He Wants to Be She
It did not start this way, but I can no longer ignore feelings that I want to be a woman. If I had to guess, I'd say that this all started at puberty when, for reasons I was not sure of, I started sneaking into my older sister's room and putting on her nighties, bras, and panties. This went on throughout my teen years and I am surprised I never was caught. Throughout my teens, twenties and even into my thirties, I was attracted to women and having sex with women. When I moved out of my parent's home around age twenty, I lived with a woman and one day (I believe it was a Saturday) while she was at work, I found myself in our walk-in-closet staring at her clothes, especially her dresses. I was drawn to put her clothes on and it was not long before I was wearing her dresses, panties, bras, and heels (she wore a size 10, which fit me) around our apartment while she was out. I remember that I'd leave the patio blinds open because the girl across the courtyard would watch me from her bedroom while wearing only a bra and panty. Also, I began going out in public dressed in her clothes. Typically, it only involved driving around, though it evolved into situations where I would go into women's clothing stores and businesses. At that time for some reason, I would get excited if other women saw me dressed that way. This conduct continued with other women I dated. Eventually, I started experimenting with makeup, jewelry, and wigs, and going all the way with dressing as and looking like a woman. I started having fantasies about being in the female's role for men and about buying female toys to experiment with. Well, one night while I was all dressed up and out as a female, a guy pulled up next to me in a parking lot and he started talking to me. One thing led to another and he asked me if I would talk to him in his car; I agreed. After getting into his car, within a very short time, it was clear that he wanted to do much more than just talk. I remember feeling really nervous though I could not leave. What he was doing was making me very excited and I could not help but stare at what he was doing. He could sense that I was unable to look away and interested, and he put his right arm around my shoulder and sort of pulled me over to him. After we finished, I jumped out of his car and drove away quickly thinking that I'd never do that again. However, about three weeks later, I could not help thinking about it and what I did, and especially how much I wanted to do it again. I continued to date women and even got engaged for a short period of time, but after that ended I focused primarily on dressing up, going out, and having sex with men. When I do, it is always with me in the female's role, and the men must treat me just like I am the woman. I've tried stopping and I have really struggled with this and these feelings for a very long time; and honestly, to this day, I still do. Few know this about me because I carry the guy thing off well, but the truth is I struggle with thoughts of wanting to dress up, be with men, and be a woman. In fact, most mornings, even though I say I won't when I go to sleep, I cannot help but start my day by wearing panties, a bra, heels, and playing with one of my female toys. When it is over, I usually feel bad, but the feelings return rather quickly. When I was younger, I'd go weeks and even months before the feelings would return and take over. Now, they seem to control my thoughts and actions on a daily basis. I even started a Facebook page to sort of come out, listing myself as the female I want to be; or, at least think I want to be. Part of me gets really angry and upset when I think of all the time I've wasted already not acting on these feelings, and especially in not going forward with transforming to a woman. I could have enjoyed my younger years as a female and now it's frustrating to think of how much time I let go by. Also, I've done a good job hiding this from my family and friends. There are only a very few who suspect, and even less that know I've actually dressed up and have gone out as a woman. It is very frustrating though. So that's my secret confession.
— Gerald, 44