Saturday, August 15, 2026

I Was Risking it All

 

Image from Leo Visions
on UnSplash.

In many ways this post is an extension of yesterday's explanation of me never really having a plan b as I traveled up and along my gender path to transgender womanhood. The essence of what I wrote was I did not have a real plan if suddenly it was evident I was not going to make it to my dream.

I was taught to be a dreamer by the unrealistic expectations my parents put on me. Whatever I did was never good enough and often sent me back to hide in my dresses, hose, and makeup. The only place that my impossible dream of being allowed to be feminine could become a reality. If only for a short time. I don’t know exactly why, but the gender dream I was pursuing so well was the only dream I wanted to become a reality as I did just enough to have good grades in school and played just enough sports to keep the bullies away.

Cross-dressing was always a risk because back in those days (the 1950’s and early 1960’s) gender issues were considered to be mental health problems, and I knew that did not describe me. On the other hand, I did not want an impromptu visit to a psychiatrist to tell me about myself and how I should be treated. Fortunately, that mental health visit never happened as I continued to risk my existence on some sort of a high-wire act which if I ever fell, life as I knew it would fall with me.

Of course, as it always does, life became much more complex as the years flew by. As my cross-dressing became more presentable, at the same time, I had college demands and a military service I never asked for to deal with during the Vietnam War years. All this time, I was learning what it meant to risk it all in my life and somehow still succeed. As even though my gender issues were put on hold for a long three years, I learned valuable lessons from the Army on how to attempt to deal with my dream which was on hold. At the least, I learned from the military how to deal with a structure I had never had before as well as other issues that would take another blog post to deal with.

When I was discharged from the Army, I gained my first and only child and my life became even more complex. What could I do with a child to deal with if I wanted to risk it all to run away and live a transfeminine life. Dealing with everything else for me became easy when I had a family to provide for. Any alternate plans I had for my future were delayed again along with any hope of ever making it to my dreams.

What suddenly came along to help me was when the internet took hold of the world and I was introduced to people just like me I could reach out to and even meet. All because of the first in home computer my second wife and I purchased. By participating in the first chat rooms of the time, I had my first taste of what it meant to be a transgender woman and not a parttime cross-dresser as well as sampling my many layers of the gender spectrum I never knew existed. The one big thing the computer did for me was that it taught me how badly I wanted to test out the new world I had discovered for myself and see where it took me.

I also learned quickly that it was easier said than done. Mainly because when I left my safe closet mirror and jumped into the harsh reality of being a trans woman in the world was not going to be as easy as I thought. I needed to quit dreaming of what I thought I should look like and begin to expend all my time and money working on how to survive in a world where ciswomen run the show. Sometimes up front and most of the time behind the scenes which I came to call the gender curtain. I found out the hard way, that to not be rejected in my quest to make it behind the curtain I would have to eventually risk it all in search of the new, exciting world I wanted to live in.

I am not a poker player at all, but I knew I would have to push all my chips to the center of the table to see if I could ever win my goal. The problem remained that my male side was still acquiring more chips with his new more demanding job. Here I was stuck between two genders trying to rule each other and the male side was materialistic, and the female side was more natural and felt like I was doing the right thing for the first time in my life. All the turmoil resulted in was destroying my already frail mental gender spectrum health. It tore me up as I had to constantly be aware of which gender I was on any given day.

As I said, eventually my feminine side won out as I chose feeling more natural in the world than I ever had as a man. He had been reduced to a shell of his former self by being able to shed his male privileges he earned but never wanted. In its place I gained the greatest female privilege of all…the freedom to experience the world as a trans woman myself. It took a while but all the dark downtimes I experienced on my bumpy gender path made me a more resilient trans woman with a unique understanding of both sides on the main gender binary.

I cannot imagine what would have happened if I had lost that gender poker game so long ago because I was living such a miserable life. Plan a was to always live as close as I could to a woman. It took me decades of life (5) to get there, but I made it.

 

No comments:

I Was Risking it All

  Image from Leo Visions on UnSplash. In many ways this post is an extension of yesterday's explanation of me never really having a plan...