Gender Boxes

Image from the Jessie
Hart Archives.

When I was very young, my parents did what so many others do. They constructed a gender box and forced me into it.

As I grew up, I had no choice. I was a boy and was expected to do boy things. Even to the point of receiving gifts on Christmas I did not really want. My primary example came one year when I secretly wanted a doll or kitchen set and I received a BB Gun instead. I was the opposite from the "Ralphie" character in the "Christmas Story" movie. For you that don't know, Ralphie wanted a BB Gun in the movie in the worst way.

 As I grew and began to gain confidence in cross dressing as a girl, my gender box became smaller and smaller.  On most days, it was a struggle to just exist in the world as I knew it. The worst part about it was I never had a choice. It was like I was a round peg being driven into a square hole and being told to like it. I didn't like it and my struggles led to a worsening of my gender dysphoria and mental health. Perhaps the worst part about my situation in those days was I had no one to talk to about it and knew no one with similar gender issues. I was so alone in my little gender box.

As I struggled forward in life, I discovered there were others who were in their own gender boxes and struggling with similar problems also. I like to refer to those days as my "Virginia Prince" and "Transvestia Magazine" days. First I could not believe there were so many other cross dressers in the world and they even had a regular publication I could subscribe to. Looking back, I think "Transvestia" came every two months and I could not wait until I received my new issue. Just reading and gazing at all the other pretty transvestites in the issue made living in my box a bit more bearable. Especially when I learned there were regular "socials or mixers" being held in a location I could actually drive to. I was dazzled when I went to my first mixer and saw all the different people who attended. All the way from weekend cross dressers to transsexuals' heading for gender surgeries. 

Even seeing all those different people in their own little boxes did not help me with mine. Deep down I knew I still didn't fit in with most of the cross dressers I met because I was way more serious and certainly not with the transsexuals because I wasn't serious enough. So I remained in my little box, mainly trapped until the transgender term made it's way into the mainstream consciousness in Ohio. Once I heard or saw transgender, I knew it described me better than anything I had ever seen. Finally, I could take a big marker and write proudly transgender on my box.

From there, it was a matter of connecting the dots and removing the box altogether from my existence. Of course, learning to live a new life as a new gender was a major process and not one which was to be taken lightly. To make matters worse, sometimes I tried to jump into new gender boxes and missed my step and had to retreat to try again. Even still, life had taught me by this time, nothing was going to be easy when it came to escaping being pounded into the square hole I was in but when I did, I could be happy. 

I was fortunate in that I lived long enough to escape my gender box and enjoy a new world as a transgender woman free from many worries I used to have. The process was difficult but worth it.  

Afraid to Try?

From the archives. Underground
Railroad House.
Ripley, Ohio.

During my male to female gender transition, there were so many times I was afraid, or should I say petrified to try new things.

Probably, first of all, I was afraid to cross dress in my home at all. Fearing my family would discover my deep dark secret and I would be punished. Even with all the threat hanging over my head, I decided somehow I needed to try to move forward in my femininization. When I did, I felt so natural and felt I was doing the right thing. Regardless of my deep seated fear. 

Anyway you cut it, my fears cost me time and effort in my life. Precisely, all the time I spent attempting to work around other members of my family so it could be my turn to cross dress in the mirror. The amount of time I spent thinking and dreaming of being a girl was ridiculous. Finally the pressure built so much, I had to put my fears aside and dress as a girl. Even to the point of shaving my legs. In the long term, I became better and better in hiding my wardrobe and makeup away from my Mom, Dad and brother. To this day, I do not know how I escaped detection. 

The older I became, the more proficient I became at the art of wardrobe and makeup with what I could accomplish on my very limited income. My presentation as a girl became a very real possibility but not a possibility which calmed any of my major fears. In fact, some of them were even worse. Such as how was I going to be able to live a successful life as a man when I wanted to be a woman. Plus, what was I going to do about the looming chance I would be drafted into the military and sent away to Vietnam and what would I do if I couldn't cut it in college and flunked out. I spent many sleepless nights worrying about those things and more.

More to me happened when I was in college and I started to work my way into being a novice transgender woman. In those days, presentation or appearance was always the main issue since the only time I was really out was Halloween parties. Only being out once a year put a tremendous strain on me until I couldn't take it any longer and began to sneak out of the house dressed as a woman. Initially at night in lonely places before I knew the threat of doing things like that and jeopardizing my personal security. In the meantime, I still remember vividly the first time at night when I caught my reflection in a nearby store window when I was seriously thinking about going into a nearby book/magazine store and shop for a book.  I did not because my fears got the best of me and I was overwhelmed. 

It wasn't until much later when I was able to conquer those fears and come out into the world as a transgender woman but it wasn't without complete panic attacks on occasion. The one I remember the most was when I was thinking of making the jump from serious cross dresser to transgender woman in the parking lot of an upscale sports bar/restaurant I had been to many times as a man. I must have sat in my car for a half hour looking at myself in the mirror trying to gather the courage to go in. I don't know now how I did but I somehow put my fears behind me and went in. By doing so, my life changed forever for the best. I thought.

What really happened was, I set off a new round of fears because my male self (as well as my second wife) were digging in against me becoming anymore of a trans woman than I already was. While I was sure HRT or gender affirming hormones was my next step, my naysayers were against me. All of the process added to my fears of ever transitioning full time which increasingly my mental health was telling me was the only way to proceed. 

All of my new fears even took a back seat to my new everyday life as a transgender woman. At this time, the world was so new and different as I was learning so much as I built a new life. I hated for the old embedded fears to hold me back but they did. No matter how far I had come, the farther I had to go. Major issues such as finances, family, relationships and even sexuality had to be decided before I could move one.

 Fortunately, I put my fears behind me and conquered each of  my major conflicts as they arose. Victories equaled more confidence to achieve the transgender life I had always dreamed of. When I looked back, most of my fears seemed to be so petty. They certainly weren't at the time and became major mileposts on my gender journey.

Transgender. Complex or Simple

Is the art of being transgender very complex or simple? It depends on where you are in your gender transition cycle.

Anyway you cut it, femininization is a difficult process and I assume the same is true for transgender men seeking to enter a male world. In my past, I have had conversations with a trans man friend of mine about the trials and tribulations of using the men's room. The process seemed different to me because I had always taken for granted using the men's room and ignoring everyone else in it. I experienced a much different world full of complexity when I started to use women's room. Just making sure I looked another woman in the eye was a challenge, not to mention everything else I needed to remember to survive. 

Of course the biggest complexity was fashion, hair and makeup. Since we transgender women don't have the luxury of growing up feminine, we have a ton of catching up to do. It is often more painful than fun but is something we just have to if we want to ever make it to the simplicity side of our lives. In addition, the complexity of living trans comes full circle when it comes to our emotions. Then emotions lead to our overall mental health, so it has a very deep relationship with our everyday lives. If we are fortunate, we settle into and come to an uneasy acceptance of being our authentic gender selves is the goal. 

None of the conquering of the transgender complexities came easy for me. I needed to work my way through dressing as a teenaged girl in my mind all the way to being able to present to blend in the world successfully. I needed a whole new attention to detail if I was ever going to achieve my lifetime dream of being a fulltime woman, trans or not. It took awhile but I slowly adjusted my life to a much simpler mode which included being feminine. Fashion and makeup became second nature to me as well as the difficult attempts of dealing with the public which meant mainly with other women. 

There were so many serious facets of my everyday such as being to deal with such as what my sexuality was going to be. After all, since I was living as a woman, would I be expected to have sex with men. Since I had never had sex with men, I had no idea of what to expect. Would I have any pleasure, or would I have been doing it just for my own validation. Thankfully, I did not ever have to explore the new frontiers of sex as I found I was still attracted to women and my lesbian women friends taught me it was fine to be so. So the sexuality of my life didn't change and stayed very simple.

Life is complex enough on it's own without adding in the complexities of being transgender, so we face the ups and downs of following our paths. We somehow find we are carrying pocket knives to solve a problem when all I needed was a set of pliers. It was all part of the simplification process. All along I knew women live a more complex lives than men but adjusting our existences to fit was the challenge. Ultimately, I needed to accept the challenge to save my own life. On occasion, the complexities of learning a new gender world in my femininization process became too much and I needed to try to fall back and take a break. However, breaks were short because the more I learned about being a woman, the more I wanted to learn which was aided to a large degree from finally beginning gender affirming hormones. The new hormones simplified my life even further by aligning my inner and outer selves. 

Suffering through all the complexities of transitioning genders turned out to be so worth it for me. The long journey I took led me to a much simpler world I wish I had be able to know years ago.