My Biography, I hope you like it.

    My story is not unlike the thousands of other stories I’ve read online. I actually have a photo of me as a baby dressed in my sister’s hat. As a 3 year old, one summer, an older boy and I decided to put nail polish on our nails. We had a ball until we discovered that it wouldn’t come off if we tried to rub it off. We had to undergo the humiliation of running to our mothers to have it removed. Our mothers seemed to have a lot of fun with that. And, I have memories of me as a 4 year old boy joining my sister and her friends in putting on lipstick. This continued for many years. My earliest friend was a girl, Eileen. I preferred her to her younger brother who seemed even then to be immature. She was a year older than I but we got along really well.

    I tended to be a bit of a loner at school but had a number of male friends. Although I had this increasing desire to dress up as a girl, I lacked the courage to openly discuss this with anyone. I remember a Halloween when I was about 7 or 8. My mother, who hadn’t ever discussed this with me at all, suddenly and whimsically suggested that I wear “my” blue dress to the party. I was floored by the suggestion. Of course, I had no such blue dress and I had no idea where she had gotten the idea (in retrospect, it had to be from my sister) that I might even be interested in doing such a thing. She and my sister had a good laugh but were actually very interested in the idea. I seriously considered it but didn’t know how much taunting I might be in for if I did dress up as a girl. Ultimately, I decided to go as a cowboy but reserved the right to come back home and dress as a girl if I felt safe enough. At the party, a rather swishy boy had come all dressed up as a girl and he was subjected to merciless taunts throughout the party with boys frequently picking up his skirt to show that he was wearing panties as well. Needless to say, I felt vindicated in not dressing up in public.

     After that, my mother would frequently suggest that I dress up just for her. She said she had a friend whose son would dress up for her and they had a marvelous time together. This was the same son who had put on the nail polish with me and who ultimately became an actor. For some inexplicable reason, I felt humiliated by the suggestion even though a very large part of me was dying to do just that. I felt it was a point of pride that I not do this with my mother. At the same time, I would make believe I had a skirt on while wearing a large towel around my waist or make believe I had long hair under a towel around my head. My fantasy play with both boy and girl friends frequently revolved around dressing as a girl. I was crazy about the Eddie Cantor Show because he had a segment every week with him and George Jessel dressed as women going shopping, etc. I had a female cousin who I would role play with all the time as woman a la Eddie Cantor. I never missed Milton Berle’s drag performances even though I felt he was over the top. A male friend once enthralled me with his telling me that he went to a masquerade party as a girl, fully dressed with makeup and nail polish, and he won a bottle of nail polish as the prize for the prettiest girl.

     I had been fortunate enough to be sufficiently well-coordinated to be pretty adept at sports so that I didn’t have to go through the taunting lots of my less sports-oriented TG friends had to experience. Nevertheless, it was apparent to some that I wasn’t at all the macho type of sportsman. In 5^th grade (all boys’ school), for instance, I was selected by my teacher to play the role of a woman in a play. I had no idea how that seemed to make sense to him but it took lots of persuasion on my part to be freed of that obligation.

     The bottom line seemed to be that I would preferentially like to fantasize that I could be a woman and dress up in my mother’s clothes whenever I could, but I would go to great lengths not to do it in public. I would always be very careful when dressing in my mother’s clothes to note where everything was stored so I could replace everything just right. Although I was never caught, I had some near misses when my parents came home earlier than expected.

    In retrospect, although I’ve never raised the subject with my sister, I have come to realize that my mother must have known a great deal about my crossdressing all along. It is one of my major regrets that I never had the courage to confront this and perhaps have experienced crossdressing with my mother’s full support. Unfortunately, she passed away when I was 19.

    Perhaps because I was faced with her possible death at a young age, I started dressing more and went to the Apollo to see the Jewel Box Revue ( a drag show). Although I hadn’t ever been able to masturbate as my friends had all along, I experienced my first ejaculation while wearing my mother’s girdle. I was 18 years old and was shocked at this revelation. I continued to dress fully throughout my mother’s illness and after she passed away. In some way, it made me feel closer to her than ever before. I was devastated by her death and almost ruined my career opportunities by its impact on my studies. But, with the help of some very understanding faculty members at college, I was able to more than recoup.

(to be continued)