The Captive Crossdresser Ch. 02

Crystal and Wendy asked Maureen Cashmore if she had seen Crystal and she said she hadn't and agreed with them that Crystal was likely purging. Many of her crossdressing customers purged and when they once again began to crossdress, Oxfam reaped the rewards as they went about rebuilding their wardrobes. Mrs Cashmore explained to her protégés that many crossdressers might go through years or decades of binging and purging cycles. The purging was brought on by various feelings including fear and stress about the possibility of getting caught while crossdressed, shame and self-loathing, and wanting to please other people. The purging cycle only stopped when the male-to-female crossdresser was courageous enough to accept himself or herself for who they are. The crossdresser was then willing to accept that crossdressing was a part of his nature, whether he continued to view himself as a man, or now viewed herself as a woman.

Wendy had purged many times. Being a married man he lived in fear of being caught but the compulsion to crossdress would not be denied. The term gender dysphoria had not yet been coined but it was a label that suited the condition that many crossdressers suffered from at the time.

After the third day after the demand for oral sex had been issued Crystal submitted and was waiting at the door on her knees when the man poked his erect organ through the glory hole.

She had seen Wendy Doesit fellate men down by the canal and it didn't seem to be much of a chore; she seemed to enjoy it. Crystal wasn't so sure she would. Masturbating a man was one thing. It was something one did for oneself so it was not anathema. Crystal actually felt quite powerful when she performed the act; she was in control. But putting a penis in her mouth was something completely different. It was so corporeal and intimate; it was the ultimate act of submission. But what else could she do?

The man gasped as Crystal reached out and grasped his turgid member. She studied the appendage, feeling its girth, tracing the veins with a long red-lacquered fingernail. She traced the outline of his fraenulum and was rewarded when he shuddered with lust. She circled his glans with a finger and kneaded a globule of translucent pre-ejaculate which she brought to her mouth and tasted.

It was watery, odourless and tasteless but she knew that his semen wouldn't be. It would be viscous and pungent. She shuddered at the thought of having it in her mouth but she resigned herself and leaned forward and opened wide.

She closed her lips over the man's penis, taking about half of it in her mouth. There was no odour or vile taste as she might have expected; she knew the man kept himself scrupulously clean. She'd smelled his deodorant and aftershave through the door and smelled the bodywash on his penis, which is what she tasted as her tongue tentatively lapped at the organ.

The man resisted the urge to push his cock further into Crystal's mouth. He didn't want to frighten her or cause her discomfort. It was frustrating feeling her lips clamped around the shaft of his penis and her tongue licking his rod rather than his sensitive glans. But it was also exquisite watching this young virgin perform fellatio for the very first time. Her clumsy efforts were exciting as the man looked down at the top of her head through the viewing port and saw her suckling his cock, on her knees, subservient and passively compliant.

He bucked his hips a little to encourage her and Crystal comprehended the man's needs and began to move her lips back and forth along the shaft and as a consequence her tongue lapped at his fraenulum and his glans.

When the man felt Crystal's lips slide along his shaft and her tongue lash at the tender erogenous base of his glans he fought to hold back his release but failed. He held onto the doorframe to support his weight as his knees buckled with the intensity of his orgasm.

Crystal was not prepared for the flood of hot viscous fluid that filled her mouth. Her first instinct was to spit out the man's penis and to expel his musky issue but she didn't. Somewhere deep down in her psyche she felt dominant and remained collected. She could feel the man's penis pulsing against her lips as he ejaculated his spend into her mouth.

She looked up and met his eyes staring at her through the viewing port and she held his gaze as she moved her mouth up and down on the man's turgid rod and sucked the last vestiges of the man's issue from him. She could feel that her cock was hard, threatening to break free of the gusset of her tights and knickers. She could feel the wetness of her precum leaking into her knickers as she suckled on the man's cock.

The man looked down into Crystal's pretty face, her green eyes enhanced by mascara, eyeshadow and eyeliner, her red lips moving up and down his shaft, leaving a trail of red lipstick. She was staring at him, making the man feel guilty while she felt simultaneously subservient but powerful but the intensity of his orgasm was such that any self-loathing the man felt was suppressed.

Crystal discovered that working her lips along the man's shaft whilst her tongue slurped his glans produced the maximum pleasure for the man and was rewarded with a series of gasps and groans as the last of his issue flooded her mouth.

She swallowed it all and did not find it repugnant as she thought she might. It tasted of the man's essence and taking it made her feel a little potent and more than a little concupiscent. If the man wasn't able to see her, there was no doubt that she would free her own turgid penis from her tights and knickers and give it a tug.

As it was she didn't need to. She felt a subtle warmth course through her body, slightly intensifying in her groin and she realised that she had filled her knickers with semen. She had climaxed almost without being aware of it because she was so centred on her mouth and the big cock that was inside it. The warm dreamy orgasm was not as intense as the earth-shattering explosive climaxes that she sometimes felt but it was very satisfying.

When Crystal had licked the man's cock clean and he extracted it from the glory hole she fell back on her heels and pushed herself upright, holding her slip away from her body so as not to get her semen on it. She made her way to the bathroom where she cleaned herself, fixed her makeup and put on fresh knickers and tights and returned to the bedroom to dress.

She sat next to the door and ate breakfast with the man as he read her the daily news, neither of them commenting on the turn of events that had just occurred.

Before supper that evening the ritual was repeated but this time the man held out a little longer and Crystal was able to improve her technique. By the end of the week she was an accomplished fellatrix and had developed various tricks and techniques to prolong the man's endurance or to make him erupt in her mouth almost instantaneously. That feeling of being a subjugated prisoner but with a subtle hold over captor continued to grow.

More and more often she dreamed of being rescued by her hero from some unfathomable and indescribable doom and surrendering herself to him. The actual mechanics and fundamentals of what that surrender entailed were hazy. All she could remember on awakening was that he held her in his arms and did something to her that caused her the most exquisite bliss. She often found that she experienced a nocturnal emission during these dreams and would have to get out of bed and change her knickers.

Then

The three attractive crossdressers made their way through the crowded main bar of the Black Sheep. Brittany led them out back to a larger lounge area. Faux tapestries of red velvet and gold adorned the walls, mock ivory columns adorned with plastic climbing ivy and gilt-framed mirrors reflected a feeling of exotic splendour. Crystal didn't know what to make of it; she hadn't seen anything like it before. She stared at a full-size plaster statue of a nude male.

A flat-chested woman in a sequined flapper dress had just finished a number on the small stage and she bowed low, her arms extended gracefully, acknowledging the applause. The air was thick with smoke and heavy with perfume. There was an abundance of tall slender women, some in evening gowns but all dressed in finery, exquisitely made up with manes that cascaded to their shoulders, silver blonde, molten red, raven black. Their wardrobes were revealing; with lots of leg on show and some were showing obviously enhanced cleavage.

There were young men too, wearing tight jeans, white t-shirts and denim jackets, possibly a little eyeliner; their hair styled, their lips in a permanent pout. But the transvestites and rent boys were outnumbered by the onlookers: men with beady eyes and wet lips; some dressed in suits, others who looked like they had just finished work in the foundry. Not all them stared hungrily at the fetching transvestites and beguiling young men, most seemed happy just to be immersed in the atmosphere.

Upon closer inspection the pageantry was revealed to be tawdry, cheap and imperfect. The decorations were dusty and dilapidated, the women's makeup was a little too heavy and often poorly applied, their clothes, which at first seemed resplendent, were often ill-fitting with seams coming apart, sequins missing, stockings laddered and wigs askew. Certainly a few were visions of perfection but most were imperfect but obviously happy and content to be somewhere where they could fulfil their fantasy.

Brittany led the trio to a small table near the wall close to the stage. To say that Crystal was terrified was an understatement but underneath the apprehension she was secretly thrilled. Besides the lewd comments, the groping hands and catcalls there was the fear that at any moment someone was going to call out: "Colin! What the fuck are you doing dressed like that!" but of course that never happened.

Once they were settled at their table a man came over and smiled at them.

"The usual Luv?" he asked Wendy.

"Yes please Bill," Wendy smiled back at him.

"And you my pretty? I've not seen you in here before," the man smiled at Crystal and she blushed.

"Gin and Britvic bitter lemon please," Crystal whispered.

She needed the alcohol to give her Dutch courage.

"Right you are Luv," the man winked at her and fought his way to the bar.

"We never pay for drinks and this table is always left vacant for us," Brittany explained.

"The Admirers keep it for us. There's Jackie and Vicky over there. Vicky is the one wearing the unfortunate blue eyeshadow," she waved at a table across the crowded room where two other crossdressers were sitting.

One was tall and the other was dumpy but they were both dressed nicely and wore heavy makeup. They were not as polished as Crystal, Brittany and Wendy but they had attracted a couple of likely lads who were chatting them up.

"Talk about showing you her knickers for bite of your toffee apple, that Vicky can suck a tennis ball through a garden hose," the two girls broke up in screeching laughter.

"I can see you're nervous but try to relax. Here's how it goes. Tonight we have a few drinks, a natter and a laff. The Admirers will buy us drinks and offer to take us home or to go with them down by the canal. Just remember you don't have to do anything you don't want to. There are girls like us that come in here and never engage with the Admirers; it's a safe space for us," Brittany began to explain.

"What are these Admirers I hear you speak of," Crystal asked.

Becoming engrossed in the conversation took Crystal's mind away from the trepidation she had been feeling.

"The term 'Admirer' in our special community refers to men who are honestly interested in socialising with crossdressers. Of course there is the risk that some Admirers may be sexual predators and to be honest a lot of them are after a quick shag or a blowjob from a tranny. Admirers are sometimes called tranny chasers," Brittany pointed out.

Crystal turned up her nose at the utterance of the words shagging and blowjobs, and the other girls saw her.

"Just remember you don't have to do anything you don't want to," Brittany patted Crystal's shoulder reassuringly.

At that moment the Admirer came back with their drinks and set them down on the table. He'd bought himself a pint.

"Mind if I sit here for a bit?" he pointed to a spare chair and Brittany nodded.

Wendy was already deep in conversation with a man in a suit sitting at another table close by.

"Crystal, this is Bill," Brittany made the introductions and Bill took Crystal's hand and kissed the back of it.

Crystal flinched a little at the gesture.

"Bill is one of the nice guys Crystal. He likes our company but he's not a tranny chaser," Brittany said, kissing Bill on the cheek.

She affectionately rubbed away the lipstick she'd left on his cheek with her thumb and Bill blushed.

"I'm sixty years old Luv and if I'm lucky the missus lets me hop on top of her once a week and if I'm really lucky she's wearing her sheers and heels because she knows I like them but I've neither the energy nor the inclination to go chasing transvestites. I just like looking at them and talking to them. My missus says it doesn't matter where I get my appetite so long as I only eat at home," Bill raised his pint and they all laughed and clinked glasses.

Bill joined in Wendy's conversation with the besuited Admirer leaving Crystal and Brittany to talk privately.

"Look we all have our stories. Usually they are very similar but seldom exactly the same. Take Wendy for instance. Her male name if William and he's married with two kids. Like all of us she started wearing her mother and sister's knickers and nylons at an early age and progressed to playing dressup. Wendy has purged so many times that she's lost count but she can't kick the compulsion to dress," Brittany took a sip of her drink.

"William has been caught crossdressed a number of times, firstly by his mum and dad and later by his wife after he got married. He promised his wife he'd stop but he just can't. None of us can. Most of us have tried," Wendy took cigarettes and a lighter from her purse.

"His wife kept finding evidence that he was still dressing and finally gave him an ultimatum for the sake of their marriage and the kids. William could go out as Wendy twice a week but she didn't want to know where or what he got up to. He was never to bring any of his female accoutrements home and never to talk to her about it. If he got caught by anyone who knew them or arrested by the police their marriage was over so he had better be discreet about it, was what was finally agreed upon," Brittany explained.

"William lied to his wife and told her that crossdressing just made him feel comfortable and appealed to his feminine psyche. He told her that it was nothing sexual and he has no compunction to engage sexually with men or other crossdressers. He leaves his stash of clothing at my place in the shed out back and he dresses there and we go out every Friday night and he comes back to my place to change in the shed before he goes home," Brittany lit two cigarettes and gave Crystal one.

"Wendy obviously does have sex... well she certainly implies it," Crystal took the preferred cigarette and took a drag.

Colin seldom smoked at home but liked a cigarette when he was down the pub having a drink.

"She fucks like a bunny. I'm not taking her inventory dear, I like sex too, but I won't let her bring men back to mine while she's being dishonest to her wife. That might be strange morality for a queer closet crossdresser but it keeps my conscience clean. What Wendy does down by the canal is her business," Brittany smiled a knowing smile.

"You called yourself a queer closet crossdresser; what does that mean?" Crystal was genuinely interested.

"Oh you want to hear my story do you? Well hang onto yer knickers while I tell you, but first smile and wave at that burly looking bloke in the Manchester United football jumper," Brittany pointed to the man leaning on the bar leering at them.

Crystal was horrified but she was in safe space apparently so she did as she was told and smiled and waggled her red nailpolished fingers at the brute of a man who turned out to be a charmer and bought the ladies another round of drinks. When he delivered them he whispered something in Brittany's ear.

"Yes darling of course you can. Meet me at my place half hour after closing time," Brittany kissed the man on the lips.

It was the first outward show of affection Crystal had witnessed at the pub but as the night wore on and the drinks flowed there was slap and tickle aplenty. The two slappers Jacky and Vicky ended up sitting in the laps of two middle-aged men, one of whom clearly had his hand up Vicky's skirt.

"Roger is one of my regulars. Unlike some, I have a small following of Admirers who I allow to grace my door," Brittany side-eyed Wendy when she said 'unlike some'.

"So... What is there to know about Brittany Swallows?" Brittany lit another cigarette and began her tale.

Brendan Small knew that he was different early in his formative years. He lived with his divorced mother in a very nice house. His mother received a very nice stipend from an errant husband to ease his guilt about running away with his secretary which his mother referred to as 'so cliché as to be hackneyed'. His mother fawned on Brendan and all but smothered him.

Brendan grew up tall and slender and was effete from the start and his mother did nothing to discourage this, allowing him to play with dolls and play with girls who took delight in dressing him up and putting makeup on him.

Brendan was too tall and athletic for the other boys to tease and one or two bullies who tried it on with him ended up with black eyes. He didn't hide his predilection for the arts and sang in the school choir and acted in school plays but the thing he enjoyed most was ballet.

Encouraged by his mother Brendan took ballet lessons three times a week. He became an avid crossdresser with an impressive collection of tights, lingerie, skirts blouses and even a pair of high heels. He spent hours alone in his room dressed as Brittany, perfecting his makeup skills and feminine mannerisms.

Dancing gave him the opportunity to not only flex his body but to wear tights and a little makeup in public which thrilled him as much as the dancing did. He soon discovered that there were other boys who practiced ballet who had similar predilections and not long after he turned eighteen Brendan discovered the carnal joys of frottage. Rubbing his engorged penis trapped in his ballet tights against another boy's penis similarly cloaked in spandex was quite thrilling and often produced an orgasm.

These trysts, which would have horrified their ballet mistress if she knew about them, took place under the stage, in the changing room or wherever the boys could meet with secrecy. Their ballet master, an equally effete man in his forties was very much aware what his charges were getting up to but said nothing. He was a man who liked to watch.

Brendan let a boy named Maurice De Witt into his secret one day when he invited him home. Maurice was keen to see what Brendan looked like dressed as a girl and as his mother was away for the weekend at a Shakespeare festival in Stratford, Brendan was happy to oblige.

Brittany came down the stairs dressed in a tight black vinyl miniskirt, a red satin blouse, black high heels and sheer tan nylon tights. Her makeup was heavy but perfect and she'd teased and styled her long boyish mullet into a long feathered do with big flicked sides. As Maurice watched her tread carefully but gracefully down the stairs he thought she looked gorgeous and sexy and would never have recognised Brendan under the makeup, hair and clothes.