubbing. You don’t have to do it it”
“Likewisem I don’t have to let you play with and suck on my tits when I get home. It’s my choice.”
“Unless” she paused for effect “you wanna do swapsies?”.
Jack stared dumbly up at her, too horny to think any more, too horny to understand what was being offered. Jenny rolled her eyes.
“I go out. You do chores. If you do a good job, you get to play with these.” She squeezed her tits together and pushed them towards his face “Sound good?”
He thought the cage couldn’t get any tighter, but he felt like his manhood was being squashed out of him. His body tried desperately to make him harden, but the result was a soft, angry little cock bulging out of its pink prison, steadily dripping through the tiny hole at the tip.
“You know what, I don’t wanna feel like I’m pressuring you. ” She turned round again “You liked this dress right? Zip. Good boy. I’ll be back by 3… 4 AM latest. Probably. Just vacuum and water the plants, do the dishes, the laundry, clean the oven…” she was standing up now, picking up earrings, pulling on heels. “you know what? there’s a list on the fridge. Do all that stuff. If you want to, I mean. You don’t have to. You can just leave.” Jenny leaned across him to grab her phone, her cleavage gently bobbing at his eye line. Jack wondered how he could feel this way and not explode.
“Totally up to you. I’d like it if you did though. It’d put me in a real good mood.”
Jenny admired herself in the mirror for a moment, wiggling her ass at Jack as if she didn’t know he was there, before heading out.
The door closed. Jack was alone. Out of instinct he reached down to touch his enraged dicklet before the solid, insensitive feel of the tube reminded him of his new predicament. He lay there for a moment dumbly, trying to imagine leaving, then got up and began working his way through Jennifer’s list.
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