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I Have Been Cross Dressing Since I Was 14

Personal Stories, Advice, and Support 73 People

    Why 14?

    I was cross dressing long before I was 14, I had two older sisters and would wear their clothes whenever I was home alone. I got caught but that is another story! I believe that crossdressers are born not made and there is more to it than just puitting on a pair of high heels etc...
    wetrev wetrev
    46-50, M
    3 Responses Jul 4, 2012

    Well 12 Or 13

    More like 12 or 13 I started wearing moms bras and panties. I also wore her dress and the shoes were too small. I loved to wear her girdles and stockings and half slip. Doesn't the lingerie just call to you? Wear me, wear me. In my case it did. It is soft and the feeling...
    jml2000 jml2000
    61-65, M
    3 Responses Apr 20, 2013

    Long Before.

    My first time cross dressing I was 6 y/o. My first g/f caught and dressed me when I was 13 y/o. My wife caught me when I was 19, 1 month after we wed. My wife loves helping me dress and doing my make up to this day, we have been married over 30 years and haven't had naked sex...
    sherrynpantyhose2k4 sherrynpantyhose2k4
    51-55, T
    2 Responses Mar 22, 2012

    Wellllllll... More Like Sixteen

    That's when i learned from my stylish friend Nancy how many different outfits i could make just by mixing & matching my blouses and skirts. We never called it cross-dressing back then, though. We just called it "mix & match".
    eleanorssong eleanorssong
    56-60, F
    3 Responses Jul 21, 2012

    I Started At Age Of 14 Too

    I was shy teenage and had crush on student named Camille, a lovley BBW who rented the basement suite in my parents house. One of my weekly chores was to clean the apt, then Camille moved early she left four worn out in the trash. I put her 36DDD and I hooked, I was more skinny...
    BigbustyDolly BigbustyDolly
    51-55, T
    4 Responses Sep 18, 2012

    I was always tempted

    when I seen my sister's panties in the bathroom. I was 13 or 14 and I just started ************. I tried on a pair. O I was so turned on by the feeling in the crotch I couldn't take it took them off in like 20 seconds. The next time weeks later. I put on a pair of floral...
    deleted deleted
    26-30
    2 Responses May 20, 2015
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