It was All so Natural

Image from the Jessie Hart Archives. 

Even though I was facing tremendous hurdles as a cross dresser and/or novice transgender woman, everytime when gender times became tough, I kept on trying. Mainly because deep down  I felt so natural when I was cross dressed head to toe as a girl my age.

Although the time I was cross dressed felt so good, the length of time I was able to do it was never enough. Had I had more knowledge back then, I would have realized I was a transgender person. A big difference to me from only being a part-time male who enjoyed cross dressing in women's clothes. As I discovered more and more about myself, I discovered I was a woman cross dressing as a man during the majority of my life. I only knew I was not enjoying or was being fulfilled as a guy. The whole lifestyle never felt natural to me. 

As time went by, I increasingly followed the natural path no matter how difficult it proved to be. More often or not, I encountered very many severe twists and turns. Again, I was encouraged by the natural moments I experienced when I finally encountered the public as a trans woman. It was like the path had big sign boards along the way with directions on how to proceed. Or once I made it to a certain spot in my new gender life, I could set new goals. The example I always use was when I started to progress past just going shopping in clothing stores where they didn't care if I was a man dressed as a woman or not (because my money was green) and began to challenge myself in restaurants where I needed to interact one on one with the serving staff.  

From there, my goals became to refine and test my restroom skills if nature called during one of my longer outings. It was during some of my restroom visits when I  really needed to feel natural and spread my gender wings. I found out quickly I needed to be able to look other women in the eye and smile even though I was very scared. 

Through it all, I lived and was able to move forward towards new enticing goals of living life as a transgender woman. It was during this period of my life when I began to seriously consider moving forward with gender affirming hormones. Sadly, my second wife was very much against any idea of me being on hormones saying if she had wanted to marry a woman, she would have looked for one. In other words, she didn't sign up to live with another woman, trans or not. I loved her deeply and no matter how difficult it was, I tried to honor her wishes until her untimely death after we had been married twenty five years. 

Her rejection of any idea of me moving forward with HRT just put an extra strain on my mental health which in turn, led to a suicide attempt. Following the attempt, I tried yet another "purge" of my feminine wardrobe which of course didn't work. It wasn't too long after my final purge, she passed away very suddenly from a massive heart attack. As I write about often, her death was the ultimate shock to my system because I was always so self destructive there was no way I thought I would out-live her but I did.

When I did, I decided it was time to live my dream of being a full-time transgender woman. I took the natural path and never looked back.