I Failed my Gender Assignment

Vintage Edition of
Transvestia Magazine

 My initial gender assignment was very simple. I was born a boy, now be one. The problem quickly became I was failing the assignment and I just didn't want to be the gender which was assigned to me. 

Instead of following all of the basic rules I was given about being male, sooner more than later I began to realize something was wrong and essentially I had no choice but to follow the rules. As they were presented to me. My parents were members of the "greatest generation" who survived a great economic depression and a world war.  They were well versed in taking what was presented to them and making the best of it. The same was expected from me. I had no way out when it came to my gender issues. I was alone with my problems. 

In response I did the best I could. I participated in sports and did my best to present myself as a so called "normal" boy. While I was doing it, I also was doing my best to use my limited funds to accumulate a small collection of makeup and feminine clothes which freed me up from helping myself to my Mom's belongings. Of course at the time I was outgrowing my Mom in all the size categories, so it was good to finally go out on my own when I could. I guess you could say, this was the first time I actually passed my gender assignment, in my chosen dream world of being feminine. 

At the same time, I learned the male so called attributes of being emotionally distant and keeping my feelings bottled up. I would carry those with me until I was able to more completely transition my gender.  I was able to not fail this part of my gender exam. In many ways, in order to receive a pass or fail grade in either gender, I needed to wait for the world to catch up to me. Since I was a part of the pre-internet generation, information of any kind was very limited. In fact, I was completely isolated in my closet until I learned of "Virginia Prince" and her "Transvestia" publication. I was so relieved when I found I wasn't alone in the world and there were other so called transvestites in the world and some even met for mixers in cities close enough for me to attend. 

Once I did attend, my path to a different gender assignment became clearer. I was able to interact with others dealing with the same gender issues I was dealing with  and come up with a new plan for my life. It was about this time the transgender word became popular and I strongly believed it fit me. It was becoming increasingly evident I needed to take another gender exam. I was failing my initial male assignment and wanted so badly to attempt taking the new exciting feminine assignment or exam. Before I was able to, it turned out I had a lot more studying to do. Being a woman was a lot more than just looking like one. I can compare the process to higher education. Just being able to blend and mix in with the public as a transgender woman was similar to having an undergraduate degree. Then being able to communicate with other women one on one was the equivalent to obtaining a masters degree and so on.

Finally I accepted the fact I had failed my male assignment completely. No matter how hard I tried to succeed as a man, the whole process seemed to be an empty pursuit. Even though I was relatively successful in obtaining male privilege, I found I didn't want it. On the other hand, attempting to go as far as I could with a feminine gender assignment proved to be the answer to all my gender issues. Why? Primarily because the whole process felt so natural to me.

   

A Need or a Want

 

Image Courtesy Alexis Fauvet
on UnSplash

Beware, this post deals with semantics. Perhaps I should have put a "TW" or trigger warning in first. Semantics are difficult to deal with due to tendencies to paint problems or solutions with a broad stroke of a brush.

What I am getting to, is the question of being transgender  more of a need or a want. I have a tendency to think it is a need more than a want. Why? Because to me a want is more of a choice which anti transgender bigots who are trying to take our rights away often try to condemn us with. Down deep we transgender women and trans men know we never had a choice. Our lives were always destined to go down an often long and bumpy gender path to freedom. In other words, destiny equaled more of a need than a want.

As I look at the process, I can compare it also to the need to eat. Naturally we all have to eat to survive and that is exactly how I feel about my gender journey. The more I progressed down the path, the more I needed to keep going. Long ago in my journey did I stop thinking I was cross dressing simply because I wanted to. I learned the hard way I was so much more than a man who had an extra "hobby" which wasn't golf. Instead I was obsessed with the latest women's fashions and imagining how I would look in them. More and more, even though my wife knew I was a transvestite, I snuck away in our marriage. Essentially I was cheating on her with another woman who happened to be me. I always tried to live an honest life so lying to the one person I loved the most tore me up.

Through all the cheating I was doing, I never gave much thought to what was going on. Most certainly the whole gender process I was in was more of a need than a want. I needed to keep pursuing a feminine lifestyle which I had seen other transgender women around me try to do and were successful at doing. Watching and learning from them helped me to live a new life which was slowly but surely taking over my old unwanted male existence. No matter how I tried to tell myself I didn't want to be a fulltime woman and even with all the purges I went through, I kept coming back to the same place. I needed to live a feminine lifestyle.   

The rest of the story I write about often. My second wife tragically passed away from a major heart attack, leaving me so alone in the world. I was able to fall back to the other woman in my life who I needed also. My feminine strong soul took over and with the key help of several dear friends, I was able to undertake my key transition into a lifestyle I had only dreamed of. From there I never looked back. Secure in the fact my gender desires were more of a need than a want.

What I Intended to Be

Image from Jen Theodore
on UnSplash

Early on in my life, I was all in on pretending to be someone I thought I was not. (a girl) I was reinforced by all the lonely times I spent in front of an admiring mirror which was telling me I looked wonderful as a girl. All along, the mirror was just reinforcing what I was pretending to be. Feminine (or what I perceived it to be) dominated my free time thinking.  I wrote "what I perceived femininity to be" because as life went by and I acquired more experience cross dressing and/or being a transvestite. I was so protected back in those days, I didn't even have the time or access to really consider what either term meant. In either case, I discovered both were just labels anyhow.

The whole gender process I went through ended up taking me nearly a half a century to go through which sounds intimidating. The trip also was very laden with various ups and downs which I revisit frequently. I do it in the hope others who are considering such a venture can learn from my successes or failures. Similar to everything else in life, we have to learn from our failures and move on until we can finally experience the successes. I experienced more failures than successes before I finally  learned to present as well as I could as a woman in public. When I did, I needed to settle on one look and build my new self from it. 

From there I was able to move away from any thinking I was moving away from pretending and moving increasingly towards a life to be lived as it was intended to be. The main reason was the process felt so natural. Even though for the most part I was terrified to give up my old male life. Each step I took as a novice transgender woman proved I was on the right gender path. On the path I was able to carve out my own safe places to go to. I started out in gay venues. In which I quickly rejected for several reasons. The main one was I did not want to be mistaken for or treated as a drag queen. From that point I started to go to a few upscale bar/tavern venues similar to what I was used to managing in my restaurant days. I had one main positive going for me in that I knew the venues were primary revenue driven. And, if I did not cause any trouble and tipped well, I could survive if I did the best I could to dress to blend. I became a regular bar fly and was able to build from there. 

Again, the more I quit pretending to be a woman and started to believe I was one...transgender or not, the better I did. The new world I was in provided me many challenges to move forward into a feminine world I had only dreamed of. The whole process led me to quit pretending all together I was ever a male in the world and onward into a dream world of being a woman on my own terms. Sure I faced the haters who said I could never be a woman because I could never bear children to which I replied what about the cis women who for whatever reason can't have children either. For the most part, I never heard from them again.

As it turned out, life started all over for me once I made it to my early sixties and I was able to start all over and live my life as it was always intended to do.