Time Grew Short

Ohio River Pride from the
Jessie Hart Collection

I was just passing the age of sixty when I finally decided to retire my long unwanted male life and start anew as a transgender woman. Of course one of the main factors I faced when I decided a transition was the best and only way I go in life was my age. I wasn't getting younger. Since, all of the sudden, I was facing my mortality I felt it was time to make a decision on my gender issues.

Even still, with time catching up to me, I still had many decisions to consider when I looked at attempting a  major gender transition. Examples are the usual ones such as what was I going to tell my family and what was left of my friends all the way to what was I going to do about my finances and a job. On the other hand, I did have several benefits stemming from the life I had lived up to being sixty.

One of the main benefits I had was the fact I had spent nearly fifty years being a serious transvestite or cross dresser. During that time, I had plenty of occasions to leave my gender closet and experiment in a women's world. By the time I decided to completely transition (at least to living full time) I had managed to go through my second puberty clothing wise and began to dress to blend in with the world. Backtracking a bit, I don't think any transgender person ever gets a chance to transition completely until  passing away. Then their family must follow the trans person's wishes to be buried (or what ever) with the transgender person's chosen gender. Always a guessing game, sadly. Thinking of what was left of my future totally pushed me into getting started. I had no time to waste.

Since I had nearly completed the difficult task of learning the feminine arts of makeup and clothing, my biggest challenge was beginning to build a whole new person who could interact in the world as a transgender woman. As I worked on the process, I needed to learn to multi task. In other words, I needed to learn how to react to those casual observers of mine who may have initially thought I was a cis-woman. Then, there were all the others who knew I was transgender and may have reacted differently when they got to know me. The entire process was intimidating but exciting at the same time. My lack of male friends when I was sixty is well documented. I didn't have many to be concerned with because by that time of my life, they had nearly all passed away. So I was starting from scratch in the friend department. 

As time grew short, I found I needed more and more to relax and enjoy how my inner feminine person was reacting to her time to live.  She learned quickly how to react to other people and decide if she wanted to be friends or not. I also found a new level of respect I never felt as a man, probably because most other women knew I was being my authentic self and respected me for it. I was fortunate I had ultra supportive women such as my daughter and other very supportive women who helped me along when I started hormone replacement therapy in my early sixties.

Through it all I was humored when someone attempted to say they were more trans than I because I waited so long to transition. Even though I often think I should have crossed the gender frontier earlier in life, there were times in my male life I wouldn't give up for anything. The birth of my daughter is the primary example.  The rest of the time, I prefer to think I was just trying to make the best of an unfortunate gender situation. Finally, the pressure of attempting to live as two genders proved to be too much for me to handle. After much thought, I took the correct way out and chose to live as a fulltime transgender woman. I had put reality off long enough.   

Gender Escapism

Image from UnSplash and Let's go Together

 For most of the earlier years of my MtF gender transition I literally and figuratively tried to hide behind my skirts. As I was attempting to make my way through an unpleasant male existence, when nearly anything happened to me which I considered unpleasant, I resorted to thinking if I was feminine I could escape my problems. Little did I know, or consider at the time, girls/women had their own set of problems to deal with. 

Let's take dating for example. As I was very shy to begin with, asking any girl out was a huge problem for me. From that point forward I would have rather been the pursued not the pursuer and have someone ask me out instead. Of course it never happened. Another example was when I didn't make the cut for the junior varsity football team at the very small school I attended. When it happened I immediately wanted to go back home and try on my feminine clothes in front of the mirror. In addition, my top fantasy was how it would be to be one of the school's ultra pretty and popular cheerleaders. While at the same time not taking into the amount of work the girls would have to put in to do it.

It wasn't until years later when I realized how much my escapism hurt my life. Every time I ran to hide behind my skirts turned out to be a time when I had to learn to stand on my own two feet. Once I did, I finally began to build the courage to leave my male existence behind and begin a new life as a full time transgender woman. Essentially I was following through on what my second wife told me to do. Be man enough to be a woman. Sadly I wasn't able to accomplish what she told me until after she passed away and she was never able to meet the new woman I was destined to become. Since through much of our marriage I was intensely unhappy with my gender, I believe she would be happy I made it to a point where I could be satisfied with life. 

When I did "make it" to the other side of the gender border or frontier I discovered also the many faceted problems a woman has to go through to live. Cis-women are certainly born into the high maintenance gender. From everything such as child carrying and birthing all the way to just dealing with everyday appearances and emotions, women have to shoulder the burden of life.  It's no wonder cis-men say they don't understand women (or don't want to) because on a day to day basis they don't have to deal with lives often as difficult as women have to deal with. Which brings me to the point I make over and over again. Why would any man in their right mind leave an easier gender existence and attempt to live as a transgender woman. The answer is, and always will be is because we had to. We had no choice and needed to change how we lived our lives. Most certainly, the new gender grass was not always greener but we needed to try it out anyway because it all felt so natural.  Plus, the change just had to work to save our life. 

Gender escapism didn't work for me. Finally life caught up with me and taught me to stand up for my true self and live full time as a transgender woman. 

Was the Transition Risk Worth It?

Image from Sammie Chaffin
on UnSplash

 The answer to this question most likely depends on where you may be in your gender transition. If you are just beginning, the risks coming fast and furious these days may seem to be to much to handle. Until recently with the barrage of anti transgender political bills, I considered the era I transitioned in to have been more risky. Now I am not so sure.

As I remember, the biggest problems I faced were of my own doing such as my well documented fashion errors which led to me being rejected by the public. Once I conquered being able to present properly as a woman, I could then move on to other problems. The main one was the sudden possibility I could carve out a new relatively successful life in a feminine world. The main things which were holding me back were the extreme risks involved with following my gender dream. In my life up to that point I had achieved success in going against the odds and taking risks. The main example I can recall was when I was drafted during the ill-fated Vietnam War. Instead of serving the two year draft time, I chose the three year enlistment time and set out to see if any branch of the military offered anything close to my career in radio broadcasting. It turns out the Army did  and with the help of a US Congressman I was able to be accepted into the American Forces Radio and Television Service and then served in Thailand and Germany. You might say I was successful. 

As the years went by, I left the broadcasting business and entered the food service industry which was expanding rapidly. I was able to increase my income substantially and begin a love/hate relationship for the next thirty plus years.  The problem was, I became so adept running restaurants I was paid more handsomely for my efforts. Taking chances with my feminine life became more and more of a problem. The more successful I became in the male dominated world I was in, the more I lost if I suddenly left it. I tried desperately to exist in both gender worlds to no avail. The process became so apparent, the more I did in my new and exciting feminine the more natural I felt. The more natural I felt, the easier it became to take on the new risks I was experiencing even though I was overall terrified about the path my life was taking. 

I never attempt to speak (or write) for anyone else but for me the risk I took to stop my male life and rebuild a new one as a transgender woman was worth it. Especially when I began hormone replacement therapy which I understand has a new name these days. Regardless I look at the point when I started HRT as the point of no return for my old unwanted male self. I was ready to take the final risk to begin a new natural gender life. If, on the other hand if you are still in your gender closet, don't despair because you never know when doors may open for you to explore the world. One never can tell the future and often destiny can lead in unexpected directions. 

Sadly, though, the longer we wait, the more risks we transgender women or trans men have to take when we transition. We develop family, friends and employment to navigate. When the risk became no choice as it did in my case, it was time to take another key step in my transgender transition, throw away all my male clothes, become femininized by the hormones  and start a new life.