Jack was in love with Jessica. It was an open secret between them, unspoken but potent, a gravity that shaped both their lives. Unfortunately for Jack, Jessica, his one true love, was also a shameless tease. She loved nothing more than flirting with boys – seeing how much a man would do to please her had become something of a sport for Jessica. She kept a diary of her favourite conquests – the silly, servile things she could make boys do in service to her full lips and fuller figure.

Normally, sooner or later, even the meekest of the guys she teased would make a move, and Jessica either bedded them or broke their hearts. Jack was different. Slender, geeky and incredibly self-conscious despite his boyish good looks, Jack felt luckyJessica even gave him the time of day. Still, a little possibility is better than none, and Jack figured every second they spent together was another tiny chance. Better to wait till tomorrow for another sliver of possibility than do something as terrifying as telling her how he felt.

After a year of such little chances, the most intimate Jack got with Jessica was helping her prepare for her dates and club nights. At least once a week Jack followed her round a mall or sat at the end of her bed and gave her a ‘guy’s eye’.

“This is what’s great about being friends with a boy… I mean a man... I mean... you know what I mean. You’re nothing like other men, you know… I can trust you. I think if I was in here with most guys we’d have our hands all over each other in seconds” she told him once in a changing room. She loved the crimson glow of his lust and humiliation as he zipped her into outfit after outfit, using his soft boy’s eye to find the perfect outfit for some hard man to rip off of her.

Jack didn’t mind – in fact, now he’d accepted it, he’d come to like it. It was an opportunity to stare at the most beautiful woman in the world without worrying about getting caught. He even got to tell, out loud, how perfect every part of her body was. Sometimes it felt a little like she was laughing at him, or there was some big joke he didn't get - but he told himself he was just being paranoid.

Jack was a gentleman by instinct and, at first, he tried to keep his comments , modest general and appropriate. He soon found hat wasn’t what Jessica wanted. If he held his tongue, pretending not to gawp at her curves, she’d direct his gaze round her body as if she were stress-testing his libido.

“How do my tits look in with the push-up?" she’d ask, leaning forward to show off her bulging bust. Jack, a half foot shorter than Jessica t withouher heels, was often made to stand on chairs or tables, so he could see how she looked to the tall, muscular men Jessica preferred. Conversely, she made lie on the ground as she walked round and over him, so he could assess which skirt best showed off ther ass, or which heels made her already heavenly legs impossible to ignore. Week after week he told her how badly any man... any man, just like him... would want to be  her. Week after week she thanked him and ignored the clunking hint.

Still, as Jessica well knew, you can only stretch a man’s heartstrings so far. Sooner or later, she knew, something inside Jack would snap in two and he’d run for the hills – or become hers forever.

----

“You look p-erfect.” Jack said as he watched Jenny twirl and shimmy in a silky red dress that screamed of scandal.

“Oh, Jacky... you're so sweet. I love that we can do this, you know? We have something special” she glanced seductively at him, biting her lower lip. Jack’s mouth went dry and his heart skipped a beat.

Jenny leaned so close her cleavage almost touched the tip of his nose, and whispered “You’re not like other boys, Jack. I don’t need to worry around you… I can do whatever I want. It’s like you're just one of the girls, I guess?”

Jenny pecked his cheek lightly and smiled as if it were a compliment. Jack felt his head begin to spin as his cheeks flushed pink.

“I'm gonna try one more. 'K babe?”

Jenny had barely closed the door before Jack was touching himself. He jerked helplessly as he imagined Jessica’s perfect body. He was almost at climax when the click of Jenny’s approaching snapped him out of his reverie. HJack scrambled to cover himself before she opened the door.

“Are you OK?” Jessica tilted her head. A sneaky smile peeked rfrom the corners ofher mouth “You look flustered. Is it this dress?” she asked, giggling and spinning around. The tight silver dress shimmered as it rode up, hinting at the tantalising roundness of her behind.

"Perfect, isn’t it?"

Jack nodded, too nervous to speak, afraid he’d let on, afraid that, somehow, she already knew.

Jessica stood barely three feet from him, running her fingers through her long, red hair and and pushing her chest forward. Her nipples bulged like bullets beneath the fabric. Shockingly small, sparkly and silver, it hugged Jessica’s hourglass figure at all the vital points. It was so low cut Jessica’s breasts seemed in constant danger of escaping.

It's fair to ask why Jack, a bright, plain, bookish young man, didn’t question why such a beautiful woman was shaking her body in his face. Perhaps Jack didn’t want to jinx a good thing, or perhaps his friend at her word: that she saw him as safe and sexless. That was surely more likely than her teasing him on purpose. After all, what could a girl like Jessica want with a boy like Jack?

Or perhaps it was that Jack could be smart or horny but not both. As her beauty intoxicated him, his wits surrendered. He laughed at her jokes, tripped over himself to agree with her every opinion and stutterred helplessly as he showered her with flattery and favours. Jack would anything to be close to her. Anything to see her smile.

“It's g - gr... It's -”

“Yeah it's great, I know,” Jessica said. “The place I’m going tonight... it’s got a certain kind of aesthetic, so I need you to be honest with me,” She told him seriously. “Do I look slutty wearing this?”

“I w-would never use a wor-”

“OK, but, pretend you’re, like, a normal guy. What will men – you know, real men – think? Thatk I look like a slut? Like I’m trying to get laid,” Jessica’s voice was tinged with irritation. She often got annoyed when he tried to be a gentleman.Other times she told him how sweet he was. 

“Um... It’s bold... and revealing... it’s going to make a lot of m-me-me-men think about,” Jack gulped then rushed through the rest of the thought, “what’s under it.” Jack’s hands were still covering his crotch, holding the material of his jeans over his still stiff dick. Beneath his fingers, he grew even harder as he imagined Jessica naked. “Sorry,” he whispered, staring down.

“So I look like I’m trying to get laid?”

“Maybe g-g-guys might think so?” Jack offered. He felt confused, his mind a pulsing mass of hormones.

“So you're calling me a slut?“

“What!? I mean n-n-no! I mean I’m-m s-s-sorr-”

“I’m kidding. I know you don’t see me that way... you’re too sweet. My darling little Jacky. But, you know how it is... if I wanted to fuck a sweetie pie, I’d stay home and seduce you.” Jessica laughed at the absurdity of the notion. Jack tried to sound convincing as he joined in.

“The guys who see this dress and think that bad word you don’t like? S-L-U-T? Those guys who know how to fuck. And I don’t gotta worry they’ll stick around for breakfast or whatever. If I want cuddles, I’ve got you.”

In a single, graceful motion, Jessica fell onto Jack’s lap, draping her arms round his shoulders, her ripe breasts close to his mouth. Jack was sure his erection was pressing into her thigh, but if she felt anything she didn’t let on.

Jessica held Jack close. His lungs filled with the scent of her perfume. Jack imagined burying his face in her cleavage, but instead, he looked up and stared into her deep green eyes. For a perfect moment imagined they might kiss.

Then, sudden as cruelty, Jessica was on he feet again.

“I wanna try this dress with the Louboutins. Be right back, babe,” Jack ran his eyes along the curve of her legs, high-heel to stocking-top, as she walked away

“Be good,” She told him. Jack could have sworn he saw her wink as she closed the door.

Jack felt weak, like it was inevitable. He should just get it it over with. It wouldn’t take long...

He pulled his pants down just enough let his little stiffy free. Gripping it with thumb and forefinger he closed his eyes and imagined Jessica - Jessica’s curves, her confidence the way she moved. He imagined Jessica leaning in close, her heaving cleavage mere inches from hi-

“What the fuck are you doing?”

In her $500 stilettos Jessica towered over him like a vengeful goddes, but the smile on her face looked more amused than angry.

Jack leant forward, trying to hide his hardness.

”N-n-othing!” 

“‘N-n—nothing', huh?” Jessica teased, as she sat next to him. Without warning, she reached between his legs. Despite the shock, Jack was rock hard, his penis shuddering in time to his pulse, dripping cum as it trembled. He'd been hard around her so often before it had begun to feel normal, but this was different. She’d never touched it before, except sometimes, accidentally through his clothes. Those had been accidents, right?

Her long pink nails felt sharp against his bare skin as she caressed him. Her fingers drew a slow, teasing spiral, starting at the head and working her way down.

When she reached the bottom she poked the base of his stiffness with a single outstretched finger then worked her way upwards agonisingly slowly, never breaking eye contact, till at last the tip of her nail met the tip of his prick. Gently taking care not to scratch him, she circled the head of Jack’s glistening dick with her finger, collecting his precum in her long, expensive fake nail.

“Woah, Jacky you are so small! And so hard too... kind of like a diamond, except girls dont want this little thing, do they? There really is almost ‘n-nothing’ down there” she giggled. She was being playful, as if Jack should be laughing along with her,  and that somehow made it worse.

She held up her finger, its wetness undeniable evidence of his passion. “

Is your dick crying, Jacky? Does it feel guilty about something? Or is it just sad that it's so tiny?"

Tiny. Jessica stated the word as an absolute, no argument or appeal. Jack's entire body tensed up as his neuroses came to life.

“I... I... I...”

“You, you, you… have a tiny little dick.” Jack whimpered. “Yes, you do. Yes. You. Do. It's OK. I mean... it’s not ‘ok’ OK. It’s not like girls don’t mind, no matter what they’ve told you. I just mean I already kne. I've known for a long time. Remember after Kelly’s party, when I sat on your lap in the car? Your cute little hardon pressing into my butt cheek the whole way home? At first, I thought I thought it was like, a coin or something.” Jack could feel himself getting redder and redder. He didn’t know whether he should feel angry or apologise.

“Hey, don’t look so sad! Before that night I thought you were impotent because there was never a bump down there, even when you were starting right at my tits - newsflash, by the way, you are not subtle about that stuff. I wondered if you were gay for a hot minute, but gay guys don’t whimper when I brush past them, or stutter every third word if I wear a tight sweater. But after the car ride, it all made sense... you were just too little to make a difference.”

“I'm s-s-”

“You're sorry? For what, babe? For having an itty bitty clitty? Or playing with it behind my back?”

Jack looked down, unable to meet her gaze. She grabbed him by the jaw, gently but firmly overpowering him, like a lioness mawing her cub. Jack stared deep into her eyes as he searched for some kind of explanation.

“I-I-I--!”

Jessica pressed her precum-slick finger firmly against Jack’s lips, instantly silencing him.

“Hush. Shut up and suck. Show me how sorry you are by swallowing the mess you made.”

Jack stared into her eyes. They weren't cruel, just demanding. They belonged to a woman who found not getting everything she wanted utterly unacceptable. A woman who, upon finding that all men desired her, had used that gift to get all she desired. The deep, green eyes of a woman Jack couldn’t imagine saying no to. Trembling, Jack opened his lips and began to suck, tasting himself on her finger. It made him feel weak, like Jessica’s little bitch, but all he could think about was how much he loved to be near her.

“Look at me when I’m talking. Eyes, not tits. Suck it clean. Use your tongue, round and round, get every last every drop. That's a good boy.” Jack felt his dick throb and his pulse quicken. He wanted to be a good boy for her so very, very much.

“You know, a lot of guys worry they’re small. They’re terrified of it. Most of the time they're  just average, perhaps a little under. Not you though…  You're special."

It took Jack a moment to remember that 'special' wasn't a synonym for 'good'.

"I spoke to a few of your exes. They used lots of words to describe your 'manhood.’”

Jessica smiled and licked her lips. Jack’s heart was beating like a drum.

“W-were they mean?” he asked, instantly dreading the reply.

“I thought so at the time. Now I see they were just being honest. And they all felt sorry for you, or at least found it funny. But whether it made them laugh or made them cuss, they all agreed on one thing: you – Jack Lille – have the tiniest dick they've ever seen.”

“All of them said that?”

“Every one. Didn’t matter if they’d been they’d been with 4 guys or forty.” Jessica poked Jack in the chest with her finger and let it slide down “Do you want to know if I agree?” Jack let out an involuntary squeal, half fear, half anticipation. Jessica grinned and twirled her finger round the head of his cock once again "Shh. Suck now, whine later. Suck my finger like a dick little Jacky, bob your head up and down... thats a good boy. A lucky boy too. Because I knew a guy... one of the first guys I knew, actually – who was super, duper small. Itty bitty. Barely 4 inches. I still have a photo, somewhere, if you don’t believe me. Lots of people don’t – he was shorter than my lipstick when I twisted it out.” She paused for effect, “You must be bigger than that... right?"

Jessica peered down. Instinctively, Jack tried to cover himself, but she smacked his hand away like she was swatting a bothersome fly.

"Sit on your hands if you can’t control them," a cold glance from her gorgeous eyes quenched any ember of a chance she was joking. Jack obliged, mutely pushing his palms beneath his backside. Complying made him feel small all over, not just between his legs, as if he were nothing but a speck of dust that could be blown away in an instant by Jessica’s perfect red lips.

"Oh... sweetie. You poor, tiny, little bitty thing. I think I have to agree with your exes... I think it’s the smallest one I’ve ever seen. It’s gotta be less than four, right?" she raised her eyebrows, pulling her finger from his lips so he could answer.

"Actually it’s… I'm fi.... almost fi... nearly?... four and a half? Um... inches," Jack muttered, begging her not to question it, hoping the very weakness of his lie might make her take pity on him. Instead, a smile spread across Jessica’s lips and she laughed openly at the absurdity of the attempt*.

“Does that usually work? Pretending to be small, so people don’t know you’re tiny?”

“It’s not tiny it’s just l-little. A l-little below average, I th-th-th,” Jack had been fighting them back but it was no use, he could feel his eyes moistening with tears of humiliation as the woman of his dreams belittled him. Trading away the last of his dignity, he looked over at her, let her see him cry, taking a final chance that, even if she’d never want him for being a big man, she might at least pity him for being a little boy. Jack knew it was hopeless, that he was only inviting more ridicule from the girl he’d at least thought was a friend.

But Jack was wrong.

“Oh, you poor little baby… now you’re crying up here and down here” Jessica said, wiping a tear from Jack’s eye with one hand and playfully squeezing the head of his dick with the other “why so sad?”

“B-because you’re… Jessica, you’re being mean… you’re being mean to me and I l-I lo-”

“I’m not being mean. I’m telling you the truth. You have a dick so tiny it makes you cry.” Jack had been holding back his sobs but now, as if in agreement, he let out a series of high pitched, effeminate whimpers.

To Jack’s suprise, Jessica put her arms round him and squeezed tight, rocking him back and forth like a baby. She stroked his hair gently, his cheek flat against her bosom. Even as Jack was at that moment - half naked and rock hard for her - Jessica still treated him like a harmless puppy. She knew that she’d made him lose his mind with lust. Now she was idly pressing his face between her breasts, as if daring him to kiss them.

Jack spent almost a year feeling secretly horny whenever Jessica was close. Now the truth was out, he felt a sudden irrational urge to confess. As though that tardy truth might undo eleven months of lies.

“Um… Jessica?”

“Feeling better yet babe? It’s not so bad, is it? Being tiny?”

“No… I mean yes… I mean- I mean, I feel like I should tell you, This is t-t-turning me on.”

“That’s ok. I don’t mind. I’m glad you told me, even if it was fun pretending not to know.” Jessica smiled. “I admit I’m a little offended you thought I hadn't noticed. I caught you staring at me before I knew your name. You get flustered if I so much as hold your hand. When you get really worked up, you breathe heavily like you just ran a marathon. Then when you try and hide it, you let out these soft little moans.” Jessica imitated the noise, soft, high pitched and orgasmic.

The smell of her perfume, the feel of her skin on his cheek and now the almost impossibly erotic sound of Jessica’s moan almost made Jack cum. He squeezed his thighs tightly together and bit down hard on his lip.

“I’ve seen you do that before too,” Jessica teased. “Usually right before you run off to the bathroom…”

“You knew??”

“You really thought you were keeping it secret?” Jessica giggled. “That is just SO funny… wait till I tell the girls.” Jack gasped. “I’m Kidding! I won’t tell them. Probably… Listen, now you’re being honest about everything… I know that little thing isn’t five inches. And I know a boy like you’ve measured it. You had to be curious just look at it… it’s like a scale model of a real man’s cock.”

She was right, as always. Jack had measured it, more than once, then gone deep into denial in the days and weeks after.

“Four?” he tried, knowing on some level he was wrong, hoping Jessica might finally let the matter be. Instead, Jessica rolled her eyes and stood up. Grabbing Jack by the shoulders she pushed him backwards onto the bed, then stepped forward, pushing his knees apart, and looked down.

“Four inches?” Jack gave a quick, nervous nod.

For a moment he thought she'd kicked him in the balls. Looking down, Jack could see the pointed toe of her ruby heel pushing into his pelvis, whilst the bright, gleaming red stem stood side by side with his stiff, pink dick. With one foot on the ground and the other pinning him to the bed, Jack could clearly see her black lacey thong. It seemed to shimmer a little, as if wet through.

It must be a trick of the light, thought Jack

Jack was so hard he was trembling. Dwarfed by the stiletto, his dick looked like it was cowering in awe before the burning, red sexuality of Jessica’s heel.

“Did you buy me these ones?” Jack nodded “still paying for them?” he nodded again “I remember… you told me they were 100mm. Which is just a fancy way of saying four inches, isn’t it Jack?”

“A-aren’t they the ones you wanted?” Jack sputtered, desperately “I thought you’d like them.”

"I do love them. You always know just what I want. That's why you're such a good friend."

Jessica began casually running the tip of her heel up and Jack's dick. She toyed with his manhood almost absent-mindedly, first swirling her heel round the little bulge of his head, then gently kicking it from side to side, punctuating her words as she spoke. "I love my cherry-red-La-bou-tins!” she said, as her foot playfully overpowered his dick. Finally, Jessica pinned the little thng down, pressing it into his crotch with just enough pressure to hold it in place.

"Babe, time to come clean. You’re much, much smaller than five inches. In fact, your little bitch clit barely makes it halfway up my heel." For the first time that day, aggression crept into Jessica's tone, and it scared Jack in ways he didn't understand. "You're smart, Do the math. If your dick isn’t five… or four and a half… or four inches, how fucking tiny is it?' she grinned like a cat with a cornered mouse.

"I.. No. I'm not ev- I'm less than... It – it is five. But only if your measure in cent- centim-"

Jack could feel her transferring her weight, his dick slowly, gently being smooshed beneath the most expensive gift he’d ever given a girl.

“Shut. Up. It’s tiny. What is it?”

Jack looked down between his legs. Beneath the shiny red toe of her ruby heel, Jack could still see the little pink tip of his manhood poking out. Jessica was right… it looked just like a clit.

“It’s tiny,” he admitted.

"That," she unpinned him, "is better. Now apologise."

I'm... sorry. Sorry, I'm so small."

Jessica sighed.

"Don’t apologise for that, stupid. Apologising for things you can’t change is as bad as lying. You’ll say sorry to me today, and you’ll still be tiny tomorrow – so what’s it wort? No matter what you do it will always be tiny. Apologise for pretending to be something you’re not.”

“OK-K-K. I’m sorry for... I’m sorry for pretendingI didn’t have a t-tiny dick.”

“A tiny what?” Jessica mimed cupping her ear as if she’d misheard.

“A tiny.. a tiny bitch clit.”

The words rushed out of him with the last of his dignity, the last of his power. He felt weak as a kitten. Again, unbidden, tears welled up in his eyes, but if they were tears of sadness or joy, Jack couldn't properly say.