• =?UTF-8?Q?My_Initiation=2c_bycdandy=c2=a9_long?= (2/3)

    From a425couple@21:1/5 to All on Fri Oct 4 15:53:38 2019
    [continued from previous message]

    "Oh... no... of course. "I said. And slipped them down. This was a first
    for me, not being accustomed to standing naked in front of anyone.

    I took the belt and she turned around to the drawers for more clothes. Eventually I figured it out and fastened it around my waist. It was pure
    white and made of some fine, wide, shiny lace with pale blue embroidery
    running through. The straps ticked my thighs enticingly. She handed me a
    pair of honey coloured stockings and I sat on the edge of the bed to put
    them on. The feeling was again, exquisite and I felt the beginnings of
    an erection. I clipped them to the suspenders and a pair of the most
    beautiful panties floated into view. They were high cut lace and matched
    the belt perfectly. I stood up and felt the stockings pull slightly. She
    handed me a matching bra and showed me how to put it on backwards round
    my waist and slide it up to my non existent breasts. I looked down at
    myself, disappointed, as if I should have magically grown something to
    fill the bra.

    "Head up." Michelle demanded and she slipped two breast shapes into the
    cups. She handed me a white satin camisole top which I slid over my head
    and new breasts followed by a soft, silky waist slip. The hem was all
    lace and my erection finally made it to the vertical. The combination of
    soft, silky and totally erotic materials caressing my body were nearly
    too much. I managed to control myself with sheer willpower.

    "It should really have been a full slip but I've only got one and I'm
    wearing it." She said and lifted the hem of her skirt to reveal a
    similar lacy frill. "Sit down here please "she said and indicated a
    chair beside to vanity unit I carefully moved over to it and sat down
    facing the bed where she sat with a variety of cosmetics laid out beside
    her. I followed her instructions, closing or opening my eyes as
    requested – studying her beautiful eyes when I could. After what seemed
    an age, she smiled approvingly and went to the wardrobe coming back with
    a long blonde wig. She fitted it and teased a few hairs into place with
    a brush.

    While I fiddled with the fine material of my clothing and looked at my
    heavenly new shape she went to the wardrobe and returned with a pale
    green chiffon dress. It was multi layered and looked stunning. I stepped
    into it and ran my hands down my breasts as she zipped it up. Handing me
    some low, white sandals she stepped back and covered her mouth, her eyes
    wide.

    "Oh God...You are beautiful." She gasped "Much more than I expected."

    I twirled on my heels and the dress billowed out, creating a delicious
    draught on my thighs.

    "Go into the bathroom and look "she said "there some full length
    mirrors. Walk slowly in those shoes." She seemed breathless.

    They weren't very high heels but they were narrow and tricky to walk in.
    Every step pulled or caressed some part of my body. The straps across my shoulders, the suspenders pulling at my thighs, the hem of the skirt
    flicking against my calves... It was a long delicious journey.

    I reached the bathroom and went in closing the door behind me. The full
    length mirror was covered with a towel and I realised, that all the
    mirrors had been covered. I smiled. This had all been planned long
    before I arrived.

    I reached up and took the towel down. There stood a beautiful blonde
    girl staring back at me. She was stunning. I couldn't believe it.
    Instead of the pancake makeup I had expected, this was light and barely noticeable. A hint of eye shadow, faint eyeliner and she'd done
    something wonderful with blusher. I looked young and the shape of my
    face was changed. My eyebrows had been subtly moved and my lips were
    just the palest rose colour. I stepped back and looked at my body. I was
    a different shape. Curvy, sensual. Nice small breasts. I twisted round
    to look at the back and noticed another mirror covered behind me. I took
    down the towel and looked at the reflection from the mirror behind.
    Shapely and very sexy. I lifted the hem of my skirt and gazed at the
    sticking tops framed with the lacy slip. I lifted it higher and my
    panties came into view. Dropping the dress, I touched my hair. It felt
    soft and luxurious.

    I must have been ages stroking the materials and admiring myself - there
    was a soft knock on the door and Michelle said, "are you OK in there?"

    I woke as from a dream and called "uh... sure. Come in."

    "You like?" She asked

    "It's incredible... What you've done" I said. "

    "Come and have a drink and we'll eat." She walked out and I followed
    slowly, savouring each step. There was no question of taking it all off
    before dinner. Wild dogs couldn't have torn it off me. My appetite
    didn't do the lovely meal justice. I felt strange and had trouble
    stopping myself looking down at my body and touching my legs and body.

    After dinner we went into the lounge and with a glass of wine, sat on
    the deep sofa.

    "You should keep your legs together when you sit down" she said, her
    eyes sparkling "It's more ladylike."

    I snapped my knees closed and sat looking at my hands.

    Finally I asked "Well, have you achieved your goal?"

    "My goal?" she said with eyebrows raised.

    "You asked my if I'd do you're a favour and dress up for you" I smiled.

    "In that case, yes."

    "Why did you want me like his" I asked.

    "Well... you've been asking me what it felt like, why do I want to be
    feminine and all sorts of questions about cross dressing for weeks now.
    So I wanted you to find out for yourself. "She replied.

    "I don't feel like a woman" I said

    "But do you feel good?" she gave me a sexy smile.

    I blushed. "I feel ... terrific" I said grinning.

    "But, how do you feel?" She persisted.

    "Sexy, beautiful, erotic. I feel like I don't ever want to take it all
    off." I said quietly

    "Then you understand some of what I feel" she said. "The erotic feeling
    of dressing in underwear wears off after a while but the feeling of
    being beautiful doesn't. When I am living as a woman, I am alive and
    feel sexy. When you dated me for the first time, I felt wanted and
    admired. It was the highest compliment anyone could have paid me."

    I nodded and took a sip of my drink. I knew Mike wasn't gay. We'd looked
    at women they way men have been 'checking out the talent' for
    generations. He'd never made any advances toward me, in fact the
    opposite. While I had wanted to sleep with her after 'late night
    coffee', We had always said goodnight the way friends do.

    "Is that the only reason you asked me to dress? Because I showed an
    interest?" I asked.

    "No." she looked guilty. "I saw I could make you beautiful. You have
    very sensual eyes, a lovely shaped face. You have a good figure and ..."
    She got up and poured another drink. We were on the malt whiskies now
    and both of us were in a confessional mood.

    "And?" I smiled at her, accepting the glass.

    "And I can't answer that at the moment." She said.

    "OK. Interrogation over. I'm sorry Michelle. This is a bit of a culture
    shock for me. I have never worn women's clothing before and I'm finding
    out I may have missed something in life. Cross dressing has always
    seemed to be a fetish – like bondage or whipping. It's just something
    that's never crossed my path before. And here I am enjoying it."

    "I think you need to sleep on it." she said jumping up "It's late and
    you have drunk too much to drive home. I've made up the spare room for
    you. "

    Yes, I was tired the combination of excitement and drink had drained me.

    She led me to the spare room and hugged me as I entered. "I'll unzip
    you" she sad smiling into my face "And I'll do you" I said. Not sure if
    she would catch the double entendre. "Judging by her expression she did!

    She turned and I unzipped her dress and, sliding her hair to one side,
    kissed the nape of her neck.
    Report Story
    bycdandy© 109 comments/ 636343 views/ 163 favorites

    My Initiation
    bycdandy©
    "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.
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    bycdandy© 109 comments/ 636343 views/ 163 favorites

    My Initiation
    bycdandy©
    We arrived in the multi-story car park and set off into the mall. For
    the first half hour I was looking in every shop window, not at the
    merchandise but at my reflection, checking my looks and making sure
    no-one was staring at me. Finally, I settled down and started to enjoy
    myself. At first it felt strange to be examining panties, bras, slips
    and other women's clothing. Several times a shop assistant would come
    over to help and Michelle never seemed to flap at all. Then in one
    department store, while we were looking at blouses and tops, Michelle
    said "Wont be a moment." and left. So here I was. In the ladies section
    of John Lewis, All on my own, dressed as a girl. At first I started to
    panic and then tried to hide amongst the clothes. She was only gone
    about ten minutes but it seemed the longest ten minutes of my life."

    "Where have you been? "I asked in a near hysterical voice.

    "I wasn't long" she said "Just had to err... you know...go."

    I smiled "Sorry. I'm just having an insecurity attack"

    She put a hand on mine and looked kindly at me "Sorry. I keep forgetting
    it's your first time out. You look so natural."

    "How many times have you been out?" I said. "I bet it's not many."

    "Well... "she said with an impish grin. "this makes twice. And it and it
    was you that gave me confidence. I feel quite comfortable."

    "Wish I did "I said

    "Come on. We'll go and have a drink"

    We went into a small wine bar and had a salad with a glass of wine.

    "You know, you really do look like a girl. " she said "I wouldn't have
    brought you out if I wasn't sure. If you just relax, you'll look and
    feel even better."

    I took her at her word and really did feel better. We carried on
    shopping and to our delight found an exclusive lingerie shop. The
    assistant left us alone to browse and we had the time of our lives.
    Underwear to die for. All matching sets made from the most luxurious
    materials. Silk, satin, chiffon – there was everything. We left with two large carrier bags and two very thin credit cards. I had bought us both
    a gown and nightdress set. Champagne for her and white for me. Although
    we always shared all the clothing, I wanted these to be special. We set
    off back to the car feeling happy but tired.

    "I've never had such a wonderful day "Michelle said as we drove home. I
    had to agree though I was secretly glad we were finished. Next time, I
    knew I would enjoy it more but at the moment, all I wanted to do was get
    this bloody gaff off and have a shower. I thought the gaff had been a
    waste of time. There was no way I would have got an erection and I'm not
    really that well endowed enough to have shown anything through this
    skirt. However, better safe than sorry, I thought.

    We each headed for the shower as soon as we got to Michelle's and I
    dressed in a simple pale yellow cotton blouse and a gypsy style skirt. I
    walked into the kitchen where Michelle was just ordering a couple of
    pizzas, poured her a drink and took it over to the sofa. I felt
    wonderful. The adrenaline was still buzzing in me and I suddenly knew
    what I wanted. I wanted Michelle but I was still on unsure ground. I
    didn't want to spoil everything by forcing some sort of gay sex on her
    but when she looked so damned attractive, her body parts didn't bother
    me. To me, she was a beautiful girl. The fact that I knew she had no
    breasts and boasted a respectable cock wasn't an issue. I knew she had a
    good firm body and to be honest, I wanted to kiss and hug her... and to
    sleep with her. Whatever followed from that was Ka, Fate.

    I answered he door when the pizzas arrived and made the guy's night by
    giving him a sexy smile as I gave him the money. We ate them quietly,
    not saying much. I thought there might be a slight tension in the room. Afterwards, we sat and drank a couple of malt whiskies, both reflection
    on the day's activities. "Shall we slip into something more comfortable? "Michelle said after a while.

    "That's a good idea. "I said" This bra's killing me. We both cracked up laughing and went get changed.

    I undressed quickly and got the new wig out of my case. I put it on and
    gently rearranged any loose hairs with my brush. A dab of perfume in the

    [continued in next message]

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