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Finishing School For Young Ladies

Author: 

  • Michele Nylons

Organizational: 

  • Title Page

Audience Rating: 

  • EXPLICIT CONTENT
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Finishing School For Young Ladies

By

Michele Nylons

TG Themes: 

  • Disguises / On the Run / In Hiding
  • Fresh Start
  • School or College Life

TG Elements: 

  • Bad Girls / Promiscuity
  • Girls' School / School Girl
  • Identity Theft

Finishing School For Young Ladies Ch1

Author: 

  • Michele Nylons

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • EXPLICIT CONTENT

Publication: 

  • Serial Chapter

Genre: 

  • Transitioning

Character Age: 

  • Teenage or High School

TG Themes: 

  • Disguises / On the Run / In Hiding
  • Fresh Start
  • School or College Life

TG Elements: 

  • Bad Girls / Promiscuity
  • Girls' School / School Girl
  • Identity Theft

Permission: 

  • Posted by author(s)
Saint Trinians.jpg

Finishing School For Young Ladies

By

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….

Finishing School For Young Ladies Ch2

Author: 

  • Michele Nylons

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • EXPLICIT CONTENT

Publication: 

  • Serial Chapter

Genre: 

  • Transformations

Character Age: 

  • Teenage or High School

TG Themes: 

  • Disguises / On the Run / In Hiding
  • Fresh Start
  • School or College Life

TG Elements: 

  • Bad Girls / Promiscuity
  • Girls' School / School Girl
  • Identity Theft
  • Lesbians

Permission: 

  • Posted by author(s)
Saint Trinians.jpg

Finishing School For Young Ladies

By

Michele Nylons

Chapter Two – The Butterfly Emerges

“So why Valerie Swindon?” Sally asked, sipping a gin and tonic with her stocking feet up on the coffee table.

“It’s the first name that popped into my head so no one should associate it with anything to do with my past life,” William replied, also sipping a G and T and smoking a cigarette.

“That’s smart. A lot of trannies take on femme names that resemble their male names; Steven becomes Stephanie, Robert becomes Roberta, Michael becomes Michele, and so on.

“You really have mastered the art of makeup,” she smiled at him appreciatively.

“I like artistic stuff; and when I was staying with a friend a while ago, I found out through his sister that I liked feminine stuff too,” William appraised the glowing end of his cigarette.

“Did you ever try on your mother’s underwear or her clothes?” Sally smirked.

“Why would you ask that!” William was suddenly defensive.

“Don’t get angry babe. That’s how most of us trannies start out, trying on our mother’s or sister’s knickers and stockings. Slipping into a slip,” she giggled, the gin was taking effect.

“I told you. I’m not doing this because of any fetish or sex malarky; I’m doing it as a disguise,” William sounded enraged.

Sally snuggled up to him on the couch and he couldn’t but help notice her dress ride up to the very top of her thighs; the scent of her perfume was very alluring.

“You’re not angry with me are you honey,” she kissed his cheek teasingly.

William blushed.

“I told you there is no need for you to provide any intimate services,” he replied, reddening.

“But what are you going to do when those randy men come after you Valerie? I’ve seen how you look in makeup and when I get you dressed you’re going to look stunning,” she nibbled on his ear playfully.

William pushed her away.

“Don’t call me that until I am fully dressed. And I’m sure I will be able to deter any advances made on me in that way. I am not at all interested any of that perverted stuff. I might be dressed like a girl but I will still be a man,” he growled.

“Like me?” Sally laughed.

“Not like you! You’re…you’re…” William faltered.

“A tranny?” Sally smiled solicitously at him.

“You don’t find me attractive?” she leaned into him and slid her nylon-encased legs along his thigh and nuzzled his earlobe.

“Stop that! You’re drunk!” William blurted out and drained his own glass.

Sally blew in his ear and whispered.

“And so are you and I think you fancy the pants off me,” she raked her red fingernails across his fly where a thickening bulge was growing.

Sally leaned into William and offered her lips and he couldn’t resist. They kissed. At first tenderly and then their ardour grew. Sally put down her drink and offered William her complete attention. He might be effeminate but he was still handsome. She kissed him and snuggled up against him.

The hotel room was dark except for the lamplight, a haze of cigarette smoke hung from the ceiling. William had been drinking as heavily as Sally had and their defences were down. Sally snaked her slim body around William and he responded, kissing her passionately.

His hand slid up her thigh, the cool nylon of her pantyhose was scintillating to his touch. His hand slid under the hem of her dress and reached the top of her thighs; his fingers drifted across the front of her silky panties and he was surprised not to find a bulge. After all he knew Sally was a transvestite.

Sally’s fingers traced the outline of William’s erection in his tight jeans and then she squeezed his cock through the denim and he gasped in her mouth.

Williams fingers caressed the front of Sally’s panties and then drifted to her crotch. He found her penis there, hot and hard, taped between her legs. He pulled his hand away, shocked.

Sally kissed him harder and then bit his earlobe and whispered.

“What did you expect to find? You know I’m a tranny?” she moved her lips back to his and playfully bit his lip.

William returned his hand inside Sally’s dress and he tentatively stroked her through her knickers and pantyhose. He was actually quite delighted when she groaned and her penis became harder. He tore away her gaff.

Sally pulled down Williams fly and extracted his erect penis. Sally stroked and squeezed William’s cock while he kissed her and tentatively caressed her member.

Sally extracted herself from William’s embrace. She stood up and held out her hands and William arose from the couch. She unbuttoned and removed his shirt and then unbuckled his belt and helped him shuck off his jeans. His socks joined his shoes and he stood before her naked except for his briefs tented by a generous erection.

Sally reached into William’s underpants and grasped his hard cock and stroked it. She stepped into him and his erection pressed against her belly as she caressed his engorged penis. They kissed passionately and William undid the zip at the back of Sally’s dress and helped her out of it.

She stood before him; her small but well shaped breasts cupped in a lacy black brassiere, matching black lace panties over the gusset of her sheer-to-the-waist tan pantyhose. She kept on her high heels and she matched him in height. They kissed.

William pulled her body against his, enjoying the sensation of satin, lace and nylon against his sensitive skin. Sally pulled down his underpants so he was naked.

Sally led William to the bed and lay him out prone. She knelt over him and lowered her face to his crotch and engulfed his penis with her hot wet mouth.

William groaned. It was the first time he had been fellated and the feeling of Sally’s tongue on his penis was exquisite.

Sally scooted around on the bed so her groin was over William’s mouth while she continued to suckle him. He tentatively licked at her swollen penis through the layers of pantyhose and panty but he soon became frustrated. He pulled down her knickers and freed her erection from the sheer gusset of her pantyhose and took it in his mouth.

He was pleasantly surprised to find that it was quite a nice sensation. He mimicked everything that Sally did to his penis.

If she teased his fraenulum he did the same to her. If she sucked on his shaft and slavered his glans he did the same to her. If she tentatively explored his scrotum with the tip her tongue he did the same to her.

Sally was so excited; her young protégé was arousing her like he was a well versed lover. Her cock was leaking preseminal fluid which William gladly suckled and swallowed as she did the same to him.

But now Sally wanted something more. She wanted to feel like a real woman; the only way she knew.

Sally snaked underneath William so they were face to face again, kissing each other passionately.

She lifted her legs. Her pantyhose were already pulled down to her thighs and all she had to do was grasp William’s penis and guide it to her entrance.

He looked down at the gorgeous creature underneath him and she raised her nylon-sheathed legs and rubbed them on his flanks as he slowly entered her.

Sally was so tight, even though unbeknown to him she had pre-lubricated herself in anticipation of such an event, she was so tight that he was forced to take his time thrusting himself into her.

Sally gasped as William slowly entered her but she hung onto him and encouraged him by playfully biting his earlobes and lips, raising her buttocks off the bed to meet him, and rubbing her sheer-nyloned legs against his sensitive flanks.

When he was fully in her she kissed him passionately and began to fuck him. She wrapped her arms around his shoulders and her legs around his waist and lifted herself up to him and wriggled her bottom.

William groaned and kissed her. He dropped his hands to her hips and pushed her down into the bed and fucked her hard and fast. His climax was on him and he felt his spend ready to ejaculate.

Sally sensed it and pushed back against him and drove her tongue into his mouth. William felt Sally’s hard cock pressing against his flat belly, dribbling precum. He thrust hard and fast and emptied himself inside her, driving her down into the bed.

Sally screamed and rose to meet him as best she could, wrapping her arms around him and her nyloned legs drummed against him. She ejaculated against his tight stomach and sighed. It felt so wonderful.

William fucked Sally hard and fast until he was spent and exhausted and then he lay on top of her kissing her tenderly, stroking her hard nipples absentmindedly.

They kissed and stroked each other as their lust subsided into sensuality. Sally kept her silken-clad legs wrapped around William as she sensed he really liked the feeling of the gossamer fabric on his body. Their bellies were wet with Sally’s semen, and William’s spend was dribbling from Sally’s anus as his cock slowly deflated.

He looked down at her and smiled.

“Besides being a wonderful cosmetician you are quite the accomplished lover,” he grinned.

“For a young man, you are quite accomplished yourself. I am guessing there has been some tutelage?” she grinned up at him.

“A story for another day but that was totally amazing. So exciting and unconventional for me,” William beamed down at her.

“Yes. Imagine you are in my position,” Sally grinned up at him.

William’s face clouded over.

“I hardly think so!” he growled.

“Sure honey. Wait and see. Now turn out the light and cuddle up to me. I’m tired,” she kissed him on the cheek and manoeuvred into a spoon position.

William turned out the lamps from his bedside switchboard and snuggled up to Sally. He kissed her shoulder and then pulled the duvet over them.

“Goodnight princess,” he whispered.

Sally wriggled her buttocks against his goin and mewed. They were both asleep in minutes.

Sally woke to the feeling of William’s cock probing between her buttocks and she smiled. She reached back and guided his glans to her sphincter and relaxed so he could enter her. She was still lubricated from the previous evening’s lovemaking.

She pushed back against William as he slowly thrust in and out of her tight anus and she worked those internal muscles to grip his cock and encourage his orgasm. Sally enjoyed being fucked but felt no need to orgasm herself and let William enjoy fucking her as she writhed against him to encourage him. He took his time but she felt him come as her back passage became flooded with warm secretions.

She smiled and when William was sated she turned around and they kissed and cuddled.

After a while she reached for the bedside phone and ordered coffee from room service and sat up in bed and lit them both a cigarette.

“So?” William said.

“So what?” Sally grinned down at him and ruffled his hair.

“So does it feel as nice being the girl as it does being the boy?” he grinned up at her.

“Oh darling…it feels so much better,” she laughed.

The doorbell rang and Sally slipped into one of the hotel’s complimentary bath robes and let in the room attendant with the coffee. She tipped him a quid and gave him their breakfast order.

“No big a breakfast for you Miss Swindon. We’re getting you a wardrobe today and I want it to fit. But I’m having the full English,” she laughed and lit them both another cigarette and poured the coffee.

They had a delightful day out shopping; purchasing lingerie, shoes, jewellery, and perfume. Sally helped William try on skirts, blouses and dresses in the fitting room at Debenhams Department Store. William needed to go to his bank once again and make a substantial withdrawal, but he didn’t care. Sally was delightful and he had never felt so unreserved and unrestrained as he did in her company.

They had tea together at a stylish tea house and nattered away like old friends.

They stopped at an up-market hairdressers and had William’s hair styled into a classic bob with highlights. They both approved the coiffure and William tipped the hairdresser five quid.

William had an intrinsic sense of style and grace. Sally was impressed with his forethought and appreciation of what suited and fitted him. She could hardly wait to get him back to the hotel so she could make him up and dress him and reveal Valerie to world in all her splendour.

Later that afternoon, the hotel room bed, the couch, and the chairs were littered with shopping bags containing the purchases that the two had made.

Sally helped William change into a black, mid thigh, pencil skirt and mauve blouse. She showed him how to tuck and gaff and watched appreciatively while he slipped into a black lace garter belt, flesh-toned fully fashioned stockings, and a mauve satin panty and bra set.

Sally and William had discussed the issue of breasts. Valerie could either turn up to the interview flat-chested or with a stuffed brasserie. They both decided that it would not be too untoward for a girl of her age to be flat-chested and it presented the opportunity to use breastforms later on if she needed to show breast development.

Sally sent William to the bathroom to do his makeup.

“When you emerge. You will be Valerie Swindon. Your identity as a man will be forgotten for the foreseeable future. Do you understand?” Sally said solemnly.

William nodded and disappeared forever.

The creature that emerged from the bathroom was Valerie Swindon and she was gorgeous.

Valerie was delighted to find a bottle of Dom Perignon on ice when she emerged from the bathroom. Sally had ordered it to celebrate.

Sally gasped. She knew that her protégé would be passable but Valerie was stunning.

Valerie had paid attention to everything Sally had said to her. She placed her feet one in front of the other, toe down, then heel, and sashayed into the room.

Sally allowed Valerie some time to get used to walking in high heels and then she sat her down and they toasted with the champagne and had one last smoke before the biggest test of all.

“Just be confident out there darling; you look stunning so you’re going to attract attention. Your voice is very feminine, very smoky and seductive, so there is no reason for you to get clocked. Just think and act like a girl,” Sally said.

The girls set off down the corridor and into the elevator and through the lobby. Valerie flung a small leather handbag over her shoulder and they strutted down the street; two gorgeous girls confidant in themselves.

Valerie was a little apprehensive at first, even though she appeared outwardly confident. She was glad she had Sally with her to provide moral support but she knew that she would have to get comfortable being herself from now on; for two years at least.

After a while Valerie’s feet began to hurt.

“Walking in heels takes practice babe. Look, what about we stop in that pub over there and get a drink. It will also expose you to being a public place close to people,” Sally pointed to a pub across the road.

Sally and Valerie sat in a booth sipping gin and tonics, smoking cigarettes, and spent a pleasant hour turning away would be suitors.

“I told you men would try to get into your knickers. You are quite a stunner,” Sally smiled at Valerie.

“You know it’s so strange. I feel so feminine and I’m actually very flattered that men are finding me attractive. I didn’t think I’d feel like this,” Valerie sipped her drink through a straw, very ladylike.

“But don’t rush into anything. Allow yourself to get used to being feminine. You’re going to spend the next two years of your life as Valerie, take your time and enjoy the transition,” Sally reached across and took Valerie’s hand in hers.

“I owe you so much already,” Valerie leaned over the table and kissed Sally quickly on the lips.

“Hey! Are you two lezzies? What a fucking waste!” one of the more inebriated men who had come on to them yelled from the bar.

“And get used to idiots like him,” Sally smiled.

“I have really enjoyed today and especially enjoyed being out with you. But now I want to go back to the hotel,” Valerie finished her drink.

Sally looked a little disappointed. Today was her last day with Valerie and she really liked this young tranny.

They walked back to hotel, pretty much in silence. Valerie kicked off her heels and poured drinks. She turned around to see Sally picking up the meagre belongings she had arrived with.

“What are you doing?” the concern evident in Valerie’s voice.

Sally hid her face from Valerie to disguise her sadness.

“Two days Valerie. That’s what you wanted. Well two days are up and there is nothing more I can teach you. The rest is just down to experience and will come with time,” Sally wiped a tear from her face and stuffed some underwear into a carry bag, her back to Valerie.

Valerie strode over to Sally on stockinged feet and spun her around. She searched Sally’s eyes.

“Do you want to go?”

“Of course not,” Sally grimaced.

“Then don’t. Stay with me until my interview,” Valerie pulled Sally into her arms and kissed her.

It was so sensual; their soft lipsticked lips pressed together gently at first and then Sally parted her lips and Valerie parted hers and used her tongue to explore Sally’s sweet mouth. Valerie held Sally in a firm embrace, she inhaled Sally’s perfume and kissed her passionately. This was different to before. Valerie was very conscious and appreciative of the feel of her soft silky lingerie and stockings. She felt so feminine but she was acutely aware of Sally’s femininity as well.

It was strange but sensual, licentious, and lascivious…downright naughty!

They fell on the bed, Valerie straddling Sally. They kissed lovingly but lustfully and Valerie slid her hand under Sally’s skirt and went exploring inside her panties. She removed the tape from Sally’s gaff and squeezed her thickening erection. Sally reciprocated and stroked Valerie’s erect phallus through her silky panties.

The two lovers broke apart for a few seconds to shuck out of their skirts and blouses and then fell on each other again lustfully, kissing and rubbing against each other and squeezing hard cocks through satin panties.

Both cocks became unencumbered from their knickers and they rubbed them together, Valerie straddling Sally.

“Oh my! I seem to have awoken the unconscious slut inside of you,” Sally giggled.

“Oh daring. I have never felt anything so amazing as this,” Valerie moaned with lust.

Valerie lowered her face to Sally’s groin and suckled her erect penis. Sally simpered and held Valerie's head and guided her mouth up and down on her cock.

Valerie slavered at Sally’s tumescent member, flicking her tongue along the sensitive fraenulum and using her lipsticked lips to suckle on the shaft.

“Oh god you’re good at that darling,” Sally whimpered.

Valerie wriggled and squirmed and was able to get underneath Sally. Sally straddled Valerie, kissing her and rubbing their cocks together.

Valerie reached between their bodies and positioned Sally’s cock at the entrance to her anus.

Sally froze.

“Oh no darling. I don’t think you are ready for that yet,” she stroked Valerie’s face affectionately.

Valerie smiled up at Sally and suddenly gripped Sally’s hips and drove her lower body upwards, impaling herself on Sally’s cock.

At first the pain was excruciating and Valerie screamed out in agony.

“Oh no darling! I’m sorry,” Sally mewed and pulled her penis from inside Valerie’s sphincter.

“You didn’t do anything. I did it,” Valerie smiled up at her.

“And I want it. I really want it,” Valerie begged.

Sally reached over to the nightstand and snatched her purse and took out a tube of KY jelly and slathered it on her penis and rubbed it into Valerie’s little winkle.

“Let me do it nice and slow and you tell me to stop if it hurts. You’re supposed to enjoy this, not get hurt,” Sally said and kissed Valerie on the lips.

She lifted Valerie’s legs and put them over her shoulder. She kissed Valerie’s stockinged calves and smiled down at her lover.

“This is the best way,” Sally smiled and pushed forward slowly.

The tip of Sally’s penis slid inside Valerie’s sphincter and Valerie grimaced but held Sally by the hips and encouraged her. They kissed and Sally slowly filled Valerie’s virgin back passage with her lubricated cock.

Valerie felt full and a little wounded but Sally just kept still and kissed her lover so that Valerie could get used to having a penis inside her. Valerie felt the first stirring of lust inside her and gently pushed back against Sally. Sally smiled and eased herself out of Valerie a little and then pushed herself back in.

Valerie felt the beginning of tenderness in her prostate which slowly spread and became intensely pleasurable. She wanted Sally to rub against it and she began to lift her bottom up and thrust against Sally, encouraging her to fuck her.

Sally obliged and slowly began to fuck Valerie. Valerie lowered her legs and rubbed her stocking-clad calves against Sally’s flanks and she fucked her back. The two pretty transvestites fucked and writhed and moaned and groaned. Sally felt her orgasm approaching and she fucked Valerie harder and faster, she reached for Valerie’s cock and stroked it in time to her thrusts.

“Oh god! Oh god! I’m coming!” Sally shrieked and her cock exploded deep inside Valerie, pushing hard against her prostate.

“Oh god! Me too! Oh I love you!” Valerie screamed and her cock spasmed as Sally stroked and squeezed it.

Valerie’s semen sprayed everywhere as she writhed underneath Sally. The feeling from her penis was exquisite but the intense sensations radiating from deep in her anus was deliciously ethereal. Valerie cried, her passion was so intense. Sally kissed her and stroked her lover’s face.

Later they lay in each other’s arms tenderly kissing each other. Sally extracted herself, got up wrapped in a sheet and poured them both a drink and bought cigarettes and an ashtray over to the bed. She kissed Valerie on the side of the mouth and gave her a drink and a cigarette.

They sat up leaning against each other dressed only in knickers and stockings.

“You certainly don’t do things by half do you honey?” Sally stroked Valerie's shoulder.

Valerie smiled.

“Two days ago you bought a cosmetics case and today you’re a full-throttle tranny, fucking like a cheap hooker,” Sally giggled.

“Oh you bitch!” Valerie punched Sally playfully in the arm.

Sally put down her cigarette and began to wrestle with Valerie and before long they were making love again.

They slept soundly that night and spent the next morning taking breakfast in bed; Valerie continued to grill Sally about all things feminine and Sally explained to Valerie some of the more intimate and less glamorous chores that trannies undertake such as douching, tucking, and gaffing.

Valerie and Sally spent two more days together giving Valerie plenty of time to try on all of her purchases and to mix and match the outfits and accessories. Being artistic and fashion savvy, Valerie had an excellent sense of style and Sally soon became redundant as a fashion advisor but she still provided advice to Valerie about how to carry herself, how to walk, how to talk and how to project a feminine persona at all times.

They spent most of the days out and about in the city, exposing Valerie to being out in public where she became more relaxed and comfortable in her female identity. Valerie did a little more work with her bank in Grand Cayman, transferring more funds to the Commercial Bank of London. Being the nineteen seventies online banking was still decades away but wire transfers of funds, security deposit boxes, and phone banking using numerical code verification were all accepted practices for moving money around, which Valerie was able to do without presenting herself as William Styles.

The evening before Valerie needed to present herself to the Dean of Admissions at Chelmsford Finishing School For Young Ladies, the two transvestites tenderly made love to each other and fell asleep in each other’s arms.

They had done everything they could to prepare Valerie for her interview.

To be contined

Your honest comments, encouraging or scathing are very much appreciated

Finishing School For Young Ladies Ch3

Author: 

  • Michele Nylons

Audience Rating: 

  • Adult Oriented (r21/a)

Publication: 

  • Serial Chapter

Genre: 

  • Transformations

Character Age: 

  • Teenage or High School

TG Themes: 

  • Disguises / On the Run / In Hiding
  • Fresh Start
  • School or College Life

TG Elements: 

  • Bad Girls / Promiscuity
  • Girls' School / School Girl
  • Panties / Girdles
  • Shopping

Permission: 

  • Posted by author(s)
Saint Trinians.jpg

Finishing School For Young Ladies

By

Michele Nylons

Chapter Three – The Interview

“So Valerie Swindon? Are you ready” Sally asked.

Sally was still dressed in her bathrobe sitting at the coffee table in Valerie’s expensive hotel room, sipping coffee and smoking.

“You definitely not coming with me,” Valerie pouted.

“Yes! That’s the look! Use that on the Dean,” Sally teased.

“Come on Valerie; you need to do this on your own. You’re going to live in that joint for the best part of two years so present yourself as fresh, intelligent, artsy, confident, and with just a smidgen of sex appeal,” Sally said.

Valerie smiled pessimistically. She had been out and about with Sally for nearly a week and was comfortable in her skin and had had dealings with shop assistants, bar staff, waiters and members of the general public. But today she would be alone. In a room. With a man.

“How do I look?” Valerie spun on her heels so that Sally could appraise her.

They had given considerable thought as to how Valerie should dress. When glammed up to the nines she could pass for a young lady of twenty or even older and she looked quite the seductress. That look was definitely not what was required today.

They had settled on a navy blue pleated A-line skirt with the hem resting mid-thigh, a white nylon long-sleeved blouse, and a navy blue blazer that hung to her hips. The ensemble was similar to the uniform worn by the girls at the Finishing School. Her classic brunette bob with subtle highlights was blunt cut just above her shoulders, centre parted, with a fringe that rested on her eyebrows. It shone in the lamplight having been shampooed, conditioned, and given the obligatory one hundred brush strokes.

Shoes were kept simple. The Finishing School uniform prescribed black low-heeled courts but Valerie had decided on a pair of wedge-heeled Mary Jane’s with the strap over the instep. White semi-opaque tights complimented both her skirt and her shoes and showed her coltish shapely long legs to advantage.

She accessorised sparingly with a silver necklace, bracelet, earrings and a ring on the ring finger of each hand. A simple black leather-banded watch was affixed to her right wrist. Her makeup was subdued, some foundation, powder, a dab of rouge, a sparing amount of eyeliner and eyeshadow but plenty of mascara. Her pink lipstick matched her nailpolish. She had completed the ensemble with a subtle splash of perfume.

Valerie was wearing practical underwear, white satin full-cut panties that she called ‘granny knickers’ and a lightly padded white lace bra that gave her chest the very slightest of shape.

She didn’t want to look like a schoolgirl but she didn’t want turn up looking like a strumpet either; both she and Sally agreed the outfit was a nice compromise.

“You look gorgeous darling,” Sally arose and embraced Valerie, kissing her on the side of the mouth so as not to spoil her lipstick.

“Remember what I said. No smoking, not before the interview anyway, you don’t want him smelling smoke on you. Sip a little mouthwash before you go in. Pull down and straighten your skirt when you sit, cross your ankles and…”

Valerie laughed and pulled Sally to her and kissed her.

“Shut up! You sound like my mom not my lover,” she smiled into Sally’s glistening eyes.

“Is that what I am to you? Your lover?” Sally stared longingly into Sally’s eyes.

“What do you think you are?” Valerie looked confused.

“Your prossie? Your harlot? Your whore?” she looked down at her feet.

Valerie lifted Sally’s chin and shook her head.

“All the wrong words.”

“My lover. My confidant. My best friend,” she smiled into Sally’s face and kissed her lightly.

Sally smiled back.

“Wait for me Sally. I want to tell you how I performed at the interview. And I have an offer for you,” Valerie said.

Valerie scratched around, throwing her cigarettes, lighter, purse, change of tights – just in case she laddered them, and the spare hotel room key, into her classic black leather handbag.

Valerie splashed out on a taxi to take her to the Chelmsford Finishing School For Young Ladies. She sat on the back seat concentrating on getting her story right. She had rehearsed it time and time again with Sally and it was mostly based on fact but it was the little details she needed to get right. She did not want to get caught in a lie.

The more she focussed on her interview the less she concentrated on behaving like a lady; she was getting better, but it was not yet instinctive.

It was only when she became aware that the cabbie was staring at her in the mirror that she realised she was sitting with her legs wide open, her skirt had ridden up and the crotch of her white knickers was prominently displayed for all to see.

She saw the look of alarm on the cabby’s face when she caught him perving and she tormented him by opening her legs wide, rubbing her crotch and sticking out her tongue at him. He blushed a deep red and his eyes shot to the road in front of him. Valerie laughed to herself but also scolded herself for not concentrating on being a full time lady.

The cabbie did not get a tip.

Valerie was dying for a cigarette but it would have to wait. She smoothed out her skirt and patted her hair and took in the façade of the old but elegant building. It was red brick with slate tiles on the roof and white framed windows in rows delineating the four floors. Extensive gardens surrounded the building. Emily Milford had described to her the playing fields, botanical garden, and small wood at rear of the school. Wide stone steps led from the sweeping gravelled driveway to large wooden double-doors which opened to the entrance foyer.

Valerie watched the young ladies in the school’s uniform skip up and down the worn sandstone steps and the serious faced faculty members carrying briefcases and bundles of files in their arms. A bell sounded and almost at once the place seemed deserted. School was obviously in session.

Valerie rummaged in her bag and found small bottles of perfume and mouthwash. She gargled and swallowed, wincing at the bite of the mouthwash, and then sprayed herself liberally with perfume.

She took a deep breath and climbed the steps and entered the foreboding entrance hall with its high ceilings, tall narrow stained glass windows, imposing portraits of persons long passed on, crossed flags of the Union Jack and the school banner. There was even a suit of armour in one corner. Wide staircases with wooden balustrades led from either side of the entrance hall to the first floor from were she could hear mutterings which she presumed was the teachers and professors lecturing their students.

The two floors above the school rooms were the dormitories The ground floor consisted of the teachers studies, a library, administration offices, a kitchen and the cafeteria.

Valerie saw a wooden plaque hung on a shingle above one of the doors with the words ‘Dean of Admissions’ embossed in faded gold lettering. Everything about the school seemed at little old and worn; like it had seen better days.

Valerie approached the door and knocked gently.

“Come,” a gruff voice behind the door commanded.

Valerie entered the gloomy office and closed the door behind her. A mole-like older man with hunched shoulders and wire-framed glasses perched on the edge of his nose looked Valerie up and down. He was dressed in a black, billowing, professor’s gown, the sleeves of his shirt protruding from the slit sides had sliver metal sleeve-garters to keep the cuffs from falling onto his hands.

There were piles of books and files on the Dean’s desk and dust motes drifted in the air, a beam of wintry light managed to percolate through the sooty windows.

“Sit, sit, sit,” the Dean pointed to a wooden chair positioned in front of his desk.

Valerie sat down on the hard chair, carefully smoothing her skirt under her and arranging it modestly, closing her knees and crossing her ankles. She set her handbag on the floor beside her and gave the Dean her full attention.

“Your stepfather is William Styles,” the Dean began without preamble.

Valerie nodded.

“Speak up girl! Speak up!” the Dean admonished her.

“Yes, but I just refer to him as my father,” Valerie blushed.

“Hmm…commendable, commendable.”

Valerie very soon realised that the Dean of Admissions, who was also the head of the English and History Departments, was a blatherer who constantly repeated himself.

The Dean was head down studying documents which she recognised as the letters of recommendation from tutors who did not exist and school reports from two schools she had never attended. They were the documents she herself had forged. Now would come the moment of truth.

“Mmm…you appear to be a fine student and come highly recommended. Your father has paid your tuition and board for one year in advance and paid extra for a private dorm. Your father must love you very much,” he looked up and blinked at her myopically.

“Oh he does Dean. I just wished I saw more of him but with mother gone, and he required to travel extensively for work, my only option is boarding school and yours comes highly recommended,” Valerie smiled.

“Mmm…I see, I see,” the Dean nodded his head.

“As you are likely aware and as I explained to your father, Chelmsford Finishing School for Young Ladies is now more of a liberal arts college than a traditional Finishing School per se. Our curriculum is preparatory for young ladies designing on a career in the arts, rather than those seeking academic achievement,” he explained.

Valerie was about to nod when she realised her mistake and answered verbally.

“Just what I’m looking for Dean,” she smiled.

“Our syllabus is eclectic and quite liberal and well as ‘the three Rs’ includes: music, literature and the fine arts, practical beauty and deportment, fashion design and styling, grooming and etiquette, communication and job interview skills. We are a preparatory school of some prominence,” he said proudly.

“Which is why I would love to attend,” Valerie gave him her biggest smile.

“Consider yourself enrolled. I’m Dean Jenkins by the way and very pleased to meet you,” he extended his hand across the desk and Valerie shook it with ladylike charm.

There were some documents requiring her signature, one of which was the school’s Code of Conduct, which Dean Jenkins gave her to take away, read and sign. He explained to her that as she was joining mid term, a senior girl would be assigned to her as a mentor and chaperone. Valerie had two days to prepare herself and was to report to the school on Wednesday in uniform and with all her possessions.

Valerie made a point of thanking the Dean for accepting her application without being pretentious or fawning.

As soon as she was in the taxi heading back to her hotel she lit a cigarette and grinned to herself.

“Yes! Yes! Yes!” she punched the air.

The taxi driver looked at her in the mirror and smiled.

“You got in then I take it?” he grinned, assuming rightly she had attended an enrolment interview.

Valerie nodded at him and smiled.

“I’d let you into any school I was in charge of,” he winkled at her and chuckled.

“Cheeky,” Valerie grinned back but she hitched up her skirt and gave him a tasteful glimpse of knicker as a reward.

Valerie burst through the door of her hotel room and flung her handbag on the couch; she looked around excitedly and saw Sally lying on the bed in a redolent pose dressed only in black stockings and suspenders, red satin and lace knickers, matching bra and black highheels. Her makeup was heavy and alluring and she was sipping a flute of chilled champagne with another glass on the opposite bedside table waiting for Valerie.

She beamed at Valerie and patted the bed beside her. Valerie slipped out of her blazer, skirt and blouse and leapt on the bed beside her lover. She scooped up her glass of champagne and clinked glasses with Sally and downed the contents in one gulp.

She dropped the glass on the carpeted floor and leapt on Sally who squealed with delight and wrapped her arms around Valerie.

They kissed for what seemed like an eternity.

Valerie pushed her groin into Sally’s and their cocks rubbed together through layers of satin and nylon. Sally pulled down Valerie’s knickers and reached into her tights to find her erect and leaking precum.

“Mmm, someone is ready,” Sally beamed up at her lover.

Valerie pulled the gusset of Sally’s panties aside and pressed her glans into Sally’s sphincter. She could feel the slick lubricant and she pressed forward and slowly entered her lover.

“Mmm and someone else is ready too,” Valerie cooed and ground her pubis into Sally’s groin.

Sally encouraged Valerie to lie down on her back so that she could straddle her; this way Valerie’s cock was buried deep inside Sally’s anus and she could ride up and down on it controlling the tempo. Valerie gripped Sally’s hips and guided Sally up and down on her hard cock, driving herself deep into her lover.

Sally threw back her head and groaned, she loved being impaled on Valerie’s hard, long, thick cock and she wriggled her buttocks to get Valerie’s shaft rubbing on her prostate.

“Oh my god you are in me so deep!” Sally moaned, writhing on Valerie’s turgid member.

“Fuck me you bitch! Fuck me hard!”

Valerie lifted her buttocks off the bed to thrust into Sally as deep as she could go. She grasped Sally’s cock and caressed it. She felt it pulsate in her fingers and Sally ejaculated hot semen all over Valerie’s belly.

This invoked Valerie’s orgasm and she pulled Sally down on her pulsing cock and drove it deep inside Sally as her cock spasmed, filling Sally’s anus with her seed.

Sally writhed and wriggled on Valerie’s cock, spraying her spend as she came and Valerie held onto Sally’s hips and followed her gyrations with her groin as her own ejaculate filled her lover’s back passage.

The two transvestites gasped and shuddered and spent themselves and then Sally fell forward and they kissed and caressed as Valerie’s cock slowly deflated inside Sally’s behind.

Sally climbed off and they lay side by side kissing and stroking each other.

Valerie disengaged after a while and poured them more champagne and lit them both cigarettes.

“So I’m guessing the way you just jumped on me and shagged me that you had a successful interview,” Sally laughed.

“I report to the school on Wednesday for indoctrination,” Valerie grinned.

“You were never in doubt honey,” Sally kissed Valerie quickly on the lips.

“So what’s this offer you have for me?” Sally leaned on one elbow and looked at Valerie quizzically.

“Well you know I’m a woman of means,” Valerie lazily stroked Sally’s thigh.

“Well yeah. You spending up big time on clothes, on this hotel room, on everything,” Sally replied.

“And on you,” Valerie sniggered.

“Hey honey; you know I can’t accept any more money from you; I’ve had a great time this week at your expense,” Sally stroked Valerie’s face.

“Hey I’m offering you a business venture babe not charity,” Valerie countered.

“So you know I have some money. I have a lot more than you might think and I have this idea. I buy a nice apartment close to London. Somewhere where nice you can work out of instead of walking the streets,” Valerie started.

“Oh no Valerie I couldn’t possibly accept,” Sally interrupted.

“Hey let me finish darling. This is no free ride. You work out of the apartment and we split the proceeds. And when I get breaks and holidays from school I come stay with you,” Valerie grinned.

“Oh Valerie that is just too generous. But isn’t there someone else you would rather stay with?” Sally looked at Valerie soberly.

“Darling there is no one else I would rather spend my time away from school with than you. I think…well…I think I’m falling in love with you, just a little,” Valerie smiled down at Sally.

Sally reached up and pulled Valerie’s face to hers and they kissed. And they caressed. And they fondled. And they nuzzled…and of course they made love.

Finding Sally an apartment was not as difficult as they thought it might be; especially when the two delightful creatures turned on the charm with their selected real estate agent but more especially when cash was offered.

They bought a recently renovated three bedroom two bathroom apartment for twenty thousand pounds on the outskirts of Soho. Not right in the heart of the red light district, but close enough to ensure Sally a ready supply of punters. The flat was put in Sally’s name for obvious reasons and they spent a fun filled day picking out the furniture.

Valerie made an appointment with Mrs Delaney’s Couturier and Haberdasher, the dressmaker and couturier who was appointed to provide school uniforms for the women and girls who attended the Chelmsford Finishing School for Young Ladies.

Sally had gone to great lengths to teach Valerie how to tuck and gaff properly. It would be so important when she interacted with the other girls at the school; and today would be Valerie’s first time undressed in front of someone besides Sally.

Sally showed Valerie how to push her testes up inside herself and then push her penis back between her legs, pulling the scrotal skin up on either side. She then gaffed with surgical tape which gave her a flush mound; she could even sit on the toilet and urinate just like a woman. When she pulled on and smoothed her knickers it looked like she had a pubis just like any woman.

So Valerie gaffed and pulled on her ‘granny knickers’ matching padded bra and, having dressed in the same outfit that she wore her interview, they took a cab to Mrs Delaney’s Couturier and Haberdasher, located on the High Street in Chelmsford.

Pauline Delaney herself attended to Valerie in a private fitting room. As Valerie’s was a rush job, Pauline found some completed pieces and helped Valerie try them on, promising to take her measurements and provide her with tailored uniforms for the next semester.

Valerie sat on a padded stool, stripped down to her knickers, tights and brassiere.

“You’ll have to take off the tights sweetheart; the Finishing School is one of the few places left that mandates stockings as part of their uniform.”

“You’ve read the code of conduct I take it?” Pauline asked.

“Yes I have. I think it goes something like this: ‘Hosiery: sheer tights may be worn in place of stockings after school tuition hours and on weekends but stockings only are to be worn when in uniform in public’. I think that’s rather archaic,” Valerie commented.

She realised her mistake as she watched Pauline’s face redden with anger.

“That’s the problem with young women these days. They want everything to be easy and not have to pay attention to detail. It’s so simple to pull on a pair of sheer tights or pantyhose as our American cousins call them, but the ritual of snapping welts to garters, smoothing out wrinkles and straightening seams is character building. It requires patience and attention to detail. And that is why stockings are still the mandated hosiery for Chelmsford Finishing School for Young Ladies,” she scolded.

Valerie actually quite liked the feel, fit, and style of fully-fashioned stockings and was not about to get into an argument about hosiery with Pauline.

Her issue was that she liked to wear her knickers over the gusset of her tights as it helped keep her gaff in place and it also looked neater.

“Then may I have a little privacy while I remove my tights?” Valerie asked sweetly.

Pauline obliged; she didn’t want to be in same room as lady removing her knickers.

“Of course dear; I’ll be back with some items for you to try on in a jiff,” she smiled, her tirade over.

Valerie whipped off her knickers, pulled down her tights and put her knickers back on. She was pleased with her gaff and confident Pauline wouldn’t have an inkling that she was not a real woman.

The rest of the fitting went well. Pauline fitted her with a black garter belt to which she helped her clip the welts of the grey, fully-fashioned stockings, as approved by the school.

“Put the garters under you knickers dear, then you can pull your knickers down when you need to tinkle without removing your stockings,” Pauline tittered.

‘Tinkle or fuck,’ Valerie thought to herself and smiled.

Pauline helped her step into a pleated grey skirt, the hem of which sat high on her thighs, and fitted her into a white cotton blouse to which she helped Valerie affix the school tie.

“When you get assigned to your house, you can wear the house tie dear,” Pauline explained needlessly, but Valerie just smiled and tucked the blouse into her skirt and zipped her skirt closed.

She tried on several pairs of shoes until she found a pair that fitted her perfectly. The black patent leather, low-heeled court shoes looked quite nice with the uniform ensemble. They found a blazer with the school’s crest and motto embroidered on the pocket and she was nearly done.

The final accoutrement was the vintage French-style straw topper. Pauline placed it on Valerie's head and lead her over to the full-length mirror.

Valerie loved it!

“Wow!” she squealed.

“Yes the uniform is very lady-like. And if I may say so…a little bit cheeky in this day and age,” Pauline grinned.

“Sort of Saint Trinian’s,” Valerie beamed.

Pauline grinned at her.

“If you say so dear; but I’ll never admit to agreeing with you in public,” Pauline winked at her conspiratorially.

“Now that I know what fits you I’ll put together two skirts, three blouses, one tie, one topper, one pair of school shoes, one blazer, the sussie belt and five pairs of stockings. I take it you will buy your own knickers and bra; just buy the same ones you wore today dear. They are acceptable,” Pauline said.

“Perfect but can I show my friend before I take the uniform off?” Valerie beamed.

“Of course dear. I actually thought she was your mum,” Pauline sniffed.

Valerie emerged from the fitting room and posed for Sally.

“Oh my god look at you!” Sally grinned.

“You look wonderful…and very schoolgirl like,” she smirked.

Sally pulled Valerie close and hugged her and then jovially pinched her bum.

She kissed Valerie’s ear and then naughtily bit her earlobe.

“I can’t want to shag you in that outfit,” she whispered and squeezed Valerie's bum.

Pauline Delaney cleared her throat and gave them both a disparaging look.

“Ahem…cash or cheque?” she asked.

To be continued.

Finishing School For Young Ladies Ch4

Author: 

  • Michele Nylons

Caution: 

  • CAUTION: Rape / Sexual Assault

Audience Rating: 

  • EXPLICIT CONTENT

Publication: 

  • Serial Chapter

Genre: 

  • Transitioning

Character Age: 

  • Teenage or High School

TG Themes: 

  • Reluctant
  • Disguises / On the Run / In Hiding
  • School or College Life

TG Elements: 

  • Bad Girls / Promiscuity
  • Girls' School / School Girl
  • Lesbians
  • Panties / Girdles

Permission: 

  • Posted by author(s)
Saint Trinians.jpg

Finishing School For Young Ladies

By

Michele Nylons

Chapter Four – The New School

An elegantly dressed slim woman in her forties stood at the top of the stone steps leading up to the wide wooden double door at the entrance to Chelmsford Finishing School For Young Ladies. She was smiling and Valerie smiled back at her.

“Welcome Miss Swindon. I’m Deputy Headmistress Lisa Meakins” she beamed.

“Harry go down to the kerb and see Miss Swindon’s cases to her dorm please,” Lisa instructed the rather decrepit looking man in the dirty trousers, frayed shirt and old duster.

“Harry Cartwright is our caretaker, gardener and porter. We used to have one of each but we have to make do with what we can afford nowadays,” she turned down her mouth briefly.

“Anyway, come to my office,” Lisa indicated the way with an open hand.

“You’ve read and signed our Code of Conduct I take it and I can see you have met our uniform requirements. I must say you look rather smart,” the Deputy Headmistress opened the door to her office.

The Deputy Headmistress’s office was a lot brighter and cleaner than Dean Jenkins’ and the furniture was in better condition. A padded seat sat facing Lisa Meakins’ desk and she indicated for Valerie to sit in it.

Valerie smoothed her skirt under her, closed her knees and crossed her ankles, all without thinking. Being a lady was starting to become second nature. She rested her topper on her knees.

“Your paperwork please,” Miss Meakins held out her hand, her nails were manicured and painted with bright red nailpolish.

Valerie reached into her handbag and withdrew the Code of Conduct which she had signed. Then she handed over her tenancy agreement, which she had also signed, and a copy of a letter authorising Valerie to be able to reside with a Miss Sally Macintosh during any school breaks while her father William Styles was out of the country. This document was also signed by Valerie but in the name of William Styles.

Lisa Meakins studied the documents carefully and then placed them inside a file marked ‘Valerie Swindon’ which appeared to contain all of the other paperwork provided to the school.

The Deputy Headmistress’s face clouded over, her smile and pleasant countenance vanished.

“I’ll be candid with you Miss Swindon. I don’t like girls joining mid-term and I don’t like them being given preference because their daddy has money. This school has a long and distinguished history of only taking the ladies from the best families,” once again her mouth turned down.

Valerie was about to respond when Lisa continued.

“Keep your head down. Study hard and obey the rules and we’ll get on fine,” the Deputy Headmistress’s smile returned.

There was a soft knock at the door.

“Come,” Miss Meakins commanded.

Valerie turned her head and was surprised to see Emily Milford enter the study.

“Valerie Swindon meet Emily Milford; she will be your chaperone, your mentor, and your companion until you are settled in,” Lisa announced.

“She is one of my most trusted students and you would do well to take her advice in all matters,” the Deputy Headmistress cautioned.

Emily smiled at Valerie. An honest, open, friendly smile.

Oh course Valerie knew that Emily attended the school; meeting Emily had given her the idea to hide out here in the first place. But she had not expected to be so close to her so soon. Valerie was quietly confident that Emily would not realise that underneath the lipstick, powder, classic bob hairstyle and school uniform was her brother’s best friend William Styles. But confidence was not certainty.

Valerie and Emily climbed the stairs to the top floor.

“Having to climb these stairs every day is a pain in the arse, but at least on the fourth floor we have single dorms,” Emily smiled.

“Oh and by the way, never use terms like ‘pain in the arse’ when there is faculty around. One would say ‘it is tedious’,” she touched Valerie lightly on the arm and giggled.

It was the same laugh that had enchanted William when he first met Emily when he stayed with her brother Stephen, at the Milford family estate in the Cotswolds.

The two girls approached an open door.

“This is your dorm 4F, I’m across the corridor in 4B,” Emily smiled.

As the girls entered Valerie's dorm they surprised Harry Cartwright who, having delivered Valerie’s suitcases, was rummaging through one of them. He held a pair of Valerie’s satin panties to his face while he rubbed at his crotch.

“Hey you dirty old pervert. Fuck off or I’ll tell Miss Meakins and have you sacked!” Emily screeched.

Harry Cartwright grinned at the girls showing blackened teeth. He rubbed the stolen knickers on his tented crotch and then to Valerie's amazement, shoved them in his pocket.

He approached Emily and glared at her.

“You won’t tell Miss Vinegar Tits fuck all. You keep your secrets and I’ll keep mine,” he brushed past the two girls sniggering to himself.

“What the fuck?” Valerie was flabbergasted.

“You’ve probably worked out already that this place is a dump and is going downhill. There simply isn’t enough money to maintain the place properly or hire enough staff. The tutors are all good at their jobs but they’re underpaid and the support staff have suffered huge cuts,” Emily began.

“Harry Cartwright does the jobs of three men but he doesn’t complain. He doesn’t complain because he has a thriving business selling us girls contraband.”

“He sells us ciggies, booze, a little grass now and then, dirty magazines for those who like them, johnnies and contraceptive pills too; almost anything you want, Harry can get.”

“The only problem is he is a dirty old pervert. Don’t leave any underwear or valuables out while he’s around and keep your door locked. Try not to be alone with him if you can help it.”

“He serves a useful purpose but the cost is that we can’t tell on him; so he takes liberties. I guess it’s what they call in the Western movies a Mexican standoff,” Emily explained.

“Don’t worry. Things aren’t that bad here. It’s still a really good school as far as the tuition is concerned and still well respected, and most of the girls are really nice. We’re a bit sort of Saint Trinian’s if you know what I mean.”

Valerie burst out laughing and Emily laughed along with her.

“I was saying the same thing to a friend of mine. The uniform is very Saint Trinian’s, and now I find out the school is very similar,” Valerie chuckled.

“Yeah, the uniform is very archaic but you get to like it. Wearing stockings instead of tights can be a pain in the arse though,” Emily agreed.

“Oh I don’t know. I kind of like wearing stockings,” Valerie grinned.

Emily reached out and touched Valerie's arm in that way she had.

“I think we are going to get along just fine. There’s something about you; you’re…quirky…I think is the word. And I love your voice, smoky and seductive,” Emily blushed.

“Oops I might have gone too far,” she reddened.

Valerie took Emily’s hands in hers and smiled.

“No; I think you’re right, I think we are going to get along swimmingly,” Valerie said.

“Ok, so this is your dorm. Not too bad but not sure they’re worth the three hundred quid a year extra we pay for them; but we have privacy at least. Some of the girls are four to a room,” Emily explained.

“You can put up posters and decorate it pretty much any way you want, just keep it clean. Like I said, I recommend you lock your room whenever you are not in it,” she handed Valerie a clunky looking antique key.

“We are lucky. The bathroom and toilet are right next door to our rooms so we don’t have far to walk on chilly mornings. Bad news is when it’s quiet you can hear the girls piddling and farting through the walls. Good news is there are no adjoining dorms so you won’t have to put up with the noise of their records or radios; the walls are thin,” she smiled.

They went next door and checked out the bathroom which had two stalls with full-length wooden doors and old cisterns mounted above the loos with pull-chains to flush them and two baths in two bathrooms that had recently installed shower heads above them. There was a row of four sinks with mirrors above them. The place seemed pretty clean.

“I recommend you wear a bathrobe at all times when you are not actually in one of the bathrooms. That old perve Harry Cartwright has a habit of needing to empty the bins or clean the place when it’s occupied, even though he knows he should keep out when the girls are using it,” Emily warned.

“Look that’s about it for now. Lock your door and we will go down to the dining hall. It’s morning tea time and you can meet the other girls,” Emily said.

And so Valerie spent her first day in the Finishing School meeting the girls, getting to know the unwritten rules that cliquey girls have, finding her way around, and attending her first classes.

After a week Valerie was settled into the routine at the school. She had her syllabus worked out and had been assigned a House. There were some compulsory subjects and some electives. Valerie was happy that she had chosen subjects that interested her; they weren’t necessarily preparing her for her future because she already had an idea where that lay.

Being a savant of all things economic and commercial, a vague business plan was starting to form.

As well as lessons, there was also compulsory physical education or PE, and also an hour a day ‘school improvement and beautification projects’ which really just equated to using the girls to help with maintenance. The girls were told that it was ‘character building’.

Some of the ‘school improvement’ tasks involved washing dishes in the scullery, cleaning common areas, cleaning the teachers studies and common rooms, minor furniture repairs, and light gardening.

Two events occurred during school improvement periods that affected both Valerie and Emily.

The first was when Emily Milford was tasked to clean up Dean Jenkins study. She found that he had left the file marked ‘Valerie Swindon’ out on his desk. Emily couldn’t help herself but open the file and read the contents having closed the door and locked it. She was shocked and confused by the file’s contents.

The second event was when Valerie was detailed off to help with the gardening during her period of school improvement. She went searching for Harry Cartwright in order to find out what tasks she would be required to undertake.

She saw movement in the glass greenhouse and naturally assumed that it was Harry. And it was. But as Valerie made her way down the narrow aisle between the potting table in the centre of the greenhouse and the juvenile plantings against the glass wall she saw that Harry was not alone.

Alice Corinda, a pretty plump girl with mousy hair who was noted for being not very intelligent was sitting on the potting table, her feet swinging about six inches above the ground. Her legs were open and she was holding up her skirt while Harry Cartwright stood between her legs with his trousers down, masturbating.

He looked over his shoulder as he heard Valerie approaching and rather than stop what he was doing he grinned and continued to stroke his cock. Valerie stood there stunned. Harry ejaculated over Alice’s thighs and crotch, his semen splattering on her legs, her stocking-tops, and the front of the non-regulation red nylon see-through panties she was wearing.

“Oh yes; there’s a good girl,” he groaned and then deliberately looked at Valerie.

“Oh yes, very nice Mister Cartwright. Do I get that packet of fags and bottle of gin now?” Alice beamed.

Valerie shook her head, disgusted that Harry would take advantage of a simpleton like Alice Corinda, but not at all surprised. She spun on her heels and began to walk away.

“It won’t be long gillie,” he cackled in that awful phlegmatic voice of his.

“You gillies is all the same. You all turn your nose up at me until you want something,” he called after her.

Both of those two events had follow-on effects.

Emily had made it a habit coming over to Valerie’s room after dinner and spending time with her. They would smoke Benson and Hedges cigarettes, blowing the smoke out of the window, and drinking gin and tonics from the contraband Emily had purchased from Harry.

One evening they lay side by side on Valerie’s bed staring up at the ceiling and chatting, feeling buzzed from the G & T. The door was locked to keep out unwanted visitors and to give them time to hide their transgressions should the duty teacher pay a visit. The room was dark; lit by the feeble glow of a single lamp with a red translucent scarf draped over it.

“How much do you reckon that perv Harry makes selling us bootlegged goodies?” Valerie asked.

“I don’t know but it’s got to be a lot. There are sixty of us enrolled and most of the girls buy stuff from him,” Emily rolled over and looked at Valerie inquisitively.

“What are you staring at?” Valerie asked.

“Nothing. So why do you ask about Harry?”

“I caught him wanking over Alice Corinda’s knickers and stockings in the greenhouse,” Valerie turned her head and blew smoke at the window.

“Some of the girls don’t have a lot of money and also Alice is soft in the head. They say that she would show you her knickers for bite of your toffee apple way back in junior school,” Emily giggled.

“But seriously some of the girls pay him with…well…you know,” she blushed.

“You know what?” Valerie teased.

“They ahem. They ahem…let him touch them. Or they touch him. I heard that one of the girls used her mouth on him once to pay off a large debt,” Emily flushed with embarrassment.

“But no one fucks him?” Valerie quipped.

“Eew! Don’t be disgusting! Most of the girls here are virgins and none of them would let him do that!” she was quite miffed.

“I was only teasing. I wouldn’t let that dirty old perv within three feet of me,” Valerie snorted.

There was an uncomfortable silence while they both just smoked and sipped their drinks.

Eventually Valerie rolled over to face Emily.

“Are you a virgin?” Valerie asked.

“Oh my! I never expected that question,” Emily’s cheeks coloured.

She reached over Valerie to pour them both another gin. They were both aware of how close and intimate their bodies were. Valerie could feel Emily’s budding breasts pressing into her and they could smell each other’s scent. Emily’s thigh rested against Valerie’s.

“I’ll tell you my secret if you tell me yours,” Emily sighed, looking deep into Valerie’s eyes.

Valerie’s lips were a scintilla away from Emily’s.

“You first,” Valerie whispered.

“Three years ago when I was fifteen. He didn’t know what he was doing and neither did I. It wasn’t good. Then later when I was sixteen one of my Uncles took a shine to me. I knew it was incest but he sure knew what he was doing. He taught me a lot and he bought me presents to I would keep it secret. A couple of other boys since but only when I wanted to,” she smiled a little guiltily down at Valerie.

“There was this boy used to come and visit my brother. I really, really, liked him, even though he was a bit effeminate and we were more like friends than anything else. I wanted him to shag me but I think he was gay. I think he might even have tried on my knickers while I was out.”

Valerie blushed scarlet and searched Emily’s eyes for any hint of knowledge as to her true identity but Emily’s eyes remained bright and wide.

“He had piercing green eyes just like yours,” Emily softly pressed her lips against Valerie's.

“Do you want to know my secret?” Valerie sighed.

“I think I already do. I wasn’t sure until tonight; I couldn’t believe it when I read your file. But your reaction to my story betrayed you,” Emily’s lips were still so close to Valerie’s that she could taste her breath.

“And?” Valerie searched Emily’s eyes.

“And?” Emily lowered her lips to Valerie's and kissed her.

“Oh my god so soft,” she sighed and kissed her again.

This time the kiss became hungry. Their lips mashed together smearing their lipstick. Valerie rolled over so that Emily was underneath her. They kissed again and Emily gasped with pleasure. Valerie slowly unbuttoned Emily’s blouse while Emily ran her fingers through Valerie's hair.

Valerie found Emily’s budding breasts cupped inside her lace brassiere. She teased Emily’s nipples through the fabric and Emily’s tongue slid into Valerie’s mouth, encouraging her to continue. Valerie freed Emily’s little titties from the cups of her bra and lowered her lips to gently bite and suckle her nipples.

Emily gasped and writhed on the bed under Valerie. She held Valerie's head to her breast and encouraged her to suckle her breasts. Valerie complied with Emily’s wishes and allowed one of her hands to snake down Emily’s body and under her skirt. She ran her fingernails across the pale sensitive skin above Emily’s stockings and caressed her thighs. Valerie’s fingers rustled on the sheer nylon of Emily’s stockings.

“Oh my!” Emily gasped.

Valerie returned her face to Emily’s and continued to kiss her. Valerie's fingers slid across the front panel of Emily’s panties and she felt the warmth of her sex through the sheer nylon knickers. Emily reciprocated and was confused at first; all she found was a smooth mound but then she realised the obvious.

“Can I?” Emily looked into Valerie’s face with wanton lust.

Valerie nodded.

Emily’s fingers slid inside Valerie’s knickers and found the surgical tape and tore it free. Valerie’s hard cock sprang forth into Emily’s fingers.

“Oh my, oh my!” Emily registered her surprise.

Valerie sild her hand inside Emily’s panties and found her mound wet. Her pubic hair was soaked and the musky scent of her sex permeated the room. Valerie used the pad of her finger to stimulate Emily’s clitoris. Emily pushed Valerie’s finger away.

“No! I’m nearly there and I want you in me when I come,” she gasped.

“Put me in you. I want so much to be in you,” Valerie pressed her lips to Emily’s and slid her tongue into her mouth.

Emily freed Valerie’s cock from the gusset of her panties and eased aside her own knicker crotch and guided Valerie’s erect penis between the folds of her labia.

Valerie rose to her knees and Emily raised her legs and crossed her ankles behind Valerie’s waist. Their stockings rustled and sent shivers of delight through them as Valerie impaled Emily on her hard throbbing phallus, driving her shaft deep inside Emily.

Emily rubbed her legs against Valerie, encouraging her.

“Fuck me! Fuck me please!” she moaned.

Valerie complied and fucked Emily with long, slow, deep strokes. Emily’s vagina was tight but moist and Valerie pressed her pubis into the folds of Emily’s vulva, stimulating her clitoris.

“Oh god I’m coming!” Emily drummed her heels and pulled Valerie close to her.

Emily shook and shuddered and screamed as her orgasm erupted from deep inside her. Valerie thrust in as deep as she could and ground her groin against her lover and secreted her seed deep inside Emily.

They clung to each other rutting and thrusting and moaning and groaning until they were spent. They slowly came down from their climaxes and Valerie lay between Emily’s legs, her semi-erect penis still inside, kissing her tenderly while Emily smiled up at Valerie and kissed her in return.

“So…do you wanna know my real secret?” Valerie needled her lover.

“Oh you!” Emily spanked Valerie on the buttocks.

Valerie made to climb off Emily but Emily wouldn’t let her.

“Don’t! I want you in me,” Emily pouted.

“Happy to oblige,” Valerie kissed Emily affectionately on the nose.

“Who else knows?” Emily looked up questioningly.

“Only one other person,” Valerie smiled down at Emily.

“And?” Emily’s eyes searched Valerie’s.

“And it’s a long story and I’m getting hard again,” Valerie grinned.

“Well first things first then,” Emily giggled and began to lift and grind her pubis against Valerie as she felt her harden inside her.

Two of the girls walking past Valerie’s room heard Emily scream with lust and they giggled. Lesbian relationships were a common occurrence at the school amongst those who boarded.

The other follow on effect happened the next day.

Valerie was once again assigned to gardening duties. This time thankfully she didn’t have to work close to Harry Cartwright. Harry gave her a barrow and a rake and had her raking leaves off the lawns and take them into the woods to dump them.

The day was cool and after about half an hour Valerie desperately needed to pee. She had just dumped a barrowful of leaves in the woods and she wasn’t sure if she could make it back to her dorm before she peed herself. The grass was long with the odd stinging nettle here and there; she had already laddered a stocking. She squatted down and the cold wet grass tickled her thighs.

“Fuck this!” she looked around and saw no one.

She stood up and reached into her knickers and tore off her gaff; she freed her cock from her knickers, lifted her skirt, and leaned against the tree and pissed. It felt so good!

“Oh gillie! Oh my god gillie! Oh my god gillie you goin’ to get it now!” Harry Cartwright had been secretly watching her and he was amazed and delighted with what he saw.

It took him seconds to sprint from where he hiding to get in behind Valerie.

He pushed her hard against the tree.

“Well now gillie. That ain’t right gillie! You ain't a real gillie at all are you? But you’re pretty and your arse is soft,” Harry had knocked the breath out of Valerie and he was pawing at her buttocks through her knickers.

“Oh yeah, your arse is real soft. But if I tell those snooty cunts who run this joint about you…well gillie you is just plain out fucked!” his rancid breath accosted her nose as he reached around and squeezed her limp penis.

“Or you can just be plain fucked!” he let go of Valerie’s penis and used his weight to hold her against the tree while he freed his erect penis from his trousers.

“Now hold still gillie and this won’t take long,” he spat on his grizzled phallus.

It was long, thick and gnarled and when he pushed it into Valerie she screamed.

“That’s it gillie. You let it out!” Harry pushed himself all the way inside Valerie’s anus and rutted.

Valerie was determined not to show any further sign of discomfort or pain. She grunted as he thrust in and out of her tight anus, his spit providing barely any lubrication. Mercifully he came quickly and his semen provided sorely needed lubrication as he finished fucking her.

“Oh I like this gillie. I like this a lot. Harry don’t care that you got a willy so long as you got those nice soft cheeks and that tight arse.”

“We gonna be doing this a lot.”

He thrust deeply into her one last time and then pulled his cock out of her anus and wiped it on the back of her knickers.

“I’ll keep these as a souvenir too!” he grunted and pulled down her panties and made her step out of them.

“I’ll see you real soon gillie,” he wiped the knickers across his face and stuffed them in his pocket.

He walked away laughing.

Valerie stayed leaning against the tree until she gained her composure. She refused to cry even though she felt humiliated. She straightened her stockings and smoothed her skirt and pushed the wheelbarrow back to the toolshed. The walk was agony at first but the pain began to subside.

She was able to sneak into her dorm without too much bother. She stripped off her clothes and wrapped herself in her woolly bathrobe and made her way to the bathroom where she used the toilet to push out as much of Harry as she could and then she took a shower.

After the shower she went back to her dorm and came back with her cigarettes and a glass full of gin. She poured herself a bath and lay in it.

She soaked in the bubbles and plotted her revenge, drinking gin and chain smoking. She slowly began to smile.

To be continued.

Finishing School For Young Ladies Ch5

Author: 

  • M. Gorman
  • Michele Nylons

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • EXPLICIT CONTENT

Publication: 

  • Serial Chapter

Genre: 

  • Transitioning

Character Age: 

  • Teenage or High School

TG Themes: 

  • Disguises / On the Run / In Hiding
  • Fresh Start
  • School or College Life

TG Elements: 

  • Bad Girls / Promiscuity
  • Fancy Dress / Prom / Evening Gown
  • Girls' School / School Girl
  • Prostitution

Permission: 

  • Posted by author(s)
Schoolgirl.jpg

Finishing School For Young Ladies

By

Michele Nylons

Chapter Five – Revenge Is Mine

The following weekend was Easter and the school was closing for the four day holiday. On the Wednesday night Emily and Valerie slept together in Valerie's room. Emily locked her door and put a do not disturb sign on the doorknob and padded across to Valerie’s room and locked the door behind her.

The girls slept in satin knickers and bras, stockings, suspenders and satin full-slips to enhance the pleasure of their lovemaking. That is to say they didn’t really sleep much at all and both were sore the next morning.

“Are you sure you won’t come with me to the Cotswolds? I’ll just introduce you as my new friend,” Emily nuzzled Valerie’s neck and toyed with her semi-erect penis.

“I’m sorry honey but it would be just too weird meeting your family like this, especially Stephen,” Valerie replied, lazily stroking Emily’s labia through her silky knickers.

“Yeah…and it would be funny if Stephen tried to shag you,” Emily giggled and squeezed Valerie's cock.

“Yeah…well that would be something…fucking a sister and a brother,” Valerie teased.

“But seriously, I have something I have to take care of over Easter,” Valerie said.

“Well seriously…I have something you have to take care of right now,” Emily pressed her lips to Valerie’s.

Valerie was fully tumescent and Emily slid under her, wrapping her silken-hosed legs around Valerie’s. They both loved the feel of their stockings rubbing together as they fucked. She guided Valerie's cock to her entrance and Valerie slipped inside her buttery cunt for what had to be at least fifth time that night; dawn was breaking outside.

They were in no rush and Valerie took her time sliding her hard cock in and out of Emily as Emily clung to her and gyrated beneath her to increase their pleasure. Their orgasms came slowly but when they came, they came together, the intensity magnified because they had teased it out for so long.

Valerie quickened the tempo and Emily bucked to meet her thrusts.

“Oh yeah fuck me! Fuck me darling! Fuck me lover!” she moaned, biting Valerie’s lip hard enough to draw blood.

Emily was an energetic and vocal lover and it excited Valerie when she expressed her passion like that.

Valerie took Emily’s buttocks in her hands and squeezed them as she drove her cock in and out of her slick cunt. Emily ground her cunt against Valerie so that her clitoris was fully stimulated. They orgasmed together as they usually did; Valerie driving herself deep into Emily’s vagina and ejaculating and Emily writhing underneath her, ripples of pleasure ringing out from her clitoris and along her vagina.

Seeing the two of them dressed for morning assembly in their school uniforms and toppers you would never have guessed that they were both wanton sluts.

Deputy Headmistress Lisa Meakins wished them all a happy Easter and told them to come back safe for the next term and harped on about being virtuous and that chastity was to be treasured and could only be given away once. The young ladies were hardly listening; they couldn’t wait to get away for the small holiday.

Sally Macintosh was waiting for Valerie, leaning against a taxi out front of the school. She greeted Valerie with a chaste kiss on the cheek; a pretence for the crowd of students, faculty, and parents.

As soon as the taxi was out of sight of the school Sally fell on Valerie and the two gorgeous creatures ravaged each other in the back seat of the taxi.

“I’ve paid him double to keep his eyes on the road and to take the long way home,” Sally grinned as she slipped her tongue into Valerie’s mouth.

Valerie had anticipated they would make love as soon as they got home and was prepared. She straddled Sally and freed Sally’s hard cock from her knickers, pulled her own panties aside and lowered herself on Sally’s erection.

“Mmm, I’ve missed that,” Valerie looked down at Sally’s pretty face and slowly raised herself up and down.

“Mmm, me too,” Sally gripped Valerie’s hips and guided her, thrusting up to meet her lover.

“I told you I was going to enjoy fucking you in that uniform,” Sally smirked.

“Stop talking about it and just do it then darling,” Valerie teased her and picked up the tempo.

It didn’t take Sally long. Although Sally had sex constantly working as a prostitute, this was different and she was at maximum arousal being with her lover whom she hadn’t seen for nearly two months.

Sally pulled Valerie down into her lap and thrust upwards with all her might and Valerie felt Sally ejaculate against her prostate. Valerie came in her knickers without even touching herself she was so excited to be with her lover. Because of the constant lovemaking with Emily the night before, her emission was diminished but the sensation was no less intense.

They kissed and canoodled and Valerie remained straddling Sally on the back seat until the cabbie cleared his throat.

“Ahem…ladies. I’ll have you home in two minutes unless you want me to go around a few more blocks,” he grinned into the rear view mirror.

“No we have a nice big bed waiting,” Sally smiled at him.

“Half yer luck,” the cabbie laughed.

They just made it to the bed for round two and this time Sally wanted Valerie to fuck her. It took some effort; Valerie’s cock was red raw from fucking Emily non-stop the night before but it actually served her purpose because it took her ages to come. Sally got the long hard fucking she wanted, although the feeble dribble that came from Valerie when she orgasmed was testimony to a cock that was overused.

Sally made coffee and bought it back to bed and they snuggled and nuzzled and chatted. They both had some catching up to do.

Valerie decided to tell Sally everything that had happened at the Chelmsford Finishing School for Young Ladies and she did. Sally was obviously jealous of Emily but Valerie appeased her.

“Hey! I love making love to Emily…but I love only you,” Valerie said, kissing Sally’s cheeks, then her eyelids and finally her mouth.

“Really?” Sally looked lovingly into Valerie’s eyes.

“Yes Sally. I love you,” Valerie smiled back.

“What about the age difference, and the fact that I’m a prossie, and also…” Valerie shut Sally up with a passionate kiss that led to more lovemaking.

This time Valerie made the coffee and bought it back to the bed.

“And what about you my sweet? How have things been here?” Valerie enquired.

“Oh wonderful. I can’t thank you enough for this flat. Now that I have this gaff I take on only the punters I want to, and I can do it safely there in the workroom,” Sally nodded with her chin to the third bedroom across the hall.

“No more up against the wall or on my knees in a dark alley hoping the Old Bill doesn’t come along, or short time in a sleazy hotel being ripped off by the clerk or the punter.”

“And I have a better class of clientele who pay more. I only see those who I want to see, but I have a string of regular punters who recommend me to other punters so I’m making a shitload more money. Look!” Sally scrambled around in the drawer and withdrew a bankbook.

It was an account that Valerie had set up in Sally’s name.

“Jeez it’s a wonder you’ve still got an arse! All that money! You must be fucking like a rabbit!” Valerie teased.

They rolled around in the bed some more but neither had the energy for a fucking.

“Alright there is something that I didn’t tell you about and it’s nasty. I’ll get us a drink for this one,” Valerie padded into the lounge to the little bar in her stocking feet.

She bought a bottle of scotch into the bedroom and generously filled two tumblers and lit them both cigarettes.

“So there’s this creepy perv Harry Cartwright who sells contraband to the girls…” Valerie told Sally the whole story.

When it got to the part about Harry forcing himself on Valerie in the woods, Sally burst into tears and clung to Valerie, who consoled her.

“Hey honey; nothing worse than what some of the punters have done to you,” Valerie said resignedly.

“But anyway it’s got me thinking. What if we replaced Harry Cartwright?” Valerie smirked and sipped her scotch.

“What do you mean?” Sally was puzzled.

“Do you know someone who we could trust to sell contraband to the girls at the school? Someone we can trust implicitly? Someone who will treat the girls fair and make sure we get our cut? Someone who won’t try to get into the girl’s knickers?” Valerie asked.

“You’ve been working in Soho for what? Fifteen years now? Do you know someone like that?”

Sally stared at the ceiling concentrating and Valerie knew better than to interrupt her. She slid a lighted cigarette between Sally’s lips but left her alone to think.

Eventually a grin spread across Sally’s lips and she rolled over and found her scotch and took a deep draught.

“Pass me over me little black book,” Sally pointed to her appointment book on the bedside table.

“‘Pass over ‘my’ little black book’, if you please,” Valerie jokingly scolded her.

“Don’t go all Eliza Doolittle on me now,” Sally quipped and thumbed through her little black book which contained the names of her punters and contacts.

“Yes! Here he is. A real Julius Caesar this bloke is,” Sally finished her scotch and held out the glass for Valerie to refill it.

Valerie looked at Sally nonplussed.

“Julius Caesar…Geezer… you cloth-eared bint,” Sally teased Valerie.

“Hey! I might be a master criminal but I’m not street savvy like you, love of my life,” Valerie snuggled up to Sally who smiled back at her lover and kissed her.

“Right! Pass me the dog and bone and I’ll ring this geezer and we can meet him down the rub-a-dub-dub,” Sally mimicked a Cockney accent.

“You keep talking like that I’ll throw you down the apples and pears,” Valerie smacked Sally on her shapely pantied arse and dumped the phone on the bed.

“I’m going to have a shower and get changed while you call up your geezer,” Valerie wriggled her bum and strode off to the bathroom.

It was still cold and Valerie and Sally wore pantsuits and London Fog raincoats down to the Pig and Whistle pub to meet Billy ‘The Bottle’ Butler.

Sally and Valerie sat in a booth waiting for Billy and Sally went on to explain a bit more about him.

“Billy used to be a ‘Face’. That is he was a hard man, high up the organised crime ladder but too many of his mates got nicked so he’s semi-retired. They call him ‘The Bottle’ because he isn’t scared of anyone.”

“Now he’s a small time fence and moocher. He shifts bootleg gear around, turning a small profit, but I know he’s had enough of that even, because of the risk of getting nicked. He’s done a couple of stretches and he doesn’t want to do any more time inside. This would be the perfect job for him,” Sally explained.

Billy ‘The Bottle’ Butler was a handsome fifty-something man who carried a small pot belly on a muscled physique. His slick black hair was combed back and he wore a tracksuit and trainers; preferred wardrobe of the East Enders.

He was surprisingly well spoken, polite, and a real gentleman. He bought them all drinks and then they got down to business.

“So here’s the deal. You take the job as the groundkeeper, gardener, porter and handyman at the Chelmsford Finishing School for Young Ladies,” Valerie began.

Billy’s mouth turned down in a moue.

“Wait for it. Here’s the sweetener. There are sixty young ladies there and most of them live in. They have a penchant for cigarettes, booze, soft drugs, contraceptives, magazines, makeup, chocolates and all sorts of contraband that is off limits to them. I’m sure you can find more items the girls might like to purchase; so long as there are no hard drugs it’s up to you,” Valerie went on.

“The work isn’t hard, and to anyone looking, it seems legit. You even get a little cottage to live in, in the woods at the back of the school.”

“What’s the catch?” Billy looked sceptical.

“Like I said. No hard drugs or anything that will hurt the girls; you sell anything else you like. We take a third of your profit and you keep the rest,” Valerie smiled.

“Sounds too good to be true,” Billy sipped his pint but he was interested.

“Why isn’t some other geezer already at it?” he looked questioningly at the two women.

“Well that’s the catch. There is someone already at it. But don’t worry I’m going to get the dirty old perv who is currently in the job sacked or at least suspended. You have to make sure he never comes back,” Valerie explained.

Billy grinned.

“For a young brass you’re a ballsy cunt.” He took another sip of his Bitter.

“Oh I’m not a brass. I’m a student,” Valerie smiled at him.

“Well I’ll be fucked!” Billy grunted.

“That’s the only other catch. No fiddling with the girls,” Valerie looked at him deadly serious.

“So I take it the incumbent is kiddie fiddling the girls then?” Billy’s face clouded over.

Valerie just nodded.

“You’ll have no problems with me that way. I bat for the other team love,” Billy grinned.

The kafuffle began in the gardener’s shed where Deputy Headmistress Lisa Meakins had found a box of semen stained knickers and stockings. It continued on into the gardener’s cottage where a perfunctory search revealed a stack of magazines with young girls posing provocatively in school uniforms and more stolen lingerie, some of which had obviously been masturbated in or on.

But the most condemning evidence was a bundle of Polaroid photos of Harry Cartwright wanking himself over Alice Corinda’s plump, stocking clad thighs. The final picture, a shocking depiction of his ejaculate dripping on her stockings and knickers while Alice fondled his balls.

Harry Cartwright was summarily sacked despite his claims of innocence and of being set up.

Valerie and Emily had easily cajoled Alice Corinda to offer her services to Harry Cartwright. Emily had promised Alice that she would access the school’s files and up her grades and pay for anything she wanted in the way of contraband for three months. Valerie had simply given her twenty quid.

Harry was too much of a pervert to say no when Alice offered him the use of her body for a packet of Woodbines.

Emily had taken the Polaroid pictures through the rather suspiciously recently cleaned window of the gardener’s shed with the new Land camera she had received for her last birthday. She was worried that Harry would hear the camera’s mechanism winding as it spat out the pictures but Harry was concentrating so hard on Alice Corinda’s black stockings and pink nylon panties and the bounties they encased that he never heard a thing.

Valerie and Emily already knew about Harry’s stash of ‘wank fodder’ knickers and stockings, they simply added the magazines and the photos to the stash in his cottage and got Alice to make the complaint.

As expected; Harry Cartwright took his severance pay down the pub that night and got rolling drunk and complained to anyone who would listen that he had been set up and wrongfully sacked. No one thought for a minute that Harry wasn’t fiddling the girls at the Finishing School, they all suspected that he was a noncer.

When he started on about some transvestite schoolgirl being behind it all, the publican cut off his beer and kicked him out telling him that next thing it would be down to aliens from flying saucers.

Harry stopped for a piss in the dark alley behind the pub and he didn’t see Billy ‘The Bottle’ until it was too late.

He woke up three days later in hospital and was told he would be in a full body cast for three months. Harry knew better than to talk to the Old Bill and as soon as he was released from hospital he moved north to Newcastle where his brother could look after him.

Billy ‘The Bottle’ Butler got the job as the new gardener, handyman, come porter at the Finishing School by turning up as soon as the position was advertised. He wore brand new dungarees, was showered and shaved and spoke politely but confidently to Lisa Meakins and Dean Jenkins who were panelling the job. He came with excellent references; and when he offered to take the job for half of what they had been paying Harry, the job was his.

Things were going swimmingly for Valerie now. She had Emily as her lover while she was at school and Sally during the holidays.

She was also making plenty of money which was her favourite pastime besides fucking Sally and Emily. Billy was turning over nearly two hundred quid a week to Valerie as her cut from illicit sales to the girls at the school and Sally was making around one hundred pounds a day as a prostitute. Valerie figured she and Sally were making around thirty thousand pounds and change a year.

They were on easy street with the money Valerie had hidden away in Grand Cayman and the ready funds available at her Commercial Bank.

But then a surprising new enterprise offered itself as a possibility.

Valerie had been living at the Chelmsford Finishing School for Young Women for just under a year when flyers started to appear advertising the Harvest Festival dance.

“So what is the Harvest Festival dance?” Valerie asked Emily.

“Oh it’s an annual dance we hold with the girls from here and the boys from the Bridge Street Academy. The tradition goes back to when the schools were first built or something. I do know that over the years quite a few Chelmsford ladies have married Bridge Street men,” Emily explained.

“It’s a chance for the girls to dress up and for the boys to try and get a little slap and tickle is what it really is. Even the teachers get pissed because alcohol is allowed in ahem… moderation; if you know what I mean,” Emily tapped the side of her nose.

Valerie wore a red satin floor-length ball gown, split down one side to the top of her thigh, and red velvet highheels. Her makeup was heavy but perfect; after all it would be an outside cotillion in the evening. She accessorised with silver drop earrings, silver necklace, a diamond bracelet with matching diamond ring on one finger and a red clutch with silver clasp.

Her lingerie consisted of red satin full-cut knickers so as not to show any panty-line, matching padded bra and flesh-toned holdup stockings. She didn’t want a suspender belt to spoil the lines of her dress but she didn’t want to wear tights.

Emily was dressed similarly only in sky blue.

A marquee tent had been set up on the lawns and a big band played dance music. Bowls of punch, already spiked by the attendees, nibbles and napkins were laid out on long benches and the students and staff were enjoying themselves.

Valerie was pleased that dancing was a compulsory subject at the school. She had been a half-decent dancer as William, but learning the steps backwards and carrying them out in highheels was an artform in its own right.

She found herself in the arms of a handsome young man from the Bridge Street Academy and he was obviously taken with her. He’d followed her around most of the evening like a lost puppy in hopes of getting a dance.

This was new territory for Valerie. She’d had sex with a woman and another transvestite since she had transitioned; but this was the first time she had been close and intimate with a man.

And she liked it.

She was flattered by the attention and adoration the dark haired, hard bodied, good looking, young man showered on her. He beamed at her and held her tight against his black tuxedo-clad body. He breathed her perfume and she his aftershave.

The band played a slow number and she rested her head on his shoulder and he drew her tighter. She could feel the bulge in his trousers through her dress and his hot breath on her neck.

“You’re beautiful. The most stunning woman here,” he whispered.

“Hardly,” she replied.

“I’m pretty fucking hot but I’m not sure I’m not the most stunning,” Valerie teased him.

“Modest too,” he jested back.

“You’d give anything to kiss me though wouldn’t you,” she raised her head and smiled cheekily at him.

“Anything,” he grinned.

“Then find me a decent drink and join me in the rose garden for a cigarette. If you’re lucky I might even do something about this for you,” Valerie reached between their bodies and squeezed his erection.

The lad blushed and gasped and Valerie giggled.

“See you soon,” she pushed him away gently and walked away and out of the tent.

The young man watched her, his eyes drawn to her firm buttocks and the long legs sheathed in sheer nylons as her dress opened and closed as she strode away.

Valerie walked over to the rose garden where it was dark. The rest of the lawns and gardens were lit by fairy lights and torches.

She found what she was looking for; a small folly in the centre of the rose garden that was virtually hidden from view. She opened her purse and took out her cigarettes and lighter and placed them on the handrail. She thought it was funny that ladies old enough to drink were not allowed to smoke in public at the school.

Valerie also found the other things she was looking for. One was a small tube of Vaseline and the other was a nailfile.

She looked around and saw that there was no one around and she crouched down and dropped her knickers to her knees. She took the nailfile and made a small hole in the back of her knickers next to the cotton crotch. She lubricated her sphincter with Vaseline and pulled up her knickers.

She had fully intended to lose her virginity to a man tonight and now she was ready.

She lit her cigarette and it acted like a beacon for the handsome randy young man who was searching for her in the rose garden. He found her in the folly and drew her into his arms and kissed her passionately. Valerie responded by slipping her tongue into his mouth which surprised the youth.

“You Chelmsford girls are quite forward,” he grinned, holding her tight.

“Well I don’t know about the others, but I am,” Valerie grinned.

“Now is that a flask in your pocket or are you just pleased to see me.”

“Well both actually,” the boy smiled and produced a hipflask.

“I’m Troy Bingham by the way,” he smiled.

“I’m thirsty,” Valerie teased him and snatched the hipflask.

She tilted her head back, upended the flask and swallowed the liquor which had a nice bite. She slammed the flask down on the rail, dropped her cigarette, and pulled Troy to her.

“That was nice now come get your reward,” she kissed him and pressed her body against his.

He responded by putting his arms around her and returning her kisses. His erection was back to full tumescence.

Valerie broke the kiss and looked at his eyes in the dark. He had her pressed against the railing of the wooden folly.

“I’m going to tell you something now so you won’t be disappointed. I’m going to pleasure you and you will enjoy it; but you are not going to put your cock in my vagina,” Valerie whispered.

“Like most girls here I’m saving my virginity for my wedding night. You are not even going to get to touch my pussy. That’s for my husband on our wedding night. If you even try I will leave you here frustrated and unsatisfied and I’ll tell all the other girls that you are a cad ok? Promise?” Valerie looked at him intensely.

“Well yes I promise not to touch your vagina. You Chelmsford girls are very forward and forthright,” Troy looked a little worried.

“Oh don’t get too concerned. There is plenty we can do to pleasure each other without you touching my pussy,” Valerie grinned and smashed her lips against his.

She drove her tongue into his mouth and reached down and squeezed his cock through his trousers and Troy gasped. Valerie worked at his zip and freed Troy’s erection and began to stroke him. He gasped again and she smiled.

Troy squeezed Valerie’s buttocks as she slowly masturbated him; squeezing him tight then loosening her fingers, teasing him as he gasped and writhed with passion in her arms. She quite liked being in control.

She surprised Troy when she dropped to her knees and began to suck on his hard thick penis, working her tongue around the glans and her lips on his shaft. She sensed him starting to quiver and she stopped sucking him. She didn’t want him to come yet.

“Oh my god I’ve never had a girl do that to me,” he groaned.

Valerie decided to be kind and she swallowed his phallus again and sucked on the shaft as she used her tongue on the bulbous head. Troy held her face to his groin and shuddered with pleasure as he orgasmed.

Valerie’s mouth filled with semen which she greedily swallowed as she continued to suck on his cock draining it of every drop of come.

He remained erect, even after his climax, and Valerie was impressed. Troy pulled her to her feet and kissed her passionately, not concerned about the taste of his own semen on her breath. His hands slid inside her dress and he stroked her thighs, luxuriating in the feel of her diaphanous nylons. Valerie opened the split in her skirt so troy could rub his hard cock on her nylon-sheathed thighs.

She trapped his cock between her thighs and let him fuck her legs. She was so glad that she had gaffed carefully before the ball because she was fully erect but her cock was taped back between her legs. It was pleasurable and painful at the same time.

Troy’s cock slid up her thighs and began to rub on the front of her panties.

“Uh, uh! I told you, you can’t touch me there,” she chided him.

“God I’d give anything to fuck you,” Troy groaned.

Valerie smiled in the dark.

“Ok. You can do something. But if you tell anyone you’re dead to me understand?” Valerie hissed in his ear and bit his earlobe.

Troy nodded vigorously.

Valerie spun around in his arms and gripped the balustrade and pushed her buttocks into Troy’s groin. He took the hint and opened her dress so he could gaze on her magnificent knicker-clad bottom. Her satin encased globes glimmered in the dark.

“Oh! What’s this?” Troy found the little hole she had cut in her panties and pushed a finger in.

“You can put whatever fits in there; but nowhere else. My knickers are staying on to ensure that you don’t put that cock of yours anywhere it shouldn’t go,” Valerie wriggled her buttocks invitingly.

Troy pushed his finger further in the hole and found her puckered sphincter. He pushed his finger inside her bottom and Valerie moaned.

“Of fuck this is so hot I better get my cock in there before I come on your leg,” Troy gasped.

He positioned his cock at the hole in Valerie’s knickers and pushed it in. It just fit; the slinky satin clung to his shaft. His glans found Valerie’s sphincter well lubricated with the Vaseline. He grabbed her hips with the intention of entering her but before he could thrust forward, she impatiently pushed back.

Troy’s long thick cock slid inside Valerie’s anus filling her with his girth. Valerie was so aroused she ejaculated in her panties when his glans pressed on her prostate. Troy came almost immediately himself, he was so excited to be fucking a woman in the arse for the first time. Especially this gorgeous young lady.

Troy Pulled Valerie’s buttocks back against his groin and fucked her and emptied the last of his seed inside her and Valerie obligingly pushed back against him and wriggled her buttocks to encourage him.

Troy climaxed so hard that he oblivious that it wasn’t just his own semen soaking into Valerie’s panties; in fact most of the semen was hers.

When they had both finished coming it was time for practicalities.

“Ok when you pull out, do not get any of your stuff on my dress ok? Keep my dress pulled back away from my bum!” Valerie ordered.

Troy did as he was told and being a gentleman he padded his handkerchief and used it to wipe and dry Valerie’s bottom.

“I'm going to change my knickers now which is very unladylike and you are to turn your back and don’t look ok?” Valerie demanded again.

Troy did as he was told; turning his back to Valerie and lighting a cigarette while she rummaged in her purse and bought out a spare pair of knickers. She shimmied out of the cum-stained pair with the hole in them and slid on and smoothed out the fresh pair.

“I’ll have a fag too please,” Valerie said.

Troy lit her a cigarette and turned around to give it to her.

She kissed him quickly and rubbed her lipstick off his mouth with her finger.

“Did you like that?” she put her cigarette down on the balustrade, found her lipstick, and touched it up by feel.

“Oh god yes Valerie; that is the most amazing thing that has ever happened to me” Troy gushed.

“Here! A souvenir,” she grinned at him and pushed her soiled panties into the kerchief pocket of his jacket where they hung down rather indecently.

She took another hit of his hipflask and picked up her cigarette and took a drag.

“Now I’d look to discuss something you said earlier,” Valerie said.

Troy looked at her questioningly.

“You said earlier ‘God I’d give anything to fuck you.’” Valerie smirked.

“Exactly how much would you give?”

To be continued.

Finishing School For Young Ladies Ch6

Author: 

  • Michele Nylons

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • EXPLICIT CONTENT

Publication: 

  • Serial Chapter

Genre: 

  • Transformations

Character Age: 

  • Teenage or High School

TG Themes: 

  • Disguises / On the Run / In Hiding
  • School or College Life
  • Voluntary

TG Elements: 

  • Bad Girls / Promiscuity
  • Girls' School / School Girl
  • Lesbians
  • Prostitution

Permission: 

  • Posted by author(s)

Saint Trinians_0.jpg

Finishing School For Young Ladies

By

Michele Nylons

Chapter Six – Unintended Consequences

“So what were you doing in the rose garden?” Emily teased.

“None of your business,” Valerie smirked.

“Well that young man looked very pleased. I’d reckon I’d know that look anywhere. I reckon it was the I’ve just been fucked look,” she grinned.

“Well that could be. How was your evening at the Harvest festival Miss Milford?” Valerie smiled back.

“Well I may or may not have been rogered myself,” she grinned.

They were in Valerie’s room drinking bourbon which was a new spirit that Billy Butler was selling and was all the rage mixed with Coca Cola; another new item Billy was flogging.

“But seriously; I didn’t know you were up for it with guys,” Emily said.

Valerie just winked at Emily and thought back to the Harvest Festival dance which was not only a pleasant interlude; it had also provided her with the idea for another business opportunity.

She mentioned the idea to Sally but not the sexual liaison with Troy. That would remain her secret for now.

“So you say this lad from the Bridge Street Academy says that he, and more than likely his mates, would be willing to pay for sex if they could get it regularly and discretely from attractive young ladies?” Sally asked.

“So how did this subject come up? Was his hand up your skirt at the time? Was he offering you money for a shag?” she said amusedly but there was a hint of jealousy there too.

“No! And I wasn’t wearing a skirt I was wearing a ball gown,” Valerie tried to make light of it.

“Well when I worked the streets I often saw snotty young lads from public schools looking for a shag. The prossies would take them for double what they should be paying because the young blokes had no idea how much it really cost but usually the pimps would chase them off because the young toffs attracted the attention of the coppers,” Sally said.

“So there is a potential untapped market in randy wealthy teenage youths who would be willing to pay for sex but don’t have anywhere to get it?” Valerie mused.

“Trust you to think of a way to make a quid out of a Harvest Festival dance,” Sally chuckled.

They both laughed and Valerie put her idea to bed.

But once again a series of unintended consequences conspired to change the direction of Valerie's future.

Returning to school Valerie found Emily Milford heartbroken and almost inconsolable.

Valerie hugged Emily and led her to her dorm where she snuggled up to her on the bed, stroked her hair and kissed her softly on the forehead. Valerie let her cry until she was all cried out.

“What is it sweets? What on earth has happened to you my darling?” Valerie held Emily and gently rocked her.

“It’s my father. He’s bankrupt! He’s bankrupt and destitute!” she sobbed.

“And he’s run away with some slattern!” she broke down again.

“We’ve lost the family home in the Cotswolds. Mum’s living with her sister. Stephen and I are still at our boarding schools but I have no way to pay for next term’s tuition,” she bawled.

Valerie just let Emily cry until she couldn’t cry any more then she got up and poured them both a stiff drink and lit the obligatory cigarettes.

“Stephen is studying mechanical engineering and has an apprenticeship waiting for him next year so he should be ok”

“I’m studying stupid fucking fashion design and liberal arts! For fuck sake I couldn’t even get a job as a shop assistant with those qualifications,” Emily sobbed.

“I’ll pay for it,” Valerie whispered.

“You’ll pay for what?” Emily looked a little shocked.

“I’ll pay for your tuition and board,” Valerie replied.

“No! I won’t accept charity,” Emily snapped.

“It won’t be charity,” Valerie tried to console her.

“What else do you call it then?” Emily countered.

“A loan,” Valerie retorted.

“And how do I pay you back? You going to wait for me to set up my own fashion house? Oh that’s right I don’t have one and I don’t have any money to set one up cause my dad is broke and has fucked off with a strumpet!” she started sobbing again.

This time when Valerie tried to console her, Emily angrily pushed her away. She poured herself a large scotch and lit another cigarette and stared at the table. She was furious and Valerie didn’t know what to say.

“Ha! Maybe I should charge you for shagging me! At least that’s something I’m good at!” Emily quipped.

“Maybe you should,” Valerie replied, pouring her own drink and lighting a ciggy.

“Maybe I should!” Emily sulked.

“Seriously. Maybe you should,” Valerie said candidly.

Emily turned her tear-stained face to Valerie.

“Are you fucking serious!” she looked incredulous.

“I’ll let you into a little secret. My lover and business partner, who just happens to be another transvestite, is also a prostitute,” Valerie drew on her cigarette and allowed the information to sink in.

“Sally started out as a street walker and now she’s part owner of a flat in London that I share with her and which she uses to see select clientele.”

“But she’s still a brass?” Emily said sceptically.

“She likes the work and she likes to contribute to our business,” Valerie replied straightforwardly.

“So you’re telling me that you went undercover as a transvestite and fell in love with a tranny prossie who besides fucking you on the holidays likes to take it up the arse from strangers at five quid a pop!” Emily burst into laughter.

Valerie slapped her across the face. Hard.

“I’m going to forgive you because I love you and I know you are hysterical and mentally unstable at the moment. But if you ever say anything like that again about Sally I’ll slap you stupid. Do you understand?” Valerie was panting with anger.

Emily put her hands to her scalded face and nodded.

“I’m sorry Valerie. All you have ever been is kind and generous to me and I repaid you by saying something I will forever regret.”

Valerie pulled Emily to her and squeezed her affectionately.

“I’m sorry too,” Valerie whispered into Emily’s hair.

They cuddled for a while and then Emily broke free of their embrace and sat on the edge of the bed with her feet on the floor staring at the ground while smoking a cigarette.

“Christine Keeler and Mandy Rice-Davies,” she whimpered.

“What?” Valerie had no idea what Emily was talking about.

“They said they were models but they were really just prossies. They were just trollops really and look how rich and famous they became,” Emily muttered.

“I still don’t get it?” Valerie got up and sat beside her.

“What if I did get men to pay for it. But nice men like your Sally does. You could pay my tuition and board and I’d pay you back in instalments. But I’d need somewhere where I could do it. Just like your Sally,” Emily smiled.

“Are you fucking serious?” Valerie looked her a little dubiously.

“Why not? Just until I’m on my feet. I can stay at school and save enough money to set up my own boutique. I can study during the day and work evenings and weekends,” Emily said quite confidently.

“You can’t. You won’t be able to get away from the school. You might be able to do it once or twice but you will get caught and that will be the end of it.” Valerie sipped her drink and blew smoke at the open window.

“Besides you wouldn’t last five minutes walking the streets.”

“Oh Bollocks!” Emily sounded defeated.

“Unless you had a confidant. A helper. Someone who had someone else who worked for her who had a little cottage on school grounds where you could work from. Someone who had some cash to get you set up. Someone who knew a brass intimately so the brass could teach you the tricks of the trade. Someone who already had a contact in a nice Public School that could provide the right clientele,” Valerie beamed.

“Oh my fucking god! Are you serious?” Emily squealed.

“If you are. It’s an idea I’ve sort of had kicking around but for the life of me I never thought of getting you involved,” Valerie replied.

“Could it work?”

“We can only give it a try,” Valerie smiled.

“Fuck it! I’ve been giving it away anyway. Those fuckers can pay for it from now on if they want it!” Emily sounded quite resolved.

“Do you know what ‘crossing the Rubicon’ means?” Valerie was as serious as she had ever been.

“Yes. It means there is no turning back,” Emily replied sombrely.

Valerie raised her eyebrows questioningly.

“Let’s cross the Rubicon!” Emily set her resolve.

It didn’t take long to set up once they got cracking. Valerie used her business acumen to get things rolling.

Valerie bought Billy The Bottle in on it straight away. Billy cleaned out one of the small rooms in his cottage at the back of school on the edge of the small wood. They decorated it, put in a double bed, put nice bed linen on it and had the room tastefully appointed. Only Billy and Valerie knew that there was also a camera on a tripod installed in a closet so that Billy could secretly take pictures of anything that happened on that bed. Valerie called it her ‘insurance policy’.

They also installed a little buzzer with a button on both sides of the bed that Emily could push if things got out of hand. Billy was to be concierge and security.

They set up a little bar in the lounge. It’s not like they were expecting many punters but they wanted the customers to have a top end of town experience; that way they could charge the clientele more.

Valerie called Troy Bingham at the Bridge Street Academy. Troy remembered her immediately and was delighted she had called.

“Troy. Remember you said that you and a couple of your mates would be willing to pay a decent encumbrance if you could have sex with a pretty young girl in private and with your safety and discretion assured?”

The conversation got to the point and was quickly concluded.

“You are putting in for a weekend pass to stay with Sally and I this weekend. I want you under the tutelage of Sally before you start so she can teach you how to deal with the punters. This is not negotiable,” Valerie said solemnly.

“All right! Keep yer knickers on! What girl wouldn’t like to spend an all expenses paid weekend in London with two gorgeous transvestites,” Emily laughed and snuggled up to Valerie and nibbled on her ear.

As Emily’s fingers slipped into Valerie's knickers she realised what Emily had just said.

“Hey! Who said it was all expenses paid?”

Emily squeezed Valerie’s cock and slipped her tongue into her mouth and Valerie stopped complaining.

Valerie was a little concerned that Sally and Emily might not get along. There was the age difference but she was also thinking there might be some jealousy. She couldn’t have been more wrong. The two hit it off from the start.

“Hello Emily,” Sally beamed when Valerie ushered her into their apartment.

“Hi Sally,” Emily smiled back.

They kissed and looked each other up and down.

“You’re gorgeous!” they said in unison and both broke up in peals of laughter.

They walked arm in arm into the lounge room leaving Valerie to bring up the rear.

“I’ll bring in the bags then shall I?” she called after them.

“And I suppose you’d like a drink each?” she shouted sarcastically.

When they had all settled down with a drink and a cigarette Valerie felt a little awkward for some reason, like a third wheel.

“Why don’t you duck out and do some shopping darling and leave Emily and I to discuss business,” Sally smiled.

Valerie took the hint and gratefully left the two together. She changed into ‘civvies’ and hit the high street.

Sally and Emily sat across from each other, knees almost touching. Sally took Emily’s hands in hers and began.

“First off just remember it’s a business; you’re renting your body for a specified period for a specific purpose. Anything that the punter wants extra you either say no to, or you charge him extra,” Sally began.

The two chatted away for most of the afternoon; Emily had a thousand questions and Sally bought up topics that Emily would never have thought of. They discussed contraception, venereal diseases, to kiss or not to kiss (the decider was usually whether the punter had bad breath), personal hygiene and so on.

“Then there’s the special requests,” Sally grinned and offered cigarettes.

Emily indicated her ignorance with a frown. Sally laughed and went on.

“Some men like a little spanking. Some might want to wear your knickers, some will want you fully dressed, or in lingerie, or fully naked. Some like the light on some like it off. Some like to watch you while they fuck you and some like it doggy. Some might even ask you to fuck them,” Sally explained.

“Yew! Yucky!” Emily screwed up her face.

Then she realised what she had said.

“Oh my god I’m so sorry if I offended you,” Emily touched Sally on the arm.

“Don’t be silly dear. Valerie and I consider ourselves to be women; except we have a penis. Anal sex and fellatio are natural to us.”

“But the point I’m making is you need to make decisions as to how far you will go. What you will do and what you won’t do. And never be surprised about what a man might ask you to do.”

“And always charge extra for it,” Sally giggled and stroked Emily on the forearm.

There was an awkward silence which was broken when the door rattled and Valerie entered the apartment. They were both a little relieved.

Valerie came over and kissed Sally and then went into their bedroom and dropped her purchases on the bed while she took off her coat. She turned around to find Emily behind her.

Valerie smiled at her.

“How was it?” Valerie asked.

Emily stepped forward and took Valerie’s hand.

“Sally is delightful. Wonderful. I can just tell that she loves you so much and that you love her,” Emily gushed.

Valerie blushed.

“I do love her. I love her with all my heart and I’d do anything for her,” Valerie squeezed Emily’s hand.

Sally was standing just outside the bedroom door and when she heard Valerie’s words her heart melted.

“I’ve bought groceries and I’m cooking us dinner. There’s wine in that bag there; be a love and bring it to the kitchen,” Valerie said.

They ate at the table and nattered away, laughing and joking and telling tales about each other. They drank all the wine and started on the spirits. They drank a lot.

The three of them ended up sitting on the throw rugs in front of the fire sipping drinks and smoking. The dishes had been left for tomorrow and all the lights were out; the room was warm and lit only by the firelight.

The topic had of course turned to sex.

“Do you know that one of the first questions Valerie asked me was how I lost my virginity,” Emily said to Sally, more than a little tipsy.

“Wow…now that’s not always an easy question to answer. You know she still hasn’t told me,” Sally gushed.

“Change the subject,” Valerie said soberly.

“But I do know that I took her cherry as a girl,” Sally giggled.

They all broke up at that.

“What’s it like?” Emily asked.

“What’s what like?” Sally looked at her confused.

“You know…” Sally pointed to her bottom and they all broke up again.

“Seriously though. I bet some, what do you call them ‘punter’, will want me to do that to me,” Emily said, splashing gin and tonic into their glasses.

“And I told you. You only have to do what you want to do,” Sally replied.

“But how will I know if I like it if I don’t try it?” Emily gulped at her drink and giggled.

Sally and Valerie looked at each other and shrugged their shoulders and then they smiled at each other.

“Come on little lady,” Valerie got up and helped Emily to her feet.

“Where are we going?” Emily asked looking a little confused.

“We’re going to find out if you like anal sex,” Valerie said leading her to the bedroom.

“Yeah. Ok then. But what about Sally?” Emily stumbled and giggled.

“Oh she’s coming with us,” Valerie smirked.

The three gorgeous creatures knelt on the bed kissing and fondling each other. They had all stripped down to nothing but stockings and suspenders. Emily and Sally’s breasts were about the same size, a nice handful, probably B-cup but it was obvious that Emily’s were just budding and would be quite large before too long. Valerie didn't feel inadequate not having any breasts of her own but she was a little envious.

Not that it stopped any of them kissing, sucking, fondling, tweaking, biting or otherwise stimulating each other’s breasts and nipples. Both Valerie and Sally were sporting full erections. Emily paid attention to Emily’s engorged phallus with one hand, stroking it whilst kissing her and stroked Valerie's hard member with the other.

“Oh my god! Two cocks, no waiting,” she giggled.

Sarah placed her mouth over Emily’s and explored her sweet mouth with her tongue while Valerie explored her vagina, her fingers sliding between the folds and finding her clitoris standing proud of its hood. She stroked the hard clitty and inserted two fingers into Emily’s vagina. Emily gasped and gripped the two cocks in her hands tighter and moved her fingers along the shafts and caressed their leaking glans. She was wet and ready.

Valerie had other plans however; she was in to rush to penetrate or be penetrated. She encouraged the three of them to lie on the bed in a triangle so that Sally could lap at Emily’s cunt, Emily could suck on Valerie’s cock and Valerie could fellate Sally.

Valerie was a considerate lover and allowed Emily and Sally to enjoy each other as much as possible. She sucked on Sally’s throbbing cock, working her lips on the shaft and slathering her tongue along the ridges of her glans, tickling her fraenulum. Sally lapped at Emily’s sopping vulva. She gently opened the outer, then the inner labia and used her tongue to explore the little hard nubbin in its hood. She worked it with the tip of her tongue and Emily literally screamed with delight.

Valerie nodded at Sally and Sally nodded back at her in agreement. Emily was ready.

They quickly rearranged themselves, lying on their sides, making a girl-sandwich with Emily in the middle.

Sally kissed Emily and held her tight, her hard cock probing between Emily’s legs, searching for her warm, moist, cleft. Valerie had taken the tube of KY jelly the girls kept in the nightstand and was generously smearing it into Emily’s puckered cranny. She snuggled up to Emily so that Emily was trapped between the two transvestites. Sally lifted Emily’s leg and placed it over her thigh so that her groin was accessible to Valerie and Sally.

Sally’s penis found the entrance to Emily’s vagina and she thrust forward just as Valerie inserted a finger in Emily’s rectum. Emily squealed with delight at the intense feeling of the double penetration. Sally kissed Emily fervidly as she rutted slowly against her body, ensuring maximum penetration. Valerie used her finger to explore Emily’s rectum; Emily was pushing back against the digit and was obviously enjoying it.

Valerie squeezed lubricant on her erection and removed her finger from Emily’s anus and pressed her glans against the slick, tight, entrance.

“Are you ready?” Valerie whispered in Emily’s ear.

Emily could only nod. She was kissing Sally passionately and had no intention of stopping. Valerie pushed and eased her glans just inside Emily’s sphincter.

“Oh Jesus!” Emily gasped as Valerie’s cock invaded her virgin arse.

Sally clung to Emily and continued to grind her penis in and out of her cunt, ensuring her pubic bone pressed on Emily’s clitty.

“That’s ok baby. Relax. Valerie won’t hurt you. It’s just a little pressure ok?” Sally stroked Emily’s face and then began to kiss her again.

Valerie felt Emily’s sphincter relax and she eased more of her cock into Emily’s tight back passage. Emily was so tight that Valerie had to be careful not to come, she was so stimulated. Sally fucked Emily from the front, her hard cock driving in and out of Emily’s juicy sheath; there was no doubt that Emily was extremely stimulated.

Valerie continued to slowly guide herself into Emily’s behind until she was in all the way and her groin rested on her soft buttocks. She smiled over Emily’s shoulder at Sally and nodded and the two transvestites began to fuck the girl between them.

Emily couldn’t do much but lie between the two girls and luxuriate in the intense sensations radiating from her vagina, her anus, and her clitoris; she was in state of intense stimulation and excitement. She began to scream and Sally smothered her cries by kissing her and fucking her as hard as she could; it was like hanging onto a bucking animal.

Valerie was hanging onto Emily from behind, her arms locked around Emily’s waist as she jackhammered her cock in and out of Emily’s tight anus.

Emily came like an express train. She screamed and writhed and all that Valerie and Sally could do was hang on for the ride. They both came inside Emily simultaneously and they too moaned with ecstasy as they orgasmed.

The three sumptuous creatures were a tangle of stocking-clad legs, sweaty bodies and languid arms and hands groping and stroking each other. They shuddered and writhed against each other until they were spent and sated and then lay in a muddle of perspiring limbs and laddered stockings, they gasped and panted as they regained their composure.

Once they had recovered enough to talk, Emily was the first to speak from the centre of the sex sandwich.

“Oh my god the most amazing sex and the most intense orgasms ever,” she sighed.

“Orgasms?” Sally queried.

“Yes orgasms. I lost count at two,” Emily giggled.

“Fucking women! Always getting more than us and then rubbing it in!” Valerie laughed.

“Well I can tell you one thing ladies. I’m definitely not closest to either the bar or the cigarettes so unless you want to keep me trapped between you and shag me again, one of you has got to move,” she chuckled.

“Age before beauty,” Sally joshed.

“Fuck you two! I need to piss anyway,” Valerie reluctantly broke away from the threesome to pee, pour drinks, and get their cigarettes.

When she came back she found Emily and Sally in the 69 position.

“Hey fuck you two! Wait for me!” she put down the tray with the drinks and packets of ciggies and leapt on the bed.

To be continued.

Finishing School For Young Ladies Ch7

Author: 

  • Michele Nylons

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • EXTREMELY EXPLICIT

Publication: 

  • Serial Chapter

Genre: 

  • Transformations

Character Age: 

  • Teenage or High School

TG Themes: 

  • Disguises / On the Run / In Hiding
  • School or College Life
  • Voluntary

TG Elements: 

  • Bad Girls / Promiscuity
  • Girls' School / School Girl
  • Prostitution
  • Shopping

Permission: 

  • Posted by author(s)
Saint Trinians.jpg

Finishing School For Young Ladies

By

Michele Nylons

Chapter Seven – Bethany

Valerie lay in bed fast asleep. As usual she was dressed in a satin negligee, nylon panties, satin brassiere and had left on her stockings having had sex just before falling asleep. She was enshrouded in satin sheets and enraptured by the feel of the silky, slinky, feel of her lingerie cosseting the bed linen.

The feel of the gossamer-like garments against her sensitive flesh invoked memories which pervaded her dreams.

She dreamed of being William Styles, at home between school terms, alone with his stepmother; his stepfather as usual away on some errand for Big Tony.

William stood in the doorway to his mother’s bedroom watching her trim figure; her back to him as she slid her panties up her stocking-clad legs and smoothed them tightly around her buttocks. She, turned her head and saw him there and she smiled. She extended her hand, beckoning him into her bedroom.

“I know you like seeing me like this William. Come closer and take a good look,” her smile widened.

William stepped into the bedroom and closed the door. There was no one else in the house but it seemed the right thing to do.

“Here,” Bethany Styles, his stepmother offered her hand to him.

Her fingers were long, her nails were long too and manicured and painted bright red. He liked her fingers when she stroked him or scratched his back or even just held his hand or touched him.

“What do you like the most William? Is it my stockings? Here feel them,” she guided his fingers to the dark welt at the top of her stocking.

“Feel the little black seam that runs down the back of my leg William,” she took one his fingers and drew it along the backseam of her stocking.

“Now put your fingers back on the welt; see how smooth and gauzy if feels and see how much darker it is to the rest of my stocking. These little silver clips on my suspender belt are called garter snaps and they help hold my stockings up.”

William’s hand rested gently on her thigh.

“Now look how creamy your mother’s skin is above the welt and feel how soft it is to touch,” she guided his fingers to the snow-white thigh flesh above the welts of her stockings.

William’s penis was erect and uncomfortable in his underpants but he was too scared to adjust it.

“And if your fingers follow the garter strap you will see they are tucked under my knickers so I can pull them up or down without removing my stockings. Do you want to touch my panties William? Do you want to feel how soft my knickers are?”

William’s mouth was dry and he couldn’t speak but he nodded ever so slightly.

“Here, run your hands across the globes of my buttocks; feel how satiny and sleek they are. My knickers are very tight there but see how they wrinkle just a little bit in the cleft of my buttocks. Put a finger in there and feel how cool and plush that feels,” She smiled down at him; with her red lipsticked lips and beautiful blue eyes.

“But I know where you really want to put your fingers don’t I William. You want to put them here don’t you?” his mother moved his fingers to the front panel of her panties.

“Feel how tight they fit. Feel how flat my tummy is and how my pubis curves down. Here feel it,” she guided William’s fingers across the front panel of her tight, slick, knickers.

“Do you like the colour? Do you like my white satin panties William?”

“I know you do. I know you like my stockings too because I’ve found the little silver trails you left on them when put them on your cock. You’ve been wanking with mummy’s panties and nylons haven’t you William?”

William’s face burned with shame. He was eighteen yet he felt like a little boy.

“It’s ok darling. I’m not really your mother. I’m your stepmother and you are of the age of consent. What we are doing isn’t illegal. It’s naughty but it’s not criminal,” her smile widened.

“So you can touch me here,” Bethany grinned and pushed his fingers against her sex.

William felt the soft folds of her vagina through the gauzy material. Most of the knickers in her bedside drawer had a cotton gusset in them; but these didn’t, they were delicate and translucent and he could feel every part of his mother’s sex.

“Feel how sheer the material is, and see here how they have become translucent where my juices are soaking into them. You are making me wet my knickers William; your fingers touching me through my knickers are making me wet.”

“And I can see you are becoming wet too. Look!” she directed him down to the little wet patch on the front of his trousers.

“Here. Let me help you with that.”

His mother unzipped his fly and freed his hard cock; she held it gently between her cool fingers.

“This feels so good doesn’t it William. Of course we can’t tell daddy but it feels so good. We need never tell daddy anything. It will be our secret.”

His mother squeezed his penis and he ejaculated. His sizzling semen splashed on his mother’s stockings, the white globules contrasting with the black diaphanous nylon. More of it spurted from the eye of his cock; a rope of the gelatinous issue spattered on the dark welts, another splashed across the front of her knickers and his mother gasped.

Bethany Styles closed her eyes and shuddered as she orgasmed. Her husband hadn’t touched her for nearly a year and she knew her stepson was fantasising about her. She’d found the evidence in her lingerie drawer. She was so sexually frustrated that she needed this release.

When William had finished; Bethany squeezed the last little globules of his issue from the eye of his cock and collected it with her fingernail. She wiped it on her stocking.

Bethany zipped her son’s fly and pointed to the door.

William left the bedroom and closed the door behind him.

Bethany collapsed on the bed and sobbed; wracked with shame and guilt.

Valerie woke up and found that she had had a nocturnal emission; the front of her knickers were soaked. She had had that dream again.

Sally was sound asleep beside her and Emily lay on the other side of Sally. They had slept three-in-a-bed for the last three nights and Valerie was surprised that she’d had the wet dream. She’d had so much sex lately she didn’t think she had it in her.

But that dream. That dream that wasn’t really a dream; it was a memory, and it never went away. Not since her mother had died.

Valerie lay there and remembered the second part of the dream. Where William’s mother came to his bed that night dressed exactly like she had that afternoon. He was naked and his erection was tenting the sheet as he thought about what had happened in his mother’s bedroom.

Without a word Bethany had slid under the sheet and pressed her body against his. She had kissed him and her stockinged thigh had brushed against his penis and he had spontaneously ejaculated. He had tried to apologise but she wouldn’t hear it. She said it was ok. She kept her lips pressed to his and put her tongue in his mouth at exactly the same moment that she had put his erect penis into her warm moist sheath.

She lay on top of him, her breasts pressed against his chest, her tongue examining his mouth, her sleek stocking-clad thighs pressed against his as she slowly gyrated her pubis eliciting another orgasm from her son, this time at the same time as her own. He ejaculated deep inside his mother and felt her vagina palpitate and contract and milk him of his seed as she shuddered against him in the throes of her own climax.

She lay on top of him; her head on his chest listening to him breathe, kissing his warm flesh. He felt her hot breath on him and god if he didn’t become tumescent again.

He probed between her thighs but she shook her head and whispered “enough” and tried to roll away.

He pushed her down on the bed and forced her legs open. He pushed her panty-crotch aside and impaled her on his turgid weapon. He fucked her hard and fast and she wrapped her nylon-sheathed legs around him and rutted with him, milking him of his seed a final time.

She left his bed without saying a word.

The next day she was gone. Gone to join her husband on that fatal flight.

Valerie shook the memory from her consciousness. She got out of bed and headed to the bathroom where she used the toilet, brushed her teeth and showered. She put on some makeup and brushed her hair then she threw on a robe and came back the bedroom.

The room reeked of sex, booze, and smoke and it was obvious that Sally and Emily had just finished another session. They were both flushed and panting.

“Fuck me, I’m coming back with a bucket of cold water if you two don’t stop it and get out of bed,” Valerie joked.

“It’s not my fault. Emily wanted to be absolutely, positive that she enjoyed anal sex,” Sally quipped.

Emily blushed.

“Yeah it’s my fault. I lay here with my bum up in the air begging for it up the wrong ‘un,” she squealed with laughter when Sally hit her with a pillow.

“Get up you two. I’m making tea and there’s shopping to be done,” Valerie turned to go.

“My favourite pastime after sex!” Emily bounced out of bed and padded to the bathroom.

“That girl is a fucking-machine,” Sally said to Valerie.

“You’re telling me? I live across the hall from her!” she grinned and sauntered off to make the tea.

They went shopping with Emily and bought her sexy lingerie, boxes of condoms, tubes of lubricant and various ladies sanitary products. They also bought her a fully stocked cosmetics case to keep in her ‘work room’.

“Being a whore is just like any other profession really. You need the right tools of the trade and to keep yourself fit and healthy,” Sally elucidated as they sipped tea during a break from shopping.

“Wow. I haven’t really thought of myself as a ‘whore’ as such,” Emily said.

“Well you can use words such as hostess, escort, companion; whatever floats your boat really. At the end of the day you’re fucking guys for money,” Sally said prosaically.

“Wow you make it sound so romantic,” Emily turned down her mouth.

“Look honey. It’s just a business. You need to make money and keep yourself safe while you do it. If you enjoy it now and then, then that’s a bonus ok?” Sally replied.

Valerie nodded.

“The Rubicon; remember?”

Emily nodded in return.

Back at the Finishing School they got ready for Emily’s debut. Troy Bingham said he was excited to be taking advantage of the business proposition and had two other students from the Bridge Street Academy that would like to sample the wares being offered.

They liked the fact that it was a young lady from a reputable college, that she had a discreet venue, and that it was safe. The lads had been sowing their wild oats with streetwalkers, which they found distasteful and dangerous, or paying exorbitant fees to call girls as well as having to pay for hotels.

Emily sat on the edge of the bed dressed in a see-through negligee, translucent black panties, matching bra, black lace suspender belt and fully fashioned stockings. Her highheels were so ridiculously high she could hardly walk in them but then again “they are not for walking in, are they?” Sally had explained when they bought them.

She was wearing a lot of makeup, ruby-red lipstick, rouged cheeks lots of black eyeliner and mascara and blue and pink eyeshadow. Her hair was teased and worn big.

Troy had the use of his father’s car and had driven his friends to Chelmsford; the lads nervous and joking and drinking from a bottle of Johnny Walker. They had been instructed to bypass the main entrance to the school and take the tradesman’s entrance to the gardener’s cottage.

They were even more nervous when the countenance of Billy ‘The Bottle’ Butler appeared at the door dressed in a suit looking like a nightclub spiv. But he was quite friendly and engaging with the lads, offering them a drink and seating them comfortably in his little sitting room.

“Right. Whose first then lads, we didn’t come here for a haircut now did we?” he winked.

Troy Bingham leapt to his feet. He had insisted on the drive down that he go first as he had arranged the ‘Tom’ and it was his dad’s car they had used to get here. He was a little nervous when Billy waved a hand at the bedroom door but his nerves dissipated when he saw Emily sitting on the bed.

Emily was more nervous than he was, that is until the handsome young man entered the room and closed the door.

“Hello, I’m Troy,” he introduced himself.

“Hello, I’m Molly,” Emily had no intention of using her real name.

“I have to say you are very lovely Molly. So much different to the brasses I’ve been with before. I have to say I’m a little nervous,” Troy explained.

“Well looking at that bulge in your pants, you at least know what you’re here for love. Why don’t you get undressed and join me?” Emily smiled.

Although Emily was nervous, Sally had instructed her well, explaining it was all just a routine. Get them comfortable, get them undressed, get them off, get their money and get them out the door, was her philosophy.

Troy stripped off and sat next Emily nervously looking at the floor.

“Err…what can I do and what can’t I?” he asked.

Emily just pulled him down on the bed and kissed him. She slid underneath him ensuring his manhood rubbed on her silky lingerie. She slipped her tongue into his mouth and gripped his hard cock and gave it a few tugs and then opened her legs and slipped him into her.

She had pre-lubricated herself with KY jelly and he slid in quite easily.

“Oh my! This is quite wonderful!” Troy gasped as he fucked the pretty young girl lying underneath him.

Emily wrapped her legs and arms around the youth and kissed him again; rising up off the bed to meet his thrusts.

Troy’s screwed up his face in exhilaration as he released himself inside the beautiful young prostitute. She encouraged him; grinding against him and raking her heels along his flanks like a racehorse.

Emily laughed to herself as he apologised for coming so quickly as he pulled on his pants. He scrambled for his wallet.

“No. Not here. Pay Billy outside silly,” she admonished him.

Troy blushed and stumbled from the room.

The other two youths turned to face him expectantly.

“How was it?” they asked in unison.

“Bloody fantastic!” he grinned.

Emily was chuckling to herself. She cleaned herself with tissues and then she saw the unused condom still sitting on the bedside table.

“Fuck! I knew I’d forgotten something,” she chided herself.

She fixed her makeup and sprayed perfume on herself and lubricated her snatch. She flicked a switch and a little red light came on above the door indicating she was ready for her next punter.

“Right! Whose next then lads?” Billy grinned.

Emily took care of the other two lads pretty quickly. One wanted to come in her mouth as he had never experienced fellatio before and the other shagged her up against the wall. She was surprised when Troy came back into the room a second time.

“That first time was so good I want to do it again,” he grinned.

Emily couldn’t help but grin back at him.

“You were supposed to put a johnny on that first time and I forgot. I would say that any damage has been done so you can go again without one I suppose,” she smiled at him.

This time he was able to take his time and Emily quite enjoyed it and was close to coming herself when Billy banged on the door.

“Time’s up I’m sorry,” Billy yelled through the door.

“Tell him I’ll pay double. I'm really close,” Troy panted as he feverishly pumped away at Emily.

“Tell him yourself!” Emily giggled.

“I’ll pay double!” Troy yelled at the door.

“Suit yourself sir. A double it is sir,” Billy shouted back.

“Right. That’s taken care of, now finish me off mister,” Emily grinned up at Troy and wriggled her crotch and pushed up against him to encourage him.

Emily and Valerie sat on Billy’s overstuffed couch while he sat in the matching lounge chair counting cash.

“Fifty quid!,” Billy waved the readies.

Billy took ten, Valerie took twenty, which left Emily with twenty pounds.

“Not bad for a little under two hours work. The average weekly wage is about forty quid!” she grinned.

“Easy work at that,” she clinked her glass against Valerie and Billy’s and sipped her G and T.

Word got around the colleges and posh schools that a pretty young student was selling it at Chelmsford Finishing School for Young Ladies and what started out as a three men a night, three nights a week venture quickly became full time employment for Emily after work and weekends. She was making a lot of money but her personal life was becoming unmanageable.

Valerie was lounging on her bed one evening smoking a cigarette and reading a fashion magazine when there was a tap on the door and Emily walked in with Alice Corinda and another girl that Valerie recognised but didn’t know too well.

Valerie was a little surprised to see the three of them.

“What can I do you ladies?” she asked.

“Well…it’s kinda what we can do for you,” Emily replied.

The other two girls looked awkward and were blushing.

“Come in, close the door and sit down. This looks find of serious,” Valerie said.

The two other girls sat on the couch and Emily sat next to Valerie on her bed.

“So it’s like this. I’m wearing my twat to the bone in the cottage every night. It’s got to the stage I can’t keep up with demand. My grades are suffering and I don’t have a life other than studying and fucking for money,” Emily said.

Valerie’s face became stormy. Everyone involved in her enterprises were sworn to secrecy.

“Look. Some of the girls have noticed that I have lots of new clothes, the latest cassettes and records, and plenty of cash. They aren’t stupid and they know my family is broke,” Emily continued.

Valerie frowned but let her continue.

“There’s a fucking recession for fuck sake and most of the girls here, even though their parents are reasonably well off, are feeling the pinch.”

“So a few of them have approached me and asked me how I’m making money. It’s not hard to figure out; what else could I be doing and a lot of them are fucking like bunnies anyway. So…I told those I trust…please don’t get mad…and only those I trust, that I’m on the game.”

Valerie nodded sagely.

“Look I haven’t told them the details of course. All they know is that I’m selling my arse and making quite a few quid from it,” Emily looked very reticent.

“Ok. You two; wait in the bog. Here; keep yourselves amused while I talk to this one,” she tossed a packet of cigarettes at Alice and nodded sternly at the door.

“What the fuck Emily?” Valerie said when the others had left.

“I told them about the Roman river thing!” Emily cried.

That broke Valerie up.

“Ok, ok, I get it,” Valerie chuckled.

“I’d actually been ruminating on expanding the business. Sally and I are doing ok from her prossing herself and my business with Billy selling contraband is booming. My deal with you is making money too but you are right, there is more potential in this school to be realised.”

“So here it is. I’ll renovate a second room in Billy’s cottage so the three of you have a place to work. You will have to teach the girls the ropes but I’ll spring for their set up like I did with you; lingerie, stockings and toiletries, although you girls can share cosmetics and a lot of other stuff in the cottage.”

“Billy still gets his cut and of course I get mine. Those girls better realise that we are not fucking around and this is a serious business and they are sworn to secrecy. Also that they can’t let their grades drop or do anything that will bring attention to them,” Valerie pronounced.

“Oh thank you so much Valerie!” Emily squealed with delight.

“Don’t get your knickers in a twist. We still have a bit to sort out yet,” Valerie said.

“And Alice Corinda? Really? Isn’t she a bit of a Muppet to be doing this sort of thing?”

“Hey Valerie, that girl has street smarts, she had Harry Cartwright wrapped around her fingers,” Emily replied.

“Ok. I’ll get started getting the gardeners cottage renovated and Billy on side. I’m going to write up contracts for those girls too. This is getting quite complicated now,” Valerie said.

Valerie had Emily bring in Alice Corinda and Mary Batty and she read them the riot act.

“I take it Emily has explained how this works. In fact Emily has told you too much already, but I tell you this. You keep this secret or Billy ‘The Bottle’ Butler will come calling ok?” Valerie said gravely.

The girls nodded solemnly.

“Ok. That’s the warning done, now sit down and Emily will pour us all some drinks and we’ll talk about this like civilised young women,” Valerie smiled.

And so it eventuated that after eighteen months as a student at Chelmsford Finishing School for Young Ladies, Valerie Swindon had progressed from timid new girl, still learning to be woman let alone a student, to entrepreneur extraordinaire, running contraband and a brothel.

Valerie took a weekend pass to be alone with Sally for a while. They enjoyed having Emily stay but they appreciated having time to themselves.

They were having a lie in on Sunday morning, drinking tea and reading the newspapers when Valerie commented to Sally out of the blue.

“Where did you get your tits done and how much did they cost?”

Sally looked over her newspaper and peered at Valerie.

“Seriously?” she asked.

“Seriously!” Valerie replied.

To be continued

Finishing School For Young Ladies Ch8

Author: 

  • Michele Nylons

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • EXPLICIT CONTENT

Publication: 

  • Serial Chapter

Genre: 

  • Transformations

Character Age: 

  • Teenage or High School

TG Themes: 

  • Disguises / On the Run / In Hiding
  • Lesbian Romance
  • Romantic

TG Elements: 

  • Bad Girls / Promiscuity
  • Breasts / Breast Implants
  • Prostitution
  • Wedding Dress / Married / Bridesmaid

Permission: 

  • Posted by author(s)

Finishing School For Young Ladies
By
Michele Nylons

Chapter Eight – Passport To Eternity

“So are you seriously thinking about getting tits?” Sally dropped her newspaper and snuggled up to Valerie.

“But I thought the whole tranny deal was only for two or three years? Just until Tony stopped looking for you?” Sally said inquisitively.

“Well it was. But now I don’t want to live any other way. I can’t tell you everything right now but becoming a transvestite has answered a lot of questions that I had about myself. I love being Valerie; I can’t imagine being anybody else. William is just a distant memory,” Valerie said.

“But getting breast implants. That’s a huge step. That really is crossing the Rubicon, as you like to tell your school friends,” Sally sounded concerned.

“Well there is one other thing that I’ve been meaning to tell you. In fact I should have told you long before now,” Valerie said seriously.

“Ooh! This doesn’t sound good,” Sally said earnestly.

“I have to tell you I’ve fallen in love with someone,” Valerie said.

Sally paled. She half expected something like this would happen. Valerie was twenty and she was beautiful; someone was going to fall for her or she was going to fall for some young handsome bloke.

“Anyone I know?” Sally tried to smile but she looked genuinely downhearted.

“You might.”

“It’s this thirty-something brass who lives in a flat near Soho. She’s a good looking sort with a heart of gold and I fell in love with her ages ago but I was too stupid to tell her,” Valerie smiled.

Sally began to cry silently and Valerie pulled Sally to her and cuddled her and gently kissed her.

“Have you told her?” Sally baited her.

“Very recently,” Valerie smirked.

“What if your love isn’t reciprocated?” Sally teased.

“Then I guess I’ll just have to make do with you,” Valerie giggled.

“Oh you fucking bitch!” Sally leapt on Valerie and they play-fought for a little while.

Then their fighting turned to cuddling and caressing. Valerie lay on top of Sally kissing her; her hard cock rubbing against Sally’s through two layers of silky knickers.

“Mmm, I like Sunday mornings,” Sally grinned.

“You still haven’t told me about these luscious things,” Valerie freed Sally’s tits from her bra and began to nuzzle them.

“Mmm, well they work just like real ones but don’t give milk,” she joked and pressed Valerie’s mouth to them.

Valerie tweaked one of Sally’s nipples between her finger and thumb, and sucked and gently nibbled the other one. She rubbed her cock against Sally at the same time and was pleased when Sally began to writhe with lust beneath her.

Sally was getting impatient and trying to goad Valerie into penetrating her but Valerie took her time kissing and caressing her lover and bringing her to the edge with frottage.

“Fuck me you bitch,” Sally looked up into Valerie’s green eyes.

“That’s a nice way to talk to the woman who loves you,” Valerie smiled down at Sally.

Valerie eased Sally’s knickers aside and prodded at her puckered bud with her erect penis, deliberately teasing Sally. Sally whimpered and grasped Valerie’s erection and placed her glans at the entrance to her anus.

“I love you,” Valerie whispered and pushed her cock inside Sally’s sphincter.

Valerie slowly pushed herself all the way into her lover and Sally lifted her legs to assist. Valerie placed Sally’s ankles either side of her head so she could reach down and kiss Sally while fully penetrating her.

They fucked like that until they were both ready to come then Valerie locked her lips on Sally’s and thrust vigorously and deeply into her until she orgasmed. Sally came against Valerie’s belly and the two lovers fucked and caressed and kissed until they were totally satisfied.

They lay in bed, a tangle of limbs, and kissed and petted and spoke of how much they loved each other until it was time to do it all over again. This time Sally mounted Valerie, who wanted to lie on her belly and feel Sally’s body pressed against her back while they fucked.

They even showered together and did their makeup side by side in the ensuite bathroom.

“We’re like a married couple,” Valerie joked.

“Yeah; we almost are. We know each other so well we might as well be married,” Sally chuckled.

Valerie looked at Sally in the mirror and took her hand.

“I really do love you Sally,” she whispered.

Sally lowered her head to Valerie’s shoulder and mewed.

They sat at the dining table having brunch dressed only in knickers and bra, the flat was warm and the sun was shining in the window.

“So where were we? Oh yes. So tell me about yer tits,” Valerie’s witticism disguised her genuine curiosity.

“So as I told you I’ve been living as a transvestite since I was seventeen; well it wasn’t until I was twenty five that I’d saved enough money to get the job done. By then I knew I was going to live the rest of my life as a woman so I had no qualms doing it,” Sally began.

“It cost me everything I had at the time to fly to Thailand and have breast implants. It was awful because I had to travel on my male passport and I hadn’t been a man for so long I’d almost forget how to be one.”

“Coming back home I was this guy with long hair who had sprouted tits. A lot of people at the airport stared at me and those cunts at Customs singled me out and strip searched me,” Sally was angry even now.

“But it was worth it. I love my tits,” Sally beamed, pushing her breast up with her hands.

“They’re just the right size for me. A lot of trannies go and get the biggest ones they can…double Ds and shit, and they look awful. They look like drag queens,” Sally screwed up her face.

“So note to self. Don’t get double Ds,” Valerie quipped.

“If you try to get breast implants here in the UK it will take years being on some stupid sex reassignment register, seeing psychs and doctors who think that gender dysphoria is a myth anyway. That’s why most girls go to Asia or Europe to get them done,” Sally finished her tale and bit into her toast.

“So? You thinking seriously of getting tits then?” Sally said around a mouthful of toast and tea.

Valerie sat in the gardener’s cottage that evening sipping scotch with Billy and Billy’s ‘friend’ Raul.

“You know all the faces and geezers around here Billy. Where would a girl who has a bit of cash go to get a decent bit of forgery done?” Valerie asked, sliding a twenty across the table.

An amateur forger herself, the next day at school Valerie produced a letter ‘from her father’ requesting she be given the day off school to meet him in the city as he had returned from Asia and was in London for the day.

Valerie poked her head out of the taxi window and looked around.

“Are you sure this is it?” she asked the cabbie.

“Yes luv; this is it. Are you sure you want to get out here?” the cabbie replied.

“I’ll tell you what. Be back here in exactly half an hour and there’s a two quid tip guaranteed ok?” Valerie opened the door and stepped out of the cab.

The cabbie nodded and drove away in a cloud of diesel fumes.

Valerie stood out the front of a dodgy looking dilapidated building in a back street of Moulsham. She checked and rechecked the address Billy had given her and this was definitely it. The alley was dark and strewn with abandoned shopping trolleys, junk food wrappers, empty beer cans and bottles, cigarette butts, and condom wrappers.

Valerie turned down the alley and her heels click-clacked on the dirty cobblestones.

“Jesus!” she hissed.

She passed a doorway where a prossie wearing a stained leopard skin mini dress with her tits nearly falling out of it, laddered black fishnet tights, and scuffed black high heels with smudged makeup and dishevelled hair was on her knees fellating a man in a business suit.

The man looked mortified at being caught but the prossie didn’t miss a beat; she just kept sucking away, ignoring the sound of Valerie’s footsteps.

Valerie knocked on a door caked with fading and peeling blue paint. When it wasn’t answered she knocked again and this time it opened a crack and she could see someone peering at her.

“What the fuck do you want girlie?” the man hissed through the door.

“Billy The Bottle sent me. He told me that you were expecting me,” Valerie replied.

The man opened the door and invited Valerie in. He looked up and down the alley and closed the door.

“I’m going to be up front luv. I normally wouldn’t touch this job with a barge pole but I owe Billy a big favour so I’ll do it,” the man said tossing a cigarette into his mouth.

“Also…I don’t believe in coincidences but believe it or not this is the second time today I’ve been asked to knock up a passport for a tranny…er I mean…er a transgendered person. I don’t suppose you know Candi Pops do you?” he lit his cigarette.

“Yeah! All us trannies know each other. It’s like a big club where we meet every Saturday night and braid each other’s hair and talk about how many cocks we’ve sucked,” Valerie rolled her eyes sarcastically.

“All right! All right! Keep yer knickers on!” the man said exasperated.

“It’s not exactly cock in a frock central here if you know what I mean; and two trannies in one day? Well who’d have believed it. Anyway what can I do for you luv?” he asked.

“Anyway, who said I was a tranny?” Valerie glared at him.

“Oops sorry darling. Billy told me the job was to knock up a passport for a tranny so I thought it was for you. You don’t look like one if I may say so,” the man gave her his best smile.

“Well I am and now you’re only the third person to know that,” Valerie snapped.

“Jeez I can’t win a fucking trick today. Every time I say something I put me foot in it. Anyway I’m John Benstead,” he offered his hand and the killer smile got bigger.

John was good looking and cocksure of himself and Valerie couldn’t help but smile back at him.

He looked to be in his early forties. He had stylish long blonde hair and was tanned and muscular. He was wearing a pair of tight jeans and tighter T-shirt. His cigarette hung out the corner of his mouth but he managed to smile around it.

Valerie had rummaged around in Sally’s apartment while she was out and found Sally’s passport. It was in the name of Brian Macintosh. Sally had kept her male surname for convenience. Valerie did not recognise the man in the passport photo as Sally and was not interested in him. She had also found the faded copy of Brian Mackintosh’s birth certificate.

Valerie didn’t have a passport but she had a copy of her own birth certificate. She also had two Polaroid photographs of Sally that Emily had taken with her Land camera.

Valerie had used the ruse that she was supposed to be meeting her father today so she had had to dress appropriately. She wore the same outfit she had worn to her school interview. The navy blue pleated A-line skirt with the hem resting mid-thigh, a white nylon long-sleeved blouse, and a navy blue blazer that hung to her hips, wedge-heeled Mary Jane’s with the strap over the instep. White semi-opaque tights and silver necklace, bracelet, earrings and a ring on the ring finger of each hand. A simple black leather-banded watch was affixed to her right wrist.

She knew she would be having her photo taken so she had worked on her appearance; the blunt cut classic bob had been shampooed, conditioned, and given the obligatory one hundred brush strokes.

Her makeup was subtle, some foundation, powder, a dab of rouge, a sparing amount of eyeliner and eyeshadow but plenty of mascara. Her pink lipstick matched her nailpolish. She had completed the ensemble with a subtle splash of perfume.

She could sense John’s eyes on her.

“Anyway; to business shall we?” Valerie said.

John smiled and indicated a ratty chair facing a large desk with a chair well and a chest of drawers on either side. On top of the desk, papers were strewn everywhere and there were various stamps, ink pads, pens, glue, scissors and an abundance of office supplies.

Valerie sat and deliberately allowed her skirt to rise up her thighs and smiled when she saw John’s eyes follow.

She threw the documents she had bought with her on the desk.

“It’s all there. I want passports and birth certificates for Valerie Swindon and Sally Macintosh; the details are in the envelope. You can take pictures of me but you will have to make do with the Polaroids for Sally, it’s a surprise for her.”

John picked up the Polaroids and scanned them.

“Yeah I can make them work. This won’t be cheap; plus it’s off the books if you know what I mean. Half a monkey,” he lit another cigarette.

“Two hundred and fifty pounds; fair enough. I take it you want cash?” Valerie opened her purse.

“I’ll pay up front and Billy will pick up the finished products for me.”

“You’re very trusting,” John tried using his charm again.

“I don’t need to be; I’ve got Billy The Bottle working for me,” Valerie grinned back at him.

“Well yeah…I see,” John paled a little.

“Right get yourself against that back wall where the sheet’s hanging,” he walked over and picked up one of his cameras and adjusted it.

“Good. Look this way and give us a smile,” he aimed the camera and took half a dozen shots, some with a flash and some without.

“Right all done; should be ready in week,” John said.

Valerie still had the money in her hand and John put out his hand for payment.

“You’re really cocksure of yourself, aren’t you?” Valerie examined him.

He just shrugged his shoulders confidently.

“You’re the type that fucks ‘em and forgets ‘em aren’t you?” she grinned at him.

He shrugged his shoulders again.

“Well this time it’s going to be the other way. I’m going to give you the shagging of your life and then I’m going to forget all about you,” Valerie said soberly.

She reached out and with one swipe of her hand she wiped everything off his desk onto the concrete floor. She pierced him with her eyes as she backed up to the desk and hiked herself up on it.

She lifted up her skirt, pulled down her knickers and ripped open the crotch of her tights and tore away her gaff.

John stood mesmerised.

“Are you going to fuck me or are you too scared to fuck a tranny?” Valerie smiled up at him.

John dropped his pants and underpants, his cock poked out in front of him erect and ready.

He approached Valerie and lifted her legs and positioned himself between them. He kissed her ankle and rubbed the opaque fabric against his cheek. His cock was rubbing on her leg, the white translucent nylon became transparent where his precum dribbled on her thigh.

“Come on fuck me. I’m in a hurry,” Valerie teased him.

Her own cock tented the front of her tights and was also leaking pre-seminal fluid.

John slid his cock into Valerie’s anus and he leaned down and kissed her. He cupped her buttocks and plunged his cock in and out of her tight arse and Valerie lifted her bottom off the desk to meet his thrusts. She wrapped her legs around him and fucked him, writhing underneath him; kissing him lustily when he bent over her to do so.

He came; holding her down on the desk, jackhammering his cock in and out of her while he howled with pleasure. Valerie stroked her cock and flooded her tights.

When they had finished fucking, John picked up the box of tissues off the floor and wiped Valerie and himself.

Valerie stood and pulled up her knickers and straightened her skirt and blazer while John pulled up his underpants and jeans.

John went to kiss her but Valerie turned her face so that his kiss landed on her cheek.

She held out the cash she had taken out earlier and offered it to Steve who snatched it out of her hand.

He escorted her to the door.

“I’ll send Billy around in a week then to pick up the documents?” she smiled at him.

John nodded. He was confused. The gorgeous young tranny had come on to him and now she was cold as a fish.

“You’re not as good as you think you are John. You better get your shit together if you’re hoping to get together with this Pops woman,” Valerie gave him a disparaging smile and stepped through the door.

The street walker had finished with her punter and standing in the doorway smoking. She held a bottle of gin wrapped in brown paper. She took a slug and eyed Valerie suspiciously as she passed. The prossie let out a cackle.

“You’re not as good as you think you are, you stuck up bint!’ the crone shouted.

“That’s funny I just told that bloke in that warehouse the same thing,” Valerie chuckled.

Her taxi was waiting and she was glad to see the back end of Moulsham.

Valerie had the rest of the day off so she called Sally and arranged to meet for dinner. Sally was a little grumpy as Valerie had been paying a lot of attention to her businesses; Billy’s contraband and Emily’s whores. It didn’t help that Valerie had to go back to school that evening.

“Valerie! You’re fucking twenty years old now; why are you still at the Finishing School?” Sally asked; she’d had a few glasses of wine with dinner.

“Well it’s complicated Sally. I just need to make sure I’m safe before I come out of hiding and also I’m making good money out of the place,” Valerie tried to placate her.

“I really don’t have to leave until I’m twenty one if I don’t want to.”

This made Sally a little angrier.

“I hardly see you except for the holidays. I love you and I want to be with you,” Sally was getting a bit teary.

“Babe; I’ve got a term holiday coming up and I promise we will spend the whole of it with you. You’ll love it I promise,” Valerie took her hand and squeezed it.

Valerie had been working away behind the scenes making bookings and sorting out every detail of their surprise holiday.

On the first day of her holidays Valerie went home to the flat she shared with Sally.

They made love of course but Valerie turned in early, much to Sally’s chagrin. Valerie got up really early and was super excited. She pottered and banged around the flat until Sally couldn’t stand it any longer and she got out of bed.

Sally came into the living room and found two suitcases in the centre of the floor and Valerie standing between them in travelling clothes grinning. She was holding some documents up and waving them.

“Surprise!” Valerie shouted and hugged Sally.

Sally was still half asleep and when Valerie dropped the documents in her hand she was surprised to see they were airline tickets. They were airline tickets to Bangkok.

“You’re coming with me while I get my boobs done and then we’re having a holiday,” Valerie gushed.

“Are you crazy!” Sally was angry.

“I told you about the last time I travelled overseas. I’m not travelling as a man!” Sally sulked.

“Why would you. You are a woman. You are Miss Sally Macintosh, it says so right here on your birth certificate and your passport!” Valerie squealed and dropped them into Sally’s lap.

Sally just sat there stunned, staring at the birth certificate and passport. She thumbed through the documents and then dropped them on the coffee table. Then she squealed.

“We’re going to Bangkok! I love you Valerie Swindon!” Sally fell into her arms and kissed her.

“I take it you have similar documents?” Sally asked between kisses.

“Of course,” she replied.

“What a wonderful present,” Sally kissed and hugged Valerie again.

“Ok girl. Get yourself brushed up and dressed. Billy will be here in an hour to take us to the airport. Don’t pack; this suitcase is full of new clothes, we can play dress up at hotel in Bangkok,” Valerie beamed.

They flew first class and got through customs and immigration without a hitch and checked into the Bangkok Hilton. Valerie was only in the hotel for a day and then she checked into a private hospital and had her breast augmentation. The doctor made her stay for three days after the surgery and then let her go with instructions on how to care for her wounds and with enough drugs and dressings to fill a small pharmacy.

Valerie rejoined Sally at the Hilton for a celebration, but sex was off the cards; Valerie was still recovering.

“Too bad we’re checking out tomorrow. I’ve had a ball; I’ve even got a tan but you’ve spent most of the holidays in the hospital,” Sally stroked Valerie’s forehead, Valerie was lying on the lounge with her head in Sally’s lap.

“Well there is one other surprise. We’re not going home. We’re going to Phuket tomorrow to spend five days lazing on the beach and drinking cocktails with little umbrellas in them,” Valerie grinned.

“Shut the front door! You are so good to me Valerie,” Sally gushed.

“And to myself. It’s a great place to recover and I can at least wear a one piece and try out me new tits lying around the pool,” she laughed.

They took the short flight to Phuket the next day and caught a taxi to Patong. Valerie had booked them into a five star hotel. Valerie was so excited during the taxi ride she could hardly contain herself. At the hotel they were greeted with drinks and given an express check in; all they had to do was hand over their passports and proceed directly to their suite.

Valerie arranged to have the luggage delivered to their room, which was a beachside suite of course.

Just before they got to the room Valerie asked Sally to put on a blindfold.

“I’ve left the biggest surprise until last,” she held Sally’s hand and looked lovingly in her eyes.

“Ok Valerie, but I can’t imagine what else you could surprise me with,” she said and stood still while Valerie put the black velvet blindfold on her.

Valerie led Sally into the suite, Sally felt the temperature drop due to the air conditioning. Valerie got her to stop and Sally sensed she might be in the middle of the room. She was expecting perhaps a bouquet of flowers or something.

Valerie whipped off the blindfold and Sally saw flowers. Not a bouquet but at least twenty bouquets of beautiful tropical blooms. There was a bottle of champagne on ice on a low table. But the most striking objects were the two mannequins in the centre of the room.

The mannequins were wearing identical wedding dresses.

Sally was speechless. She turned to Valerie but was unable to vocalise.

“Will you marry me?” Valerie asked.

Sally still couldn’t talk. She was dumbfounded and mute.

Then she nodded vigorously and tears flew from her eyes.

She found her voice.

“Yes! Yes! Of course yes!” she whispered.

“Was that a yes?” a voice asked from behind a lace curtain billowing in the breeze.

“Yes!” shouted Valerie.

The lace curtains were ripped open and there was Emily dressed in a bridesmaid dress with a besuited Troy Bingham beside her. Billy and Raul were dressed in white suits with red carnations in the lapels. They all cheered and came into the room and popped the champagne.

Through the curtains was a small garden with a marquee set up and under the bower a Buddhist monk was sitting, meditating.

Sally looked both shocked and delighted.

“We have half an hour to do our hair, makeup and get into those dresses,” Valerie gushed.

There were two Thai beauticians waiting for them in the bedroom suite and they were done in twenty five minutes.

The monk married them under the bamboo marquee decorated with white and red orchids, and fuchsias, which matched their wedding bouquets. He intoned a Buddhist chant and then they read marriage wows prepared for them especially by Emily.

It was perfect.

They had a party in the garden after the ceremony and they ate, drank, and danced the night away.

Later that night alone in their huge bed sipping the last of the champagne, Valerie held up a scroll that the monk had given her.

“We are married in the eyes of god according to our orange-robed, bald-headed friend,” Valerie looked at the Thai script on the parchment.

“Of course this has no legal standing at all anywhere in the world. It’s just our declaration of love for each other for eternity,” Valerie smiled at Sally.

“It was beautiful Valerie. Except now you’ve really screwed up because as far as I’m concerned you are now mine for eternity,” Sally smirked.

“And you are mine,” Valerie kissed her bride tenderly.

To be continued.

Finishing School For Young Ladies Ch9

Author: 

  • Michele Nylons

Audience Rating: 

  • EXPLICIT CONTENT

Publication: 

  • Serial Chapter

Genre: 

  • Transformations

Character Age: 

  • Teenage or High School

TG Themes: 

  • Disguises / On the Run / In Hiding
  • Lesbian Romance
  • Tricked / Outsmarted

TG Elements: 

  • Bad Girls / Promiscuity
  • Girls' School / School Girl
  • Lesbians
  • Prostitution

Permission: 

  • Posted by author(s)

Finishing School For Young Ladies
By
Michele Nylons

Chapter Nine – Teacher Knows Best

“Well its back to the grind I suppose,” Valerie said sitting down to breakfast with Sally in their Soho flat on the last day of her holiday.

“I know you told me that you’re effectively still in hiding but I don’t know why you have to stay at fucking Saint Trinian’s,” Sally sounded a little exasperated.

“You know its Chelmsford Finishing School Sally, there is no need to be facetious. Are we having our first fight as a married couple?” Valerie smiled.

“I’ll tell you what I’ll do. I’ll go back to school and sort out my businesses there and then I’ll leave at the end of the year ok?” Valerie said in conciliatory tone.

“Wonderful darling,” Sally replied.

“And you stop prostituting yourself as of right now,” Valerie countered.

“But I want to contribute to our income,” Sally whined.

“I’ll find you something with dignity but I don’t want my wife hawking her arse anymore ok?” Valerie took Sally’s hand in hers and looked her in the eyes.

“Ok; I’ll be a housewife until you find me a job darling?” Sally grinned.

“Mmm…housewife eh? I kind of like that idea. So why don’t we duck in the bedroom and you can carry out your housewife duties on this,” Valerie smiled and pointed to the tent in her skirt.

“So long as I don’t have to wear a pinafore. Besides I’m still fascinated by your new tits so how can I say no,” Sally took Valerie’s hand and heaved her out of her chair.

Valerie was still unpacking when Emily came into her dorm with three other students. She looked sheepishly at Valerie.

“Let me guess…the Roman river thing?” Valerie said a little rankled.

“Valerie; since you’ve been gone the business has just got out of control. Alice, Mary and I can’t keep up. Both bedrooms are going non-stop and we’re having to blow and fuck guys in their cars because there are three of us and only two bedrooms,” Emily sounded exhausted.

“We need more girls and we need more rooms!”

“Or we need a better business model. I’ve been thinking about it and I might have a better plan. It’s complicated but lucrative if we can pull it off,” Valerie replied.

“Ok you three sit down while I ask you some questions and tell you the rules,” Valerie pointed at the three young hopefuls.

Valerie got Billy to cancel all the punters for that evening and called a business meeting at the cottage with Emily, Billy, and Raul. Billy went in his car to fetch Sally.

Valerie began to explain her new business plan when they were all settled.

“Ok. We can’t keep going on like this, our business model is unsustainable and the cottage isn’t big enough to run a brothel with the girls I now have on the books. I have three girls already working and three more signed up today and they tell there are more who want to.”

“So…we either totally reorganise and make a handsome profit from all those randy schoolboys and students and possibly other clientele, or we close it down and walk away. I’ll be up front and say there is some risk in my plan but I think we can pull it off.”

“First off we stop running a house of ill repute and start running a callgirl agency. We keep the cottage and use it as our base of operations. We can still use the converted bedrooms for the punters who don’t have their own digs or can’t afford a hotel room. Also, we change a few roles and functions around.”

“Billy; you and Raul drop off and pick up the girls and provide protection and muscle. Sally; you run the outcall bookings. Emily; you will be the girl’s madam, looking after the girls working from the cottage and generally making sure all of them stay healthy, keep clean, and meet their contractual obligations.”

“Contractual obligations?” Sally and Emily asked in chorus.

“Yep. I’m happy to run a callgirl business but we gotta look after these girls. This needs to be a short term money maker for them, not a career, so we get them to sign them to a contract. First off utmost secrecy, they can’t blab to anyone about what they are doing and who they work for. Next, they maintain their grades, we set a minimum grade average and if the girls drop below it they stop working. And finally they get three monthly medical checks. How does that sound?” Valerie finished her presentation.

“Sounds like it’s doable with a bit of patience and reorganisation,” Sally said.

“Raul and I would much rather provide muscle and a chauffeur service than running a knocking shop like we are now. But what about our cottage? Can we still keep it?” Billy asked.

“No but we’ll rent you a place nearby. Also I think we’ll get Raul on the school payroll as the porter and handyman. That way he will have a legitimate reason to hang around the school,” Valerie replied.

“I like the idea of becoming a madam and Troy will be happy to see me off the game; I think he’s not far from proposing,” Emily seemed very happy.

“There is one other problem we are going to have to deal with,” Valerie continued.

“Regardless of how careful we are, we aren’t going to be able to keep this a secret from the faculty. Most of teachers are old codgers and we can pull the wool over their eyes easy, but Lisa Meakins is as sharp as a whip so we are going to have to sort her out some way.”

Sally, Billy, and Raul had nothing to do with the Deputy Headmistress so they just shrugged their shoulders and left the problem with Valerie.

Later that evening Emily came into Valerie’s dorm. She had a duplicitous look on her face.

“Ok honey. What’s got you looking so shifty?” Valerie asked.

“I may have a way of getting Miss Meakins onside,” Emily grinned.

“I’m intrigued so go on,” Valerie was genuinely interested.

Emily had been at the school longer than Valerie so obviously she knew more about the faculty than Valerie did.

“Well I happen to know that Miss Meakins, is Miss and not Mrs Meakins for a good reason,” Emily smiled.

“Our Miss Meakins is a carpet muncher,” Emily snickered.

“A lesbian? Well that explains a lot but it’s the nineteen seventies sugar and being a lesbian isn’t a crime. I can try to blackmail her if she’s in the closet but I doubt it will work,” Valerie shook her head and offered cigarettes.

Emily lit up her ciggie but she was still grinning.

“Unless of course she was caught in flagrante delicto with a student,” Emily beamed.

“She’s not stupid enough to be fucking one of the students surely? That would just be too easy for us,” Valerie said.

“No but she’s got the hots for one,” Emily grinned.

Valerie grinned back at her.

“And would I be right in guessing that student is you?”

Emily blew smoke from her lips and nodded her head.

“Ok…so you’ve got Troy Bingham on the hook who’s undoubtedly giving you all the dick you can handle now that you too are almost engaged, you’ve tried a bit of tranny, are you up for a bit of lesbian action?” Valerie mused.

“Here is how I see this going down,” Valerie went on to describe the nucleus of her plan and she and Emily worked into the night to perfect it.

Two days later Emily confronted the Deputy Headmistress in her study and made the most outrageous of accusations.

“I have to show you Miss Meakins; you won’t believe it until you see it!” Emily declared.

“If it was anybody else but you Emily Milford I wouldn’t believe it. But because I trust you; I’ll come and have a look but if what you say is true then there is going to be some serious trouble,” Lisa said.

They were walking toward the gardener’s cottage set back in the small wood at the back of the school. Emily was leading the way and Lisa was admiring her pert behind clad in that tight pleated short skirt. She also admired Emily’s coltish legs clad in the sheer grey uniform stockings, the backseam running perfectly up the centre of her legs. Lisa was getting a little wet between the legs.

Emily slowed down her pace and when she was sure that Lisa was close behind her she deliberately stumbled.

She twisted and fell into Lisa’s arms; their bodies pressed together as Lisa held onto and steadied Emily. She felt Emily’s small breasts press against hers and inhaled her perfume. Their faces were only inches from each others and Lisa stared into Emily’s deep blue eyes.

“Sorry,” Emily apologised but kept her body pressed against Lisa’s.

Lisa made no real effort to let go of Emily, she was enjoying the feel of the young woman’s body pressed against her.

After a while the situation became awkward and Emily extricated herself from Lisa’s grasp. Emily was surprised at how titillating it felt pressing herself against Lisa. Lisa was mid forties and slim, but with an ample bosom, good legs and an attractive open face framed by brunette shoulder-length hair which she sometimes wore in a ponytail when alone in her study. Her makeup was a little heavy and she had a penchant for bright red lipstick.

Lisa’s breath was sweet and her perfume subtle; she was so close that Emily could smell the scent of her shampoo and conditioner.

Lisa continued the conversation to break the tension.

“Are you sure Billy Butler isn’t home? That guy scares the shit out of me,” Lisa asked.

“No, I’m certain he’s gone Miss Meakins otherwise I wouldn’t come here. Alice Corinda told me she was working here as a part time prostitute and of course I didn’t believe her one bit.”

“But I did have a quick look inside the cottage earlier today when I heard that Billy was away in Birmingham. The place looks suspicious to me, but I can’t be certain so that’s why I came to you.”

“You did the right thing Emily. Ok, here we are, let’s just make sure there’s no one home before we go inside,” Lisa said.

Of course Emily knew that Billy and Raul had taken the day off and were on a road trip but she made a show of checking that the cottage was empty.

“Look at that Miss Meakins; doesn’t that look like a professional bar, the way its stocked and the way the seating is arranged,” Emily said as they entered the lounge room.

“You’re drawing a long bow there Emily, knowing Billy, he entertains, what would he call them, geezers, on a regular basis,” Lisa observed.

“But how do you explain this then Miss Meakins,” Emily was at the door leading to one of the bedrooms which had been converted to a workroom for the prossies.

It had of course been embellished by Valerie and Emily so as to leave no doubt as to its purpose.

To start with there were three pairs of soiled knickers and a couple of pairs of laddered stockings on the floor which was also littered with several opened condom wrappers. The double bed was dishevelled, with the bedspread pulled back to reveal satin sheets. On the bedside table was a roll of twenty-four condoms, an near empty tube of KY jelly and a full tube next to it alongside a box of Kleenex. The bin had what appeared to be several used condoms in it.

The room reeked of cheap perfume and the lighting was deliberately subdued with a pinkish hue

Emily approached the bed and inspected it. She pushed the button on the side of the bed and a buzzer sounded in the lounge.

“What do you think? A panic button in case the customer plays up?” Emily feigned ignorance.

Lisa raised her eyebrows.

“And this?” She pressed the button on the bedside table and a red light came on above the door.

“Next please? I’m ready? Something like that I’ll bet,” Emily pretended to guess.

Lisa Meakins was flabbergasted. Actually shocked. She sat on the bed without giving a thought as to the purpose it had been recently used.

“I can’t believe any of our girls would do this…it’s…it’s unimaginable,” she sighed.

Emily sat down next to Lisa. Very close to her and her skirt rode up showing off the gauzy welts on her stockings.

“I can’t believe that Alice would do that. Let men do that to her for money, yuck!” she spat.

Lisa turned to face Emily, surprised at her vehemence.

“What do you find the most disturbing Emily, that she’s prostituting herself or that she’s having sex with men. Do you suspect she might not like men?” Lisa had inadvertently put her hand on Emily’s thigh and was absentmindedly stroking it.

‘Gotcha’ Emily thought to herself.

“Oh no Miss Meakins, Alice likes men, I just find them…what’s the word…rather irksome. They let that little head in their trousers make most of their decisions and they are so selfish,” Emily replied.

She reached out and touched Lisa’s arm.

“They are not as sensual and considerate as women,” Emily batted her eyelashes like a coquette.

“Don’t overplay it you dozy bint!” Valerie whispered to herself in the stuffy closet.

She looked through the viewfinder of the camera and adjusted the focus.

“Yes. I suppose you are right; women are generally more accommodating and sympathetic,” Lisa agreed.

Emily squeezed Lisa’s arm.

“That’s not what I meant Miss,” she looked Lisa directly in the eyes.

“It’s such a waste. Alice giving herself to men, even thought she’s being paid. Now if it was women that would be a different story all together,” she smiled conspiratorially.

“Ahem…I didn’t…err…I never thought you were that way inclined,” Lisa blushed.

“Can I confess something to you? It’s not illegal like what Alice is doing here with Billy, but it’s against the school’s code of conduct,” Emily brushed her fingers down Lisa’s arm and entangled their fingers together.

Lisa held Emily’s hand and squeezed it gently.

“I can’t grant you amnesty Emily; not if you have broken the rules,” she said, her voice choked.

“I trust you Lisa,” Emily said.

Lisa was about to protest Emily using her first name when Emily continued.

“I’ve been having a sexual relationship with Valerie Swindon ever since she arrived at the school.”

Lisa gasped.

Of course Lisa had no idea whatsoever that Valerie was a trans woman. She thought she was a young woman like the rest of her charges. A rather engaging young woman who’s breasts had budded rather magnificently recently.

“Well that’s certainly against our code of conduct,” Lisa gulped, she couldn’t help but imagine Valerie and Emily locked in embrace.

Images of the two young, attractive, lithe, women locked in a passionate clutch swam in her conscience. It was provocative enough sitting thigh to thigh beside this young vixen, holding her hand, breathing her perfume, trying not to look down at her firm stockinged thighs, in a room that reeked of sex. Her panties were becoming moist again.

“But it’s not against my own personal moral code though,” Lisa whispered.

“Really?” Emily took her other hand in hers and turned to Lisa.

They were now sitting knee to knee, Lisa examining Emily’s pretty face, getting lost in those big blue eyes. They both leaned forward instinctively; their lips only millimetres apart.

“Yes really,” Lisa’s lips barely opened as she responded.

Emily leaned forward and their lips touched. She squeezed Lisa’s hand and extended the tip of her tongue. Lisa opened her mouth slightly and crushed Emily’s lips and invited her to explore her mouth.

In the dark closet Valerie began to take a series of pictures.

Emily moved a hand to the back of Lisa’s head and pulled her face to hers. They kissed lovingly but excitedly. It was awkward sitting side by side on the bed and they stopped briefly to get rid of their blazers.

Emily lay down on the satin sheets and opened her arms and Lisa fell between them, straddling the young student as their lips met again and they resumed their fervid kisses. Emily’s pleated shirt had ridden up to the very top of her thighs. Lisa was wearing a navy blue business suit; the skirt was tight and but it was now bunched high on her legs. The women’s legs entangled and their nylons rustled as they rubbed against each other.

Lisa broke the kiss and she looked down at Emily and smiled. Emily’s lipstick was smeared and her hair fanned around her on the satin pillow. They began to unbutton each other’s blouses and wriggled out of them. Lisa grinned at Emily and unzipped her skirt and pulled it down her legs and threw it on the floor. While she was kneeling, Emily reciprocated and undid the zip on the side of Lisa’s skirt and dropped it beside her own.

Emily reclined on the bed in all her glory. Her pretty face with her smudged makeup, a result of their ardour, her pert breasts cupped in her white lace and satin brassiere, her flat belly and generous hips, white satin full-cut panties encased the treasures between her legs, and those long legs sheathed in sheer grey fully—fashioned stockings. Lisa gasped, beguiled by the gorgeous creature lying beneath her.

Emily smiled up at Lisa. Lisa’s lipstick and makeup was also smeared and her hair was in disarray. She was by no means fat but she was thicker than Emily, as would be expected of a woman in her forties. Her breasts were full and rather ponderous, the C-cups of her black lace bra just managed to contain the creamy orbs and her nipples were erect. Her skin was smooth and milky white, with a little bulge of excess flesh above the waistband of her control-top pantyhose. She wore her black lace panties over the gusset of her pantyhose for aesthetics. Her thighs were thick but well-formed and her legs shapely, her hosiery glittered in the dull light of the bedroom.

Lisa fell on Emily and kissed her; her hands found Emily’s breasts and their legs entwined as they arched their backs and thrust against each other.

Hiding in the closet Valerie was erect in her knickers. She was here to take pictures of the encounter for later use but she was extremely aroused watching the two pretty women rut and caress each other. She cleared her head and looked through the viewfinder again. Sally was definitely going to get a good humping when she got home Valerie smiled to herself.

Lisa lowered her face to Emily’s breasts and flicked her tongue across her nipples. Emily gasped. Lisa nipped on Emily’s nipples, gently biting them and bringing them to full tumescence.

“Oh yes!” Emily pushed Lisa’s face down to her bosom and writhed underneath her as Lisa slathered and nibbled on her sensitive teats.

Emily tried to get her hands between their bodies so she could caress Lisa’s breasts but Lisa shook her head.

“No. Let me pleasure you honey,” Lisa gasped and then lowered her face back to Emily’s bosom.

Emily moaned. She was getting wet and wanted release.

She eased Lisa’s face from her breasts so they could kiss. Her hand snaked down Lisa’s belly and slid inside the gusset of her pantyhose and found her sex hot and moist. She parted the outer lips and slid a finger inside Lisa’s labia and found her clitoris peeking from its hood. She gently manipulated the firm bud and Lisa squealed.

“Oh god!”

Lisa’s hand investigated the inside of Emily’s panties. She stroked Emily’s mound and found that she too was sopping wet and her folds engorged. She gently circled the pad of her index finger on her erect nubbin and slid her tongue deeper into Emily’s mouth to smother her gasps.

She grinned against Emily’s lips.

“So did you and Valerie ever try this?” Lisa smiled.

She ripped off Emily’s knickers and shucked out of her own. She pushed a red-painted fingernail into the crotch of her tights and enlarged the hole to expose her sex.

“You’re going to love this,” Lisa gushed.

She opened Emily’s legs and she scooted to the bottom of the bed and lay on her side. Emily pushed one leg under Lisa and placed the other across her belly.

Then she pushed up hard.

The two cunts squished together and Lisa began a slow grind.

“Oh my god that is so sensuous!” Emily moaned.

The two women squirmed and wriggled together, working hard to get pressure on their clitorises. Their vaginas were sopping wet, making liquid squishing sounds as they mashed together. They groaned and shuddered at the intensity of the pleasure that radiated from their sopping clefts as they squeezed and pressed their sexes together.

Emily orgasmed first and shrieked like a banshee as the most intense orgasm she had ever experienced washed over her. Emily’s yelps of pleasure invoked Lisa’s climax and she too began to wail as extreme pleasure coursed through her body.

Valerie smiled and stroked her hard cock through her panties as she snapped away taking multiple frames. She wished she'd bought a tape recorder as well as a camera.

The two lingerie-clad women clung to each other as their orgasms subsided and Lisa scooted up the bed so that she was lying face to face with Emily. They held each other and kissed passionately, still excited and aroused.

Emily assumed the dominant position and pushed Lisa down on the bed. She kissed Lisa’s breasts but her lips and tongue continued their journey down Lisa’s body until she found her sex. Lisa’s vagina was a sopping maw, her labia distended and swollen, her scent pungent. Emily lowered her face and began to lick the savoury secretions, nibbling gently on the lips of Lisa’s cunt, until at Lisa’s insistence, she found her achingly tender clitoris, which she gently lapped.

“Oh my; not again!” Lisa screamed.

Emily lifted a leg over Lisa’s body so that her cunt was directly over Lisa’s face and lowered herself, nestling her own sopping minge against Lisa’s mouth. Lisa obligingly licked at Emily’s cunt, finding her clitty and working it with the tip of her tongue.

They lapped at each other and soon both women were orgasming again, pushing their crotches into each other’s faces as they sucked on their delicate protuberances and swallowed each other’s juices.

When they were finally sated they cuddled together almost naked, their knickers and bras discarded, legs intertwined, hosiery laddered and holed and heels lost somewhere in the bedsheets.

They kissed and caressed and stroked each other tenderly.

“You know what we just did was totally wrong,” Lisa finally spoke.

“There was nothing wrong about it. It was beautiful,” Emily smiled at her teacher.

“Yeah but you’re half my age and my pupil,” Lisa sighed.

“But I’m not a child and I was willing. Fuck! I started it!” she grinned.

“Yes you did you naughty girl,” Lisa playfully spanked Emily’s bottom.

“Ok. Reality bites! I’m going to have to confront Alice Corinda and Billy Butler. I’ll have to expel Alice and sack Billy. I won’t call the police or publicly state why; I want the school to keep its reputation,” Lisa said.

“And…What about us?” Emily looked a little coy.

“I need to think about that. What we have is lovely but it’s dangerous. I’m thinking that if we want a relationship, and I’m not sure you do, it will have to be kept off school grounds,” Lisa said clinically.

“Well teacher knows best,” Emily grinned and received another spanking for her impudence.

“As for now. Given our current state of dishevelment, it’s probably best if we don’t walk back to the school together,” Lisa said.

“Of course Emily,” agreed.

They disentangled themselves. Lisa’s pantyhose were ruined so she stripped them off and threw them on the floor with the other discarded lingerie, Emily’s stockings were laddered but still wearable so she straightened her seams, pulled on her knickers and bra and stepped into her skirt and buttoned her blouse.

Lisa hated bare legs and she rummaged in her purse and found the pair of tights that she kept for backup in case of a ladder. The school’s old wooden furniture took its toll on the girl’s and teacher’s hosiery. She lay back on the bed and pulled on the pantyhose; she preferred stockings but pantyhose were more practical for work. She finished dressing.

“Hey check this out!” Emily called out.

She was holding up the cosmetics case that the prossies used to fix their makeup between punters. The two stood side by side at the dresser mirror fixing their makeup and brushing their hair.

They checked each other out. If anyone looked closely they would see the wrinkles and creases in their skirts, blouses and blazers but they looked presentable.

“See you soon,” Lisa leaned into Emily and kissed her softly on the lips.

“I hope so,” Emily smiled.

Emily watched the Deputy Headmistress trudge up the path through the wood while she poured two large scotches. When Lisa was engulfed by the thicket, Emily tapped on the door to the closet and opened it.

Valerie was removing the camera from the tripod.

“You played your role particularly well,” she smirked, taking the proffered scotch whisky.

“Well it’s not the most revolting task I’ve had to undertake. In fact it was quite pleasant,” Emily grinned.

“And I have some wonderful pictures to prove it,” Valerie smiled in return.

“And I’ll take these too,” she bent over and picked up Lisa’s discarded pantyhose.

They clinked their glasses together and sipped the warm liquor.

“To a job well done,” Valerie toasted, looking very satisfied.

To be continued.

Finishing School For Young Ladies Ch10

Author: 

  • Michele Nylons

Audience Rating: 

  • EXPLICIT CONTENT

Publication: 

  • Serial Chapter

Genre: 

  • Transgender

Character Age: 

  • Teenage or High School

TG Themes: 

  • Blackmail
  • Disguises / On the Run / In Hiding
  • Lesbian Fantasy

TG Elements: 

  • Bad Girls / Promiscuity
  • Girls' School / School Girl
  • Lesbians
  • Prostitution

Permission: 

  • Posted by author(s)

Finishing School For Young Ladies
By
Michele Nylons

Chapter Ten – An Offer You Can’t Refuse

Valerie strode confidently down the hall towards the Deputy Headmistress’ study. Sitting outside the study waiting for an audience were Billy Butler and Alice Corinda.

Valerie winked at Billy and opened the door without knocking and strode into Lisa Meakins’ office.

“How dare you come in here unannounced Miss Swindon! Get out and stay out until you have an appointment!” Lisa was livid.

Valerie just smiled and sat down uninvited.

Lisa looked like she was about to explode when Valerie reached into her handbag and pulled out a pair of ripped pantyhose and dropped them on Lisa’s desk.

They could be any old pair of discarded tights but as soon as Lisa saw them she recognised them as her own Pretty Polly’s with the ripped out crotch.

Lisa paled.

“I think you might want to keep your voice down Miss Meakins,” Valerie said in hushed tone.

She took an envelope out of her purse and shook the contents out on Lisa’s desk. The two photographs were in black and white but their resolution was almost perfect. One photo depicted Lisa Meakins and Emily Milford engaged in mutual fellatio and the other in a position known in Lisa’s circles as scissor-sisters.

Lisa visibly collapsed in her chair; she was blanched and her breathing was erratic. Valerie arose and poured her a glass of water from the pitcher on a table near the window.

After a beat, Lisa recovered enough to talk.

“How much?” she swallowed.

“Oh you’ve got me completely wrong Miss Meakins. This is blackmail but not for money,” Valerie grinned wickedly.

“Let me explain something to you. It’s going to take a little while but I’m sure you can spare me the time.”

“What you saw at the cottage was staged a little but non the less real. A brothel is being run out of there; in fact there are six students working for me as prostitutes.”

Lisa was astonished. Dumbfounded that something like this could be going on right under her nose.

Valerie pointed to Emily in one of the pictures.

“Up until recently she was my biggest earner but now I’ve promoted her to management…anyway I’m getting ahead of myself.”

Valerie told Lisa everything. From the day she had been orphaned, her transition, her relationship with Sally, her abuse at the hands of Harry Cartwright and Harry’s abuse of the girls. She went on to explain how she had taken over Harry’s business flogging contraband to the girls and how her idea of selling the services of those girls willing to do so, had developed into a small but lucrative prostitution ring.

To say Lisa was astonished was an understatement.

“I don’t believe it,” Lisa whimpered.

“You are now one of a handful of people who know I’m transsexual. Besides Sally and Emily there aren’t many here in the UK. You obviously noticed my sudden budding breasts when I came back from my holiday in Thailand. Anyway that’s not important,” Valerie continued.

“About my money. I’ve been spending quite a bit but turning a good profit too and I have close to the three hundred thousand pounds I started with,” Valerie smiled.

Lisa was beginning to recover her wits and she had more than a few questions to ask but some were more imperative than others.

“Why are you telling me all this? There are a couple of courses of action I suppose. You can blackmail me with those pictures and Emily’s testimony should you wish to ruin me forever. I can go to the authorities; but then I’m guessing we all go to jail. Or I suppose the worst outcome for me is that thug outside, Billy Butler, takes me for a ride from which I don’t return; but if you were going to do that you would have done so,” Lisa sighed dispassionately.

“Or…I can make you an offer you can’t refuse, as was said in the movie ‘The Godfather’,” Valerie replied.

“I have six girls here at the school working for me. They need the money but they want to stay in school and make something of themselves. Neither they nor I want them to be prostitutes for the rest of their lives…”

Valerie went on to explain her edict that the girls sign a contract swearing them to secrecy, requiring them to keep up their academic grades, and that they have regular health checkups.

“So what Valerie? You still plan to turn my school into a glorified knocking shop,” Lisa snipped.

“No that’s not my business model. Certain young ladies would be employed in a refined escort agency, a long way from being a street walker or mattress bouncing strumpet,” Valerie replied.

“And we would put a percentage of the money the ladies make back into the school. To start with I will give you a hundred thousand pounds to renovate the place. We hire proper maintenance and support staff and we return Chelmsford Finishing School for Young Ladies back to its former glory,” Valerie grinned.

“You’re insane,” Lisa spat.

“We run the escort agency off the campus, out of the gardener's cottage. The girls get taken to and from their appointments by Barry or his friend Raul who are also charged with their protection. My partner Sally will take the bookings and Emily will make sure the girls are looked after,” Valerie continued.

“And what do I do?” Lisa asked.

“Simple. You run the school. As Deputy Headmistress you run the school’s finances so you can ensure the money we make goes to the benefit of the school, and that we get good staff and good teachers,” Valerie explained.

“We also use some of the funds to help our graduating ladies find suitable employment. It can all be for the good of the school.”

“And if I don’t go along?” Lisa said.

Valerie pushed the nylons, the pictures, and a strip of negatives across the table towards Lisa.

“That’s everything I have on you. Emily won’t say anything about what happened in the cottage; from what I saw she is as implicit as you and she certainly wasn’t coerced. The ball is in your court as they say. You can fire Billy, expel me, Emily and the other girls. I doubt you would call the police. Then you can watch Chelmsford Finishing School for Girls go broke and slowly rot like the rest of the Finishing Schools until there is nothing left.”

“The girls who are already working and those who want to work as escorts will likely end up on the streets except for those whose mommies and daddies have a lot of cash.”

“I’ll leave you to think about it shall I?” Valerie stood, smoothed her skirt and left the Deputy Headmistress’ study.

She nodded at Billy and Alice, indicating they should follow her.

“Well I made her an offer; we will just have to see what she does with it,” Valerie said later that evening in her dorm to Emily.

Lisa watched the door to Valerie’s dorm and waited for Emily to leave before she entered.

The room was dark, lit only by a table lamp, its shade covered by a red silk scarf. Lisa entered and closed and locked the door behind her. She had important things to say and she wanted complete privacy.

Valerie was still dressed in her school uniform sans blazer and tie; she lay on her bed with her skirt high on her thighs displaying those lovely long legs encased in sheer hose with the dark gauzy welts clipped to her garters. She had a ladder in one of her stockings; one shoe balanced delicately from her toes, swinging lazily back and forth. She had piled pillows behind her head and her pretty face, with those ruby-red lips and vivid green eyes, was framed by the capacious tangle of her hair. Her pert firm breasts pushed against her blouse.

She was sipping a gin and tonic and had an ashtray on the bed beside her with the ever present packet of Benson and Hedges.

“You didn’t knock,” Valerie smiled sweetly at Lisa.

“Faculty do not need to knock at student’s dorms Miss Swindon and you know that,” Lisa smiled back just as sweet.

“I suppose its Mrs Swindon or Mrs Macintosh. Sally and I never really chose a married surname; at least in Thailand anyway,” Valerie was feeling a little flirtatious now that it was decision time for Lisa.

“You’re married? Really?” Lisa was distracted by the segue

“Sally and I had a marriage ceremony in Phuket; it’s not recognised anywhere in the world but we made a commitment to one and other,” Valerie explained.

“But that’s not why you’re here is it?” Valerie bought the conversation back to point.

“Please sit,” Valerie smiled and patted the bed beside her.

Lisa smiled glibly and pulled up a chair instead. She pointed to Valerie’s cigarettes and Valerie shrugged her shoulders. Lisa took one and lit it and then poured herself a drink without asking. She sat down on the chair, smoothing her skirt under her legs.

Lisa had changed after school and wore an above-the-knee plain black A-line skirt and mauve silk blouse; she wore flesh-toned pantyhose, black heels and accessorised with matching silver drops, necklace, bracelet and rings. Valerie was amused to see that she also wore an ankle chain.

As usual her makeup was heavy and she wore her favourite bright red lipstick. Her shoulder-length brunette hair was worn in a ponytail. She looked younger than a woman in her forties and obviously took care of her body and her appearance.

“That’s quite a story you told me this afternoon. I would never have guessed you were transsexual despite your rather exotic smoky voice. And you’re running a brothel out of my school and have a sideline selling contraband to the girls,” Lisa drew on her cigarette.

“Nicely summarised,” Valerie smiled at her.

“Did you mean what you said about a percentage of the profits going to the school?” Lisa said earnestly.

“Absolutely. I want the girls to succeed, I want the school to succeed, and I want everyone to be gainfully and profitably employed,” Valerie continued to smile.

“And you want your business to flourish of course?” Lisa smiled glibly.

“Of course,” Valerie’s smile didn’t waver.

“And I run the school while you run the collateral businesses?” now Lisa was smiling.

Lisa reached out and began to trace the runner in Valerie’s stocking with a manicured bright-red fingernail.

“You have a ladder,” Lisa whispered, her finger tracked the fissure in the diaphanous nylon.

“The old wooden furniture here is notorious for snagging stockings, I sell them from my little shop too,” Valerie gasped as Lisa continued to delineate the imperfection in her stocking.

Lisa’s finger traced the ladder up to the dark welt at the top of Valerie’s stocking. She lazily circled the silky textured fabric and flicked at the silver garter tab.

“Don’t you find it rather archaic that the school insists that the students wear stockings?” Lisa’s began to stroke Valerie’s gossamer-sheathed thigh.

Valerie trembled at Lisa’s touch.

“I said the same thing to Pauline Delaney at Mrs Delaney’s Couturier and Haberdasher and her reply was quite terse.”

“ She said it’s so simple to pull on a pair of sheer tights or pantyhose as our American cousins call them, but the ritual of snapping welts to garters, smoothing out wrinkles and straightening seams is character building. It requires patience and attention to detail. And that is why stockings are still the mandated hosiery for Chelmsford Finishing School for Young Ladies.”

“I remember it like it was yesterday,” Valerie smiled.

“But pantyhose can be just as sexy don’t you think?” Lisa lifted a toned, translucent-sheathed leg and put it on the bed.

Valerie couldn’t resist and reached out to stroke it delicately.

It was Lisa’s turn to shudder.

“Mmm. They are very soft and sheer. Are they sheer-to-the-waist?” Valerie's hand disappeared under Lisa’s skirt to explore the top of her thighs.

“And satin knickers over your tights…I like that too,” Valerie skimmed her fingers across the front of Lisa’s panties.

“Yes and you too,” Lisa’s fingers delved under Valerie’s pleated skirt and found her white satin and lace panties.

The two coquettes grazed fingers across panties and gazed at each other licentiously.

“So how married are you?” Lisa said; her voice thick with lust.

“Like I said. It’s not legally binding,” Valerie’s voice was equally wanton.

Valerie scooted over on the bed to make room for Lisa, tossing the cigarettes and ashtray on the nightstand out of the way.

Lisa climbed on the bed and lay beside Valerie; they stared at each other and then Lisa reached out gently stroked Valerie’s face.

“You are quite the manipulative bitch,” she whispered.

“Is that an insult or a compliment,” Valerie reached for Lisa and placed her hand on her waist.

“Take it any way you want,” Lisa sighed and leaned into Valerie and kissed her.

They touched tongues as their lips pressed together and then pressed their bodies together.

“I thought you were lesbian,” Valerie whispered in Lisa’s ear.

“I am and you’re a gorgeous young woman. A young woman with a cock and I wanna see what that’s like,” Lisa panted her reply.

“So basically you’re just using me?” Valerie sniggered.

“Oh shut and fuck me you blackmailing bitch!” Lisa gasped and closed her mouth back on Valerie’s.

The women kissed and entwined their legs, rubbing their pelvis’ together whilst removing each other’s blouses which were quickly cast aside. Their brassieres followed. Lisa had full breasts whilst Valerie’s were small and pert, the small scars underneath almost invisible now. They pressed their breasts together as their ardour grew and they kissed frenziedly.

They caressed each other’s bosoms, Valerie was impressed with the heft of Lisa’s pendulous tits and tweaked her swollen nubbins whilst Lisa was able to fit all of Valerie’s small breast into her mouth and lap at her teat with the tip of her tongue. Valerie lowered her face to Lisa’s chest and suckled on her fat, hard nipples. They both enjoyed the breast-play whilst grinding their groins together and rubbing their legs against each others. The room was filled with the sound of whimpers, gasps, slurps and the rustle on nylon on nylon.

They reluctantly stopped suckling each other’s breasts as the need to kiss each other as an expression of intimacy became the imperative; their breasts squeezed together as they hugged and caressed each other.

Hands went exploring under skirts, lazily sliding up nylon-sheathed thighs, caressing and groping as passions peaked. Their attempts to slip out of their skirts were thwarted by their lust and impatience and they simply rucked and hiked them up out of the way so that their skirts swaddled their waists.

They now had unfettered access to each other’s genitalia, other than the flimsy layers of panty and pantyhose. Lisa slid her fingers along the soft skin above Valerie’s stocking-tops and slipped them inside the leg of her knickers. She was not sure what exactly she would find but soon discovered Valerie’s penis taped between her legs. She ripped away the surgical tape and Valerie gasped in Lisa’s mouth as her semi-erect penis sprang free and her testes lowered into her scrotum. Lisa smiled and Valerie registered that smile while they kissed.

Valerie reciprocated and her fingers slithered inside the leg of Lisa’s panties and found that Lisa was wet and had saturated the crotch of her pantyhose. Valerie smiled too, and used her finger to trace the outer folds of Lisa’s sex. Lisa gasped and opened her legs, encouraging Valerie to explore further; she gripped Valerie’s penis and began to improve her erection.

Valerie responded and dug her fingernail into the translucent fabric of Lisa’s hose until it parted. She poked her finger in the hole and ripped a hole in the crotch. Without hesitating she pushed her fingers into Lisa’s sopping maw and explored the slick folds and contours of her vagina, sliding a finger inside and using her thumb to press on her clitoris.

Lisa arched her back and gasped. She gripped Valerie’s now fully tumescent erection and squeezed and then released it. She languidly ran her fingers up and down its length gliding the pad of her forefinger on the fraenulum, using the copious amount of pre-seminal fluid leaking from Valerie’s cock to lubricate her shaft.

Their kissing became frantic and manic as they pawed at each other. Their bodies were pressed close together with their hands enthusiastically manipulating each other, their sheer-nylon-encased legs entwined and entangled.

Valerie rolled over so that she was straddling Lisa, her cock was pressed into Lisa’s crotch; rubbing on her soaked minge through her satin panties. Lisa’s raised her hands and took Valerie by the shoulders.

“Put it in me darling. Oh my god put it in me,” Lisa groaned.

Valerie eased aside the gusset of Lisa’s panties and pressed forward, her glans parted Lisa’s labia and pressed against her hooded clitoris.

Lisa rose on her haunches pushing up; she wanted that hard cock inside her. She was so turned on having the beautiful young woman with the hard cock lying on top of her, about to penetrate her. It was a lesbian dream true.

Valerie smiled down at Lisa, she enjoyed teasing Lisa, rubbing the tip of penis on Lisa’s engorged clitoris but she too needed release.

She pressed her haunches forward and her cock slid inside Lisa’s sopping, buttery vagina. She pushed it in all the way so that her pubic bone pressed on Lisa’s pubis, stimulating her clitoris while her shaft inched slowly back and forth inside Lisa’s tight sheath.

They kissed, their moans stifled by crushed lips and slavering tongues. Lisa had not felt a penis inside her for over twenty years; she had used vibrators and dildos but they felt nothing like Valerie’s throbbing cock. She lifted her legs and locked them around Valerie's waist so she could raise herself and grind her mound against Valerie and encourage her to thrust her cock in out of her vagina. She wanted to be fucked.

“Fuck me you bitch! Fuck me!” Lisa gasped.

Valerie capitulated and slowly eased her phallus in and our of Lisa’s tight juicy passage; Lisa’s nylon-sheathed legs scoured her flanks encouraging her, her highheels raked Valerie’s side. Valerie responded and fucked Lisa with long hard strokes, extracting her glans to Lisa’s entrance and then thrusting inside her, smashing their pubis together.

The two wanton wenches rutted and fucked each other, encouraging and goading each other with their mouths, their legs, their bodies and their sex. Lisa’s vagina rippled with exquisite sensations of pleasure as Valerie fucked her, her clitoris was palpitating with sensual delight. Her orgasm was building like a volcano about to explode.

Valerie sensed Lisa’s urgency as she bucked and wriggled beneath her, clinging to her like a boat in a storm. She could also feel her own orgasm building, the feel of Lisa’s silky legs on her skin, her own panties caressing her scrotum intensified the sensations she felt from her throbbing penis as it pounded away at Lisa’s slick tight hole.

The two stunning ladies clung to each other and fucked, oblivious to the world around them. Lisa came first, screaming obscenities as she scratched and pawed at Valerie, forcing her mound against Valerie’s pubis. Her cunt quivered and rippled; incredible feelings of pleasure surged through her vagina as Valerie’s cock pulsed and swelled, spewing forth a torrent of hot semen deep inside her.

Valerie clung to Lisa, driving her down into the bed as she swivelled her hips and ground herself against Lisa, emptying herself. She gasped and groaned with the intensity of her orgasm as her cock convulsed and sent shockwaves of pleasure through her body.

The two sweaty, lust-ravaged, love-dolls lay gratified and exhausted in each other’s arms. Valerie tried to extricate herself from on top of Lisa but Lisa hooked her legs over Valerie’s thighs and put her arms around her neck and squeezed her.

“Where do you think you’re going?” she smiled up at Valerie, her bright-red lipstick smeared across her mouth and her hair dank with perspiration.

“Nowhere I guess,” Valerie smiled down at Lisa.

Valerie’s makeup was also a mess and her hair hung lank and tangled.

“So this Sally woman; she’s cool with us…you know…?” Lisa looked questioningly up at Valerie.

“Well we never really discussed fidelity, I think we both assumed that ours would be an open relationship but we remain committed to each other,” Valerie replied.

“Well you’re lying on top of me with your cock inside me so I guess you’ve made your point,” Lisa contracted her vaginal muscles and squeezed Valerie’s cock.

“Speaking of which…now that you have seduced me, does that mean we have a deal regarding my proposition for the school?” Valerie asked sarcastically.

“Oh come on! I seduced you? You seduced me!” Lisa grinned up at Valerie and kissed her quickly on the mouth.

“Would it be fair to say that we seduced each other?” Valerie smirked.

Lisa tightened her arms around Valerie’s neck and pulled her face down so they could kiss. After a while Lisa constricted her vagina, feeling Valerie’s penis become fully erect inside her.

“Wanna do it again,” Lisa teased, rubbing her legs sensuously on Valerie’s.

Valerie lowered her face to Lisa’s and slid her tongue into Lisa’s mouth as she slowly began to fuck her.

To be continued…

Finishing School For Young Ladies Ch11

Author: 

  • Michele Nylons

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • EXPLICIT CONTENT

Publication: 

  • Final Chapter

Genre: 

  • Transgender

Character Age: 

  • College / Twenties

TG Themes: 

  • Disguises / On the Run / In Hiding
  • School or College Life
  • Tricked / Outsmarted

TG Elements: 

  • Bad Girls / Promiscuity
  • Girls' School / School Girl
  • Identity Theft
  • Prostitution

Permission: 

  • Posted by author(s)

Finishing School For Young Ladies
By
Michele Nylons

Chapter Eleven – Business As Usual

The businessman sat in his cheap London hotel room sipping a Johnny Walker. He twiddled what appeared to be a business card between his fingers. The small black high-gloss card had the silhouette of a stylised schoolgirl with her skirt flung high showing off her stockings embossed on it in silver. Under the logo was printed the words ‘Saint Trinian’s Escorts’ followed by a phone number.

The man nervously reached for the phone, requested an outside line, and then dialled the number on the card.

The phone was answered by Sally Mackintosh who was sitting at her orderly desk in her makeshift office located in the gardener’s cottage on the grounds of Chelmsford Finishing School for Ladies. Sally conversed pleasantly with the gentleman and then hung up.

“Wendy you’re up! Raul; you’re driving!” Sally called around the cigarette dangling from her mouth.

Raul came into the office and picked up a slip with the address of the hotel written on it and walked back through the lounge room to go to the car outside. Wendy Hodgkins, halfway through a two year enrolment at the school and second in her class in academic subjects, rose from the couch, stubbed out her cigarette, and followed Raul out to the car.

Raul pulled up outside the hotel and watched Wendy all the way to the door. A few minutes later he saw her wave briefly to him from a window on the third floor. All was well and he picked up the racing form and scanned it.

In the hotel Wendy slid out of the tight blue satin-sheath dress she had been wearing and stood before the man who sat naked on the bed. Her black satin and lace, waist-cinching bustier barely contained her voluptuous figure and huge breasts, her ensemble was complete with sheer black stockings, wispy nylon panties and black highheels.

The man was very excited and summoned Wendy to join him on the bed. She knelt before him and opened a condom wrapper with her teeth and expertly put the condom on the man’s stubby erection with her mouth. It almost made him come.

She lay down on the bed and opened her legs and the skinny balding business man scooted between them, still wearing his black socks.

Wendy pulled aside the gusset of her panties and the man stabbed at her with his small fat cock until he found her entrance. When he did he almost fainted with lust. Wendy smiled and held him against her, letting him slaver at her face with sloppy kisses while his skinny bum bounced up and down.

He came quickly, howling like a banshee and Wendy smiled to herself, wondering what the occupants of the other rooms must think.

She let him finish and then extricated herself from underneath him and took off the rubber johnny, wiped him clean, and dropped the johnny in the toilet and flushed. While she was in the bathroom she quickly fixed her makeup and then squeezed back into her tight dress. She lit a cigarette while the man counted out the money on the bed. He cheekily shoved a fiver, a tip for her in addition to her fee, into her stocking top.

Wendy kissed him again and let him have a quick feel before she politely disengaged from the punter and made her way to the lift.

She was back in the car with Raul less than fifteen minutes after they’d arrived at the hotel.

“That was quick,” Raul said offering her a cigarette over the seat.

“Yeah, he’s a sweetie but he never lasts long. His missus stopped giving him sex years ago,” Wendy replied as she lit the cigarette.

She took the fiver out of her stocking and added it to the two tenners the businessman had given her in payment and handed the money to Raul.

The girls shared everything. They were well paid and there was no need to keep tips or skim from the punters.

Wendy and Raul were back at ‘The Cottage’, as it had come to be known, barely half an hour after they had left. The money Wendy had earned was locked in the safe after being carefully entered into the ledger by Sally.

Valerie’s business model was working. It operated under the name ‘Saint Trinian’s Escorts’ and was supplying call girls on a regular basis to an exclusive and trusted clientele. It provided everything from elegant social escorts, overnight stays, or hotel quickies such as the services just provided by Wendy. They still had the two ‘playrooms’ operating in the cottage, mainly for college lads who couldn’t afford a hotel room in addition to the girl’s service fee.

It was not that long after the fateful evening when Lisa had come to Valerie’s dorm and they had made love and agreed to Valerie’s proposal, that Valerie once again found herself standing out the front of the dodgy looking dilapidated building in the back streets of Moulsham.

The alley was dark and still strewn with abandoned shopping trolleys, junk food wrappers, empty beer cans and bottles, cigarette butts, and condom wrappers.

Valerie turned down the alley and her heels click-clacked on the dirty cobblestones.

“Jesus! Doesn’t any cunt clean this place up?” she hissed, kicking an empty beer can out of her way.

She passed the doorway where the old prossie used to ply her wares. She’d either moved on or her daughter had taken over the family business. Her young blonde protégé was not quite as beat up as her predecessor, wearing a similar stained leopard skin mini dress with her tits nearly falling out of it. Her flesh-toned hose were laddered but at least her black high heels were in good condition and her makeup was half decent.

She was pressed against the doorway while a dodgy-looking punter held up the back of her dress and fucked her from behind. He grinned at Valerie as she passed and requested she join them. Valerie raised a finger and kept walking.

She knocked on the door that was still caked with fading and peeling blue paint, experiencing feelings of déjà vu. Steve opened the door, a smile lit up his face.

“What are you grinning at? You look like the cat that ate the canary,” Valerie stepped inside and was amazed at the transformation that had taken place since the last time she had been here.

The warehouse had been repainted and fluorescent lighting had been installed and the old tatty furniture replaced by new furniture and fittings. All the equipment looked shiny and new.

“Fuck me! This place has changed. Did you win the lottery or something?” Valerie looked around at the professional looking studio.

“Well remember that girl I told you about? Candace…err Candi Pops?” John Benstead grinned.

Valerie nodded vaguely

“Well she’s my missus now and she earns a fucking bomb. And I don’t do too bad myself so I upgraded the joint. I left the façade and the alley looking like a shithole and that throws off the Old Bill. It’s sort of camouflage” John looked pleased with himself.

“Anyway, Billy The Bottle passed on your instructions and here it is. One Batchelor Of Education in the name of Valerie Swindon,” he flourished the document as he made his way over to his new executive desk and big leather swivel chair.

As Valerie sat down opposite she noticed that the ratty chest of drawers, strewn paperwork and the stamps, ink pads, pens, glue, scissors and other detritus had disappeared. The place looked eminently professional.

John still looked good for a man in his forties. He continued to wear his blonde hair long and styled but his tan and muscled physique was now shown off by wearing an expensive open-neck body-shirt and tight slacks instead of the ratty t-shirt and jeans he used to favour. The obligatory cigarette hung out the corner of his mouth.

“Still cocksure of yourself, aren’t you?” Valerie smoothed her skirt and noticed John gaze at her legs, today clad in sheer tan pantyhose.

“Darling, the last time you were here, the final thing you said to me was: ‘You’re not as good as you think you are! You better get your shit together if you’re hoping to get together with this Pops woman.’ I took your advice,” he smiled at her, not even attempting to disguise the fact that he was ogling her.

“And does Miss Pops know that you still try to get into the knickers of every lady that comes to you for business,” Valerie said in a clipped tone.

John got up and walked around the desk and stood before her. He pulled Valerie out of her chair and held her close.

“Not every lady. Just gorgeous creatures like yourself,” he sighed and tried to kiss her.

Valerie turned her head away and began to struggle but John held her tight as she wriggled in his grasp. Her movements were exciting him and Valerie could feel his hard cock pressing against her through his slacks and her skirt. She was wearing a business suit and a satin blouse and John was trying very hard to get his hands inside said blouse.

“Stop it!” Valerie hissed and tried to stamp on his toes with her highheels.

John just grinned. His hand had found its way into her blouse and inside her brassiere. He cupped her small firm breast and tweaked her nipple and it hardened to his touch. His other hand was under her skirt fondling her buttocks; squeezing and stroking them.

“Stop it!” Valerie gasped into his mouth as it closed on hers.

She made a perfunctory attempt to stop him one final time and then surrendered and kissed him back and put her arms around him.

They kissed and rubbed against each other for a while than Valerie gently pushed him away.

“Ok loverboy, I’m in a rush so lets get this over with…and I want a hundred off the deal,” Valerie smirked.

“Oh come on Valerie you know I can’t…oh my fucking god!” John gasped.

Valerie had dropped to her knees, freed John’s penis, and taken it into her mouth.

She suckled on his hard cock, bringing it to full tumescence and then rose to her feet, bent over the desk and pulled her knickers and pantyhose down around her knees. She wiggled her buttocks seductively and offered herself to John who moved in behind her, lowering his trousers.

John used a finger to check to see if Valerie was lubricated; being in a full-time relationship with a transsexual himself he knew the importance of lubrication.

John found Valerie lubricated and judging by the jiggle she gave when he fingered her, he knew she was ready. He pressed his glans into her puckered bud and Valerie pushed back as John gripped her hips and held her as he impaled her on his cock.

Valerie was feeling quite horny herself and she stroked her penis as John slid his cock in and out of her tight anus, pressing himself into her soft buttocks as he fucked her. Valerie began to whip her hand back and forth on her erect penis and John sensed that she was about to come; she was pushing back against him and grinding her backside, ensuring his penis pressed on that special place.

John sensed her urgency and fucked her harder and faster, the thwok, thwok, thwok sounds reverberating around the warehouse drowning out their groans and gasps.

John released himself deep inside Valerie; pulling her hard against him. Valerie orgasmed and her seed splattered on the floor. John twisted Valerie’s neck so he could kiss her while he came.

Valerie gave a final shimmy and eased herself forward so that John’s penis plopped from her anus. She took a handful of tissues from the desk and wiped herself then dropped the tissues in the bin and pulled up her pantyhose and knickers, pushing her still dribbling cock between her legs as she had no gaff, then smoothed out her hose and knickers as best she could. She pulled down her skirt and straightened it. John wiped himself and pulled up his pants.

Valerie sat back down, opened her purse and touched up her makeup using the small mirror in her compact, then she lit a cigarette and took an envelope out of her purse and riffled the banknotes inside it.

John sat across from her smiling, he placed the forged Batchelor of Education into an envelope and handed it over. Valerie checked the contents of the envelope to make sure no sleight of hand had occurred and happy with the contents she took the banknotes out of her envelope, snatched one hundred pounds from the bundle, and handed it over.

“Jesus Valerie! One hundred pounds for a fuck?” he whined.

“That’s a bargain John. I’m out of the fucking for money game; I just wanted to see if you had improved any,” Valerie raised her eyebrows at him and chuckled.

“I’m sure you service Miss Pops quite adequately based on that performance,” she snickered.

“Fuck you Valerie,” John was exasperated.

“You already have darling. Time to go sorry,” Valerie smiled and raised herself out of her chair.

John watched her saunter across the warehouse to the door and shook his head.

Valerie stepped outside with a smirk on her face and a rather pleasant squishy feeling in her knickers. The prossie had finished with her punter and was leaning against the doorjamb smoking a cigarette. She waved her fingers at Valerie who waved back nonchalantly. Billy waited for her next to the Jaguar they used to ferry the girls around in, and he opened the door for her politely.

Chelmsford Finishing School for Young Ladies subscribed to the 1973 Education Act which made provisions for the operation of educational trusts. This allowed Lisa to manipulate the money coming into the school from Valerie’s businesses. But it also meant that with few exceptions the faculty had to be qualified teachers.

Valerie had just gotten around three years of university by simply getting John Benstead to forge her a BA and as Lisa headed the faculty selection board, it was easy for her transition from student to teacher. She mainly taught fashion design and deportment courses but she had a college level knowledge of English and assisted with English composition but her acumen was business and she ran business courses for the girls, which she enjoyed. Any complaints from the other teachers were dealt with quickly and quietly and, as most of the faculty had recently received substantial pay rises, they were in no mood to quibble.

Valerie, Emily and Lisa had worked their way through the faculty list of five full-time teachers who taught the academic subjects, the remaining two part-timer teachers taught lifestyle related curricula. They weaned out a couple who they though would be trouble and kept the rest.

The headmaster was a weasel named Reginald Humphrey. He was an incompetent fool who had no idea what was going in his school, mainly because he hardly spent any time there. When he did attend, his main occupation was toadying to the so called wealthy benefactors who actually provided nothing, and ogling the students and staff.

“We need him gone Lisa,” Valerie said.

“Yeah but he’s going to be difficult to remove. He’s in with the hoi polloi so I don’t know how we do it?” she sounded frustrated.

Valerie grinned.

“I’ve got it covered. I seduced him about a month ago and he’s been coming around to my study to get his weekly piece of arse from me every Thursday. He will undoubtedly come around this afternoon when I’m supposed to be grading exam papers and I’ll have Emily hide in the closet and film him. Blackmail seems to be the best currency when it comes to me getting my way; that and a visit from Billy the Bottle,” Valerie smiled and Lisa blushed.

And so we come back to where this story started…

The headmaster had finished fucking Valerie and he 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 went to the ladies toilet to rid herself of Reginald Humphrey’s semen and to smoke a cigarette. She brushed her teeth and came back to her study to find Emily Milford sitting at her desk arranging the Polaroids.

“I like these shots where you can clearly see his face while he’s fucking you. You can obviously see you are trans but you can’t see your face,” Emily grinned.

“Well done sweetheart,” Valerie kissed Emily appreciatively.

Valerie strutted out of her study and picked up Lisa Meakins on the way to the staff meeting. The headmaster was stunned when Lisa tabled a motion of no confidence in Reginald Humphrey and propose he step down from his position. He was about to filibuster pompously as he usually did, when Lisa slid the Polaroids in front of him and kicked him under the table.

Reginald Humphrey called for an adjournment which was granted and he demanded that Lisa and Valerie accompany him to his study. He was surprised when he opened the door to his study to find Billy ‘The Bottle’ Butler standing just inside.

Reginald opened his mouth to speak and Billy punched him in the stomach and the headmaster folded.

“You have nothing further to say from now on Reginald,” Valerie said, closing the door.

“You’ve had a good run, made some money and even got to fuck me a few times but your time here is over. You can go quietly with a good reference from the school.”

“Or Billy here will carry you out unconscious and visit you once a week until you have no teeth left, then he starts working on other body parts. And we send copies of these photographs to your wife and every school and college to which you apply for a position.”

“Just nod if you’ll take option one,” Valerie said.

Reginald nodded whilst still bent over; the breath knocked out of him.

“You’ve got the afternoon to pack up and leave,” Lisa said dispassionately.

“Billy; see that he leaves with no fuss.”

Billy nodded and then plonked himself in headmaster’s overstuffed chair.

Valerie and Lisa went back to the staff meeting where Lisa was voted Headmistress and Valerie, Deputy Headmistress.

Valerie took off from school early and surprised Sally who also had the evening off.

Valerie dragged Sally to the bedroom and threw her on the bed.

“We’re all done darling! We run the school now, everything is ours and we’re going out to celebrate but first we are going to fuck each other bonkers!” Valerie grinned.

Sally squealed when Valerie leapt on the bed.

They kissed each other tenderly, there was no rush. Their soft lips pressed against each other’s and tongue’s tentatively slid into mouths. The kissing gradually became frenetic, their mouths locked together, tongues entwined, bodies pressed tight and legs intertwined.

They paused briefly to dispose of skirts and blouses and fell on each other again. Valerie freed Sally’s tits from her brassiere and pinched and rolled her nipples, Sally lowered her head to Valerie’s breasts and suckled and nipped at her teats. Hands snaked down soft white bellies and found satin panties bulging with hard cock. Valerie stroked Sally’s erect penis through the layer of shiny satin making her gasp and moan.

Sally squeezed Valerie’s hard phallus through her knickers, gripping it tight and stroking it. They wanked each other’s satin sheathed cocks and returned to kissing each other; their lust becoming a smouldering yearning demon that would soon need satisfying.

In unspoken agreement they turned head to toe so they could use their mouths on each other. Valerie licked at Sally’s cock through her knickers, gently biting the shaft through the satin. She raked her hands up and down Sally’s nyloned legs, knowing that the tactile embrace on her gossamer-clad legs would drive her into a paroxysm of lust.

Sally gasped and freed Valerie’s throbbing cock from her panties and took it in her mouth and suckled it. She licked Valerie’s glans and slavered at her shaft now glistening with Sally’s saliva. Valerie responded by releasing Sally’s cock from the confines of her knickers and sucking it deep into her mouth and trilling her tongue on her fraenulum.

They sucked each other’s cocks, stroking legs and squeezing buttocks, driving their carnality into overdrive.

Valerie spun around and mounted Sally, lifting her legs high and putting them over her shoulders. She nuzzled Sally’s stocking-clad calf as she probed at her anus. As soon as her glans found Sally’s puckered entrance she pushed forward and drove her hard cock deep inside her lover.

Sally squealed with delight and writhed and bucked under Valerie as Valerie’s cock filled her anus and nestled against her prostate. Immediately waves of pleasure emanated from that special place and her cock began to leak preseminal fluid.

Valerie gripped Sally’s leaking penis and stroked it as she fucked her lover, thrusting deep inside her and then retracting her penis until her glans was once again nestled in the pink flower of Sally’s anal bud, then she pushed slowly forward again making Sally shake with lust.

Valerie lowered her face to her lover’s and they kissed as they fucked, their tongues entwined as Valerie slowly increased the tempo of their fucking. Sally ground her buttocks against Valerie, encouraging her to fuck her harder which Valerie was obliged to do.

Valerie fucked Sally hard and fast with deep strokes, they both gasped into each other’s mouths; Sally crossed her ankles behind Valerie’s head and lifted her bottom up off the bed to meet Valerie’s thrusts.

Valerie orgasmed and her warm, glutinous spunk flooded Sally’s derriere, oozing out of her, as her anus filled, dribbling down the crevice of Sally’s buttocks as Valerie continued to pound her cock in and out of her. Sally shrieked as Valerie’s hot seed splashed over her prostate and that thick cock distended her sphincter, driving her wild with desire and triggering her climax.

Valerie stroked and squeezed Sally’s quivering phallus and was rewarded with a spurt of creamy issue that soon became a torrent of milky white semen.

They kissed and fucked each other, relishing every sensation and drawing out the divine rapture of their lovemaking until they were gratified; then Sally lowered her legs Valerie withdrew and they cuddled and kissed until they nodded off to sleep, their juices drying on their flesh.

“Come on honey; you always take forever when we’re going out,” Valerie chided Sally who was putting the finishing touches to her makeup in the ensuite bathroom.

Valerie downed the last of her Chardonnay and stubbed out her cigarette.

She was wearing a floor-length red satin evening gown that clung to her every curve. She had accessorised with gold jewellery, red plush high-heeled pumps and a gold beaded clutch. Her hair was perfect as was her makeup and she was anxious to go. Billy waited in the Jag downstairs.

Sally came out of the bedroom looking just as stunning as Valerie. She wore the same dress only in blue and had accessorised with silver accoutrements.

“You look gorgeous!” they said in unison and air-kissed so as not to spoil their makeup.

They made their way gingerly downstairs in their highheels and Billy helped them into the back of the black Jaguar. They soon arrived out front of Bocca di Lupo, one of London’s finest restaurants.

All heads turned their way as they approached the Maitre D.

“I have a booking for Valerie Swindon,” Valerie smiled excitedly.

“Of course. Come with me please ladies,” the Maitre D led them through the crowded restaurant.

Valerie was surprised when they arrived at one of the small private dining rooms.

“No, I’m sorry. This is wrong. I ordered a table for two,” Valerie said to the Maitre D, the confusion evident in her voice.

“A slight adjustment to the seating arrangement Mademoiselle,” the head waiter opened the door to the petite dining room and ushered them in, closing the door behind him.

Sitting at a table set for six was a large man smoking a cigar, his swarthy complexion betrayed his Italian descent. He was ruggedly handsome despite his size and his pin-striped suit was obviously hand tailored and expensive.

The lady sitting beside the large Italian man was an attractive lady in her forties. She stood up and flashed a brilliant smile.

She was wearing an ankle-length red satin gown worn low on her shoulders, with long sleeves; split to her thigh which revealed shapely legs clad in sheer black stockings. The fabric of her dress clung to her curvaceous body. She had accessorised with red kitten-heels and silver jewellery and her long blonde hair was combed out straight and worn down to her waist. It glistened in the subdued lighting of the restaurant. Her makeup was dark and striking; her lipstick bright red when she smiled.

“Please allow me to make the introductions. I’m Michelle Murphy and I believe you know John Benstead,” she indicated John who sat there with a sardonic grin on his face wearing a dark blue Italian-cut suit.

“And beside him is Miss Candace Pops.”

Michelle pointed to a beautiful girl in her early twenties, her face was framed by silky straight brunette hair cut with a fringe. She stood up and offered her hand. She was dressed in an airline hostess uniform consisting of a light blue A-line skirt, with the very short hem; a form-fitting jacket with silver piping along the lapels, a long sleeved white satin blouse and black patent leather four-inch heels.

Valerie and Sally leaned over the table and shook her hand; both gobsmacked and speechless.

“Sorry. I had to come straight from work; my flight just got in from Singapore,” when she smiled, she lit up the room.

“And your host tonight is Mister Tony Carlotta,” Michelle extended her hand towards the large, handsome Italian gentleman.

Tony rose and smiled. His smile reminded Valerie of a crocodile and she shivered involuntarily as she realised who this man was.

“Ladies…Please sit…I want to make you an offer you can’t refuse.”

The End


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