“Let’s start at the very beginning”, in the words of Julie Andrews, “it’s a very good place to start”. So how did I end up as a 39 year-old who has thrown their whole life into upheaval in order to transition to living as female? How did I not determine this sooner? Why transition now? Did I always know I was a woman? It’s taken me some time and a lot of psycho-therapy to find the answers to these questions but let me dig right in.
As I look back now, the reality is I always knew something was off. As a kindergartner in a Catholic school, I can remember being curious and a little jealous of the plaid jumpers and tights that the girls in my class got to wear. Often times I wanted to play with the girls but was shunned because I was a boy. I learned very quickly in that social setting that any talk of doing things the girls do was shameful. I dared never share the fact that I wished I could wear their clothes and play their games. Shame and fear taught me to bury my feelings and just be a boy.
So that’s what I did all through elementary school. I played sports, I hung out with the other boys, I tried to fit in. I struggled often. I got into fights at school and was a regular visitor in the principal’s office. I had a hard time making many friends other than just a couple key friends. As we got closer to high school, I started to figure out that I had a much easier time understanding and talking to girls than I did boys.
My cross dressing started while I was in elementary school as well. I can still vividly remember the first time, while playing with my sisters, that they had me wear pantyhose and a pair of my mothers sandals. The feeling was exotic and exhilarating. However, I dare not tell anyone. I started cross-dressing in private. I had ample opportunity when I would be home alone to steal my mother’s or my sisters’ clothes and dress up. As puberty started to settle in, my activities took on a more sexual tone and I started to look at my cross-dressing as more of a fetish.
It was in my middle-school years when I remember Jerry Springer and Maury Povich had very popular daytime talk shows. I can remember seeing many episodes where they had transsexual guests revealing themselves to lovers or family members. Secretly, I’d fantasize about what it would be like to become a woman. Yet again however, these were shameful thoughts that I needed to tuck away and ignore. While it was a fun fantasy, I just “knew” I wasn’t like them. They were portrayed as freaks and I was not a freak. So add in more denial.
As I entered high school, things didn’t get better. In a much larger setting, I still had all the awkwardness that I had experienced in elementary school. I didn’t make many male friends, but I was great at getting into the “friend zone” with the girls. My cross-dressing continued in private while in public I tried like hell to fit in as a guy. I was bullied, I was picked on, I got into a few fights and I tried to fit in with any crowd that I could. It just didn’t work. In my freshmen year, I met this cute little cheerleader who would later become my wife. After being friends and her switching to a different school, we started dating in our sophomore year. He was this cheerleader, a girl who had all the popular friends, dating me. The scrawny geek who was picked on and tormented. Truly, the geek got the girl!! I did everything I could to try and be more of a man for her, even if I didn’t really understand how.
To be continued…..