I Remember The First Time I Crossdressed

Personal Stories, Advice, and Support 300 People

    This happened when I was in the fourth grade.

    We had our traditional new year festival. It was a only boys school and I was one of those in my class chosen to dress as a girl for the festival. I wore a print skirt and a blouse, with a bead necklace, and had my face make up. I also wore a long wig of waist length hair worn...
    Nilooshi Nilooshi
    2 Responses Apr 27, 2015

    I was 14 at the time

    and was going to be home alone all day. My mother had this beautiful red nightgown hanging in the bathroom. It was soft and silky. I tried it on and it felt so wonderful! I kept going through my mom and older sisters closets and tried on anything that looked feminine. My...
    Stephaniegirl226 Stephaniegirl226
    41-45, T
    3 Responses Apr 1, 2015

    I don't completely remember the first time I

    cross-dressed because it was before I could make accurate memories. What I do remember are feelings and some details. I have a cousin 4 years older than me. She doesn't have a sister, so she used to dress me and her little brother, who is 2 months younger than me, in her dress...
    Yoshi9ist Yoshi9ist
    26-30, M
    2 Responses Jan 23, 2014

    First Time

    i was 14.walked to barkers dept. store.walked around and around.very nervous.i had shopliifed before so it wasn't that.walked to bra alise and took first one i saw.[36a crossyour heart] ran home up to my room.shakeing as i put it on.didn't have any trouble at all.i had no boobs...
    donnapoplin donnapoplin
    51-55, M
    1 Response Jan 13, 2011

    I remember running around the house dressed

    as a girl. I didn't know society frowned upon such things but I don't believe I ever went out of the house dressed that way then.
    Mistydawn2 Mistydawn2
    66-70, M
    Jan 27, 2014

    I was probably around 8

    or 9 and my cousins came over do my female cousin could try on my kind old heels. I was hanging with my male cousin he was playing video games but it got boring cause he never let me play so I went to go see what my female cousin was doing. She was trying ok shoes so I joined...
    TheDoctor2234 TheDoctor2234
    1 Response May 18, 2014

    It was the result of a bladder blunder.

    Was at my cousins house, she was same size as me. Only thing I hd to change into was some stuff of hers. Denim shirt and panties.
    pardax pardax
    16-17, M
    Dec 29, 2015

    I was 11yrs old when my Mom was telling my

    sister that she need to start wearing a bra. She went shopping earlier for her stuff that day. As my mother was pulling bras and new panties out the bag for me sister to go try, I couldn't stop looking at them... A feeling of wanting to try them. But as old times it's a no-no...
    PinkblueCD PinkblueCD
    41-45, M
    Feb 12, 2016

    I was 24 and had recently tried bi sex.

    the guy had a fantasy of someone crossdressing for him. so I did and felt so slutty but yet good.
    abqmongo69 abqmongo69
    41-45, M
    Apr 2, 2016
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