My Initiation


Chapter 1

She was ambling slowly through the mall gazing in shop windows. A stunningly beautiful brunette wearing dark stockings over long shapely legs, a white cotton blouse decorated with delicate embroidery and a beige skirt that seemed to hug the hips then flair out at the knees. Unable to help myself, I stared openly at her legs beneath the skirt, the shape of her gorgeous body, letting my eyes roam up to her small, but perfect breasts, and up to her beautiful face. And there I lingered drinking in the beauty.

I'm a face person. There are leg men, breast men and bottom men but I look at the face. A beautiful face always attracts me first. Especially the eyes. And she had eyes that caused the pulse to leap and the heart to flutter. Dark and sultry. Come to bed eyes. Somehow, I thought she looked familiar. Hadn't I seen her somewhere before?

She must have felt my gaze on her, because she stopped and looked right at me. Those beautiful eyes opened wide and her hand flew up to her mouth, the colour draining from her face. She turned on her heel and almost ran out of the mall doors. I caught sight, with a small thrill, the flash of white lace below her skirt and thought I saw the distinct outline of a thong through the thin material of her skirt as she disappeared. I took a deep breath. Did I know her? I didn't think so but I'd certainly seen her somewhere before. Strange reaction too. Perhaps it was someone else she had seen. I looked around and mentally shrugged then continued my window shopping trip.

I was sitting in my office on Monday morning when there was a knock on the door and Mike Davis poked his head in.

"Steve, got a minute?" he said.

"Sure Mike, come on in" I replied. He worked in another department but I'd seen him around the corridors. We were only really on nodding terms. He stepped in and slowly walked over to my desk.

I looked at him closely. He looked awful.

"Hey Mike" I said "What's up. You look terrible"

He sat down opposite and looked into his lap. "It's about Saturday," he mumbled.

I searched my memory for what he could be talking about.

"Saturday? What happened Saturday? I said. Had someone in his family died? Been robbed? House burned down?

"In the mall - Saturday morning. When you saw me." he said as he looked up.

I was sure I hadn't seen him but while pondering this he said "You were looking right at me."

"Mike I don't know wh ..." I started

"I just wanted to ask you not to say anything to anyone. I'd be finished here if it got out. Everybody would laugh" he said.

"Mike, what are you talking about?" Then it hit me. The girl with the beautiful eyes. That familar face.

"That was y..?"

"You know it was. You were staring at me with your mouth open" he exclaimed "Why do you think I ran?"

He looked thoroughly miserable. His fingers were screwing the end of his tie into a ball.

"Mike, I never realised it was you." I said "I just was admiring a good looking girl. I always stare at good looking girls." Pausing, I said "You mean you dress up"

"Yes!" he said "Don't piss me about Mike. You knew it was me."

I looked at him.. Yes it was. The eyes of course. That's how I'd thought I recognised him. I smiled.

"Mike." I said calm down. Have a coffee" I got up and went to my coffee machine, my mind in a whirl. How could this wreck of a man sitting in my office chair be that wonderful girl in the Mall?

I took his coffee over to him and sat on the desk facing him.

"First" I said "I have no intention telling anyone. That's not my style. Second, I thought I recognised your face but dismissed it as a mistake. Third, I thought I was looking at a beautiful girl, so I stared. Was that really you?... Wow" I smiled.

He looked at me, searching my face for the truth

"You're not kidding are you?" he pleaded "

"Scout's honour" I said saluting him "If you hadn't come in here confessing, I wouldn't have made the connection. You would have fooled anyone."

"I didn't go out to fool anyone" he said

"Sorry" I said "Perhaps enchanted would be a better word." I smiled

He looked a lot better now. The colour was returning to his cheeks. He smiled back.

"It was my first time out of the house y'know" he said "I've always been too scared to venture out dressed... in.. you know"

There was an awkward silence while I searched for a line. The guy was clearly upset.

"How long have you been err.. dressing in.. err" I said lamely. He hesitated, perhaps wondering if he could trust me.

"Ever since I was young. "he said quietly. "I've always had a 'thing' about women's clothing" he sighed "but I've only been fully dressing for about 6 months. I've always kept in my house but on Saturday I really wanted to go out. To see if I could look like a real woman"

"Well Mike.. You certainly succeeded. You looked one hundred percent woman to me." I said. It wasn't a lie. I had thought I was looking at a stunning girl. Somehow, the idea now disturbed me, but in an mildly erotic way.

The change was miraculous. He seemed to grow in his chair. The worry lines faded and he grinned back at me.

"You're not kidding are you. I was so worried that I would come in today hearing lewd comments and people giggling. The idiots in my department are always talking about somebody and I thought if it got out.."

"I wouldn't do that Mike" I said seriously "I'm not like that."

My own life wasn't too squeaky clean since my wife had left me - Internet porn, late night chat rooms, cybersex etc. loneliness and a lack of sexual satisfaction can do funny things so who was I to criticise? And to be honest, I was fascinated by he thought of a man dressing in female clothing. I had always found women more attractive in clothing than out of it. When you've seen one shaved twat you've seen 'em all and breasts were usually the same shape. But a girl dressed in really expensive clothing – and especially underwear was, for me, a real delight.

"Thanks Steve" he said gratefully "Anything I can do for you..."

"Nonsense pal." I said "But I'd check my fingernails before coming into work if I were you." I looked at his hands

He looked down and saw a speck of red nail varnish on his little finger. We both laughed and he got up and went to the door, scratching at the red mark.

"Thanks for being so understanding. I feel a lot better now." he said

"Don't mention it" I said "Oh and Mike" he paused looking at me warily, "You really were stunningly beautiful"

He blushed and grinned but at the same time gave me a curious look . And disappeared closing the door.

Chapter 2

I saw a fair bit of Mike over the next few weeks. We'd stop and chat in the corridors, he'd pop into the office for a coffee occasionally and although he was in a different department, always seemed to be around. I liked this. He was a good laugh but I never forgot that beautiful girl with the 'knock-out' eyes.

One Friday night he popped his head into my door and said "There's a few of us going to the pub after work. Wanna come?"

I thought it over. I hadn't been out for three years and I suppose I was stuck in a bit of a social rut. Socialising wasn't my way of enjoying myself anymore. "No thanks Mike. I got loads to d..."

"Oh please Steve. I'd really like your company. Most of them are real pratts and I need a mate." He looked desperate and he called me a 'mate'. I was touched. I had no 'mates'. No friends at all really and if he considered me a 'mate' then a mate I would like to be.

I laughed "OK then but only for an hour"

"Great" he said, his face breaking into a grin "See you at five." and slammed the door.

He was right. They were pratts. Wannabe yuppies. Telling tales about their workmates.. 'so and so was dating'.. 'somebody in purchase was purported to be gay' - the head of sales was shagging the general manager's wife... All they could talk about were other people's secrets. It was all complete bollocks.

Mike looked at me, his eyebrows raised and murmured quietly, "You see what would have happened if they'd found out? I'd have been crucified."

I nodded. "You work with this lot?" I murmured "They're morons"

"I know" he said out of the corner of his mouth. "I get this all day. That's why you're here. Moral support." He grinned.

"No-one's spoken to me yet" I protested.

"Count yourself lucky." he laughed. "Join in if you want"

I smiled at the challenge and thought about it for a few minutes 'OK' I thought 'go for it!'

"You know Shirley in asset maintenance control is a lesbian" I said loudly. The group were shocked into silence.

"She's been seen with several women." I said. "Been taking them home for weekends. I understand she likes.." I whispered "leather and warm custard"

I had them. They were riveted and the silence was complete. A thin gawky girl put her hand to her mouth and looked horrified but excited. "Really" she exclaimed breathlessly. "What does she do with the custard?"

I cupped my hand round my mouth and whispered "Goes inside the leather. Feels wonderful I'm told. Instant orgasm. Try it"

They broke into frenzied chatter, "I wouldn't have thought it"... "Is she the blonde" ... "She seemed a nice girl"... "Custard?".. and so on.

"Who's Shirley and where the hell is asset maintenance control?" said Mike, an amused look on his face.

"Dunno" I said "just made it up."

I think it was one of those moments that cements a friendship. We laughed till our sides were aching. Tears rolled down our cheeks and the pain in the diaphragm lasted into the next day.

"That's why I asked you to come" he spluttered "You saved my life tonight" He slowly stopped smiling "It's getting to be a habit " he said softly.

I looked into his eyes and saw the girl again.

"Aww knock it off" I said "haven't had so much fun for years"

"How many years?" he asked quietly.

"Come on" I said and grabbing my glass headed for the bar. We found a couple of stools at a quiet end of the bar and ordered another drink.

"Lots of years" I grimaced and took a sip.

"That sounds like a long story" he said quietly.

"Not really" I said "Wife left. Stopped going out. Got into a rut. My entertainment is the internet and .." I thought for a moment. "The internet I suppose. The more seedy side." I confessed.

As the evening progressed our voices had tuned down to 'very soft' and as far as I was concerned, there were only the two of us in the bar. The 'Yuppie morons' sounded like distant seagulls chasing a fishing boat. To me, they ceased to exist! I told him of my sour marriage and my loneliness. I thought Mike was lonely with his 'hobby'.. I felt I could talk to him. He had shared a secret with me and I felt safe pouring my heart out to him. He told me of his childhood. How he was an only child brought up by his mother, how he could never talk to girls. The tangled tongue syndrome! "I'm not gay" he said. "I like looking at women as much as any man but my brain refuses to control my tongue." Perhaps that's why I.."

"Shhh" I said as one of the spotty youths came over. All the others ad left and he looked as if he wanted to join us.

"Isn't it your bedtime? Mum will be worrying" I said coldly

He looked at his enormous sports watch hanging loosely on his skinny wrist. "Oh err... It's time I was going. Bye. See you Monday" And almost ran out of the bar.

Mike broke into hysterics. "Oh bastard. " He said "he was one of the better ones."

"Tell him he's in bad company" I laughed.

I looked at my own watch. Ten O'clock. Mike and I had been quietly chatting for 4 hours. I couldn't believe it. However the quiet mood had been broken.

We stayed another hour just talking men things. It turned out we shared a love of music, books, wildlife, scenery.. a hatred of politics, football and in that hour, we - sort of - laid down a trusting friendship. We went for a curry afterwards and when I finally got home I felt as if a breath of fresh air had blown through my life. I had been out, made a friend and thoroughly enjoyed myself.

We met quite often after that. We'd go out for a few drinks and stop off for a late night meal and usually end up at one of our houses for a nightcap. He was, now, totally unashamed of his cross-dressing and we discussed it a lot. He tried to explain what he got out of it.

"I always felt I should have been born a girl. It's the feeling of being beautiful" he explained one night. "At first it was just feel of the clothes.. the softness of female lingerie against my body that excited me but as time went on and I experimented with wigs and makeup, I realised I could look nice as a woman."

I thought nice was a bit of an understatement. The girl I'd seen had been nothing short of stunning.

"I spent months getting the right makeup for my skin tone. I search loads of sights on the internet for cosmetics and read all I could on how to do it. The clothes were easy." He shrugged "I know what I like to see a woman wearing and just tried to match my figure to that."

"Ah the dreaded Internet" I said "You either love it or hate it but it'll find whatever you want."

"Did you find that you wanted on the internet?" he asked seriously. I looked and felt uncomfortable.

"An attempt at relief from loneliness I suppose, which didn't work. Some sexual release – in the form of porn sites... Sex chat rooms, that sort of thing. God but here are some really strange people on there. I think I was becoming one of them too. Do you know I sometimes went on pretending to be a woman just for cyber. So you may be saving me too" I said seriously.

I didn't mention that my surfing, since we had become friends, had included Transvestite and Transformation sites. Most of the exhibits I had seen – the so called 'chicks with dicks' looked obnoxious to me. Huge oversized breasts, thick plaster makeup, and dicks to frighten a donkey. Their clothing was always garish, extravagant, pretend lingerie. Usually a tight Basque in red and black or lime green and orange and they always looked so fierce! Often, they had their dick up another's ass and both were smiling at the camera, as if in ecstasy.

There had also been the 'real' transsexuals. Men who felt as Mike had been talking about. Who didn't dress for sex but for a change. Who had feminine feelings and needed to express them. I never saw any as physically attractive as Mike had been though.

Secretly, I wanted to see the girl again. Somehow I couldn't ask Mike to dress up for me. Mike was a mate and I wanted to keep it that way. I was also worried he might take it the wrong way and think I wanted to see a freak show. I could see that girl every night in Mike's eyes. It was slowly driving me bonkers.

Chapter 3

So I devised a plan. I booked a table at a posh Italian restaurant in a nearby town. One where we wouldn't be known. I didn't think he'd want to be seen locally. Then I rang Mike one Saturday morning.

"Hi Mike, It's Steve" I said when he picked up the phone.

"Morning mate" he said. We'd only parted in the small hours of the previous night and he sounded sleepy.

"Look Mike. I need a favour." I began hesitantly.

"Sure, what can I do for you?"

"It's about Michelle. I've been wanting to take her out for ages and I've booked a table at the Valle Dora in Ludley tonight." I said with a rush. "And I'd really like to take Michelle out for dinner but I'm a bit shy." My words were tumbling out now, "Can you ask her for me?"

There was silence on the end of the phone.

"Mike? You there? " I asked.

"You want to take err.. Michelle out for dinner?" he said hesitantly.

"Yeah – that's right. It's a lovely restaurant and I wondered if you could ask her for me. I've been wanting to take her out for ages" I was repeating myself now and babbling. Beads of sweat stood out on my brow. My hands were shaking. How would Mike take this?

"I'd ask her myself but err.. well I never see her." I babbled. Then Mike caught on.

"You sure Steve?" he asked

"Yeah err – I've booked a table and err.. please ask her Mike" I pleaded.

"I'm certain she'd be delighted" Mike replied. There was worry in his voice.

"Ah that's great – Thanks Mike – Tell her I'll pick her up at eight. Bye."

I slammed down the phone before my nerve broke and sat on the sofa.

"Wow" I said and grinned to myself.

OK, I had all day to get myself ready. I felt like a kid on his first date. First I went to buy some new clothes. The lot. I hadn't bought anything for myself since my wife left. All my clothes all had that 'lived in' look. Then a haircut. By seven I was feeling and looking pretty snappy. An hour to go. I paced nervously. Would Mike be on the doorstep or Michelle, the name I had christened her. I'd be disappointed if Mike appeared. As much as I liked him, I wanted to see the girl again. That fleeting glimpse of Michelle had completely captivated me.

I needn't have worried. When the door opened, Michelle stood wearing a stunning pale blue Chiffon layered dress. I was unable to breathe. She looked even more beautiful close up, dark, long hair, small gold earrings and a matching necklace. She looked a bit nervous, I thought as she stood with her hands clasped in front of her.

I must have been gaping with my mouth open because she smiled and said "Don't you know it's rude to stare Steve?"

"I – I'm sorry" I stammered "You're even more beautiful than I remembered." And she was. The dress showed her figure to its best and the dark coloured stockings revealed long, shapely legs. This wasn't a man! It was a beautiful woman. I was speechless.

She blushed and looked down.

"Really" I said you're a knockout"

We drove to the restaurant and at no time did I feel as though I was here with a man dressed as a woman. She was completely feminine, sexy and self assured. The conversation was a bit awkward at first but soon warmed up and I found that it became easy to chat to her about a range of subjects. The conversation was completely different to the talks Mike and I had engaged in. Mike never entered my head the entire evening.

Afterwards I drove her home and she asked me in for a coffee. It was an odd feeling. This house I'd been to so many times with Mike and now I was here with Michelle. All trace of Mike had gone though. There was a delicious smell of perfume, the lights were low and she put some soft jazz on I'd never heard before. We sat on the sofa and sipped our coffee.

"Thank you for a lovely meal" she said "I haven't been out before in the evenings." She hesitated. "Why did you ask me?"

"I've wanted to meet you ever since I saw you in the mall." I replied shyly

"But you know what I am don't you?" She said an amused look on her face, head cocked to one side.

"Of course" I said "I also know you are extremely beautiful, good company and very, very feminine"

She smiled blushing again.

"And you don't find that strange?" she said "Let me put it this way. I am a man dressed as a woman. Here, I live as a woman and at work, I live as a man. Doesn't that worry you".

I felt I was being tested. I thought a few moments. "No. "I said. "At work you are Mike, my friend. "Here, you are Michelle, A beautiful woman. Here, You don't behave like Mike, you don't look like Mike and you are a girl I have wanted to meet since I saw you. She blushed again.

It was late when I left her house with a promise of another evening out the following Friday. That night, I pondered over our date. I knew it was Mike dressed up yet I also knew it wasn't. Her whole manner was different. There were no jokes, moments of loud laughter girl watching. At her house, the music and atmosphere was different. I was in a girl's house. I looked forward to our next meeting and for some reason was sorry that I might not go out with Mike again. "I hope he doesn't mind too much" I said to myself with a laugh.

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