The Captive Crossdresser Ch. 01

Colin wondered how many Mondays he had gone to work with the vestiges of makeup still on him. Had any of the office girls noticed? Surely not! They would have said something. They would have teased him.

"Tell me all about it," Maureen handed Colin a tea with milk and two sugars without asking him what he wanted.

There was something about the matronly but pretty woman that made Colin feel comfortable in her presence and he told her everything.

"So you're just a beginner then. But you have the right stature and build to present quite convincingly," Mrs Cashmore smiled at him and sipped her tea.

"So how do you know so much about men like me?" Colin asked.

"Well I guess over the years I've seen so many of your type in here and I started just being friendly and offering advice without being intrusive. Then a couple of crossdressers actually asked me direct questions about how to pass and I helped them out. I suppose I'm kind of like a stepmother to some around here," Maureen dunked a McVitie's digestive biscuit in her tea and daintily nipped at it.

"I have two girls, Wendy and Brittany, who shop here regularly and take my advice. I might introduce you to them at some time but first I would need to get you sorted," she dunked and swallowed the remainder of her biscuit.

Sitting talk to this woman, immersed in the cloud of her flowery perfume and listening to the slight Scottish lilt to her voice was comforting somehow and Colin instantly trusted her.

"Crystal... Crystal Divine," Colin felt a little embarrassed saying his femme name out loud.

"What a delightful and appropriate name," Maureen's face lit up in a beatific smile.

She picked up the red high heels and dangled them in front of Colin's face.

"Shall we see if they fit?" she smiled at him conspiratorially.

Colin nodded.

"But not like this. Not while you are wearing your male attire. Come back tomorrow at the same time and bring your best wig and makeup and you can take a few items off the racks and we'll see what we have to start with," She patted his hand again.

"Are you sure Mrs Cashmore? Do you really want to help me?" Colin was very pleased that she had offered.

"Of course you silly boy. Now finish your tea and get about your way. I need to get home and make Mister Cashmore his dinner," she patted his hand a final time and made herself busy getting ready to close up the shop.

The next day Colin turned up at Oxfam at the appointed time both excited and nervous. Mrs Cashmore ushered him inside and closed and locked the door. Colin felt quite the conspirator.

Mrs Cashmore was wearing another suit similar to the one she had worn the day before but this time it was mauve. He also noticed that she was wearing seamed stockings which made him envious of her.

"Look Crystal. There's really nothing to be nervous about. This is a safe space and you are safe with me. The best way to get started is for you to go into the dressing room there and transform for me and we'll see what Crystal looks like. I've put a skirt and a blouse that should fit you and those red high heels you like in there," she turned Colin towards one of the dressing rooms and patted him on the buttocks to send him on his way.

Colin felt a little silly and anxious at first as he emptied out the shopping bag he was carrying onto the little table Mrs Cashmore had put in the fitting room. A platinum blonde wig stuffed with newsprint so that it kept its shape and wrapped in a hair net fell out on the table along with a makeup case, a pair of pink nylon knickers and matching bra, a package of Pretty Polly tights.

He pulled the curtain closed and stripped feeling very vulnerable being naked and alone in the store. His nightmare was that Mrs Cashmore would rip open the curtain while he was halfway through transforming and all of his family and workmates would be standing there laughing at him.

That didn't happen of course and as soon as Crystal began applying her makeup, her attention was diverted to being as careful as possible putting on her cosmetics so as to try and impress Mrs Cashmore. She put on her knickers and bra, stuffing the cups with old pairs of tights to fill them and then slipped into her tights, marvelling at the luxurious feel of the silky garment as it slid up her legs. If Crystal was a real woman she would wear sheer tights every day she thought. Next she stepped into the skirt and pulled on the blouse, still unfamiliar with it buttoning on the opposite side to her men's shirts.

She straightened the blouse and tucked it into her skirt which she zipped closed and adjusted so that the hem was level five inches above her knees. She put on her wig and brushed it out. It had a fringe that came just above her eyebrows and the nap fell to her shoulders. Putting on the high heels was quite a feat as she had never worn heels this high before but they fit perfectly and she was able to balance of them and check herself out in the full-length mirror.

Crystal was amazed at her transformation every time she did it. How she went from being a short skinny man to a svelte sophisticated woman never ceased to astonish Crystal.

She took a deep breath and pulled aside the curtain and stepped out of the booth, unsure of her footing like a new-born foal.

Mrs Cashmore suppressed the urge to laugh. Crystal might see herself as a beautiful sophisticated woman but the reality was that she was an awkward scrawny man in a skirt wearing costume makeup and a bus driver wig but she would never tell Crystal that and ruin their budding relationship and take away any confidence she had.

But Maureen Cashmore knew that she had her work cut out for her.

"You look beautiful Crystal. Come over here and let me look at you a little more closely," Mrs Cashmore said.

Crystal staggered over towards Mrs Cashmore and was grateful when the woman reached out and grabbed her to stop her falling.

"I'm not used to wearing such high heels," Crystal apologised as she clung to Mrs Cashmore.

"Nothing I can't teach you. I can teach you quite a few things in fact," Mrs Cashmore smiled at Crystal and she suddenly realised how beautiful Mrs Cashmore was.

Being held in her embrace, feeling her breasts pushing into her, smelling her perfume and looking into her cat-like green eyes Crystal suddenly found herself becoming concupiscent. Crystal was well endowed and her erection tented her skirt and she hoped like hell that Mrs Cashmore did not notice.

But Mrs Cashmore did.

"You don't know how to tuck do you?" she pointed at the offending protrusion in Crystal's skirt.

Crystal was mortified. Mrs Cashmore had noticed that she was aroused. This was a constant problem for Crystal. Transforming was a ritual that was almost religious to her. As she progressively morphed from Colin to Crystal her psyche changed with her appearance; as her physical semblance changed, so did her mind-set. She actually became the woman she saw in the mirror. Nothing of Colin was left... there was only Crystal.

But there was also the fetishic aspect of the transformation: the delightful feeling of silky sleek nylons, knickers, and slips, the taste of lipstick, the scent of cosmetics and perfume, the luscious sensation of the hem of her skirt tickling her thighs. There was something downright sexual as well as psychological going on which usually resulted in Crystal becoming tumescent.

The most obvious way that Crystal dealt with this was to masturbate. This was part of the ritual anyway but usually occurred later, when she had been dressed for a while and could no longer resist the temptation to relive herself. On occasions when she didn't want to be hindered by a pesky erection to spoil the lines of her clothes she simply masturbated before she transformed but she hadn't today and could hardly do so now.

"I'm sorry Mrs Cashmore. What do you mean by tuck?" Crystal hoped that by paying attention to the subject of tucking rather than her erection it would diffuse the issue.

But the two were intrinsically linked.

"There are several methods of tucking; it depends on what you are trying to achieve. If you want your pubis to resemble the female form then it will require the use of cosmetic or surgical tape. If you just want to keep your genitals from ruining the outward appearance of your clothing, usually the gusset of your tights and knickers will do the trick," Mrs Cashmore explained.

"But I'm afraid either way you will have to be flaccid to achieve a tuck and once you are in the condition you find yourself in now Crystal, the only solution is to dissipate the tumescence," Mrs Cashmore said a little sternly.

"I'm sorry Mrs Cashmore, what do you mean?" Crystal was still blushed with embarrassment.

"Oh for god sake young lady; you need to do this," Mrs Cashmore stepped forward and slipped her hand under Crystal's skirt.

It all happened so fast.

Maureen Cashmore was so close that Crystal could smell her perfume and feel her sweet breath on her cheek and her breasts pressing into her own. Mrs Cashmore took Crystal's erection in her fingers through the slinky layers of nylon and softly caressed it.

The sensation was astounding. Crystal had frequently masturbated with panties and nylons wrapped around her cock but the feel of her organ being squeezed by this beautiful woman through her soft silky knickers and tights was like a thousand butterflies fluttering against her tender parts.

Mrs Cashmore held Crystal close and tenderly caressed her pulsing phallus through her knickers and tights. She was impressed with the length and girth of Crystal's penis and she began to slowly stroke it, feeling the little globules of pre-ejaculate leak from Crystal's glans and soak into her knickers. Mrs Cashmore used a steady rhythm, the swish of Crystal's knickers rubbing on her tights gusset the only sound in the room as Mrs Cashmore worked her fingers back and forth along Crystal's throbbing cock.

"Ah..." Crystal sobbed quietly as she ejaculated into her knickers.

The feel of the gossamer garments caressing her turgid, tender parts and the unrelenting feathery pressure of Mrs Cashmore's fingers was all too much. As she flooded her knickers with warm ejaculate Crystal's knees began to buckle and she held onto Mrs Cashmore to keep from falling.

Mrs Cashmore put her lips to Crystal's and kissed her softly, slipping her tongue into Crystal's mouth. Mrs Cashmore could feel her own knickers becoming damp but she would take care of that problem at home with the help of Mr Cashmore.

She softly kissed Crystal as she held her tight and expressed the last of her issue into her knickers and tights.

"Hold your skirt away from your crotch Crystal, we don't want to get semen stains on it," Mrs Cashmore said matter-of-factly, as if nothing particularly novel had just happened.

Crystal regained her composure as Mrs Cashmore disengaged and went to fetch some tissues. Not that Crystal had much in the way of composure, standing unsteadily on her high heels holding her skirt away from her semen-soaked knickers.

Mrs Cashmore returned with tissues, took a handful and dabbed at Crystal's tights, soaking up the gobbets of ejaculate that had pooled in the front. Then she pulled them down around Crystal's ankles and had her kick them off.

"Now take off the skirt and knickers and go and bring back a fresh pair of tights and knickers," Mrs Cashmore said as casually as if she was asking Crystal to fetch a newspaper.

She handed Crystal a plastic bag in which to put her soiled underwear.

Crystal returned from the dressing room naked from the waist down holding her high heels, a fresh package of tights and clean pair of knickers.

"Ok Crystal; step into you tights and pull them up to your knees," Mrs Cashmore instructed.

"But what about my knickers?" Crystal asked as she took the new tights out of their packaging.

"Ok darling. You might see a lot of women wearing their tights over their knickers but they are doing it wrong. The aesthetic is so much better when you can see the pretty panties properly. Why go to the trouble of buying nice knickers if you are going to spoil the appearance by putting the gusset of your tights over them?" Mrs Cashmore explained.

"Also for the crossdressing community putting your knickers over your tights helps hold your tuck in place as I'm about to demonstrate," she continued and stepped up to Crystal who was standing with the new tights pulled up as far as her knees.

"Now, I'm going to touch your privates again Crystal but this time it is for very practical purposes," Mrs Cashmore proceeded to show Crystal how to tuck.

She explained the procedure to Crystal as she did it.

"I'm going to push your testes back up inside of something called the inguinal canals. This is where they were before they dropped in puberty. With your index fingers, locate your testes and begin pushing them toward your backside. The next step takes practice: gently push them back and up, curling your fingers inward toward you as you do," Crystal felt uncomfortable as Mrs Cashmore did this but it wasn't really painful.

"Now pull up your tights a little and pull your penis and scrotum back between your legs and pull your tights all the way up and get them snug and put your knickers on and pull them up too. Your knickers and tights should now hold everything in place," Mrs Cashmore helped Crystal do this.

"How does that feel?" Mrs Cashmore asked.

"It sort of feels awkward but I can see it looks fantastic," Crystal beamed as Mrs Cashmore held a small mirror down low so Crustal could see the results.

"Looks just like a woman's pubis doesn't it?" Mrs Cashmore grinned.

"That will work fine for around the house or just for a little while but if you're going out I strongly suggest you tape everything in place with cosmetic or surgical tape. Now untuck and do it again for me a couple of times so I can see you've got it right," Mrs Cashmore instructed.

When Mrs Cashmore was happy that Crystal had tucking mastered she looked Crystal in the eyes and spoke forthrightly.

"You really are a beginner at this and you have amazing potential but you have so much to learn. You think that you look very feminine and beautiful after transforming yourself from Colin to Crystal but the reality is you would be clocked on the streets in thirty seconds. Let's start all over shall we? First off makeup..." Mrs Cashmore spent the remainder of the evening having Crystal get her makeup right.

Over the next few weeks Mrs Cashmore taught Crystal all about makeup, styling wigs, how to speak with a feminine inflection, how to walk, how to naturally use feminine gestures.

Mrs Cashmore never touched Crystal intimately again but Crystal never forgot the delightful feeling of having Maureen caress her genitals and kiss her. It fuelled her masturbatory imagination for weeks.

Now

Colin was no more. There was only Crystal.

After two weeks of confinement Crystal had been conditioned to obey the rules. She had no other choice. What she eventually admitted to herself was that living full time as Crystal and abiding by the rules was quite comforting. She liked the routine of it, the regularity of it and hadn't Colin often dreamt of living his life full time as Crystal?

She wondered what was going on in the outside world. After a week's absence she would be missed. Colin worked in the offices of a stationery manufacturer. He didn't have many friends there but there were work colleagues who would miss him and a client base whose accounts needed to be managed.

His family wouldn't miss him until he missed a birthday or some other family occasion. His tyrannical father had no real love for his diminutive Nancy-boy son who would rather play dressup with his cousins than kick a football with his dad. Colin was useless at football and all sports anyway and had leaned into the arts which at first his mom had encouraged but had succumbed to her overbearing husband's wishes and she then discouraged his participation in theatre and entertainment.

His mother and father were glad when Colin left home and they had undertaken a tacit agreement to meet only on special occasions. The only show of affection he had received before Colin left home was the gift of a pair of emerald earrings which his mother had given him, telling him that they were a family heirloom and that Colin should give them to his wife when he married.

"Fat chance of that Nancy ever marrying," his father had growled as he closed the door on Colin with a thunderclap of finality.

The only people Crystal had regular contact with who cared about her were Wendy and Brittany but she knew little about them outside of their shared adoration and devotion to crossdressing.

The post would build up, Colin's rent and other bills would remain unpaid, his clients would pester his boss. Someone would miss Colin Divine. But who? And when?

There was a comfortable predictability in her life such as it was. Crystal explored her cell, because that's what it was, a gilded prison cell, and had found that she had everything she needed. The bathroom was a small practical space with toiletries still in the packaging. A good quality razor, toothbrushes, hair brushes, scissors, tweezers were provided along with toothpaste, razor blades, soap, shampoo, conditioner, mouthwash, and other beauty products.

There was a shower, no bath but that was unsurprising given the room was likely a converted basement or coal cellar. It was newly tiled and functional. Hanging near the shower was an enema bag fitted with a hose and under the sink was a squeezable bulb douche. Crystal knew what they were although she had never used them before. The rules mandated that she use them daily and she didn't want to think about why.

Crystal was a connoisseur of antique furniture and was fascinated by the immense wooden repository which took up the whole wall of the main room. It was a magnificent piece.

It was an antique Italian neoclassical burl walnut armoire with bronze mounts. It had two full-height doors on each side which opened to reveal an immense hanging space. The two cabinet doors at the centre opened to reveal a cavernous storage area fitted with shelves and a vanity mirror with a light fitted above it. Below that were four exterior doors with a graceful bow-front shape that provided visual contour to the massive piece, inside of which four drawers and a shoe rack were concealed. The exterior was swathed in exquisite burl mahogany bordered with satinwood marquetry in an intricate floral pattern.

It was a fine piece of practical art.

The clothes that she had worn to The Black Sheep the night she had been kidnapped were hanging in the hanging space along with an assortment of skirts, dresses and blouses. Her high heels were neatly arranged on a rack on the floor of the armoire along with three other pairs in black, red and white.

Three wig stands were lined up on a shelf and her platinum blonde wig was fitted to one and the other two had brunette and black-haired wigs fitted to them. They were styled identically: shoulder-length tresses cut into fringed bobs.

What Crystal found a little disturbing at first was that all of the shoes and clothing fit her perfectly, as did the abundant array of lingerie she found neatly arranged in the drawers.

The man who was keeping her prisoner knew her sizes. What else did he know about her?

The centre section of the armoire was fitted with shelves filled with cosmetics, perfumes, and makeup sponges and brushes. Above the shelves was a vanity mirror fitted with good quality lights. There was a walnut stool on which she could sit to put on her makeup.

When she followed the rules and daily duties to the letter she was rewarded accordingly. If not, she spent the day in total darkness alone. She began to crave listening to the disembodied voice that came through the door and looking at the hand that came through the cat-flap to deliver her food and necessary items and to take away the trash and her laundry.