Becoming Involved Through Isolation

 

Photo from
the Jessie Hart
Collection

When I first decided to leave my dark lonely gender closet and attempt to live as a transgender woman, I was extremely lonely and more than a little confused. 

During that time I had lost nearly everything which was dear to me. My wife had just died, along with many of the close friends I had managed to know and on top of all of that, it was becoming more and more evident I was going to lose my restaurant which I had invested so much time and money in. During this time of extreme duress, one of my only releases from the pain was resorting to my feminine self to help me.

In order to figure out where I was going to go, I had to consider several important points. The main one of course was which venue I should go to. Previously I was taking the easy way out by going to the safer gay venues I had heard of. In some ways, they were safer but surprisingly acceptance for transgender women such as me just wasn't evident. Most of the time I was considered to be just another drag queen, which of course I wasn't. Plus, if I ended up looking similar to a drag queen, all it proved was I had a lot of work to do on my feminine presentation. Another point I failed to consider was, the vast majority of men in the male gay venues I was going to didn't want anything to do with a woman anyhow. So I was left out again. 

Since I really didn't care for the overall atmosphere, I needed to find other places to live my new reality. Finally I decided to attempt to go to places I previously enjoyed as my male self, upscale sports bars with cold draft beer and many big screen televisions to watch my favorite sporting events. The best of both worlds for me if I could find acceptance as my feminine self. 

Other than a few notable rejections when I was asked to leave a couple venues I shouldn't have been in to start with, I did find acceptance. Even to the point of gaining women's room privilege's. I was still alone in a spot where single women don't go, I still was able to be considered a regular by the bartenders who even came to my rescue when I needed it due to unwanted attention from overly drunk men. To dissuade the men even further I used my cell phone as a prop. Once I sat down and began to get settled, I then would pull out my phone and acted as if I was waiting for someone to join me. Often all of my act was wishful thinking because again I was very lonely. I was stressed because on one hand I wanted to find a friend as a woman but on the other hand, I was very troubled about the how's and why's of how  it could ever happen. Those were the days I was very confused about how my gender transition would effect my sexuality. Which turned out to be a non issue which is a topic for a whole other blog post.

Speaking of other blog posts, it was through my being alone to find someone, paid off very well for me. Through the process, I ended up finding cis-women friends who were very instrumental in my navigation of the MtF transition process. They taught me more than they ever knew. 

Possibly the route I took to my transition success is not the path others should take but becoming involved through isolation worked for me.   

Gender Escapism

Image from UnSplash and Let's go Together

 For most of the earlier years of my MtF gender transition I literally and figuratively tried to hide behind my skirts. As I was attempting to make my way through an unpleasant male existence, when nearly anything happened to me which I considered unpleasant, I resorted to thinking if I was feminine I could escape my problems. Little did I know, or consider at the time, girls/women had their own set of problems to deal with. 

Let's take dating for example. As I was very shy to begin with, asking any girl out was a huge problem for me. From that point forward I would have rather been the pursued not the pursuer and have someone ask me out instead. Of course it never happened. Another example was when I didn't make the cut for the junior varsity football team at the very small school I attended. When it happened I immediately wanted to go back home and try on my feminine clothes in front of the mirror. In addition, my top fantasy was how it would be to be one of the school's ultra pretty and popular cheerleaders. While at the same time not taking into the amount of work the girls would have to put in to do it.

It wasn't until years later when I realized how much my escapism hurt my life. Every time I ran to hide behind my skirts turned out to be a time when I had to learn to stand on my own two feet. Once I did, I finally began to build the courage to leave my male existence behind and begin a new life as a full time transgender woman. Essentially I was following through on what my second wife told me to do. Be man enough to be a woman. Sadly I wasn't able to accomplish what she told me until after she passed away and she was never able to meet the new woman I was destined to become. Since through much of our marriage I was intensely unhappy with my gender, I believe she would be happy I made it to a point where I could be satisfied with life. 

When I did "make it" to the other side of the gender border or frontier I discovered also the many faceted problems a woman has to go through to live. Cis-women are certainly born into the high maintenance gender. From everything such as child carrying and birthing all the way to just dealing with everyday appearances and emotions, women have to shoulder the burden of life.  It's no wonder cis-men say they don't understand women (or don't want to) because on a day to day basis they don't have to deal with lives often as difficult as women have to deal with. Which brings me to the point I make over and over again. Why would any man in their right mind leave an easier gender existence and attempt to live as a transgender woman. The answer is, and always will be is because we had to. We had no choice and needed to change how we lived our lives. Most certainly, the new gender grass was not always greener but we needed to try it out anyway because it all felt so natural.  Plus, the change just had to work to save our life. 

Gender escapism didn't work for me. Finally life caught up with me and taught me to stand up for my true self and live full time as a transgender woman. 

It Was a Team Trans Effort

Overall I have written several times on how a journey down a transgender path can be a very lonely experience. At a very early age we trans youth find we are on our own. We don't even have the benefit of peer influences to shape our path in areas such as make up and clothing. Especially in the pre internet days, our gender closets were very dark and lonely indeed. Because of all of that, many of us desperately wanted an understanding cis-woman to help us with our transition, mostly in the appearance department. In my case I found just because a woman I knew would help me with my makeup and clothes it did not mean she had any real expertise to help me. In fact, the first person to really help me with makeup advice was a male makeup artist at a transvestite mixer I attended. He worked miracles with me and even explained what he was doing so I could repeat the process myself. I went on to help my second wife with her make up on numerous occasions because I actually wore more make up than she did. 

Later on in life, when I seriously began to explore being a feminine person in the public's eye did I begin to find the peer support from other women who helped me transition into the person I am today. They have been so important to me over the years that every now and then I mention them here in the blog. 

Photo Courtesy Rachel

Along the way I received advice on buying a banana from Amy to practice how to pleasure a man all the way to a constant reinforcement that I belonged in the world as a woman from people such as Kim and Nikki. Who had very little to do with men at all. The experiences such as lesbian mixers all the way to woman's roller blade events were priceless learning sessions. Of course I wasn't accepted by everyone but  since I had my core of supporting friends around me, no one else mattered. In other words, my life experiences back then taught me the boundaries of what I could and shouldn't do. For the most part I had a great time as I had in depth lessons on how to blend in with a new terrifying yet exciting feminine world. 

As you can see, I was blessed with having a total supportive transgender team around me including a couple more people I can't leave out.  Rachel was another transgender woman I partied with often. She was the one who told me I passed out of sheer confidence. Which I always took to mean even if I was not the prettiest trans girl in the room, I was not going to let it stop me from living an authentic life. The other person who was so very instrumental in my MtF gender transition was my wife Liz. Eleven years ago she told me she had never seen anyone but a woman in me and I should quit straddling  the gender fence and start living full time as a woman. 

After such a slow lonely start, it was a total team effort for me to become the person I am today. I have been fortunate to have had so much help.

Life Turns on a Dime -Part Eight

I thought seriously about calling this post "The Slippery Slope." The time period covered is approximately 2007-2010 and is the time right after my wife passed away. Before we go any further, it is fair to note she somewhat supported my cross dressing desires but was dead set against any HRT or transgender moves.

Throughout my life I didn't have many male close friends and the three I did have about this time all passed away during the same time period. Plus I was coming ever closer to losing my business during the recession. So, I was left looking at a bleak social period in my life. To combat the abject loneliness I stepped up my visits to a couple of upscale sports bar/venues I was fast becoming a regular in.

During one of my visits, my regular bartender suggested I ought to meet her lesbian mother which turned out to be a friendship I have to this day. Then, on another night, another woman slid a note down the bar expressing her respect for me being me. I of course thanked her and another long term friendship was born.

Also during this time, I started to try several on line dating sites. Of which, most were dismal failures except the one I met Liz on around 2010-11. So slowly I was starting to rebuild my other life as a woman from the ashes of who I was. None of these people had ever seen or known me as a guy.

The slippery slope came as the three of them began to invite me to all their fun spots as the new me. Even a NFL Monday Night Football game! Finally I figured I had slid so far, these people had pushed me right off my gender cliff. Where is always where I wanted to go anyhow. I just didn't have the courage to do it.

Looking back now, the years were a whirlwind of learning. From learning the basics of using the women's room to dealing with men, almost all was new and exciting. There was one man in particular who treated me with respect and dignity (I enjoyed) among the rest who stood me up or expected me to dress them up. And then there was the experiences of going to lesbian mixers and being accepted (for the most part.) I went from being a "wing person" for one of my friends to being subjected to a giant/mean gender slur by a lesbian at another.

Undoubtedly, the most important part of falling off the cliff was the soft landing. Some of the padding was provided by my friends and other by my tough skin and willingness to learn. That is why I get so amused at those who think this transgender MtF transition process is so much fun or a walk in the park.

Coming up next, the doors open wide.