Tuesday, April 7, 2026

Everything Was Fine Until It Wasn't

 

Image from Danny
Messina on UnSplash

Many times, when I was sailing along thoroughly enjoying my feminine self out in the world, I would come to a rude awakening that something was not right. As I experimented as a novice cross-dresser fresh out of the mirror at home, I learned any number of things could be wrong. Including the cruel imposter syndrome which haunted me. A great topic for another blog post.

Or maybe my makeup was not on point, and I looked like a clown in drag, or I had that old male scowl on my face instead of a pleasant little smile which gave away the fact I was not enjoying myself the way I should. But something was wrong as I was doing what I wanted to do for a change, and I needed to show it. Not revert to my old male ways of trying to scare people off before they even started to interact with me. It is something I work on to this day as it is easy for me to fall back into old gender habits. I needed to work hard to put my entire new feminine image into play when I was out or no matter how good my makeup and fashion looked, I was not going anywhere in my development as a transgender woman.

A quick example of the problems I was facing with my face happened one day when I was out shopping in a woman’s clothing store. When I came around a rack of clothes, I was startled by a young girl staring up at me. Worse yet, I was prepared for the worst when she took off looking for her mother. I was semi-relieved when I heard her say, look at the BIG woman, and I thought she had that part right. Until she said, the BIG MEAN woman, and I immediately felt bad that she thought I was mean. From that point forward, I put a slight feminine smile on my face as my final touch of makeup. Everything was right with the world that day (including the little girl who thought I was a woman) until it wasn’t.  Lesson learned.

Changing the way, I looked at the world with my face was just the beginning of improving my overall presentation in the world of ciswomen, young and old. Early on, I paid quite a few brutal dues when it came to encountering groups of teen girls in the malls I went to. We all were in the process of discovering our femininity, and the girls took their humor out on me vocally and it hurt but the process helped me to develop myself to a point where I could better blend in with the new world I was trying to conquer. I just had to learn to conquer in a different way than I had ever had to before. I could not just hope to bluster my way through life as a man which I had gotten used to, I needed to finesse my way through until I began to feel the benefits of female privilege past the occasional man who opened a door for me.

Everything was fine, until I learned I was just getting started on my dream to live a transfeminine future. I had no idea how complex a woman’s life could be with a passive aggressive future in store for me. Plus, a future where for a change, to survive with other women I needed to completely listen to what they were saying and make sure I looked them straight into the eye, so I did not miss any nonverbal communication which was coming my way. Several times, I was helped out of potentially dangerous situations with toxic men by paying close attention to the nonverbal cues being given to me by concerned women with much more experience than me.

For the most part, this time of my life, in my thirties and forties , everything was fine with the gender juggling act I was attempting until I pushed myself too hard, challenged my mental health and continually got in trouble with my second wife who caught me trying to sneak back into the house after a night of living as my newly thriving feminine self. At that point, massive fights occurred which ended with me trying to promise I would never go out again. Which I knew would never happen. Once I had seen the world from my vantage point of a trans woman, deep down I knew I could never go back to a completely male life. I think my wife knew that too and that is why the fights we had became so vicious. Particularly when she told me I made a terrible woman because (in my words) my gender workbook was not filled out, and I had not paid my dues. Which was exactly what I was doing when I went out to live. I was sad I couldn't share my new knowledge with her but it was just not meant to be before she suddenly passed away.

After she died, nothing was fine as I was intensely lonely and needed a shoulder to grieve on. I found that shoulder in a predictable place and she was there all the time, my transgender self. When failure was not an option in my life, all the lonely nights I spent exploring the world around me with other women proved to be an invaluable experience when I learned I did not “make” a terrible woman after all. It turned out, I did not “make” anything at all, I just found my way to a place I always should have been, and everything turned out of be fine and I could take the wasn’t away from it.

I was even happy for the first time in my life as the heavy expectations of a male life I wanted no part of were removed for good. Being free to be the true me was the best move I ever made and my only problem was I did not do it sooner. Everything was fine, it was just hidden from me by myself. When revealed, I was free to never look back.

 

 

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Everything Was Fine Until It Wasn't

  Image from Danny Messina on UnSplash Many times, when I was sailing along thoroughly enjoying my feminine self out in the world, I would c...