The Captive Crossdresser Ch. 02

Brendan had never done anything homo before. Frottage was considered not much more than mutual masturbation which most teenage boys experimented with. Even the rugby footballers at college played 'soggy biscuit' after school in the dressing sheds after they had been drinking.

When Maurice De Witt took Brittany in his arms and kissed her she felt 'right and proper' for the first time in her life. She felt comfortable in her own skin. She felt like she was normal.

They made their way to the couch saying little, Maurice leading the way. Maurice was two years older than Brittany at twenty years of age and was attending university. Unlike Brittany he was no virgin and was accomplished sexually with both men and women.

He took his time seducing Brittany knowing she would be skittish and scared as it was not only her first time coming out as a young woman but also her first intimate encounter, other than a little cock-rubbing in ballet tights.

He kissed her; softly at first and Brittany sighed. She felt wanted, appreciated and desired. He kissed her a little harder and Maurice put his tongue in her mouth and Brittany liked it. She liked being held by this strong young man, she liked the way he held her and caressed her, she liked the way she could feel every article of clothing on her body: her satin knickers caressing her privates, her silky tights encasing her long legs, the hem of her skirt tickling her thighs, her satin blouse cosseting her tender flesh, the taste of her makeup, the smell of her perfume.

She finally felt like a woman.

When Maurice took Brittany's hand in his and guided it to his groin she didn't resist. There was the awkward fumbling that so often occurs when couples are kissing and trying to undress at the same time but eventually she freed his manhood and took it in her hand. It felt warm and sleek and alive and Maurice gasped into her mouth as she softly stroked it.

Brittany quivered with anticipation when Maurice put his hand on her thigh and stroked her nylon-shrouded flesh. He brushed her nylons with the tips of fingers enjoying the feel of her slinky tights. His hand slid under her skirt and Brittany whimpered and shuddered when Maurice fluttered his fingers along her engorged cock through the layers of satin panties and nylon tights. The front panel of her knickers became wet with her secretions and Brittany could feel Maurice smile as he kissed her.

Maurice broke the kiss and leaned back into the sofa and pressed gently on Brittany's head. At first she was confused but then she realised what he wanted and she mustered her resolve and lowered her face into his lap. She took his appendage into her mouth and sucked it like a baby sucks a dummy and Maurice mewed with delight. Brittany's own cock was pressing against her knickers, tenting her skirt and Maurice pushed her skirt up out of the way and stroked her engorged penis through her panties.

Brittany experimented a little and began to move her mouth up and down on Maurice's cock while her tongue flittered on his glans. This caused him to groan and push his groin upward to encourage her so she knew that what she was doing was enjoyable.

She settled into a steady rhythm, suckling Maurice's organ while he stroked her through her saturated knickers. She could taste the precum dribbling from Maurice's trembling organ and assumed that he was about to come; she was close to flooding her knickers too.

Maurice surprised her when he pulled her face out of his groin and quickly stood up. She sat on the couch looking up at him with his long thick cock poking out before him as he quickly stripped. She was becoming a little apprehensive, especially when she saw him take a tube of KY Jelly out of the pocket of his jeans. This was all going a little too fast and she began to protest when Maurice flipped her on her back and jumped on her, lying on top of her with her legs spread wide.

He kissed her passionately and she felt his cock pressing on hers through her knickers and tights. This was familiar territory, frottage, and she wrapped her legs around him and returned his kisses. She would rather have liked to have tasted his semen in her mouth but if Maurice wanted to frot to orgasm she was more than willing. Having this young man on top of her kissing her while he ground his cock against her knickers was very arousing and she felt very feminine, lying on her back with a naked man mounting her.

Maurice was doing something down there and she wasn't sure what. He appeared to be struggling with the KY Jelly. Suddenly she felt him tear open her tights and ease aside the gusset of her knickers and she felt the flesh of his manhood between her buttocks. She could feel that it was slathered with the slippery salve but she had little time to comprehend this because Maurice found her sphincter and pushed his cock inside her.

Maurice covered her mouth with his to stifle her scream.

"Shh darling. It always hurts the first time, just relax," he mumbled into her mouth.

Tears of pain ran down her cheeks as she felt her anus speared by Maurice's cock. It burned and she felt like she had been split open.

"Just relax sweetheart," Maurice tried to comfort her, kissing her softly, stroking her cheeks.

He had about half of his cock inside her tight passage and was trying desperately not to climax, her anus felt like a velvet glove squeezing his phallus and her nyloned legs were scissoring against his bare skin.

Brittany breathed deeply and concentrated on relaxing her sphincter and suddenly something wonderful happened. Little sparkles of delight began to tingle from her tight puckered ring and radiated up her anus where the pressure of Maurice's cock was causing some vague but pleasant sensations that she had never felt before.

All of the pain was gone, replaced by pleasure. She had never felt more womanly, lying on her back with a strong young man on top of her, her legs wrapped around him, her high heels pointing at the ceiling.

Maurice could sense the change in Brittany and was rewarded when she dug her heels in his flanks and encouraged him to fuck her. She gasped when he slid the remainder of his phallus inside her tight anus but it was a sigh of delight, not displeasure. She wrapped her arms around Maurice and held him close as her silky legs caressed his tender flesh.

Maurice fucked Brittany; but not for long. Four long slow strokes were all it took to cause him to ejaculate deep inside her, flooding her anus with his hot seed. Brittany felt his cock quiver inside her and she knew what was happening, then she felt his semen dribbling from her anus as he continued to thrust his cock in and out of her, lighting up the pleasure centres in her sphincter and her prostate.

Brittany soaked her knickers as the most tremendous orgasm washed over her. She clung to Maurice and rose up off the couch driving her buttocks upward, impaling herself on his manhood as it skewered her bowels. She raked her nails on his back and her high heels chafed his flanks as she encouraged him to fuck her.

She held him close as they both rode their orgasms to the zenith and descended into contented bliss.

Later that afternoon they took drinks up to Brittany's bedroom and did it again; this time with Brittany dressed in a basque and seamed nylon stockings. Maurice pushed her down on her bed on her hands and knees and rode her from behind and Brittany loved it but not as much as when he lay on top of her, kissing her.

Having found out that she rather liked being buggered, Brittany started bringing home a select few boys who treated her like a lady should... well a lady of loose morals anyway, while her mother was out.

It all came crashing down when her mother came home unexpectedly one day and found Brittany bent over the living room sofa wearing a tutu, leotard, ballet tights, high heels and wearing full makeup being rogered by her ballet master.

Brendan's ballet career had never taken off but he liked hanging around fit handsome young men who wore tights and had a persuasion for their own gender. After today that door was closed for ever.

"Oh dear. I think we will have to find you your own digs Brendan," his mother sighed as she put her handbag on the table and went to the liquor cabinet.

She used some of her husbands 'guilt money' to buy Brendan a little house in Spring Gardens where Brendan became Brittany whenever the fancy took her. Her two-up two-down wasn't far from the Oxfam shop and she became a frequent customer there and befriended by Mrs Cashmore.

"And that's the story of Brittany," Brittany stubbed out her cigarette in the ashtray and nodded to an attentive Admirer who wanted to buy a round of drinks.

Crystal told Brittany her story, similar in its own way: the compunction to dress femme at an early age, the fascination with feminine things, the need to present as passable as possible but in Crystal's case there was no sexual element yet other than masturbation.

They sat at the table all night drinking and talking, watching the transvestites perform their numbers on stage every so often. A number of Admirers approached them and Crystal was nervous with them all. She sensed that some of them had genuine affection for the attractive crossdressers and some of them made it obvious they were only interested in sex. That first night Crystal didn't dance but Wendy and Brittany did. Wendy seemed to have no problem when the men she danced with felt her up and was openly salacious.

Besides the transvestites there were plenty of gay men sitting in small groups or as couples; some of them openly displaying affection for each other. The gays showed little interest in the transvestites but there seemed to be an alliance between them. This was their turf. This was their safe space. The label 'LGBT' and the other half of the alphabet appropriated by the queer community had not yet been coined.

Crystal learned a lot that night in the Black Sheep pub. At closing time Wendy walked away down towards the canal with two men but Brittany walked Crystal home.

"I have my gentleman friend coming to my place in half an hour. He's staying the night. You'll need to harden up girl because if you're going to keep your virginity, you'll be walking home alone from now on," Brittany leaned in and kissed Crystal on the cheek.

Neither of the women saw the man hiding in the shadows watching them. He had been seated near one of the faux marble columns in the back corner of the lounge at the Black Sheep studiously observing them. Well actually he had been studiously watching Crystal.

Crystal contemplated the evening as she lay in bed sans makeup but still wearing her tights and knickers and a satin chemise. She liked Brittany and despite her bawdy ways Wendy was nice too. She had liked being out in public, she'd liked drinking and listening to the music and would have liked to have got up the courage to dance. She had to admit that she liked the attention of the Admirers as they reaffirmed her femininity and beauty but was put off by some of their lewd behaviour.

She had a standing offer to join Brittany and Wendy at the Black Sheep on Fridays and Saturdays and even if they weren't there she knew that the Black Sheep was a safe space in which she could socialise.

Crystal slept well while the man who had followed her home worked all night in his cellar putting the finishing touches on what was soon to be her cell.

Now

To say the situation was absurd was an enormous understatement. The situation was insane! Crystal Divine had resigned herself to living in a tiny underground two-room apartment where she had a strict regimen that controlled her day. Wake up, exercise, ablutions, put on wig, makeup and lingerie, perform fellatio at the glory hole, dress as directed, have breakfast while her captor read her the newspapers and discussed current affairs, spend the day languishing reading magazines and romance novels, strip, exercise again, ablutions again, don lingerie and makeup, fellate her captor, have dinner sitting at the table near the door talking to her captor well into the evening until it was bedtime.

To say it was bizarre was laughable.

What was bizarre was that Crystal had grown to like it. She thought long and hard about Stockholm Syndrome and the effect of her being held prisoner for so long and the way her captor manipulated her by allowing her to do all the things she enjoyed except for granting her freedom. Crystal had even gown to like the sex. It was the single thing that gave her power over her captor.

When he begged her for release, when he mewled and groaned his appreciation for the pleasure she gave him it empowered her. When he released his seed into her mouth or onto her hand she felt rewarded and she remunerated herself by secretly masturbating afterward or in some cases actually achieving climax along with her captor; flooding her knickers as he flooded her mouth.

Crystal knew it was insane but it had become her version of reality. She often wondered what her captor looked like. She knew he had deep blue eyes and sandy hair and that his arms were muscular and that his voice was deep and rich. Was he so disfigured that she could never see him? Was he keeping his identity secret so that when he released her she would never be able to identify him? Was he an ogre, a beast or monster or was he a prince; her saviour, her champion and protector?

Crystal knew that their relationship was unhealthy and more than likely that she was suffering some form of insanity but she didn't care. Other than refusing her food and light when she had denied him sexual favours or disobeyed the rules he hadn't harmed her. It would be easy enough for him to burst through the door and beat her, to subjugate her, brutalise her or to rape her but he hadn't. He could spike her food and ravage her while she lay unconscious; she knew he had the wherewithal because he had drugged her to take her captive.

Time held no meaning for Crystal. There were only weekdays when her captor worked and weekends when he spent most of his time talking to her through the door and she had to admit she liked his company. She missed Wendy and Brittany and Mrs Cashmore but she had few other friends in the world to pine for, certainly not her parents or her work colleagues. She had bonded with her captor and though she knew it was insane to feel so, she was content.

Her captor told Crystal what he done when she asked about her former life. He told her how he had stopped the rent on her flat, stopped her subscriptions and newspaper and milk deliveries and told both Colin's realtor and employer that he had been called away urgently to Australia to help his brother.

Crystal thought of Colin as another person; he was no longer part of her. He was some far off entity that she had once cared about but was no longer relevant.

"But Colin doesn't have a brother," Crystal said through the door when her captor told her what he had done.

Her captor noticed that Crystal talked about Colin in the third person. He smiled. His psychological manipulation was working.

"Of course he doesn't but they don't know that. Brittany and Wendy were worried about you though," the man taunted her a little.

"They were?" Crystal felt grateful that her friends cared about her disappearance.

"They've accepted the fact that you've purged. Crystal will either reappear in all her magnificence or she will never be seen again. Isn't that what your kind do?" he couldn't help but mock her a little.

Crystal knew all about purging. She had considered it herself on a number of occasions but had never gone through with it. The compulsion to crossdress was too strong. She did note the slightly wicked tone in his voice that he used now and then to reminder that she was his captive.

"Who would have told them that?" Crystal asked.

The man slammed the viewing port shut and didn't return until the next morning.

After his morning blowjob the man put Crystal's breakfast through the cat flap on which was a piece of paper telling her how she was to dress for him after work. This was not an unusual request as the man often wanted her to dress differently in the evening. On some weekends he would ask her to change numerous times, watching her through the viewing port or on his video screen. Sometimes she would tease him. Knowing that he was watching she would perform a slow striptease and take an overly long time putting on her lingerie.

Keeping her back to the door and the camera she would slip into her sexy knickers and then face the screen as she fastened a suspender belt around her waist and pulled the garters through her knickers and ever so slowly slid her stockings up her long legs, smoothing out the wrinkles, straightening the seams; all of her movements exaggerated, her overly made-up face staring at the viewing port or the camera, her red-lipsticked mouth pursed in a sexy pout. She would slip on her heels and parade around the room pretending that she had lost something, an earring perhaps? Bending over often to show her pert creamy buttocks swathed in her nearly transparent knickers to the door or the camera.

If she overexcited her captor he would come to the door and demand sex, throwing open the cover of the glory hole and thrusting his trembling cock through it and Crystal was always happy to oblige him as performing for her captor also excited her and inevitably she'd climax when she fellated him.

As time passed Crystal began to realise that the routines and rituals, the conventions and procedures, the formalities and etiquette that ruled Crystal's life, ruled her captor's life too. The time and effort it must take for him to care for her and to abide by the schedule he had set for her; the determination and discipline that must take was extraordinary. She may be devoted to him but he was equally devoted to her.

Crystal read the man's directive on the sheet of paper once again. She had become used to his handwriting which was an elegant cursive script which fitted her vision of what the man looked like. That evening she was to wear the green satin basque, black fully-fashioned, fifteen denier stockings, black satin panties, black patent leather high heels and the flaming red wig. Over her ensemble she was to wear the transparent black satin and lace negligee.

Very sexy.

When the mood took her, Crystal liked to put on a little show for the man, waiting for him to get home from work before she changed so that he could watch her dress. She would tease him until he became fanatically aroused and ached for her to relieve him. She might provoke him a little when he put his cock through the glory hole. Maybe use some prolonged masturbation techniques until he begged her to use her mouth on him. Then she would tease him with her tongue and lips, using featherlight flickers of the tip of her tongue on his fraenulum and glans while her lips danced loosely along the flesh of his shaft.

She would use her feminine guile to titillate and beguile him until he was fully rampant and ready to surrender his seed, begging for her to bring him to climax. Then she would earnestly suck at his engorged phallus, milking every drop of his semen into her mouth. She would likely climax with him, her cock untouched, her orgasm triggered by her captor's own ultimate bliss.

She was hard inside her knickers at the thought of it and she smiled.

When she heard his footsteps upstairs she retired to her bathroom and prepared herself. She shaved the almost non-existent stubble from her face; her second shave of the day. She brushed her teeth and used mouthwash. She sat on the toilet and evacuated what little she had inside her and then used the bulb douche until the water ran clean. She didn't understand why the man insisted she perform this task but she had long given up questioning him about 'the rules'.