tagTranssexuals & CrossdressersFinishing School For Ladies Ch. 06

Finishing School For Ladies Ch. 06

byMicheleNylons©

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 was 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.

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byMicheleNylons© 4 comments/ 3087 views/ 9 favorites

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