Wednesday, April 10, 2024

Close Encounters of the Transgender Kind


Image from the 
Jessie Hart Archives.

Very early in my life, similar to so many of you, I suffered many close calls when it came to being caught in my feminine clothes by my younger brother or worse yet my parents. 

As with most inquisitive younger brothers, if I was out of his sight for any length of time, he wondered what exactly was going on. To make matters worse, we were just a couple of grades apart at the same school, so we rode the same bus home and arrived at the same time. Leaving me very little time to cross dress and admire myself. I even had to hide out in the woods when the weather was good to dress up.

My parents were partially a different story. My Dad was a banker and Mom was a high school teacher, so they arrived home usually in time to sit down to dinner. If you remember those days. My point being, seemingly for weeks at a time I couldn't find a way to explore my gender closet at all and the pressure to do it just increased to the point of no return. Which meant I needed to take risks. We had two bathrooms in our house and sometimes I could barricade myself into the one which contained most of my Mom's makeup. When I combined her makeup with mine, I had plenty to experiment with. 

On the exceedingly rare days I was left all alone, I went all out. Even to the point of being able somehow to get away with shaving my legs. I was completely in love with how wonderful the air felt on my freshly shaven legs when I took the chance to walk to the mailbox which was some distance away. No matter how good I thought I looked, the biggest problem I had was with my hair. In those days, I was stuck with either the ultra short burr haircut my Dad had or the equally as bad crew cut. A wig of any kind to me in those days just seemed like the impossible dream and it wasn't until my college years when I could afford to buy a nice wig I cherished for years. I even hid it, as well as other cross dressing necessities away when I went away to the Army. Hoping they would not be discovered. They weren't. 

Even with all my precautions, I still ran into the times when I had to hurriedly wipe the makeup off my face and change my clothes when my parents came home early. I don't know how but I somehow survived without a gender confrontation which would have been a disaster. At the time, I thought when I became older I would have more control over my cross dressing desires and life would be better. In no way did I feel as if all of the sudden I would wake up with no gender dysphoria and life would be much better. On the other hand I still felt I would not have to hide my true self to others. To compensate, I developed a very macho exterior self and avoided making very many friends who I may have to come out to later. A process I would come to regret later in life.

It turned out, mainly because of my wanting to not come fully out as a transgender woman, hiding away my true self from a loved one would reach new heights of desperation. The loved one I am referring to is my second wife who knew from the beginning of our relationship I was a cross dresser and accepted it. Everything in our relationship was good until I finally faced the truth of me being transgender, which my wife soundly rejected. Increasingly, when she was working nights, I was out exploring the world as a trans woman to primarily see if I could make it or not. When I found I could, I began to go out more and more which led me to having more chances of being caught. All of which led to huge fights when I came home as my feminine self and she was waiting for me. It was like I was a kid again and resented the process completely but it was like a train wreck waiting to happen.

Our relationship became so strained, my wife told me things like why didn't I just man up and live as a woman. A great point which I never did while she was alive. Somehow, it was similar to me trying a last gasp attempt at saving what was left of my manhood at her expense.

When she did unexpectedly pass from a massive heart attack, at the age of sixty, I finally was able not to worry about any close gender encounters. I had paid my dues and was so happy to fully come through an often very uncertain life and live in the world as a fulltime transgender woman with no negative people in tow. A dream I thought I could never achieve.   

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