Afraid to Try?

From the archives. Underground
Railroad House.
Ripley, Ohio.

During my male to female gender transition, there were so many times I was afraid, or should I say petrified to try new things.

Probably, first of all, I was afraid to cross dress in my home at all. Fearing my family would discover my deep dark secret and I would be punished. Even with all the threat hanging over my head, I decided somehow I needed to try to move forward in my femininization. When I did, I felt so natural and felt I was doing the right thing. Regardless of my deep seated fear. 

Anyway you cut it, my fears cost me time and effort in my life. Precisely, all the time I spent attempting to work around other members of my family so it could be my turn to cross dress in the mirror. The amount of time I spent thinking and dreaming of being a girl was ridiculous. Finally the pressure built so much, I had to put my fears aside and dress as a girl. Even to the point of shaving my legs. In the long term, I became better and better in hiding my wardrobe and makeup away from my Mom, Dad and brother. To this day, I do not know how I escaped detection. 

The older I became, the more proficient I became at the art of wardrobe and makeup with what I could accomplish on my very limited income. My presentation as a girl became a very real possibility but not a possibility which calmed any of my major fears. In fact, some of them were even worse. Such as how was I going to be able to live a successful life as a man when I wanted to be a woman. Plus, what was I going to do about the looming chance I would be drafted into the military and sent away to Vietnam and what would I do if I couldn't cut it in college and flunked out. I spent many sleepless nights worrying about those things and more.

More to me happened when I was in college and I started to work my way into being a novice transgender woman. In those days, presentation or appearance was always the main issue since the only time I was really out was Halloween parties. Only being out once a year put a tremendous strain on me until I couldn't take it any longer and began to sneak out of the house dressed as a woman. Initially at night in lonely places before I knew the threat of doing things like that and jeopardizing my personal security. In the meantime, I still remember vividly the first time at night when I caught my reflection in a nearby store window when I was seriously thinking about going into a nearby book/magazine store and shop for a book.  I did not because my fears got the best of me and I was overwhelmed. 

It wasn't until much later when I was able to conquer those fears and come out into the world as a transgender woman but it wasn't without complete panic attacks on occasion. The one I remember the most was when I was thinking of making the jump from serious cross dresser to transgender woman in the parking lot of an upscale sports bar/restaurant I had been to many times as a man. I must have sat in my car for a half hour looking at myself in the mirror trying to gather the courage to go in. I don't know now how I did but I somehow put my fears behind me and went in. By doing so, my life changed forever for the best. I thought.

What really happened was, I set off a new round of fears because my male self (as well as my second wife) were digging in against me becoming anymore of a trans woman than I already was. While I was sure HRT or gender affirming hormones was my next step, my naysayers were against me. All of the process added to my fears of ever transitioning full time which increasingly my mental health was telling me was the only way to proceed. 

All of my new fears even took a back seat to my new everyday life as a transgender woman. At this time, the world was so new and different as I was learning so much as I built a new life. I hated for the old embedded fears to hold me back but they did. No matter how far I had come, the farther I had to go. Major issues such as finances, family, relationships and even sexuality had to be decided before I could move one.

 Fortunately, I put my fears behind me and conquered each of  my major conflicts as they arose. Victories equaled more confidence to achieve the transgender life I had always dreamed of. When I looked back, most of my fears seemed to be so petty. They certainly weren't at the time and became major mileposts on my gender journey.