Stuck in the Middle with Me

 

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Once upon a time and probably more than once, my second wife told me my cross dressing existence wasn't all about me. 

We were usually fighting about my feminine existence when she came up with the same comment. The unfortunate truth was it was all about me. I had a singular desire to look better as a woman and I knew deep down the whole femininization process would not be accepted by my wife and if I was to succeed at all, I would have to do it myself. Since she was unable to help, it meant I was on my own to discover my own fashion, makeup etc. So, for the most part, we never saw eye to eye on anything when it came to my cross dressing. Over the years, it became obvious she didn't like my inner woman at all.

Even though I knew it was and had to be all about me, life went on and we were able to stay together for over twenty five years until her untimely death. Until the end, she resisted any idea of mine I would ever want to begin down the road to trying a transgender lifestyle by starting hormone replacement therapy. When she always stated she didn't sign up with me to be with another woman again I had to agree with her.

Since she did not accept me, I started to sneak around behind her back and found out it was possible I could follow my ultimate dream. In the world I was beginning to discover, I was able to begin to carve out a new life as a transgender woman. When I did I became stuck between the two binary genders. I was trying to live as my old male self a couple days of the week and my female self the remainder of the time. Of course my life became unbearable and I sustained dark days when it came to my mental health. Being stuck in the middle with myself was not a fun place to be. I would come to learn in her own way, my inner woman who was doing battle with my wife was just as strong willed. 

I quickly figured out my old male person was going to be the first person to go away when my wife passed. I'm sure in the next life, my wife wasn't surprised to see I quickly transitioned totally into a feminine world. She always said my dog would never miss her if anything ever happened and she could have added my inner woman would not have missed her either. To make matters worse with my overall mental health, my male self desperately missed her. Possibly knowing my wife was his last chance at maintaining any sort of life.

 Even though the times I was out exploring the world as a novice transgender woman on occasion I was terrified, I pushed on to experience the excitement of exploring a life I had always dreamed of. When I did, often I was surprised at the outcome. I never expected many of the results I had when my inner feminine self took over. Quite a few times I couldn't believe how easy and natural life turned out to be.

Being stuck in the middle with me turned out to be worth all the hassles I went through to arrive there. 

Gender Variables

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When I was first looking at myself cross dressed in the mirror and when the mirror was lying to me, I felt as if I was well on the road to understanding what my life may be like if I ever had the courage to transition.

Of course I had no idea of the obstacles and challenges I would need to face as I attempted to live a life I had only dreamed of. There were plenty of times when I woke up in the morning following a vivid feminine dream wishing I was still the female I dreamed of being. The problem being was dreams don't ever equal reality. 

Reality meant I needed to learn all the gender variables I would have to learn the hard way if I was ever be able to follow my dream and live full time as a transgender woman. The first example I ran into was how I was dressing myself. I mistook trashy for sexy and tried to validate myself as a woman by trying to dress as a teenaged girl. Happily, I learned quite quickly I was dressing for the wrong gender. I was dressing how my male self thought I should, when in fact I should have been dressing to blend in with the other cis women around me. Cis women are women who were born female. 

Once I started to be able to blend in with and exist in the world as a visible feminine person, I found out again the hard way, how many gender variables I still needed to face head on. The main issue I always mention is how quickly I needed to learn to communicate in public. Unlike the mirror, these people really wanted to talk to me. At the time, I had barely given any thought of how my voice as a woman would even sound to another person. What I ended up doing was I tried to mimic the woman's voice who was talking to me. Men, for the most part, left me alone so I didn't have to worry about them. I think other women were just curious why I was trying to live in their world. Whatever the case, I needed a vocal or communication plan and quickly.

What I learned was women (as I already knew) operated on a totally different wave length than men. There were to be no more direct conversations which men do so well. I needed to learn the power of non verbal communication clues as well as the passive aggressive nature that women deal with. There were many times I ended up with scars on my back when I thought a smiling face meant support. All a part of dealing with the new gender variables I was learning.

As it turned out, I was learning new layers of the feminine gender I had only dreamed of living. Plus I was ultra confident I made all the discoveries I could when along came  even more challenges. At that point I developed the small group of women friends I needed to rise to the next level of gender variables I needed to face. Often I was terrified but determined to stay the course I was on. 

I learned once and for all what I had always known deep down. Women live a much more layered existence than men. Little did I know I would end up living all the gender variables and then some as I lived my life as a trans woman. 

A Night with the Boys

 

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Jessie Hart Archives

Way back in the early days of going to what were known then as "transvestite" mixers, I ended up having a very special experience, In essence, I was still out with the boys, without my wife, it was just they were all dressed as women. 

The evening started innocently enough, with the usual sizing up of those cross dressers around us. A little bit of everyone was there from those cross dressers who were desperately trying to hold on to their masculine selves, all the way to the glamorous "A" listers who formed their own cliques. What I didn't know was during the evening, the group organizers were providing a few makeovers from professional makeup artists. 

I was intrigued by thinking I could be chosen for a makeover if I could fight through my fear to do it. Somehow I managed to land a makeover spot and then had to remove all the makeup I had spent so long to apply. Plus my ego thought I looked pretty good. I was to find out I was wrong.

There were several artists working, of both genders. It turned I was lucky and got one of the guys who were working diligently trying to do the impossible. In my case, he did do the impossible and I went through a magical transformation. To make matters better (or worse), along the way the make up guy was trying to explain all the techniques he was using to transform my face. I did my best to remember everything he told me and in the end run, he helped me to understand things such as the power of using a small amount of blush to highlight certain areas of my face. 

All too soon he finished his work and told me to put my wig back on. I could not believe the transformation and in my mind I was so excited  to show off my new look to the rest of the group. I did receive several compliments which cemented my desire to do more when the "A" listers went out on their own after the mixer was over. They normally went to some sort of a gay or lesbian venue to continue the party. To be able to go, I needed to be invited, so I began to seek out the one of the small group I knew and essentially invited myself along. I succeeded and managed to tag along for a night with the boys, all cross dressed as very attractive women. 

On this night, I was able to continue my own "Cinderella" experience when the group decided to call a taxi cab and go to an even smaller venue which to me looked as if it was a neighborhood tavern of some sort. It was somewhere in Cleveland, Ohio, which is all I remember now. This all happened during the pre-video game era and the place had two pinball machines. After I ordered a drink, I was able to find a couple quarters in my purse and started to play one of the games. Before long, a man approximately my age came up and wanted to play the same game with me so I had a decision to make. 

The rest of the group was wanting to leave and if I stayed, I would have to either call another cab or somehow depend upon this guy I had just met to get me back to the hotel. I made the split second decision to take the safe way out and leave with the "A" listers I came with. Before I did, to rub it in,  I made sure they knew I was approached by a guy and they weren't. 

From then on, I was more or less accepted by the group although I never had their privileged negative attitude which was so judgmental to others. However, from then on I was always searching for another "Cinderella" moment when I was able to spend a night with the boys without my wife. Partly because she normally always came along.

 Sadly, it never came again.