The Captive Crossdresser Ch. 01

Chapter One -- The Rules

Now

The room was a cell. It had a comfortable queen bed, an ensuite bathroom, a large antique armoire, a sofa with a coffee table and end tables with table lamps on them and a kitchenette.

But it was a cell.

The stark grey door was heavily reinforced and had hidden hinges. It was fitted with a viewing port at eye level, a 'cat-flap' at the bottom and unnervingly, at waist-height, what appeared to be a glory hole. The floor was newly carpeted and the walls were freshly painted cinderblock. There were no windows. There were no light switches for the ceiling fixtures and although the vanity and table lamps had switches and dimmers, power to them was controlled remotely.

At first it seemed like total silence but when he listened carefully Colin could hear the faint hum of running machinery and road noises. There was also the faint swish of the ceiling mounted ventilator for which there was no thermostat or other controls that Colin could find.

The room was spotlessly clean and everything in it appeared new.

Colin Divine had come out of his fugue naked and alone in the big bed. The remnants of last night's gin and tonics burned in his stomach and at first he thought he'd had his usual Friday night binge, staggered home and fallen asleep but there was something else besides alcohol making him drowsy. He'd fallen asleep again and woke up feeling a little better.

The first thing he noticed was that he had gone to bed naked still wearing his makeup and then he noticed that he wasn't in his own home.

He was in the cell.

He sat on the edge of the bed and looked at the rainbow smears of blush, mascara and eyeshadow on the crisp white pillowcase and felt guilty. He saw a red and black, lace-trimmed, nightgown hanging over the bedhead and without anything else to wear he put it on and studied his surroundings.

Colin hammered on the door and called out at the top of his voice until eventually a disembodied voice came through a speaker fitted into the wall next to the door.

"Stop that!" the voice said.

"Fuck you! Let me out!" Colin screamed.

The lights went out leaving Colin in pitch black. Colin had been in dark places before but nothing like this. There was not a single light source and even after waiting fifteen minutes he still couldn't see a thing. He managed to find his way to the small refrigerator in the kitchenette and he opened the door. There was no light. The bulb had been removed.

He tried the dimmer switches for the lamps and bathroom vanity mirror... nothing.

Colin had no way to measure time sitting alone in the dark but he guessed it was three hours before the lights came back on. During that time he had been able to feel his way to the toilet and take a piss and drink water from the tap.

"You fucker!" Colin screamed when the lights came back on and immediately regretted it.

The lights went out and this time it seemed like twice as long before they came back on.

This time when they did he remained silent.

"There are rules," the disembodied voice said through the speaker.

"What rules?" Colin called out.

There was no talk-switch for him to toggle but whoever had Colin imprisoned in the room could obviously hear him. There must be a microphone or microphones secreted in the cell.

"They are on the wall next to the speaker," the voice said emotionlessly.

"Fuck you! Where am I and why am I here?" Colin shouted.

The lights went out.

An eternity later the lights came back on.

"Read the rules," the spectral voice said.

Colin found the rules etched onto a plasticised board mounted on the wall next to the speaker as he'd been told they were.

1. No unnecessary noise

2. Keep my room clean

3. Keep myself clean

4. Do everything my master tells me without question

5. I am to present as Crystal at all times and use my femme voice

"Ok. I read them. Will you please tell me where I am and why I am here?" Colin's stomach lurched when he read the last rule.

How did his captor know about Crystal?

"Go to the bathroom door and read your daily duties," the ghostly voice said with no emotion whatsoever.

1. Shave my body all over every second day

2. Shave my face in the morning and again in the afternoon

3. Douche after shaving, shower, brush my teeth and use mouthwash

4. Apply my makeup and perfume and put on my wig

5. Put on my lingerie

6. Dress as directed

7. I am never to present myself to my master unless dressed enfemme

"You're a fucking looney mate," Colin screamed.

The lights went out.

Then

Colin Divine had been secretly crossdressing for nearly six months now. That wasn't quite right! He'd been crossdressing since he was a teenager but only sporadically and not very well. He was what experienced femme transvestites called a 'hairy panty-wearer': a derogatory term for those who occasionally liked to slip into a pair of knickers, nylon stockings, possibly a satin slip and rarely, poorly-fitting high heels. What was a more accurate a statement was that Colin had been presenting as a convincing, unclockable transvestite for nearly six months now with the help of Mrs Maureen Cashmore.

Colin had been fascinated by lingerie and hosiery for as long as he could remember. Watching his aunt and cousins dressed in their short skirts, seamed nylon stockings and heavy makeup fascinated him. He let his cousins make him play dressup. Colin pretended to complain but he loved it when they made him wear frilly knickers, party dresses and put makeup on his face.

His father had caught him parading around dressed like that in front of his three older female cousins and despite his cries that he been forced to do it, his old man had beaten him senseless and told him that he didn't raise a sissy for a son.

The beating had worked until Colin entered puberty. He supressed the urge to dress like a girl but once those hormones began to rage and his libido kicked in he couldn't help himself. He kept a little collection of knickers, stockings, slips and even a little miniskirt and blouse which he dressed up in when no one was home. He was too sacred to wear makeup because he knew his mother would find out that he'd used her cosmetics and besides which he was no good at it.

He'd dress up and read his mother's glamour magazines, looking at the lingerie models until he needed to relive himself then he's stand in front of the mirror dressed in his finery with his feet squeezed into a pair of his mother's high heels and masturbate. He made sure that only his body was reflected in the mirror he didn't want to see his boy-face.

Colin fumbled his way through puberty into manhood. He liked looking at girls who dressed like girls; he had no time for girls who wore jeans or dressed like tomboys. In the mid 1970's miniskirts and pantyhose were a fashion statement and women flocked to the stores to buy them. For the fashion-conscious woman looking to wear a skirt shorter than stockings were long, pantyhose were the perfect fit. He had a collection of pantyhose and stockings.

Colin was very confused about his sexuality. The girls he looked at excited him but he didn't want to do anything to them sexually. If anything he was jealous and often imagined himself dressed as the girls he was looking at. He wondered what it would be like to be one of those pretty girls who could dress so sensuously and beautifully. To feel those clothes on your body every second of the day. To taste the makeup. To feel the fluttery caress of the hem of your skirt tickling your thigh as you strutted in your high heels. To know that all the boys were looking at you and desiring you.

He would daydream at work, watching the pretty office girls. Wondering what their life must be like. Listening to his colleagues complement the girls to their faces whilst discussing the things they would like to do them sexually behind their backs. In his dreams he was a pretty office girl, strutting around the office in her little black skirt and white blouse and high heels and silky tights knowing that the men wanted and desired her. One of the executives would come to visit the firm and become entranced with her and take her away somewhere exotic where he would pour on her the adoration she deserved.

In his dreams he was the heroine of a stereotypical Mills and Boon novel which his mother loved to read. The storylines were similar but his mother had a whole collection and Colin would read them at night before going to sleep. The heroine of the cheap novels was usually a passive virgin who is submissive to the hero in every way. There was no explicit sex in the bodice-rippers but it was implied that the female protagonist would surrender her virtue to the hero after some climatic event in which he rescued her.

This fantasy served Colin well because he couldn't actually imagine having sexual congress with a man. In his imagination he was adored, caressed and kissed passionately and when the man holding Crystal in his arms progressed beyond innocent foreplay his mind would cloud over. He knew that Crystal was surrendering herself to the handsome hero but he didn't want to think about how.

It wasn't until he was in his early-twenties that Colin was finally financially secure enough to leave home and get his own flat. He felt emancipated. He was not only free from the shackles of his overbearing father and mousy mother, he was free to crossdress. He bought himself an extensive makeup collection and two good quality wigs.

Acquiring the makeup and lingerie had been easy enough. He told the shopgirls in Debenhams that the lingerie and nylons were presents for his girlfriend and the makeup was a gift for a niece. He spread his purchases around so as not to attract too much attention. Acquiring skirts, blouses, dresses and heels was not so easy for a man in those days. There was nothing like the internet and Colin had tried and been disappointed with his attempts to order directly from a catalogue and have his purchases delivered by the Royal Mail.

The garments seldom fitted, were poorly finished and rarely resembled the apparel modelled in the catalogues. The same went for shoes and of the several wigs he had ordered; only two were actually wearable. The problem was that Colin didn't really know his size in female apparel or shoes and just like men's clothing, the advertised size was not a true indication of the fit; one needed to try on the garments before purchasing them.

Mrs Maureen Cashmore came to his salvation.

Mrs Cashmore was the manager of the local Oxfam shop. The shop specialised in selling donated clothing and other items for charitable purposes. Because the racks of clothing were juxtaposed, Colin could browse the men's clothing section whilst secretly eyeing off the women's garments. When the small shop had no more than a few customers inside it, it was possible for Colin to browse the women's aisles and check out the high heels on the shoe racks.

Colin was just too scared to actually purchase anything.

He thought that he could possibly just grab a few items that were probably his size. As the items were so cheap, whatever didn't fit he would just donate back. It was good plan but he didn't have the intestinal fortitude to go through with it.

Then one day when he thought no one was looking, Colin picked up a high heel off the rack and put the sole against the sole of his foot to approximate the size. The shoes were cherry-red patent leather with a four inch heel and he wanted them desperately. His current shoe collection consisted of two pairs of beat up low heels and a pair of sandals.

"I bet they would fit you perfectly," Mrs Cashmore whispered over his shoulder making Colin jump out of his skin.

He dropped the shoe and ambled his way towards the door, his face burning brightly.

Somehow Mrs Cashmore had beaten him to the door and she stood guarding it with her arms crossed against her ample bosom.

He expected that she would call the police. What on earth for he couldn't imagine: was being a crossdresser a crime? Would she call out to the other customers that he was playing with women's shoes in the store? Would she phone his parents and tell them that their son was a deviate?

Colin knew that none of those things were likely or even rational but his mind was in turmoil and he just wanted to get out of the shop but Mrs Cashmore blocked his way.

She put out her hand, which was long-fingered with many rings on her fingers and bracelets on her wrists, her manicured fingernails were bright red. She gripped his wrist and led him aside, just inside the door and whispered in his ear.

"Come back at five o'clock when I'm closing and I'll get you sorted," her breath tickled the side of his face.

Her perfume smelled exotic and her grip, whilst quite firm, was reassuring. Her red hair tickled his face when she leaned into him and although Mrs Cashmore was at least as old as his mother, Colin felt an attraction to her.

"There's a good lad," she let go of his wrist and cheekily spanked his buttock as she propelled him towards the door.

*****

Now

Colin lay on the bed in the total darkness and tried to make sense of his predicament. The last thing he remembered was being in the Black Sheep, a gay and crossdresser friendly pub on Canal Street. Crystal had met up with Wendy and Brittany and they had allowed several men to buy them drinks and during the course of the evening they had become separated which was nothing new. Wendy and Brittany often went their separate ways when they met a man they fancied, leaving Crustal to find her own way home.

Colin's femme name was Crystal... Crystal Divine was a great name for a transvestite or a drag queen Colin thought when he first came up with it.

Crystal was not inclined to go with men nor bring them home. There was no doubt that she felt sexy around men and adored it when men pursued her but she was too scared to do much more than kiss and cuddle. Crystal had fought off a few fumbled attempts at sex in the dark up against the wall down near the canal with men who had been persuasive enough to get her down there but they had been unsuccessful because as soon as they put their hands under her skirt or tried to put her hand inside their trousers she froze.

The only consummated encounter as such had been a boy who had pulled out his penis and rubbed it on her leg while they were kissing. She hadn't even noticed that he had it out until he came all over her best sheers. She'd slapped his face and ran all the way home.

Crystal had not noticed the man who had taken a keen interest her for some time. The man stalked her until he knew her day to day routine. Crystal presented as Colin during the working week and transformed into Crystal on Friday evening after work and remained presenting as Crystal until Monday morning.

On Friday night's Crystal went out to The Black Sheep pub because it was a safe space for her kind. She had befriended Wendy and Brittany, two other passable and pretty crossdressers around the same age. The man had no interest in Wendy or Brittany. Despite or perhaps because of their feminine good looks and overt sexuality they attracted a certain kind of man who admired their type. It came as no surprise to the man to find out that these men were in fact referred to as 'Admirers'.

What the man disliked about Wendy and Brittany was that they were promiscuous. The three 'girls' would gather at the pub and natter whilst gentlemen bought them drinks and asked them to dance, which all three of them did but as the evening drew to a close Wendy and Brittany always left with men and not always the same men. Saturday night was drag queen bingo and Crystal, Wendy and Brittany played and were entertained by the two sassy drag queen hostesses. After bingo it was a sing-along led by the drag queens and a gay guy playing piano. Crystal would go home alone while Wendy and Brittany were picked up by their regulars.

The man had followed Wendy and Brittany to see what they got up to. Wendy lived by herself and took the men back to her flat but Brittany was actually a married man with two children and she usually ended up down by the canal, shagged up against the wall or on an old mattress under a cut-out in the brick wall. One night to his disgust he saw Brittany take on a procession of men one after the other or two at time both anally and orally. He found her repellent.

Crystal was a different fish. She was just as attractive as Wendy and Brittany, probably more so, and had caught the attention of plenty of Admirers but other than a kiss and a cuddle she seemed unable or unwilling to consummate sexual congress. The man listened to the Admirers in The Black Sheep talk about the 'trannies' as they called them; comparing notes. Crystal was considered a 'cock-teaser' and there was a standing bet amongst the men that whoever finally got to shag Crystal would get free drinks for a week from the other Admirers.

Crystal was a perfect fit for what he had planned. The man was indeed an Admirer, but a special kind of Admirer. He wanted a 'tranny' he could keep for his very own; a special woman who he could train to behave just how he wanted her to behave and serve him and only him!

Yes... Crystal was prefect!

Then

Mrs Maureen Cashmore was what Colin's mother referred to as: 'mutton dressed as lamb'. She had to be at least forty-five but she was dressed in a light grey high-waisted A-line skirt which showed a lot of leg, a white rayon long-sleeved frill-necked blouse, patent leather black high heels and tan tights. The jacket that matched the skirt was draped across the back of chair behind the cash register.

Her highlighted tresses were permed in shoulder-length bouncy curls, framing a pretty face enhanced by cat eyeliner, heavy mascara, creamy bright eyeshadow, rouged cheeks and red lipstick. Her costume jewellery was large, sparkly and clunky.

Colin paid attention to all these things because they mattered to his alter-ego Crystal Divine. Crystal liked the suit, shoes and blouse and would dearly love to have the woman's makeup skills. It was the kind of outfit she would like to wear around town on a Saturday afternoon before changing into something a little retro for an evening in the pub... if she ever got the nerve to do so.

Maureen met Colin at the door of the Oxfam at five o'clock as agreed. She ushered him inside and closed the door flipping the sign over to read 'Closed' before leading him over to her desk next to the register where a tea service had been laid out. All of the blinds had been closed and the overhead lighting switched off but enough light to see was projected by the standard lamps dotted around the small store.

The very same pair of cherry-red patent leather high heels with the four inch heels were laid out on the desk.

Colin blushed.

"What's your name sweetheart?" Maureen asked.

"Colin. Err... Colin Divine," Colin stuttered.

"Not that name silly. What is you femme name? What do you call yourself when you are dressed as a woman?" Mrs Cashmore put her hand over Colin's to keep it from trembling.

His face went bright red and he looked away from Maureen Cashmore, unable to meet her gaze.

"Don't be ashamed dear. There's plenty do it and plenty come here to buy their clothes," she patted his hand.

"How... how did you know?" Colin whispered.

"Well darling you have a few little tells; your nervousness around ladies footwear and apparel for starters. You also need to ensure you get all of the nailpolish from under your cuticles and remove the last skerricks of eyeliner from your eyelids. Most wouldn't notice but a practiced observer like myself can see those little signals quite easily," Mrs Cashmore began to pour tea.