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I Loved Dressing As A Girl When I Was Just A Young Boy

Personal Stories, Advice, and Support 523 People

    Didn't know why - just seemed natural.

    It started when my mom was so sure I'd be a baby girl that she insisted all her baby shower gifts and other preparations be for a baby girl. So I can honestly say that cross-dressing for me began before I was born. She kept me in diapers and dresses until my little sister was...
    AlbertSAT AlbertSAT
    66-70, M
    4 Responses May 23, 2015

    Nieces Clothes

    One day, my aunt brought several bags with clothes of her girls not fitting any more or what they were not wearing any more. Her daughters were 1 year older and 1 year younger then me. One day, in my curiosity, I went through the bags to see what clothes they worn and at one...
    Kadya Kadya
    41-45
    3 Responses Apr 13, 2013

    The Shopping Trip

    Hi Folks: I still owe you the second part of the true story about my GF. I had a hard drive crash and I'm still trying to recover my files. Like a dummy, I did not back anything up. I hope to recover the files rather than have to start from scratch. In the mean time I'd like to...
    francenemarch francenemarch
    66-70, F
    Jun 19, 2013

    for me it was done out of love I still knew who

    and what I was but for this one person it was done out of love for them it was fun playing as a girl no matter what age we played or playing with dolls or even role playing with me as the young innocent girl and her dressed as the James dean look and trying to be the first to...
    rickibrat2 rickibrat2
    61-65, M
    3 Responses May 23, 2015

    Discovering Silky Panties For The First Time

    I wanted to revisit my childhood and give a little detail of how I started. I really don’t remember any of it but a short time after I was born my mom went back to work. Consequently I was sent to a family friend who babysat me. This went on until I was almost 4 years old. (The...
    francenemarch francenemarch
    66-70, F
    7 Responses Mar 2, 2013

    My cousin used to dress me

    when I was little and I loved it.
    RJMC65 RJMC65
    46-50, M
    4 Responses Mar 4

    I was molested age 14,

    in the cinema by older guys and loved it so much I kept going back for more. One took me to his home and dressed me in sweet girlie clothes and silky undies and paraded me in front of his friends for sitting on laps, kisses and cuddles and eventual revealing as a boy.
    deleted deleted
    26-30
    1 Response May 11, 2015

    Curiosity Made The Sissy

    My own experience seems like a sissys dream come true and it was, only i don't think i full appreciated it at the time. How i wish i could go back and fully immerse myself in the wonderful cocoon of love, kindness and comfort i knew. I was staying at my aunties place in chingford...
    charlisilk charlisilk
    56-60, M
    2 Responses Jan 25, 2013

    My Hidden Shame

    It all started when I was around 11 me and a girl from school lived next store to each other so we would hang out sometimes one day when we were bored we went up to her room and had a game of (girls)as she called it so we dressed up in dresses and heels and messed around...
    callmebabygirl callmebabygirl
    26-30, M
    4 Responses Jun 2, 2013

    My Feminization: A True Story Of A Transsexual Becoming A Woman

    I started telling of this in another story that I wrote for the group ‘I Am Dedicated To Being A Good Wife.’ This is a true story that took place back in the mid 1950s. Even though I have the genitalia of a male I do consider myself a woman. Although I started with how I...
    JulieLisa JulieLisa
    61-65, T
    1 Response Jul 14, 2013

    It was so exciting dressing

    as a girl, I used to wear my older Sister's knickers and her school dress and blazer and pretend I was a Girl from age 7 onwards.
    timothy1994 timothy1994
    22-25, M
    Mar 13
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