Hostess With Mostest By Michele Nylons
Chapter One
"It's just not fare!" he lamented.
The piece of paper he has tossed on the desk was a letter of rejection from Goldwing Airways to whom he had applied for job as a flight steward.
The letter joined five other letters of rejection from the other major airlines.
Chris wanted to be an airline steward more than anything else in the world. He was currently employed as a head waiter at one of London's leading restaurants `Bocca di Lupo'. He had worked there for five years, starting in service at seventeen years old, working his way to the top.
People thought that being in service was an unskilled trade but that was not the case. Chris had understudied some of the best people in the service industry and was a master at place settings and table decor, an expert in describing every dish on the menu and which wine to pair with which dish. He knew how to greet very important people, seat them, make them comfortable, and take care of their every desire whilst remaining discreet and tactful. It was an art. He had also undertaken several external studies to improve his knowledge.
But what he really wanted was to be an airline steward.
Born in the 1953 to parents who were affluent professionals, he had flown with them countless times as he grew up. In the sixties flying was for the middle and upper classes. People dressed for the occasion and air travel was considered something special.
His parents normally flew First Class where there was usually one male head steward or Chief Purser as they were known then, the name steward being adapted from the maritime industry. Of course now they are called flight attendants or cabin crew.
Chris loved the romance of flying and he envied the elegant men dressed in three-piece suits who directed the rest of the cabin staff and only waited on the most important VIPs.
His parents joked with him that such a job was beneath him and that he should study hard and if anything, become a pilot and sit at the front of the plane not become a `flying waiter'. Wanting to be an airline steward was for girls they joshed him.
But Chris was adamant that he wanted to be an airline steward and had taken a job in a very respectable restaurant in order to prepare himself and hopefully make himself competitive.
But there were so many obstacles. He scoured in-flight magazines and job sites looking for announcements from the airlines advertising positions for stewards. When he found them they usually read something like this:
`Ladies; if are you a good conversationalist no younger than 20 no older than 27, no shorter than five feet two and no taller than five feet nine, slender, well proportioned, no more than 10 stone and unmarried, we have an exciting job for you. A job that involves travel, glamour, and responsibility. A career to see you through to your mid thirties. Goldwing Airlines is accepting applications for flight stewardesses now. Apply in writing and attach your CV. Males may be considered for some positions.'
In the nineteen seventies only ten percent of stewards were male. And he had it on good authority they were mostly gay males. It was almost impossible to get a job as a male steward. Only five out every one hundred applicants were accepted for training as a flight steward and as ninety percent of the accepted applicants were female the odds were definitely not in his favour.
Chris decided to go down the pub and drown his sorrows with a few pints with his friends from the restaurant.
Of course he began to lament about his latest rejection and they had all heard the same story before and were a bit fazed by it.
"I'll never make it as a flight steward!" he whined after his third pint.
"Well maybe you should just dress in drag and apply as a stewardess," one of his friends joked.
And that was how this story started.
Chris tossed and turned that night. He felt bereft. He had tried his best. He had not only lodged applications to the airlines he had pestered them on the phone and written numerous letters to them espousing his virtues as a professional service provider. He had included many references and recommendations but the stock answer had been:
`Sorry sir, all our positions for male flight stewards are filled and we are only accepting applications from potential hostesses.'
He arose early. His little flat was warm, at least the heating worked well, and he padded around naked making himself tea and toast. He sat at his little desk and flicked through his collection of in-flight magazines.
There were very few pictures of male stewards and those he had clipped out were of distinguished looking men in suits, some wearing aprons, serving satisfied looking genteel types in the first class cabin. Most of the pictures of cabin staff were of long-legged, short-skirted, slim, attractive young women leaning over seated male customers serving meals or drinks.
The pictures were deliberately aimed at the male dominated passenger market.
America's National Airlines had their ad: I'm Cheryl – Fly Me' on posters near every airport and in every travel agency and he had read the book Coffee Tea or Me?'
It was so unfair that the market was so sexist. The seventies was a decade where the glass ceiling remained firmly in place and it was ironic that males were disadvantaged in this one industry.
Chris had a full-length mirror that he used to make sure that every aspect of his dress and bearing were correct before he ventured out to work. He stood naked in front of it and looked at himself.
At five feet six inches he was not a tall man. He was very slender with a tiny waist. He had not excelled at sports at school but could have been a competition ballroom dancer, he was lithe and graceful on the dancefloor, but he didn't have the height. He was shorter than some of his dance partners. His alabaster skin was smooth and unblemished, and except for a little tuft of pubic hair and a few strands under his arms, his body was hairless.
Chris had shoulder-length light-brown hair which he wore long and straight but was expertly cut. It was the fashion for men to have long hair, but his industry had no time for scruffs and he was always elegantly coiffured. The female staff at Bocca di Lupo joked that he spent more money caring for his hair than they did. He wore a simple gold sleeper in each earlobe, very avant-garde.
He jokingly tucked his scrotum and penis between his legs. He struck a coquettish pose standing on tiptoe and turned one knee inwards, he put one hand behind his neck and crooked the other arm so that his hand rested on his waist. He lifted his chin and turned his face side on. His handsome face was androgynous with well defined cheekbones and full lips.
"I'm Christopher – fly me," he said jokingly to the sparse empty flat.
"No; that's not right is it?"
"I'm Candace – fly me!"
He laughed at his own joke. Then he stopped laughing.
He struck a series of poses, adjusting the posture of his slim supple body to mimic those of the stances of the fashion models he had seen in magazines.
"Jesus!" he whispered.
"No I couldn't...could I?" he raised an eyebrow.
"Don't be stupid!" he berated himself.
But his brain was ticking over. He was twenty two and if he didn't break into the world of flight stewards soon it would be too late. He would be too old.
"Forget it!" he admonished himself and went to the bathroom to prepare for a busy day.
At Bocca di Lupo Chris found it hard to concentrate and the Maitre D' scolded him.
"Christopher! What is wrong with you today? It's like you are not here!"
During his allotted break between the lunch and dinner service he did what he usually did, he strolled past the downtown travel centre. A full sized cardboard cutout of an airline hostess in her smart sexy uniform proclaiming `Fly me to New York' took pride of place in the window.
"Fuck! What chance have I got competing against that!" Christopher cursed under his breath.
He moved past the travel centre, today he found it depressing, and looked into the other store windows not really concentrating on what he was looking at until his attention was drawn to a mannequin on display in an Op Shop window. The mannequin was dressed in a sixties era airline hostess uniform.
It consisted of a dark blue skirt and a jacket with silver buttons. There was a silver winged badge on the left breast.
Chris stared at the uniform for what seemed like ages. It wasn't the double-breasted, three-piece suit that he wanted to wear as a male flight steward but he had to admit it looked smart.
"Don't be stupid!" he uttered to himself and went back to work.
But he couldn't help thinking of the possibility. The absolutely ridiculous possibility. The absolutely outrageous possibility that he could pass as an airline hostess. In the early hours of the morning after his shift, and after most of a bottle of scotch he made a decision.
"Fuck it! I'll apply for a stewardess position and if I get it I'll prove to them that their discriminatory policy is bollocks! That I'm just as capable as any woman at being a flight steward," he said, downing his last drink.
The next day was his rostered day off and while he was still a little intoxicated, which gave him fortitude, he went down to the Op Shop arriving as soon as it opened. He figured there would be very few, if any, customers that time of day.
The shop smelled of mothballs and was poorly lit. There were racks and racks of cheap second hand clothing on hangers divided into men's, ladies, boys and girls sections.
There was one portly but attractive middle-aged lady behind the counter folding clothes. She eyed her solitary customer suspiciously, or so Chris thought, as he made his way through the ladies section to the window where the mannequin stood in the window. He waited until there was no passing traffic outside and spun the price tag around.
"Five quid. Not bad," he mused.
He got a closer look at the uniform and he could see it was well worn but clean. No stains that he could see. All the buttons were there.
"But will it fit me?" he whispered to himself, lost in thought.
"Well why don't we find out," the shop assistant whispered back.
Chris jumped in the air he was so startled. He hadn't noticed the lady creep up on him.
"It's ok. We get your type in here all the time. Crossdressers are some of our best customers," she smiled at him.
Chris was about to profoundly claim innocence of being any sort of crossdresser; he was no such thing!
But then wasn't that exactly what he intended to do?
The lady seemed nice enough; she was smiling sweetly at him so why not take up her offer?
"Well I'm a little nervous, this is my first time," he stammered.
"Oh yes I'm sure it is," the lady replied sceptically.
"Anyway I'm Doris and I'm here to help you dear."
"I'll go and close the shop so that no one comes in and you can try it on in the fitting room. I don't get many customers this time of day anyway and none that are willing to part with five pounds," she tottered off to the entrance and closed and locked the door.
She flipped the open/closed sign to closed.
"You go over to the fitting room and strip down to your skimpies and I'll pass you the uniform ok?"
Chris was about to object. He was uncomfortable getting down to his underwear with only this lady in the store but he realised he was being stupid. How lucky was he to find a lady like this who had no objection to helping him try on ladies clothing?
The `fitting room' was just a hardboard cubicle with a ratty curtain across it but it would do. What else did you expect to find in an Op Shop?
He took off his shoes and his flared jeans and his bodyshirt. He didn't wear a vest under his bodyshirt, nobody did; bodyshirts were designed to be worn next to the skin. He hung his clothes from the single hook provided.
The lady passed the skirt and tunic through the curtain and Chris took them from her. This was so strange it was surreal. He hung the jacket on the hook with his pants and shirt and stepped into the skirt.
It felt weird pulling it on but it was lined with some sort of silky material that felt nice and cool against his skin. He buttoned the waist and did up the zip on the side. It sat very snug, low on his hips and the hem rested just above his knees. It felt like it might be too small for him. Anyway he pulled on the jacket which was also lined with the satiny material and after figuring it out that it buttoned on the opposite side to what he was used to, he buttoned it up. It too was snug.
"Well lets see then," Doris was just outside the curtain.
"It's ok missus; I think it's too small for me," Chris blushed.
"Bollocks! I can size anyone just by looking at them and that should fit you to a tee," Doris swished the curtain open and Chris flushed a deep red.
"Well there's your problem right there," she said and stepped forward and hitched up the waistband of the skirt so that it sat on Chris's waist instead of his hips.
Doris adjusted the hem and straightened it, then rearranged the tunic. She fussed around him for few seconds tugging and pulling on the garments.
"There! How's that?" she beamed.
Chris looked in the spotted mirror at the back of the cubicle. The uniform did fit him. Perfectly.
"Ahem. The skirt's a bit short," he looked down at his lily-white legs still clad in his purple socks.
"That's how they wear them sweetie. Those hosties like showing a bit of leg," she teased.
"Put on a nice pair of sheer tights, pantyhose the Yanks call them, a nice pair of heels and you'll be a knockout," Doris grinned.
"What about a blouse?" she asked.
Chris was still mesmerised; looking at himself in the mirror.
"You'll need a blouse to go under the jacket. Hang on a bit I've got just the thing," Doris seemed to enjoy dressing Chris up.
Chris just stood there bemused and let her take charge.
She came back with a cream satin blouse and helped him out of the jacket and into the blouse which befuddled Chris with the backwards way of buttoning so he left it to Doris to button him up. She showed him how to unbutton the waist of the skirt and unzip it so he could tuck the blouse in then she zipped up the skirt again.
"Here; I'll show you a trick you can use," she beamed at him.
Doris shot her hands under the skirt, grabbed the tail and the front of the blouse and pulled them down. It happened so fast that Chris didn't have a chance to become embarrassed or say anything.
Anyway it worked. The blouse was nice and snug except for the chest area.
"When you put your falsies in your bra that'll fill it out and it'll look great," she smiled.
Now Chris really was bewildered.
"What?"
"Your false tits dear! Surely you have a pair don't you?" Doris smirked knowingly at him.
Chris decided not to answer.
"Anyway, a nice B cup will suit you. Most of your type go double Ds and try to look like Jayne Mansfield for some reason; but a nice B would suit you," Doris said.
Chris had absolutely no idea what she was talking about.
"We don't sell underwear dear. Not allowed to. Try Debenhams on the High Street, they have nice stuff and they're cheap," Doris sniffed.
"I'm betting you have some lingerie already but if you need to buy some I'd say you're a size thirty four bra and size ten knickers," She quipped.
`Knickers and bras! I hadn't even thought about underwear,' Chris postulated.
"I can give you the blouse for a quid and I think that's you done," Doris was obviously ready to reopen.
Chris took one last look at himself. The clothes fitted him nicely but he still looked like a bloke in a dress.
"Shit! Shoes!" Chris looked down at his feet.
"No profanity please. What size are you luv?" she asked.
"I'm an eight in a man's," he replied.
"Let me go and look. Sit on the stool there so no one can see you though the window," Doris directed him and came back in less than a minute with three pairs of ladies shoes.
They were all black high-heels and after she took off his socks she managed to fit him into a size ten at the second attempt. Chris stood up and promptly fell flat on his arse.
Doris laughed and her whole body shook.
"Need a bit of practice dear?" she helped him up.
With her assistance Chris was able to walk down one aisle and back and by then he'd had enough.
Doris put his purchases into two large plain brown paper shopping bags.
"Five quid for the uniform, a quid for the blouse and a quid for the shoes, that's seven quid," Doris held out her hand for the money.
Doris rung up Chris's purchases on an old clunky till and then saw him to the door.
"Come again any time love. We love your sort here, you always spend big," she laughed and showed him outside.
"What the fuck am I doing?" Chris said to himself as he made his way home.
When he got home he laid out his purchases on the bed and looked at them.
"Fuck it! Nothing ventured nothing gained," he sighed.
Chris set his resolve and went back out and caught a bus across the city until he found a Debenhams that was no where near where he lived or worked. He did not want to be seen by anyone he knew making his next purchases.
"Right! This shouldn't be too hard. Just remember you're buying them for your girlfriend," Chris reassured himself and went straight to the lingerie section.
There were rows and rows of panties and brassieres, all different sizes, colours and fabrics. Luckily they were grouped together by make and design and he'd already decided on basic black. He didn't know anything about women's fashion but it made sense to him that black would work with the dark blue uniform.
He mooched around, luckily undisturbed by pesky shop assistants, and found a pair of full cut satin panties on a small hanger with a 10 in a coloured circle which obviously indicated the size. Above the rows of panties hung the matching bras and after a bit of fiddling around, the sizes seemed mixed up, he located a couple of size 34s and remembered Doris' advice and found a B cup.
Chris dropped them in the shopping basket he was carrying and placed a newspaper he had bought earlier over them. He didn't want anyone seeing his purchases.
The next aisle over was hosiery and if he thought the lingerie section was boggling this looked worse. But it turned out easier than it looked. He picked up a package of pantyhose and examined it and found there was a convenient size chart on the back.
Being five foot six and of slender build he needed a size small. He saw a rack of Pretty Polly tights, although he preferred the word pantyhose, tights to him were the thick woollen leggings women wore in winter. He was a leg man and loved the sight of a well turned ankle or shapely thigh clad in sheer hosiery.
He selected one pair of black and one pair of nutmeg brown ten-denier Pretty Polly tights and put them in his basket.
"Right! That was easier than I thought. Let's see how we go now," he was feeling confident.
Until he came to cosmetics section which was a series of brightly lit counters behind which were pretty young women only too willing to help.
"Fuck! Now what!" he was hoping he could just grab some makeup and throw it in his basket.
But when he saw the array of cosmetics he realised that he didn't have a clue what he needed and no idea how to use any of it.
To make matters worse one of the pretty little things was making a beeline for him.
"Can I help you?" the perfectly made up and coiffured young lady asked with a dazzling smile.
"Well I'm not sure what I want," Chris stammered.
The girl looked at him quizzically.
"I mean I'm buying cosmetics for a beginner if you know what I mean," he blushed.
"Oh you mean a young girl about to start wearing makeup? Your sister? Niece? It can't be for a daughter surely," and she flashed that smile again.
"Well yes, my niece. But she's not a kid. She's, um, seventeen but my aunt is very strict and she's only allowed to wear makeup when she turns eighteen," Chris thought his anecdote sounded stupid but he wanted real makeup, not some kids play cosmetics.
"I've got a girlfriend and her dad's a strict Catholic so I get it. You are such a wonderful and caring uncle buying her makeup for her birthday," she smiled.
"Yes I guess I am. Anyway she doesn't have anything and of course I have no idea what she needs," Chris tried to sound as stupid as he felt.
"Well come over here and look at these," she directed him to series of shelves that held cosmetic cases that appeared to be filled with everything a woman could need.
Some were as small as a box of tissues and some were as big as a tradesman's toolbox.
"Well you only turn eighteen once, so what about that one?" Chris pointed to the biggest.
"Well yes that does have everything from concealer to lipstick. It even has a selection of nailpolish. It's expensive but she won't need to buy anything else for a very long time," the girl grinned, hoping to make a sale.
"I'll take it," Chris was relieved.
"Can I pay here and have you wrap it?" he did not want to lug the huge cosmetics kit to the checkout.
The lingerie he could explain away as presents for his girlfriend but with the makeup too...that might be a hard sell.
As it turned it didn't matter. He forked over twelve quid at the cosmetics counter and the girl wrapped the big box in birthday paper. When he got to the checkout counter the girl was so overworked that she just looked at the pricetags and rung up the lingerie and pantyhose on the till and snatched his money, gave him change and was ready for the next customer.
Chris took his purchases home and laid them out on the bed next to the airline hostess uniform, the blouse and the shoes.
He stood back and looked at the pile of ladies clothing and the huge box of cosmetics and the enormity of what he was thinking of doing washed over him. He didn't know a thing about cosmetics and although he considered himself a connoisseur of women, he had certainly undressed more than a few, he had no idea how to present himself as one.
"What was I thinking?" he lamented.
Rather than try to work out how to apply the makeup, dress himself or master feminie traits, he decided he would wait until he could find a confidant to assist him. He wracked his brain but for the life of him he couldn't think of single woman he could trust to help him.
Once again he decided to sleep on it and see what fortune presented to him.
Fortune came his way in the most unexpected of circumstances.
Two days later he was going over the table assignments at Bocca di Lupo. One of his tasks was to ensure the valued VIP customers got the best tables. It didn't mean the richest people got the best tables; celebrity and power counted as much as money.
As he studied the list he came across a table for two booking for a Mr Tony Carlotta and Ms Michelle Murphy.
Chris instantly recognised the name of the infamous Mafioso and also that of Ms Michelle Murphy as her later ego, Cherri Pops.
Michelle Murphy was famous for being the rock star Cherri Pops; well for a short time she had been anyway. She used to play lead guitar in the rock band Transvixen, celebrated for having two transvestite guitarists. He had been to one of their concerts and Cherri was gorgeous. You would never have known that she was not a woman. He had also, nearly a year ago to the day, waited on Tony and Michelle during an intimate dinner two at the restaurant where he had once again been taken aback by her beauty and femininity.
He wondered if he dare ask her for help. He hardly knew her, but if anyone knew anything about crossdressing she did. He decided to try to engage her assistance and if she was insulted and complained to the owner of the restaurant so be it.
That night he made a great fuss of Tony and Michelle but made sure that although they benefited from his excellent service, he was not intrusive. His chance came when Michelle took a bathroom break. He watched as she glided across the restaurant and noticed all the men turn their heads to watch her and the other women's looks of jealousy.
Michelle wore 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 as she strode across the floor. The fabric of her dress clung to her curvaceous body. She wore 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.
Chris didn't know this but the dress had significance for Tony and Michelle; she had worn it when they had their very first dinner together Bocca di Lupo. They became lovers that night but the romance didn't last for long, however they reunited at Bocca di Lupo once a year for old times sake.
Michelle was leaving the expansive ladies room when Chris approached her. She recognised him and smiled. Chris took a deep breath and intercepted her.
"Ms Murphy, may I have a minute?" he asked.
Michelle's continued to smile but he could see that she was also a little discomfited.
"I'm sorry I won't be long," Chris apologised, almost ready to give up, but Michelle didn't try to push past him so he went on.
"I know you were once famous for being Cherri Pops in Transvixen," he started.
Michelle reached into her purse scrambling for a pen thinking that he was an autograph hunter.
"No I'm sorry it's not that. I need your help. I want to be an airline stewardess but I don't know how to be a woman," Chris blushed realising how stupid he sounded.
Michelle burst out laughing; she doubled at the waist it was so funny.
Chris blushed a deep red; he began to tremble and actually shed a tear.
Michelle saw his distress and put her hand on his arm.
"I'm so sorry. I shouldn't laugh at you, especially given my own history."
"Look; what you said really intrigues me but I can't chat now. No one keeps Tony Carlotta waiting," she laughed.
Chris was despondent, but there was a ray of hope.
Michelle handed him her business card.
"Call me tomorrow morning. You can buy me lunch and tell me your fascinating story," Michelle's smile could melt hearts.
It melted Christopher's and he flashed his best smile back at her and with a flourishing wave of his arm, invited her to return to her table.
Chris hardly slept that night. He was almost determined to call Michelle and call it off and with trembling fingers he dialled her number. She picked up on the third ring and Chris half expected her to fob him off. She sounded delightful on the phone but more importantly, enthusiastic.
They met at a small tea shop. Chris was there first and very nervous. Michelle arrived wearing a mauve business suit, black heels and with her blonde hair piled high. Her makeup was perfect as usual and Chris was amazed at her grace and elegance. `She used to be a man; who would believe it?' he mused.
Chris stood and tended to her chair as she sat down, crossing her legs at the ankles. Chris had begun to study women's mannerisms.
They ordered salads and a bottle of Chianti and after the wine was poured Michelle smiled at him and studied his face inquisitively.
"Have I got something on my lips or in my teeth?" Chris blushed and wiped at his mouth.
"No I'm looking at the shape of your face, your lips and your hair. Us special girls have a saying: `pretty boys make pretty girls' and you're a pretty boy," she grinned.
"So you have me intrigued. You know I was once Michael Murphy, but that seems so long ago now; then I became Cherri Pops to play with Transvixen although I was already crossdressing by then. And then I transformed into the full time trans woman you see before you. It's no secret; in fact there have been a few puff pieces written about me over the last couple of years."
"Tell me everything. And I mean everything," she grinned and sipped her wine.
She lit a cigarette and Chris noticed that she hadn't touched her food. No wonder she stayed so slim.
Chris told her everything.
"So let me get this straight. You intend to pass yourself off as a woman, get selected for flight service training, graduate as a stewardess and then reveal yourself to be a man?" Michelle was sceptical
"In a nutshell, yes," Chris replied.
"To what end?" Michelle asked.
"To prove to the airline industry that they should take on more men I guess but more importantly I want that job!"
"But even if you get away with it, and that's a big if, what makes you think they will hire you when they find out you deceived them?" Michelle had ordered coffee and she stirred it slowly.
Chris watched her long elegant fingers lightly grip the small spoon; her ruby red fingernails circling the cup.
"I have to admit I hadn't thought that far ahead. The more I think about it the more I think the idea is crazy," Chris sighed.
"Not necessarily Chris," Michelle grinned mischievously.
"What if you threatened to go public. Imagine the headline: `Man graduates as stewardess – airline dumbfounded!'" Michelle grinned.
"I love it! You're unlikely to succeed, there are so many obstacles that you probably haven't even thought of. But I love the premise of it."
"You realise that if you get accepted into their training program you will have to live full time as a woman to carry this off?"
"Well that's another thing I hadn't factored in. This is so complicated," Chris smiled wanly.
"Look. I love helping the underdog so I'll tell you what I'll do. I'll give you a crash course in crossdressing. It's actually not that hard if you have the right clay to mould and I think I can do something with you."
"But that's all I can do. I'm a busy woman but I'll help you get started and then it's up to you. If you are convinced you can pull this off after I transform you for the first time, then go at it with my blessing. I'll want you to keep in touch and tell me how it goes," Michelle grinned.
"When do we begin," Chris smiled enthusiastically.
"No time like the present. I'll be finished around seven tonight so have a nice long bath and shave any body hair you may have but you don't seem to have much. In fact, without bring rude, the few times I've seen you I've taken you for gay," Michelle touched his hand.
"Yeah I get that a lot," Chris smiled back at her.
"Tonight then. Your place at seven thirty. Write your address and phone number on this napkin," Michelle handed him her napkin.
It was untouched except for a scintilla of her lipstick where she had dabbed it to her lips.
Chris was nervous to say the least that evening. He took a bath and soaked himself and shaved the few stray hairs on his body, legs and underarms and then thought `what the hell' and shaved away his meagre patch of pubic hair. He carefully shaved his face and then slipped into a bathrobe, the heating was cranked up and his little flat was nice and warm.
He sat with a tumbler of scotch and waited nervously.
Michelle arrived twenty minutes late and she breezed past him in a miasma of perfume when he opened the front door.
"It's colder than a witch's tit out there," she said making her way directly to his little bar and poured herself a scotch.
"Do you mind?" she raised the glass and an eyebrow to him.
Chris admired her confidence. She took off her coat and he took it from her and folded it over the back of an armchair.
Michelle was still wearing the same mauve business suit and black heels that she had worn to lunch. She had obviously come straight from work. She sipped her drink and pulled at the pins holding up her hair and it tousled down around her shoulders. Her makeup was still perfect. Chris once again contemplated just how much he didn't know about being a woman.
"Right. Lets get started. What have you got for me to work with," Michelle was all business.
He led her into the bedroom where his purchases were laid out.
"Mmm, just the one outfit; and how cute. It looks like a hostie's uniform," Michelle smiled.
"And the world's most biggest fuck off cosmetics case I've ever seen!"
Chris blushed.
"I didn't know what I needed so I bought that," he explained.
"Well you certainly have everything covered in the makeup department," she said mooching though the array of cosmetics in their little drawers.
"Sit down in front of the bureau. I'm glad to see it has a nice big mirror and turn on those lamps so we have good light."
Chris had a little manicure set on the bureau and Michelle unzipped it and took out the tweezers.
"You have eyebrows to die for. They only need a little shaping," Michelle lifted the tweezers and went to work.
Chris winced at first but Michelle gave him a look that could only be interpreted as `stop being a cry baby', so he stopped and paid attention to what she was doing.
"Ok we've shaped your brows. All you need to do now is to keep them like that; it'll take a couple a minutes once a week at the most.
"Right! Down to business. Pay complete attention!"
She cleared a space in front of him and began to lay out the cosmetics she intended to use and explained what each would be used for. Chris was quite fascinated and he found the little tubes, bottles and pencils intriguing.
"Ok watch me carefully and I'll explain as I go," Michelle commenced makeup instruction.
"This is concealer, we will use this sparingly to cover any blotches, spots or nicks; although I know a lot of girls who would love to have your skin," she held his chin up under the light.
She painstakingly applied cosmetics to Chris's face until he looked perfect and then had him remove the makeup, then had him do it again and again until he made a fair job of it.
"This liquid soap we are using to remove your makeup will be hard on your skin. Go out tomorrow and buy some proper makeup wipes and face cream. In fact let's make a list of all the things you will need as we progress," Michelle said.
Chris opened a drawer and took out pen and paper and began to write.
"You will need to get your hair properly styled. I'll cut you a fringe tonight but I think you should take a few inches off and have it cut into a bob. It will suit your face and lots of guys are wearing it like that now anyway."
She parted his hair down the middle and gave him a fringe which she painstakingly cut straight. She snipped away at the sides and back to even it out but didn't take much off.
"That'll do for now. What do you think?" Michelle turned Chris to face the mirror.
He didn't recognise himself. What he saw was a beautiful young woman with smoky eye makeup, long black lashes, perfect skin, rouged cheeks and red lipstick. Her face was framed by silky straight brunette hair cut with a fringe.
"Wow! I honestly can't believe that's me," Chris exclaimed, the timbre of his voice rising as he spoke.
"That's it! That voice right there! Your voice is more soprano than tenor anyway but that pitch is perfect. It's very femme with a hint of smokiness; very sensual," Michelle explained to him.
"I'm going to leave you some walking and posture exercises and while you are doing them I want you practicing your femme voice. Just read aloud from a book or magazine but practice, practice, practice until it comes to you naturally."
"I can't even remember what Mike Murphy sounds like anymore. This is my natural voice now." Michelle explained.
Chris couldn't take his gaze away from the mirror. He was fascinated by his own reflection.
Michelle leaned in and he found her closeness uncomfortably stimulating. Michelle sensed it and smiled. She rummaged in her purse and produced a little perfume bottle which she spayed liberally on the nape of his neck. She put little silver drop earrings in his ears and a matching necklace around his neck.
"My gift to you. Keep the perfume too," she murmured; her lips brushing his ear.
Chris shivered and she smiled.
"I can't accept," Chris swallowed.
"Nonsense, a present from one girl to another," this time she lightly kissed his ear and Chris shivered again.
"Ok Candi Pops, here comes the best bit. Getting dressed," she grinned into the mirror.
"Candi Pops?" Chris said, bemused.
"Well I used to be Cherri Pops and my erstwhile girlfriend is Panty Pops, so you can be Candi Pops until you decide on a femme name," a smile lit her face.
Chris; now Candi, smiled back at her.
"It really helps to have a female name. It works on your mind and makes you think like a woman rather than a man," Michelle said.
Chris got the point. He found that thinking of himself as `Candi' changed his frame of mind, especially when he looked in the mirror. There was no way the gorgeous creature looking back at him could be a Christopher.
Candi spun around on her chair and watched Michelle open a package of pantyhose. She had selected the nutmeg brown ten-denier Pretty Polly `tights'.
"You have to be careful with sheer pantyhose that you don't ladder or hole them. Some girls wear hosiery gloves but so long as you keep your fingernails and toenail manicured and treat the nylons carefully you will be ok," Michelle explained.
"Here. Roll up each leg and pull them on one leg at a time. When you have them up to your knees carefully ease them up the rest of the way and smooth them out and pull the gusset firm around your waist. You don't have a gaff but you will learn about that later. Tuck your penis and scrotum between your legs and the gusset will hold them in place for now so you don't have an unsightly bulge."
Candi blushed again when Michelle spoke about his genitals but she complied. She was amazed at how sensuous the nylons felt against her freshly shaved legs. When she had the pantyhose smoothed out and her `bits' tucked away she looked down and appraised her legs.
"Wow! I can see now why women wear these things! My legs look amazing and the feeling...I can't describe it!" Candi gushed.
"After a while it does tend to become a little mundane; but I still find it exciting slipping into sheer hosiery and I remember the very first time I tried on a pair of pantyhose and I envy how you feel right now," Michelle sipped at her scotch.
She handed Candi the black full cut satin panties and Candi slipped into them. Michelle watched the expression of delight on Candi's face as the satin caressed her nyloned thighs and buttocks.
"Oh my!" Candi sighed.
"Alright lets have a look," Michelle fussed around Candi, smoothing out any fine wrinkles in her hose and pulling her panties nice and tight.
Candi found herself becoming a little aroused and Michelle teased her by running a finger along Candi's crotch.
"You better not let that happen when you go in for your interview," she teased, gently squeezing Candi's tumescent penis.
"But seriously; if what you say is right and they only select five out every hundred applicants you better make sure your nylons are perfect. One snag, wrinkle or ladder could make the difference," Michelle said.
"Ok. Decision time. I see you have wisely selected a B cup bra. You do have little up top but not much. You can either purchase some breastforms or go with the `Twiggy' flat-chested look. It's up to you but before I got my breast augmentation I just went with what I had."
"Breastforms?" Candi looked puzzled.
"Plastic tits babe," Michelle grinned.
"Oh! Well most of the stewardesses I have seen have tended not to be big breasted; in fact I don't think the airlines like big-titted women. All the ads I've seen have been for `well-proportioned' women," Candi ruminated.
"Look honey; you have a svelte figure and killer legs that will look even better when we get you in heels so lets play to your advantages and forget about breastforms for now. If you look too flat-chested we can revisit that later," Michelle agreed.
Candi struggled a little putting on the brassiere, but with Michelle's help they adjusted the straps and got it to fit snugly. The cups were in fact padded a little and it didn't look bad at all. When they put on the cream satin blouse and tucked it into the skirt, it fitted perfectly.
"Who taught you to do that?" Michelle smiled as she watched Candi put her hand up her skirt and pull the blouse taut.
"That lady in the Op Shop," Candi smiled back.
"Well where would be without Op Shop ladies when we first started out crossdressing?" Michelle grinned.
"Ok. This will be the most difficult part for you; walking in high heels. You tell me you were once a very good dancer so hopefully it wont take us long to have you proficient. Just remember that when wearing high heels you need to put your toes down first then your heels. You will soon get the hang of it and as I said; I'm going to leave you with a practice regime."
Despite her poor performance at the Op Shop, once Michelle gave Candi some instruction she was soon strutting around the lounge in her high heels. She stumbled one or twice early on but after about twenty minutes Candi had the basics.
Candi was surprised at how comfortable and relaxed she was wearing ladies clothes and makeup and she also had to admit she was a little aroused. When Michelle was helping Candi get her balance early on; she was very close and occasionally put her arm around her for support and the close proximity of another gorgeous woman only served to heighten Candi's excitement.
Michelle sensed Candi's arousal in her presence and once Candi had the hang of standing on her own in her heels Michelle retired to an armchair after pouring herself another drink. She used Candi's phone to make a couple of phone calls and Candi politely moved to the other side of the room to give Michelle privacy.
I just called my hairdresser and made you an appointment for you tomorrow at three PM is that ok?"
Candi nodded and she wrote down the hairdresser's name and address.
"How can you be sure they will take me at three?" she asked.
"Hey! I'm Cherri Pops, famous ex rock and roll star. They'll do anything for me and I've made the booking in your name and explained the situation." she chuckled
"Also I've called my friend Stephanie Parker at Debenhams. Show up there as early as you can but well before your hairdresser's appointment. Stephanie will sort you out with some other clothes and accessories; you can't go out dressed like a nineteen sixties hostie. Take some makeup and you can transform there before you get your hair styled."
"You mean I'm going from Debenhams to the hairdresser dressed as a woman?" Candi was more than a little perturbed.
"Well you better get used to it and you might as well start as soon as you can. Ok. Let's put that jacket and on you have you pose in front of the full-length mirror for a while and we can call it quits," Michelle declared.
Candi was a little disappointed that dress-ups were about to be over. She was amazed at how much she liked seeing herself dressed this way and delighted at how wonderful the lingerie and clothing felt. Actually becoming `Candi' in her consciousness made her behave like a woman instinctively, or so she thought anyway.
Candi stood in front of the full-length mirror and appraised herself. She looked stunning. Her makeup was flawless and alluring, her hair framed her pretty face perfectly and the cut of the uniform enhanced her feminine figure. She had a small waist, well defined hips and just enough decolletage. Her legs were absolutely stunning. Encased in the sheer tan hose they were long, well defined and shapely. Michelle was right that wearing high heels would help shape her legs and they also lifted her pert bottom.
Michelle came and stood beside Candi and they looked at each other in the mirror.
"Two very gorgeous birds, wouldn't you say," Michelle whispered.
Candi became overwhelmed with emotion and a single tear ran down her cheek.
"I don't know how to thank you Michelle," she sighed.
"Their, their," Michelle hugged Candi and patted her back.
Candi rested her head Michelle's shoulders and lightly sobbed. Michelle pulled her closer.
Candi inhaled Michelle's perfume and then nuzzled her neck. Michelle sighed.
Then Michelle felt Candi's light kisses on her neck and gently lifted Candi's face away from her and looked in her pretty eyes.
"Ok babe. I was glad to help but now I..." Michelle's words were stifled when Candi pressed her lips against Michelle's.
Michelle tried to delicately ease Candi out of their embrace but Candi resisted and hugged Michelle harder.
Candi's tongue slid into Michelle's mouth and Michelle couldn't help but respond. The gorgeous woman she had created was tantalising her, tempting her.
Their satin blouses slid together, Michelle's bosom pressing against Candi's meagre breasts. Their bodies were so close that they were moulded together and the intensity of their kisses grew.
Michelle used all her strength to force Candi away from her held her at arm's length.
"Are you sure you want this? This is so new to you. I really think..." once again Candi fell on Michelle and pressed her tongue into Michelle's mouth.
Their thighs pushed together and they ground against each other.
Michelle surrendered.
The two stunning T Girls kissed and caressed one and other. Michelle skimmed her fingers along Candi's thigh and she gasped. Candi's first experience of having her limbs caressed whilst dressed enfemme was delightful; she tasted lipstick and inhaled perfume. This experience was so sensual and arousing; soft and delicate.
Michelle's hand slid further up Candi's thigh and she slowly dragged her fingertips across the front of Candi's panties and then searched for her penis which she found erect and leaking precum.
Candi had her hand under Michelle's skirt too and stroked her buttocks; the firm globes encased in slinky nylon panties.
Their kisses became more passionate and they gasped and huffed into each others mouths as their tongues explored each other's mouths.
Michelle could sense that Candi was a little perplexed as to how to proceed so she decided she would give Candi a treat. She dropped to her knees and lifted Candi's skirt and began to kiss the front of Candi's panties.
Candi squealed with lust and she placed her hands on Michelle's head, pressing it gently to her groin. Michelle was an experienced lover of trans women and knew how to excite Candi to full passion. She licked Candi's panties and explored between her legs with her tongue finding Candi's erect penis nestled in her groin; held in place by the gusset of her pantyhose and knickers.
Michelle teased Candi until she was close to screaming with desire and then she tore open the gusset of Candi's pantyhose with her teeth and used her fingers to free Candi's tumescent penis.
"Oh no...I'm coming!" the excitement and sensuality was too much for Candi.
Michelle just managed to guide Candi's engorged penis into her mouth as she ejaculated.
Michelle sucked and slavered at Candi's throbbing member; draining every scintilla of her sperm. Candi buckled at the knees and had to place her hands on to Michelle's shoulders to prevent herself from collapsing.
As Candi's orgasm subsided Michelle licked and kissed her erection until it began to deflate and then she tucked it away back inside Candi's panties. She pulled down Candi's skirt and arose.
They kissed again and Candi could taste her own secretions on Michelle's breath.
Candi began to awkwardly get to her knees. She was very unsure about performing fellatio but she expected that she should reciprocate. Michelle pulled Candi back to her feet.
"No. You don't have to do that," she kissed Candi gently on the lips.
"I want to," Candi replied but Michelle saw the doubt in her eyes.
"You don't want to; you think you have to. I enjoyed giving you pleasure; it doesn't always have to be recompensed. My pleasure was giving you pleasure," she grinned.
Now that she had orgasmed Candi felt a little awkward. Michelle sensed it and disengaged.
"Take off your skirt babe; if you get any semen on it and it dries you will never get it out. It's warm in here so you can sit in your knickers and blouse and we can talk. I still have things that you need to know."
Michelle poured them both a drink and lit them both a cigarette while Candi slipped off her heels, took off her jacket, unzipped her skirt and smoothed them carefully before laying them down on a chair.
Michelle sat in one corner of the lounge giving Candi space in case she felt embarrassed or uncomfortable. She was delighted when Candi sat next to her and snuggled up to her. Michelle handed Candi her drink and cigarette and they chatted long into the evening. They occasionally kissed and continually stroked and caressed each other.
Michelle left in the early hours after a long kiss goodnight.
"I'm not sure if I can do this again. I will help you any way I can but the last thing I need right now is a complicated relationship and the temptation is there believe me," Michelle said as she put on her coat.
Candi felt flattered that such a beautiful creature as Michelle should say such a thing and went to bed contented. She slipped off her blouse and slid under the sheets still dressed in her pantyhose, bra and knickers. They felt so nice that she didn't want to take them off. She didn't even remove her makeup.
She awoke late the next day with the sun streaming in through the window. For a few seconds she thought she had dreamt the whole thing. She noticed her pillow was stained with lipstick, mascara and eyeshadow and she smiled. She could still taste Michelle's sweet mouth on hers.
She rolled over and tried to catch more sleep but her mind was racing. She had so much to do!
To be continued...
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Michele Nylons
michelenylons@msn.com