I Began Crossdressing At A Very Young Age

Personal Stories, Advice, and Support 633 People

    I Dressed In My First Skirt At Age 11

    I must have been age 11 when I first wore an item of femme clothing. It was one of my sister’s skirts. A little black number with small red roses printed through the fabric. It was placed on a chair waiting to be ironed. I was watching kids TV at the time and all alone in the...
    Lesleygb Lesleygb
    46-50
    10 Responses Apr 28, 2013

    I started cross-dressing at seven.

    That is when I bought my first bra and panty set. I was nervous as hell and tried to play it off that it was for my girlfriend. I don't think they fell for it. I bought several more sets there along with other female clothing. I also bought my first diapers and plastic pants...
    Thejannettearmet Thejannettearmet
    56-60, T
    Apr 13, 2016

    I began one day when I went over to a friends

    place years ago. I was 10 at the time and my friend and his sister were playing and doing silly stuff downstairs. Well as the play went on his sister throw this black nightie at me and told me to put in on because they wanted me to be a girl. From that day on I knew I was...
    deleted deleted
    26-30
    4 Responses Nov 13, 2015
    prodemonz prodemonz
    16-17, M
    1 Response Apr 20, 2015

    The Day I was Born! My mom was certain I was

    going to be a girl and insisted all her baby shower gifts, etc, had to be for a baby girl. As I outgrew those, they were replaced with more girls clothing. At the time, it wasn't unusual for little boys to wear dresses especially if they were still in diapers as it made changing...
    AlbertSAT AlbertSAT
    66-70, M
    4 Responses Aug 13, 2015

    The Begining

    Jamie as she is now came into the world at age 9 when i found some of my sisters clothes in the bath. i have no clue why but i just had to put them on this started my 40 year obsession with all things fem
    spaz1177 spaz1177
    46-50, T
    1 Response Apr 28, 2013

    Cross Dressing

    I didn't start wearing my mom's clothes as early as many here on EP. It was as if her clothes were calling out to me. I just had to try them on. So I did. What an amazing feeling! Something I had never felt in my boy clothes. It felt right too. Then fear crept in and I had...
    jml2000 jml2000
    61-65, M
    3 Responses Jun 9, 2013

    I was potty trained in my sisters panties

    and loved them. We could not afford reg boys underwear all the time so I always got my sisters. I loved whin she switched to thongs. The 1st thong I put on I had backwards bc she told me that was how they went before she switched to thongs she even showed me how a thong was...
    deleted deleted
    26-30
    1 Response Dec 15, 2014

    I was about 10 ish..I wore my mams things.

    then wen I was about 14 till 16 it went 2 my sisters underwear then wen eva could get them.. wen I was about 20 I manged get my best friends (witch I would rather not talk about) wen i was about 23 i wore leggings, underwear, disco pants, bikini ect. Now at 25 I wear my wife's...
    deleted deleted
    26-30
    4 Responses Sep 20, 2015
    cristyfontana cristyfontana
    18-21, T
    4 Responses Jun 11, 2015

    i began cross dressing at age 10 i always felt

    my body wasnt right till one day no one was at home so i was playing with my sister dolls i looked in her dresser found her Bra and panties so i put them on they felt so nice i been wearing them ever since i always felt like a girl love barbie dolls i always sit to pee when i...
    deleted deleted
    26-30
    1 Response Mar 20, 2016
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