Trying too Hard

Photo from the 
Jessie Hart Archives

As I was attempting to find my way in a new feminine world, I caught myself trying too hard to succeed. 

I tried too hard primarily when I tried to upgrade my presentation as a very serious cross dresser or novice transgender woman. The biggest problem I was having was, concentrating just on how I presented was the wrong path to take...if I took it too seriously. What I mean is, I needed to appear the best I could without going overboard and opening myself up to scorn or negative pushback. I was stubborn and held on to my hard earned previous ideas and took quite a while until I arrived at the point where I could blend in with other women close to my age. 

Now I wish I could have seen the light at the end of my gender tunnel was not the train and was actually a light which would shine bright on my future as a transgender woman. I just had to reach out and grab it if I had the courage. I was far from being any sort of a hero or role model, I was simply a person desperate to find herself and find my way down my gender path. It turned out, lessons I had previously learned in my male life came back to really help me. A prime example was my biggest lesson from Army basic training. A friend of mine who went through basic ahead of me said don't listen to drill sergeant threats and as soon as you got into shape there wasn't much else they could do to you. I connected the dots to the public scorn I received early on as a cross dresser. Once I recovered and learned what I did wrong, I could move on to be successful. 

At this point, defining success is important. Success to me became when I relaxed to the point where I could enjoy myself to a point. Often my male and female selves were fighting a serious battle for my soul. Of course my male self did not want to give up all the privileges he earned the hard way in a life he never really wanted. At the same time my strong feminine self was still wondering and waiting when her turn would come. It finally did work out for her and she didn't have to try too hard to enjoy it.

In fact, the whole time she was struggling to see the light, she was learning what she would need to do when her chance came. Now, life has come to her naturally and she is able to enjoy it. No more obsessing about what would happen next as far as her gender is concerned. Now fashion can be fun again and not so much of a chore wondering if everything works together. 

During the holidays, since my daughter has converted to Judaism, and my wife Liz is Wiccan, I don't have to try too hard anymore to find the perfect gift. 

On occasion, at my age, I think I have paid my dues primarily on my gender path. Now I can hope for the best as my life nears its end. Not being a pessimist, I am seventy four and no one lives forever and I consider myself fortunate to be one of the few humans to have experienced a life on both sides of the main binary genders.