When too Much Wasn't

 

JJ Hart (Middle) with two friends.

As I continued along my long and winding gender path, I (on occasion) ran into situations when the public seemed to be too much. 

Examples were the times I was approached in public by strangers when I did not want to be. Very quickly I needed to judge their motives. Did they see me as a man in a dress on one hand, or as a woman on the other. Naturally, it made a big difference when I returned home and rated my experiences as a novice transgender woman out in the world for the first time. How did I do? Was I too much for my own good and did I need to tone it down, or attempt to do more?

There were the times when I managed to thrive in situations where women dominated and times I could not and ran home. Back to my gender drawing board. There seemed to be so much to learn, I was overwhelmed by the task ahead of me if I was ever to achieve my dream of living a femininized life as a transgender woman. 

In the end result, normally I found too much just was not when I was trying to get ahead in a new world I was just getting used to. The problems occurred mainly in the areas of fashion and makeup, as well as where I was trying to go when I went out. Once I got them under control, I was able to build a stable new life in the girls' sandbox. Once I earned my way in. Often earning my way in, had its own set of challenges. Mainly I had to find out how to play correctly to be accepted. On the other hand, even though it was difficult to do, I had to play to learn a life's full of lessons in a hurry. As I always say, my women's workbook was blank to this point, and I needed to write it. 

I found as I struggled to fill out my workbook, I needed to be extra vigilant in how I viewed other women, since I was totally on their turf. For the most part, I did my best to hold back on my opinions and speak mainly when I was spoken too. It worked well enough until I could get my feet on the ground, and I could move forward as a transgender woman. My goal was to build my new life as a confident, intelligent woman in society, but I needed to prove to myself my goal was not too much and would destroy my dream of transgender womanhood. Fortunately, throughout my life, I had several strong positive feminine role models to work from and add to my workbook. When I was able to add their influences to the inner female, I already knew was there, the women formed a strong bond to guide me through my struggles.

Overall, I discovered rarely too much just was not. What was happening was, I was just paralyzed by fear to move on with my new life. Once I got over most of my fears, I was able to move on and be free to live a better life. A better mental health life waited for me when I quit fighting two genders to survive. 

Authenticity

Transgender flag flying at 
Cincinnati's City Hall.

 In order to just get by in the world, transgender women, or trans men need to be authentic. Which is always easier said than done. 

First of all, you need the confidence to try out your new self in an exciting yet scary different world. Maybe, a person smarter than me has an idea on how to provide yourself with confidence other just by just doing it. For transgender women, among other things, it means putting aside all the hard-earned male privileges we came to be used to. In order to be truly authentic in our transgender womanhood, everything male had to go. 

It took me years, or even decades to get around to living authentically as a trans woman. Before I was able to, I needed to adjust my thinking to what a woman really was, and what she had to go through during her life. As my second wife kept trying to tell me, there was so much more to womanhood than just looking like one. Finally, I started to realize what she meant, but it was not until I made it out into the world as a novice transgender woman, did I realize what she really meant. For me, it meant the girls nights out I was invited to, along with everyday communication helped me to discover my true feminine self. 

Even still, all those nights I went out to be by myself were not helping me with my authenticity. I learned the difficult way all females were not women because they were never socialized into womanhood. Through it all, I wondered where the whole process would land me. For years, I feared a hard fall in my life if I had fully transitioned into transgender womanhood, but it never happened for me. I think, the more I learned in my new life helped strangers to interact with me easier, one on one. 

Perhaps the biggest discovery in my life came when I learned firsthand how powerful my internal feminine self was. Once she sensed she had control in my life, she effortlessly took over and guided me to a soft landing when I slid off my gender cliff. One of the main things she did was making me how total the femininization process was once it got started. I guess the first thing she changed was how I looked at my life. For example, she made me realize I was never a man cross dressing as a woman, I was a woman cross dressing as a man. All of a sudden, my early life made sense as to why I could never satisfy the deep craving I had to dress as a woman, only to discover a couple days later, I would be depressed if I could not dress again and find the nearest mirror. I needed constant reassurance I was on the proper path to my own form of transgender womanhood.

I guess, authenticity can only be earned the hard way through lots of work and even experimentation.  When you do experiment, and are successful, gender euphoria and confidence set in and you are ready to move forward in your life.   

Transgender Day of Visibility

 

Transgender Day of Visibility
poster from my
hometown. 

Today is the annual transgender day of visibility on March 31st. 

It is a time such as never before to attempt to stand up and be counted as a transgender woman or transgender man. Sadly, it is also the time we trans people take the most risks to do so. Stakes are becoming higher and higher against us coming out in many areas of the country, especially, here in my native Ohio. Where an overwhelmingly republican legislature in the state capital of Columbus has passed bill after negative bill against us. 

To me, my visibility is an ongoing deal. Since I live fulltime in my transgender womanhood, long ago I decided to never run and hide my feminine nature. Back when I did not have so many mobility issues, I was more of an active participant than I am today. In place of being active at all, I have tried to pick up my pace with my writing and protest with my keyboard and votes. 

Plus, I know I am so fortunate to have found and married an accepting/encouraging spouse who helped usher me into my transgender womanhood. I know so many others in the community who are so lonely. 

Wherever you happen to be in your gender transition, these troubled days present a troubled challenge to being visible. Challenges such as your presentation provide sometimes insurmountable hurdles to being more visible. Similar to a "Catch 22" of passing. In other words, you need to be seen in public to learn if you present well enough to stay out of personal danger, but it is scary to even start to get the experience to begin with.  Again, I was lucky when my time to come out meant at the worst you were laughed at and not beat up. Plus, I was able to put years of practice into makeup, fashion, and wigs when I cross dressed in my closet. If the times were reversed, I often wonder what I would have done differently, if anything. All in all, it is just another one of those life's questions I will never know.

On this transgender day of visibility, I hope all of you find your own way to be visible. Anything from marching in a parade, all the way to looking at yourself in the mirror, find a way to celebrate the rare, beautiful self which is you! 

Nothing but a Reflection

 

Woman in Mirror from Darius Bashar
on UnSplash.

It seems for some reason, recently, I have been obsessed with thinking about my earliest days of admiring my girl, cross dressed reflection at home in the mirror. I hope in this post I will be able to take my obsession a step further. 

I believe women have a head start over transgender women when it comes to the basic concept of being viewed in the public's eye. To begin with, women are faced with more appearance scrutiny than men. Women have to put up with the reality they are viewed more closely by both genders. Whereas men don't have to face nearly as much scrutiny. Then, being a transgender woman takes even more work to survive in the world. 

Then there is the reality of reflection between genders. Women traditionally resort to makeup, beauty spas and fashion to reflect the best version of themselves to attract men and to a lesser extent, impress other women. It is at least a multibillion dollar a year business. Now, back to me, and where I was on my path to transgender womanhood. 

Where I was on my path, was I was still struggling with even having the beginners' basics on how I could reflect woman to the public at large. With the help of continued work on my makeup and me attacking the nearby thrift stores, I finally began to reflect feminine to the world. When I did, I could begin to refine my approach and relax in the world as a transgender woman or more advanced cross dresser. Mostly, that meant putting my mirror's reflection in motion. It was very difficult in the beginning, as I needed to look the women and men in the world in the eye and be myself. Humans have the tendency to explore the world through their eyes and I quickly became used to having other women look at me totally head to toe. 

All too soon, I was ripped from my mirror and living a very scary but exciting life in a new world. Very quickly, I was able to put my fears behind me and understand who was really looking at me. Men paid me very little attention because I always assumed I was not attractive enough, but on the other hand, I was really receiving much more attention from cisgender women than I had ever had before. Obviously, for whatever reasons, my reflection with other women was working well and I loved it.

I was on a remarkable gender journey as I left the mirror behind and joined the world. As I refined my feminine outlook, I needed to accomplish a couple major goals. The first was, to never not refer to myself internally as a man again. I was a she and that was it. The second was, I needed to concentrate on establishing my own feminine aura. I started to really begin to zero in on whom ever I was talking to into knowing they were interacting with a woman. If it worked or not, remains to be seen, but I kept on trying.

Projecting my aura was the last stop in my progression out of the mirror and into the world. I viewed it as taking the last vestiges of any light I had ever seen in the mirror and turn it into a bright light of hope. It was scary because I was not used to being in a such a new world as a transgender woman. Along the way, I took on my share of setbacks but kept on moving forward.

Now, the reflection I see in the mirror, is only the one I need to apply my makeup and closely shave before I go out. I have also worked hard to do away with any remaining gender dysphoria I may still have. When it does hit me, it normally happens in the morning when I first look at myself in the mirror. I finally have come to the conclusion I don't look as bad as I think or as good, I think I do with my makeup.  The middle point has become good enough for me, and the mirror has again become nothing but a reflection.

The Light in the Mirror

 

Image from Alessandro 
Bianchi 
on UnSplash.

I spend quite a bit of time here attacking my mirror when I was growing up.

Recently, I have come to the conclusion some of my negativity could have been wrong. First of all, I was fortunate to have a beautiful full length mirror dad installed at one of the ends of the hallway in our house when I was growing up. When no one else was home, I would spend as much time as I had admiring myself in the hallway mirror. As I did, I could always see a brief dim light in the mirror when I viewed my feminine self for the first time. Even when I knew, the light would have to be extinguished soon, and I would have to go back to my unwanted male world. 

As I grew up and began to explore the world for the first time as a beginning cross dresser, I made plenty of mistakes the mirror did not tell me about. In fact, the mirror light shone brightly and told me I looked great when in fact, I looked just the opposite. I was presenting as a clown in drag with no one to warn me. For a long time, the light in the mirror nearly went completely out as I was rejected in public time and time again resulting in a deep depression for me.

I kept trying though, and the light began to come back on. I lost weight and began to find styles of women's fashion which flattered my body shape and finally began to present better. Especially when I was making the mental transition to novice transgender womanhood from cross dresser. To do it, I needed every break I could muster. Plus, I needed to turn up my light in the mirror, and let my femininized light shine through, so I could see her better. 

The extra light turned out to be all I needed to become more skilled at my makeup art and do the best I could with my testosterone damaged male face. With a little help from a professional makeup person, my light in the mirror grew even brighter, and more importantly, I could trust it. With trust came confidence which equated to more acceptance as a transgender woman in the public's eye. All of a sudden, my lifelong dream to lead a feminine life was within reach. If my light in the mirror stayed on. 

It did and I was even able to turn up my light to a brighter level with the addition of HRT or gender affirming hormones. Among the many other positive changes I went through was when the overall texture of my skin softened. Which meant the male lines in my face softened and I could use less makeup. Specifically, foundation. I quickly learned with more femininized skin and being able to wear my own hair, I was suddenly more presentable to the world. 

Looking back, I may have been too quick to judge my light in the mirror. It just took a little longer (along with the rest of me) to become more situated with living a new life away from my old male self, and perhaps it was my fault for not switching to a brighter bulb sooner. Plus, I was fortunate in that my light in the mirror did not burn out altogether. 

 

Knowing the Rules before You Break Them

 

Image from Milan de Clercq 
on UnSplash

I had a very good idea of what it would take me to survive in a male world before I decided to see if the grass on the other side of the gender border would be any better or greener.

Growing up in a very male dominated family with the only girl being my mom, provided me with a so-called brightly lit path to my future. I was fortunate in some ways to have a larger male body to keep the bullies away as I played sports such as football and baseball regularly.  Of course, I came to dislike my body completely when I went through male puberty and had a difficult time finding any new fashionable girls' clothes to wear. 

When I went through the hated male puberty, the rules of the road so to speak, became clearer and clearer to me. Coming from a white middle-class family with two working parents in the 1950's to mid 1960's gave me a work ethic I used to scrape together the meager funds I needed to buy my own makeup and a few fashion accessories. I knew I could not ask my parents for the money because they would want to know what I needed it for. Any hint of femininity on my part would immediately break all the rules and would result in trips to a psychiatrist. Even then, I knew going to a therapist who knew nothing about gender issues would be a disaster. 

I knew the rules and played the game of male gender the best I could. I found good hiding places for my femininizing fashion and makeup while at the same time, dreamed of the day I could buy a nice wig. In those days, I was able to get by with a mirror who never lied to me by telling me I was a pretty girl. The feelings of joy or gender euphoria would continue several days before the pressure built up on me to cross dress again and again. When I began to realize I was just scratching the surface of my gender issues, I became quite good at knowing one of the primary male rules taught to me as a kid. If you did not like something, internalize it until it went away.

The problem I had was, my desire to be a woman never went away and it was so much more than just being a phase. From the darkness of my closet, I had what turned out to be a distorted idea of what womanhood meant to females everywhere. I only saw what I considered the good part was. Such as no military service and being able to enjoy the wonderful world of woman's fashion. I left out the challengingly part of women's lives such as child raising and toxic men, to name a few. As I was able to cross the gender border, I did realize the grass was not always greener and had I truly been a birth daughter to my mom, extra pressure to conform to her standards would have increased. I am certain she would have pushed me to go to the same university she did, all the way to pledging the same sorority.  I would have again been breaking rules. Just of a different sort.

When I arrived at a time when I was drafted into the military, I was forced into being a follower of rules more than I ever had in the past. Conforming to new Army standards to survive at least kept most of my mind off of my gender issues. I needed to put my desires aside and just dream of the day I could be free to be a transgender woman in my future. It was difficult, but I did it.

By the time I was honorably discharged three years later from the Army, I was able to settle back into the life I had before without one big exception. Without military service looming over my head, I could concentrate on my future. When I did, it became increasingly evident to me, there was a possibility I could break all the gender rules and achieve transgender womanhood. It was still going to be a decades long journey from there, but I was encouraged for once.

Of course, once I began to explore the world as a novice transgender woman, I found a whole new set of rules to deal with. To make matters worse, I had no knowledge of many of the rules I was about to break before I did them. The workbook I was using was blank and I needed to write the rules as I needed them. 

Again, I was fortunate, and I survived when I broke the rules, but I learned quickly since I was free.  Then as I safely continued along my gender path, I found I could make it safely to my dream. Mainly because I knew the rules from both sides of the binary gender and I was a better person for it. 

A Failure

 

JJ Hart at a Witches Ball.

There were many times in my life when I felt as if I was a failure.

I can blame a portion of my feelings on my parents who I feel placed unrealistic expectations on me in my male life. Of course, my up-and-coming female life was hidden from them, so I felt they had no control over me. Only the mirror seemed to. When I was able to transform myself into what I thought was a passable girl, no one could take the fact away from me I was a success in something. In fact, in those days, it was easy not to be a failure because I was so alone with my cross-dressing urges.

Even so, I still had problems thinking somehow, I was a failure. The major problem was I could never seem to get enough of viewing myself as a girl in the mirror. I began to think even though I had a temporary fix on my life, there was a deeper problem. Looking back now, I sense the problem was much deeper than just wanting to wear makeup and feminine wardrobe, I was going through the earliest stages of discovering I was transgender. The only problem was the transgender term and knowledge of had not been invented yet. Leading me to believe once again I was a failure.

As the years crept by and the overall knowledge of gender issues increased, I began to realize I was less of a failure. However, at that point, I began to explore the world more and more as a novice transgender woman so again I was beginning to feel as a failure when life did not work out for me. I was struggling to maintain my demanding male life, my married life, and my new life as a transgender woman. In time, the strain became too much, and it wrecked my fragile mental health. Most of the time, I did not know which way I was going, especially in my gender life. I needed to be careful when I was at work in a macho atmosphere not to slip up and show my feminine side and vice versa when I was experimenting with my feminized self. I certainly did not want to show any of my well-worn masculine tendencies.

Another problem was I had the idea I knew everything I needed to know about being a woman. Afterall, I found myself in a place where I looked the part. When I found out I did not, the difficult portion of my gender journey began. Putting the femininized version of myself I had created into motion was very difficult. Specifically, when I needed to actually communicate for the first time with the world. I felt as if I was a failure all over again and needed to start all over on my extended path to transgender womanhood. It turned out I did not really have to but still needed to work hard to look the public in the eye and have confidence in myself and improve my overall communication with the world. Eventually, I needed to enroll in feminine vocal lessons to improve myself. 

By improving myself, I was able to re-enter the world as an improved transgender woman and survive. I needed to roll up my sleeves and got to work to be a non-failure in a very demanding world.

Comments

 

Image from Bruno Acquire on UnSplash. 

In regard to yesterday's post concerning the Veterans Administration's announcement they were not going to cover gender affirming hormones, prothesis's, and even mental health treatment for new veterans suffering from gender dysphoria anymore. 

In my rant, I said, among other things, how much I disagreed with the move, even though it did not affect me. The VA said, those already receiving gender related care could keep getting it. Which, of course, means me. 

One huge problem I did not mention in my post was pointed out by Denise, who pointed out, the VA's decision to shut out trans women being discharged into the world to fend for themselves was just a smaller part of what the orange felon's presidential administration is trying to do to erase the rights of all women in our country today. Since transgender women are a unique form of women, our rights as women are being taken away too. Which gives me yet another chance to wonder why any clear-thinking woman, trans or not, would have ever voted for the felon at all. And I will leave it at that.

On another subject concerning a post called "Why Me?' a reader wrote in with this comment:

"Over many decades I often asked myself both “why me” and “why not me”. For decades I limited myself to underdressing…. something I told myself was just a (hopefully) harmless kink, out of the fear that if I explored further, I would irreversibly descend that slippery slope. I in my early 50s I finally allowed myself to experiment with makeup and women's clothing beyond underwear. I still vividly recall the moment when I looked in the mirror and saw myself for the first time. In that instant, I may have even said aloud, “I can do this!”

There have been subsequent periods of self-doubt, of course. Still, every day I find that I look forward to seeing myself and engaging with the world as a woman."

Thanks to both of you for the comments! I found many of your ideas to be very profound and meaningful. Plus, I had "aha" moments when I realized I had left all women out of the current political agenda and the moment when I too had realized when I was successful in public as a novice transgender woman that "I could do this", and it felt so natural. Deep down inside, something snapped, and I felt as if I was home.

The night I realized I could do it and felt at home in the company of women was and is so special to me. Just one of the reasons it disturbs me so much to see what is happening today with our rights continue. 

Speaking of continue, I love all your comments and wish I could answer them all, here on the blog in a public setting. Needless to say, I do the best I can!

Also (something I don't say enough) thanks to all of you who find the time and effort to read along on a regular basis. It makes it all worthwhile to me!

Why Not Me?

 

JJ Hart at Club Diversity
Columbus, Ohio

When I was very young, I had the tendency to hide behind my skirts when I needed to deny any masculine pursuits at all. 

Any time I failed, I ran home to see if I could lock myself in the bathroom and apply makeup and try on any of mom's clothes which still fit. I had a dream of finally making it to my own transgender womanhood when I grew older, but I had no idea of how. Back then, little did I know, the journey would take me over fifty years to complete and the path would be so curvy and full of hurdles. If I did, I wonder if I would have ever attempted to try it.

Of course, I started out innocently enough as a cross dresser in a mirror. My reaction was a double-edged sword. One side of the sword told me I was not doing anything really wrong, while the other side wondered if I was the only one in the world doing it. If that was the case, being a transvestite just could not be good. Right? All I had to rely on was my instincts which told me I was on the right path. So, I persisted and stayed on it. Since the only real feedback I had was from the mirror, I needed to rely on it when it was telling me I had advanced on from the clownish drag makeup stage I was into a more acceptable feminine form. At the time, I equated it with painting model cars which I was never good at and I was so proud when I thought I had conquered the basics of makeup. Even to the point of purchasing my own from the newspaper route I had when I was a kid. When my friends were buying model cars, I was buying makeup and loving it. It was not until many years later, would I receive the instruction I needed to really understand the art of makeup, but I was getting by at the time.

Clothes and hair were a whole other problem I needed to try to conquer at the time. With the very limited budget I was on, there was no way I could afford a nice wig all the way to my college years, when I was working a better paying job. In order to buy a wig, I needed the help of my fiancé who bought it under the idea she would possibly wear it. The wig was long and blond and was my cross-dresser's dream and luckily, she hated it, so I inherited it. Even with the abuse I put it through, the wig lasted for years before I needed to finally retire it. Clothes were another problem because again I did not have much money, and these were the days before larger sized women's fashions became available in a younger style. It was not until years later, when thrift stores became abundant, did I finally become fashion independent. 

As my feminine life was coming together, slowly I began to realize transgender womanhood may not be such a reach for me after all. I was beginning to explore all facets of the world as a trans woman and it all felt so natural. The more I attempted and succeeded at in my new life, the less I wanted to go back to my old, boring male world. So, I did not.

I was on a slippery gender slope my path had led me to, and all of a sudden, I did not fear it anymore. Somehow, I knew there was a soft landing out there for me. The stop signs were gone, and I knew at the age of sixty, if I did not try to live my transgender dreams, I would never have the chance and would forever regret my decision. From there, I decided to follow my heart and seek medical help to begin gender affirming hormones or HRT. The hormones forever sealed my trans life, and I never looked back. I always felt my body was looking for the hormones the whole time. Again, a scary gender transitional moment felt so natural. 

Why not me, turned out to be why should not it be me? 

Gender Masks

 

Image from John Noonan
on UnSplash. 

In life, both genders learn early on what masks mean to their existence.

Think of it, at the earliest age, babies have only very limited ways to show their pleasure or anger by smiling or crying. Of course, as we advance through life all of it changes. I could be biased, but I think women in life have an advantage by using masks. 

While boys are squaring off on the playgrounds at school, girls are learning the basics of makeup, if their moms allow it. In many ways, makeup for women provides them with their ultimate masks. Anything from false eyelashes to skin foundations to wigs are permissible. It is not unheard of for a man to wake up to a totally different looking woman after a night out on the town. 

Makeup is not the only way women use masks effectively. I learned it the hard way several times when I was first out in the world as a transgender woman that a smiling face does not necessarily equal acceptance in the world. There were many times I relaxed too early in a situation with another smiling woman and ended up getting stabbed in the back. I fell for her friendly mask and paid the price. The whole process with women with me went back to feminine passive aggression versus the old direct aggression I was used to with men. Eventually, I came to consider the process as just another rite of passage into the world of women and I quickly became much better in being able to see what was going on behind another woman's mask. 

As my relationship with other women grew, the better I became at perfecting my own mask. I started at an early age attempting to perfect my art of makeup. It was all I could do to stop looking like a clown in drag. I stumbled along at my mask efforts before I made it into asking for and accepting professional makeup help. I happened into it during a cross dresser, transvestite mixer I was attending. Part of the mixer was given over to several professional makeup artists who offered free makeovers to anyone who wanted them. I gathered my courage, hitched up my big girl panties and stepped up for help. When the help I received was complete, I could not believe the change. The guy doing my mask had totally removed my old mask and designed a new one. The changes were so dramatic, I even received an invitation to go with the so called "A" list transgender women when they went out to bars after the mixer. To make matters even more dramatic, I was the only one approached by a man in a bar to stay for a drink. For many reasons, I did not stay and drink with him, (another story) but the point was made my mask could compete for a change with the "A" girls who the man ignored. 

The best part of finding my new mask was being able to keep it. The professional makeup guy managed to explain everything he was doing to my face and wig, so I understood it and could replicate it over and over. Once I had my mask, I was able to take advantage of it the same as any other woman would. In fact, more so, because I felt to succeed in the world as a transgender woman, I would need to be better than the average cisgender woman who had been born with a built-in mask advantage. 

Fortunately, I was able to step back and look at my new gender mask from a positive perspective and what it meant from view of a novice transgender woman. When I did, my life radically improved for the better and I understood how masks really worked in the world.

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. 

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. 

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. 

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.

Trans Girl at the Symphony

 

Cincinnati Music Hall

I really don't know why but this experience usually slips my mind. Even though, it is one of the most dramatic experiences I have ever had. 

All of this happened several years ago when I was still attempting to navigate the world as my authentic self for first time. Also, my future wife Liz felt the time was right for me to accompany her to the Cincinnati Symphony Orchestra Christmas concert. The whole idea petrified me, but I could not say no and I set about preparing for what I could wear to a semi formal event. My first.

Fortunately, thrift shopping came to my rescue as I found a very sparkling gown to wear in black. As I prepared by shaving, applying makeup and doing my hair, my nervousness subsided a little as we waited for the Uber, we called to take us downtown to the concert hall. 

When we arrived, my nerves returned as we were stuck in a crowd of people waiting to go to their seats. The only thing which saved me was, no one seemed to be paying me much attention. When I sensed no one cared about me, I began to calm down. As far as the musical performance went, I admit I had never been much a fan of classical music, but I did the best I could to enjoy it, and I did. Once I calmed down. Ironically, I was very calm until the lights came up and intermission began. People were moving around which put me in danger of being discovered as a transgender woman. I was not, and the concert resumed. 

Before I knew it, the experience was over, and I could breathe again until we stopped at a venue along the Ohio River for a drink or two to celebrate the holidays and our relationship together. Once again, my nervousness increased until we settled in at the new venue. Again, we were treated very well. I even used the women's room with no repercussions which was becoming a necessity.

What I learned from the entire experience, I found if I did not try harder to expand my horizons as a transgender woman, I never would. Plus, there was never a better time in my life to do it. Because I was spending my time with Liz, it made the whole time so much more pleasurable.

The concert was only the beginning of me building my confidence in my transgender womanhood. Liz wanted to travel, so I learned to travel and again learn new horizons of fitting in with strangers as a woman. I viewed it as a layered trip to learn more and more about my new world. Most importantly, I learned to interact one on one with other women and basically ignore the men who were ignoring me. 

It all was an important springboard into my future desired life which I had to do in a hurry, since I had such a late start at the age of sixty. I can't stress enough, when I did start, despite my fear or nervousness, I enjoyed it immensely. The entire process, proved once again, I had made the right decision when I chose to live as my authentic self. Plus, I needed to discover for once and for all, who was my true self before I could move on with all the major decisions I needed to make.

As I said before, I had never been a real fan of classical music, but it started me down the path to a beautiful future. 

Always Running

 

Image from JJ Hart

Much of my life was immersed in running from my gender problems. 

As fast as I could, I changed jobs and even places my wife and I lived so I thought would make a difference in my life. The prime example was when I picked up and moved my small family from our native southwestern Ohio to the huge bustling New York City metro area to operate a fast-food restaurant. By doing so, I thought deep down I would be closer to a population which would be more friendly to my cross-dressing desires.  I only made it a year before the culture shock pushed me back to our native Ohio.

In the meantime, I did have several moments when I was in New York which I will always fondly remember. One of which was the night I actually got out of the house by myself without my wife and drove myself out to Long Island for a transvestite mixer I had read about. Once I was out, I had two major surprises waiting for me. The first of which was I was happy I found the venue at all. The second one happened when I tried to get in. There were two women at the door monitoring who got in or not. I was flattered when they refused to believe I was a man at all and asked for an I.D. to prove who I was under all the hair, makeup, and fashion. 

The second most memorable night was again when I managed to be out alone in the world as my authentic self. Quite unexpectedly, I was invited to a Halloween party by one of my female assistant managers. Of course, I did not to think twice before I accepted her invitation and began to plan ahead on what I could wear that my wife would approve of. Finally, I learned she would never approve anything I wanted to wear, so I set out on my own to come up with a costume I would have fun with. It turned out my short tight dress and heels matched perfectly with what the other women in our little group were wearing. Plus, the women were all tall and I really blended in well in our heels.  

As I said, the culture shock of NYC over Ohio wore me down and we ended up moving back. When I did, I immediately fell back into the whole cross-dressing culture I was in before. I was unhappy and hidden away from the world, so I found another place to move to and uproot our lives. The job I was working offered me an opportunity opening restaurants along the Ohio River in southern Ohio. A very conservative area to be sure so I needed to up my cross-dressing outings. Somehow, throughout the whole adventure I grew tired of having limited places to go and wanted another move to improve myself. 

This time, I tried to move back to the Columbus, Ohio area where I knew several very diverse friends in the LGBTQ community, specifically the transgender crowd. Following a lot of work, I finally landed the job I wanted, and we moved again.

Finally, I grew tired of all the running I was doing, and I needed to settle down and face my gender issues head on. It took me until I was sixty to realize I needed to make a change to a full-time transgender lifestyle. When I did, a giant weight was lifted off my shoulders and I went on to start gender affirming hormones or HRT. It was a wonderful way to live. 

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.

Amazing

 

Image from JJ Hart

As I sat and watched a singer do a wonderful rendition of John Lennon's "Imagine" and watched the ball in New York drop to ring in 2025, I had the chance to look back and think about how amazing my life has been.

As in everybody's life, destiny stepped in and took me in directions I never thought possible. The entire process was how I perceive the supposed death experience people have when they die. In other words, they get to see their life pass in front of their eyes. If indeed that does happen, I may have to ask for a little extra time to view all of mine.

Over a long life, I have been so fortunate to experience so many things. Outside the all-encompassing world of gender for me, was when I managed to land a job in the Army with the American Forces Radio and Television Service in Thailand and Germany as a radio disc jockey. To put it into perspective, there were only sixty other troops in the entire Army who did what I did. Since back in those days, we were basically the only connection our listeners had with home, it was a very serious job. 

Once I had served my time of three years and was released from active duty, I needed to take on again my larger issues of gender identity. To do so, I undertook serious research and development. Any time I could such as Halloween parties, I began to explore public reactions to my femininized self. For the most part, people I knew were astounded and I moved on. Perhaps it was my shaved legs which gave me away. Whatever the case, time flew by, and I started to cross dress more and more in the public's eye. Plus, at the same time, I slowly began to perfect my knowledge of fashion, makeup, and hair. I discovered the more I did, the more natural I felt and the more I wanted to do. In no time at all it seemed I was accomplishing tasks such as doing the family grocery shopping as a woman and it felt amazing.

Imagine my surprise when I then discovered I was going through another major gender transition. All of a sudden, I was losing my desire to just look like a woman and I more and more wanted to explore a path to transgender womanhood. Mainly because I was feeling alive and amazing when I did it. Now we all know how difficult a gender transition is for the average human being, and I was no different. I had very few natural feminine characteristics to work with and I had to struggle completely to survive in the life I wanted to live. Especially when I hit what I call the dark period of my life when I lost nearly everyone close to me to death. 

In order to bounce back, amazingly, I was able to rely on my strong inner feminine soul to survive at all. She helped me find my way. During the bounce back period of my life was the time I found a whole new set of women friends to instruct me on how to live my new life. Included in the trio of new friends, was my new wife Liz who I never expected to meet. At my advanced age of sixty plus, I would never find another person to be close to the rest of my life. Especially since I carried so much gender baggage with me. At the time, I still maintained one tentative foot in the male world, until Liz told me she did not see any male in me at all and what was I waiting for. Go ahead and fully transition. I was amazed and still am since it was over thirteen years ago when our relationship happened and is still going on strong today. 

The end result of watching the ball drop to welcome the scary year of 2025 was I have been so fortunate to have led an amazing life so far. Mainly because destiny has been on my side, and I have lived long enough to accept it.