The Captive Crossdresser Ch. 03

Story Info
Crystal's captor wants more sex but she has an escape plan.
12.7k words
4.82
10.5k
7

Part 3 of the 3 part series

Updated 06/11/2023
Created 03/31/2022
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
MicheleNylons
MicheleNylons
3,980 Followers

Chapter Three -- The Emerald Earrings

Then

Crystal lived for the weekends. When Colin finished work each day and took the number ten bus home he would begin transforming in his mind. By the time he arrived home he was already Crystal and he would shuck out of his cheap suit and transform into her, trying different makeup techniques and toying with her wig collection to see which wig complimented her growing wardrobe.

Crystal had stopped buying anything that she thought fitted her on a whim, only to be disappointed when she got the garment home and tried it on and found it was tatty, ill-fitting or did not suit her. Under the tutelage of Mrs Cashmore she selected only those garments that fitted her properly and were befitting.

Crystal was becoming more confident. She was more than happy to walk to and from the Black Sheep public house on Friday and Saturday nights. At first she would only walk in the company of Wendy or Brittany whom she would meet on the corner of her street but after a while she acquired the intestinal fortitude to make the walk on her own.

On Wednesdays after work she would dress hastily at home and make the ten minute walk to the Oxfam Emporium on Oldham Street where she would meet Mrs Cashmore who always had a fresh pot tea ready and sometimes a garment or two to sell to Crystal. Sometimes there was nothing suitable in the store and they would just natter and drink tea.

Mrs Cashmore was very interested in Crystal's progress. Crystal had perfected her walk, her speech and mannerisms and was virtually unclockable. Although Crystal had not yet developed an interest in men sexually, like most of her kind she did like to be admired and appreciated. Mrs Cashmore imparted on her little secrets, such as to always to pay attention to the man talking to her even if he was boring. If she found a man she particularly liked she could use discrete gestures to attract him: lean forward when talking, 'accidentally' touch his knee or elbow, blink a little, play with her hair, subtly lick her lips; all tricks of the trade, as Maureen Cashmore described them.

Crystal would practice the tricks at home and then try them out at the pub on the Admirers that pursued her and Wendy and Brittany.

The three girls made a game of it, seeing who could attract the most men in one night or they'd pick out a handsome man and see who could win him over. If the man chose Brittany or Wendy he would most likely be rewarded carnally. Brittany would probably take him home for the evening and Wendy would take him down the canal. If the man chose Crystal he would be disappointed. He might get to feel her up a little on the dance floor and maybe even get in a kiss or two but Crystal was unresponsive to sexual advances, hence the standing bet amongst the Admirers to see who would be the first to get into her knickers.

The men who were disappointed when Crystal eschewed their carnal advances easily found a willing substitute amongst the gaggle of transvestites who colonised the Black Sheep and other tranny-friendly venues near Canal Street so Crystal didn't really think of herself as being a prick teaser; she made it very clear that she had no interest in sexual congress.

All of this was witnessed by the handsome mid-thirties man who sat brooding on a stool in a corner of the lounge bar at the Black Sheep well away from the other patrons where he could observe the passing parade and the interactions of the boisterous masses. On Fridays he sat sullenly and observed the Admirers fawn over the pretty and not-so-pretty transvestites. He abhorred the way the Admirers grovelled and toadied up to the crossdressers. Buying them drinks, pawing at them, fumbling at their legs under the table, squeezing their arses on the dance floor.

On Saturdays when it was drag queen bingo he would purchase a single bingo card and leave it unmarked. The bingo numbers were called out by three overly feminised and sexualised drag queens. The game merged bingo into a live drag cabaret performance with the drag queens treating the punters to a risqué comedy show whilst involving them in the bingo game.

The man did not participate at all and sat sullenly at the bar during the bingo and the sing-along that followed.

The man had collar-length sandy hair which he continually flicked out of his deep blue eyes. He was tall and his body was trim and muscular. Unlike most Mancunians he was tanned. He exercised daily and ran along the canal and visited a tanning salon once a week to keep himself bronzed and went to Spain twice a year to lie on the beach.

He was handsome and he knew it but he had little interest in the type of women that were attracted to him. All his attention was focused on one particular woman... only she wasn't really a woman. Her name was Crystal Divine.

The man owned a successful antiques store on the high street, dealing in high-end merchandise but he also sold good quality second-hand furniture to keep the profit ticking over. He was a picker and would frequent rummage sales searching for suitable castoffs and he also scoured the many charity shops scattered throughout Manchester.

It was there that he found the materials and furnishings to renovate his cellar. At first the idea of keeping a specially selected girl captive in such a place was just a fancy; a daydream, a fantasy but when he saw Crystal he began to plan his cunning scheme.

The man had always been an Admirer of feminine transvestites; the more passable the more he found them attractive. There was something about the way they paid attention to every detail of their countenance. Their hair and makeup was perfect, their clothing stylish and often alluring, they always wore nylons, often stockings sometimes tights, and high heels were de rigueur. He was not a fan of boots or platforms; he was a stiletto heel aficionado.

Some of the crossdressers who inhabited the Black Sheep met his high standards but most of them let him down with their loose morals. His fantasy was fuelled by thoughts of having one of those beautiful special ladies for his very own; to kiss him, to snuggle up to him, to gratify him sexually, to be devoted to him and to love him. He would love her in return.

It was a preposterous idea and he knew it but he could dream. The girls down on Canal Street who fuelled his fantasy had a particular weakness he found abhorrent: they had loose morals. He saw how they behaved in the pubs and clubs and he saw what they got up to in parked cars, doss houses and up against the wall down by the canal. No wonder the coppers were hell-bent on locking them up, they were whores being passed from man to man.

But all that changed when the man saw Crystal and he began to stalk her. She was young, beautiful, alluring, a bit of tease yes but she was chaste. He saw the look of disdain on her face when men groped her and her contempt for the crossdressers whose morals were loose. She tolerated Wendy and Brittany licentiousness because they were her friends.

The man knew where Crystal lived, the route she walked to and from the Black Sheep, her weekly visits to the Oxfam Emporium. He knew about Colin, where he worked, how little he socialised how he spent all of his spare time as Crystal, adopting her persona every chance he got.

One night after the Black Sheep closed and the throng was dispersing the man was watching Crystal more intently than he ever had before. She had drunk more than she usually did and was behaving a little gregariously. A handsome young man named Dennis Hadley had sat at Crystal's table, wedging himself in beside her, chatting to her and buying her drinks. Brittany and Wendy had hooked a couple of their regular Admirers and were encouraging Crystal to let her hair down.

Dennis was more a boy than a man, probably in his early twenties but he was handsome and confident and was an accomplished conversationalist. He'd even talked Crystal into getting up for a dance, holding her close during the slow numbers, taking his time but eventually putting a hand on her arse and gently squeezing it. Dennis nuzzled her neck, then her cheek and finally stole a kiss.

The man was fuming. He wanted to rip Crystal out of the Dennis's embrace and thrash the young upstart and then punish Crystal for her lewdness.

Crystal knew that she had drunk too many Gin and Britvic bitter lemons but the boy was handsome, he had the gift of the gab and he showed her admiration and respect. When Dennis had taken a few liberties on the dance floor she hadn't minded too much. She had allowed Dennis to kiss her and she quite liked it. She liked his attentiveness. Besides she would send him home disappointed just like she had all the other men who had shown an interest in her that way.

But she had drunk even more and at closing time found herself on the street with Wendy and her beau. Brittany had let her gentleman friend walk her home. Dennis had his arm around Crystal's waist as much to keep her on her feet as to cuddle her.

"Come on down the canal Crystal; you're too pissed to walk home and you won't get a cab at this time of night," Wendy squawked.

Crystal knew that Wendy was right, she couldn't walk home in this condition and there was no way she was letting this boy walk her home; he would know where she lived if she did. She reluctantly acquiesced to go down to the canal and she could sense the perception of victory and eagerness in the young lad who was keeping her on her feet.

The man followed them, staying in the shadows, his heart in his mouth. He knew where they were going and what was likely to happen. If Crystal surrendered her virtue he would be bitterly disappointed and would have to begin his search all over again. He had only just finished remodelling the basement, mounting the specially constructed the door, putting in the security camera. His adoration for Crystal was being severely tested.

Crystal allowed herself to be led along Chorlton Street and down the slippery stone steps to the towpath that ran alongside the canal. She and Dennis stopped frequently to kiss and cuddle which Crystal endured because she could hardly stand on her own two feet. Wendy and her chap, a besuited man in his forties, also stopped to canoodle, the man squeezing her buttocks and slipping a hand under her skirt which Wendy didn't seem to mind at all.

The man treaded carefully down the steps behind them, waiting for the foursome to dawdle along the towpath before he crept along behind them hugging the wall.

They passed men ensconced in passionate embraces hiding in the gloom and young rent boys on their knees servicing punters who had parked in the nearby Bloom Street car park. In a cut-out cloister in the brick wall running along the towpath a tranny was bent over a crate, her skirt hitched up and her knickers around her ankles as a fat man wearing work clothes and a flatcap buggered her.

Wendy and her chap laughed raucously and Crystal tittered nervously; she found the spectacle distasteful. Dennis nuzzled her neck and nipped her ear which, although not unpleasant, didn't seem an appropriate response for where they were and what they had just witnessed.

The man was trailing behind the foursome, sidled up to wall so as not to be obvious. When he passed the cloister the tranny was sitting on the crate pulling up her knickers, her suitor had passed the man, heading furtively but quickly back to the Bloom Street car park.

The tranny paused, her knickers not quite hitched up all the way.

"You wanna go luv? Tenner for a shag and a fiver for a blowie," she grinned at him, her lipstick smeared around her mouth and her wig slightly askew.

The man shivered with revulsion and moved on.

"Here's my spot," Wendy pulled her chap into a deep cloister.

The bricked archway was gloomy but a streetlight across the canal cast enough yellow light into the cut-out to see well enough.

There was an old mattress on the ground in the corner with a threadbare comforter on top. Crystal did not want to think of what kind of vermin might have called the cloister home nor what bodily fluids had been absorbed by the mattress and comforter over the time it had been here.

There were empty beer cans and pop bottles, cigarette butts and decaying condoms scattered on the damp cobbled floor.

Crystal was starting to sober up and regretted her decision to follow Wendy and her chap down to the canal and to allow this young man to accompany her.

"Come on luv," Wendy giggled and pulled her chap down onto the mattress.

Dennis pressed Crystal against the wall and tried to kiss her. She resisted his advances at first, moving her face away from his and wriggling her body, trying to break free of his embrace. The young man was becoming angry and she could understand why. Hadn't she come willingly to this den of debauchery? What did she expect would happen?

Crystal stopped struggling. She'd let Dennis have a kiss and a cuddle and then she would get him to accompany her back to civilisation and they would part ways and she would walk home.

Dennis realised that his anger was upsetting Crystal so he stopped being aggressive and held her gently in his arms. He pressed his lips to hers and she let him kiss her.

He was pretty good. His lips firm but not crushing, his body pressed against her but not overly frenetic, his arms were around her and he stroked her tenderly. Despite the surroundings, Crystal actually felt quite womanly and appreciated.

The man had stopped at the archway and pressed his back against the brickwork facing the canal.

"Fucking bitch!" he hissed quietly.

He turned to face the wall and peeked into the cloister and saw Wendy on the filthy mattress with her chap on top of her kissing her. He'd hiked up her red velvet miniskirt and was in the process of trying to pull down her knickers and tights as Wendy wriggled and giggled underneath him, encouraging him.

Crystal was pinned against the wall by the young man who held her in his arms and was kissing her. Her eyes were closed and she appeared to be enjoying being kissed, although her hands rested chastely on the boy's shoulders; there was no real carnality unlike Wendy who had her legs wrapped around her beau and was helping him steer his erect penis between her pale plump buttocks.

Dennis slipped his had under Crystal's black leather skirt and stroked her thighs. She clamped them shut and tried to remove his hand. The boy was hot and she could feel that he was tumescent. He pushed his groin into her and she could feel the protuberance through his jeans rubbing on her body.

"Ok Dennis that's enough. Take me back to Piccadilly Gardens and I'll walk home from there," Crystal tried to break the embrace.

"Your friend knows what it's all about. What about it love?" the boy's nature had changed.

He was no longer an attentive suitor, he was becoming quiet aggressive.

Dennis forced his lips on Crystal's mouth and pawed at her thighs and she began to struggle.

"Don't be like that. Isn't this what your type want? Some nice bloke to tell you how pretty you are before he bends you over and shags you up the arse," Dennis hissed as he struggled with the pretty transvestite.

He could already see himself coming into the Black Sheep the next night victorious, telling everyone that he had shagged the prick-tease transvestite, drinking free beer all night having won the bet. Besides which Crystal was very attractive and had a pretty face, great legs and a nice arse and he fancied putting it to her.

Dennis went back to work forcing his kisses on her, stroking her thighs.

Crystal no longer enjoyed being kissed by Dennis. He might be handsome and athletic but he was being unduly rough with her. He thrust his tongue into her mouth, pinning her against the brickwork, his hand under her skirt pulling at her tights and knickers.

"Stop it!" Crystal tried to push the boy away but he was too strong.

Dennis was fumbling around between her legs and Crystal was getting quite frustrated with the young man's insistence.

The man who had followed Crystal peeked into the cut-out and saw Crystal pinned against the wall by the handsome young man. Jealousy coursed through him and he became enraged but then he realised that Crystal was trying to fight the young lad off. He considered leaping into the cloister and rescuing Crystal and giving the young man a thrashing but he would give himself away. But he couldn't just stand here and watch the young ruffian defile the object of his desire against her will.

Then he saw a light down the end of the towpath. It was very bright and was being shone against the brick wall and into the cut-outs and underpasses illuminating men in the throes of carnal exploits. When the light exposed them the men ran away down the towpath and up the first flight of steps they came to. The man looked up the slick, mossy brickwork and saw a flicker of blue light reflected off the nearby buildings. He ran up the steps and saw a police panda car and a black maria with its doors open near the top of the steps. The wooden-tops were herding the men into the paddy wagon as they emerged from the towpath.

Crystal had just about given up fighting Dennis. He was kissing her passionately and she let him. It wasn't really that unpleasant but she just wished she wasn't in this filthy viaduct underpass. Dennis had stopped pawing at her and was content to press his body against hers and Crystal let him. She wished Wendy would hurry up and finish with her friend so they could leave. She glanced over and saw Wendy lying on her back on the filthy mattress, the man on top of her with his trousers down, rutting away at her plump arse, her nyloned legs wrapped around him. They were both grunting and groaning.

She tore her eyes away from the carnality and suddenly became aware of something hot and hard was pressing on her leg. Dennis was humping her thighs. He kissed her harder, pressing her against the brick wall so hard that she couldn't move. She felt a scalding wetness erupt on her right thigh and realised that the boy had climaxed on her leg, rubbing his hard cock on her best sheers.

Dennis shuddered and moaned as he orgasmed and Crystal was able to push him off her and she slapped his face but Dennis just laughed.

"Don't come on like that you slag; you wanted it, otherwise why would you have come down the canal with me," Dennis snarled as he put away his shrinking hardon and zipped up his jeans.

It was then that a bobby on a bike stopped at the entrance to the cut-out and shined a torch into it, illuminating the tableaux of Wendy being shagged on the mattress by the man in the suit and Crystal with her skirt up wiping semen off her nylons.

"You're all nicked!" the copper yelled out.

Dennis bolted out the cut-out and ran for the stairs. The besuited suitor climbed off Wendy and ran after him, trying to button his trousers as he stumbled after the boy. Wendy sprang off the mattress and pulled up her knickers and tights with a speed that was surprising given her chubby physique.

Crystal was still dumbfounded but then she realised what was happening. The bobby had cycled on down the towpath but it was obvious that he had colleagues close by; Crystal could hear the clatter above her as the miscreants were rounded up.

She bolted out of the cut-out as best she could on her high heels and was about to follow Wendy up the steps when a hand reached out and grabbed her upper arm.

"Not that way! Go back down the towpath the way you came and take the steps that lead up to Chorlton Street. Go straight home and don't look back," the man whispered harshly in her ear and pushed her down the towpath back the way she had come.

The man was right, whoever he was; she never really saw his face in the dark and the confusion. It was the longer way back to the streets of Manchester but there were no coppers that way. Crystal looked around to see if she could see the man who had saved her from an embarrassing incarceration but he was gone.

MicheleNylons
MicheleNylons
3,980 Followers