I was born in Washington DC as David, and we lived in the Maryland suburbs at the time. My first recollection of crossdressing was trying on my older sister's dresses when I was alone in the house. I'm not sure when this was, but I guess that I was probably 6th to 8th grade. My mother came home early one day and caught me. That is my first recollection, but I also remember that when she caught me was not my first time trying on my sister's dresses. I had also tried on my mother's dresses and skirts but had found that my sister's fit better. I remember my mother being disappointed, and phrases such as "some boys don't have older sisters and so they wear their mother's clothes" and "I don't want to tell her about this".
That was the only time that I was 'caught', and if I did try on my sister's clothes later, I at least do not remember.
When I went to college, my sophomore and junior years I was in a single, so I had some dresses that I would wear occasionally in the privacy of my room. After my junior year I then transferred schools and lived at home, and again (or still!) had some dresses that I would wear when alone in the house. I also added some women's shoes to my collection.
During this time I was member of a square dance club, and after a while got to where I would at times switch with my partner and dance the women's role while she danced the men's role. I didn't think of it in gender terms at the time; just having fun at the dance. I was the only guy who did the switch, though, and do remember at least two girls I would do this with. I also remember when one of the girls said that they should get a skirt for me, and I told her (mock angry) "Boy, you've got nerve!" then whispering with a smile to her friend "I've get a 32" waist". I still laugh just thinking about that!
After finishing my degree, I moved into my own apartment about 1 1/2 hours away, and would still wear dresses at home occasionally. After over 5 years alone, I moved back home, then met the woman who would later become my wife. Before the wedding, I told her, oh by the way, I wear dresses at times. She said that she wasn't really into it, so, when after that, I moved into an apartment with her, I threw away all my dresses and shoes.
After some number of years, (I don't remember exactly, but it may have been 2-4) I asked her again about my wearing dresses, and she said that it would be fine. Since then I started again buying skirts and dresses and wearing them at home when it was just my wife and me.
And it stayed that way for a number of years, until March or April of 2000.
This page last updated 12 February 2002
URL: http://www.geocities.com/darlene_20832/bioearly.html