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I Remember The First Time I Tried On Womens Clothing

Personal Stories, Advice, and Support 229 People

    My First Time!

    The first time I wore a dress was when I had a huge dress up box. Some of the clothes in there was a pink dress. I was 6 or 7 at the time and I put it on and felt great. We lived in a trailer then and from that point I would keep wearing the pink dress when I was alone or...
    Natalie121 Natalie121
    18-21, M
    Jul 21, 2011

    First Time Fully Dressed

    I have told the same story many times about the red thong on other groups so here is the time I fully Dressed up I was 13 in the bathroom I was wearing the red thong + bra then saw some of my moms pants I pulled them up I could feel they sat differently then boys then a tank top...
    mazzz77 mazzz77
    18-21, M
    Sep 18, 2010

    First Time

    My first experience was with my mothers slip when I was about 9. I could believe how soft it felt. I remember pretending to be ill so that I could stay home from school. The moment I had the house to myself I was rummaging through her drawers. The drawers in her dresser I mean...
    deleted deleted
    Nov 10, 2010

    I Just Coulden't Resist.

    I was like most cross dressers when they discovered the joy of wearing their moms clothes clothes. I was about 13 years old and my mom was in her early 30's. She wore pantyhose regularly for work and other reasons. I always had a thing for soft and silky material form a young...
    putmeinpantyhose putmeinpantyhose
    36-40, M
    Oct 19, 2010

    Tristan Was Born...

    I was 7, We had my cousins overnight. We were playing hide and seek. I found myself hiding in my mothers closet, surrounded by high heel shoes as i crouched in the corner. Dresses, skirts and blouses hanging overhead. I looked down next to my feet and saw a pair of dark red...
    Tristantvcd Tristantvcd
    46-50, M
    Apr 20, 2010

    Mama's Girdle

    i don't know why i did it. but i do remember, i was 13. i found one of mother's girdles, and i put it on. it was a white, plain panty girdle. it was exhilerating, sexy, powerful, shameful, scary, confusing. like i said, i don't know why i did it. but there had to be a...
    Nita427 Nita427
    56-60, M
    Jul 23, 2010

    My First Time

    The first time I crossdressed, I was around 12 or 13 years old. I ditched school and went home. It should have been safe because my brother and sister were at school and my parents were at work. At any rate, I raided my sister's closet. I donned a bra, blouse, panties (which I...
    deleted deleted
    1 Response Jun 16, 2011

    Was I That Young

    My first experience was when I was about 6 and I remember my mum had this dress, navy blue, with cream buttons at the front from the waist upwards. (c1958). I was sat on her knee, and for some reason I wanted to put her dress on. I started undoing the buttons down the front. She...
    sarahuniform sarahuniform
    51-55, M
    1 Response Mar 12, 2011

    First Time Wearing

    I started crossdressing when I was younger by mistake when my mom left a clean pair of discarded briefs on top of my clean laundry. I tried them on that night and have been hooked ever since. I started wearing everything else, including bras, pantyhose, and all kinds of lingerie...
    pantiescouple pantiescouple
    Jul 19, 2010

    I Remember

    I remember it like it was yesterday, the first time I tried on female clothing was after nicking a pair of tights from a school mates sister I was about 14/15 at that time but it was not until I was 23 that I first dressed fully en-fem & I quite enjoyed being dressed fully en-fem...
    xdpaul xdpaul
    56-60, M
    Jul 8, 2011

    Dressed By Schoolgirl

    How I became a cross dresser with a fetish for schoolgirl uniform, humiliation, small winkie humiliation... My mother used to work and was not home until 6pm so it was arranged for our neighbor to take me in her house for two hours after school and I could play with her14year...
    rachelusissy rachelusissy
    31-35, M
    Jun 4, 2011
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