Finishing School For Young Ladies Ch1

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Finishing School For Young Ladies


Michele Nylons

Chapter One – The Beginning

Valerie Swindon sat at her desk in her small study grading exam papers. A shadow fell over the opaque glass panel of the door and she looked up at the ornate mantle clock and realised it was time.

She arose from her chair and came around to the front of her cluttered desk and unzipped her skirt. She caught it before it pooled around her ankles, stepped out of it and clipped it to a hanger and hung the hanger from a coathook at the top of the door. Hanging it there served two purposes, one it prevented her skirt from becoming wrinkled, and two it covered the opaque glass panel so prying eyes could not see inside her study.

Valerie leaned against the desk with her back to the door and when she heard it open she presented herself. She heard the door latch slide into place and the headmaster's feet on the threadbare carpet as he approached her from behind. The office was quiet and she could hear his breathing as he approached, the only other sound, the ticking of her mantle clock. The headmaster dropped some files on her cluttered desk and then she heard the ominous sound of his zip being undone and she pushed her behind up a little to assist him.

The headmaster smiled as he watched Valerie present herself for him. He dropped his pants and stepped out of them and improved his growing erection with his hand and moved in close behind her.

As always, she wore full cut panties, either nylon or satin, today they were red satin which contrasted nicely with the black suspender belt; she had sheer tan nylon stockings clipped to the garters. He traced the backseam of her stockings and caressed the gauzy welts. Valerie obligingly wriggled her buttocks for him. The headmaster pressed his erection into the crease of her buttocks, preseminal fluid was already dripping from the eye. Valerie pushed back for the headmaster, she knew he liked it when she rubbed her panty-clad buttocks against his erection and she also knew this would incite him to orgasm sooner so he would leave her alone and she could get back to work. The headmaster was usually in a rush and at this point he would pull down the waistband of her panties or just push the gusset aside and slide his cock into her.

But today he had time on his hands and he intended to use it.

He gripped the teacher around waist and indicated for her to stand. They never spoke during these encounters; they might sigh, pant, moan, groan and even utter words of encouragement, but there was never any conversation.

Valerie stood and sighed. It was going to be one of those afternoons was it?

He spun her around and looked his subordinate up and down. Her face was attractive but not what one would call beautiful. She had piercing green eyes accentuated by eyeliner and mascara, invariably black and heavy, pale blue eyeshadow accented with mauve accents, rouged cheeks and full red lips. Her highlighted brunette hair was parted in the middle and fell to the nape of her neck and her fringe rested level with her shaped eyebrows. A classic shiny bob.

Her neck was pale and slender, her shoulders wide, but her build was svelte, although she was getting a little ‘hippy’ as she got older. Her breasts were pert but compact, no more than a size B. She wore a cream silk blouse and the headmaster could make out the outline a red satin brassiere; she was fastidious about her bra matching her knickers. The black lacy suspender belt contrasted nicely with her knickers, the long garters snaked under her panties so she could remove them without unclasping her stockings.

The tan fully-fashioned stockings encasing her long legs showed off their shapeliness. As usual she wore four-inch black patent leather high-heels.

She had accessorised with silver jewellery but it was not gaudy. She took everything to the zenith of refinement without overstepping the mark.

The headmaster drank her in with his eyes and a filament of translucent preseminal fluid drooled from his glans.

He pulled Valerie to him and kissed her. He liked to kiss her because he knew she didn’t like to kiss him; but when her got her hot she couldn’t help but respond. He slid his tongue into her mouth and tasted her. As always she tasted sweet but with a scintilla of tobacco. He knew she brushed her teeth and used mouthwash after every cigarette.

She was stiff in his arms but he knew that wouldn’t last for long. One hand found her buttocks and caressed them through her satin knickers and the other snaked inside her blouse and caressed her pert breasts through her satin bra cups.

She sighed into his mouth and her knees buckled ever so slightly. He smiled.

He undid her blouse and eased her small firm breasts from their cups and a finger circled her areolae and flicked her small firm nipples. He lowered his mouth to her bosom and nuzzled on her teats, flicking his tongue across the sensitive little buds.

Her knees buckled a little more and a groan escaped the back of her throat and her hand went to his head and held his face to her breasts encouraging him to suckle.

She felt the headmaster’s penis push into her taut belly. His flesh was hot and throbbing, the eye leaking warm secretions on her flesh. She shuddered.

The headmaster reluctantly stopped attending to her breasts and kissed her again. He had some time in hand to enjoy her, but not as much as he would like.

He used one hand on her waist to pull her close and the other to caress her buttocks. This time she responded to his kiss and her tongue explored his mouth. She too was becoming eager.

The headmaster’s hand found the front of Valerie’s knickers and she groaned; she teasingly bit his lip.

Normally she would be gaffed with surgical tape but in anticipation of her appointed duties she had removed her gaff in the ladies lavatory earlier and used a thin panty-liner to hold herself in place.

Valerie was semi-tumescent and when the headmaster gripped the panty-liner and tossed it on the floor her penis sprang free and tented the front of her knickers. The headmaster gripped it through the slippery satin and squeezed.

This time Valerie’s legs quivered and she dropped to her knees on the threadbare carpet. This suited the headmaster as her face was lined up perfectly with his groin. He pushed forward and Valerie obliging opened her ruby-red lips to take what was offered.

She slavered at the headmaster’s purple glans, swallowing his preseminal leakage and flicked her tongue on his fraenulum. This time the headmaster groaned but he also grinned. He knew what she trying to do. She was trying to get him to ejaculate in her mouth but he was having none of that.

He allowed Valerie to fellate him, drawing her lips up and down his shaft and suckling his glans until he was ready.

The headmaster was a large man and particularly strong. He lifted Valerie to her feet and perched her on the edge of her desk in one fluid motion. He positioned himself between her spread legs.

Valerie was pre-lubricated in anticipation of her appointment with the headmaster but his cock was thick and meaty and she knew it would stretch her sphincter when he entered her. She exhaled and tried to relax.

The headmaster pulled the gusset of Valerie’s panties aside and positioned his glans against her puckered anus and pushed.

Valerie bit down on her hand to stifle her scream but when he was all the way in he stopped and allowed her to get used to his girth inside her. She relaxed a little more and then that same old special feeling began to propagate through her anus. The headmaster’s cock began to very slowly work away, sliding in and out of her, the sensitive nerves on her sphincter responded and his bulbous head pressed on her prostate. Her own cock throbbed.

The headmaster pulled her face to his and he kissed her and she kissed him back. She lifted her buttocks off the desk slightly so his cock could penetrate her fully and she gripped his shoulders and fucked him back.

They rutted like that, wrapped in each other’s arms, gasping and groaning, using each other’s bodies for pleasure. The headmaster felt her anal muscles grip his cock like a velvet glove and he pushed deep into her as she wriggled against him, ensuring his cock found her prostate.

They fucked each other hard; the ‘thwok, thwok, thwok’ sounds cleaving the silence of the study as his pelvis slammed into her buttocks.

The headmaster gripped Valerie’s buttocks and squeezed hard as he pressed against her and ejaculated deep inside her. She felt his hot semen filled her back passage and own orgasm erupted from her. Her penis quivered and she filled the front of her panties with her creamy issue.

Even in the throes of orgasm they were careful to keep their bodily fluids from staining their outer garments.

The headmaster fucked his teacher hard as he spent himself inside her; he kissed her ravenously and she returned his kisses with equal veracity. She locked her legs behind him and rubbed her nylon-clad calves against his back and held him close as the last of his spend discharged inside her. She clenched her buttocks and worked her anus to drain him.

They both panted and sighed as their lust, now sated, retired to that primeval place from whence it had came.

It was time for practicalities.

They had an unspoken ritual and this afternoon would be no different. Valerie’s long, elegant, blood-red fingernails scrambled for a handful of tissues which she gave to the headmaster. He slowly extracted his deflating penis from her and caught any offending droplets with the tissues. He wiped himself dry as Valerie took a handful of tissues for herself and dabbed at her sphincter. She shucked off her semen-soaked panties and dropped them into a drawer at the front of her desk. She reached into the drawer and extracted a fresh pair and having dabbed at herself again she stepped into and pulled up her fresh clean knickers. She picked up the panty-liner and pressed it in place knowing it would be needed to absorb the last few drops from her own penis and the trickle of semen that would flow from her anus.

The headmaster stepped into and pulled up his trousers and Valerie moved her skirt a fraction across the opaque window pane; seeing no movement outside in the corridor, she unclipped it and stepped into it. She buttoned and straightened her blouse and tucked it into her skirt.

The headmaster, ever the gentleman, zipped the back of Valerie’s skirt closed; it was after all the least he could do after fucking her.

He cleared his throat.

“I’ll see you at the staff meeting then Miss Swindon,” he said loud enough for anyone lurking in the corridor to hear.

“Yes, of course headmaster,” Valerie replied in her smoky voice that drove half of the faculty wild with lustful thoughts.

The headmaster unlatched the door and strode purposefully down the corridor looking very self-important, the files under his arm a symbol of his status.

Valerie allowed herself a wry smile. It was their Thursday ritual and a small price to pay for the life she led. She picked up her purse and tottered down the corridor to the ladies and sat in one of the cubicles. She smoked a cigarette while she allowed more of the headmasters emission to dribble into the bowl. The headmaster’s wife had stopped having sex with him years ago and Valerie was his only release other than masturbation and he always saved up a nice load for their weekly encounters.

She absentmindedly picked at a strand of cotton stitching on her blouse and began to daydream. She thought back to how this had all began…

At age sixteen William Styles was the unluckiest lad alive; twice orphaned, once at age two and now at age sixteen. He sat at the bottom of the stairs, the door to the staircase ajar, and listened to the couple from the welfare agency.

“He’s still a minor but he’s shit out of luck. No one adopts a sixteen year old; even getting him into a foster home will be difficult,” the male social worker said.

He was sitting in the overstuffed chair where William’s father, he never called him step-father, used to sit.

“He’s been left a shitload of money in inheritance, that might be a carrot for some punter out there. The kid can pay his way and the foster parents will likely get control or partial access to all that cash,” the plump female social worker in the miniskirt and ribbed tights replied.

“You know the kid’s a savant; very intelligent,” the male social worker stated.

“He looks weedy. In fact he looks downright effeminate with that long hair, pretty-boy face and skinny body,” the female social worker sipped a tumbler of William’s dad’s best scotch.

He hated that these two so called court-appointed ‘legal guardians’ that were in his house. The two people he considered to be his parents had been killed in a plane crash two days ago. William was at boarding school and when the headmaster called him in and gave him the news and he broke down and cried.

He was introduced to the two social workers, now his guardians, who had been assigned to look after him until after the funeral. Then, being a ward of the state, he would be put into a boys home until he was eighteen unless he was adopted or fostered.

He knew he wouldn’t stand a chance in the boys home. It was true what the two social workers said, he was weedy and effeminate. He hated sports and what where considered manly pursuits. He had recently developed a penchant for fashion design and considered himself a Mod. It was the sixties and Mods were mostly slim, androgynous types, with long hair, who drove scooters, wore fashionable clothes and considered themselves artistic. He even had both ears pierced and wore a small black ankh in each earlobe.

William was lucky that his parents had plenty of money and had sent him to a progressive school that encouraged those with artistic abilities and freedom of expression.

All that would change when he went into the boys home. He would be the recipient of repeated beatings, humiliation, and possibly be sexually abused by the other boys. He wasn’t stupid; he knew the types who were interred in those places.

The two social workers assigned to look after him had tried to paint his fate in the best light possible. He would be a ward of the state for a bit under two years until he turned eighteen, then he would be released and have access to a plump inheritance. Not a bad deal at all they had tried to explain to the broken-hearted youth who had just lost his parents.

The social workers had adjourned to the couch. William was upstairs asleep so why not have a bit of slap and tickle and help themselves to free drinks. The skinny man lay on top of the plump but pretty young woman and kissed her, rubbing his groin into hers and trying to get a free hand under her jumper. Her miniskirt was already rucked up around her waist but he wanted to play with those fat paps before he got down and busy with her hot moist twat.

But the woman was right. William was extremely intelligent and a savant; and he was already plotting a way to disappear and live his own life. He knew that if he just ran way that normally social services wouldn’t try too hard to find him; being sixteen he was hardly a child. But…and the big but, was that he stood to inherit three hundred thousand pounds, and that was a lot of money in nineteen sixty. That was incentive to find him!

William had made up his mind. He was not going to forgo his inheritance, but he was not going into a boys home of any description. He already had a plan. It was daring, it was complicated, it was dangerous, but it might just work.

During the last term break from his boarding school he had gone to stay with his only real friend, Stephen Milford, at his family’s estate in the Cotswolds. During his stay he had become friendly with Stephen’s older sister Emily who was home between semesters from Chelmsford Finishing School For Young Ladies.

Emily arrived at the stately home two days after William and Stephen. William watched her alight from the black taxi, her pleated grey skirt rode high on her thighs and revealed a glimpse of gauzy stocking-top and her tight blouse, with house tie of course, and fitted blazer, showed off her svelte figure and budding breasts. She held her vintage French-style topper on her head as she alighted from the cab, her black patent leather, low-heel, court shoes kicking up puffs of dust on the raked gravel drive.

William was instantly in love. Not with Emily herself, but with the ‘Madeline-like’ creature before him who reminded him of the children's books written and illustrated by Ludwig Bemelmans that he had pored over, despite being ridiculed and criticised because they were ‘girls books’.

On Sunday the house was quiet. The Milford family had all gone to church but being agnostic, William declined the offer to attend with them. He snuck into Emily’s bedroom and hunted around in her closet until he found her school uniform hanging in her wardrobe. He took it down and lay it on the bed and appraised it. He desperately wanted to try it on; not for any form of sexual gratification, he just loved the cut, the lines, and the fabric. And of course it was so ‘Madeline’.

He opened a couple of drawers and was instantly besotted with her lingerie. The cool, sleek feel of satin and nylon panties, the cute little cups of her matching brassieres, and oh my…those long, sensual stockings with gauzy welts, reinforced heels and toes, and fine dark backseams. Slippery satin full slips and petticoats that felt so sensuous and luxurious to his touch. He had to try them on.

He had watched his mother dress on many occasions so it was no mystery, but he soon found out it was an art.

He rolled up and stepped into a pair of stockings which felt so wonderful as he slipped them up his legs but of course he soon realised he needed to put on the suspender belt first so he could clip the welts of the stockings to the silver garters. Having achieved this he stepped into a pair of white satin full-cut panties and luxuriated in the feel of them as they slid against his nylons as he pulled them up and smoothed them into place. His penis was semi erect and tented the front of the panties.

He didn’t like that it spoiled the line of the garment and with some difficulty he managed to push his penis between his legs and hold it in place with the gusset of the knickers. He had to adjust the straps on the matching white satin bra so it would fit; and after a bit of wrangling he managed to get it on properly. Although the cups were small, Emily’s breasts were still just buds, his chest was flat and the cups remained forlornly empty.

The skirt fit quite nicely as did the blouse, although he had a little difficulty buttoning it up as it buttoned the opposite way to a man’s shirt. The blazer was a tight fit but he left it unbuttoned.

As hard as he tried he couldn’t squeeze into Emily’s school shoes, his feet were just a little too big. He rummaged around and found a pair of strappy sandals that he was able to squeeze his feet into but he didn’t like them at all. His fashion sense was displeased that they did not match the uniform ensemble.

He looked at himself in the mirror and was pleased with what he saw; his long light-brown hair was stylishly cut and with his androgynous looks he could easily pass for a girl dressed as he was, even without makeup. He had hardly any facial or body hair at all and his skin was soft and blemish free.

He twirled around and the pleated grey skirt rode high on his thighs exposing the welts of his stockings briefly. He saw Emily’s French topper hanging from a hook behind the door and perched it on his head. He adjusted it to a rakish angle and liked what he saw. He smiled to himself and thought he could probably pass as a ‘Saint Trinian’s’ girl. He giggled as the thought popped into his head.

The clothes felt so tight and luxurious against his sensitive skin; he was beginning to understand why some girls were so fastidious about how they dressed. The whole experience, dressing in Emily’s clothes while the family was away, was wonderful but was also quite dangerous.

He carefully placed everything back where he found it. He was worried that it wasn’t perfect and that Emily would find out but he convinced himself that he was just being paranoid.

When the Milford’s returned from church they found him sitting in the lounge drinking tea and reading the Sunday papers.

Stephen and Emily raced upstairs to change, he out of his dark suit and Emily out of her boring twin-set. Emily could sense something was wrong as soon as he opened the door to her room. Someone had had been snooping! She checked all her things and they were in order but she could sense subtle differences in how she had left various items. Her closet was closed but she always left it slightly ajar so that her clothes aired. A little flash of colour caught her eye. Her underwear drawer was closed on something and as she approached she saw a little red flag of satin knicker material caught in the drawer.

She opened the drawer and frowned. She rummaged around and found a pair of her stockings were bagged, someone had worn them recently and they hadn’t returned to their shape. She held up the pair of white satin knickers that William had worn and she could just make out the little stain on the front, leakage from his preseminal fluid no doubt.

She smiled. Her red lipsticked lips formed into an impish grin.

Although she never mentioned to William what she suspected, the two became very friendly. They discussed fashion, the latest bands, and teenage gossip. Chatting with William was like chatting with one of her girlfriends.

Stephen became jealous of the friendship that William and Emily were developing over that short week. In a fit of angst one day he lost his temper.

“You know what William? You might as well be a girl! You almost look like one and you’re certainly acting like one now!” Stephen bawled.

“I guess I’m off to ride bikes and find conkers to smash,” William smiled at Emily and soon made friends again with Stephen and went off to undertake boys pursuits.

If William was good at anything besides the arts it was diplomacy.

And…William was also good with money. His father had said that being a man of means meant being a man responsible for those means. He had kept William awake many a night explaining how to move money around between accounts here, and investments there, to minimise tax and to hide your wealth from those who would beg, borrow, sponge, and tithe.

“William my boy; keep one step ahead of the tax man and two steps ahead of your friends and family when it comes to money. Keep things simple but keep them slippery, if you know what I mean,” he winked and nodded at his young protégé.

William wasn’t naïve when it came to sex and he smiled when the male social worker finally pulled down the gusset of the chubby woman’s tights and entered her. She lifted her legs and wrapped those awful ribbed tights clad legs around the male social worker and encouraged him to fuck her.

It was the perfect opportunity for William and he flung a satchel bag over his shoulder, slowly opened the door at the bottom of the staircase and crawled on his hands and knees to the kitchen.

He cast one glance back and saw the man rutting away at the plump, pretty social worker and part of him hoped it would be worth it when they found out that he had made his escape. He was outside and gone before the social workers had finished fucking.

William had enough cash to take a taxi to an exclusive London hotel where the next day he entered one of the International Call phone booth’s in the lobby and made three calls. He had a small bankbook in his hand and piece of paper with three sequential number codes on them. Within half an hour William had moved one hundred thousand pounds from two accounts in the Virgin Isles to two accounts he set up in Grand Cayman.

He left the hotel and made his way to a commercial bank where he was able, for the appropriate recompense of course, to shift several thousand pounds from one of his Grand Cayman accounts into an account with the bank. He was provided with a passbook, a cheque book and more importantly a safe deposit box. He filled in the paperwork to allow joint access to his accounts and Safe deposit box to a Miss Valerie Swindon. He approached a teller and withdrew five thousand pounds in cash. Most of the cash went into the safe deposit box; he kept five hundred pounds on his person and returned to his hotel. He stopped at a stationer on the way back to the hotel.

All William needed now was a new identity and somewhere to lay low and he knew just the place. A place where no one would even think of looking for him.

William opened his satchel and pulled out a sheet of paper and closely examined it. It was a document that he stolen from Emily’s bedroom when he was staying with Stephen Milford. At the time he had no idea why he had taken it, it was a momento of sorts, but it also served, in his subconscious, to keep him close to Emily.

The letter was printed on stiff and expensive parchment with a gold embossed logo representing a stylised castle keep with a drawbridge and the words ‘Chelmsford Finishing School For Young Ladies’ printed in gold underneath. The contents of the letter were quite boring, a request for support for the annual picnic; but what William prized was the mailing address and the phone number of the school below the coat of arms.

He approached the concierge desk in the hotel and arranged for a business suite, of which the hotel had many, as well as conference and office facilities. The concierge had no concern about the youth hiring such facilities, he was paying cash and cash overrode any qualms the concierge had.

William sat at an electric type writer and wrote a letter on the fine paper he had purchased at the stationer. The letter was from the step-father of a Miss Valerie Swindon, a name he had made up on the spot when the whole idea came to him. He explained that he was a widower who travelled extensively for business and needed to place Valerie into a suitable boarding school. Mr Styles would pay for his step-daughter’s tutelage by cashier’s cheque annually and he would send Valerie any incidentals she needed.

Mr Styles would of course take his step-daughter Valerie home during the school breaks but his mining and prospecting company kept him away most of the year.

Attached were letters of recommendation from Valerie’s tutors and school reports from the other two schools she had attended.

It took William the rest of the day to write those reports on different stationery for each, and to make them look appropriately aged where necessary.

William had chain smoked a dozen Benson and Hedges while he worked and, assessing his voice was appropriately hoarse, he called the number for Chelmsford Finishing School For Young Ladies and asked for the Dean of Admissions, identifying himself as Mr William Styles, step-father of one Valerie Swindon. He was pleasantly surprised that the Dean was in and would take his call. He ploughed ahead with a rehearsed script explaining that he would be sending an application for his step-daughter to attend the school, along with a cashier’s cheque for her first year’s tuition and board.

Valerie would be able to attend an interview, if that was required, but unfortunately, he, Mr William Styles would not be able to attend as he had business in the Indonesia where a recently discovered large coal seam needed to be exploited.

The Dean harped on for few minutes about how the request was a little unusual but not unheard of; several of the girls at the school had parents living overseas. If Mr Styles could send through the application and letters of reference poste haste and Valerie Swindon herself was able to attend an interview next Monday he was sure that all would be in order.

What the Dean didn’t say was that most of the privileged gentry who sent their daughters to the Finishing School seldom paid a year’s subscription in advance, and often had to be repeatedly reminded that they were in arrears. The fact that Mr Styles was prepared to pay a year’s subscription up front was wonderful news indeed. Mr Styles inquired as to how much board and tutelage might be and was delighted to be informed that for an extra three hundred pounds a year his step-daughter could have a private room in the dormitory.

William now had a deadline to work to. He paid the concierge a healthy tip to ensure his letters were dispatched by courier to Chelmsford Finishing School For Young Ladies.

It was now time to go shopping. William’s penchant for fashion design would stand him in good stead but he had no idea how to go about selecting girls clothes, shoes and accessories in his size and how to dress properly and use makeup.

To William’s analytical brain there was a simple solution. Find someone who knew about such things to teach him.

First he went to a High Street department store and bought the biggest cosmetics case they had. The shop assistant assured him that it had everything a girl could need when it came to makeup. He stopped at an off-licence and paid a young lout who was old enough to buy liquor five quid to buy him two bottles of gin and five packs of fags. He dropped his purchases off at the hotel.

Then William took a taxi to Soho and sat drinking coffee and smoking cigarettes while watching the passing parade. He soon became attuned to the ebb and flow of the place. The pushers selling amphetamine tablets and baggies of weed, the touts luring tourists into the girly shows and of course the prossies displaying their wares, hoping to trap a punter.

He watched a pimp standing in an alley and approached him and after waving a couple of tenners in his face the pimp pointed out what William was looking for.

“Are you sure? I don’t believe it!” he asked the pimp incredulously.

“I’m sure! I’m fucking positive mate!” said the pimp snatching the tenners out of William’s fingers.

He watched the girl for about forty-five minutes before he approached her. She was mature but very attractive, and even after careful observation William wasn’t sure that the pimp was telling the truth.

Sally Macintosh had been a transvestite since she was seventeen and lived full time as a woman. Now in her thirties she was ‘on the game’ because no one would hire a ‘tranny’ in respectable employment. Besides the odd punter giving her a black eye now and then, it wasn’t a bad way to earn a quid she espoused as she looked around the grand hotel room that William had taken her to.

William explained what he wanted from her.

“So in a nutshell you want me to take you to buy clothes, shoes, lingerie and everything else you need to crossdress and then teach you how to become a transvestite?” she took one of William’s cigarettes from his packet on the table and lit it.

William nodded lighting one of his own.

“And for my time you will pay me one hundred pounds?” she smiled.

“Yep,” William replied.

“I get to stay here for two days and order room service and you supply the drinks and smokes?” Sally raised her eyebrow.

“Yep,” William blew smoke at the ceiling.

“Or. I’ll hit the streets and find another transvestite to teach me,” he grinned perniciously.

“Done! You give me half the cash up front and the rest after,” Sally grinned back at him.

Sally was slim and attractive. She wore heavy makeup and her bleach-blonde hair was styled so as to give her a fringe that came to eyebrow level and long, side-swept bangs. She wore a black, long-sleeved mini-dress that displayed her long, nylon-clad legs to advantage. Her skirt was so short that she had to be wearing pantyhose not stockings. She was wearing tasteful costume jewellery and carried an elegant black beaded purse. She could pass for an attractive mature woman anywhere. You would never guess that she was a transvestite unless you looked extremely close and even then you would have to have an inkling. She was just what William was looking for.

“Ok. Lets get started. Strip,” Sally smiled.

William stood naked before the prostitute and she inspected him closely.

“You’re very lucky; hardly a skerrick of hair on you, even on your face. We’ll just pluck the odd one or two that are there and you keep plucking and eventually you won’t have to,” Sally began.

“You’re slender too, but with nice wide hips and you have plump buttocks so you should pass ok and those long legs will look wonderful when we put some hosiery on them. Your feet are small which is good and we can do a lot with your hair,” she smiled.

“You sure you wanna do this?” she looked at him questioningly.

William nodded and smiled.

“I’d like to get started please,” he said.

“That is one huge fuck-off makeup case! You left nothing to chance did you?” Sally grinned.

“Sit down in front of that mirror and I’ll teach you all I know about makeup. After that, it’s down to practice, practice, practice,” Sally said and downed half her tumbler of gin and tonic.

Sally shaped William’s eyebrows with tweezers and manicure scissors.

“See how I’ve shaped them? Just keep them like that; it’s really easy,” she explained.

“Now I’m going to teach you how to put on makeup. It’s not hard but please pay attention. It’s more ritual than anything once you have the hang of it,” she explained,

Sally applied concealer, foundation, powder, rouge, eyeliner, eyeshadow, mascara and lipstick to William’s face, explaining what she was doing as she did it.

“Well, what do you think?” Sally smiled at William in the mirror as he examined himself.

William was astounded. He was looking at a beautiful young woman with smoky eye makeup, long black lashes, rouged cheeks and red lipstick. Her face was framed by silky straight brown hair.

There was no way the gorgeous creature looking back at him could be a William.

“Ok. Now it’s your turn. I want you do what I just did,” she took a packet of wipes and started to wipe away the makeup.

“It’ll take me ages to become as proficient as you,” William complained.

“Well you’ve got all night to practice. Tomorrow at ten we go shopping,” Sally grinned, pouring herself a liberal amount of gin.

To be continued….

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A strange beginning

but once I scrolled past all the sex, I found a pretty good plot starting to develop :)

We the willing, led by the unsure. Have been doing so much with so little for so long,
We are now qualified to do anything with nothing.

Strange indeed

It was a strange begining, but when I finished the chapter it made sense.

I came out after 10 years of secrecy of me being Transgender. I hope you do too, Hugs and Kisses, Call me Caitlin, or Caitie <3/strong>

Always hire a pro.

Interesting, hiring a transgender hooker to show him how to look and act like a teenage girl. Wonderful, I never would thought of that.


Not a clue

Jamie Lee's picture

Those two social workers are going to be beyond upset when they find out that William took a powder. And as usual they'll be looking for William as a sixteen-year-old boy. Never in a million years will they expect to look for a sixteen-year-old girl named Valerie Swindon, at a girls finishing school.

If they do find him/her they will be more shocked when they learn about the money they think they will steal from William. The only thing those two need is a feeding trough.

Others have feelings too.