It's all In the Preparation

 

Anniversary Selfie from the
Jessie Hart Archives

Anyway you slice it, crossing the gender border to your authentic self is a huge task which takes a ton of work.

First of all you have to attempt to solve the problem of securing and applying makeup and clothes.  When I started I couldn't even paint my model cars well let alone my face. More times than not I ended up looking like a clown. It took me so long to be able to take my own meager funds and then sneak out to a store to buy my own cosmetics. The whole process was one of the scariest moments of my young life. To this day, I don't know how I pulled it off with my Dad working just  a block down the street. But I did and managed to learn the preparation needed to much later on leave my closet and join the world as a transgender woman. Of course with my wardrobe, again the same was true. I needed to mix and match whatever clothing items I could to do the best I could until I could afford to do better.

Perhaps two of the most beneficial things I did to further my transition was to take care of my skin and lose weight. Little did I realize, when I completed my daily hated shaving, I was actually helping my outward appearance, including when I applied a moisturizer when I did it. I am a believer it all helped when I began my hormone replacement therapy and my skin started to naturally soften anyhow. It was similar to going through puberty again. Just reversed from when I did I as a male growing up. The harsh, hated angles I acquired started to soften which made it so much easier for me to present to the world as a transgender woman.

The other main thing I did to further my male to female gender transition was to lose weight. In fact, I was able to lose nearly fifty pounds when I began to seriously attempt to the public's eye and begin to seriously go out. Of course it made finding and wearing fashionable clothes easer to find. It turned out, it was all in the preparation as I shopped for just the right accessory to go with just the right outfit. Fairly quickly, I faced the problem of over dressing the other women around me and needed to be careful if I wanted to blend in and not cause too much attention to me. Because, even with losing the weight, I still was a fairly large bodied woman and needed to do my best to present around the fact I had been subjected to testosterone poisoning in my past. 

Through it all, I learned again what I already knew. Being a woman meant joining the high maintenance gender and everything I thought I knew about being feminine had to be re-learned. A fact my second wife tried to tell me when what was left of my stubborn male ego wouldn't listen to her. When she told me I made a terrible woman, she wasn't talking about my appearance. Which turned out to be very difficult in one sense yet was the easiest  part of my transition in another. 

Often I wonder what it would have been like if I had had the opportunity to grow up as my chosen gender. To have had the peer pressure to look and act a certain way. More than likely, the grass would not have been as green as I think it would have been. Mainly because I think my Mom would have put increased pressure on me to conform to her world. Whatever the case, I think preparation would have been the key. Having more of it at an early age would have certainly helped.