One for the Team Ch. 01

Chapter One - Trans Sexcretary

Author's note: When I began this story just before Corona Virus changed our lives, it was going to be a short story about forced feminisation. With time on my hands because of the compulsory isolation the story grew and morphed into a love story and finally a 'whodunnit'.

I hope you enjoy the twists and turns and please leave comments to let me know how you feel about it.

Michele Nylons

May 2020

*****

September 1984

Charlotte Ward sat on the hard-backed chair in front on the dresser and admired the fully-fashioned stocking in her hands. For as long as she could remember she had been fascinated by the delicate garments: the eight denier, ultra-bare, flesh-toned nylon, cut to the shape, the darker shadow welt just below the coffee-coloured gauzy top-welt where the garters were attached and the manufacturers brand stylised in white lettering above the keyhole-shaped finishing loop. The dark back-seam, reinforced heel and toe, the same colour and texture as the welt.

Even though Charlotte was wearing hosiery gloves she was well aware of the cool silken sensuous feel of the garment and shivered in anticipation of sliding it up her recently shaved leg.

She lay the stocking aside and picked up the pair of peach-coloured Harlow vintage knickers. They were manufactured from polyester and lycra at the back and sides with a satin tummy panel for light control and were high-rise and high-cut to give the knickers 1950's styling. She held them to her cheek, relishing their soft luxurious feel against her skin. She could smell the residue of her perfume on the garment from the last time she had worn them. She laid the knickers beside the matching Harlow vintage brassiere and six-gartered suspender belt.

The vintage lingerie and hosiery was expensive but money was no object to Charlotte.

She checked her makeup in the mirror; it was heavy and very vintage: foundation and finishing powder, rouge to accentuate her sharp her cheekbones, black mascara and eyeliner and blended eyeshadow to emphasise her emerald green eyes, blood-red lipstick gave her lips fullness and matched her nailpolish, her jet-black, bob-cut hair with a fringe in front that framed her face and curled under her chin.

She was not being conceited when she thought to herself that the visage in the mirror looked stunning.

Charlotte shimmied into the garter belt and then pulled the knickers up and smoothed them out; the girdle of the suspender belt sat above the knickers and six garters hung down through the leg holes. She put on and adjusted the bra, then she shuddered with delight as she slid the rolled-up stockings up her legs, fastened that garters to the welts and straightened the seams; her favourite part of the ritual.

She took off the hosiery gloves and stepped into a tight, navy-blue pencil skirt; it was knee-length with a kick-pleat in the rear. She buttoned up a fitted mauve satin long-sleeved blouse, tucking it into the waistband of the skirt, smoothing it, and then zipping her skirt closed at the side. Charlotte sat down again and put on her costume jewellery and then put on her black patent leather four-inch high heels and sprayed herself liberally with perfume.

Although she had checked it twice already she once again confirmed that the door to her dorm was locked and the bolt latched.

She stood back and admired herself in the full-length mirror and was pleased with what she saw. Charlotte was only eighteen but she looked like a sophisticated sexy woman in her twenties. She turned on the floor-lamp and turned out the overhead light and spent thirty minutes or so posing in front of the mirror and then practicing her walk, made sexier because of the constraints of her tight skirt and the high heels. She blew kisses to herself and congratulated herself for being so feminine, alluring and beautiful.

Satisfied that the sound was muted on the television she inserted the video cassette into the VCR, reset the counter and hit play. The tape was titled Trans Sexcretary and it was old and had been played so many times that it took her a while to adjust the tracking but she got it right and then she fast forwarded to a pre-set position on the counter.

She stared at the television wishing she could turn up the volume but she couldn't do so in her current circumstances. Not that it really mattered; she knew every line of dialogue in the movie.

A woman came on screen dressed similarly to Charlotte but not the same. She was pretty and sexy and looked to be in her mid-thirties. She was very feminine in her mannerisms and countenance but you could tell that she was a man under the lipstick powder, heels and hose. She had entered an office and a man in a business suit sat behind a desk, the woman appeared to be his secretary. She looked shy and trepidatious and when the man spoke to her she shook her head.

The man barked angrily at her and reluctantly she walked over to where he sat and the man pulled her into his lap. What followed was a typical popular porn story: the woman at first struggling and then reluctantly succumbing to the man's advances.

The video was soft-porn, an edited version of an X-rated movie that Charlotte had been unable to purchase because at the time she was underage. She was now eighteen but hadn't been able to find a copy in any of the video shops she had been to.

The video was poorly edited and although still erotic it did not explicitly display any genitalia, sexual penetration, fellatio, or ejaculation. The woman remained fully-clothed throughout. The woman on the screen was at first reluctant but the man was insistent and as the action progressed they kissed and fondled each other. There followed a scene where the man forced the woman to her knees and she fought him but eventually she succumbed and the scene suddenly cut to her kneeling with her head bobbing up and down in his lap.

Throughout the movie, Charlotte re-enacted the part and spoke the dialogue of the woman but when the actors on the screen began to struggle again as the man pushed the woman towards the desk Charlotte pulled a silk stocking and her pride and joy, one of the newly available vibrating dilos, out of the dresser drawer along with a tube of KY jelly.

'Steven... you know I shouldn't be doing this,' the woman on the screen said.

Steven had bent the woman over the desk and hiked up her skirt and Charlotte imitated the scene, bending over the desk in her room and hauling up her skirt.

'You know you want it Doris,' the man on the screen pulled down her panties and kicked her legs open and moved in behind her.

Charlotte opened her stance and greased the rubber dildo with the KY jelly. She was fully erect in her knickers and she pulled them down to her knees and slipped the silk stocking over her erect cock. It would serve two purposes: enhance her stimulation and catch her semen so it didn't spatter over her clothes or on the floor.

'No Steven! No!' Doris struggled on the screen and Charlotte wriggled her buttocks, mimicking her.

The actual penetration on the screen had been edited out so the camera zoomed in on Doris' face. Her eyes opened wide with shock as Steven began to enter her.

So did Charlotte's as she pushed the tip of the rubber cock past her sphincter. It did hurt a little; it always did because she was so tight and the dildo was so big but it also felt wonderful. She felt so vulnerable bent over the desk with her skirt rucked up and her knickers around her knees.

'Please Steven; don't!' the woman on the screen pleaded.

The man ignored her pleas and thrust forward and as he did Charlotte slowly inserted the rubber cock all the way into her anus. The man on the screen did likewise, resting once he had fully impaled Doris.

'You know you like it,' Steven huffed; as corny a porn line as any.

'Stop! Don't! Stop! Don't! Stop! Don't! Oh my god... don't stop!' Doris squealed and Charlotte whispered the same lines to herself as she worked the dildo in and out of her anus.

Charlotte had used the device so often that she was an expert in ensuring it gave her maximum pleasure. She drove the rubber cock inside her anus, twisting it slightly so that it simulated the sensitive nerves ringing her sphincter eliciting little sparkles of pleasure and then she pushed the head of the penis-like device up so that it pressed on her prostate and evoked deep waves of bliss that spread outwards from the tender gland.

The camera panned out to show Steven with his trousers around his ankles pushing the pretty transvestite down on the desk, her skirt hiked up showing off her sheer black stockings, the pink nylon panties around her knees and her 'fuck-me' four-inch high heels. Her face was screwed up in a combination of pleasure and pain. The actual penetration was hidden by the nape of her skirt falling across her thighs and buttocks but Charlotte knew that in the X-rated release of the video, the man was actually fucking her.

'Oh god Steven I feel so naughty but I feel so wonderful,' Doris sighed and pushed back against the man fucking her.

'I knew you wanted it Doris... I've always known,' the man quoted the banal lines that the scriptwriter had given him.

Charlotte didn't care. Even though the tape was edited you could tell the expressions on the actor's faces were real; they enjoyed what they were doing.

Steven fucked Doris with long hard strokes, holding her hips and grinding his pubis into her soft buttocks. Doris had stopped talking coherently and simply moaned and groaned as the man assaulted her anus, his strokes getting harder and faster, she pushed back to meet his thrusts.

Charlotte too was grunting and squealing with pleasure. Her wrist was aching from the awkward angle as she worked the dildo in and out of her anus. She could feel her orgasm approaching even though she hadn't yet touched her cock. The tip of the silk stocking over her erect penis was wet with pre-ejaculate.

The screen images alternated between long shots of the businessman fucking the pretty transvestite and close-ups of their faces, wanton with desire.

Charlotte knew that the actors release was close and she flicked the little button on the base of the dildo and the intensity of her pleasure increased astonishingly as the dildo began to vibrate. On the screen the actors were at the pinnacle of their desire, the camera showed their faces screwed up in lust, the man pounding into the woman and then pulling her hard against him as he orgasmed. The woman sighed with lust, her hand under her skirt frantically stroking her cock and evoking her own orgasm.

Charlotte pushed the dildo hard up against her prostate and had to bite her lip to suppress a scream as waves of incredible delectation and gratification washed over her. She filled the silk stocking covering her cock with creamy semen. Her knees began to buckle and she held onto the desk with her free hand to support herself.

Later as she carefully undressed and folded her clothes, put her high heels back into the velour storage bag, removed her wig, brushed it and put it with the others, removed her makeup and sat at the dresser removing her nailpolish she felt the usual pangs of guilt and regret but knew that before long the compunction to dress and present herself as Charlotte would return and could not be denied.

The clothes, shoes, wigs and makeup went into a suitcase which she carefully locked and put away in the top of the wardrobe

Charles Ward, now dressed in cotton underpants and pyjamas, sprayed Right Guard liberally throughout his dormitory room to mask the scent of Charlotte's perfume and checked himself carefully in the mirror to ensure not a skerrick of makeup remained on his face or nailpolish on his fingernails. He knew the drill by now.

*****

Charles Ward had always had a fascination for women's clothing, especially lingerie and hosiery and had begun to collect them and secretly wear them from early adolescence. He was particularly attracted to retro lingerie and stockings. Women had recently switched from stockings to pantyhose as a matter of convenience and he agreed they had their practicalities and looked particularly good when women were wearing them with miniskirts or hotpants. He liked to wear them to bed under his pyjamas.

In his middle-teens Charles' fascination stretched to the full gamut of women's attire and he acquired a small collection of skirts, blouses and shoes. He was small statured and slim so he had no difficulty obtaining garments that fit him. His main obstacles were how to obtain them, getting the opportunity to wear them without being caught, and how to hide them from his parents and siblings.

At first he had simply borrowed his sister's clothes from the laundry basket or sometimes he snuck into her room and appropriated clothes from her wardrobe but this was risky. Being one year older than Charles, his sister's clothes fitted him perfectly.

He didn't know why he had this compulsion to dress and present as a woman, he just knew that it delighted him and made him feel comfortable...it made him feel right. Many times he had purged and vowed never to do so again but the compulsion always returned and he regretted throwing out his collection.

He began experimenting with makeup and became quite adept at it and the longer hairstyles worn by young men at the time allowed him to have a haircut that could easily be brushed into a feminine do.

The Ward family was wealthy so money was not a problem for Charles, he had a generous allowance. Provided he performed well at school he could pretty much do whatever he pleased. His parents had busy lifestyles and were often away and his brothers and his sister had their own friends and their own interests that did not include Charles and he was more than happy with those circumstances.

The Ward's had a holiday cottage in Otford. It was secluded and surrounded by woods. His father liked it because there were plenty of golf courses nearby and his mother liked the seclusion and healthy outdoor life that she and the children could enjoy. They frolicked outside in the woods, went for country walks, even camped out when they were younger. As the children became teenagers they grew less interested in the cottage and preferred city life and the Ward seniors lost interest too and rarely used the cottage but kept it as an investment.

They were delighted when Charles asked if he could use the cottage on weekends and during the holidays and allowed him to do so. This solved Charles' problems of secrecy and gave him the opportunity to dress enfemme; he would do so as often as he wanted to, sometimes spending days transformed into Charlotte, the name he had picked for his femme personality. He soon became adept at presenting Charlotte as a convincing woman; he worked on perfecting Charlotte's mannerisms, speech, gait and countenance. Charlotte's personage took up residence in Charles' psyche when she was present, nothing remained of Charles; Charlotte was an attractive and vivacious young woman.

There was a second-hand clothes shop called Cash for Clothes in Otford and Charles was one of their best customers. The two little old ladies who ran the store had their suspicions as to why a teenage male was buying ladies fashion but they weren't concerned; Charles paid in cash and was polite and effusive when talking to them about their wares. They began to put aside good quality ladies clothing and shoes in his size and preferred style knowing that he would pay a good price for them.

Charlotte had quite an extensive wardrobe in her room at the cottage and an excellent selection of makeup, perfumes and accessories.

In the mid-eighties almost every household had a VCR and the cottage was no exception. When video cassette players became freely available there ensued a boom in video cassette tape rental and sales. Video rental stores popped up everywhere and most had an adults-only section containing X-rated videos.

By now she realised that not only did she feel most normal when she presented herself as Charlotte, she also often felt sexually aroused and fantasised about having sex with another crossdresser or in some cases with a man. The video rental stores Charles frequented did have plenty of transvestite themed porn in their adults-only section but the problem was that although he could browse the aisles, he couldn't rent the movies without showing proof of age.

The good thing was that VCR tapes deteriorated quickly and ended up in the for-sale bin at a reduced price. Charles was able acquire a couple of soft-porn videos to titillate himself including Trans Sexcretary.

Charlotte's happiest days were spent at the cottage, holding her own fashion parades or just sitting around relaxing or completing Charles' school assignments for him. She often sat around reading women's fashion magazines and even took walks in the woods where on occasions she ran into people who never seemed to suspect that she was anything other than a young woman. She desperately wanted to go out in the town but she knew the consequences would be dire should she be exposed for who she was.

This idyllic period in Charles life all came to a crashing halt one Saturday afternoon when his life would be changed forever.

*****

July 1984

"Come on in Betty," Reginald Ward slapped his pretty secretary on the arse as she squeezed past him in the tight doorway of the Ward family holiday cottage.

"Come on; let's get a drink in us before we start wearing out the mattress. Just through here in lounge room there's a..." Reginald Ward stopped in his tracks.

Who was the pretty young woman lying on the lounge watching pornography on his television? How had she got into the cottage and why was she here?

Charlotte was wearing shiny pink lycra dance tights, sheer nylon footlets, black stiletto high heels, a loose fitting sleeveless top with a padded bra to give it some shape, full makeup, jewellery and perfume.

She looked gobsmacked at her father unable to speak.

It took one full minute for Reginald Ward to realise who the person was that had been lying and was now sitting, on his couch.

"Charles? Charles? Is that you?" Reginald stammered.

Charlotte didn't answer. A thousand thoughts were going around in her head and not one of them seemed to be a suitable answer to her father's question.

"Who's this Reggie? You aren't planning some kinky threesome or something are you?" Betty interrupted their train of thought.

Reginald came out of his reverie.

"Come on Betty; back to the car," he grabbed Betty by the wrist and began to drag her out of the lounge room.

"You fucking stay put!" Reginald turned and pointed at his son.

Reginald refused to tell Betty who the pretty woman was laying on the couch and despite her protests he ushered her to his black BMW 733i.

"You drive this back to the railway station and leave the keys on the rear tyre. Get a train home," he opened the driver's side door.

Betty was amazed. Reginald never let anyone drive this car.

"What about the weekend in the country you promised me?" Betty whined.

"Get in the car you dozy bint. Drop off the car like I told you and catch a train to London and then get a minicab home," Reginald stuffed a twenty pound note in her hand and pushed her towards the car.

"Will you call me Reggie or will I see you next week at the office?" Betty grumbled as she climbed into the car.

"I'll call you if I can. I fly to Paris on Monday as you well know. Don't hurt my car; drive it carefully," Reginald slammed the door and leaned in the window to kiss Betty goodbye.

Reginald stormed back into the cottage, slamming the door closed on his way into the lounge room where Charlotte sat quietly sobbing with her head in her hands.