Starting All Over Again as a Trans Woman

JJ Hart

With all the environmental global warming disasters we have going on in the world today, there are many people forced to start their lives over. My heartfelt sympathy goes out to all of you who have lost a significant part of your lives to weather-related incidents.

On the other hand, transgender women and transgender men have a head start on most people because we have become skilled in stopping our lives and starting all over again. In my case, I put it off until my mid fifties to start all over again and leave my male past behind me. The only thing I really did was build up too much male baggage I had to figure out what to do with.

I had a long-term marriage to a wife who was completely against any thoughts of me transitioning into a woman, a small but secure family, a vintage brick house I was restoring and a good job to consider losing. Unlike a weather related “hand of god” experience, I was bringing down the demise of my male life completely on my own. Without the help of anyone else. So, it would be my burden to carry around if anything went wrong with me crossing the gender border and following an extreme male to female femininization program which would eventually include HRT gender affirming hormones.

The only thing I did know was I was off to a good start as I slowly refined my makeup and clothing arts as a very serious cross-dresser who always had the suspicion that more than cross-dressing was in my future. Being more than a cross-dresser was like dangling a carrot in front of a horse to get it to move, I just had to have the confidence to tear down what I built and start all over. Any setbacks I encountered when I went out in public for the first time would always destroy the frail confidence, I had built up in myself over time and sent me back to my closet to try to figure out what I was doing wrong. How hard could it be?

I found out over my early years that “it” could be very hard as I struggled to get out of my closet and into the world. For the most part, it seemed I had bitten off more than I could chew when I began to get close to the gender border and had to think of all the white male privileges I would have to give up if my urge to transition did not change. Not only did it not change, but it also strengthened into a powerful force that I thought of every spare moment of the day and even some nights when I dreamed. It was always extra punishment when I had to wake up from being an attractive woman and go back to my boring and unwanted male world. Still, I had no alternative but to keep pushing towards a transfeminine goal I never knew if I could reach.

To my surprise, I went through other major and minor transitions as I made my way from cross-dresser to the transgender terminology. As I became more skilled at blending in with the world of ciswomen around me, mentally I slowly shifted back to my old thoughts that I wanted to be more than a man who looked like a woman. I wanted to feel as close as I could to feeling like I belonged behind the gender curtain and be allowed into the girls’ club full-time. All my surprises led me to a place where I could finally flourish as a trans woman. If I could decide what I was willing to give up getting there. When the time came to decide, would I be willing to push all my chips into the middle of the table and decide to go all the way, or once again, slink back again to my closet. Or I could relate my life to being one big “Monopoly” game where I was always ready to take another chance and buy another feminine property.

I know all of this sounds like sort of a word salad fantasy until reality set in for me. In my haste to seek out the meaning of a feminine existence for me, I had started to build up the basics I would need to keep building a new and exciting life I never thought I could get to. But there I was having to decide what I was going to try to keep of my old male life as I tore it all down and built a new one. I was very one dimensional in my life with my hobbies and interests so in that sense, I did not have much to get rid of. The one interest I hoped I could keep was my interest in sports and always figured it might help me if I was ever involved with a man but never dreamed my former male life in sports could mesh so well with the ciswomen I met.

Before I knew it, I was joining woman-friends in sports bars drinking beer and debating our favorite teams. I saved one piece of male baggage but at the same time, others had to go. As I write about often, I lost my unapproving wife and several male friends to death in a short period of time. When they left me, I realized how difficult it was for me to make true male friends. As I started to transition more, I began to understand why. Down deep, I was never interacting with other men as a man but rather as the trans woman I truly was. All of the pieces of the puzzle of my life were finally starting to come together, and I was seeing the big picture of what my denial of myself had cost me over all those years. I came away thinking how I could miss something that was that simple.

One thing was for sure, thanks to the HRT hormones and the relationship I was building with my future wife Liz, nothing was standing in my way on my gender path. Liz was the opposite of my second wife and told me she had never seen anything but female in me anyhow. I certainly was not one to argue and gave away all my male clothes to charity so I could help all those thrift stores which had helped me in the past.

I was more than ready to start all over again.

Thank you so much for taking your time to join me in my gender travels. Any comments are always appreciated.