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Every once in a while I receive a question about how I transitioned into a different transgender world.
For a time I made mental lists, outlining where I would go and what would I do. Before I became involved with lists, I needed to decide once and for all I was indeed a transgender woman and had transitioned from being a very serious cross dresser or not. Once I did, my existence became so much more complex. In essence I had to decide a new path for the rest of my life. What would I do about my family, friends and finances. It was all so easy and fun and games when my only worry was how I looked in the mirror. After I decided to do so much more, I really needed to make my mental lists for the gender challenges I was suddenly facing.
The first lists I made involved where I was going in the world. I needed to challenge myself and do extra trips away from the usual women's clothing stores and seemingly safe gay venues I was going to. My expanding life was all too predictable and provided me no chances to expand my new feminine perspectives. Clerks in stores were just interested for the most part in my money and the gay venues just mistakenly thought I was a drag queen. One big exception were the lesbian bars I discovered. I went primarily to two of them. I was hated in one and accepted in another. The lesbians in the second bar were intrigued by me and I was even asked one night to sing karaoke by a large butch who wouldn't take no for an answer. Since I am a terrible singer, I sang in a low background voice and somehow made it through my musical challenge. I crossed the evening off of my lists and made a mental note to attempt to never see her again. Which I did not.
On occasion, my activities collided head on with me hiding all of this from my wife. When my wife needed to work her retail job at night, many times I would use the time to head out the door and explore knowing I would need the time to be home, take my makeup off and appear as if nothing happened when she returned. Many times I was not successful and a huge fight would ensue when she saw vestiges of eye makeup left behind. Somehow we were able to make it through the skirmishes and most of the time I made it home before her.
Many nights it was difficult to pull myself away from my list to keep from getting in trouble. I remember vividly the night another butch said to me she should take me home. I had no idea if she knew the truth about me and what she was bringing home but I was out of time and couldn't wait around to find out. I couldn't imagine what excuse I would have had to come with for my wife if I had explored the evening farther. I had to rip up my list and forget it, for a time.
From the confidence I had built up in the lesbian venues I went to, I then listed sports bars as my next challenge. I had always enjoyed going to sports bars to drink beer and watch the big screens when I was a guy and wanted to see if I could do the same as a transgender woman. Fairly quickly I found I could and I needed a new list of goals to conquer.
By this time, I was ready to try gender affirming hormones and plan ahead to the strong possibility of being able to discover a fulltime life as a trans woman. During this time, I was checking skills such as public communication off of my check lists and set out to try to conquer a brave new feminine world. Finally, my new life became second nature and I didn't need any more lists at all.
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