The Grand Search for Discovery

 

Image from Gints Gallis
on UnSplash.

Along the path to transgender womanhood, I made many discoveries. 

It wasn't until I finally made it into the world did, I begin to pick up the pace in being allowed behind the feminine gender curtain, so I could learn for myself what was going on. In other words, I needed to earn my stripes as a trans woman to be allowed in to play in the girl's sandbox. Now, I can't quite remember what my expectations were of being allowed in, I only remember I basically forced my way in. Many times, causing the sand to really fly. 

I discovered most other women accepted me for myself and let it go at that, and I learned quickly to let the others go on their own way. After all, you cannot please everyone at the same time. Plus, the acceptance I gained far outweighed any negatives I experienced. I discovered once I made it past the idea I was attempting to "fool" anyone into thinking I was a cis-gendered woman, the better off I was. When I was satisfied to just be myself, more women reacted to me positively. Probably because they appreciated, I was being truthful with them. I was just busy learning how to live my dream and meant nobody harm.

Even still, my gender path was very winding, and steep with many roadblocks. Similar to many of you, I experienced the pain of separation from family, friends and life in general as I transitioned and femininized myself. Many times, I needed to stop and rest on my path because the effort exhausted me.

Out of all the discoveries I made, one of the biggest ones was when I made the transition from weekend or parttime cross dresser to novice transgender woman. Even though I was just dealing in basic gender semantics, the shift in thought was a major one for me. All of a sudden, I began to feel I was achieving my childhood dream of being a woman. Not just looking like one. When I did make the discovery, to change my life, my path ahead became fairly well illuminated. Now, I had the usual hurdles to jump through such as how to make my way out of the mirror and into the sandbox but overall, I had the confidence to move forward.  

The other main discovery I made as I entered transgender womanhood, was how important the gender affirming hormones would be to me. Of course, I knew the physical changes I would go through such as changes to my body such as breast growth. However, nothing prepared me for the internal changes which would go on. All of a sudden, for the first time in my life, I could cry tears of joy as well as sorrow. In essence, estradiol softened my entire life and quickly took the testosterone related universe I lived in away from me. A huge discovery. 

Of course, every discovery does not have to be a good one. When my second wife discovered I was sneaking out of the house to live as a transgender woman was certainly not a good discovery for me. It took me weeks of apologizing and even therapy to save what was left of our twenty-five-year marriage. Which I managed to do until she unexpectedly passed away. When she did, I discovered what loneliness was all about. 

Every human life is filled with discovery if you are living it right. It seems transgender women and transgender men live have an extra amount of discovery. It is very rare a person who has the chance to explore the two binary genders to determine which one they want to live as. I feel it is one of the reasons so many people these days misunderstand our trans community and treat us poorly or even with hate. We have found how deep trans bigotry suddenly runs in our country, led on by a certain felon as president. Which is all I am going to say about it. 

In the meantime, I hope all your discoveries are positive and exciting.

Should You Be a Jumper?

 

Image from Jeremy Bishop
on UnSplash. 

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

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

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

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

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

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

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

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

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

Preparing for the World

 

JJ Hart. Witches Ball Image.

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

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

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

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

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

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

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

Born This Way

Image from Vonecia Carswell
on UnSplash. 

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

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

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

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

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

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

I Was Ready but Was the World?

 

Image from the Trolley Stop, Dayton, Ohio

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

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

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

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

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

  

Real Life Impostors

JJ Hart at Key Largo.

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

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

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

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

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

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

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

Gender Lighthouse

 

Image from Juan Gomez
on UnSplash.

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

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

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

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

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

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

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

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

From Obsession to Passion

 

Image from Kayshawn Herandez
on UnSplash. 

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

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

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

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

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

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

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

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

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

Why Not Me?

 

Image from Danielle
la Rosa Messina on
UnSplash

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

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

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

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

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

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

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

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