First Time

by Juana Smith

"When was the first time you ever cross-dressed?

As I interviewed the following people realized how important it is to have them define what they mean by "first time to crossdress," because everyone has a different way of defining what a specific first time event is, including "crossdressing."

I began with the idea that the first time one crossdressed was the first time one put on even a single piece of attire belonging to the opposite sex. While Lee's account concurs with my perception, Paula and Pauli offer alternative definitions.

Well, it's the degree of crossdressing that bothers me about answering that question, because I actually borrowed my mother's underwear as a teenager, and actually wore it.

However, the first time I actually did full drag, got on a dress, undergarments, wig, makeup, and so on, was after I had finished a Ph.D. and was teaching. That was about forty years ago. Although it bothered my wife, she helped with some of the transformation. I remember that after I was dressed I felt exhilarated, I enjoyed doing it, and wanted to do it some more. I enjoyed feeling that I looked female. I don't think I did, particularly, but I was dressed well enough that I could have imagined that I did. Although I knew that society wouldn't accept it, I felt it was appropriate for me to dress as a female. I felt that in a certain sense I'm a female.

Crossdressing was something that I wanted to do, and continue to do. If it weren't in many ways totally impractical, I would probably dress female entirely, I could certainly go a long time dressed that way.

Pauli, a soft-spoken individual, begins her experience of crossdressing when she was 5 or 6 years old. I never thought of myself as a little girl in those days, but when I was 5 or 6, probably closer to 5, my sister, who was 13 years older than I, married and moved out of the house. I was given her room and she had left a lot of things behind. A lot of the furnishings were left behind, like a real frilly dresser, with a mirror, things like that. There was lots of her clothing in the closet, or maybe it was in the chest of drawers.

I remember a little suit, a pink suit. I remember putting it on. That was probably the first thing I tried on, a skirt and jacket When I tried it on, it seemed really natural to me, it made sense. It was kind of exciting. It's always been. I've kept doing it.

Lee, an attractive Asian, offers us a final story about her first time to cross dress.

I remember that when I was in grammar school I used to go home for lunch. Both my parents worked, so there was no one home during the day, so I could go through my mom's stuff.

When I reached the sixth grade I really started dressing a lot as far as putting on her lingerie and stuff under my clothing and going back to grammar school like that. In my mind, that was when I started crossdressing. When it became sexually stimulating. In the fifth or sixth grade.

I mean, I wanted to do it more and more because I received pleasurable feelings. Regardless of whether I was fully or partially dressed. It was always difficult to be fully dressed at home. But I would sneak in and get a panty, girdle, slip or something and wear those under my own clothing. That was when I first became aware that it was more than just an experiment. It was exciting to do.

Just write your true story about the first time you knew you were transgender or some other important "first" in your life as a transgender person. Email it to Cindy. Cynthia Smith edits the stories and will be in contact with you. Drop us a line!