The Captive Crossdresser Ch. 03

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

The man stuffed his hands in his pockets and walked off the other way, ignored by the coppers who were busy rounding up the rent boys, their punters and the odd tranny or two.

When Crystal got home she locked the door behind her and collapsed on the couch and realised how lucky and how stupid she had been. She could have suffered the humiliation of being locked up in the watch house still dressed in drag. When she had regained her composure she staggered off to the bedroom, no longer drunk but suffering from shock. Then she remembered that Dennis had splooged on her best sheers and she lifted her skirt and looked at the large silvery stain on her right thigh. She shucked out of her skirt and rolled down her nylons and tossed them aside.

Too exhausted to do much more she pulled off her wig and fell onto the bed.

Later that night she awoke and felt around the bed until she found the nylons she had been wearing.

She fingered the wet patch and put it to her nose and sniffed the musky scent of Dennis's semen. She wrapped the other leg of the nylon around her turgid member and stroked herself to climax, inhaling the heady scent of Dennis's cum. She felt ashamed for doing so but not for long. She soon fell asleep and dreamt of her Prince Charming rescuing her from some villainous cretin.

The next evening at the Black Sheep the talk was all about the roundup down at the canal. Crystal had to endure a lecture from Brittany about how stupid she had been to go down there with the young man. Wendy wasn't there because she had spent the night in the watchhouse and had been bailed by Brittany on Saturday morning and was currently trying to justify to his wife why he hadn't come home.

There was no sign of Dennis and Crystal was glad. She blushed when she remembered what she done with her semen-soaked nylons alone her bed the night before.

"Two fat ladies eighty-eight," the drag queen on the stage called out, starting the first bingo game.

"Two little ducks, twenty two," her partner called out and the audience dutifully replied 'quack, quack'.

Crystal was saved from further lecturing by Brittany and she marked her bingo card. She wondered who the stranger was who had come to her rescue and guided her on the right path away from the police roundup.

The man sat in his usual corner watching her. He had finished the room in his cellar. It was time to make Crystal his captive before she did anything more stupid than she had last night.

Kidnapping Crystal had turned out to be remarkably easier than he thought it would be.

On the night he had set aside to kidnap her he was sitting at the crowed bar at the Black Sheep when they called last drinks and one of the Admirers sitting with Crystal, Brittany and Wendy came to the bar and ordered a final round. The barman searched underneath the bar for a tray for the Admirer to put the drinks on and the Admirer spotted a tray on a recently vacated table and went to get it leaving the drinks unattended for the few seconds the man needed to put the toxin in the only Gin and Britvic bitter lemon on the bar.

Wendy had not learned her lesson and went with an Admirer down towards the canal and Brittany had one of her regulars walk her home. Crystal parted company with Brittany and her beau at Piccadilly Gardens and by then she was feeling the effects of the potion the man had slipped in her drink. At first Crystal just thought she had drunk too many gins and the fresh air was taking its toll on her but soon she felt disoriented and very confused.

The man swept in and helped Crystal who by this time was finding it difficult to stay on her feet and had no idea what was happening. He helped her all the way to his house on Cooper Street. Anybody watching them at this late hour would think that the man was helping his inebriated girlfriend home.

Once he had her safely inside the house he took Crystal down to the cellar and put her to bed in her cell.

Now

That had all taken place so long ago that she couldn't recall exactly how long ago it was. She had been incarcerated for so long that time didn't really matter to her any longer. Crystal could only lie on the bed and look at the open door. How long had she been held captive? She didn't know, but this was the first time she had ever seen the door to her cell open. It mesmerised her.

Then Crystal turned her attention to the man standing behind the nicely set table. He was vaguely familiar. Had she seen him in the Black Sheep?

The first thing she noticed was that the man was handsome she had to admit begrudgingly. He was older than her but not much; early thirties? He was tanned and fit. She could confirm this because the man was wearing a mulberry silk bathrobe which showed off his bronze muscular chest and well-developed legs. His feet were shod in expensive leather sandals.

"You drugged me again," Crystal said churlishly, making no effort to get off her bed.

She pulled her black satin and lace negligee tightly around her in a vain display of modesty.

The man smiled appreciatively.

"Only a little bit, just to make you sleepy. I wanted this to a surprise," the man indicated the dinner service.

"I've seen you before haven't I? At the Black Sheep?" Crystal tried to recall where she had seen the man before.

The man flicked his sandy hair out of his eyes and studied her; his deep blue eyes sparkled with amusement.

"The Black Sheep yes... and on the canal towpath," the man was incredibly handsome when he smiled.

"It was you! You saved me... when the coppers were raiding the cut-out arches under the towpath wall: Cyril's wooden-tops on bicycles scaring the poofters out of the cloisters and the coppers at the top of the stairs arresting them and putting them in the paddy wagon. You sent me the other way so I wasn't rounded up," Crystal realised who the man was now.

"Your fat friend wasn't so lucky," the man chuckled.

Crystal bristled. She didn't like his tone.

"Wendy is pleasantly plump, not fat, and it isn't funny that she got locked up," Crystal barked at him.

"Ok. Keep yer knickers on. I didn't mean to insult your friend. The other one, Brittany, now she's a sort," the man took a pristine white napkin and flicked it open.

Crystal could not believe that she was feeling jealous of Brittany.

"If you fancied her so much, why didn't you kidnap her instead of me?" Crystal hissed at the man.

"Because she has no virtue. She takes men home to her place. Lots of men," the man held the napkin out to Crystal who reluctantly arose from the bed.

"You know a lot about us," Crystal approached the table wearily.

"I know a lot about you," the man pulled out a chair for her.

Crystal sat down and the man laid the napkin in her lap.

The man wanted to grab Crystal. To kiss her and to hold her close to him. To throw her on the bed and lie on top of her and do things to her. Do all the things he had dreamed of doing to her but that would spoil the months of hard work that he put in. He cleared his mind of the fantasy and began to serve.

"You say Brittany has no virtue. This from the man who pokes his cock through a glory hole twice a day and demands that I suck it!" Crystal barked.

"You didn't like it at first but you got used to it and now you like it," the man smiled cheekily at her as he spooned greens onto her plate.

Crystal blushed deep crimson.

"You said it yourself Crystal, I know a lot about you. I know everything about you," the man used tongs to place a warm bread roll on Crystal's side plate and then he plated his own dinner.

The aroma of the food was making Crystal salivate but she didn't want to appear overly eager.

"It's coq au vin with roasted new potatoes, green beans and asparagus," the man waved at her plate.

Sitting across from her captor with a dinner service between them and good food and wine on the table was the most bizarre thing that had happened to Crystal since she had been captured... but why didn't it seem that way? Because the man was insane? She didn't think so. He wasn't insane. He was infatuated with her, besotted with her, bewitched by her, possessed by her and now he possessed her.

Crystal couldn't help but stare at the open door only a few feet away. She was intrigued by it.

"You can go out through the door if you want to," the man poured them both wine.

"Is this drugged too," Crystal said snarkily and pointed to her glass.

"No my sweet and I promise I will never drug you again," the man smiled at her.

"Now I think it's time I properly introduced myself. I'm Alex Prince," the man hung out his glass like he was offering a toast.

"Of course you are," Crystal nearly choked at the irony.

Crystal picked up her own glass and let him clink the glasses together.

"Alex Prince. Now I have a name to give the police when I get out of here," Crystal said mockingly.

"Really Crystal? And do you think they will believe you? That you were held prisoner in my cellar conversion which I am currently advertising as available for rent? That I force upon you a regime whereby you live full time as the beautiful woman that you are but which I'm sure the Manchester constabulary will find abhorrent? That you give me sexual favours through a specially made portal which will have been replaced by a normal wooden door by the time the plods get here," Alex buttered his roll while he was talking.

"As for Colin Divine, he told his employers and his landlord that he was going to visit a non-existent brother in Australia. When you turn up at the Manchester police station dressed in your finery I'm sure they will be very accommodating and find your story very believable," Alex smiled wanly at her, mocking her.

Crystal picked up her own roll and began to butter it.

"You called my bluff. Of course I can't go to the coppers and anyway it's not them I'm worried about. It's the papers. The British tabloids would have a field day with my story and they'd never leave me alone. I'll have to think of some other way to wreak my revenge," Crystal daintily popped a piece of buttered bread into her mouth and smiled at Alex.

"Shall we dine?" Alex raised his glass and Crystal clinked the lip of her glass against his and took a sip of the very good burgundy.

"So now that you have shown yourself to me; why don't you tell me about yourself?" Crystal said as she cut into the tender chicken.

"It's not a nice story I'm afraid," Alex said; his voice a half-whisper.

Alex Prince told Crystal his life story.

Then

Alex Prince wasn't sure at what age he realised that his mother was a tom; he supposed he'd always known. Knocked up young by a soldier who told her loved her and then abandoned her when he found out she was pregnant, thrown out onto the streets by her parents, what chance did his mother have?

All Silvia Prince had were her looks and her body. Despite the advice from Child Services and almost everyone she knew Silvia decided to keep her baby. It wasn't much of a life for Alex being dragged around from doss house to doss house, brothel to brothel, bedsit to bedsit. Silvia insisted that Alex go to school and she did her best to keep him away from the seedy part of her life and the men she brought home or came to visit.

For Alex, a handsome, intelligent boy, school was rough. The other students knew that his mother was a prostitute and they teased him relentlessly until he became big enough to fend for himself and took up sports including boxing. After beating the school bully nearly unconscious he was left alone by the others.

He grew up lonely and angry; his only real friends were his mother's fellow prostitutes. Street walkers, brothel queens, callgirls and escorts where his surrogate family. Some of them looked after him while his mother worked or had to go to hospital for reasons he was never told. He tolerated them but he found no real love there, except for Miriam Tuttle.

Miriam was different from the other women but Alex didn't know why. She was always dressed nice, a little racy of course because she had to advertise her profession; she was always dressed in short skirts, blouses, nylon stockings, heels and full makeup; Alex could never recall seeing Miriam sitting around in a tattered housedress or nightie like the other women.

Miriam's voice was deep, dark and exotic and she showed Alex genuine affection; nothing sexual, she was just kind, considerate and loving towards him and bought him little presents and looked after Alex as his mother's health declined and her dependence on drugs and alcohol began to spiral out of control.

Alex was taken away from his mother by Child Services and went to live with his aunt who reared him into adulthood. His aunt was an antique aficionado and Alex was good with his hands. He was taking woodwork classes at school and showed an interest in furniture restoration and carpentry. His aunt fostered his interests and introduced him into the world of fine furniture. When he left school she found him a job working part time for an antique merchant while he undertook an apprenticeship in carpentry.

His aunt was a flamboyant buxom woman who was always well-dressed and accessorised. She was like the antiques she sold from the little shed out back of her house: garish and gaudy and a little patched up, except in her case it was makeup and tight-fitting skirts, rather than wood-filler and varnish.

It came as no surprise to Alex when his mother finally succumbed to her vices and the now strapping eighteen year old young man attended her funeral alone; his aunt refused to attend.

It was a small affair and afterwards a few of his mother's acquaintances went down to the pub to drink to her memory. Miriam Tuttle was there dressed nicely in a dark skirt-suit, sheer black nylon stockings and very high heels. Her makeup was heavy but flawless and her blonde hair was coiffed in a fringed bouffant.

Alex drank too much and Miriam took him back to her bedsit. She went to the little stove to make coffee when Alex came up behind her and pressed himself to her.

"Alex, you are just grieving for your mother, you shouldn't be doing this," she said, her back to him, the heat of his erection pressing into her buttocks.

"You were always there for me Miriam. You always cared for me but I've always fancied you I think," Alex sniffed her hair; she smelled divine.

"Don't be silly Alex," Miriam tried to make light of the situation as she spooned instant coffee into two cups.

"You were different from the others; you really cared for me," Alex nuzzled Miriam's cheek.

"I'm too old for you Alex and I'm not your type. You should be chasing young go-go dancers or some nice girl you met in Technical College," Miriam said.

Alex was strong and he spun Miriam around so that she was facing him. He looked into her pretty face which was beginning to age and showing the signs of years working as a prostitute. He wanted to kiss those plump lipsticked lips as he gazed into her hazel eyes, enhanced by too much mascara, eyeliner and eyeshadow.

"Alex you know we shouldn't. You know I'm not like the other girls," Miriam whispered as Alex pressed his mouth to her hers.

He held her close and guided her across the small room to the rickety bed where he eased her down on the rumpled bedclothes. On the little nightstand beside her cigarettes and ashtray were the tools of her trade: condoms, lubricants, stimulants and a vibrator. He ignored them and lay on top of Miriam and kissed her passionately, pressing his cock into her belly.

She lay underneath him, mostly passive; letting him have his way with her. Anything to console him.

He shucked out of his suit and shirt and kicked off his shoes, leaving on his socks and underpants like so many of her punters. He mounted her again and hiked up her skirt and rubbed his cock on her stockings. She could feel the warmth and sturdiness of his throbbing appendage and she reached down and softly stroked it. He gasped in her mouth around his fervent kisses.

Alex put his hands inside Miriam's jacket and squeezed her breasts through her blouse. They felt different, not quite right and he abandoned his assault on her bosom and put his hands between her legs. Her knickers were silky and lacy and he moved his cock from her thighs and rubbed it on the front of her knickers, enjoying the feel of the slippery satin on his engorged member.

Alex had only had sex on two previous occasions, up against the wall in the alley next to his local pub with girls of dubious morals but he had a rudimentary idea of what he was supposed to do.

He slipped his cock into the leg-hole of Miriam's knickers intending to spear her cunt with his hard cock. It puzzled him that he couldn't find the entrance. Where was her fleshy labia like the other girls he had shagged?

"Silly boy," Miriam sniggered.

She reached out for the lubricant on the nightstand and smeared a dollop on his rampant member. In his drunken haze he figured that Miriam must be dry down there from all the fucking she did. It felt wonderful when she took his glistening organ and guided it to her opening. She had put two pillows under her back and lifted her buttocks for him. She still had her knickers on; in fact she was still fully-clothed, which Alex didn't mind at all. He liked the feel of her clothing on his body especially her stocking and knickers.

He slipped inside of her and she was tight. Miriam wrapped her legs around his waist and encouraged Alex to fuck her, kissing him passionately with her arms around his neck. Alex knew that something wasn't quite right but right now it didn't matter, he was in heavenly bliss fucking this beautiful but jaded older woman, feeling her nyloned legs scissoring on his tender flesh, her lips pressed to his and her tongue in his mouth.

Miriam reached down into her knickers and did something and it was only then that Alex realised that she had just freed her cock and balls from between her legs. Now he knew what was so different about Miriam Tuttle but right now he didn't care, he was about to come and he thrust his cock deep inside her anus and spent himself, kissing her roughly, hammering his cock into her. He felt a warm stickiness on his belly and realised that Miriam had come in her knickers, the stench of musky semen filled the room.

Alex wanted to climb off this impostor and punch her whilst at the same time he felt a deep loving affection for her and the opposing sentiments were causing him grave anguish but did not prevent him from enjoying the orgasm that washed over him as Miriam held him tight and kissed him deeply, locking her legs around his waist.

When he had finished with her, Alex climbed off Miriam unable to look at her. He'd seen the tip of her penis poking above the waistband of her knickers and the wet patch on the front panel of her knickers where she had ejaculated. Some of her issue was on his belly and he frantically wiped it off with a tea towel and threw it at her.

"You're an impostor. All these years I thought you were a woman and you were... were... were a freak!" Alex spat at her.

Miriam was curled up on the bed crying, her back turned to him.

"I thought you knew! I was sure Silvia had told you... had explained it to you," Miriam spoke softly to the wall.

Alex hurriedly dressed.

"Tranny cunt!" he hissed at her as he slammed the door and ran down the stairs.

Alex completed his apprenticeship and went on to open his own antique shop and restoration service helped out by a loan from his aunt who kept an eye out for bargains for him to purchase and restore. He retained his interest in sports and fitness and kept himself healthy and tanned, taking holidays to sunny destinations when he could afford it.

The anguish and torment that he felt about the incident with Miriam Tuttle affected him deeply. He developed a love-hate relationship with transvestites. He found himself unable to perform with cisgender women but fascinated by transvestites but only those who were passable and attractive. He loathed them and he craved for them. He hated their promiscuousness but loved their femininity.