My Initiation

"Good night" she said saucily and headed to her bedroom.

I closed the door behind me and sat in front of the vanity unit. I felt and looked wonderful in these clothes. I lowered the dress from my shoulders and traced the outline of my breasts through the camisole. Standing up, I let the dress slip to the floor and lowered the slip. Standing in just the underwear was so exciting. I didn't look odd at all. I stroked myself through the flimsy material of the panties, instantly reviving my erection and only force of will made me stop before I climaxed into the clothing. I was determined not to masturbate here. Maybe at home, but somehow it felt all wrong in Michelle's house.

I undressed and folded all the clothes before going into the en-suite bathroom to wash the makeup off. She had left a long black nightgown on the pillow but I was frustrated enough so after a quick examination, I put it on the other pillow and climbed into bed. I lay awake tossing and turning and still feeling the stockings, panties and slip against my body.

I finally got to sleep just as it was starting to get light. And therefore, felt awful the next day. I climbed out of bed and headed for the shower, glancing longingly at the pile of frothy lingerie stacked on the chair. I dressed in my own clothes and went to the kitchen where Michelle was pouring coffee.

"Good morning. Did you sleep well?" she asked with a smile although I detected a hint of disappointment briefly in her eyes.

"Morning" I said "not too good. Strange bed"

"Ah" she nodded knowingly "Coffee?"

I took the cup and sipped looking at the table.

"Not feeling to bright this morning? She enquired

I smiled "No I feel fine – honest" Which is another way of saying 'I don't feel fine'.

"You're not having a 'morning after' guilt trip are you she said with a laugh.

I looked up and smiled sheepishly "You could say that."

"Steve, no-one will ever know but you and me and last night was nothing to be ashamed about."

"Oh please... no!" I said "It's nothing like that. I know you wouldn't tell and I'm not ashamed. Anything but. I loved it. I adored wearing those clothes. I couldn't sleep because I wanted to be in those clothes. That's the problem."

"Problem?. Where's the problem?" she asked. "You can wear them any time you want."

"This is a big change for me" I said "I never realised I was 'into' cross dressing. My mind tells me I want to but my brain says it's wrong. Sorry, love, I'm not explaining this very well"

Well don't worry about it "she said softly "It's only a bit of fun. Now where are you taking me to lunch?"

I laughed. "Somewhere in the country. Nice and quiet with a log fire."

"It's mid summer!" she said"

"Well it wont be lit" I said and smacked her bum as she passed to get changed.

She was stunning – this girl. I found I was growing extremely fond of her.

Sunday passed with a quiet lunch and a walk beside a river and Michelle kept me charmed with her girlish chat and striking looks. That dark cloud was always in my mind, however. Part of me wanted to rush back and bury myself in underwear and part said I should take this weekend as a demonstration of fancy dress.

She must have sensed my mood. As we parted that evening she said" Steve, Don't ponder over this too much. It's not worth making yourself ill. You'll do the right thing in the end."

I smiled "Thanks Michelle for a wonderful weekend. I have a lot of thinking to do but whatever decision I come up with, I'd still like to take you out."

"And so you may" she said "And thank you"

Chapter 6

I managed little sleep again that night and Monday morning was starting to look a bit jaded.

"Morning Steve." said a cheerful voice in the doorway." Mike came in and closed the door.

"Hi Mike. " I said " Good weekend?"

"Wonderful" He said as he sat down "Met this really gorgeous girl. A real knock-out"

I looked up sharply and saw he was grinning. So the game starts I thought.

"Really?" You seeing her again?"

"Hmm – don't know yet. Hope so though. Wonderful girl."

"Good for you " I said smiling

"You look a bit peaky though" He peered at my darkish eyes "looks like you got a problem. Take my grandmother's advice. 'If tree too large for elephant to scratch... Place lemon grass on wound"

I laughed "What hell does that mean?"

"Dunno... she was bonkers, absolutely barking." He stood up and left for the door. "Seriously Steve, Don't lose any more sleep. It'll sort itself out. See you later" And left.

I thought about Mike's reaction. 'Met a wonderful girl? Hoped to see her again? So all Mike wanted was a girlfriend of his own. Me. I was flattered in a way. But I still wasn't convinced. I took his advice and buried myself in my work. Each time my mind drifted to Saturday night I refused to dwell on it and instead, worked harder.

It was Thursday morning before I came to a decision. My life as a man was dull. A failed marriage, no contact with girls, a thoroughly boring job, and before Mike came along, long lonely evenings on the internet – the World, Wide Wank. Michelle had made me see a new possibility. Living as a woman. I enjoyed it. In fact I lusted after the feelings. And I was falling for Michelle. The 'gay' question kept rearing it's head but I put it down... She looks like a woman, she acts like a woman, and apart from a couple of items in a different place, she is a woman. I thought perhaps she looked on me the same. I hoped so because I was going to go for it. I wanted to dress and learn how to be feminine. I'd enjoyed feeling beautiful.

Mike popped in, as usual at tea break and threw a donut on the desk.

"So you seeing this wonderful girl this weekend" I asked innocently

"Not sure yet." He said through a mouthful of dough and sugar.

"Perhaps you should check your stars" I said and picked up the newspaper. "When's your birthday?"

"August 30th. I'm a Virgo" he said "Story of my life"

"OK – I got it...With the conjunction of Mars and Uranus, A final decision has been made. 'A turning point has been reached and passed. Your hopes will be fulfilled. A weekend of happiness will follow.' There you go Mike. Looking good."

He looked at me with wide eyes and a mouthful of donut.

"Really? " he said after swallowing "Great err... wow."

I laughed and said "Of course, you can't believe in all his astrology shit. It's all made up" I was having fun now, I had made it up.

That night I rang Michelle. "Look err... I've got a free weekend, a couple of steaks and some wine. I wondered if we could err ... carry on where we left off last Saturday"

"Of course" she said gaily. "I was hoping you would." She sounded as excited as I felt.

That night I gave myself a whole body hair removal treatment. I had fair hair so not much showed but I thought I would be better if I got rid of it all. In bed, even my sheets felt sexy. I hadn't realised how much feeling was numbed by body hair. On Friday I went out for the steaks and some wine and nipped into a jewellers for the gift I'd seen earlier. I went home from work, showered dressed and packed a few oddments for the weekend.

The door almost flew open as I knocked. "Come in Steve" she said smiling sexily. I'm glad you're early." She looked like an excited teenager "Are you sure you want to do this?"

"Definitely" I replied. "I've been thinking about it all week and now, I can't wait." I handed her the bags of steaks and wine and followed her into the kitchen.

She poured two glasses of wine and led me into her bedroom. She opened some drawers and I started to undress.

"Can you manage or do you want some help" she said with an smile.

"I need help. I don't know what to choose or even what to put on first "

She laughed "OK, lets start with some stockings. Stay-ups I think. Much nicer "

She handed me a pair of dark stockings with a wide lace top. I pulled them on. She was right. The plastic strip round the top glued itself to my thigh, feeling delicious.

"These are lovely if you want to try them" she said handing me a bra and matching panties. I almost groaned at the sight of them. They were the palest blue with peach coloured embroidery flowers. The panties turned out to be a thong, much to my delight, and the bra was light and lacy. The breast forms were again inserted into the cups and my figure took on shape. The mirrors were on view this time and I found no shame admiring my body in underwear.

"You can have the full slip tonight. I bought another" she said handing me the filmy garment. It had the thinnest of straps and lace round the breasts and hem. And it felt wonderful. I watched in the mirror as she applied the makeup, trying to see how she did it. "I'll show you how to do this tomorrow so you can do it yourself" she murmured concentrating on the eye shadow.

She finished and drew out the blonde wig, fitting it and flicking back a few stray hairs. She stood back and smiled. "Wow. We've done it again. Still beautiful."

I looked in the mirror and had to agree. "Thank you Michelle" I said. "I even feel sexy now. " I laughed and stood up. "What shall I wear tonight"

She went to the wardrobe and took out an appealing sleeveless, v-neck dress in pale blue with pink roses and green vines. It was multilayered and filmy and I loved it. It hugged my breasts and waist then flared out, seeming to have a life of it's own. "I love that dress" said Michelle "It's so summery.

"Are you sure you don't mind me borrowing these?" I asked. She placed her hands on my hips.

"Of course I don't. I'm loving this as much as you appear to be doing." She lowered her eyes. "I've longed to share these with you. To be able to share myself with you. I was so happy when you told me you wanted to carry on."

I almost lost it and kissed her then. She looked so beautiful in a grey skirt and dusky pink blouse – the lace from a camisole just peeking above her breasts. Tomorrow we can explore the rest of my wardrobe." She said and took my hand. "Come on lets do something with those steaks."

"Michelle" I said. "I've got this for you." I took the small box out of my cast-off trouser pocket and handed it to her. It's a little thank you." She looked surprised and opened it. Inside was a gold chain with an small Ankh hanging from it.

"It means 'Life' "I said. "Thank you for a new life"

I took it from her limp fingers and fastened it round her neck.

"It's beautiful" she said "Thank you so much. I shall wear it always."

She hugged me and kissed my cheek. I thought I saw a tear as she pulled away.

It was a dream evening. After the meal we sat close on the sofa and just admired each other. We discussed clothing and underwear and what we liked. We talked about makeup. How to determine the colours for a particular skin tone. I was in ecstasy. The clothing against my skin was haunting me with avert slight movement and the thong was playing a large part.

Eventually, after drinking all the wine, we parted for the night. I regretfully closed the door to my room and started to undress. The nightgown was back on the pillow and this time I put it on. I could no longer control my emotions, The feel of the silk from breast to ankles caused an erection I couldn't ignore and it only took a few quick strokes to bring me to a, more or less, satisfying climax. I was able to sleep afterwards curled in the erotic feel of silk.

I woke early next morning and put the gown on over the nightdress as I went to the shower.

"Go in and help yourself" Michelle called from the kitchen. "Find something to wear." Now there was a thought. An invitation to investigate her lingerie. I opened the drawers and pulled some panties and bras aside. I was spoilt for choice. I wanted to try them all on. I settled for a white satin set and camisole. I dressed in these and found a pair of honey coloured stay-ups. Opening the wardrobe posed even more of a problem. I had no idea what went with what so I chose a green mini skirt and white shirt top with short sleeves. I retrieved my wig and did my best with it but the makeup threw me. After several attempts I wailed for help and Michelle came in laughing. She fixed my face quickly and expertly and we went into the kitchen for coffee.

"I like what you're wearing" she said. "you have good taste. "

"It's what I would like to see you in" I said. "And I know you have good taste."

We spent the morning playing with makeup and by lunchtime I was getting good at putting it on myself. We had a bite to eat and afterwards I decided I wanted to go shopping. The internet of course. I placed my plastic on the desk and said, "Michelle, these are for us. I want to buy he clothing today for both of us. We share. OK?"

"If you say so." She replied smiling. "But I have expensive tastes"

"Good. So do I" I said.

I spent a fortune that afternoon. She showed me all the best shops to buy clothing and we discussed each item in detail. I also managed to order my own set of breasts and something called a gaff which looked awful but apparently would be needed if I wanted to hide a certain bulge.

We also did some deportment lessons. I hadn't got out of spreading my legs when I sat down – something even I noticed and definitely un-ladylike. Se showed me how to walk more attractively and even how to stand.

In the evening we just listened to music, drinking malt whisky, talking softly about our tastes in clothes and discussing hair styles. Michelle had a lot of fashion magazines which we happily browsed through, metaphorically spending our annual wages several times over. It was two o'clock before the first yawns started and we headed off to our rooms for the night. I was getting quite frustrated now, having to say goodnight to a beautiful girl without even a kiss and going to sleep in a negligee but didn't know how to approach the subject without spoiling everything. I was also still aware she was a man dressed as a woman but it didn't seem to matter now.

Sunday morning we both slept late and dressed casually in short skirts and tops. It was a warm sunny morning without a cloud in the sky.

"Let's drink our coffee into the garden" She said smiling "Don't worry, no-one can see in and the fresh air will be nice" Nice wasn't, perhaps, the best word to use. The light breeze around my stocking covered legs and panties was very erotic. It was a new feeling altogether. The thought that my balls were only separated from the outside air by the thinnest of nylon started an immediate erection. I covered it as best as I could but I thought Michelle had noticed.

Wow, "I said "This is amazing. "I feel as if I've got nothing on"

"I thought you'd like it," she said "I often come out here where no-one can see me."

We sat at the garden table and sipped our drinks. "Are you enjoying your weekend as a woman?" she asked. "Do you still think it's for you?"

"I thought a few moments and replied "I love the feeling of the clothing. It's totally different to being dressed as a man. Every article has a texture all of it's own and each one is exciting. I also like looking good..."

"Looking beautiful, you mean" she interrupted. "You look beautiful she said more softly.

I blushed and continued, "But I don't really feel like a woman. I'm still very aware I'm a man playing dress-up."

"I do as well, "she said quietly, "I don't know If I will ever feel a complete woman. Perhaps time will tell."

"Perhaps, "I said "In the meantime, yes I am enjoying all of this and I'm not looking forward to having to put my old clothes on and spend a week in trousers and shirts."

"Why don't you take some clothes home with you? You could dress in the evenings and sleep in something nicer too." She said enthusiastically.

"No" I laughed. "They're your clothes.

"I've loads of clothing here" she said "Go on, take some with you."

I thought a few moments. The idea did sound attractive. To be able to slip into something nice sexy after work had definite appeal.

I smiled. "OK, lets go for it. "

"In fact, don't bother changing to go home. Just go as you are." She suggested. "You don't have to get out of your car till you get home. No-one will see."

This suggestion took a bit more thought. Suppose I had to stop somewhere. Suppose the police stopped me for something. Neither of these had ever happened before and there was no reason they should happen now.

"Ok" I said, grinning "Thank you I will."

So, that evening Michelle packed a small case with clothing we had chosen and I drove home with them in the boot. It was a totally uneventful journey, fortunately. Every time I stopped at lights, I thought people would stare but apart from a couple of appreciative looks from men in the lane beside me, It was a quiet journey. I parked up in front of the house and took the case from the boot. I had forgotten the neighbours but as it was dark, I didn't think anyone had seen me. "Anyway" I said to myself "I don't think they'd recognise me".

So that night I slept in my own bed in a white satin baby doll nightie and woke early Monday morning, feeling wonderful.

Chapter 7

The week passed slowly and work felt more tedious than usual. Each evening I would shower and change into stockings, panties and either a chemise or dress and browse the internet for make-up tips or hairstyles. I bought a new wig for myself. Long, blonde with loose curls. There seemed masses of hair and looked fabulous. It covered my shoulders in a shower suited my face perfectly. It arrived in time for the weekend and I tucked it away so could surprise Michelle. I also bought her a new wig in a similar style but brunette with red highlights.

At last Friday evening arrived and I rushed home to shower and change. I dressed in a brown and cream print dress made from the thinnest material that flowed seductively round my body. A white camisole peeped out of the v-neck and I wore a thin gold chain around my neck. I took special care with my make-up thought the final result was pretty sexy. I loaded my suitcase into the car and set off to Michelle's house. On the way, I stopped at some lights and a large BMW pulled up beside me. The driver was a young man wearing an expensive looking suit. He looked in at me and smiled. Feeling naughty, I lowered my lashes and gave him the sexiest smile I could. His eyebrows lifted and his grin grew wider. The lights changed and I drove off smiling to myself. I hadn't found him at all attractive but the encounter gave me a lot of confidence in my appearance.

Michelle opened the door as I walked up the path. She looked incredible and very desirable. "Hey you look wonderful "she cried as I carried my suitcase inside. "How was your journey?"

I told her about the guy in the BMW who had looked at me and told her about my week. "It was great to be able to wear lovely clothes all week" I said .

"I thought so" she said smiling.

All our internet purchases had arrived and the evening was spent, each of us trying them on and parading around.

"How about we go shopping tomorrow?" she suggested. I must have looked horrified. "Not local, into the city. No-one will recognise us and we can shop till we drop" she laughed.

"But I'm not sure..."

"You look great. " she interrupted. "Really beautiful. Trust me."

"Well, OK" I said but it didn't feel Ok. I felt very nervous.

Saturday morning we were up early, which was just as well as I took ages over my appearance. Nothing seemed good enough for me. I tried on every dress, skirt and blouse we owned. Altered my make-up a dozen times and brushed my hair till it crackled.

"Well you have one very feminine habit" she said grinning. "Come on for God's sake. We're going to miss the shops at this rate."

Eventually, we climbed into her car and set off. "I feel so nervous "I said weakly

"I know how you feel, remember. " Michelle said "Just don't worry. You really do look good you know." I nodded and looked out of the window.