Hostess with the Mostest Ch. 01

"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.