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I raised the hem of my dress and...

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  • I raised the hem of my dress and...

    To put it simply, a narrow escape leads this little TV into a lot of
    trouble.

    I loved these moments. My parents away for the weekend, my older sister,
    Stacy (she was 19, I was 15) looking after me. Of course, it was the
    weekend and there was no way she was staying in to look after her
    `pain-in-the-arse' little brother; I knew she had plans to go clubbing, big
    style. Anyway, who cares, I'm 15 now, and more than capable of looking
    after myself for a couple of days.

    So, it's late Friday afternoon, Stacy has gone over to Cheryl's (her best
    mate) to get sorted for their night out, she won't be back `til
    tomorrow. I'm feeling so exited. I slip into my parents' bedroom, heading
    straight for my mother's underwear draw. I loved this moment, the `now what
    shall I wear today' feeling!! Okay, I say to myself, lingerie!! I choose a
    pink satin and lace set, bra, panties and suspender belt with vaguely black
    lace-top stockings, I slip on the underwear, first the bra, then the
    suspender belt, roll the sheer delicate stockings up each leg, and finally
    the panties. Mmmm, I feel sexy!!! Slipping on a simple black dress and
    heels, I head downstairs; I'm not expecting anyone, so why not!!

    It's now 6pm (1800hrs) and having spent the last two and a half hours
    dressed up I'm feeling pretty bored, lacking the bottle to simply strut my
    stuff around town I take off the dress and heels (stuffing them in a
    nap-sack) and pull on my jeans, sweatshirt and trainers and head out of the
    house. We live in a fairly quite suburban area anyway, but some 350 yards
    from our house in a new building site, building these nice big houses; the
    area is quite well-to-do. I head towards the site, it's just around dusk,
    so the light is fading, I should be okay. I could cut through the fields
    behind our house, but I decide to take the normal street route, as it was
    just around the bend.

    Great, I was inside, all the workers had gone home for the weekend, and no
    security in sight (I knew they had security, but it must have been mobile
    as they were only there once in a while). I did a final check of the site,
    it was deserted, I slipped out of my clothes and pulled on the black dress
    and heels, managed to put my hair in bunches and applied a little
    lip-stick. I probably looked like a little school-girl, dolled up for her
    first attempt at night-club entry, but this was my private moment.

    I pranced around the semi-built house I was in, pretending to entertain my
    first guest, bringing him in a drink, hitching my dress up to flash my
    stocking tops at him, adjusting my suspender straps, etc. Just playing the
    giggling little tranny host, I guess. I loved popping from house to house,
    the paths were very uneven and difficult in heels, but I'd totter around,
    acting all girly. This I did for about an hour, then I heard a car engine
    come to a halt near the site entrance; sneaking over, I saw 2 security
    guards get out, flashlights in hand. They were chatting to each other,
    simple conversation, something about football, etc. They checked the first
    house, no problem there, then I could see that they were heading toward the
    house where I got changed.

    Shit, I thought to myself, my clothes!! They're just in a heap on the
    ground. In they went, then the discovery was made. I was about 20 feet
    away, I saw them pick up the nap-sack and my clothes and the lip-stick.

    "what's going on here, then" one said. "we'd better do a full site check"
    said the other. I didn't know what to do. What if they found me, what
    would they do to me? Oh, shit, shit, I kept thinking to myself. Right,
    composure. Must get out of here, main entrance is no-go, have to head back
    home over the fields. Not really a problem, but in my way, a row of houses
    being systematically checked, a pathway that would be almost impossible to
    cross quietly in these heels, let alone quickly, and a mound of earth and
    rubble that's approaching ten, maybe fifteen foot high, that's even before
    I get to the field.

    Okay, they moved from house 2 to house 3, time to go I thought. Off with
    the high heels and out. The pathway was difficult, but I scampered across
    fairly quietly and into house one. What a relief. I slipped the shoes back
    on and began tip-toeing across to the back of the house -- no good, too
    loud, off they came again. It was only about 10 meters to the mound I'd
    have to traverse to get to safety. I watched as they came out of the back
    of house 3 and into 4. Off I went, quietly across the back yard area and up
    the mound of earth, just in my stocking feet, finally down and there I was,
    safely at the edge of the field. I slipped on the heels, noticing just how
    badly the soles of my stockings were laddered. Nevermind, I thought, just
    this field and the small wooded area right behind our house and home safe.

    Off I went, the field was no problem, it was dark now, I doubt anyone could
    see me. A couple of minutes and I was across, the wooded area was only
    about 100 yards long and came out by our back garden. In I went, not a real
    problem, I just kept catching my stockings on brambles and branches. So
    what, they were knackered anyway. Actually it felt quite exhilarating, I
    could imagine myself having a guy in here, late at night, just the faint
    glow of the moon over us as he jabbed away at my fuck-hole, making me suck
    his cock, then finally emptying his ball over my stockings (such was this
    fantasy of mine). Jeez, I could feel my cock straining in my panties. Out
    you come, I pulled him free. In fairness, I wasn't a bad size, even at
    fifteen. As I walked along I tossed at him, almost bringing myself to
    climax, but no, I'll wait until I get inside, I thought.

    Back of the house now, back door was locked, but we kept a spare hidden in
    the shed. I was at the shed door when our next door neighbour (Old Bob we
    called him), stepped out into the back of his garden. To my horror he
    headed my way,

    "Andy, Andy. What the hell..." He said.

    "Oh shit. Bob" I said, "look I can explain, I ..." He cut me off.

    "Being a bit more adventurous these days are you?" said Bob, he came into
    our back garden, with that our outside security light came on, I was there
    in all my glory for Bob to see.

    "Oh, what happened to you, are you all right" he said, he could see my
    bedraggled look, laddered stockings. He came closer, and put his hand on my
    shoulder.

    "Now" he said, "I guess you don't want mum and dad to find out do you, so
    be a good girl and give me a kiss". I did. I felt his tongue ravish the
    inside of my mouth. To my surprise my cock raged into hard-on. His hands
    made their way over my body and down to my groin where Bob could hardly
    miss my obvious excitement.

    "So, Andy, no, Amy, you like this do you?" asked Bob.

    "No" I cried, "I don't, but...but, yes I do". I suddenly felt my
    inhibitions disappear.

    "Yes, Bob, ahhh, yes. Can I be your tranny slut tonite?" I asked.

    "Oh, now you're talking" he said, "come on into my house".

    "No, here, now and in the spook (our nickname for the wood)" I asked,
    giving him my best girly pout.

    With that I raised the hem of my dress and gave Bob a good flash of
    stocking top, his eyes just glared, he was on fire. He slid his hand up my
    dress and over my stockings, over my bare thighs to where the suspender
    straps disappeared into the panties. I stood back, kicked off the heels and
    slowly, seductively slipped off the black dress; I was there, the first
    time, dressed in just lingerie, with laddered stockings, just for the
    pleasure of this man. I moved closer, Bob pulled me close and we kissed
    again, this time with more fire, his hands caressed my semi-naked body, my
    cock was rock-hard and virtually bursting out of my delicate pink
    panties. Bob dropped to his knees and pulled my cock free. He looked up,
    gave me a little wink and took my cock right in. I almost collapsed with
    the feeling, this was sheer heaven. I wasn't long before I was coming, and
    Bob took every last drop.

    "did you like that?" asked Bob, just licking a drop off cum off the end of
    my cock, "now it's your turn".

    I stepped out of my panties and beckoned him into the spook. I dropped to
    my knees and undid his trousers, pulling down his pants, this nicely sized
    cock bounded free; it looked gorgeous. I took it straight in my mouth, it
    felt warm, yet silky, I could taste his pre-cum, it tasted good. To be
    honest, I was pretty crap to begin with, but Bob fired me a couple of tips
    and soon I was sucking like a pro; taking him deeper, caressing his length
    with my tongue, nibbling his sensitive purple helmet. Soon he emptied his
    load into me, I simply couldn't take it all and let it drip out onto my
    stockings. My first taste of cum; it wasn't as nice as I thought it would
    be, but a taste I could soon learn to enjoy, and would. I finished Bob off
    with a foot-job, just getting his last few spurts over my stockinged
    feet. I stood up and we walked back into my back garden.

    I explained that mum and dad were away for the weekend and Stacy was out
    clubbing. My next instructions were clear. Tomorrow night I was to go over
    to Bob's house where I would take my next step to becoming his.


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