Finishing School For Ladies Ch. 01

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Transvestite hides in ladies finishing school, sex ensues.
6.3k words
4.54
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63

Part 1 of the 11 part series

Updated 06/08/2023
Created 09/05/2017
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MicheleNylons
MicheleNylons
3,910 Followers

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 she was not what you would you call a classic beauty. 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 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 torso 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 flood her back passage and her 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, you will 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. It would likely be their last; if her plan came to fruition.

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 a strand of tobacco from her lip and began to daydream. She thought back to how this had all began...

At age eighteen William Styles was the unluckiest lad alive; twice orphaned, once at age two and now again at age eighteen. 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 only eighteen but he's shit out of luck. If his father hadn't been so greedy he wouldn't be in this mess," the male social worker said.

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

"He's been left a shitload of money in inheritance but he won't keep it long. As soon as he gets access to all that cash the boss will make him hand it over," 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' 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.

The plane crash was no accident. His dad was the business manger for a London based organised crime boss named Tony Carlotta and had been caught siphoning off funds. The plane crash was the result of Tony's revenge. Tony had bribed his people in the court system to ensure William was assigned to a Borstal School so that Tony could get his hands on William and make him hand over his considerable inheritance.

William was introduced to the two social workers, now his guardians, who had been assigned to look after him until after the funeral. After the funeral, being a ward of the state and incriminated in his father's embezzlement scheme, he would be put into 'Borstal training' until he was at least twenty one.

William knew he wouldn't stand a chance in the Borstal. 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 hip. It was the seventies and fashionable teenagers were mostly slim, androgynous types, with long hair, wore chic 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 most likely 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 interred in the Borstal until he was twenty one, 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.

But William wasn't stupid. He knew what awaited for him at Borstal was nothing compared to what was going to happen to him when the court processed the probate on his father's estate and he inherited the cash his father had stolen from Tony Carlotta. Tony would use whatever techniques he needed to make William hand over his inheritance.

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, normally social services wouldn't try too hard to find him; being eighteen 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. 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 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. Her blazer was open and revealed a tight blouse which 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 idea of the girl who appeared to be cross between 'Madeline', a character from the children's books written and illustrated by Ludwig Bemelmans, and a Saint Trinian's schoolgirl drawn from the pen of Ronald Searle. He had pored over the books and the cartoons when he was younger, 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 Saint Trinian's.

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.

The feel of the garments bought back memories of him standing in the doorway to his mother's bedroom watching his mother with her trim figure; her back to him as she slid her panties up her stocking-clad legs and smoothed them tightly around her. She, turning her head and seeing him there and smiling at him. Her hand extended, beckoning him into her bedroom.

William suppressed that memory but he had to try the silky garments on.

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 the 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.

MicheleNylons
MicheleNylons
3,910 Followers
12