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. 

Writing Your Own Script

Carla Lewis

 It is difficult enough to go through life trying to live up to the expectations of others around you. 

In my case, and maybe you too, you struggled under the burden of living up to the demanding expectations of a male world. Perhaps, you achieved some sort of success in the male world as a method of self-survival.  Bullies were everywhere and ready to pounce and you had to be ready. I used the world of sports to hide the fact in truth I wanted to be a woman as I progressed through life. An example was, when I was playing football on the high school football team, I would stare longingly at the cheerleaders who were practicing nearby. Of course, it was my deep, dark secret about how badly I wanted to be one of them. 

About that time, destiny set in for me and it was time for me to step up and serve in the military. Little did I know, later in life, all transgender military members would be banned from serving by a self-serving draft dodger.  Or as trans woman "Carla Lewis" famously said, "I fought for your right to hate me." Now, it is even worse. I fought for your right to ban me.

Regardless, I kept my head down and served my time in the Army. I never labored under the impression the experience would make me a better "man." Looking back, as I was writing a new script in life, the entire process made me a better woman. Why, may you ask? Mainly because I was taught in basic training what extremes I could endure and adjust to in the military. Plus, I learned to always look ahead in life and not backward which would serve me well as I became a serious cross dresser. When I hit the rough spots which always come when you try to cross the gender border, I used my military lessons to always go back to the drawing board, try harder, and move forward. 

When I did move forward into a new scary, yet exciting life, writing my script became so much more intense. I needed to just to get by. For example, what would I do when I needed to put the carefully crafted feminine presentation I put together over the years into motion. The need to move like a woman and communicate with other women were and are prime examples. To make matters worse, I had no workbook to work from. I was completely on my own and made my share of mistakes before I began to be successful.

As you progress with your own life's script, adding being transgender into it adds a certain amount of intrigue. Especially, these days when we are under attack from so many politicians.

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.