When was the first time you crossdressed? How old were you? How was it?

Answer 1

I was about 7 or 8 and my aunt dressed me up as a girl one weekend. I loved it and I dressed as a girl every Halloween after that and would dress as a girl every chance I had. And I haven't stopped cross-dressing yet & never will.

Answer 2

13 14

Answer 3

I guess I have been cross dressing my whole life. I am a girl and I wear pants every day. I would much rather wear pants than a skirt or dress. I did wear a tux to prom though. It was so nice not having to wear some really uncomfortable dress that cost too much and that I would never wear again.

I do remember my brother putting on a "princess" dress when he was 10 and a bunch of make up. He was really pretty. Prettier than I and it made me jealous.

Answer 4

The first time a fully cross dressed (snuck my mom's panties and bras from time to time before) was when I was 12. I pretended to be sick and my mom called me off sick before she went to work ( she knew I was faking, but let me do it anyhow). I snuck into the school after everyone was in class and hid in the boiler room for an hour. I knew my class (I was in a Catholic school) was in gym second period and I waited until they were outside playing and I went into the girls locker room and looked for a girl named Nicole's stuff. She was pretty close to the same size as me and I stole her stuff and went home. I put on her clothes (school uniform skirt and pink blouse, pink knee-high socks and the black and white shoes that all the girls wore back then (the early 80's). It felt so wonderful to walk around my house in a pleated skirt. I knew then that I wanted to be a girl and am now transitioning.

Answer 5

Well I was 21
And I was dating a hot cop guy that liked to see men in stockings and leotards and panties.
I didn't find the experience all to pleasing.
As I don't attach myself to the female gender that much
I don't think I will ever do it again except online for Second Life as I have made a drag debut looking very manly

Answer 6

I HAD A BOYFRIEND 12YRS AGO THAT CROSSDRESSED, 3YRS INTO THE RELATIONSHIP I CAUGHT HIM IN MY CLOTHES , SOME OF THE MANY THINGS HE STOLE OFF ME. I LEFT HIM 6 TIMES BEFORE I EVENTUALLY LEFT HIM FOR GOOD, MY SON AND I ARE DOING WELL. HE WAS SEXUALLY ASSAULTED AS A YOUNG BOY, GREW UP IN FOSTER HOMES, HIS MOTHER WAS A JUNKIE, A PROSTITUTE, SISTER COMMITED SUICIDE AT 21, BROTHER O D AND DIED. VERY SAD, HE HAS WORN WOMENS CLOTHES SINCE HE WAS 6, AND HE WILL ALWAYS DO SO NO MATTER WHAT

Answer 7

I did it once for amateur drag night. (LONG AGO!) I came in second, but I think that was due to the fact that I was wearing black patent leather and a chain mail dress, while performing to Concrete Blonde, instead of channeling Celine like the winner... I did have fun though!

Edit: I was 19.

Answer 8

i was 7, sneaked some of my cousin's things. Just tried to dress the way i felt, wanted to be pretty like her. i had been doing it awhile when she caught me. totally freaked out at first, but then she was cool and let wear her clothes and helped me out a bunch. Been dressing ever since-fulltime now that i'm away from home.

Answer 9

A lot as a kid, but only because girl's clothes didn't really fit that well (especially pants) since I was tall for my age (not anymore thought) But now, only sometimes for holloween and costume play. I love dressing as male characters.

Answer 10

It was in 1993 and I was 11 years old, and it felt different wearing them at first, but after a while it felt comfortable to wear, and I don't regret doing it.