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 and 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 leaned 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. “I'll 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 leaped 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 it's so small.”
Jenny delivered the line almost absentmindedly, 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
“I... I... I...”
“You, you, you... have a tiny dick. It's OK. I've known for 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 embarrassed 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.
“I'm s-s-”
“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 an eternity.
“I'm sorr - !”
“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.”