At the Crossroads

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Jessie Hart Archives

As I continued along my gender path to living as a fulltime transgender woman, I arrived at several crossroads. 

The first of which was finally deciding I was transgender at all. For years I considered myself nothing more than a very serious cross dresser. Perhaps the biggest positive aspect of staying a cross dresser was my wife knew of my gender pastime before we were married. She even grudgingly bought me gifts such as woman's clothes. In fact, we had a separate gift exchange at Christmas every year especially for my feminine self. 

On the other hand, my wife was totally against any idea of me being trans, saying she didn't want to live with another woman. I had no comeback for that argument since she did marry my male self. Still it did not stop me from exploring ever further the feminine world I thought I wanted to live in. As I did my explorations, the process felt so natural I just had to keep going. At the crossroads I decided I was indeed transgender and I was pursuing a lifestyle not just participating in a hobby. From the point forward my life changed and I had many new decisions to make.

Decisions such as how would I even structure a totally new life in a woman's world. Along the way, I learned the possibility of living as a trans woman meant so much more than just doing my best to present well in the world and blend in with the public. What would I do about the three "F's" as I called them, or family. friends and finances. At the time, I didn't have the answers to many of the questions so I kept searching. Of the three challenges, I decided to come out to my family first and see how it went. When I did, I received a fifty-fifty split in return. By this time in my life, my close/blood family had been reduced to two people. My daughter and my slightly younger brother. As it turned out, my daughter was very supportive and my brother was just the opposite. I tell the story often how I gained a family with my daughter's in laws and lost my brother's family at nearly the same time. Sadly, it all happened over a decade ago and things have never changed.

The next step I needed to consider at my crossroads was what would I do about what friends I had left from my old male life. Again, sadly, I had very few close male friends and had lost most all of them to death in a very short period of time. So I had very few friends to tell. No worries since I had never been able to make since seemingly I kept pushing people away my entire life because of my gender issues. I thought the fewer friends I would have to tell, the better off I would be. 

On I went at my crossroad when I came to the third "F" which was finances. I obsessed on what I would be able to do to support myself. I had built myself into a successful well paying job which I knew would be impossible to transition genders on while I worked it. What did work in my favor was my age. I was close enough to to retirement age to consider taking an early retirement. Which meant all I had to do was work a couple more years and then not have to worry about transitioning on the job. 

What ended up happening was, I painted myself into a corner I couldn't get out of. The pressure grew so intense as I tried to live both as my old male self and my new feminine self. It literally tried to kill me before I said enough was enough. One night as I sat alone and pondered what I was going to do, I finally decided to do the right thing and give up totally my old male self and live as a transgender woman. 

From that point forward, I felt as if a giant weight had been lifted off of my shoulders. I had made the correct turn at the gender crossroads and was able to move on with a new life. I waited for the paint to dry in my life and gently learn to live as my authentic self.