Supporting Casts


Girls Night Out. I am on the Left.
From the Jessie Hart Archives

One aspect of my gender journey, I don't mention enough is the importance of the supporting cast I had around me to help me along.

They clearly helped me during the times of my life when I was down and almost out when it came to me going any farther as a transgender woman. A prime example was when I started gender affirming hormones and was wondering if it was the right move to make. By just being a part of my life and understanding what I was going through brought about a significant need for moral support. Another example was when I began having hot flashes and my women friends (cis-gender) just smiled and said welcome to their world. Which is exactly where I wanted to be. 

Over the years, there was only one woman who held my gender issues against me. She was my first fiancĂ© who in the past, one time cross dressed me head to toe as a woman. The whole process turned out to be a bittersweet experience. For the first time in my life I had tried to share my deepest secret with another person and turned out to be less than impressed with the entire outcome. When she had finished with my makeup, I saw no real improvement over my efforts which ended any ideas I had that women had an edge over cross dressers when it came to makeup applications. So, the sweet part was limited and doomed to fail to begin with. The bitter part came later on when my fiancĂ© broke up with me after I refused to say I was gay in order to not be drafted into the military during the Vietnam War. Lesson learned and I went back into my deep dark gender closet for years until I met my first wife. Even though she always knew I was a cross dresser or transvestite, she never made a big deal about it. 

Around that time of my life the biggest support I received ironically came from a man. A stranger who was doing makeovers at a cross dresser mixer I attended. I put on my big girl panties, removed all my makeup and let this stranger work his makeup magic on my face. When he was finished, I couldn't believe the transformation. Plus, I was actually able to understand and redo the makeup steps and repeat them. The entire process takes me to my experiences with my second wife. Similar to my first wife, she knew I was a transvestite from day one in our marriage and even supported an extent. Keep in mind, we were married for twenty five years and during this time, I was slowly transitioning more and more into the transgender woman I am today. Before my wife's untimely death, we had numerous fights over my desire to be a woman and begin gender affirming hormones. Her stance until the end was she didn't sign up to be with another woman. To make matters worse, I don't think she ever liked my inner feminine self and the two women battled continually.

After she passed on, it took me a few years for me to recover from the shock and get on with my life. One positive I carried with me was how affirming the presence of my feminine side turned out to be. As it turned out, destiny led me to other groups of women who essentially adopted me into their tribes and helped me to flourish. 

I can never say enough how much I learned from all our girls nights out together. Without all of them I can never imagine how much longer and which direction my transgender transition would have taken.