Emma's First Day

by Sarah Smith

 

Simon was a real geek. He sat in front of his computer all day, didn't work, lived with his divorced mum, Helen, and the nearest he got to sex was from staring at his collection of lingerie catalogues. His mother had had enough and one day she came home from work with good news.

"I've found you a job" she announced. He was so surprised that he looked up from his computer.

"Oh, great!" was his sarcastic reply.

"You have to strike out on your own sometime young man. Right now you are a waste of space, a poor excuse for a son".

"I knew you always wanted a girl" sneered the boy.

"Funny thing is you're right, and the even funnier thing is that the job I got you is for a girl so I told them you were a girl and if you have a problem then you can leave my house right now." His mother snapped right back and then stood back to watch the effect. He was shocked but quickly recovered and then continued with his game.

She lent over to him "Oh, come on, I've seen your catalogues, I bet sometimes you wonder what it must be like to be in those lovely clothes"

He was blushing.

"Come on, just a bit of fun, why not humour me? You know you've got lovely smooth skin, delicate features, a slim build and nice hair. You could make a lovely girl"

He was glowing red now. Angry as well that she had seen through him and know thoughts so deep that he hardly knew them, and when they surfaced he would bury them again. But, they always came back.

She smiled "I'll run you a bath and get things ready"

 

Simon carefully ran the razor along his slim legs, now they were completely free of hair they felt smooth, soft and sensual and he couldn't resist running his hands along them. He also shaved under his arms as his mother instructed. After the long scented bath he was ready to have his hair done. He brushed the thick chestnut hair and then sat in a chair while Helen got to work styling it into a more feminine shape by blow drying it and adding some hair clips. Neither of them could believe how easily he had been persuaded to do this but they chatted away in a way that they had not done in years.

Helen took her time making him up, it was their first time but they had to get it exactly right and as they were similar looking Helen knew how to compliment his dark eyes and pale complexion.

"How am I doing?" he asked fluttering his long eyelashes.

"You are starting to look great" replied Helen not exaggerating. His fine features now made up so beautifully that he was a very pretty girl indeed.

"I think we should call you Emma" Helen decided.

"Emma's a nice name" he agreed.

 

When the make up was done Emma was led to Helen's room where the clothes were laid out for him. On the bed was a grey business suit, a white blouse and some underwear. Helen helped him removed his dressing gown and handed him the white panties which he slipped on quickly. Next she fastened the bra for him and inserted the false cups giving him small breasts. She rolled up the tights into small circles and handed them to him, quite naturally he stepped a toe into one leg and pulled the sheer denier hose up his smooth leg. The feeling was electric, he sighed as the fine nylon mesh encased his shapely legs as he rolled them to the tops of his thighs and over his bottom. He ran his hands over them again to smooth them out and then admired how long and sexy they looked in sheer flesh toned nylon. The suit was obviously for work but he could not wait to try it. First came a silk slip and then the skirt, it came to a couple of inches above his knees but had a sexy split in the thigh. He walked up and down enjoying the feeling and then put on the blouse and jacket. The jacket was tight around the waist and short. Then he slipped in the black court shoes with a two inch heel and tried walking, at first it was tricky but he would soon get the hang of it. Helen admired Emma, her pretty transvestite son, as he paraded in front of her looking like the daughter she had always wanted. Emma stopped and faced his mother, one leg to the side showing a long shapely leg, they smiled at each other.

"Oh, my pretty little girl" she sighed "ready for work and every inch the office girl".

Emma continued to admire his new self. "You've made me look gorgeous, I love it and I feel great. Can I stay like this?"

"Maybe you should change from your work clothes to save them. You can borrow some of my things."

 

Helen and Emma sat up until late talking like mother and daughter over glasses of wine. Emma borrowed a short black pleated skirt showing off her gorgeous long legs and occasionally paused to stroke the smooth nylon and feel its comforting caress. The tight sweater she borrowed showed off her pert breasts. As the two women talked into the night neither felt strange in their new situation and they talked about the how Emma felt in her new role and what it might bring them. Despite this being his first time as a girl Emma was completely at ease and natural and was looking forward to the future for once.

 

They had arranged to go shopping the next day. As this was new to her daughter Helen had assumed that he would go as Simon and pick out things to try later on that day, however Emma surprised her by wearing the same clothes as the night before. She had thought that he might want to be eased into it but obviously Emma had other ideas. One thing she noticed was that Emma was now wearing black opaque tights but where did they come from?

"I bought them in the little shop across the road" was the answer

"You've been out as Emma?!"

"I couldn't wait, and I thought you said I looked totally like a girl"

"Yes, but this is so quick" said Helen.

"The thing is this. As soon as I saw myself and as soon as I felt the clothes on me I just felt right, and for the first time I felt confident about myself".

"OK, but let's take things one step at a time from now on, get back into her old clothes and we'll go shopping".

With that Emma flounced off to his room and reluctantly got undressed.

 

They got back several hours later. It had been a difficult trip as Simon had been his usual sulky miserable wretched self, nothing like the charming young girl from a few hours before. Helen realised that she had unleashed something that neither of them would be able to control, Emma was more than just a part time hobby. They argued all the way home. Simon accused his mother of making him a transvestite and that he did not want any part of it any more. However, when they got home he changed his attitude. Maybe it was the prospect of the all the clothes, cosmetics and accessories he now had to try. This time Helen showed him how to apply the make up himself and he did very well, resisting the temptation to go overboard. This evening Emma chose her new black dress, every woman needs one little black dress advised her mother. It was a tight lycra with sleeves and short. Emma knew she had great legs now and wanted them to be on display. As he admired himself in the mirror he ran his hands along those endless legs in very sheer fine black nylon, starting at the slim ankle and slowly enjoying the caress along his taught calves and to his shapely thighs. Emma indulged in a deep red lip gloss and was impressed with his new sexy look. He then moved to the dining room to join his mother for dinner feeling all the more sexy as his sheer thighs wisped together as he walked.

 

"You seem even more feminine today" said Helen "last night I felt like I was talking to a girl but today you seem even more girly. I can't believe I have such a beautiful girl".

Emma blew her a kiss "Thanks mum. It's thanks to you that I am able to do this. The thing is that I feel different, not Simon in a dress".

"You are a different person; you seem so much at ease as Emma. I do see a very lovely girl and I know we will have great fun together".

Helen then hugged the beautiful young transvestite. "Oh, my gorgeous girl, if only we'd done this years ago".

The tall girl hugged her mother "well we've done it now that's the main thing, hang on…".

He suddenly noticed that there were two extra places at the table.

"Oh, yes" started Helen "I invited Cathy, and her friend Isabel, for dinner. It's important that you start interacting with other people as you start work on Monday"

Emma felt a wave of panic and the colour drained from his made up face, he lost all his confidence and sensuality. He started to feel like a stupid tranny boy in a dress.

"Relax" assured Helen, seeing his discomfort "Cathy and Isabel already know, Cathy helped me buy your first things and Isabel is who you'll be working for".

"I didn't know anyone else knew about this" snapped Emma "I might not be ready".

"Cathy is my sister and Isabel is her partner, that's why they know. Besides, I decide when you are ready, not you" the she added reassuringly "look how far you've come in 24 hours. They are dying to meet you".

Emma slid into a high stool by the table and crossed her long legs. The wisp of the sheer black tights reminded him of his feminine attire and he stroked his knee and thigh taking confidence from his look. As if by automatic reflex he started checking his make up, he thought about applying more kohl but decided to leave it for now and just look at his pretty face. "It won't be too bad". He thought. Things had been great with his mother since yesterday. They had been like mother and daughter, now he and Cathy might be like aunt and niece. Cathy didn't really like men that much so it could only improve things. Putting away the compact he stood up and smoothed the black dress over his hips and then adjusted his breast forms. What Cathy's new girlfriend would make of her transvestite niece was another matter. Emma heard high heeled footsteps and then the doorbell rang. Now she would find out.

 

"Why don't you get that?" called Helen but Emma was already on his way. Confidently walking in high heels and moving his hips as he did. He opened the door to his aunt and her lover. Both were very feminine and dressed elegantly, they both scanned their eyes over Emma in his tight black dress and perfectly made up face. They came into the hall and they exchanged kisses.

"So, this is my lovely young niece?" cooed Cathy "such an improvement. You are stunning".

"And my new office girl" joined in Isabel "I hope you won't be looking this sexy at work or we'll never get any work done"

Emma blushed, all his worries were for nothing. They handed him a present.

"We couldn't resist it" Cathy said as Emma open that bag and took out a beautiful negligee. It was a deep port colour and Emma held up against him.

"I can't wait to try it on" he sighed.

As they went through to the kitchen he overheard Isabel whisper "Fantastic legs, just like her aunt".

Over a lovely dinner the four women sat and talked about how Emma was going to cope in his new role.

"It's true that you look gorgeous as a girl" began Cathy "and you are a useless lot as a boy so I think you are stronger, more confident and sexier as Emma. Why would you want to go back?"

"I'm not sure I could even if I wanted to" said Emma "this has been a revelation and I am enjoying every moment that comes."

Isabel lent towards Emma, giving him a saucy smile and putting a hand on his knee "I hope this isn't too personal but do you like boys or girls? You are going to get lots of attention you know?"

Emma blushed a deep red and shifted uncomfortably.

Helen took Emma's hand and smiled "Whatever my girl chooses will be fine with me, if she wants to go out with girls, boys, or both then that's great".

 

Later that evening while in bed Emma wore his new negligee and French knickers, the sensuous feel of the silky material was feminine and arousing. He thought about how the other women had referred to Emma as a girl all evening. That was fine because that was how he felt, from now on he was she.

It was Isabel's question about her sexuality that was most arousing. Simon had been an asexual sort of boy, but Emma was a passionate sexually aware attractive woman and she would have a sex life. She slid her hands down her body feeling the silky material over her hot skin, the hands continued down under the elastic of the knickers. She let her mind wander through various images. A lean muscular man, his hard kiss and firm grip, and then his penetration. A beautiful girl with a curvy figure and sexy soft lips, a lipstick lesbian. A sexy t girl just like Emma, beautiful, glamorous, but with something extra.

She would soon find out.

  

 

 

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