Saturday, March 8, 2025

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.


Friday, March 7, 2025

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.  









  

Thursday, March 6, 2025

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. 


Wednesday, March 5, 2025

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.

Tuesday, March 4, 2025

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. 

Monday, March 3, 2025

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. 


Sunday, March 2, 2025

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. 

Saturday, March 1, 2025

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.


Friday, February 28, 2025

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.

Let the World be your Classroom

  Image from Aleksandar Andreev on UnSplash. It certainly is difficult to reach a space in gender time when you can relax and let the world ...