Alawys Going Somewhere

Image from Louis Paulin
On UnSplash

 Back in what I call my formative years, I grew used to trying to outrun my problems. Between college and my military service I literally was moved or decided to move on my own an average of every year and a half. It all started when I left home for college for a year and a half. Amazingly, during this time my gender dysphoria disappeared and suddenly I was free to live a somewhat normal gender life. I say normal because during this time I had several dates with girls from the East Coast who were much more sophisticated sexually than anything I had seen in my shy Midwestern upbringing. In fact, my Mom unknowingly set me up with my first sexual experience with one of her older (not a minor) students where she taught high school.  I think she was nineteen and I was eighteen, so I had a lot to learn. 

The school I went away to was one a group of Midwestern Ivy League schools for students on the East Coast who couldn't make it into the top notch schools or universities in their back yards. What happened was I ended up partying with my friends mainly from Philadelphia and Baltimore and not studying enough to maintain grades to not get drafted into the Vietnam War. After a year and a half I picked up and moved back home to attend a much more academically forgiving nearby university where I could thrive. Which I did by even making the Dean's List several times before I graduated. More importantly to me back then was the fact I was drawn back into my old cross dressing memories of home while I was able still to land a Disk Jockey job at a small local radio station which happened to be owned by a very powerful congressman which turned out to be very important to my future. For awhile I was quite satisfied with satisfying my cross dressing desires by putting on my feminine clothes when my parents weren't around just like the old days while at the same time attending to school while I built my self a career in the commercial radio business. 

Just when I thought I had it all together, Uncle Sam came along with several all expense paid tickets to work and travel in exchange for three years of my life. I was able to salvage my radio career with the help of the congressman I worked for but my cross dressing would certainly have to be on hold for the foreseeable future. My first move was a bus trip to beautiful (?) Ft. Knox in Kentucky for Army basic training. I didn't get to see any gold but I saw many fellow recruits going through tank infantry school. A nice way of saying they were headed to Vietnam to be cannon or grenade fodder for the war. Basic was tough but not tough enough to wash out any or all ideas I had of ever following my feminine dreams. In fact in many ways I think basic just made my dreams stronger because I couldn't wait to get out and live them.

Following Basic at Ft. Knox, little did I know the amount of travel Uncle Sam had planned for me. It all started innocently enough by getting transferred for advanced training at the Defense Information School in relatively close by Indianapolis, Indiana. It was close enough to my home I could drive back and forth for weekends and leave but not close enough for me to cross dress when I was home. It turned out I wasn't going to stay in Indy long before I was sent to Thailand along with my close knit classmates to help run a radio/tv station in Udorn which had recently been destroyed by a battle damaged F-4 fighter jet which crashed at the end of the runway killing all working in the station. Since we were Army working for the Air Force, we received extra pay to live off base. Of course living off base put me face to face with the Thai Ladyboy culture. As advertised, many were indeed beautiful but all I did was admire from afar. I was afraid of any stigma which would have been attached to me if I had tried to know any of the alluring creatures further. 

After my year in Thailand, I was trying hard to get assigned to Europe and work for the AFN Radio Network. I finally did make it but not with more moving around. What happened was I had two sets of orders. One verbal and one paper. I decided to follow the one on paper and report to the Aberdeen Proving Grounds in Maryland for duty in their information office. What turned out was I wasn't supposed to be there and was sent back home with another weeks worth of leave before I had to leave for Germany, where I wanted to go to start with. After all those convoluted military moves I finally had the chance to live out my dream of seeing Europe because once again I received extra pay to live off base.

I am fairly sure all of this moving affected me in many ways when I was honorably discharged from the military and through with school. More on how it affected my gender dysphoria in another post. 

Woman Up

 Perhaps you have been told to "man up" and do something during your life. The best example I can come up with is going through basic training in the military. These days with the welcome influx of women in the military, basic training may be a different experience but in my days it was definitely not a coed experience. Since it was during the days of the Vietnam War draft days, I had no choice but to man up and make it through. Which I did. I ended up taking approximately twenty five pounds of fat

Photo from the 
Jessie Hart Archives 

off and replacing it with muscle. All of that was good I suppose but at the same time I was desperately missing my urge to cross dress into my feminine clothes. There were times when we were on forced full gear long marches the only thing which kept me going was dreaming of the times I had when I dressed as a woman. I had to "woman up" or hitch up my non existent feminine panties and successfully concentrate on the task at hand. 

Over the years it became evident to me the whole Army experience became a focal point in my life. I learned the hard way I could eventually overcome almost any obstacle on my way to living as a fulltime transgender woman, On occasion I was certainly terrified of crossing the gender frontier and losing my male privileges' but I went forward anyway mainly because deep down I felt so natural doing it. As I entered the second major transition in my life from cross dresser to novice transgender woman, the thrill I experienced when I succeeded and survived was like nothing I had ever experienced before. It felt like I had finally had woman-ed up I did what came naturally.

The problem was all my good feelings were directly challenged by my wife's desire not to live with another woman. The process became a prime example of being stuck between a gender rock and a hard place. I felt I had to continue to explore living as a transgender woman but she was standing in my way. In all ways she represented any chance I had of continuing to live what was left of my male life. Finally one of our fights became so bad she told me to man up and become a woman. She was prophetic in many ways. After a failed suicide attempt on my part and a sudden death from her, the doors swung wide open for me to finally allow my dominate feminine being to exist. As it happened, my life really changed and I had to hitch up my big girl panties or woman up to survive in a world I had only dreamed of. As I discarded all of my old male clothes, with the limited funds I had I had to make sure I was buying useful utilitarian clothes which i could be attractive in and still blend in well with the other women I met. 

It was around this time also when I decided I could retire on early Social Security pay as long as I sold the house full of antiques and collectibles I owned. Through a couple of on line services I used, I was able to exist and retire so I didn't have to attempt to transition on the job in the very conservative company I worked for. I guess you could say I missed being able to woman up by transitioning at work and dodging a major hassle other transgender women and trans men face. 

From that point forward, the biggest hurdle in my MtF gender transition was my decision to woman up and schedule a doctors appointment to see if I could begin hormone replacement therapy. When I found out I could, I was ecstatic. I could now woman up again and take another major step towards achieving my gender dream. In life though nothing remains static and now I remain ready for the next challenge I have to get ready for. Or woman up again. 

How to be Transgender

What a question...right? All of us most certainly have a different but yet oddly similar answer to the question. Along the way here on the blog we have created quite the niche with transgender women who have decided to complete their gender transition later in life. A commitment such as that requires quite the sacrifice. Often we have to give up long time family ties losing beloved former friends and family who refuse to accept our new authentic selves. 

Photo from the
Jessie Hart Archives

Along the way, we had to learn our own ways what it meant to enter a new and very foreign feminine world. I know in my case, often the whole process was terrifying. It occurred to me  I was giving up years and years of effort to be a person I never really wanted to be. I know none of that sounds different than the path you followed. Other examples include time in the military and the time and effort you had to put in to grow up fast as your transgender self. After all, we didn't have the benefit of a mother, sister or peer group to aid in shaping our new world. For me it was very difficult to learn I would never be able to recapture a past as a girl I never had. As I write many times, I was guilty of trying to dress as a teenaged girl stuffed into an oversized male body still loaded with testosterone. 

By living my mistakes I learned how to become my unique form of transgender woman. More than likely many of you did also. Many of us are fortunate to have been shaped by the cis women around us. For each disapproving spouse there are so many more who often begrudgingly come to accept the new woman in their relationship. I know with me, even though my second wife never accepted my transition to a transgender woman, she still shaped my transition in more ways than she ever knew. Her comment I was a terrible woman was an example. It came after a practically successful time for me when I presented as a woman. It turns out she wasn't referring to my appearance at all but more about the remaining male ego I still dealt with. It took me years to finally realize what she meant. I'm sure many of you, similar to me, considered yourself to be students of all things feminine. It was difficult to figure out what was good and what was bad for me and entered into how I felt I had to progress towards how to be transgender.

Many of us also who were raised in the pre-internet generation feel our gender growth was stunted in many ways. Leading us to feel we lost the chance to work on a gender transition earlier in our lives if we only had the information to learn from. Since we can't go back in time, we just became better in working with what we had to work with. Sometimes we pashed too hard when we tried to explore outside our restrictive gender closets and had to dial our goals back just a bit until we could get back on track and put our lives back together. 

Together was the key term. Since we have lived longer, the more gender baggage we had to consider bringing with us as we crossed the gender frontier. For instance I had to decided what I was going to do about my lifelong passion for sports. I ended up solving the problem by discovering and being able to socialize with several other women who enjoyed sports as much as I did. How to be transgender for me suddenly became a positive experience for me. On the negative side, my brother who I used to watch many games with vanished from my life when he and my sister in law refused to accept my new feminine self. Of course there were many more important baggage items to consider such as property, jobs and family to name a few. It all is the exact opposite to what young transgender folks face. Their problem is how do they face the future of difficulties with employment and benefits as they build their lives. It seems nobody wins. 

The bottom line is how to be transgender is never easy and is for gender survivors only.