Finishing School For Ladies Ch. 04

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Transvestite at finishing school is molested.
4.1k words
4.6
15.6k
17

Part 4 of the 11 part series

Updated 06/08/2023
Created 09/05/2017
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MicheleNylons
MicheleNylons
3,938 Followers

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.

MicheleNylons
MicheleNylons
3,938 Followers
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