The Ultimate Challenge

Vacation image from Kansas
by JJ Hart

I am biased but I think changing how you live to reflect your authentic gender self is one of the toughest things a human can do. 

Perhaps you noticed I said reflect your gender tastes not change them. I believe our transgender selves are already determined and we are attempting to sync them up to our extremal selves the world can see. The path varies for most of us but the final goal is always the same. Sadly we have many obstacles in our way. 

One of the main ones is trying to overcome the effects of testosterone poisoning which gives us the hated male characteristics we did not ask for. I remember hating all the changes which were happening to my body and how the changes would effect me when I attempted to cross dress in front of the mirror. All I knew was my life was changing for the worst and I did not want it. Much later on when I became much more serious about my femininized presentation in public, my goal was to hide my broad shoulders and the angles of my body with new fashion. 

It turned out, testosterone poisoning and new fashion were the least of my problems as I continued along my path to the ultimate challenge of living as a full time transgender woman. There were so many times I never thought I was going to make it. I had so much baggage to sort through as a man as I had acquired over the years. Since I had spent so long doing my best to build my life, then I needed to decide what to do about my family, job and friends. Leaving me between the gender rock and a hard place. Often I did not know how I was going to find my way out of my predicament. Was I still a man, or a woman and what about my long standing sexuality.

Obviously, the ultimate challenge was to sort through all my issues while I was still attempting to live my so called normal life as a man. I ended up trying to live a little at a time as a trans woman until it began to feel so natural I never wanted to go back. Slowly but surely I was proving to myself I had been born feminine and just forced into the wrong gender by some sort of a cruel twist of fate.

It was around that time, I found I was not alone and began to discover other challenges on my path to transgender success. I learned from others around me about their own successes and failures or triumphs and purges. Often my own feminine wardrobe would be gifted by an acquaintance's giant purge. In fact, my first set of expensive silicon breast forms were gifted to me. The breast forms were a real step forward from what I had ever had before and would help me to present better so I would not be discovered as a man.

As Paula wrote in and commented: "I don't know if we ever get over that fear of being found out, of being exposed and ridiculed. I think this is much more about how we see ourselves than how others see us, I look in the mirror and see all my history, the Dan Dare chin and the prop forward shoulders, others just see a late middle aged woman who happens to be on the tall side."

Thanks for the comment and as I am fond of saying, these days I present as old. Since the genders have a tendency to merge together later in life. I am also happy to have made it to the place I have in my life but as I near my seventy fifth birthday, I know the ultimate challenge is yet to come.  

A Genderless Journey

Image from the 
Jessie Hart
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Recently I needed to take our car to the oil change place to get the transmission fluid replaced. 

In the past I have written concerning my paranoia of going to male dominated places. Since normally I am the only feminine person at the oil change place, the usual paranoia set in. The last time I was there, I was called "Ma'am" several times and had no gender problems so I did not really expect anything else this time. 

To prepare, I shaved closely, put on my foundation and contour blush with lipstick and was ready to go after tying my long hair back. Off I went to get the car serviced hoping I would not be mis-gendered. 

It turned out all my paranoia was baseless. I was treated with respect and not referred to as sir. Plus it turned out the whole process needed much more work than a simple oil change. So the manager was very much involved in the process. At times, he was so involved I wondered if he was trying to impress me. He even went as far as helping me turn off the "perform maintenance soon warning" off. Maybe I was the recipient of female privilege. Or, I needed help and he volunteered. 

Very soon the process was over and I was free to go (after I paid) and it was time to go through the drive thru of our favorite coffee place for a treat. The pressure was off and once again I wondered why I got so worried about going at all. Looking back, I have never experienced any negative feedback when I have gone to male dominated spaces. I guess I am afraid of being taken advantage of. When most of the time the opposite has happened. For the most part, men have bent over backwards to help me.

Maybe I will never change but I doubt it because the transition scars  run too deep. My gender dysphoria ran too deep as a transgender woman. It could be time to change my own oil.   

Playing the Victim as a Trans Woman

Image from Jen Theodore on UnSplash

It has always been easy for me to play the victim at times during my life.

Primarily, when times started to get rough in my male life, I could day dream of escaping into my female world .Usually I try to point out after a particular difficult day on the football practice field, I could wistfully take a look at the cheerleaders not so far away and instantly feel better. Of course, I was quickly brought back to reality by my position coach. Or by the offensive lineman who was intent of driving me into the ground. 

Over time my escapism became a habit, especially when I discovered how intense my feelings became when I cross dressed and interacted with my mirror. Suddenly I was not the victim anymore when I looked at the girl in the mirror. Which was all good until I found I wanted so much more than an image of a girl, I wanted to test my new self in the world. 

At the same time, my work was training me not to be a victim. As I rose higher and higher in management structures, I learned the buck stopped with me and I was only as good as my employees who worked with me. My problem then became carrying the same ideas over to my life as a novice transgender woman. Even though, I was still married to my second wife and was interacting with many many strangers on a regular basis, I was still extremely isolated and alone with my gender issues. Just cross dressing in front of the mirror wasn't enough and still I felt as if I was a victim. Why did I have to suffer from extreme bouts of gender dysphoria. 

The answer was always the same, I was stuck with who I was and I needed to somehow make the best of the situation. I dedicated my life to finding out more and more of what my wife was telling me when she told me I knew nothing about being a woman. I learned I did not and instead of being a victim, I needed a way to be allowed behind the feminine gender curtain. It wasn't until I made the decision to put my cross dressing ways mentally behind me and pursued ways to enter the world as a transgender woman did I begin to make serious inroads towards my dream. I know I am just dealing with labels to some but to me the distinction between transgender and cross dresser was huge for one major reason. A cross dresser to me just wanted to look like a woman and a transgender person wanted to be a woman. My ideas led to several spirited discussions on message boards as you can imagine.

As life moved on, I hated to be called a victim and did all I could to avoid it. I went to any extent possible to not going back to my former self feeling sorry for himself. In my own way, I felt proud of the fact I had been able to put all the self destructive behavior behind me. I was especially happy my suicide attempt had failed because I found I still had so much to live for if only I was able to reach out and grasp it. It was amazing when I stopped being a victim and was trying to live two gender lives was behind me. The pressure was off and my mental health improved. 

Playing the victim as a trans woman just didn't work for me. I did not have to worry anymore about what gender I would have to live as on any given day. When my dominate feminine self was finally given her chance to live, she took over and made my life worth living again. The icing on the cake so to speak was when she was able to make and flourish with a whole new set of friends which included my wife Liz. All of them never knew my old male self and I was able to build a new person from the ground up. 

Life was exciting and fun again or maybe for the first time ever. My old male self predictably knew how to be successful but never knew how to make friends and be satisfied. I was so fortunate to have been able to slip behind the feminine gender curtain and discover how the other half lived. I was accepted and loved it and never had to turn back.