The Seven Dressing Sins: Vanity

Story Info
An unsuspecting sissy porn star? How could that happen?
3.5k words
4.45
51k
25

Part 3 of the 3 part series

Updated 08/30/2017
Created 07/14/2011
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
purekink
purekink
582 Followers

"To recreate this scene, you will need..."

John tightened his calf muscles as he watched the young woman on the TV present an untidy scrap of cloth.

"One white fishnet dress."

He thought he knew her, somehow - something in her voice perhaps. He didn't know anybody with a crimson streak through her long blonde hair. And he certainly didn't know anybody who'd do a porn movie.

The camera remained pointed at her wonderful breasts. They were small but very firm, and semi-aroused nipples broke through black fishnet. Her gloved hand appeared again.

"One white fishnet suspender belt, eight metal-clipped suspenders."

John watched her dangle them, mesmerised.

"One pair of white fishnet stockings, deep lace welt."

The garments were almost invisible, soft white insubstantial promises of kisses of apparel. The narratress placed them gently on an upholstered chair. The camera moved back to let John see she was wearing black fishnet suspenders and stockings.

She turned, and the camera zoomed in, past the hands on her hips, to her crotch.

"Next of course, one pair of white fishnet tanga knickers with lace detail at the waist and ruffled seat. Tie crotch."

Hers were black, filmy and seductive. She wiggled slightly so John could see the way her alluring dress slid gently over the lace waistband. She turned and bent over, presenting her glorious arse to the lens. Rows of crisp black lace stretched across her netted derriere and John could see a thread of black lace stitching together a well crafted opening that would reveal its secrets at a tug.

"One pair of fishnet gloves," she said as she stood and turned around. She looked flushed at the collarbone as she waggled her fingers in their dainty mesh.

"Again white, and I much prefer fingers to fingerless - eh, girls?"

John smiled in spite of himself.

"One pair of white plastic knee boots, zip fastening and high-gloss. Six-inch heel."

She held up the shiny boots, white glittered in the light and contrasted her own pair in black.

"And finally, most important - don't forget this if you're acting out this scene at home - a strapon dildo!"

Her small hand clasped a monster.

God, thought John, that must be... must be at least... maybe -

"Seven inches long," the girl said, "A whole seven inches of pink cock. Seven inches of banging pleasure with open-crotch straps in pink leather. A bulging head for thrusting, a smooth pink shaft for sliding, and a pair of hot pink balls for grinding."

He fidgeted uneasily as she wafted it in front of him.

"That, of course, means lube - and plenty of it, This is waterbased, and tingles as it warms up... I love it!"

She waggled a blue tube before putting it down on a table.

"Let me explain how my games work. I create a perfect fantasy. And then I show you how to exactly recreate it. I'll detail your costume, your props, and your start position. As you watch me create your fantasy, you copy what you see onscreen. There are subtitles that will prompt you when you need to recite dialogue. The game will sense movement, and I will correct you if you fluff a line or move out of position.

"A safeword will be displayed in the bottom left corner of the screen. Should you choose to use it, and game will stop immediately."

The word flashed into the corner of the screen, glowing white characters almost daring to be uttered.

"So do you understand that sex should be safe sane and consensual and that Jane's Pegging Corporation accepts no responsibility for anything that happens to you should you decide to copy anything you see in this game?"

There was a pause, followed by the stamp of her foot.

"I said, do you understand that sex should be safe sane and consensual and that Jane's Pegging Corporation accepts no responsibility for anything that happens to you should you decide to copy anything you see in this game?"

"Yes," he yelped in surprise.

"What is your name, little girl?" she growled.

"John", he whispered.

"That's John, mistress," she said sternly.

"John, mistress!" he said.

"Well, John, shall we begin the reenactment?"

"Yes, mistress."

John met Katie through a friend. She was a quiet girl who was, according to the friend, some sort of rich star coder who'd earned a fortune doing something online. John hadn't paid much attention beyond the word "rich".

He'd started seeing her more because there was nobody else around - they hadn't exactly hit it off. He spent a lot of time at the gym, playing tennis, working out and toning, while she showed no interest in fitness or beauty regimes.

John was all ready to dump her - their relationship hadn't exactly overflowed with her supposed wealth and she'd been reluctant to talk about it when he pressed her.

But she'd saved herself for at least one more night when she'd snagged his curiosity earlier that day

"Do you want to try something really different at my place tonight?" She asked as she nuzzled his ear as he sat in front of a tanning lap, eyes closed, wearing a mud face mask.

"What is it?", he asked, intrigued.

"Something naughty I think you'll like."

"Er, sure," he replied.

He heard her feet padding away on the wooden floor.

"I said spread them!"

John tried to reach back even further to grab his buttocks, which meant putting his face to the hard wooden flooring. On the screen two handshapes appeared as a man held his arse open. As John moved his fingers, the hands changed shape until he matched the man's grip.

He opened up his arse, feeling the cool air against his glistening, oily sphincter.

"This is where we find out if you followed lubrication instructions properly during preparation!"

The woman moved closed to the kneeling man and shuffled into place between his fishnet clad legs.

"And we can just start to move your sexy little knickers to one side."

John felt Katie's warm, slim hands sliding the net fabric over his smooth-shaven balls.

"And now there's just the matter of... easing it in."

Katie's voice deepened as the words appeared on the screen. John noticed she barely had time to read them before she mouthed the lines.

But that fact didn't register for very long as he felt a pressure on his exposed entrance. It was insistent and irresistible, and despite his best efforts it popped through his resisting sphincter. He moaned loudly as the shaft filled him inexorably, insinuating itself into his tight passage.

"Oh, Christ!" he blurted out as Katie's thighs touched his.

"No talking without permission!"

Katie's hand spanked his right cheek as the instruction appeared. He flinched, involuntarily clenching the muscles in his ravished bottom.

"And now to turn you into my cock-hungry fishnet slut!" Katie and the subtitles declared.

John braced himself in anticipation. Blood flushed his skin and he could hear the whisper of his white fishnet dress as it flowed across his suspender belt in a lewd, bawdy hiss.

He curled his toes, feeling the stockings slithering against the smoothness of his legs and the slippery plastic boots.

Katie's knob moved out of him, before the powerful woman atop him clamoured hungrily at the gates to his very soul. But as she began to ride him there was only one question in his cock-confused mind: How had the game known about his fantasy?

John had awakened to femininity during his first year at university, that golden age of experimentation and discovery that saw so many flowers bloom.

Mary was his first crush, and the enduring influence on his sexuality. From the first time the chubby, leathered-up biker suggested living out her lesbian fantasies, John readily acquiesced to her requests to appear more womanly.

He'd blushed as she told him his smooth tanned skin was already turning her on. And when he shaved and dyed his pubic hair into a cherry-red heart for her, he'd received the finest blowjob he'd ever imagined he could have.

But it didn't take long for her to reveal she couldn't resist a handsome man in stockings. When she told him, John spent days trying to please her with his mouth - all the time waiting for the suspender belt he'd ordered from ebay.

Instead of being grateful, Mary asked why he hadn't ordered matching knickers.

As taught, he spread himself against the wall and waited for his punishment. Mary announced the price for orgasm with no knickers on: a strict whipping.

That day he took her oath and became her love-slave. Mary had humiliated, belittled and harangued him as she dragged him as she dragged him down the satin slope of womanhood.

But the the ultimate shame came as he begged her for cock while his head was tightly imprisoned between her legs.

"Beg me!" she ordered.

"Plmth lmee tay yuh coh!" John shouted, proud to be her beautiful pussy-slave.

"You'd love that, wouldn't you, you fucking tart? Taking a cock up your arse - you're such a fucking fag!"

Mary's hand slid up and down the length of his tortured shaft, imprisoned in red microfibre boyshorts and sheer red tights.

The corset he wore made it difficult to answer her, restricting his breathing and midriff.

"Come for me, my gorgeous tranny bitch!"

At that moment, John's world divided sharply into two. Men who allowed themselves to be forced into lingerie-clad ejaculation, and those who would not.

John's breathing changed with each flow and ebb of the pink pleaser being administered by Katie.

He'd lost - he could feel it. His struggle to keep his masculinity had been swept away by the sensations of a cheap hooker outfit. The fishnet dress rubbed every part of his body as he accepted Katie's stiffness.

"I think it's high time for the mirror - are you ready to see what you look like, slut?"

John nodded but could only grunt.

A slap - left buttock this time.

"I SAID: I think it's high time for the mirror, are you ready to see what you look like... slut?"

"YES" John shouted, startled at his own bellow.

"Yes, what?"

Another slap, onto his already-stinging left cheek.

"Yes, mistress!"

Katie began moving, turning him with the dildo embedded firmly inside his arse. He winced as a sudden burst of pleasure washed through him followed by pinpricks of exquisite pain as the shifting replica cock brushed against previously unsuspected nerve endings.

At least it answered the question about the black silk sheet. Katie stretched forward and grabbed it with her red-tipped talons. As she pulled, John's penetrator moved again, and he groaned as it pulsed delight into the core of his being.

A core that burst alight as the sheet floated gently to the floor and uncovered the reflection beneath.

John's mouth fell open as he beheld his own buggering. He'd seen what was happening to him in the game but there had still been that... separation... between his own ass-fucking and the one being meted out by the digital dominatrix.

The mirror, however, couldn't disguise the whore dressed in a fishnet dress, knickers, suspenders and stockings that were tipped by flailing white plastic boots. That was him. John. Such a masculine name felt ridiculous attached to the panting and desperate wretch who writhed and gasped and cried out in lipsticked horror and blonde-wigged despair as her own desire was stoked by a firm thrust that echoed with a meaty clapping noise.

Katie was plumbing his most intimate depths with her female stiffness, riding him at a grinning canter that battered at John's reluctance. With each slamming measure of fulfillment and surrender, John gave himself over to the bliss delivered by his girlfriend's eager, passionate fucking.

He arched his spine to align his opening with Katie's member, taking a deep breath as he guessed her next move.

His reward came a split-second later as the fake cock ploughed effortlessly into him in one swift, smooth stroke. Stars lit up behind his painted eyelids, tiny tears in the corners of his eyes threatened to make his mascara run and his scarlet lips formed a dainty hoop of thrilled surprise.

"Yeeah, you little whore - now you're mine," said the game, "and..."

"This is Katie!" shouted John's girlfriend.

A mechanical voice on the TV intoned: "backdoor, miss?"

"Yes!" shouted Katie, matching the deadpan rhythm with her probing, emasculating humping.

"Ohhhhhh," breathed the TV, "My mistake, slave girl. I meant to say you're the fucktoy property of Queen Katie, whose cock you are not fit to take. Who do you think you're fooling? All those fucking facial-masque deep-pore anti-dandruff bullshit potions you slap all over your body? All that working out you do? And you shave your pubies, too?"

John looked around in shock, tearing his gaze away from Katie's masterful fucking.

At that moment the woman leaned into the camera.

"Oh, I think you've been feminised before. Some are cockerels, John, and some are capons."

His mind suddenly ordered itself. The television was showing his girlfriend's face and taunting him about his fetishes.

"K-Katie?" He managed to stammer.

"That's right baby. Just like you dreamed - two girls at once," Katie said, "Do you want to know how?"

"B-but that's you!" John managed, as Katie leaned over him to rub her breasts on his back as she drove her hardon between his abused cheeks.

"Of course it's me," said Katie, "I programmed her. I mean me."

She thrust into John again just as her twin did the same to his lookalike,

"I wrote the game, John."

John's mind reeled.

"I watched you taking sweet Mary in that gorgeous boy-pussy of yours a number of times!"

Katie's thrusts were sharper now - staccato beats of primal music that John couldn't help dancing to. He moaned in rapture as she slowed, feeding his arse the grinding, twisting length.

"I know all about you and Mary, baby," Katie whispered, "I was there, watching the first time she dressed you up in fishnet and fucked you, just like you're being fucked now. You remember that night, don't you slut?"

John did, and his cock twitched as he recalled that particular violation he'd undergone. His face flushed with shame as he remembered the indecent enjoyment he'd felt when Mary's strapon began vibrating. And as Mary pounded brutally on his arse, he'd felt the first stirrings of a dark addiction as his prostate craved the hard stimulation it was getting.

"Both myself and Mary made a fortune from motion capture, John," breathed Katie, "A foolproof phone app that could map somebody in high-detail 3D from its camera. It wasn't perfect but Mary and I just didn't have the cash to invest, even though it was next-gen stuff. Once we became lovers as well as partners, we, um, found the software worked best if you wore helpful clothing. Such as bright fishnets."

Katie leaned over him, pressing her breasts onto his back. John could feel the hot skin through the layers of fine netting between them. She kept her hips pressed against his, forcing her cock as deep as she could possibly manage.

John's inarticulate cry showed just how much shameful pleasure raced through his body, and his face clenched at his loss of control. Katie started to tease him, grinding a circle against his upturned buttocks and stirring his insides.

John could only gargle a strangulated shriek of indignant glee in response.

"We needed cash and, well, if you want money you make porn. Neither of us wanted to volunteer, but Mary said she'd found just the boy. She'd manipulate him until he'd dress in fishnets and let himself be screwed in the arse good and long - at which point I'd mocap him and we'd walk away with a game.

"Quite an idea, isn't it? A voice-controlled game for femdom sex. There's a dominant mistress running some filthy-minded algorithms to sense what you're doing and give instructions. There's also a submissive sissy slave to service your fancy and obey your dirtiest whim. You can go multiplayer. Or you can hide easter eggs in your code to seize control of the game like I have. So - we had a model sissy, we had the tech, we just needed a mistress to front it. And because Mary had already done the sex part, it was my turn on screen."

John's mind, scrambled by the exhilarating firework display inside his head provided by Katie's cock, suddenly lit up.

"That's me, with improvements. No point keeping any small blemishes, is there? And thanks to one crazy Hollywood divorce that named our game as co-respondent, I've sold enough copies online to fund my own game studio."

It started making sense to John. She knew about his fetish because Mary had set him up. And now they were re-enacting his first fucking (Mary had given him plenty more before she grew bored of him) with Katie reprising her game's role. No wonder she knew the dialogue...

"But studios come and go all the time, John," Katie gasped, her breathing now ragged, "What we need is a hit. What we need is a sequel."

John reeled as the pieces fell into place.

"But you're not... now, are you?"

Katie laughed and tossed her head back as she resumed plunging the toy into John's inviting arse. He felt himself trying to tighten, to stop the rod escaping - and when that didn't work he rocked backwards to meet her motion, squeezing every inch of fullness he could from her.

She laughed again, musically.

"I thought of looking for another model, but what was the point? I already knew a guy who'd do it. Until I could put my plan into motion, so to speak, I'd put up with his constant grooming and primping and preening. Because when the time was right, I'd use his fetish for transvestite pegging to lure him in. This time the slut would fall for himself as bait, his depraved need to watch his own fucking would put him on his knees taking a solid-fucking-girl-cock!"

Katie hammered home the last words with resounding slaps to John's butt, reddening it further and eliciting yelps of humiliation from his bright red lips.

"But people will SEE me!" He gasped.

This time, Katie's laugh was a roar.

"You don't know? We renamed you Sissy, but we didn't change your image in any way - millions of people have already seen you! And millions more will!"

John's shoulders slumped as he took in the full ramifications of his situation, and then collapsed in resigned despair. Could the drilling he was getting make up for the fact he was a crossdressing pornstar? He didn't know - but his arse was the only thing he could concentrate on as he let go of his worries.

"Just think of all those masters and mistresses out there who'd been fucking you silly in all the dirty scenarios my software can dream of for the last year. Pounding you until your little head spins. Millions, wanking themselves off abusing you for their pleasure and amusement. Not to mention those silly, frilly sissy sluts wishing they were you!"

John's body was machine-gunned by splashes of erotic warmth as he thought of the depths of sodomy his avatar must have fallen to, the perversions performed on him around the world. He was a naughty girl receiving initiation into the school's buttslut club from his cousin the head prefect. He was a pathetic, sobbing mess at the hands - and strapon - of a strict aunty with a taste for boys in organza. He was discovered wearing knickers in a nightclub by a predatory-looking hen party which had taken him back to a house for a game of sissy Twister.

Katie's voice knifed through the fantasy haze.

"And now you, John. You're about to orgasm as I fuck you. As you watch your own narcissistic fucking, along with your audience. Give it up for them!"

Katie gripped his throbbing cock with cool fingers.

"Mary's watching and recording the whole thing next-door, but she'll be keen to reacquaint herself with her vain little fuckbitch once we're done."

Her slow but firm strokes on John's cock were slowly driving him towards a tear-inducing orgasm, but she kept her measured pace as she eased her plastic dick into him.

purekink
purekink
582 Followers
12