The Captive Crossdresser Ch. 02

Chapter Two -- Ba Ba Black Sheep

Then

Mrs Cashmore played Professor Higgins to Crystal's Eliza Doolittle as she educated the young, inexperienced crossdresser in the art of female impersonation.

After many lessons over two months Maureen Cashmore decided that Crystal Divine was just about ready to come out to the world.

"Tomorrow when you come to my shop, bring your jewellery and we will add the finishing touches to your transition and I have a gift for you and another surprise," Mrs Cashmore said to Colin as she ushered him out the door of the Oxfam shop one Thursday night.

"You've been so gracious and supportive of me Mrs Cashmore. How can I ever repay you?" Colin gushed as he halted briefly in the doorway.

"My reward is seeing you as Crystal and knowing that I had some small part in helping you become her," Mrs Cashmore closed the door on him.

The next evening Crystal dressed in a nice suit consisting of a tight pencil skirt with a kick-pleat in the back, the hem resting four inches above her knee. She had a matching long-sleeve jacket and wore a white satin blouse under it. The suit was dark red and was very corporate.

Under her clothes she was wearing sheer flesh-toned tights and had tucked with tape to keep it tight. Over her tights she was wearing white satin full-cut panties and she wore a matching bra inside of which was the present that Mrs Cashmore had promised her.

"They are called breastforms dear and they are made from good quality silicone and are as realistic as the real thing," Mrs Cashmore said as she unwrapped Crystal's present.

Crystal was delighted with the prosthetic breasts which looked so realistic, even the nipples and areola looked natural. She had been using her old tights to pad her bras up until now and although they did the job they were not on a patch on the breastforms.

Mrs Cashmore showed Crystal how to fit them, carefully cleaning her chest area with an alcohol wipe and applying three-pieces of double-sided tape to the back of each breastform and then placing the forms gently against her chest and holding them in place for five to ten seconds to allow the adhesive to bond and then immediately putting them in the cups of her brassiere.

As with her shoes and clothes, Mrs Cashmore had an uncanny knack of getting Crystal's size just right and the breastforms were in perfect proportion to her body.

Crystal was wearing her platinum blonde wig and black patent leather four-inch high-heels.

"Now for the accessories. Let's see what you have brought me," Mrs Cashmore said enthusiastically.

Mrs Cashmore's enthusiasm disappeared when she saw what Crystal had brought. It was a mismatched jumble of junk jewellery that Colin had purchased at the flea market.

"I'm sorry darling but everything except those gorgeous earrings are trash," Mrs Cashmore poked her long manicured fingernail through the pile of junk jewellery rescuing the emerald earrings that Crystal's mother had given her.

Crystal told Mrs Cashmore the story behind the earrings.

"Let's put them on you and we'll see what I have in the store to go with them shall we?" Mrs Cashmore smiled at Crystal, making her feel better.

In the early seventies hippies and bohemian types adopted the wearing of earrings and the once-taboo quickly turned into a fad, catching on in the celebrity community, with musicians, performers and athletes beginning to pierce their ears as well so when Colin went to the local beauty salon and got his ears pierced it wasn't considered a big deal.

Crystal had tried wearing clip-on earrings but they didn't sit right and drop earrings often fell off and there wasn't the range and selection as there was for earrings designed for pierced ears.

Crustal put on her earrings while Mrs Cashmore scoured the store's costume jewellery collection for a matching necklace and bracelet. She found the items she was looking for: a train of small synthetic emeralds set in a silver-plated nickel chain and a matching bracelet donated by one of the local parishioners along with a ring of similar construction set with a large synthetic emerald donated by the same lady.

"Here let me help you put these on," Mrs Cashmore stood behind Crystal and closed the clasp on her necklace and then did the same with the bracelet.

The ring was a little tight on Crystal's ring finger when she tried to put it on but she managed to get it over her knuckle and then the fit was snug but tolerable.

Mrs Cashmore sprayed Crystal liberally with perfume and stood back to admire her.

"You look beautiful my dear. You have worked so hard that it is very unlikely that you would be clocked unless the person was sitting right beside you and even then it would be difficult," Mrs Cashmore gushed and Crystal blushed.

"I have one more present for you my dear," Mrs Cashmore produced a stylish black leather handbag from under the counter.

"This will go with almost every outfit in your wardrobe," Mrs Cashmore dropped Crystal's keys and wallet into the handbag.

"You'll need to put in a little makeup, your perfume and lipstick my dear," Mrs Cashmore held out the handbag to Crystal who looked confused.

"A girl can't go out for a night on the town without her handbag can she?" Mrs Cashmore gushed.

Crystal was caught totally unaware and was appalled at the prospect.

Just then the little bell above the door rang and Mrs Cashmore rushed over to open the door while Crystal stood stock-still, shocked at the notion of going out into the world presenting herself enfemme.

Mrs Cashmore ushered two ladies obviously dressed for a night out on the town into the shop and closed the door behind them

"Crystal Divine meet Wendy Doesit and Brittany Swallows," Maureen Cashmore gushed as she introduced the three femme crossdressers.

Brittany was tall and slim and her hair was a flaming-red styled updo worn with a fringe; very vintage. As was the navy-blue 1950s suit complete with a pencil skirt with a single-breasted jacket with buttons down the front and French-ruffle-fronted white satin blouse she wore under. The suit was cinched at the waist and fitted to the curves of her body. Her long legs were clad in black Cuban-heeled, fully-fashioned seamed stockings and her high-heels were open toed to show off the reinforced toes of her nylons.

Brittany's makeup was also vintage and her foundation matched her natural skin tone, red lipstick, elegant eyes defined by eyeliner and mascara. Her eyeshadow was grey with a hint of silver. Her cheeks were sparingly rouged, a mere hint to add a soft warmth to her face and her brows were arched and pencilled in to define her eyes.

Brittany was obviously very adept at putting on 'a look' and she exuded confidence. She looked like she had just walked off a photo-shoot for a 1950's Pretty Polly nylon stockings advertisement.

"Pleased to meet you," Brittany took Crystal's hand and leaned in and air-kissed her so as not to smudge her lipstick as she surrounded Crystal with miasma of perfume.

Wendy Doesit was dressed totally the opposite to her girlfriend in full 1970s fashion. She was a 'chubbette' but she carried the weight well.

She wore a bright-yellow A-line miniskirt with a matching bolero jacket over a black satin blouse, tan nylons and white knee-high PVC boots. Her makeup was bright with pink lipstick and she wore a black bob with a fringe that nearly covered her eyes. Very chique.

Wendy hugged Crystal and gave her the obligatory air-kiss.

"These are the other girls I told you about. They shop here often and I put aside items that I think will interest them," Mrs Cashmore said by way of introduction.

"Mrs Cashmore is our surrogate mom. She gave us tutorials when we were just starting out," Wendy explained.

"And I can see she has done a fantastic job with you Crystal; you look stunning," Brittany chimed in.

"You'll be fine with us; you'll have a wonderful night out. Where we are going is safe for special girls like us and in fact we are the centre of attention," Wendy winked salaciously at Brittany.

Crystal was both flattered and alarmed. Mrs Cashmore had spoken to her briefly about Brittany and Wendy but she had for all intents and purposes ambushed Crystal who was not confident about going out on the town, not even in the company of these two other girls.

Also there was something a little tawdry about the girls besides their somewhat suggestive names. Wendy in particular seemed overeager and solicitous, almost desperate.

"You can leave your male clothes here and pick them up on Monday and then you can tell me all about your first night out on the town as Crystal," Mrs Cashmore fussed about Crystal making sure she looked perfect.

Crystal was really alarmed now.

"But that means going home dressed as Crystal! What will the neighbours think?" Crystal gasped.

"Darling, the neighbours are hardly likely to be up at that time of night even if anyone saw you, all they are going to wonder about is who is the gorgeous young woman visiting Colin Divine at that hour?" Wendy sniggered.

"You're unclockable darling. No one is going to know Colin even exists under that slap, wig, nylons and heels," Brittany supported her partner's hypothesis.

"Ok you lot. Off you go. Mister Cashmore is taking me to the flicks tonight and if he's lucky I'll let him have a kiss and a cuddle and feel-up during intermission," Mrs Cashmore winked at the girls and then shooed them out the door.

It was a ten minute walk from the Oxfam shop on Oldham Street to the Black Sheep pub via Piccadilly Gardens and although the area around Canal Street was popular with gays and transgender people, in 1976 they were still targeted by prejudice and hate.

In Britain in 1967 homosexuality was partially decriminalised and gay men could have sex as long as it was in private and was only between two men and both were over 21. It still didn't feel safe to be openly homosexual and there were still laws that could be used against gay men.

Although Crystal did not consider herself gay she knew that being a man presenting as a woman in public would be inflammatory enough to ire the homophobes and there would be no protection from the police who would be more likely to arrest Crystal, Wendy and Brittany than to protect them.

Sir Cyril James Anderton was the chief constable of the Greater Manchester Police and had a policy of policing of the area heavily due to his prejudice towards the gay community. Anderton encouraged his officers to stalk the dank alleys and expose anyone of the same sex caught in a clinch or openly expressing affection.

He believed that sodomy between males was an abhorrent offence, condemned by the word of God, and ought to be against the criminal law and he publicly stated that 'the gays of Manchester were swirling in a cesspit of their own making'.

These thoughts bounced around Crystal's head whilst Wendy and Brittany nattered like a couple of teenage girls out on the town.

"Don't worry darling the coppers will leave us alone so long as we don't stop for a shag or a blowie," Wendy tittered.

Crystal was appalled.

"Don't worry about her she's just a crude doxie who can't keep her knickers on. When she was younger she'd show you her knickers for a bite of your toffee apple," Brittany giggled.

"Shut it you!" Wendy retorted.

"Seriously Crystal you're safe as houses around here and once we get into the Black Sheep no one will bother us at all," Wendy said in a solemn tone.

"Well you will be bothered, but only by people who admire you, not by people who dislike you. Remember, you're doing nothing wrong. You're just out having a good time; you're not breaking any laws," she patted Crystal's shoulder.

While all this was going on during the eternal ten minute walk, which ended up being fifteen minutes because whilst Crystal was adept at walking around carpeted and lino floors in high heels she was new to the pavement and cobbled streets of Manchester. Concentrating on walking kept Crystal from worrying too much about being battered by homophobes or thrown into the back of a black maria by the 'wooden-tops'. The only incident that occurred was when they passed two men on their way to the boozer who gazed at the three girls appreciatively and wolf-whistled.

"Show us yer knickers luv!" one of the cheeky chaps called out and Wendy obliged which of course called for another wolf-whistle.

"Here we are; safely at the Black Sheep," Brittany opened the door to a smoky, raucous, overcrowded pub.

Now

Masturbating her captor became part of Crystal's daily duties; once in the morning before breakfast and once again in the evening before dinner. The man would open the glory hole and stick his engorged manhood through the hole and Crystal would be standing there like the dog in the 'His Master's Voice' painting, faithfully waiting for her master.

She knew the consequences of refusal and once she had done it a few times it no longer repulsed her. She soon learned that semen had a way of finding its way onto her clothing no matter how careful she was so she performed her duties dressed in bra, panties, nylons and heels and sometimes a slip or petticoat. The man insisted she wear full makeup because he watched her through the viewing port, although he seldom spoke to her during the course of her duties.

The man would sigh or gasp or mew as Crystal stroked him to climax. After a while she made a game of it for herself, bringing the man close to extremis and then backing right off making the man become frustrated and then she would hold his cock tighter and stroke it faster and bring him close to climax again and back off yet again. She'd do this until the man begged her for release.

His issue would burst forth into her hand often spraying up her arm and sometimes onto her body and her face if she got too close. She had to admit a certain fascination with the man's erect penis. It was a fine specimen of elegant manhood: elongated and broad with purple veins running under the sleek velvety flesh and a glistening pink glans.

Crystal would reach out and tentatively touch it and it would quiver, then she would wrap her fingers around the turgid organ and slowly and softly stroke it. She added a new technique to her repertoire after the first few encounters; she would reach through the glory hole and softly squeeze and stroke the man's scrotum.

Working her fingers in symphony she could bring the man off quickly or if the mood took her she could torture him, making him wait for release, bringing him close to climax and then relinquishing her attention to his needs, she'd stop her ministrations until he begged her to finish him.

After the man had ejaculated he would withdraw his penis and clean himself up before opening the cat flap and pushing though Crystal's food and take away or deliver her laundry or remove the trash she had bagged for him, then they would begin their usual social intercourse.

While the man cleaned up, Crystal did the same. She would wash her hands and if the man had managed to get semen on her clothes then they would be removed and she would replace the soiled items and get fully dressed. She would return to the door and they would talk while she ate. He would read her the morning and evening newspapers and they would discuss current events but they never talked about her masturbatory duties.

One day Crystal was masturbating the man while the laundry basket sat on the floor ready to be pushed through the cat flap when she'd finished her duties and she noticed one of her stockings dangling over the side of the basket and it gave her idea. What if she put the stocking over the man's penis to catch his issue?

She did it and it was an immediate success. The first time she slid the diaphanous sensuous garment along the man's pulsing member he groaned and spent himself immediately, flooding the stocking with warm, glutinous semen. The man demanded that she do this often and even brought her packages of cheap nylon stockings to use for this very purpose so that her cache of expensive fashion hosiery wasn't ruined.

Crystal would never tell the man but she preferred it when she used her bare hand on him. It excited her feeling his penis swell and quiver at it discharged in her hand. She liked the feel of the warm secretions spattering on her skin, the musky smell of it, the creamy efflux running through her fingers. She considered it her reward for a job well done.

She kept the semen soaked stockings and items of lingerie and used them as masturbatory aids while the man was at work. She would put the semen-soaked nylon over her erect penis and bring the spunk-spattered slip to her nose and stroke herself to climax. She would never tell a soul about this of course. In her imagination she was the heroine in one of her Mills and Boon's, surrendering her virtue to her saviour.

Soon followed the demand for oral sex.

Crystal held out for three days in complete darkness during which she wasn't fed nor given any form of social interaction except for the one hour a day allotted for her ablutions.

She wasn't naïve. Crystal knew that the man would escalate and that masturbation would not sate his desires for very long. She had forgotten how long she had been held captive but she knew that it was well over a month. She knew the days of the week because the man was home on the weekends during the day. The reality was she didn't care. She had been driven into submission and was content to live by 'the rules' and anyway; hadn't she dreamt of living her life full-time as Crystal?

She was dependent on the man for everything. He housed her, clothed her, fed her, conversed with her, and gave her books and magazines to read when he wasn't there. She had nightmares that something might happen to him and she would slowly starve to death alone in this room.

Crystal consoled herself that it was unlikely that would happen because if something happened to the man, someone would come to his house for some necessity or another. But that also raised the question of what had happened to Colin Divine?

Were the police looking for him? Was he missed by his family, work colleagues and his few friends? Unlikely. What about Wendy and Brittany; would they be suspicious that they had not seen Crustal Divine for such a long a time? They were really just friends who had a corresponding interest in crossdressing, she had not been to Brittany's house nor Brittany to hers and Wendy was a married man.

The reality was that after taking Brittany prisoner her captor had gone to Colin Devine's house and let himself in using Colin's keys. Over a period of time he had donated all of Colin's clothing to Oxfam, keeping the items of Crystal's clothing and wigs that he liked and taking them back to his own home for her to use. Colin rented his house fully-furnished and the man had cleaned the place and returned the keys to the real estate agent in an envelope with a note to say that Colin had been called away overseas at short notice and that the real estate agent was to keep the bond money as payment for the inconvenience.

A similar letter was sent to Colin's employer advising the company that Colin had been called away to deal with an urgent family matter regarding his brother who was living in Australia. He was deeply apologetic and instructed his employer to keep his outstanding holiday pay until he returned but to offer his position to someone else.

This was the 1970's. There was no internet, no Facebook, Twitter or Instagram. Few people on Colin's income even had home phones. Colin was not missed by anyone. Crystal was missed by Wendy and Brittany but it was not unusual for crossdressers to suffer the onset of remorse and to purge themselves of their feminine requisites and to swear that they would never slip on a nylon stocking or a pair of knickers ever again.