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18 answers

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.

2007-04-11 16:29:28 · answer #1 · answered by J 7 · 0 0

My early teens, started out with my sisters dirtly cloths from the hamper - then got brave and tried on their cloths out of their closet when I was home along, from bra's, girdles, slips, skirts and was really happy when my sister bought her first wig. As other younge boys, I always asked to be dressed as a girl for halloween, worked until I was about 15 then mom said I couldn't do it as I was too old.

2007-04-13 00:15:17 · answer #2 · answered by Aloha in Silk 2 · 0 0

I was about three in my moms clothes and shoes, they were of course way to big but I liked it anyway, and have been doing it every since, though have been buying my own clothes since about thirteen.

First time I fully dressed with make up and a wig was when I was twelve.

2007-04-09 19:12:22 · answer #3 · answered by Christopher J 4 · 0 0

Well.... I got dared to wear a red dress for liek 30 seconds and let my friends take pictures and recordings. Stupid truth or dare games.....

EDIT: Not too long after that I was a old manly-looking mother in a musical. The characters that I'm asked to be....

2007-04-09 18:39:14 · answer #4 · answered by Tom 2 · 0 0

Never have but I would love too just once. Would love to have a makeup artist do me up. Then I would like to go out and pleasure a nice looking man. Just for kicks (and licks)

2007-04-15 10:26:46 · answer #5 · answered by vacationman 2 · 0 0

I was 4 or 5 years old.I was home sick and my mom was sleeping so I was trying on my sister's dress.and then the phone rang and could not get the zipper down and all most got colt but I loved it and sill do.

2007-04-09 22:22:11 · answer #6 · answered by Jenn F 3 · 0 0

It is called Boarding School and 300 very bored guys who happened to have a skirt, leggings, and a very tight top.

Gotta love eyeliner.

2007-04-09 18:40:39 · answer #7 · answered by wickedfan128 2 · 0 0

Oddly enough, after I got married, and I developed a fetish for womens clothes, especially wearing bras make me feel huggy.

2007-04-16 21:22:15 · answer #8 · answered by persnicady 3 · 0 0

11 years old. Tried on my sister's clothes and was instantly hooked.

2007-04-09 21:50:14 · answer #9 · answered by cd_aimee 3 · 0 0

well, being a girl, i could always wear boy clothes and be alright. so yeah, ever since i was old enough to pick my own clothes, it's been boy clothes.

2007-04-09 19:34:54 · answer #10 · answered by fear of the dark 5 · 0 0

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