Finishing School For Ladies Ch. 01

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.

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 and plaid skirt. 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 from 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, two steps ahead of your friends and family, and five steps ahead of Tony Carlotta. Keep things simple but keep them slippery, if you know what I mean," he winked and tapped the side of nose at his young protégé knowingly.

"Son; I'm going to give you three series' of numbers that I want you to remember. If anything every happens to me and your mum, you use those numbers as soon as you can because they will be your salvation," his father explained to him how they worked.

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 the three sequential number codes on them. Within half an hour William had moved three hundred thousand pounds from three accounts in the Virgin Isles to one account 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 his Grand Cayman account into an account with the Commercial Bank of London. 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 both himself and 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 stepfather 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 stepdaughter's tutelage by cashier's cheque annually and he would send Valerie any incidentals she needed.

Mr Styles would of course take his stepdaughter 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, stepfather 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 stepdaughter 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. And of course; please don't forget the cashier's cheque.

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 stepdaughter 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 bought 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 to know what to look for. 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 for a man which is good and we can do a lot with your hair," she smiled.

"Your voice is good too. It doesn't have a male timbre; it sounds very femme-fatale, a smoky Betty Davis sort of quality."

"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...