Should You Be a Jumper?

 

Image from Jeremy Bishop
on UnSplash. 

As we go through life, many of us have chances to jump and try to improve our status. 

As I lived, I certainly registered in the jumper category. I have no idea if many of the decisions I made concerning employment changes and resultant family moves had anything to do with my gender issues, but I always assumed they did. What if I was trying to just jump and hide from wanting to live a feminine life and escape the old male one, I was forced to live. 

The one thing I did learn relatively early in life was I did not have to put up with seemingly huge obstacles put in front of me. The biggest example was when it became obvious, I was going away to serve my country during a very unpopular and deadly war in Vietnam. Immediately, since I worked for a congressman's radio station, I sought out help to work in a very small section of the military...American Forces Radio and Television. I thought, why not try and see if I could pull off a miracle of sorts, so I went ahead and jumped by sending off letters to Washington, DC. Amazingly, I received a fairly positive letter back and went on to eventually landing a spot on the network. So, jumping really helped me, and actually spoiled me for the near future.

When I was discharged from the military, I played around for a while and ended up on a cross-country car trip with my future first wife and mother of my only child. Since we were driving from my home in Ohio to her home in California, we covered many miles with side trips to visit friends in Texas and Seattle. It was fun as my fairly new Chevrolet Vega held together well enough to make the trip. And all the jumping helped me to briefly forget all my gender issues. 

When we returned, I pooled together my savings with a friend and bought a small neighborhood tavern in my hometown. It was quite the jump as my dad described it best as a place which had two doors, so the Flys did not have to stop when they went through. Even though dad's opinion spoke for itself, we worked on the tavern and finally made it a success when we added homemade pizza and deli sandwiches. Sadly, I destroyed all of my hard-earned success because of excessive alcohol abuse, and I lost the whole operation. 

Ironically, I did not learn my lesson with restaurants because later on in life, I quit a very good commercial chain restaurant job to risk a fairly sizeable inheritance I inherited when my dad died. This time, due to a severe economic downturn in the town I lived, I lost the whole gamble after about five years. Proving once and for all, my jumps did not all turn out well. 

Later on in life, I blamed much of my dependence on alcohol as just a way to jump life and not have to deal with being a transgender woman. Even still, I was far from finished from jumping. As I began to go public as a novice trans woman, I learned I could actually live the dream life I wanted. To do it though, I would have to jump through a set of very serious hoops to succeed. What would I do with the fairly successful male life I had worked so hard to succeed with. When each of us considers a total gender jump to the other side, we have to wonder what will become of our family, friends and employment. Rather than considering the process as a jump for me, I always thought of it as sliding down a steep gender slope towards a cliff of unknown depth. 

Regardless, I gathered all of my courage and put my male life behind me. I gathered up all my male clothes and gave them to the thrift store and set out with my gender affirming hormones into an exciting new world. 

In the world of transgender women and transgender men, it is extremely difficult to advise or give much guidance to each other. Frustratingly, many trans people share the same path but on the other hand don't. It shows up in the maddening ways we can't seem to truly unite as a strong "T" under the LGBTQ umbrella. It is difficult for all of us to jump together. I can't say you should be a gender jumper or not. It has to come from deep inside you.

Preparing for the World

 

JJ Hart. Witches Ball Image.

Before we get started, I would like to take the time to respond to a comment from an anonymous reader to the blog.

For the sake of simplicity, I will condense the comment. The reader was responding to my post concerning my second wife never accepting my feminine self. The reader raised the question about if my wife was somehow jealous of the way I looked. Even though my ego often considered it, I never allowed myself the latitude to consider it. After all, I never considered both of us were in any sort of a competition when it came to appearance, we were simply different in our outlooks. As a cisgender woman, she believed in very minimal makeup and conservative clothes. I did not, and considered the makeup, hair and wardrobe process a woman goes through as part of the fun and challenge of being femininized. As it turned out, there was no way I could cross dress down to her level. If I did, I might as well not attempt it at all. As all of your regular readers know, I will never have a final answer to the appearance question because she passed away years ago. Thanks for the comment and now on to the rest of the post.

I found, as I evolved in life, it became more and more evident to me that cross dressing was more than the proverbial "sun" of my life. What I mean is, even though my entire life revolved in many ways around being a serious part-time cross dresser, deep down I knew I had so much more to accomplish in my gender journey. 

To arrive at where I wanted to be as a novice transgender woman, there was so much more I needed to do. When I put my so called "pretty, pretty princess" into motion into the world. No longer did I just have to worry about my appearance, I had to concentrate on how I was moving and communicating with the world. To say the least, it was a struggle to put all aspects of being a novice transgender woman together. My sun became my entire universe as I went out into the world as I attempted to completely feminize myself. I needed to stop with the ignorant way I was trying to present myself and learned the hard way, to survive in a world I found was run by women, I needed to be better. 

My brutal entrance into the world as a transgender woman, helped me to learn all I needed to know. Or so I thought. Every time I thought I knew where I was headed, only to find I had another wall to climb. Finally, I came to the conclusion in life, there would always be walls to climb and my life as a transgender woman prepared me to better attempt the climb. 

Since I was/am very afraid of heights, I could not spend much time enjoying the view when I had successfully climbed a wall. I needed to get busy and search for the next one. Plus, having a soft landing was never guaranteed. No one ever told me how many bruises I would suffer on my path to gender freedom. 

Finally, any purported competition between my second wife and my inner feminine being was put behind me and I could move on the best I could. 

Born This Way

Image from Vonecia Carswell
on UnSplash. 

 I had no choice; I was born with gender issues which I would have to deal with my entire life.

It is also International Women's Day, so in many ways, the gender issues I did deal with intersect with each other. Along the way, I have received pushback about saying I was a woman at all which I understand. At first, the transphobes attacked me with the old broken argument that I could not be a woman because I could not birth a child. I simply pointed out, many females for whatever reason cannot or choose not to have children. Their choice certainly does not make them any less of a woman.

So, how can I claim Women's Day as my own? Mainly because I worked so hard to gain my transgender womanhood and it should be included with every woman everywhere. At the least, I can provide unique perspectives on my life. Trans women everywhere are fighting now for their very right to exist as women and should accepted as such. In fact, I had some good news-bad news from the VA where I obtain my gender affirming hormones about my future availability of the meds. In my Veterans Administration LGBTQ support group meeting yesterday, the moderator passed along the good news about the long reach of the current felon's administration. The good news was there would be no changes to transgender care, but the bad news was, it said for now. We all know that is not good news. In the meantime, I received my new shipment of estradiol patches this week along with three refills which are plenty to hold me over to my next endocrinologist visit in the early part of May. 

Back I go to the subject at hand. As I always mention, transgender women never had the girl's workbook to benefit from. We never had on hands advice or guidance from our mothers or from the other girls around us. We were left on the outside looking in. What it meant was, we really had to hit the ground running when we came out into the world, we had a lot to learn. Lessons in femininity were often swift and brutal. As I survived mine, I earned my way into celebrating International Women's Day and you should too. 

I sense from the comments I receive here on the blog; I have a wide range of readers from weekend cross dressers, all the way to post operative transgender women. The only point I am attempting to point out is, no matter where you might be on the gender spectrum, you still matter. None of us have a crystal ball telling us the future. For you cross dressers, sooner or later, you may have the chance to open your closet door and live a life you possibly just dreamed of. As I found out, never say never is a good quote when it comes to a possible later in life gender transition. Along the way also, I learned I had tons of knowledge of the world I could offer to other women. Because of my life masquerading as a man, I have a leg up on demystifying the male world for other women.

Even though transgender women may be the underdogs in the overall women of women, we belong in celebrations such as International Women's Day because we were born this way.

I Was Ready but Was the World?

 

Image from the Trolley Stop, Dayton, Ohio

It took me years to understand and accept my transgender womanhood, but once I did, what was the world going to think.

Once I had worked very hard to cross the threshold into being able to put a reasonable effort into presenting as a woman, the difficult work started. Even back in those days, I was able to learn basic tricks to take a good-looking picture but then I found putting the picture into motion was the problem. The whole scenario presented me with big new challenges, The largest mistake I made was underestimating how quickly the world would want to communicate with me. All of a sudden, when I was going out to be by myself, someone (usually another woman) would invade my little world. Which was suddenly growing rapidly. Initially, until I grew used to it, just trying to look another woman in the eye and talk to her was a real challenge.

I started by merely trying to mimic the tone and sound of the person I was talking to, then took femininizing vocal lessons to aid my efforts. I discovered quite quickly, I was more ready for the world than I thought. I found putting too much effort into communicating with a stranger could be a turn off and too little interaction could come off as being bitchy. So, I needed to be careful and usually let the other person lead the conversation. 

For the most part, I found the world was ready for a stray transgender woman just learning her way. I even was able to converse with several other women I met regularly in venues where I was a regular and so were they. I was amazed I had such an easier time talking to them woman to woman than I ever did as a man. One venue in particular in my world was a tavern called the "Trolley Stop" in Dayton, Ohio. It was/is the oldest continuing tavern in Dayton and I quickly became a regular of Gabby the daytime bartender. I knew from previous experiences, having support from the bar staff was key to my overall acceptance. So, I did my best to be friendly, spoke only if I was spoken to, and tip well. Being accepted in the Trolley Stop helped to really expand my world as a transgender woman and prove I was ready to do it. To make matters even better, the Trolley Stop even hosted a lesbian mixer every month or so and I enjoyed good times there as well. 

All of a sudden, the more I was out in the world as a trans woman, I proved I was ready to make it completely in the new universe I was in. It turned out to be one of the most exciting and satisfying times of my life. I was interacting and communicating with others. When I did, I made a whole new circle of friends (mostly women) I write about frequently. They provided me with the building blocks I needed to find my gender dreams. Once I had the solid foundation I needed, the rest was easy and fulfilling. Especially to my long hidden inner feminine self who had been punished for my entire life.  

  

Real Life Impostors

JJ Hart at Key Largo.

 At various times in my life, I have suffered from impostor's syndrome when I was out with other women celebrating a girl's night out.

While I was overjoyed to be invited to the events and considered them to be a rite of passage to my transgender womanhood, I still could not shake my underlying feelings of doubt when I was allowed behind the gender curtain. 

As I went through the process, I began to wonder if all human beings go through a form of impostor syndrome in their lives. What I am trying to say is no woman is born a woman. They are socialized through life to achieve the status of women since they were born female. Men also go through the same process. It's the primary reason I had such a difficult time leaving my male past behind because in many ways I had made it to manhood which was miles away from just being another male. I needed to start all over again to travel to my gender goal of transgender womanhood. 

In the meantime, my confidence was building that I had as much right as the next woman to be at special functions. I had just arrived at the same point the other women did by using another path. I was aided also when I calmed down and began to contribute more to the group. I found I had more in common than I thought in this women's only space. Even though, I most certainly did not birth a child, I could bring up my own daughter and grandkids who I was so proud of. I just needed to flip the gender script to relieve myself of any possible impostor syndrome feelings. 

It wasn't just at the girl's nights out when being a gender impostor took a hold of me. Another prime example were the nights when I felt I was doing everything right. My fashion, hair and makeup all were on point and yet there I was wondering what I was doing there at all. I was devastated when I had come so far in my feminine presentation, just to have something else stand in my way. It took me awhile, but I worked my way through it all and put impostor syndrome in my rear-view mirror.

On the increasingly rare occasions when I encountered any resistance from the public, I finally came to the conclusion they were the true gender impostors. It was very clear to me why men left me alone as they were so insecure in their own sexuality. On the other hand, most cisgender women were more secure and not afraid to reach out to me. Especially interesting to me was the interaction I had with the lesbian community. Most of the lesbians I had a positive experience with had past encounters with men, so I was not so far from a person they would consider knowing. I learned quite early in my experiences in public, the various levels of the lesbian society. In fact, my first date with a man was with a very masculine lesbian on his way to becoming a full-fledged transgender man. Many times, the more masculine the lesbian, the more interest they showed in me. They were certainly not gender impostors.

Real life gender impostors are everywhere in this increasingly hostile world. We don't need insecure people in power using transgender women and trans men as crutches to increase their own power. 

Gender Lighthouse

 

Image from Juan Gomez
on UnSplash.

As I grew older and more in touch with my possible transgender womanhood, it often seemed to me to be a distant light at sea in my life. 

In fact, I equated my brief encounters with gender euphoria as moments in time when I was hopelessly adrift in a huge sea of life around me. I was rowing my little boat as fast as I could against a strong current, I mostly did not understand. Long ago, my gender notebook had been washed overboard, leaving me on my own to understand a new and exciting feminine world. 

As I was stuck rowing in circles in my shrinking male world, faintly in the distance, I could see a lighthouse which would ultimately show me the way to gender freedom. As I kept on against all odds, the light grew brighter. The entire ordeal was difficult, and I needed to battle tons of self-destructive behavior on my part to just survive at all.

Plus, through it all, my mental health suffered terribly. Since I was already diagnosed as being bi-polar, the last thing I needed was gender dysphoria to worsen my condition. Worse yet, I tried to self-medicate my problems with too much alcohol. Which ultimately caused me to lose my way more dramatically and take more self-destructive chances. I was taking my eyes off the lighthouse, and it was fading away in the distance. Just in time, I was able to regain my equilibrium and was able to set my eyes firmly on the light again.

I was able to get out of my boat and try the world at its best and worst. As I said, my feminine workbook long ago disappeared and I had to go it alone. As I mentioned in my last post, out of sheer good fortune, I was able to work my way out of potentially dangerous situations when I could have hit the rocks in my little fragile boat. I reacted to the experiences as surviving points on my gender learning curve. I resolved to learn from each one and keep my eyes on the light which was slowly becoming brighter. Maybe, I could achieve my dream of transgender womanhood after all. 

For a long time, the person who kept the key to my dream was my second wife who told me on occasion to me to be man enough to be a woman and being the pretty, pretty princess just was not going to be enough to make it. The problem was, she made me figure out what she meant, and it took me years to do it. I needed to wait until I had rowed to shore on the feminine side of the beach and found my way behind the gender curtain by learning lessons cisgender women grow up understanding from lifelong lessons. Or the pretty, pretty princess better learn how real women live in a world they control. I started to dress to blend in with other women on one hand and how I lost intelligence in my conversations with men on the other. Very quickly, I grew tired of being "mansplained" on the very simplest of topics. 

Once I found the lighthouse and made it to shore, the hard work started, and I needed to learn how to communicate with the world, one on one. Nothing told me, my communication efforts would be mainly with the women I met in the world as most men mainly left me alone. I knew most of the women started the conversation because they were curious what I was doing in their world. I did not really care because I was learning what I needed to know to keep my boat on the gender beach. 

Thanks to the world of women I encountered, I found the lighthouse at the end of my search and was able to find my way in a new world as a transgender woman.

From Obsession to Passion

 

Image from Kayshawn Herandez
on UnSplash. 

For years I considered my desire to cross dress was more an obsession than anything else.

Similar to many of you, I started my path to femininization innocently enough by rummaging through my mom's clothes. Whatever I could fit into was fair game for me. The pleasure of the overall experience soon turned into an obsession. When I returned home from school and was alone, I locked myself into the bathroom and got busy with mom's clothes and makeup. 

Even though I was wrapped up in my obsession at such a young age, doubts snuck through and slowly became evident. The biggest doubt was I was more than just a cross dresser. I wanted to be so much more. Such as the totality of being a girl. Looking back, it was sad I did not have more information on gender issues because I would have discovered and hopefully faced up to the fact, I was more transgender than cross dresser. 

As I trudged forward through life, I stubbornly held on to the best I could to my largely unwanted male ways as I idolized the girls around me. Thinking they had all the assets in life. Primarily the one in which they did not have to be forced to serve in the military during the Vietnam War as I did. Why did girls not have to serve, and I did, made me quite bitter. However, there was nothing I could do about it, so off to serving three years in the Army I went. 

As soon as I was honorably discharged from the military, I began to restart my cross-dressing obsession in earnest. Off came my Army mustache and on came the blond wig. Since my first wife knew I cross dressed and did not really care, I was able to do more exploration into the world of fashion, wigs and makeup. In essence, I was making up for all the lost time (three years) I had in the Army when I could not cross dress. The lone exception was a Halloween party when I dressed as a prostitute. The one night of bliss hardly made up for the three years of staying away from my obsession to at the least appear as a woman. 

When I finally had the courage to try out the world as my increasingly evident feminine self, my focus began to change from obsession to passion. I spent every spare moment daydreaming of how it would be to try out what I was doing as a man to a woman. During this time, gender reality shifts turned out to be a major point of my life. Especially when I actually began to live out my gender dreams.

What I did then was set up mini gender "bucket lists" to attempt to conquer. I say attempt because several were ill-advised and nearly impossible to accomplish. One in particular led me down a dangerous safety path when my male security privilege was lost. I almost learned the hard way not to be on dark city streets out of my car unescorted. Even though, I was still stubborn about my passion, I learned I needed to be careful. When I went back to the area where I was approached at night, I made sure I asked one of my transgender man friends to escort me. It was a new experience to ask for help. 

My passion to be a full-time transgender woman took me through gender affirming hormones and changes I never thought possible. I was grateful I was medically cleared to take the meds by a doctor at the advanced age of sixty.   

I am also grateful to be living my passion now with a wife who loves me very much. I took over a half a century to get there but I switched a basic obsession to a fulltime passion, and I never looked back. 

Why Not Me?

 

Image from Danielle
la Rosa Messina on
UnSplash

Going through life, I was very insecure concerning many things.

I always had a difficult time excelling at all in things such as sports because I was so insecure about winning. If I did not, which was common, I could run home and hide behind my makeup and pretty dresses and pretend I was a girl and all the pain of losing went away. Then, the more I cross dressed, the insecurities began to sneak in there also. Was I presenting well enough and how would I ever know if my only contact was between me and my mirror. I thought I looked presentable, but would the world agree and what if I looked like a clown in drag.

It took me years to even acquire the basic wardrobe and fashion I needed to even get myself a fair shake with my feminized presentation. All along, my lifetime dream was to be a woman, and I was so far away. I did try to make an excuse to cross dress and come out to a friend once, but it was a dismal failure when he was embarrassed and turned away. The whole experience sent me running back to my gender closet and slamming the door. I did not know what my next move would be.

Life went on for me and the desire to possibly living my feminine dream never went away. In fact, it became stronger and stronger. When I could, I made "investments" in better fashion, wigs and makeup which really helped me advance my overall presentation. As I did, I gave the public another try to see how I faired in the world out of my closet. I needed to put aside all my insecurities, gather up all my courage and give it a go. 

Initially, my path was a bumpy one, full of false stops and starts. I was flying blind with no handbook to help me, and it showed. During too many nights in failure, I had to run home in tears wondering if I was on the right path at all. Somehow, the faint voice of my inner feminine soul could be heard telling me not to give up as there were better times ahead. I listened, pulled up my big girl panties and managed to move forward as I discovered a better life as a novice transgender woman. 

I discovered the best way to combat my insecurities was with confidence. I resolved to never let the world see me sweat. First, it would ruin my makeup and second, if someone had a problem with me, it was their problem, not mine. I had put an incredible amount of time and effort into being the new transgender woman I was becoming, and I would be dammed if I was going to give it up easily to some bigoted transphobe. All the years of losing weight, learning makeup and skin care just could not go to waste as I chased my insecurities about living fulltime as a transgender woman. 

Still, I wondered, would I ever be good enough to join the world of women and would it be what I expected it to be. 

Unexpectedly, I received a giant push from women friends I found and cherished. With their help, I was able to put my insecurities behind me and become a part of a world I had only dreamed of. Why not me, became you can do it and I succeeded in my path into transgender womanhood. 

Torn Between Two Lovers

 

JJ Hart in Key Largo

For too many years I care to remember, I was torn between two lovers.

The lovers I am referring to, were my second wife and my inner feminine self. The battle was often intense as both of them decided to take no survivors or prisoners.  Plus, the problem intensified when I became immersed in the feminine world and my second wife grew increasingly resentful about it. Which meant when and if I went to her for any assistance, I was rejected. In fact, on the rare nights when she had to come to me for makeup advice, I could tell it really hurt her to do it. 

I distinctly remember one night she agreed to go out to dinner with me cross dressed as my increasingly important self. I knew at the time, if I was to have any hope of acceptance from her, I would have to make my attempt to dress like her. Which meant I needed to pick out my best jeans and blouse for the date. I even went as far to be careful to tone down my makeup. Predictably, all of my efforts were not enough. She made it clear she did not like or wanted to do anything with me. It was the last "date" I can remember. 

The gender conflict caused many rifts and giant fights between us. When the fights happened, somehow, we were able to patch up our relationship. Often with the promise I would never go out of the house into the world again. Which led to a huge problem. Deep down, I knew there was no way I could keep my promise. Because, at the time, I was so into the scary, exciting new world I was exploring, there was no way I could go back. The problem was, I felt so natural as a transgender woman. 

It turned out, the emergence of my novice transgender self-began to make my wife and male self very uneasy. After all, their very existence was being threatened. 

The whole process tried to destroy me. It was often too much to take when the battle for myself reached an all-time high intensity. Certainly, being torn between two strong women was no fun and I would not wish it on my worst enemy. 

I did not know for years how strong my inner woman was. The years she had spent being hidden away had taken their toll. She became strong on her own by default. Sadly, the battle ended without a true winner when my second wife unexpectedly passed away due to a massive heart attack. By default, my stronger feminine self, pushed my weaker male self aside and took over. 

I had lived through an unique transgender situation. I was torn between two lovers, my wife of twenty five years and my developing inner feminine self who was busy telling me she had been along for the ride for my entire life. I suffered through it all and came out on the winning end. As I said, being torn between two lovers was no fun. 

Trans Girl at the Roller Derby

 

Transgender Roller Derby Woman

Way back when, as I was building my transgender confidence, a group of lesbian friends invited me to tag along to their roller derby experience. 

Even though, I was slightly petrified to say yes, I enthusiastically went along with the idea. What could possibly go wrong with a small group of lesbians drinking one dollar beer watching women's roller derby in Cincinnati? Actually, nothing did go wrong, and I ended up having a great time. 

Also, I was amazed at the number of women in the crowd and on the rink who were more masculine than I still was.  All of them helped me to calm down and have a better time at the event. The only problem I almost encountered was when I used the women's room. It involved an evil stare from a woman coming out as I was going in. It also turned out to be one of those days when I was wearing more makeup than the majority of the women in the venue. Of course, I tried my best to apply the bare minimum of makeup so I could blend in, but it turned out to be impossible. There seemed to be no one wearing any makeup at all. I guess I identified as a "lipstick lesbian" for the afternoon. 

After I settled in, I found I could even enjoy the action on the rink, even though I did not understand all the scoring moves I saw. Plus, I had read the story of a transgender woman who had skated for a Long Island, New York, team who had fought and won her right to to participate. This was way before todays bigoted transgender backlash around the country. 

Sadly, I never went back to the Cincinnati Roller Girls matches again. My excuse is I was never invited back until my mobility issues made it difficult for me to do. Plus, my small group of lesbian friends drifted apart. In the meantime, I was able to check off another item I did not really know I had off my bucket list of things to try as a transgender woman. My friends were doing a wonderful job of pushing me out of my gender shell and if they wanted to do something as a group, I was included.

Everything I was able to check off enabled me to grow my all-important confidence in the world. From there I was able to begin going with my future wife Liz to "Meet Up" groups in the Cincinnati area. "Meet Up's" are groups of strangers who get together to discuss all sorts of topics from writing to knitting and beyond. Meeting strangers again did wonders for my confidence in the world as a transgender woman. I equate the whole process as building a new foundation in life away from anyone ever knowing my old male self. 

Finally. the wall became thick enough and high enough my old male self was completely shut out and he became the one stuck in a dark gender closet. My trip that afternoon just became one more success story on my journey to transgender womanhood.

Creating Gender Tension

Image from Tim Mossholder 
on UnSplash.

 
I am aware of the natural tension which goes on between the binary genders of male and female. 

I am also aware of the added tension which goes on when a transgender woman or trans man tries to cross the gender frontier to live on the other side. For me, at least, the tension became ridiculous and ruined my mental health which was already fragile. Before I was diagnosed with gender dysphoria, I was diagnosed with being bi-polar also. At the time, the diagnosis seemed to be a double-edged sword because I was wondering why I suffered from deep mood swings and blamed the swings on my gender issues. When I found I had deeper mental health issues, in many ways, it was a relief they were not tied in with my cross dressing. On the other hand, ideally, I could treat being bi-polar with medications and move on with my life.

My worry was any future therapy I might seek out, would involve the therapist attempting to tie my mental health in with my need to be a woman. Even though it was true, my gender needs did conflict with my mental health and cause tension, they were both separate entities and needed to be dealt with separately. I was fortunate in that I had two long term therapists who agreed with me, and I was treated as such.

However, my gender tension never went away, and, in many ways, I just learned to live with it. What I did was, resort to what I did when I was younger and try to cross dress my way through my transgender life. Predictably, when I was cross dressing, life was good and when I was not cross dressing, it was not. I was mean and tried to take it out on the world around me. I became so mean on occasion; I lost a job because of it. What no one understood was, I was being tougher on myself than anyone else. In typical male fashion, I was internalizing my feelings until they exploded. I even used therapy as a crutch with my second wife who had to put up with me. The best way for me to explain it is, I would never quite tell my wife what my therapist said. The prime example I can give you is, very early in my sessions with a certified gender therapist, she told me there was nothing to do concerning me wanting to be a woman. Sooner or later, I was to just have to follow my instincts.

There was no way, I could tell my wife that when I was supposed to be undergoing therapy to save our marriage. So, I ignored what the therapist told me and predictably, the gender tension continued and even became worse. I did my best to tread water and try to live a life divided between being a man part of the week and a trans woman when I could the remainder of the week. It nearly killed me as I tried my best to maintain an impossible life. My best was not good enough and I attempted an ill-fated suicide. When I woke up the next morning after taking all the pills I had and chasing them with alcohol, self-preservation kicked in and once again I made the wrong decision and resolved to purge most of my feminine fashion and make up, then go back to my male life. 

We all know the majority of gender purges don't work. Certainly, it did not work for me, even when I grew a beard to satisfy my second wife that I was not doing anything related to cross dressing at all. Once again, my gender tension rose to a very ugly level, and I was very unhappy. Little did I know, my life was due to change in a very tragic and dramatic way when in approximately six months, my wife passed away from a sudden heart attack. 

The life changing experience led me back to my feminine self and I never looked back. When I did, the gender tension I was suffering from disappeared and I felt free.  

Nobody Understood

 

Virginia Prince

What really hurt me when I first realized I had gender issues was when I had no one to share them with. I was all alone with my problems, or so I thought.

I lived in fear of discovery all the time from my parents or my slightly younger brother. Even then, I knew discovery meant an unpleasant trip to a psychiatrist. The closest friend to me who may have shared a few of the same feelings, ended up moving away. With him, both of us were allowed to experiment wearing his mom's old clothes and putting on her makeup. It was the closest I would ever come to having anyone to share my true life with. Ironically, we never talked about the cross dressing we were doing. We just did it. 

As I said, my friend and his family ended up moving far away and years later, I often wondered if he had any gender issues too which stayed with him. Plus, as I always point out, I spent my youth and the years leading up to college in the information "dark ages", or the time before the internet became so popular along with social media. All I had was my cherished copies of Virginia Prince's "Transvestia" publication to get me by. At the least, "Transvestia" showed me there was a community of others with the same gender leanings I had. Also, in my well-worn issues I saw meetings or mixers within driving distance of me which I could go to. I was excited when I learned I could actually meet other self-proclaimed transvestites in person. The problem was, once I learned I could meet them, was I brave enough to do it. 

You all know, I was brave enough to meet them but then I encountered another problem. No one at the mixers still seemed to understand me. I was too much of a woman for the cross dressers and not enough of one for the transexuals. This was back before the transgender term and meaning was even used and popularized, so once again, I was stuck with no one to understand me.

Finally, the world began to catch up with me and I understood where I was when it came to the cross dresser - transgender community. Even better, with the help of the internet and social media, I began to stay in touch with others with similar views. Suddenly, in many ways, everybody had some sort of an understanding about how I felt. It may have taken me a lifetime to do it, but I made it into the only community who knew what I went through.  

Maybe the problem with the world as we know it these days has been influenced by people who have never met a transgender woman or trans man at all. To understand a trans person, it certainly helps to have followed a similar path. Even briefly. 

In recent years, I went from no one to understand me to having a whole group of people who have not taken the time to even accept me on a basic human level. It seems, I have gone full circle to arrive nowhere. 

Once Your Eyes are Opened

 

JJ Hart, Club Diversity, Columbus, Ohio

In my case, once my eyes were opened as a transgender woman, I could never close them again.

Perhaps it is because I went through so many trials and tribulations to arrive where I wanted, or even desperately needed to be in my life. Since I had so few natural feminine traits to work with, I really needed to work hard to achieve a feminine presentation. I tried all sorts of ill-fated ideas before I ever got it right. Yes, it was me making the routine cross-dressing mistakes such as attempting to dress as a teen aged girl when I was thirty and had a testosterone poisoned body. All I accomplished was directing unwanted attention to myself. 

 It took me awhile to realize what I was doing, and my eyes were finally opened to what I was doing. The perception I had was I was dressing for men, when in fact, I should be doing the opposite and dressing for the women around me I needed to co-exist with. I learned the hard way, women ran the world I wanted to be part of, and I needed to do my best to get there. All of this meant I needed to keep my eyes open and do the best I could to study the women around me. Or how did the women react to the world around them, good or bad. 

Sadly, blocking my way were women such as my second wife who wanted no part of living with another woman, transgender or not. She was content with letting me learn on my own what women needed to survive in the world. Looking back on it, her process for me was the best way to go because once I learned something in my new transgender womanhood, I never forgot it. Also, magically, once I opened one door to my new life, my eyes were opened to another door. 

As I opened a new door, I knew I could never go back to my old male life which was bringing me down. I felt so good and natural in my new life, there was really no choice to be made. The only problem was what was I going to do with all the male baggage I had acquired over the years. Similar to most of you, I had the usual assortment of spouses, family, friends and employment to deal with. Fortunately, I started my transition process with the person who turned out to be the most accepting of all my family and friends. I am speaking of my daughter and her immediate encouragement helped pave my way to more attempts at telling the world about my authentic self. I ended up going one for two in the family process when I was roundly rejected by my brother and his family. He opened my eyes to what transgender rejection could really be like.

Still, I persisted, knowing I was on the right path and my eyes were not deceiving me. It took me awhile, but I finally gained the confidence to look another woman in the eye and communicate one on one with her. To do so, I needed to not concentrate on how I sounded and instead put an emphasis on what I said. In order to survive, I needed to keep my eyes open at all times because certainly every other woman was not going to be my friend. 

I did keep my eyes open and learned the hard way to keep my head on a swivel. There were many claws I needed to be aware of. Quickly, I was hardened to what the new world was like around me. More and more, I could never go back to the male privileges I had before. Even though, I lost much of my intelligence according to most men and especially lost my personal security, I still wanted more and more of my transgender womanhood. 

You might say, I acquired new 20-20 vision and it was perfect in many ways. It was a long and difficult learning process, but it was the best life I could have ever imagined, and I just felt I had done it sooner. 

The Comfort Zone

 

My trans friend Racquel

As a transgender woman or a trans man, you often encounter major barriers when it comes to reaching our gender comfort zones.

We have all sorts of setbacks such as family and spouses, employment and potential loss of friends. Giving up the life we had been leading is never an easy decision to make. It's definitely more than just an easy choice which a percentage of people (or transphobes) think it is. For some reason, they think it is just a matter of transgender people putting away their clothes and returning to their birth genders. They don't understand how deep our experiences run. Along the way, we become very resilient in our journeys and for the most part, our tribe is strong.

We are strong, in part, because of the time and experiences we went through to reach our comfort zones. I know I had to endure stares all the way to out and out laughter in the early days when I went out and challenged the world. Catching up with all the years I lost not growing up as a girl really came back to haunt me when I had to struggle to catch up. No one taught me the basics of fashion and makeup. More importantly, I did not have the confidence I needed to move forward to even learn if my gender dreams could ever become a reality. Which was the most important thing to me.

Slowly but surely, with success, my time in the comfort zone came around and I survived. It was never easy. To this day, when we traveled to the Florida Keys recently, after all I had been through in my life chasing my gender, I still was very nervous about several things I would face along the way on the bus tour.  I did not know how I would fare as a transgender woman on a bus full of strangers. Especially when it came to having restroom privileges as we traveled through the deep south. However, I can't spotlight the deep south for its anti-transgender laws when my native Ohio recently has passed some of the most restrictive trans laws in the country. I guess you could say, I could run but I could not hide.

Quickly, my fears dissolved as the other women on the bus began to not so slyly question my wife Liz and I's relationship. The reason was one woman said to Liz, she thought we were sisters. Which really increased my confidence and put me in a comfort zone which would last for the rest of the trip.

My comfort zone expanded, and I was able to enjoy my new reality of acceptance in my transgender womanhood. Of course, it was all challenged when I caught Covid on the way back to Ohio and ended up in a suburban Atlanta hospital. I was fortunate in that I had my Covid vaccine three months before and my case was lessened in its severity. My three days stay in the hospital really challenged my comfort zone because I have never had any gender altering surgeries. So, even though the staff initially thought I was a woman, it quickly became evident I was still a biological male. Hopefully, I won't have to go through an experience such as that for a while again.

As we all know, comfort zones are fleeting and have to be earned. You need to be patient and do the best you can until your confidence as a transgender woman or trans man comes along, and you are finally comfortable in your own skin. 

Tomorow is Here and It Is Ugly

 

Image from 
Charlesdeluvio on UnSplash

Back before the election and I was voicing my concerns about a tRumpt presidency, I received a comment from a self-professed transgender woman who said she was a conservative and supported the felon. 

Her reasoning was, he had not been that bad during his first term. She also mentioned nothing about all the negatives he spewed about the transgender population. Well, he is here now and in all his glory has shown an indication to destroy the foundation our country was built on. It turns out, the self-professed "king's" attacks on the transgender community were just the beginning. In fact, the attacks on DEI have reached down as far as my association with the local, Cincinnati, Alzheimer's chapter. 

For those of you who did not know, I have been a member of the local Diversity Commitee for the past several months or nearly a year. Very recently, the message came along from the council saying the Diversity Council would be changing its name. They were removing "Diversity" from the title. Naturally, I was shocked to say the least. The long tentacles of hate from the new felon's administration had suddenly become a stark reality to me. 

Since that time, I have decided to resign my spot on the committee in protest. The remainder of the group can pursue their new "health initiative" without me. 

With everything else happening in our country right now, I wonder what all the transgender women or trans men think now. 

As far as I go, I live in fear of my future. Not as far as being attacked is concerned but what potentially is going to happen with my Veteran's Administration health care benefits. I have a potentially key appointment coming up soon because my Estradiol prescription has run out. So, I will see if a problem getting my gender affirming hormones is going to be a problem or not. 

Looking further ahead, I fear after the Musk/tRumpt social security purges, what will happen with my future payments I use to live on. 

Bottom line is, I resent all the challenges I have to deal with at the age of 75. Just because a bunch of billionaires can increase their wealth. To hell with being a conservative or liberal, I just want to live and can't help being deeply resentful to all who support the king felon. Tomorrow arrived for me, and it is ugly.

Someone is Paying Attention

Image from Alena Garrett
on UnSplash. 

One thing I immediately noticed when I left my mirror and went into the world as a novice transgender woman was when I was suddenly noticed more by both primary genders, male and female.

Of course, being raised in an unwanted male world, I knew how many guys made a big deal about the appearances of the women around them. What I was not prepared for was the amount of attention I received from other women. Especially, younger ones as teen girls were especially observant. I cannot or prefer not to recount the times I was stared down by a group of teenaged girls or younger. 

My primary example was the day I was out shopping in the racks of a women's clothing store when around the corner came a small child who startled me. Obviously, I startled him also because he ran back to his mother (who was close by) and said, "Look at the BIG woman!" Initially, I was relieved because he had called me a woman. Then he continued and said, "The big MEAN woman." Naturally, I learned a big lesson. The BIG mean woman should always be prepared to be friendly, which means I needed to immediately learn to wipe that old male scowl off of my face. If that was all I needed to do to not scare little kids, it was an easy lesson to learn. 

For a while, I was intimidated by all the attention I was receiving until I began to understand where it was coming from. The more I dressed to blend in with other women, the less attention I received from men. Primarily, because I just wasn't that attractive. On the other hand, the increased attention from women came from the fact most of them were just curious what I was doing in their world or were appreciative of my efforts to look the best I could. If I had a dollar for every time I was complimented on my jewelry or earrings, I would be a rich person now. 

It took me time but eventually I learned my lessons well and adjusted to the fact, my appearance as a transgender woman was a fact of life and in many ways a form of female privilege I needed to live up to. My observations made me work even harder on my feminine presentation. In other words, it was all part of my rite of passage into transgender womanhood. Plus, in many ways, I needed to work even harder to present well than the average cis-gender woman who was just getting by because she happened to be born female. Which, by the way, did not automatically allow her to be a woman. Neither gender birthrights allow them the permission to claim an automatic right to claim a title of man or woman. Which comes from socialization. 

I learned if someone was paying attention, I should make the most of it and adjust to my new surroundings. Once my confidence built to a point I could do it, I was able to project a strong feminine aura. When I did, questioning my gender became someone else's problem. Not mine.

Down the Rabbit Hole

 

Summer Image, JJ Hart.

Over the years, I began to sink rapidly or was stuck in an increasingly large and deep transgender rabbit hole.

Sadly, I did not have the information I needed at a young age to help me to understand I was much more than a boy who preferred to dress in girls' clothing. I just knew I was not satisfied with cross dressing in front of the mirror on the rare moments I was alone. I always had problems with what I called the gender roller coaster, or I was up when I cross dressed for a couple days before I crashed to the depths of depression and daydreamed my life away thinking of the next visit, I would have in front of the hallway mirror. 

Only one of my thoughts was for certain, I was falling down a gender rabbit hole which I could never return from. For many years, I thought I would possibly grow out of my gender issues, and they could possibly be a phase. Of course, wanting to be feminine in all aspects of my life, was never just a phase and just grew stronger as I aged. 

It turned out, the older I became, the fonder I became of my rabbit hole and wanted to stay there. When I did go out, I was like a real rabbit, cautiously surveying the world for predators. It was not until I began to arrive at a financial point when I started to build confidence in my cross-dressed presentation, did I begin to enjoy my trips out of the hole and into the world. 

It was about this time too, when I began to expand my rabbit hole. I needed more space for my wardrobe and wigs of course. Not to mention the mental room I needed to grow into the person I was becoming. Once I saw the light of my new gender day, there could be no turning back. The light felt so good and so warm; I was loving my new life. 

I ended up forsaking my gender rabbit hole for a new universe of women. To be truthful, it was the most difficult experience of my life. Since I had left my old comfort zone of white male privilege, establishing a new base was difficult in my new transgender womanhood. I had dug my gender rabbit hole so deep; it was difficult to find my way out. 

Sadly, I see too many transgender women and trans men who are stuck in their gender holes. Especially, in the current negative situations we are living in right now, I understand why so many LGBTQ people want to stay out of the public eye. It is just a shame we need to do it.

Meeting in Person

JJ Hart in a warmer time.

Do you remember the moment you met your authentic self in person?

Looking back, I can recall several profound moments when I saw the feminine person I was always meant to be. My earliest memories came when I was quite young in the days when I was first experimenting with my mom's makeup and clothing. Even though I probably looked like a clown, the mirror told me I was beautiful. No matter what I looked like, I refused to face the truth. 

It was not until much later in life, when I began to realize how much work it was going to take to really see my true self, did I get serious. If I was going to make it to my dream of transgender womanhood, I would have to profoundly change my way of thinking. The first change I made was how my male ego interacted with my appearance the public saw when I went out for the first times. 

The truth of the matter was, if I dressed "down" to blend in with public, I received very little attention, so I started to dress too trashy to please my old male self. What quickly happened was I attracted the wrong type of attention and did not pass well. Or, at all. Back to the cross-dressing drawing board I went time after time until I drove my male ego out to the point where I was successful in blending in with other women in the world. What were the women wearing and when were they wearing it became my motto. The time I spent was worth it when success as a novice transgender woman was becoming mine. 

Suddenly, my visits to the mirror became more and more friendly. I adjusted to the fact I would never be the prettiest woman in the room, but I could rely on other feminine attributes to get by. I began to closely study other women who may not be the most attractive, yet still be popular, fulfilled women. What I did was, I began to concentrate on what my new personality would be as a transgender woman. After all, I had an unique opportunity to start all over again as a human being. My new time was a scarce commodity, and I could not miss my opportunity to do it right. 

I was fortunate in that I already had a women friend who was ready to help me. She had been there all along, just waiting for her turn to lead my life. She was the feminine inner me. It turns out she was a nice person who saw the best in others. When I met her in person, I was excited and knew I was in good hands.

I was in good hands and began to expand my small circle of friends in the world. My wife Liz and I started to go to small and medium sized "Meet Up" groups in Cincinnati where I learned the benefit of a different group of strangers accepting me. None of us knew each other previously, so I was on an even level with them. The great equalizer. 

All of the process was extremely beneficial when it came to meeting myself in person until I became used to it. Perhaps the best part of the entire process was the time I realized I had really expanded myself as a woman, transgender or not.

Not Scared? In the Wrong Room

 

Image from Alexandra Gorn
on UnSplash.

I cannot begin to tell you how terrified I was to interact with the public when I first began to attempt to live in the public's eye.

One night in particular always stands out in my mind. It was the evening when I had pre-determined my cross-dressing days were behind me and I was going out as a transgender woman. Furthermore, I knew if I was successful, it would change my life forever. As I prepared for my big night out, I took extra care with my outfit, makeup and hair. I wanted to make sure I blended properly with all the other women I would be interacting with at an upscale bar I was going to which was heavily frequented by professional women who worked at a nearby mall.

Once I made the short trip to the venue and found a parking spot relatively close to the front door. As I sat in the parking lot, the pressure to go in increased dramatically. As I nervously checked and adjusted my makeup in the car's rearview mirror, again and again the fact was not lost on me I could be changing my life forever. By the time I gathered my courage to actually enter the venue, I could barely breathe and was gasping for air. 

It took me awhile to gather my courage and enter the front doors of the place and interact with the hostess stand. Deep down, I was hoping the hostess would be busy seating other patrons so I could sneak on through and find a seat at the bar. The short distance from the hostess stand to the bar seemed to be miles to me but I made it and luckily found a corner seat at the bar by myself. Plus, the bar itself was supported by two large thick pillars. I figured if I found a seat next to one, I could blend in and hide if I needed to. I did not need to hide as I was approached for my order by a friendly bartender. 

Immediately, my fears began to melt as I ordered my first drink and even started to relax a bit and watch all the other women who had begun to arrive at the bar to enjoy each other's company. As I observed the group, I saw no one was noticing me. So far, so good. No one noticed a very scared novice transgender woman in their group. 

Of course, this evening was only the beginning of my new transgender journey. I knew my life had changed forever. I could never go back to the old unwanted, boring male life I was living. To move forward, there would be many nights when I would be very scared. Somehow, I learned to feed off my fear to propel me forward. No longer was I a weekend cross dresser, I was reborn as a very serious transgender woman.

My end game was using fear to refine my push forward by putting extra time and effort into my fashion and makeup. That way, when I needed to walk past a crowd of strangers in a new venue I was in, I could do it without any issues. 

I finally decided, if I did not feel any fear at all, I was in the wrong room. Especially, in today's climate, it pays to always be aware of your surroundings. Maybe fear is a strong word, but awareness is not. 

The Gender Envelope

 

Image from Alexandru
Zdobau on Unsplash.

Sure, I spent or waisted far too many years before I fully transitioned into transgender womanhood.

I was too slow for such a long time actually pushing my personal gender envelope when I was busy telling myself I was no more than part-time cross dresser. I saw no harm in just doing my best to look like a woman until it just wasn't the answer I was looking for. The more I cross dressed and improved my feminine presentation, the more I pushed the envelope and looked for more. Very quickly, my yearly Halloween adventures just were not enough.

I began to wonder if I made a good impression at Halloween, could I make the same impression if and when I tried to go out in public as a novice transgender woman. Following many trials and error experiences, I found I could survive a public which largely did not care about me. The big error I always point out is when I was not receiving any attention to speak of as a woman, I began to dress trashy to attract the wrong sort of attention. I was mistakenly pushing my gender envelope the wrong way. When I finally began to understand the best ways to dress my male body and apply the proper makeup, did I begin to be successful and blend in with other women in the world. 

Once I had accomplished all of the fashion, hair and makeup necessities, I allowed myself to further push my gender envelope. When I did, I found myself needing to understand how women exist in the world. Or how do they communicate with other women and men. I had a quite a bit of catching up to do since I was attempting to catch a moving train heading down the tracks. I did not have the benefit of growing up female with a mother or peer group to guide me. I always point out; the passive aggressive system of interaction most women operate under was the most difficult for me to learn. Since childhood, I was always used to the full-frontal confrontational world men operate in so I was attempting to survive in a whole new world.

Once I did survive, I began to push even harder, ignoring warnings from my wife on what would happen if I was ever caught. I put the male gay bars behind me and moved on to big sports bars and lesbian bars where I could actually be myself. I thought I had reached my peak when a dear friend of mine invited me to a trip to a NFL Monday Night Football game in Cincinnati. Even though I was very scared at the thought of going, I could not turn down a chance to empty my envelope and lay my gender cards on the table. Since I am not really a gambler, I hoped the lifetime of preparation I put into this moment would serve me well. 

The moment did serve me well. As always, I survived and became a better woman for it. Plus, I learned the game was only the beginning. The life in my transgender womanhood I was going to experience, would be extremely fulfilling and everything I thought it could be when I started pushing my gender envelope.