All the Gender Baggage

Image from UnSplash

 Sometimes I feel just like "Paris Hilton" in a recent hotel commercial when she had to reserve an adjoining room for all of her extra baggage. Completing a male to female gender transition often produces just as much baggage we accumulate from a life time of experiences.

Often, the older we are the more baggage we have to account for. In order to hide our feminine instincts and try our best to live as a male, we had to resort to extra ordinary measures to protect ourselves from bullies and bigots in the society around us. By doing so, our baggage became immediately very bulky and/or heavy. The problem was compounded by adding spouses, family and employment as we went on to live our lives. Before we knew it, we needed an extra room (similar to Paris Hilton) to keep and hide our baggage.  The problem becomes, when we finally decide to change our outward gender, what are we going to do with the male person who helped me to get to the transition point.  

In my case, my baggage involved having a wonderful daughter I didn't know would accept the authentic  new me, a very successful job and a loving wife of twenty five years to deal with among other things. To make matters worse, I knew my job would not accept me transitioning along with my wife who said our marriage would be over. She didn't sign up to be with a woman.  What happened to me was my daughter accepted me when I came out as transgender to her, I left my job to start my own restaurant and my wife sadly passed away. I guess you could say destiny opened the doors to put my major baggage issues aside and move towards living my impossible dream of living as a full time transgender woman. The closer my gender transition came to reality, the more baggage I discovered which needed to be considered and taken care of.

The more I was able to live my new exciting feminine life, the more baggage I found which needed to be considered, added on to my life or just discarded of. My biggest piece of  extra baggage I needed to deal with was my love of sports. Over the span of my life I had used my love of sports to drive a wedge between me and any possible bullies. I tried along the way to play football and became a fan of the sport as well as having a passing interest in baseball and basketball. I found out quite early in my life transition, I would have a difficult time bringing my interest in sports with me. It took me several ill fated attempts at enjoying myself in male gay venues to get the idea I was going at my problem all wrong. To be accepted as a sports fan all over again, I needed to go where there were other possible woman sports fans. In other words, big sports bars with many televisions and large cold draft beers. Not exactly the environment I envisioned myself in during my formative gender years but on the other hand the whole experience felt natural and I had solved one of my huge gender baggage issues. Very soon I was accepted as a regular patron in several popular venues and I was able to enjoy myself.

The other big issue I needed to deal with was my sexuality. Since I had never been really sexually attracted to any other man, I wondered what would happen to me as a new transgender woman. The answer didn't come long in being answered when I did briefly date men and still didn't have much of a spark except when I had the luxury of being on the arm of a man and enjoying the ease of acceptance I received in public from society.  Looking back, none of the lack of real acceptance from men mattered because my acceptance from cis-women soon dominated my life. I never had to worry about my sexuality changing because it didn't. 

In any other items of interest I had when I was desperately trying to live as a man were left behind. All the experience I had gained restoring an old house was a prime example. I became decidedly unhandy around the house. 

Once I had decided which baggage I was keeping and which I wasn't, life became full again and I could concentrate on building a new life by writing more and enjoying myself.  

It Takes a Village

In My Messy 
Gender Closet from
the Jessie Hart
Collection.

Even the most secure transgender person (woman or man) would probably admit transitioning was never easy. Some would admit to having transitional help while some transgender individuals had very little assistance. In my case it took a village after a certain point. By that I mean I spent my formative transvestite years very alone to experiment with my mirror.  Every time I was able to afford a new piece of feminine clothing and/or makeup, I was certain I was the prettiest girl in the room. Which was easy to do because I was the only person in the room to start with. I spent my life fearing going out in public but on the other hand wanting to so badly.

In many cases, what happened next in my transition was predictable. I learned the hard way the mirror wasn't my friend and when I finally faced the public. I write often about my poor fashion choices which led to abuse. Even with all the rejection I was facing, I still pushed forward on my own petrified of anyone close learning of my gender secrets. This continued into my days in the military when my appearance as a woman at a Halloween party led me to coming out as a transvestite to several close friends, including my first wife. Once I admitted to them my "costume" wasn't a fluke, it felt like a tremendous load had been removed from my shoulders and it was possible to begin to locate and build what would turn out to be my transgender village. Sadly, I wasn't able to seriously work on my village for years after that. I even attempted to come out of my closet to my Mom but she slammed the door shut.

It wasn't until I began to have success presenting as a woman did my village began to change. As it turned out I did not find the village as much as it found me. The more I ventured out into the public as my new feminine self, it seemed the more the public wanted to know about me if I went to the proper places. I started slowly when I started visiting certain clothing stores and malls on a regular basis. Very soon I grew tired of those places and needed a challenge to see if I could exist as a transgender woman in the world. That is when I began to stop places for a sit down lunch to interact with the staff. I was shocked how fast the public seemed to think I fit in and wanted to even communicate with me.  Communication with the public was something I had never considered because the mirror had never talked back to me. 

Amazingly to me, chances came along for me to build my new village fairly rapidly. I began to be invited to girls nights outs as well as being accepted into small  mixed gender groups in the venues I became a regular in. Looking back, I am sure I had the opportunity to easily stand  out in the crowd, even if it was only because I was bigger than most women. I found once I had reached this point of acceptance, I needed more help in building my village and I found it with the help of several cis-women I used to hang out with repeatedly. My formative gender days with all of them helped me to set the foundation to become the new woman I always dreamed of being. I can never say enough how much they all helped me when it came to me leaving my new village and venturing out. All of a sudden, my closet became a village and it was time to move on with all the help I found. I think my future wife Liz said it best to me when she said very few people have the chance to start over in life. It was my chance to make the best of it.

I did try to make the best of my new life by allowing my long suppressed feminine soul to take control and enjoy her chance to live. She definitely made the most of her chance to shine...with tons of help of my old village.  

Passing as a Woman out of Sheer Will

Photo from the 
Jessie Hart 
Collection

When you come right down to it, there are many ways to actually pass as a woman. Of course the first way is to attempt to try to know what feminine attributes you might have and go from there. Sadly the whole process entails more work than some are willing to spend time with. Others consider it a labor of love. 

When I first began my serious gender journey to live as my authentic self, I needed to discover without a doubt what my authentic self was all about.  All I really knew was that deep down inside I had never given up the idea I was a girl who was on her way to future womanhood...If I could figure out how do do it.  Seeing as how I possessed very few feminine attributes, my femininization process involved quite a bit of trial and even more error. If it wasn't for low cost thrift stores, I don't know what I would have been able to do. At those stores, I was able to buy low cost women's clothes to experiment with. The whole process took awhile but finally I began to understand the fashion basics I needed to over come my broad shoulders, no hips, and thick torso. I think now I had a one in five chance of finding a fashion accessory that made sense and helped me to work towards my goal of looking as good as I could. Through it all I kept thinking if a blouse, slacks or skirt was big enough to fit another woman, I could wear it also. 

Another major point I came up to encourage myself was, not all cis women passed as a woman either. I did my own research and came up with the idea a cis woman who may not have passing privilege makes it  in life because she makes the best of what nature gave her. Examples would be certain body parts (such as legs or breasts) which stand out all the way to a sparkling personality. At this point my thought processes changed. So what if I would never be the prettiest girl in the room, at the least I could still be the girl and be there. In many ways my new thoughts took the pressure off me striving to perfect my presentation and all of the sudden I was able to take better care of my skin and lose nearly fifty pounds on a diet. Through it all I had to tell myself I was doing the best I could with what I had to work with.  But, then again I still could fall back on all the lectures my parents gave me which said nothing was ever good enough and I could try harder.

During this part of my life, I was going through a period of immense gender discovery. For the first time ever I was going to new venues designed to test my boundaries as a new transgender woman. Most I was successful in, some I was not.  I ran the gamut from being totally accepted and even welcomed as a sign the venue was diverse in it's thinking all the way to being kicked out with the cops being called. Plus, it was during this time I was able to meet and establish friendships with a very supportive and fun group of people I could socialize with as I was desperately lonely. One of the group was another transgender woman who one night told me I passed out of sheer will power. Ironically I knew what she was saying and it took me back to the realization I had years ago. So what if I wasn't the prettiest woman in the room, I still was a woman and that was all which was important. 

These days, for years and years, I have left my old male self behind and have reached the point of having the confidence to live my gender truth full time. If someone has a problem with me, it is their problem not mine.  It most certainly took me long enough to get thereand I had support to do it but mostly my gift of sheer will power put me over the top.