I was a child of the early ’60s. Back then, the world was a much different place, and I learned quickly that I did not fit in. I thought I was a girl, and my parents had wanted a boy. I believed that the stretch marks under my scrotum were from having my boyhood sown on.
My first encounter with crossdressing was around age five when I tried on a pair of my older sister’s panties. The feeling was unexplainable. I would beg my sister to let me play with her and her girlfriends, with no luck. I was very girl-like when it came to playground activities. Eventually, I learned to play like other boys in order to make friends, even joining football, baseball, and wrestling teams in Jr. and Senior High School. I never got to play.
I think my mom knew early on that I was different. She taught me to always keep my shoulders back, brush back my eyebrows, keep my fingernails clean and trimmed, and how to cook, iron, and sew. Unlike my friends and classmates, I always liked to dress up for school and church. Kids would make fun of me and being good at school as well as the teacher’s pet didn’t help.
In junior high school, I hung out with a group of girls who all liked me because I understood them and would help them with their boy problems. Of course, I always had a girlfriend myself, since the 4th grade, and loved hanging out with them and their moms.
I had encounters with older boys and men from time to time, but my realization was that I was not gay, enjoying the sexual activity. I married and had two beautiful daughters with my first wife. Trying to be all that I could be, I joined the Army. At first, I was happily dressing up as a woman for Halloween. I tried introducing a third into our sex life and would have fantasies about being the other woman. We eventually separated, then divorced after 14 years. We are still friends today.
I crossdressed at home for about a year, and when I tried to introduce it to my female roommate, she had a negative reaction. I married for the second time, hopefully putting all this nonsense behind me. Seven years into the marriage, I packed up the car and told her I thought I might be gay and drove to Key West. Back home in a week, I didn’t know what my feelings were all about. A year later, she told me to move out of our house just after Christmas.
I did some dating, looking for a woman that would fulfill my fantasy. I concluded it would be impossible to find someone not knowing what I really wanted. Not wanting to be alone, I married my wife of 20 years. Two years ago, we started dressing up in Victorian-era to early 1900s costumes and going out to wine tastings and nightclubs. It was wonderful! Then we went to NOLA for Madi Gras 2022, and girls, did I LOVE that!
It was the beginning of me buying, without her knowing, shoes, clothing, lingerie… When she returned from a six-week trip last June, I told her I liked crossdressing. It has been a bumpy road since, to say the least. We took a cruise back in October for two weeks and I did dress-up most of the time, with mixed reactions. Since then, I have been working on MTF, and HRT with my Drs., therapist, and counselors. Not knowing at my age and with health conditions, if I could even consider it. I didn’t want to put my wife through any more drama until I was sure it was possible. Leaving on vacation to Europe, I received word on June 6th; I start on the estrogen patch and planned to talk with her when the time was right. She saw the patch, and I told her about a week into a three-week vacation. She is not happy that I’ve kept it from her, even though I had good intentions. I should have talked to her about it.
Now I find myself at a crossroads with my marriage, my job, and my community. Do I come out to the world and be the woman I’ve always wanted to be? Potentially lose all that I have built or continue to hide my identity and save everyone else from the heartache.