Escalation or Escapism

Halloween image from the 
Archives. Min on right. 

During my life, I spent many uneasy moments in my transgender transition when I was caught between escalating my feminine gender craft or escaping back into my well worn, boring male world. 

The problem quickly became the more I escalated my attempts at being a girl, the more I wanted to do. More and more drama set in as I viewed myself in the mirror. Through it all, I wondered if I could ever put it all together and go out into the public as a novice transgender woman. Following years of escaping back, I finally did take a few tentative steps into the public eye. The first night I tried, I had decided to go to a small book and carry out convenience store just to see what would happen. I arrived and walked down the sidewalk near the store in a shopping center. As I tried to gather my courage to go into the store, I attempted to sneak a look at myself in the clothing store nearby. I could not really see my reflection and began to re-think my idea of going into the store I planned on. Then I decided my idea was not a good one and I headed home to escape back into my male self. 

For awhile, I felt relieved at my decision but then began to think I had taken the easy way out and if I continued on this path I would never discover if I could make it in the world as a transgender woman. Once I was able to locate and buy better fashion choices, including shoes and wigs, my mind started to change as far as escalating myself in the world. After going down a very bumpy road, my confidence increased to the point where I could try out the public again without escaping back to my safe male self. Even still, each time I did escape back, I grew increasingly disappointed in myself and very frustrated in the fact I was wasting all the time and effort I was putting into my femininization. 

Through all the ups and downs, I was slowly but surely gaining small amounts of confidence in what I was attempting to accomplish. In fact, I was scared of how intimidating the entire gender transition process was to me. Many times, I thought I was in too far over my head and was going to drown my entire existence in my quest to be a woman. Something always told me to keep going and the dream I was following would be worth it, so I continued to escalate my transition. 

At that point, one of the biggest surprises which happened to me occurred when I found out how welcoming other women could be. Very quickly I found women were way more apt to approach my feminine side and in return, I could learn how to interact with them also. There was nowhere to go and nowhere to hide. so escaping was out of the question. Mainly because I was living through one of the most exciting times of my life. Why would I ever want to escape. 

Still I found I needed to escalate my gender transition. My primary example was when I suddenly had a major mental shift one night when I was going out into the world. As I was going through what I was going to wear and how I was going to do my hair and makeup, it came to me I was no longer going out to trick the world into thinking I was a female, I was going out as a full-fledged transgender woman. I had taken my escalation to a whole other level and one I never wanted to go back to.  When I turned out to be successful. 

When my male life was crashing around me, the easy answer was to keep escalating into my feminine world. Which I did with gender affirming hormones. The magic little pills I started with almost immediately began to femininize my body and my inner emotions. To this day, when I change and apply my Estradiol hormone patches, I thank the powers to be I was healthy enough to undertake the program. 

I believe now, escalating into my feminine world saved my mental health and my life. The more confidence I gained as a transgender woman, the quicker my male self evaporated away. There would be no more escaping. 

Gender Prison

Image from Denis Oliveria
om UbSplsh

Many transgender women and trans men have spent numerous years in their own gender prisons. Sometimes referred to as closets. 

Unless you have had to spend time in your own prison with the walls closing in all the time, you have no idea of how bad it is. Just another proof being transgender is some sort if a choice. Why would we ever choose to possibly destroy ourselves with our gender issues. It all got to the point with me, I was doing all I could to manifest myself being as feminine as I could. When all along my male self was telling me I couldn't. 

I finally arrived at the point where I was given free time from my gender prison to explore the world as my new self. When I did, most certainly I discovered I wanted more and more free time. I discovered also, I needed a ton of work to prepare myself for freedom. I was not prepared for all the challenges I would have to face as a novice transgender woman. Since I had spent so much time cross dressing in my life, I thought how much harder could it be. I never factored in what my second wife was always trying to tell me, I did not really know much about being a woman and she was not going to do much to help me out of my gender prison. 

When she told me that, I reverted back to working ever harder to understand what she meant. Since I had studied women closely my entire life, I resolved myself to trying to get behind the feminine curtain to learn more. It would take me years to get there since it seemed I was living a life time sentence in my gender prison. Outside of a few varied chances to thrive, my prison seemed to be escape proof. How was I ever able to leave my prison without jeopardizing all the white male privileges I had worked so hard for such as family, friends and employment. It seemed the more I tried to escape, the more the walls closed in on me.

Once I staged my big gender prison break, there was no turning back. I discovered that even though my wife would not help me pull back the feminine gender curtain, other women would and I took advantage of their kindness. Even when I was able to, I found I was still looking over my shoulder for any male prison guards who were chasing me. It turned out, even in heels, I was faster than they were and I managed to outrun my naysayers which mainly was myself. 

With practice in the world, I finally put my prison time behind me and I set out to live my dream life as a fulltime transgender woman. One way or another, I had paid my gender dues for nearly half a century before I had the courage to fully transition. It felt so good to be let out of my gender prison and not have to go back. 

My parole officers turned out to be the women friends I found and cherished as I learned so much from them about living in a feminine world. When I used their input and included it with what my own inner woman was telling me, I was able to make a smooth transition even smoother. Plus, I was able to use my prison time as a powerful motivator of what not to do in the world. Even as a man, I tried to treat women differently than the other men around me. Mainly because I wanted so badly to be one of them. 

In the end, spending all the time in my gender prison did not do much for my life. I spent so much mental energy rebelling against my male world, I often wonder how much farther I could have gone if I had used all my resources. It wasn't to be because I was in my own gender prison and could not find the key.

Transgender Cheating

Image from Club Diversity 
Columbus, Ohio.

 I can safely say, I never cheated with another person during my twenty five year marriage to my second wife.

Before I put myself up on some unneeded pedestal, I have to temper my statement of cheating with saying I only cheated on my wife with one person, who was me. Why I say it is because the more I grew as a transgender woman, the more I grew apart from my wife. When I did, I started increasingly to leave the house as my feminine self to see if I could make it in the world. 

Of course, I did and when I was successful, I wanted more and more and I simply could not turn back into my male world. The more I celebrated my new world, it was done completely away from my wife. Which was a shame. I also define cheating as me going against the basic agreement we made which said I would never leave the house cross dressed as a woman. In fairness to her, she bent over backwards to make it happen. Even to the point of letting me go to a motel a couple times a week, so I could safely cross dress and explore the world. 

Even the motel agreement was not good enough for me. Very soon going out anytime my wife was working became the norm for me. My life suddenly became exciting and way too natural for me to ever return. 

The closest I ever came to really cheating came was with an encounter one night with a lesbian in a venue I was a regular in. She bought me a beer and told me she should take me home with her, which was flattering but scary since I needed to beat my wife home from work. There were a few other times my flirting almost got me into trouble mainly with other women but I never went forward with any personal contact.

Since my wife passed away very unexpectedly at the age of fifty from a massive heart attack, my vow never to cheat remained secure. Even my male self managed to never pursue any of the impossibly attractive servers he hired in his restaurants he ran. I was very proud of all of it but never was I proud of needing to lie and try to tell my wife to her face I was not going out on her with another woman. Which happened to be me. If I would have been truthful with both of us, I would left my male self behind long ago and set out to live a feminine one as a transgender woman. I was selfish and wanted to try to preserve what I had earned as a guy. The upside came when my girl self had been put into a brief submission and I enjoyed my time with my life more deeply. The downside came when the friction between my gender issues made my life nearly unbearable. 

I guess, deep down I knew my wife was ill and for the six months before she passed, I grew a beard and purged some of my feminine wardrobe. The final six were some of the most miserable I had ever faced but little did I know, it was going to get much worse before it was going to get better. Basically, through death and loss, the only strong influence on my life I had left came from my feminine self. She wrapped me in her soft arms and let me know everything was going to be alright. Her influence and my overall belief in what was right, tiding me over until my current wife Liz came into my life and reaffirmed my idea I was stubborn enough to live through my issues. Liz told me all she had ever seen in me was female and it was all it took for me to go wholeheartedly into doing away with my male self. 

I will forever be proud of the time I spent being faithful as my male self to my second wife and, on the other hand, be totally ashamed of myself of how my feminine self handled her life with my wife. Non unlike two strong women locked in a struggle. 

My excuse is I was learning my new life as a transgender woman and until I fully understood it, I was petrified of moving along.