I'm Back...Mostly

 

Well, my wife Liz and I's vacation to the Florida Keys was eventful, with many unexpected turns.

Since I have quite a bit to write about, I will start at the beginning of our bus trip. As we boarded a nearly empty bus way before dawn in suburban Cincinnati the morning was very cold and clear. From our boarding point, we needed to make two other stops to pick up other passengers for the trip in nearby Northern Kentucky.  Since we were nearly the first on the bus, my paranoia about being the only transgender passenger was calmed, especially since I was under the cover of darkness. 

As daylight came around and the bus filled up, the pressure for me to make a good first impression came with it. I managed to cope with a small mirror I put away into my purse, along with my foundation powder and lipstick. So instant touch ups were within my reach.

Of course, all too soon came the all-important first rest room stop. I stayed very close to Liz as we went in and there were no problems with anyone on the bus, or other strangers who were already coming or going in the women's room. I did my business, washed up and left with no interference which made me feel relieved after all the months of worry I put into thinking of what could happen. 

At this point, our bus driver deserves a strong recommendation for his work in getting us safely through very snowy and icy road conditions we encountered as we made our way south from Ohio. He also was available to help me on and off the bus when needed. 

Long story short, we made it to Georgia and spent the night in Macon. Then off to Orlando for our next stop.  By this time, I could not wait to make it to our staging destination of Key Largo. Then Liz and I began to notice how many people on the bus had bad coughs. Which is a spoiler alert for what happened to me later in the trip and would involve a trip to a hospital in Georgia. 

More on it, plus a very pleasant trip to Key West coming up when I finally begin to feel better, because I caught Covid on the bus. Even though I had been given the booster three months ago. Make of that what you will.

 

 

Gender House of Cards

 

Image from Erick Langfield on Unsplash.

Just when I thought I had my life altogether, the world collapsed on me.

For example, when I thought my makeup and hair was the best, I could do, I would walk or scowl like a linebacker and ruin my entire feminine image. Of course, then, I would have to recount my steps and see what I was doing wrong. It took me years to build a solid foundation to build my gender future on because my base was so weak.

What made matters worse was the fact at the same time, I was beginning to do so much better as a man with my career. It was like I was succeeding despite of myself. Down deep, I attempted to destroy everything I worked so hard to achieve. All the self-destruction really took a toll on me and my mental health. To make matters worse, on my worst days I would attempt to take my gender frustrations out on the people closest to me. I became so bad; I even lost a job over my actions. Perhaps the worst part was, I did not grasp what was happening to me. I kept repeating the same old stop-gap routine of cross dressing once or twice a week, feeling better for a day or two before I would revert back to my old gender frustrations again. Predictably, my frustrations would repeat, and my gender house of cards would come crashing down again. 

Finally, as I began to acquire more confidence in my transgender womanhood, I started to increasingly build a better base and feel better about the major struggles I knew were coming up ahead. Primarily, what was I going to do about my twenty-five-year marriage to a woman I loved and a successful job I would have to leave behind. And all of that just scratched the surface of all the obstacles I would need to face such as what would my sexuality be if I decided to live full-time as a transgender woman. The path ahead, at the least was very murky. 

Since I was a very social person, I needed to figure out how not to be so lonely anymore. I just could not keep going out to be alone. My dilemma was men did not approach me seriously and I did not know how to react if they did. My first date with a man was with a transgender man who afterwards said I was very scared. Which was true. The problem became when the only other path to being social for me came by approaching other cis women. Fortunately, I did not have a problem because more and more of them approached me. For whatever reason. Regardless, when I went out socially, I ended up at the least talking with other women. Just having the chance to practice my feminine communication helped me to build a better gender base to build from. 

From that point, life became easier, and my path became clearer. Increasingly I understood I needed to leave the male life I never really wanted behind and jump the gender border at whatever the cost. I was near the age of sixty and was so tired of living a lie and was to the point if I did not complete my transition, I would never have the chance to live my dream.

By this time, I was able to build a solid gender house of cards, so everything turned out successfully when I made the final move. Perhaps here would be a good time to quote Paula from the UK: "For some of us there is a real need not just dress as a woman, for the world to experience us, and accept us as a woman ~ it is not enough that in our mind we are women, we need to go all the way; and that is why we need to transition. I too remember my wife saying (with no intended irony at all) "It takes balls to be a woman"

Most certainly Paula our wives were right. That is the primary reason it takes a solid foundation to approach transgender womanhood. Thanks for the comment!

I Chose Me

 

Image from the JJ Hart archives.

In an extension of yesterday's post, I decided to explore how I chose my inner feminine soul over my forced male existence I was rebelling against.

Basically, the deciding factor came down to how natural I felt as I cross dressed in the very beginning of my gender path to freedom. Very early, I remember vividly how I so desperately wanted to be more than just a boy dressed as a girl in the mirror. I wanted to be the girl. Why did I have to put up with all the male problems I had so much a problem with. 

As I embarked down a very long path to having the courage to finally living as me, as I write about often, the longer I waited, the more baggage I needed to do away with. Often I was my own worst enemy when it came to having any success as a male as it seemed every male privilege I secured someday I would have to give it away. This extended to making any new friends. It was very difficult to be close to someone who may reject me when I set out to live a new life and let the old one go. 

At the many milestones I encountered on my gender path, deep down, I needed to choose me. Especially when I learned there would be more than one major transition I would have to take. My primary go to example was the momentous evening when I suddenly decided I was done with being a cross dresser. I wanted so much more. It was the night I went out to mingle with other professional women getting off work at a bar/restaurant by the mall I always went to. The whole process was basically a mental move, in that for the first time I was going out in my mind as a transgender woman trying to be the equal of any other woman I met. I wasn't a man at all.  It meant the world to me when I was successful and knew right then I could never go back on my journey. Somehow, someway, I just had to be me.

My main roadblock was my second wife who accepted me as a cross dresser but always drew the line at any suggestion of me being transgender. Especially when gender affirming hormones were brought up. She rightfully saw her man she married slipping away and wanted no part of it.

Unfortunately for both of us, I had gone too far to turn back on my dream of living as a transgender woman. I was following my path the best I could and did not want to go back. Choosing me, over the life I had was the most difficult decision I ever had to make. The pressure was on to make my choice and for the longest time, I tried my best to live a life in both the binary genders. Plus, it seemed when I thought I had life all figured out, more and more questions arose. Like what was I going to do about my sexuality was a big one. Was I going to pursue men or become a transgender lesbian. 

Once I made my decision, the rest was easy. The pressure was off and I was free to be the me I should have been all along. What a relief!

Trans Girl Preparedness

Image from Ben White
on UnSplash. 

Since it took me approximately fifty years to fully emerge as a transgender woman, I had plenty of time to prepare.

The challenge comes when we trans women or men need to begin from scratch. We did not benefit from a gender peer group such as other girls to have sleep over parties and experiment with makeup and clothes. No one to tell me I looked like a clown in drag. I learned I needed to resort to the mirror for help but sadly ran into problems when the mirror had the habit of lying to me. I could still look like a clown and the mirror would not tell me the truth.

What I did was go out to into the public's eye and receive an honest feedback on my appearance. In the beginning, the experience was brutal as I was met with stares and even laughter. Many times, I could not wait to go home to the safety of my own room to start over again. I kept thinking, regardless of all the negative feedback I was getting I could do better. For the first time in my life, I needed to decide what I wanted worse, to hide in my closet and not advance toward my dream of ever living a feminine life, or advance and begin the learn the basics of makeup art and fashion which at the least fit me. I found the entire process to be exceedingly difficult for me. 

Spoiler alert. I did learn the hard way what I needed to do to blend in with the rest of the women around me. It was a powerful lesson to learn when I found out how women ruled in their own worlds and how I could join in.  In the meantime, I was learning how to erase my male past and start over. To make matters worse, my male self naturally fought against the gender change to transgender womanhood he was facing. 

Through it all, I was naïve to think I was progressing towards my gender dreams. I thought that just doing my best to look like a woman was all I had to do. When I entered the wild and wonderful world of women, I was excited yet terrified of my future. After all, I was risking all of my male life as I had known it. What would become of my family, friends and income? To arrive at the point of knowing all my gender questions, I just had to be better prepared.

At that point, I started to go out into the world with a purpose to learn if I could make it as a transgender woman at all. Primary issues remained such as communication problems. Plus, I went the distance to try to stair step my way into an increasingly active public community. I purposely tried out more and more challenging situations. Away from the no challenge opportunities I was facing in clothing stores and malls. I even tried to avoid the book stores and antique malls I had become fond of but never presented any sort of a gender challenge to me. I needed to feel OK with who I was, where I was before I was able to move on. 

At the same time, my male life was successful and was pushing me to stay the same and not transition into a women's world even farther. All the struggle did was wreck my mental health. What I did not recognize yet was my feminine self was my dominate personality and needed to be freed. The harder she fought, the harder he fought. Finally, he gave up and I found a deep seated relief I had never known before.

Primarily, after all the time and effort I put into changing my exterior gender to what my inner self was always telling me, was the reason I felt better about my life. Sure, the gender affirming hormones I began to take made the transition easier also but bottom line, I was just prepared to do what came naturally and live it.  

All I Ever Knew

Circa 1940 image
of Virginia Prince

 Every once in a while I receive the question when did I know I was transgender.

The easy answer is I always knew but I needed to figure it all out. The more complex answer is I needed to figure it out after a series of transitions during my life. Two major ones occurred when I made the jump from from a very serious cross dresser all the way to a novice transgender woman. The second problem I had was back in those days, terminology to define a transgender woman or man had not yet been invented. Basically back in the pre-internet days when all we had was the preaching of Virginia Prince and her Transvestia publication which I could not wait to receive in the mail. Seeing all the pretty cross dressers just made me want to do more to improve my feminine appearance.   

I worked harder on my appearance than any thing I had ever done before and slowly began to see improvement over my testosterone damaged male body. It was all I ever knew. 

As I entered my transgender womanhood, I felt deep down inside I was doing all the right things, even though I was jeopardizing all the facets of my male life I had worked so hard to put together. What would I do when my family, friends and bosses discovered my deep secret. It ran so much deeper than just wanting to wear women's clothing. I wanted to be a woman and live a feminine life. 

During that portion of my life, I basically went into attack mode, doing every thing I could to learn how being a transgender woman would affect me. Every free moment I had, either I was out in the world as a woman or day dreaming of the times when I could. Naturally, I learned a lot, good and bad about what life had in store for me if I kept on going towards my gender dreams. I found the grass wasn't always going to be greener on the other side of the gender border as I lost all of my male privileges but hadn't gained any of the female ones. 

Soon I learned, it was truly all I ever knew. Somehow I was born to be feminine and not masculine. Which meant years of struggle to right the gender wrongs I was living. The struggles on occasion were crushing and keeping going was very difficult but I did. Probably because I was behind before I even started. I was born into a very male dominated family which had very few girls to play with. Plus, I never had any feminine characteristics myself to begin with. Add it all up, then include me never having any girl time with anyone all teamed up for a rough start for me on my gender journey.

Even still, my gender path was all I ever knew and staying on it finally made me successful. 

It is In Your Nature

Image from Hannah Popowoski on 
UnSplash

Following my fifty year battle with my gender issues, I just gave up and went with what felt so natural to me and completed my transition into transgender womanhood.

It was certainly a long drawn out journey of self discovery. It was full of ups and downs as I gained my footing along with confidence as I learned to just be myself. Looking back, I don't know what took me so long. Perhaps I can blame it on my male self wanting to hold on to the lifestyle he worked so hard to survive in. He put up quite the battle before giving in. But give in he finally did. 

When I finally began to explore the world, I learned how much of it was run by women and in order for me to survive, I needed to get along one on one with the other women around me since men rarely showed me any interest as a person. Women on the other hand were curious why I was in their world and I was somehow valued for being there. Perhaps it was my honesty showing through, which I gained from jumping the gender border into their world. I don't know for sure but I loved the attention I was getting. 

It was in my nature, because I had always valued the women friends I had over the very few men friends I ever was capable of having. I just did not fully ever recognize why until I was fully allowed to play in the girl's sandbox. Before I was allowed in though, I needed to earn my way in. I had to show my true nature was feminine and I needed to learn the rules of a brand new gender game. For example, I found myself in a world where passive aggressiveness ruled and a smiling face did not mean it was a friendly face. Much different in the world of men I was used to. It all was more of a mental game than I was used to also as I tried to anticipate where another woman was coming from. Especially when I came down to interacting with their men. On a few occasions, I came too close and felt the claw marks down my back for doing so.

The whole process just made me stronger and more confident in the woman I was becoming. Quickly I felt as comfortable in the new world I was in as I learned how the gender game was played. Women are more apt to form cliques than men who form teams and instead of finding the alpha male for acceptance, I needed to find the alpha female who was running the clique and I was in. 

Once I was in, my life became so much easier. Primarily because I did not have to fight being two genders anymore and the inner woman I was hiding for so long had her chance to run the show. She took to the process naturally. The only thing she did not do was harass me about why it took me so long for her to take over. Which she had every right to do. More importantly, I found she was a good person and got along with people including the all important world of other women. Essentially I found I good set and enjoy the show.

Of course before I could enjoy the show, I needed to understand the process of how to blend in with the world as a transgender woman. It was difficult putting my old male ego aside and realizing I was never going to be the most attractive woman in the room, I could present well enough to survive if I had the confidence to do so. 

What I really learned was, it was all in my nature to do so and if I relied upon it, I would be fine.

Engineering the Envioronment

 

Image 
JJ Hart.

As I transitioned into an increasingly feminine world, I faced many difficult issues.

I was keeping very busy with all the new sights and sounds I was facing. It was all so exciting while at the time, all so scary. Here I was trying to survive in a new gender world I so desperately wanted. Basically, with no training as I was only a very serious observer of the world of women and was never allowed behind the invisible gender curtain. 

I found out quite early I needed to engineer my own environment. Mostly, as I said, I was flying blind and needed all the help I could find. I was immersed in losing all my old male privilege's. I survived losing a good portion of my intelligence and learned how to be mansplained on many levels along with changing how I viewed my own personal security. Instead of thinking I was safe in unlighted dark spaces, I began to look for safer well lighted areas. All lessons cis-women learn at a young age. 

Once I learned I could basically dress to present properly with other women where I was going, I began to engineer more places to go to test my future into transgender womanhood.  Sometimes I was successful and other times I wasn't, mainly because I chose the wrong venue to go to. For example, bookstores were more gender friendly to me than redneck bar venues where single women rarely ventured anyhow. It took several hard earned lessons such as having the police called on me before I learned my lesson and stayed in more friendly environments . Again, experiencing what cis-women already knew. 

Ironically my journey took me to the spot some call the impostor syndrome. It occurred at all times and without notice. Such as during girl's nights out and other times when I was succeeding in living in an exciting new world. It was frustrating when the feeling slipped in which was telling me I should not be there at all. Ruining the good time I was having. 

The whole process forced me into pursuing and engineering whole new levels of my gender existence. Once I thought I had controlled everything I needed to learn to live my life as a transgender woman, something else arose to prove me wrong. Communication as a trans woman with the rest of the world who were primarily other curious women became a strong focus of mine. If I could communicate properly with other women, I had a leg to stand on to survive in my dream life, without it, I had nothing' and the time and effort I had previously put in would go for nothing. 

I was never an engineer in anything else I tried in life so all of this was new and different for me. I was also a bit of a quitter when it came to finishing a project. Completing my journey into transgender womanhood was easily the most difficult and extensive project I had ever contemplated finishing. All along the process just felt so exciting and natural, I had the best and worst times of my life as I kept on going until I reached my dream goal.

Finally, I learned the environment I was in could be trans friendly for me.  Hopefully, in the new world we are facing in the future, we can maintain it.

If You can see it You Can be It

 

Image from Trans Ohio party JJ Hart.

Long ago, when I first glimpsed myself in the mirror as a feminine person, very soon I realized just seeing myself was not enough, I wanted to be the girl I was watching. 

In the classic if I had known then what I know now, I would have known then I was less of a cross dresser and more of a transgender woman. Way before the term transgender was ever used. Now more than ever before, it is time for us to blend in with the public at large as transgender women or trans men. We just have to be better and better.

Fortunately, I had years of preparation to be ready to face the world. Since I had plenty of testosterone poisoning to overcome, there was work to be done and I needed the courage to do it. Along the way, I viewed the whole process as stairsteps towards what I perceived as an impossible dream of transgender womanhood. Facing the world with confidence was my biggest problem. Every time I took a positive step forward when I went out in the world as a novice transgender woman, it seemed then I faced several steps back. When I was on point with my fashion and makeup, I lost it with my voice. Or vice versa on other days when I caught myself slipping back into my old male ways and walking like a linebacker. Adding to my problems was I was still trying to maintain a life stuck between the two main binary genders which made my existence even more difficult. I needed to consciously think all of the time which gender I was dealing with the world as. I was in.

Very slowly, I worked through this phase of my life and found women friends who I could learn from. I learned I could relax with them while at the same time learning how it was in woman only spaces. At the time, when I looked in the mirror, I was seeing it and being it which felt wonderful and so natural I knew I was in the right place. For the first time in my life, I thought my dream of leading a feminine life could be realized.  

Through it all, I still needed to work on my makeup and fashion skills to blend in with what my lesbian friends were wearing. It was a challenge because I needed to look as if I was not wearing any makeup at all when I was. I needed to work harder than the average woman to succeed in the world. By this time, I was used to it and worked hard to instill confidence in what I was doing with my gender goals since there was so much at stake. I was playing a high risk game with my life. Was the grass really greener on the other side of the gender border. 

I found out indeed the grass was greener but often not so easy to enjoy. I met more than a few women who did not want me in their world and did not hold back on their dislike for me. When they did, I needed to quickly pull the knife out of my back, smile and move on to friendlier situations. 

By this time, I was so close to seeing my dream goal of transgender womanhood, I pushed on even harder. I started gender affirming hormones with my doctor's approval. When I did, the changes came quickly and naturally as my body adapted to the new feminine hormones. Predictable changes such as hair and breast growth were quickly proceeded by inner changes with emotions as my life suddenly became softer. With my softer skin my facial changes were fairly dramatic and I knew then I could see it and be it.

As with any other long journey, you wonder was it worth the time and effort. With me the trip from the mirror into the world and beyond was just finding my true self. 

Picking your Poison

 

Dinner with my wife Liz
on left. JJ Hart on right.

Before we get started on this post, let me repeat again and again a transgender woman's or trans man's path to living an authentic life is NOT a choice.

Somehow for reasons we are never aware of, we are born into it. At that point we are forced to pick our gender poison when we decide to follow our instincts and transition or decide to stay in our closets for whatever reason. 

Most of the reasons on either side are compelling and not wrong. Reasons include major implications include facing problems with employment, family and friends. When faced with any or all of these challenges make a closet a more comfortable place to be. Or is it? Do the problems ever go away? The answer of course is no and picking your poison becomes a bigger problem. In my case, I became increasingly caught between my own personal gender rock and the hard place. 

On one hand, I appreciated the unwanted but over appreciated male privileges I had earned the hard way. But, on the other hand, I increasingly felt natural and excited by the new feminine spirit I was feeling. The main problem I had was knowing deep down I could never go back to my male life but could not face my own truth and the process then began my poison. The longer I progressed on my gender path, the stronger my poison became and the only anti-venom I knew was to keep exploring the world as a transgender woman. I became so engrossed in my search on occasion I forgot my old male self altogether. In a short period of time I was facing cruel and unusual punishment. Mainly because I needed to internalize all my poison and the process was lonely and unfruitful. What about key questions such as my sexuality? What would my future life look like. 

All too soon, I knew my poison was also my strength. I just knew I had to stay on the path I was on to finally achieve my gender freedom. I was fortunate, I escaped my closet and was able to achieve my ultimate goal of earning my transgender womanhood. The entire process was not without stress and failure along the way. It was like I was living the ultimate trans woman's days out. I needed better times in my life just to survive in the world. Often I just was confused in how I was going to spit out my poison and achieve my dreams. As I said, I was on a lonely path and needed any light I could focus on to help find my way along. It was like I was carrying the darkness of my closet with me. 

As I was planning to go away and throw (or donate) my male clothes out, I needed to make sure I was picking the right poison when I found a trans woman's life was not all sweetness and light. Entering a woman's world meant I needed to be better than the average other woman just to survive. On the other hand, I found all the life I had lived on both sides of the binary gender border gave me more experience in the world as a whole which helped me to survive. 

In my world picking my poison and being able to escape my dark closet was the only way to go. Being a guy was always difficult for me and learning how to live as my authentic self was even more difficult but was so much more natural and enjoyable. 

Reaching Out for Truth

 

Image from Jen Theodore
on UnSplash.

As I transitioned into my form of transgender womanhood, first I needed to find my own truth. In order to do it, I was placed in a dilemma. 

The dilemma was I needed to make sure my gender journey was taking me in the right direction. I needed to make a huge life changing decision so I needed time and experience to make certain I was taking my life in the right direction since essentially I was risking everything to do it. In other words I needed confidence. 

Gaining confidence proved to be a fragile thing to find. I would have it following a successful day out away from the mirror as a novice transgender woman when I seemed to do everything right. My makeup, wardrobe and wig were on point and I even carried myself fairly well. I was building the life I always had dreamed of and seemed to be within reach until the next time I went out and everything crashed and burned. Either I did something very unrealistic and was laughed at or my overall appearance just wasn't right. Whatever the problem was, my fragile confidence was shattered. And, as we all know, confidence is our most powerful accessory. Humans are similar to sharks, if they perceive something is wrong with you, chances are the other human could act on it. A big turning point for me was when I arrived at the point where I did not care what anyone else thought of me. 

Actually, let me re-phrase that. I did not care what men thought of me because for the most part they had all felt as if I was from another planet anyway and wanted nothing to do with me. On the other hand, I did care what other women thought about me. Since I needed other women's acceptance to exist in the same world they were in, I needed their approval. In order to survive, I needed to be honest to myself which in turn, made me honest to them. I was not hiding anything. I was upfront on what I was trying to achieve which was to give up my old life as a man. Very quickly I learned I appealed to more women as a friend than I ever had as a man. I thoroughly enjoyed my learning curve as a transgender woman and wanted to build on my truth even more.

Even still, on occasion, I was still having issues with living my truth. My biggest hurdle to conquer was myself. I was the last to know my truth because I hid it all so well. To my everlasting shame, I even lied excessively to my second wife about what I was really doing while she was working at night. So, by osmosis, I was lying to the two closest people to me. Something I am certainly not proud of. However, I am proud of the fact I did reach out and grasped my truth during my long life. 

It took me long enough to do it. I struggled for over fifty years as a cross dresser and went through so many stages of attempting to figure out who I really was. I was so much more than a man who liked to wear women's clothes, I wanted to be a transwoman wearing women's clothes. Once I learned this major truth about my life, finally everything came into focus. 

It Was Never Easy

I am amused when anyone thinks my gender journey has ever been an easy one. 

To begin with, I was born into a very male dominated family. Being the oldest son of two, I had heavy male expectations forced on me. Very early on, I learned I was in the wrong place at the wrong time. I did not belong in the male world at all. The problem was coming to the knowledge I did not belong as I was sneaking around my family's back to cross dress as a girl. As I remember, I had two hiding places for my small collection of feminine wardrobe and makeup. 

The first place was up in the attic of our family garage and the second was more creative when I discovered a hallowed out tree trunk in a woods next door to my house. What I did was use plastic trash bags to protect my precious belongings from the elements and it provided an extra way I could be alone and dress which relieved (for a day or two) my gender tension. So none of my drastic measures were easy but I survived without anyone detecting my secret, to my knowledge. 

As years went by and my life as a girl began to be more complex, I was pressured to do more and more to protect my life. Sneaking around became more intense as my wardrobe increased, along with my knowledge of the makeup arts. In all fairness to me, I attempted to ease my gender pain, I told my first and second wives ahead of our marriage I was a transvestite or cross dresser which I thought would help my world. My idea worked for awhile, until I essentially out grew the idea I simply wanted to wear women's clothes and makeup. More and more I wanted to be a woman.

Making the jump from cross dresser to transgender woman often was brutal. Partially because I still had my male life to contend with. It probably would have been easier on me if I was not involved in such a male intensive job which automatically would completely throw me totally and publicly back into a world I never wanted. Ironically, my life as a man I worked so hard to build was now in direct competition with a feminized life I was growing into. 

At the same time, my biggest challenge became was deciding if I was transgender at all, Could I continue a life where I lived in both binary genders temporarily or would I need to choose between being a man or a woman. I ran from the decision for years before I grew so tired of running I could go no farther. Making a decision was never an easy one but one I needed to make. Finally, one night I had yet another soul searching discussion with myself and decided to live a life as a transgender woman. The world as I knew it was showing me the way. For the first time in my life I was single and did not have to worry about a spouse to deal with when I changed.

I went even further and decided to go to a doctor to see if I was healthy enough to begin gender affirming hormones. I was and my body took to them very rapidly, making my decision to give away what was left of my male wardrobe to charity and add to my feminine wardrobe. It was not easy to make the decision but it was easy to live with the results. I only knew my new feminine life would never be easy but still would so much better than the life I had lived,

It was never an easy life and my gender dysphoria certainly did not make it any easier. Waking up in the morning after dreaming if I was a boy or a girl never got my day started on a good foot. All of it became some sort of a daily routine I never wanted. With all the highs and lows, somehow I learned to live with it all. 

Welcome to Reality

Out with my girls. Liz on left, Andrea on
right.

I worked very hard to get to the point where I could live as a transgender woman. 

Once I began to arrive, I understood the real work was still ahead. When I finally began to establish myself as a new person, I needed to start all over again. It primarily affected me when I was in a conversation with other women, since men barely talked to me at all. Main examples came when I was invited to several girl's nights out. I learned to interject my family experiences in the older group of women. Instead of saying I was specifically a mother or a father in my life, I said I was a parent to a daughter I was very proud of. By doing so I was able to become an active participant in the give and take women use to communicate when there are no men around. 

It was all a great learning experience for me as I was building my confidence to stay out in public and slip behind the feminine gender curtain. For the most part, I found acceptance except from a few women in the older group who did not accept me. All the younger women did accept me for who I was and I enjoyed going out with them immensely. Since they were all younger and more attractive than I was, they attracted all of the attention, leaving me basically to fend for myself which was fine. It was only the reality of being in the feminine world setting in. 

I also had to deal with a big dose of impostor syndrome when I went behind the gender curtain. I needed to keep telling myself I belonged with a group of women while I was doing it. Following many battles with myself, I finally came to the conclusion even though my path to womanhood was different than most of the world, I still followed a difficult path to arrive where I wanted to. Plus, I needed to remember, being born female did not necessarily entitle a person to being a woman. It was a social title not a biological one. When I arrived at that point, the reality of my situation was easier to understand.

The more I worked on the new me, the better life became. I felt natural when I slipped behind the gender curtain and for the first time in my life, I could say I was happy. Mainly because all of the gender tension I felt attempting to fill an unwanted male role was over. Understanding all the differences between the two main binary genders was never easy but for the first time in my life, I attacked a problem head on and did not try to run behind makeup and a dress to escape. I was the one in makeup and a dress and I had to make it work.

I was fortunate in the fact my inner feminine soul had been watching and learning all along. She was just counting the days until she could take control and quit fighting my male self for domination. Once she was free, activities such as girl's nights out were just icing on the cake. 

Once I discovered my feminine reality and was able to live my truth as a transgender woman, life was so much easier.

Quickly, on another topic, I have decided to go to another LGBTQ Veterans support group meeting coming up soon. I have been to two now and they have been tolerable. The only real problem I have had is explaining what I did in the Army because I was in the American Forces Radio and Television Service. A very small segment of the Army. So, you needed to be deployed overseas to be exposed to AFRTS at all anyhow. During the last group meeting, I think I at least was able to explain what I did in the service and I was in way before "Don't Ask, Don't Tell" military LGBT policy was in effect. It is all so difficult to explain but the moderator seems to want me there, so I am on the week to week participation plan. Past that, we shall see how it goes.    

  

It's All a Big Transformation

Image from Ross Findom on UnSplash

Before we get started, I need to take a moment to remember the surviving military members of the D-Day invasion. It is important to remember how we arrived at the point of having to fight such a monumental war at all and hopefully learning our lesson to never do it again. My Dad fought in WWII but was not in Europe for D-Day. 

Now, on to the post: Anyway you look at it, life is nothing but a big transformation. We are born into a certain gender (right or wrong) and have our opportunities to grow into men or women. Not just males and females because it is a socialization process. Sadly for transgender women or trans men, we go through extra transformations in our life. Mainly because we need to escape from the initial gender declaration we were straddled with when we were born. Being forced into square gender holes when we were born as round pegs is cruel and unusual punishment. 

Over time, if we are lucky, we are able to climb out of our gender closets and thrive in the world but to get there, often it takes several separate transformations to arrive at our goals. For example, the first transformation I went through was when I was able to look at myself in my Mom's clothes in the hallway mirror. From there, I went even further by raiding her makeup and basically looking like a clown before I improved. At the time, I compared my expertise to painting a model car which were so popular at the time. It took awhile but I did get better with both at the same time. With no guidance from anyone, I needed to start from scratch.

Along the way, somehow I did manage to catch up partially with other girls of my age who I was watching closely. Another problem I had was having any income at all to purchase any feminine items of my own because I was rapidly out growing all my Mom's clothes so I took on a news-paper route to augment my meager allowance and buy a few items. In order to do so, I needed to visit my Grandma who lived very close to the downtown area which back in those days was a thriving business district. I snuck out, spent my money while being scared to death I would run into my Dad who worked nearby. Then sneak all my purchases back home and into my regular hiding places. By doing so, I was helping my transformation along.

The older I got, the larger my transformative steps became. Starting with going to Halloween parties dressed as a woman and then sneaking out of the house cross dressed, I knew each time I was successful, I could not go back to my unwanted, boring male life. Yet I needed to because I was still the round peg struggling to get out of her square hole and enjoy an authentic life as a novice transgender woman. Most importantly, it was looking as if I could defy all odds and do it. All because of the evenings I went out as a trans woman to be alone and ended up socializing with the world. Granted, it was a huge transformation to climb out of the male life I was in and make it into the dream world of women I always wanted to be part of but I made it.

Perhaps the biggest transformation came when I began gender affirming hormones. In addition to feminizing my body, I also feminized the world as I saw it. Finally I didn't have to play the old macho male game and was able to cry when I needed to. Surprisingly to me, my body even became more sensitive to changes in temperature and smell as my world softened.

I look at myself as being so fortunate in that I lived long enough to sense and go through several big transformations in my life. All the way from being able to father a child I love to living a fulltime life as a transgender woman with a woman I love, in many ways I feel I have received more than I deserved.  

Transgender Stairsteps

Image from Reinaldo Kevin
on UnSplash

As I progressed through life, the idea of me being transgender took up more and more space. 

When it did, I had to create my own steps to arrive at the next level and negotiate all the many stop signs which impeded my progress. For awhile, I was so engrossed in my own appearance, my second wife called me the "Pretty, pretty princess." Mainly because she did not use much makeup and was not very girly herself. I did get my revenge on the occasions we were going out and she had to ask for my assistance with her makeup. It was all I could do to not say something like did she all of a sudden need the "Princess's" help but I didn't.

Little did I know, presenting the best I could as a cross dresser or novice transgender woman was just the beginning. As I was attempting to learn as much as I could about the next step I was stonewalled by my wife who did not want me to go any farther as a trans woman. Not to mention my male self, who was doing his best to derail my gender journey the best he could. It was obvious, he wanted nothing to do with giving up any of his power over me. 

With or without either my wife or my male self, my path was set and I was intent on finding and climbing the next steps towards living as a fulltime transgender woman. Now I shouldn't get  too far ahead of myself because of all the steep stairsteps I still had to climb. The first step was to determine exactly what my gender identity was. Which included my all important sexuality. Since I was planning on living a feminine lifestyle, would I be expected on changing my sexuality as well. This time of my life was very exciting and scary at the same time. When I made it to my next step, I needed to maintain my balance before I could even think about going forward to another.

Once I maintained my balance and was able to look around in my new feminine world, I loved where I was and could not wait to go on. After all, I was showcasing my new skills at blending in with other women as well as experiencing more and more communicating with other women which I went into in yesterday's post. I can safely say my communication experience was one of the most difficult things I had ever done. The next step seemed to be an impossible distance away. Somehow I made it anyways and the next move was seeking out the availability of gender affirming hormones or HRT. I did get approved by a doctor to begin the hormones and the next step was a huge one. Mainly because I had some sort of an idea of the physical changes I would be going through but had no idea of the internal ones.

All of a sudden, I was a different person. I could cry when I never could before as well as undergoing other inner changes. The step of hormones turned out to be worth the wait and all the anticipation. In fact being afraid of heights and climbing too high was worth it also. Maybe it is the excuse I can use to rationalize to myself why it took me so long to realize my transgender life long dreams. 

Before I go, I would like to wish a Happy Birthday to my oldest Grandchild who is graduating from The Ohio State University in December. My Grandchild also happens to be trans and identifies as "They/Them" and I am so proud!

It was All so Natural

Image from the Jessie Hart Archives. 

Even though I was facing tremendous hurdles as a cross dresser and/or novice transgender woman, everytime when gender times became tough, I kept on trying. Mainly because deep down  I felt so natural when I was cross dressed head to toe as a girl my age.

Although the time I was cross dressed felt so good, the length of time I was able to do it was never enough. Had I had more knowledge back then, I would have realized I was a transgender person. A big difference to me from only being a part-time male who enjoyed cross dressing in women's clothes. As I discovered more and more about myself, I discovered I was a woman cross dressing as a man during the majority of my life. I only knew I was not enjoying or was being fulfilled as a guy. The whole lifestyle never felt natural to me. 

As time went by, I increasingly followed the natural path no matter how difficult it proved to be. More often or not, I encountered very many severe twists and turns. Again, I was encouraged by the natural moments I experienced when I finally encountered the public as a trans woman. It was like the path had big sign boards along the way with directions on how to proceed. Or once I made it to a certain spot in my new gender life, I could set new goals. The example I always use was when I started to progress past just going shopping in clothing stores where they didn't care if I was a man dressed as a woman or not (because my money was green) and began to challenge myself in restaurants where I needed to interact one on one with the serving staff.  

From there, my goals became to refine and test my restroom skills if nature called during one of my longer outings. It was during some of my restroom visits when I  really needed to feel natural and spread my gender wings. I found out quickly I needed to be able to look other women in the eye and smile even though I was very scared. 

Through it all, I lived and was able to move forward towards new enticing goals of living life as a transgender woman. It was during this period of my life when I began to seriously consider moving forward with gender affirming hormones. Sadly, my second wife was very much against any idea of me being on hormones saying if she had wanted to marry a woman, she would have looked for one. In other words, she didn't sign up to live with another woman, trans or not. I loved her deeply and no matter how difficult it was, I tried to honor her wishes until her untimely death after we had been married twenty five years. 

Her rejection of any idea of me moving forward with HRT just put an extra strain on my mental health which in turn, led to a suicide attempt. Following the attempt, I tried yet another "purge" of my feminine wardrobe which of course didn't work. It wasn't too long after my final purge, she passed away very suddenly from a massive heart attack. As I write about often, her death was the ultimate shock to my system because I was always so self destructive there was no way I thought I would out-live her but I did.

When I did, I decided it was time to live my dream of being a full-time transgender woman. I took the natural path and never looked back.  

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.

Un-Common Risks as a Trans Girl

Liz on left. Date Night. 

Most people undertake a risk or two as they make their way to the undertaker in the end. 

When you come right down to it, which person you chose to marry is a risk as well as which profession you choose. Transgender women and trans men seem to have an added layer of risk in their lives. Along the way as we pursue a gender transition, we have to make many difficult choices which aren't really choices at all. They are paths we have to follow or face devastating self harm to ourselves. Which results in extremely high suicide rates in the transgender community. 

When we are growing up in a world where our families often don't accept us, the entire process makes the risk factor even more important. I am so blessed to have a daughter who completely accepts and supports her transgender child and I am proud to have been a role model for my grandchild to follow but it wasn't easy. 

When it came to my marriages, seemingly destiny has led the way into several different areas of acceptance. Acceptance of course led to risks being taken. My first wife was very easy going and knew of my cross dressing desires before we were married and had our daughter who turned out to be my only child. My first wife accepted without question my desire to cross dress as a woman and venture out on Halloween adventures. I often thought if I came home from work one day and told her I was checking into a hospital for gender alignment surgery, she would have said that's fine, just be careful. As it turned out, I was not ready for that sort of surgical risk and would never be.

Then destiny threw me a curve ball with my second wife. The moment I saw her for the first time, I knew I wanted to be with her in the worst way. Even though she too knew I was a cross dresser, she still restored feelings I long ago had forgotten when I was ready to compete with another man for a woman. In order to win the competition I needed to divorce my first wife and move on to a totally different strong woman who knew somewhat of my gender issues. I say somewhat because back in those days I was just learning myself how deep my transgender feelings ran which were to cause strong problems in our twenty five year marriage later on after the newness wore off. From the start, I always thought she would be the one who would help me to break through in my cross dressing world and help me to be successful in my dreams. As it turned out, she wasn't that person and always drew the line if I suggested at all I wanted to go further into the transgender world. By the time she had passed away, our relationship had deteriorated into an ugly cat and mouse game of me taking risks and seeing what I could get away with.

Another main risk I took was with my job. Slowly but surely I had been promoted through the managerial ranks to a successful position as an executive general manager of a big popular casual restaurant chain. A position with a company I knew would not accept me transitioning into a transgender woman. In my haste to destroy myself anyhow, I began to go to my competition as a woman thinking no one would recognize me. Well, I was wrong and the roof began to fall in on me. It was tough but I denied all the rumors and kept on going.

By this time, my second wife's life was coming to an end and she suddenly without warning passed away from a massive heart attack. By this time I had purchased my own restaurant and was somewhat in control of my own financial destiny until a recession in the Rust Belt where I lived wiped out the population. I ended up losing my restaurant as well as my inheritance by taking a major risk and losing nearly everything I had. I finally was able to find me a fast food job to hold me over till I could take an early retirement from Social Security and sell vintage items my wife and I had collected over the years. Between the two I survived.

I then found myself in a period of wonderful gender discovery, when with the help of new women friends everyday seemed as if I was reborn. Specifically Kim and Liz helped me the most. Liz lived in nearby Cincinnati and we met on line. After corresponding by email  for months, I finally became brave enough to talk to her in person and our first date was at a drag show. That date was nearly twelve years ago and we are coming up on our second anniversary of marriage. Liz cemented her place with me when she told me she had never seen a man in me and why didn't I finish my transition into a feminine world with her.

Finally, after a half century of wondering and suffering over my gender dysphoria, someone else recognized my truth and wanted to accept it with me. My un-common risks were over. I accepted her advice, gave away my male clothes and never looked back.

It Was so Much Larger than I

 

Jessie on right with Tom
from the image archives.

Back in the so-called simpler days when I was growing up, putting on a dress, adding makeup and acting like a girl was quite the rush. The mirror meant everything to me and I couldn't wait to show myself out to it again and again.

It took me awhile to grasp the idea I wanted to do and be more than just a girl in the mirror. I wanted to be the girl. It was my earliest fundamental idea I was so much more than just a casual cross dresser, if the knowledge had been available to me, I would have labeled myself as transgender or at the least gender fluid. Bottom line is however you want to label me, the whole process was so much larger than I was.

From that point on, anything I did in life was predicated on my gender dysphoria. Each person I decided to establish a friendship with, I needed to wonder if they would ever accept the feminine side of me. The whole process led me to be very standoffish with most strangers and developed very few close friends. Of course the idea of marriage became a huge obstacle. I knew I wanted female companionship but did not know if marriage could ever be possible for me. The end result to any relationship could ultimately finish because of my gender issues which made me wary of knowing anyone. 

Eventually, I was able to work around many of my gender issues and my world broke open once I was in the military. It was there I met my first wife and future mother of my only child. She was unplanned since I was out of control in my life as I busily went about running from my problems. Becoming a father turned out to be so beneficial to me as it settled me down and I figured I could put off telling her her father was really a second mother of sorts. 

Through it all, I tried my best to keep running from my gender dysphoria. Mainly from abusing alcohol, changing jobs and moving homes. I became a gender survivalist. Still being very careful around strangers and keeping up my well crafted male persona. It was working as well as could be expected until I met my second wife. She knew I was a cross dresser from the beginning so I thought I had it made, a strong woman who accepted my feminine self. What I did not factor in was again I was more than a cross dressing man, I was a transgender woman lying to herself. When she married me, she made it clear she wanted nothing to do with living with another woman. A fact which would come back to haunt me totally in the future. 

My second wife and I managed to navigate a very complex relationship for more than twenty five years before she passed away. Sadly, during her life, I became increasingly active as a transgender woman and ended up cheating on her with another woman, who turned out to be me. As I was continually lying to myself, I was creating major problems for our relationship and my mental health. After she had passed on, I finally met my wife Liz as well as other female friends who convinced me my life as a trans woman was not larger than I. The more I emerged into the world, the more I understood my feminine inner soul was always the dominant person in my life and she was more than ready to take over. The easiest way to explain it was it all felt so natural when she was calling all the shots in my life. 

Little did I know, the half century I spent exploring my cross dressing world was little more than a huge build up to a new exciting larger life.  

Being Prepared for a Transgender Future

Image from Chad Walton
on UnSplash.

For nearly a half a century, I hid behind the idea I was nothing more than a cross dresser who liked to wear women's makeup and fashion. What harm was I really doing? The answer is, the only harm I was doing was to myself.  

Had I known all I was doing was to prepare myself to transition into a transgender woman later in life, I may had approached the process in a different light. The problem was, everything seemed to be so life and death serious. Primarily since I was locked into a very lonely, dark gender closet. I had no role models around me to prepare for a highly uncertain future. No one to tell me my make up looked clownish and my skirt was way too short. I only had my old male ego and a mirror who were teaming up to make my life miserable. 

I really learned how miserable I could be when I began to leave my closet and explore the world.  Being stared at and laughed at to my face taught me the mirror could lie to me and the way my old male self was telling me to dress was all wrong. I was going back to my cross dressing drawing board too many times before I learned what I had suspected all along, becoming a part of the feminine gender was going to take a lot of work. I needed to go so far to finally understand all along I was a woman cross dressing as a man and not the opposite. 

The more I began to understand where I was in life, the more the future came into focus and preparations for major upcoming decisions became important. As I was exploring and building a new life as a novice transgender woman, it became clear to me I could indeed live my dream of living as a woman. Before I could arrive there, I still had heavy preparation work to do. There were major issues of coming out and telling what was left of family and friends I was a trans woman. Once I did, there would be no more running home and hiding in the mirror wearing a dress, The first person I told was my only child (my daughter)  went very well and I was emboldened to tell more people such as my only sibling ( a brother). He accepted my transness terribly so I ended up with an even split in salvaging any of the family life I had left since my parents had long since passed away.

The next crossroad I needed to navigate was what was I going to do about supporting myself in my new world. Following quite a bit of planning and preparation, I decided I was close enough to being able to take an early Social Security retirement which back in those days was sixty two. To get there, all I had to do was work another two years. Ironically, during the two years, I was able to prepare even further for my future when the Veteran's Administration Health Care System I was part of suddenly began to accept HRT or gender affirming hormones for veterans. So, the extra two years gave me the time to further prepare for a future which included changing all the legal gender markers I could including a new legal name. 

Since I was newly single again following my second wife's sudden passing, I really could use the time to prepare for the final transgender transition into a new life I had been preparing for since I was born.  

Close Encounters of the Transgender Kind

 

Image from the 
Jessie Hart Archives.

Very early in my life, similar to so many of you, I suffered many close calls when it came to being caught in my feminine clothes by my younger brother or worse yet my parents. 

As with most inquisitive younger brothers, if I was out of his sight for any length of time, he wondered what exactly was going on. To make matters worse, we were just a couple of grades apart at the same school, so we rode the same bus home and arrived at the same time. Leaving me very little time to cross dress and admire myself. I even had to hide out in the woods when the weather was good to dress up.

My parents were partially a different story. My Dad was a banker and Mom was a high school teacher, so they arrived home usually in time to sit down to dinner. If you remember those days. My point being, seemingly for weeks at a time I couldn't find a way to explore my gender closet at all and the pressure to do it just increased to the point of no return. Which meant I needed to take risks. We had two bathrooms in our house and sometimes I could barricade myself into the one which contained most of my Mom's makeup. When I combined her makeup with mine, I had plenty to experiment with. 

On the exceedingly rare days I was left all alone, I went all out. Even to the point of being able somehow to get away with shaving my legs. I was completely in love with how wonderful the air felt on my freshly shaven legs when I took the chance to walk to the mailbox which was some distance away. No matter how good I thought I looked, the biggest problem I had was with my hair. In those days, I was stuck with either the ultra short burr haircut my Dad had or the equally as bad crew cut. A wig of any kind to me in those days just seemed like the impossible dream and it wasn't until my college years when I could afford to buy a nice wig I cherished for years. I even hid it, as well as other cross dressing necessities away when I went away to the Army. Hoping they would not be discovered. They weren't. 

Even with all my precautions, I still ran into the times when I had to hurriedly wipe the makeup off my face and change my clothes when my parents came home early. I don't know how but I somehow survived without a gender confrontation which would have been a disaster. At the time, I thought when I became older I would have more control over my cross dressing desires and life would be better. In no way did I feel as if all of the sudden I would wake up with no gender dysphoria and life would be much better. On the other hand I still felt I would not have to hide my true self to others. To compensate, I developed a very macho exterior self and avoided making very many friends who I may have to come out to later. A process I would come to regret later in life.

It turned out, mainly because of my wanting to not come fully out as a transgender woman, hiding away my true self from a loved one would reach new heights of desperation. The loved one I am referring to is my second wife who knew from the beginning of our relationship I was a cross dresser and accepted it. Everything in our relationship was good until I finally faced the truth of me being transgender, which my wife soundly rejected. Increasingly, when she was working nights, I was out exploring the world as a trans woman to primarily see if I could make it or not. When I found I could, I began to go out more and more which led me to having more chances of being caught. All of which led to huge fights when I came home as my feminine self and she was waiting for me. It was like I was a kid again and resented the process completely but it was like a train wreck waiting to happen.

Our relationship became so strained, my wife told me things like why didn't I just man up and live as a woman. A great point which I never did while she was alive. Somehow, it was similar to me trying a last gasp attempt at saving what was left of my manhood at her expense.

When she did unexpectedly pass from a massive heart attack, at the age of sixty, I finally was able not to worry about any close gender encounters. I had paid my dues and was so happy to fully come through an often very uncertain life and live in the world as a fulltime transgender woman with no negative people in tow. A dream I thought I could never achieve.