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I First Time Crossdressing

Personal Stories, Advice, and Support 74 People

    Love For Green Dresses

    Even though I had an interest in crossdressing going back to even preschool I did not seriously crossdress until my early teens. I must point out that I was an only child and thus did not have a sister who would dress me as many have had. One day I saw a picture of a dress that...
    PamelaSue PamelaSue
    61-65
    1 Response May 25, 2013

    Shannon

    I first met Shannon when she joined the company I was working for at the time. At first I was her boss and she used to reply YES BOSS to my requests. I knew from that she enjoyed master servant role play. However within a month she got promoted and started female power dressing...
    deleted deleted
    26-30
    Nov 27, 2013

    My Secret

    I have been cross dressing since I was an early teen, I am now a married man even while secretly craving to be seduced and used constantly. If only I could find someone that has just as much to loose.:(
    mellisajo mellisajo
    31-35, M
    May 25, 2013

    Learning My Desires

    I have never shared this with anyone. When I was young and going through puberty I would think about being a girl. We lived on a farm in the N.W. 1 year for a church play we dressed as gypsies after words the costumes she made ended up in a trunk in the barn. Where the stacks of...
    jenniferalexander jenniferalexander
    46-50
    5 Responses Oct 20, 2013

    Satin Bridesmaid Dress

    100% Male & My story crossdressing:: As I slide into my bridesmaides satin dress (took from ex girlfriends 19 yr sister trisha from her bedroom when no one was home for a week, more on this later*) it covers my naked body and smells so good (Like trisha) and my penis so hard and...
    ohhyess1 ohhyess1
    26-30, M
    2 Responses May 5, 2013

    1973. I bought Alice Cooper's school's out

    album. Inside were a pair of paper panties. I had never worn panties before even though in first grade at an all boys school we did the can can and in sixth grade I was yum yum in the mikado. Soon I buying my own panties in department stores and found a transvestite boutique on...
    LuanneW LuanneW
    66-70, M
    5 Responses Dec 12, 2013
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