Showing posts with label transgender men. Show all posts
Showing posts with label transgender men. Show all posts

Thursday, May 21, 2026

Staying Calm as a Trans Person

 

Image from Matteo Vistocco
on UnSplash.

Many times, during our lives as transgender women and transgender men, staying calm in the face of adversity is not easy.

Perhaps the worst time I had staying calm ever in my life came fairly early on when I encountered a hostile, aggressive woman in a rest room I was simply using to pee. It all happened by accident when I was looking at the door of the women’s room at a venue where I normally had no problems, so I could judge when the room would be empty and safer to use. I had judged correctly, and the room was empty when I entered it and I had my choice of stalls. As I finished the business I came for, I left the stall and started to wash my hands when this woman burst through the door and started calling me a pervert, My first reaction was shock because I had never had any problems before from the staff when I used the woman’s room in that venue. Then, I became angry that this woman who was a total stranger to me was calling me a pervert.

My mind was turning quickly as I fought to stay calm and say something to the angry woman who was completely out of control and fortunately, she gave me the insight to do it. Somehow, in our brief conversation, I got out of her what she did for a living, and she said she owned her own beauty parlor. When she did, I asked her for a card so I could report her business to the very strong and influential LGBTQ organization in town during those days. I never got her card as she turned around and stomped out of the restroom, and I only saw her one more time walking past me in the venue. I glared at her as she refused to even make eye contact with me. So, at that moment staying calm (no matter how hard it was) worked for me.

It is my opinion that the ability to stay calm mainly comes from having confidence in yourself. Normally from years of interaction with the public as your authentic transfeminine self. Like anything else, confidence is very fragile and can be destroyed at any time as you advance up your gender path. You might think you have done the best makeup job ever and was able to find a comfortable outfit which really flattered you, only to find out it did not and you needed to go back home and try again to reset your confidence. There would have been no way early in my life that I could have ever survived the bus tour vacations that my wife Liz took me on where I needed to interact with many different ciswomen on the trip and get along with them in all the restrooms we encountered.

After I enhanced my feminine appearance and attitude with the HRT or gender affirming hormones I was approved for, I discovered a new calmness I had never known before in my life. Which probably came from the hormones themselves, and the fact I was no longer battling being something I just wasn’t. I had achieved all the male accolades and benefits I had ever dreamed of but then did not want them. And I was surprisingly calm when they all went away, never to return again.

Another big surprise was how calm I stayed when I was making more gender transitions in my life into my own form of transgender womanhood. I negotiated all the phases such as being terrified on occasion when I tried out new venues, all the way to when I was making several unexpected transitions, I did not see coming. Even though, I knew what was coming if I was able to survive or even be successful when I went out for the first time at “Fridays” to mingle with ciswomen just getting off of work at a nearby mall, I knew I could never go back to believing I was some sort of a weekend cross-dresser who wore women’s clothes as a hobby. It all was an extreme revelation to me, and I had a very difficult time staying calm through my whole adventure.

On the other hand, staying calm was much more difficult when it came to how fast I was being accepted in my desire to carve out my own transfeminine life. The public was accepting me way too fast and challenged my life and communication skills that I was always putting off. All my procrastination did me no good as the world came crashing in around me and I needed to do things such as feminine vocal lessons to catch up. Thankfully, the world gave me the chance to catch up and again I return to the new calmness I was feeling. These were the days when I was learning almost daily what I would need to do to survive as a trans woman in a sometimes-hostile world. Obviously, I did not want to be called a pervert again for simply wanting to pee. Perhaps I paid my dues, because nothing remotely coming close to that ever happened to me again.

Perhaps also, I am not giving the impact of the HRT hormones enough credit. Even with the minimum dosage I began with, I could feel substantial changes in how I viewed the world. The hormones simply took my male edge off and mellowed me right out like I had always been destined to take them.

Over the years, I have learned to try to separate the always present anxiety I feel about everyday life from the new calmness I have developed over the years. Which in turn has helped my fragile mental health. Which has been quite an accomplishment. Hopefully wherever you live, the anti-transgender pendulum has begun to swing back the other way for you. Even here in Republican led backwards Ohio where I am from, the leading anti-trans bigot in the legislature has his own problems after news surfaced of him being in bed with an underaged girl. Sounds familiar. Right?

Maybe the future is not so dim after all since the world is waking up to the fact that the transgender population is not the problem after all and the rest of the population needs to stay calm around us.

 

 

 

 

 

Saturday, May 16, 2026

Chance versus Choice as a Trans Girl

 

Image from Brooke
Ballentine on UnSplash.

Chance versus choice for a transgender woman or transgender man can cover a wide spectrum of activities.

Chance included all the times in my life when I risked the very future of my male existence to attempt to live in the world as a new cross-dresser or trans woman, before the term was even invented. Choice included all the times I threw caution to the wind and took on the new world I was experiencing anyway. Deep down, I took the chances because I knew sooner or later, it would be the right thing to do and I could live full time as a transfeminine person.

Even still, it was never easy for me to take all the opportunities I had gained from simply practicing the artform of making myself up to be a convincing enough woman that I could blend in with most of the world. I found a large percentage of the population were in their own universe and did not care about mine anyhow. Then there was the number of people who were curious about me and wanted to know more about why I was switching gender clubs from male to female. Finally, there were the hateful bigots I tried to stay away from who for some reason saw me as some sort of threat to them.  The more chances I was taking, the easier it became for me to survive.

At this point, to make myself very clear, it literally took me decades to arrive at the point where I had a choice to be myself as I was very slow in deciding if I was making the right decisions in my life. As a parttime cross-dresser, I was basically providing myself with stop-gap measures to relieve myself of the pressures of living a male life I never should be living. I was stuck in the middle with me, and it was not a pleasant place to be. All that got me by were the brief moments of gender euphoria when I was able to navigate the world as a trans woman. But the biggest problem came when I began to experience my own form of impostor syndrome.

I was still enough of a man, operating successfully in a male world to not want to give it up, yet I was becoming enough of my own woman to keep moving forward. It put me in a bad place when I went to invites to girls’ nights out and in the middle of the evening suddenly felt as if I did not belong. In a relatively short period of time, I was able to work my way around the dreaded syndrome and relax and enjoy myself. I had as much of a right to accept the invitation as the next woman at the table as we enjoyed our combined femininity. The entire experience was so different than anything I had experienced at all the men’s parties I had ever been to that I could not wait for the next invitation to come in my direction.

When I was able to overcome my imposter syndrome, I was able to take advantage of having more choices while taking fewer chances. Most of the time, it came from knowing the venues I was going to and knowing ahead of time I would be accepted. Sure, I needed to take chances and choose new non-gay places to go but I desperately wanted to go to venues which reflected my tastes. My wants were simple, I wanted to drink draft beer, watch sports, use the women’s room when I needed to and be left alone. Which I found out that I could in several places, so I had a choice of where I wanted to go. I was living large as a trans woman with choices for the first time in my life.

As chance versus choice began to fade in my life, the choices began to take on extra meaning. I still had what was left of my male life to deal with and he was hanging on for dear life and fighting on to the end. He was tougher to give up because when he went, so did all my old white male privileges out the door with him. No job, no wife and possibly no family awaited my decision on which way I was going to live. Naturally, all the pressure wrecked what was left of my fragile mental health until destiny set in for me and overcame my chance versus choice idea altogether.

In a dark five-year period, I lost all but one of my closest friends to death including my wife who was the major drawback to my male to female gender transition. At the same time, I came out to my only child (daughter) who became my closest ally until my wife Liz came along. Add that to the Veteran’s Administration health care system announcing that they would start the process of administering gender affirming hormones or HRT to veterans who qualified and I did, so I was made an offer I could not refuse and began the process of closing out my male life completely. Destiny could not have made my path any clearer if it tried and I needed to seize the opportunity while I still could. Because I was near the age of sixty at the time. I needed to make my decision to live as a transfeminine person and not look back or forever try to live as the gender juggler I was. Which I could do no longer.  I needed to take the right way out and choose the one I should have always chosen.

I think all humans, trans or not face the chance versus choice decisions in their life, but it seems we transgender women and transgender men face more deeper challenges than most others. We risk our jobs, our families, our marriages and even our lives to live our truths, and few emerge from the process unscathed. Best wishes on you making it up your gender path the best you can. There can be brighter days ahead out of your dark, lonely gender closet.

 

 

 

 

 

Friday, May 15, 2026

When Every day is Day One

 

JJ Hart

We all know how difficult being a transgender woman or transgender man can be. For years, it seems as if you are starting on day one when you are trying to catch up with ciswomen who have lived a feminine existence their entire life.

For me, my journey started when on certain mornings when I did not know if I was going to be a boy (physically) or a girl (mentally) that day. My thoughts often came from vivid dreams I had from the night before that I was living a life as a pretty girl. I just couldn't shake the idea that something was wrong in my life, and I couldn't do much about it except occasionally cross dress in front of the mirror in mom’s clothes and makeup. When I did, early on I needed a lot of help with my makeup and everyday when I tried something new on my face, I was starting all over again. Plus, it did not help that most every time I cross-dressed, it was an adventure in not getting caught. Between my parents and my slightly younger brother, earning my private time to be on my own and be a girl was difficult.

It took me years to shake the idea that every day as a transwoman was still day one in my life. Mainly because, I was still learning so much from all the ciswomen I was around in my new world. I had plenty of stop signs on my gender path I needed to negotiate as I made my way towards my dream of living full-time as a transfeminine person. Some of the stop signs were busy four way stops when I really needed to stop, look both ways, and make the difficult decision to proceed. Looking back now, I don’t know how I managed not to have any major collisions with anyone but my second wife who unfortunately had a front row seat in my transition from just cross-dressing on a part-time basis all the way to considering HRT or gender affirming hormones as a transgender woman.

What kept me going was my deep-seated knowledge that what I was doing was right. All the cross-dressing I was doing was just practice towards a bigger, brighter future as a trans woman. Looking at it that way was certainly difficult, but it was all I could cling to if I was to keep my fragile mental health intact. As my wife told me when we were fighting about my gender that I made a terrible woman. So, I needed to find out what she meant because she added that she was not talking about appearance which I thought I was doing better with.

I set out at that time to re-dedicate myself to understanding a woman’s life. I was naïve at the time and thought I could learn more while I was still presenting as a man fulltime. Years later, when I had crossed the gender border publicly as a trans woman, I finally was invited back behind the gender curtain so I could learn a lot and not be a terrible woman. For most of you who do not know, my wife unexpectedly passed away from a massive heart attack after twenty-five years of marriage to me and she never was able to see the better woman I had become. Mainly because my time behind the curtain enabled me to start all over again and mold the new woman, I wanted to be. Including most of all the nuances and the layers a female must live through before she becomes a woman. My inner female was forced to stay back and be dormant for all those decades before she could claim her ultimate gender prize also. She just had to take a vastly different path to get there.

At that point in my life, everyday was day one again when I donated all my male clothes and vowed to never look back again at my male life. Which I ultimately found impossible to do. Male influences built me into the person I had become as a transgender woman and made me stronger in the process. I even brought experiences from the most male dominated part of my life to my gender table as I remembered the days I went through in Army basic training. There was no need to throw away valuable experience I could use in my new life.

It turned out to be the most exciting time of my life when I could finally live my truth in the world. And I was able to forget the dark days of my youth when I began to deeply question what gender I was. Having all the help I did to finally begin to fill out my gender workbook helped me too, even though I was rejected on occasion and needed to start all over again. I urge all of you who are considering a journey in life the way I did, is to be resilient and expect many ups and downs along the way. Most are just learning experiences anyway and can be valuable as you are allowed to play in the girls’ (or boys for you trans guys) sandbox. It takes time and experience for your confidence to grow as you navigate one of the most difficult paths a human being can take.

Slowly but surely, every day will not feel like day one as you get used to living a full-time life you have always dreamed of in a gender world you want to be a part of. For me, it was like taking a great deep breath of fresh air when I was finally checked out and was able to begin the long-awaited HRT which would transform my body outwardly and more intensely, inwardly. My entire being was telling me what took me so long when the male to female feminizing hormones hit my system. But I did not need the hormones to tell me who I was, they were like the icing on my transgender cake and made every day a better day.

 

 

Tuesday, May 12, 2026

Success is no Accident in the Trans World

 

Image from Priscilla du Preeze
on UnSplash. 

Success is definitely no accident in the world of transgender women and transgender men. Very few of us survive our puberty by having no natural characteristics of our authentic selves that we want to be.  I know I wanted nothing to do with the size and angles my male body was willing me to have without my permission.

It was not until I became very serious about my male to female femininization project did, I take the necessary steps I needed to take to begin to ensure my future successes were no accident. The first step I took was to try to make myself smaller for I could fit into more stylish feminine clothes. Naturally, all I could do to make me smaller was to go on a diet. I was successful in a short period of time because I had a very active job and my high male metabolism was still working well. I ended up losing nearly fifty pounds quickly and had the fun job of going back to the thrift stores and searching for new clothes in my size and trying them on.

The next step I took to improve my work to become more feminine to the public was to take better care of my skin. Every day I was careful to moisturize my face after I shaved to make it easier for me to use less makeup because I knew less was more when it came to using makeup. It was a start but was all I could do without the public and my wife beginning to notice a major change in me. Even so, I was proud of the beginning steps I was taking towards my overall femininization.

It proved to me that over the long haul, none of this path I was on would be easy to navigate as I sought to cross the gender border. Also, what I did not know was how much more difficult my life would be because just looking like a ciswoman would not be the end result of the process. It would just be the beginning when I left the mirror and challenged the world as a novice cross-dresser or transgender woman. I never realized the depth and scope of the world women use to run their lives. With or without the help of men.

By accepting the challenge of femineity I was seeking, I was also challenged to move like a woman and more importantly communicate as a woman because I discovered quickly how many other women wondered what I was doing in their world. From the ease of dealing with clothing stores clerks to having conversations with women at restaurant/bars I was at, I found I was dealing with much more interaction than I ever had as a man. My new success was no accident, but I needed to work hard to keep it and always stay aware of my new surroundings. One slip up and the setback could be tremendous and discouraging to my dream goal of being able to live full-time as a transfeminine person.

Many times, my frustration grew over the decades that I struggled with my gender issues. Was I going too fast by going out into the world, or not enough to keep learning what I needed to know to progress along my gender path which kept showing me infuriating stop signs along the way. Particularly from my male self who was becoming very successful in his business world. He was making it difficult to choose between his growing male privileges and living the life I had always dreamed of. Ironically, it was lessons he learned at work which were carried over to my female life that proved that success was no accident. If I wanted my goal bad enough, I could achieve it.

As I progressed with carving out my new feminine life as a trans woman, I found that my successes were painting me into corners which were difficult to get out of. I had nights when butch lesbians were flirting with me and buying me drinks until I ran out of time and had to be back home before my wife was take my makeup off then calmly try to wind down by watching television. I was on the gender rollercoaster going from one high to another and eventually it was too much to take.

Before I broke for the final time and had to make a decision between staying with my wife as a man and deciding to live my life as a woman, she took my decision away and suddenly passed away. Leaving me all alone with my other woman who happened to be me. It took a while for the shock to wear off, but when it did, my internal female took right over and claimed her territory in my life. She thought success was no accident and she had claimed hers by paying for those dues all those decades when she was hidden for the most part. In the light of day, she flourished and never looked back. Especially when HRT or gender affirming hormones were introduced into her old male system.

The ultimate measure of success is coming around and transitioning ourselves from transgender into just being ourselves. Many of us have to go through extensive gender realignment surgeries to do it, and some not but that is OK. Whatever makes you whole as a person is the final key to the lock or piece to the puzzle. I am sure that whatever the case, everyone who succeeded in finding themselves would agree that success was no accident. They had to work hard to achieve it.

If you are on your path, just keep up the hard work you are doing, and you can find success also. Pursuing such a complex journey will never be easy but as the saying goes, if it was easy, would it be worth it.

Thanks to all of you who read along with my posts! All your thoughts, comments, claps and subscriptions are always welcomed.

 

 

 

 

Monday, May 11, 2026

The First Time

 

JJ Hart

There are plenty of first times in a person’s life that we can set up on a pedestal and remember. Such as, the first time you had sex or the first time you drove a car can create some memorable experiences.

I venture a guess that we transgender women and transgender men have more than our fair share of first times to look back on. I know I do. For example, I remember vividly the first time I went exploring in my mom’s garment drawers, and deep down something clicked inside me that I was on a new and exciting path I could never get off of. I also remember the first time I drove a car on a country road at the age of fourteen when no one else was around and I remember the first time I had sex with a woman, and she told me that I would never forget her and she was right.

For many reasons, these were the easy firsts to remember other than times such as when I was in the delivery room for the birth of my only child and negative ones such as when I needed to go to Ft. Hayes in Columbus, Ohio for my draft induction physical. Standing in a room full of naked men was not my idea of fun and a first time I did not want to revisit. There were also lesser first times such as graduating college and receiving my honorable discharge from military service that I was proud of but not as much as I was when I started to fill out my gender workbook and begin to advance towards a stable transfeminine future. It was only then that I began to grasp the importance of life’s first times that I was sometimes racing past before I even knew it. I was so bad about not living in the present and appreciating it for what it was. I was always thinking about the future before the present was over.

When I began to search for my feminine self in the world, I needed to stay in the present more than I had ever needed to in the past. If I did not, I would forget what I was trying to do that night as far as being a novice cross-dresser or transgender woman. I could be mirror-ready with my clothes, makeup and hair and still destroy that image with the wrong movements if I became too careless and forgot where and who I was. Who I was, was the most important time of my life as for the first time, I was attempting to see if I could (against all odds) survive a dream run towards my goal of living as a trans woman in a world of ciswomen everywhere.

As I did become successful, my mindset began to change, and I started to think of myself of a transgender woman more than some sort of a casual cross dresser. I knew it was completely a mental move but still a very important one as I scaled the steep walls of my gender path. At the time, the term transgender was just being used more and more, and for the first time in my life I found something that really described who I was. All those years I had gone to those “Tri-Ess” cross-dresser social mixers were wasted because I still came away with the idea that most of the others were not like me. It took me a while, but I finally began to appreciate the individual that I was for the first time. When I began to remove the cross-dresser word from my mental vocabulary, I was beginning to insert the use of woman and inwardly began to refer to myself as a she, became a milestone in my existence because I was coming to the point of understanding for the first time, I was a woman. Just one with a unique background which should be celebrated, not scorned.

My only problem I had with the whole direction I was heading in my life with my feminine self was that the potential I had to hurt others I loved in the process. And if I had followed my instincts and done the male to female transition, would I had been better off in the long run. For the first time in my life, I felt as if I was wasting my life as a man. What was left of it was only the physical image I presented to the world when I worked and when I was around friends. I was still under the impression I needed his male privileges to exist in the world which were nice to have in the short term but had to go for the first time when I decided to transition into a new, exciting transfeminine world.

Not to say the new world did not present constant challenges to not slip back into my old ingrained masculine ways from living nearly fifty years on and off in that world I was born into without a choice of getting out of. It seemed I was in a dark closet I could not get out of until I made more than a few serious efforts such as going out and carving out my own new life with people who knew nothing of my past. For the first time, I made it in a world full of ciswomen who saw nothing wrong with me being behind their gender curtain and it was as if I had always belonged to the new world I was in. Which was true, I had never been able to get there until I took chances and made the effort. Of course, back in those days, the world was in essence a kinder and gentler place with people less inclined to be in others business.

In my male life, I had always been quite guarded because I did not want anyone in my gender business. As I went female, everything changed and I did not mind anyone knowing my big secret. I was a woman of a transgender background, and I found people who respected me for my honesty on how I was living my life. For some reasons, especially lesbians who let me into their world, and socialized with me as we were regulars watching sports in a few big venues and regulars for the first time at lesbian mixers, I was invited too. In fact, often I was a better “mixer” at these socials than my friends were. I was having fun for the first time in a long time in my life.

I was moving so fast, I finally had to slow down and think of how far I was able to come with the help of my small circle of friends and my future wife Liz. I needed to work on staying in the present for the first time in my life I had a present worth living for, not just going through the motions.

Thank you all for staying with me through all my experiences, and responding with claps, comments and suggestions. As I always say, without you all, none of this is worth it to me.

 

 

 

Saturday, May 9, 2026

Graduation Season

 

Image from Logan Isbell
on UnSplash.


It is graduation season around me, and it brought up all sorts of memories of my own graduations. Many far from the usual school graduations everyone thinks about when we think about moving on with life. Plus, it goes much further than just thinking about the pretty new fashions women get to wear on their celebration days. If they choose to do it.

When I look all the way back to my high school graduation days, I always tie it with the prom season which was very close to it. My senior year was actually my second prom, but nothing really changed. I was still very envious of my date’s beautiful prom dress and corsage (which I had to buy her) to add insult to injury. No matter how hard I tried, I wanted the high heeled shoe to be on my foot and not hers and I would be taken out for the evening. Graduation was not as bad as prom because every graduate had to wear the same black gowns, hiding their new fashions until they went to an after-graduation party. But, even so, I still had misgivings about what I was facing following my graduation. As I faced hurdles such as surviving college and the military service which sometime made my gender issues pale in comparison.

Even though I realized a college graduation was in my future too, I did not think of all the other times I would have to graduate in life to survive. Examples included the times in the Army when I needed to graduate basic training all the way to making my way through the “Defense Information School” in Indianapolis. Time was flying by as I transitioned from the college world to the Army and back again three years later when I pursued my second college degree. Aside from brief moments of regression and purging, my desire to be a transfeminine person never went away and was in fact getting stronger. Little did I know I was facing more graduations confined only to how I viewed myself as a person.

Backtracking a bit and going back to my very first time I saw myself in girl’s clothes and makeup in front of a mirror. I realized I had graduated from being a so called “normal” boy forever. Plus, there would be several future gender graduations when I transitioned from being a cross-dresser to a transgender woman and when I began to take HRT or gender affirming hormones under a doctor’s care and took another major step towards my dream of being a fulltime trans woman.

By the time I had gone through all these graduations, even I would have thought I would have grown tired of the process. But I did not. I started to crave the next step in my occupation and my life as a transgender woman. Which put me on a collision course for my future. It came down to which one I would save after the major gender collision in my life. Following years and years of success, one would just have to go. Just trying to look ahead up my winding gender path became a major problem as increasingly carving out a life as a novice transfeminine person on my own terms became a priority over every thing else, I loved in my life.

At this point, my graduations began to slow down and became smaller in nature. Every time I was successful at trying to be the person I always wanted to be, I celebrated my own mini gender victory and resolved to do better on my path. No longer did I have to be envious of the ciswomen around me, since I was allowed to be behind the gender curtain. Which was another graduation for me, as I loved it. It was a major reward for all the work I put into filling out my gender workbook. As a matter of fact, it was the best graduation I had ever had in my life.  If I wanted to, I could wear the pretty dress all the other women around me were wearing.

Until then, I think I was taking all the graduations and transitions I was taking for granted. I was not raised to think anything I did was good enough, so being pleased with my progress towards my dream and being happy about it was a first for me. Ironically, I even was able to use the same restroom in the dinner club I took my second prom date to years later when it became a gay venue. It was as close as I could ever come to reliving the inadequacies I felt so long ago as I looked at myself in the women’s restroom mirror.

Humans are blessed to be able to graduate to many different levels as they transition through life. It is sad because of whatever reason, some people (men and women) are never socialized to make it to a point when they can claim the status of being a man or a woman. They are doomed to never making it past the stage of being male or female and never took the opportunity to graduate to the next level of life. They are the ones who are jealous of and hate transgender women and transgender men for reasons they do not even understand. Often, they are stuck in the past and never have the chance to escape.

If you are busy trying to figure out your next stop on your gender journey, I hope you can take the next careful step and graduate to the level you want to be. In the end, graduation is much more than having a framed certificate for your wall and who would consider having a framed certificate saying you made it to your own form of womanhood above your desk anyhow. Wouldn’t that be something?

Your destination should be your own sense of satisfaction or even happiness because you undertook one of the most difficult journeys a human can take. Congratulations!

 

 

 

 

 

 

                                       

 

Friday, May 1, 2026

No Laughing Matter

 

Image from Priscilla Du Preeze
on UnSplash. 

I am always amused when someone thinks I had a choice to follow my transgender path. Obviously, they were not there for all the trials and tribulations I had and the extreme harassment I received as I came out into the world. All the times I hurried home crying when I was stared at or glared at by the public before I was able to improve my feminine presentation to the point where I could blend in.

I did all I could to improve my testosterone damaged body by going on a crash diet and did my best to improve my skin by using moisturizers everyday after I shaved before I went to work. Why would I attempt all of that if I thought crossing the gender border was just a choice I could make. The farther I went, the more I had to do to improve. Mainly because it felt like it was the right thing to do.

Perhaps the most important sacrifice I needed to be prepared to make was losing my white male entitlements or male privileges. Even though I did not respect the growing rights that I had obtained through hard work as a male, I needed to keep in mind continually I did not really want them anyhow and there were better days ahead if I ever had achieved my dream of living as a transgender woman fulltime.

Through it all though, I wondered why all this gender turmoil was happening to me. Often when the poor, poor pitiful me aspect of my life was at it’s worse, I would “man-up” and purge myself of most of my feminine belongings. As most of us know, purging does not work for any length of time. All it did for me was make me go out and buy more makeup, clothes and shoes to express my femininity again. A total waste of money, but at least I always tried to build back better following every purge I tried. Finally, I looked back at purging as just another rite of passage I needed to through as I followed along my gender path to success, and I was able to put my transgender victim mentality behind me.

As I grew older and set in my cross-dressing ways, I knew increasingly I had no choice in how I lived my life. I was rapidly going through yet another gender transition from just having a so-called hobby into being a transgender woman. I was doing more than just shopping for more and more clothes and was trying out new ways to experience the world the way ciswomen do. I started doing a portion of the grocery shopping successfully as the new transfeminine me all the way to starting to do all my Christmas shopping in unique situations also. Just to see if I could.

At that point, the things I needed to go through to survive in life became increasingly evident to me. I would need to express myself as a woman and I had no choice but to do it. I also knew the risk I was taking when I thought about losing the male life, I had worked so hard and long to be successful at. What would my daughter think of her new dad was one of the few variables as I knew I would lose my long-term marriage and great job that I had. I needed to know beyond a shadow of a doubt I was doing the right thing, and I truly had no choice but to stay on the course I was on. This is where my transgender humor comes in. Why would anyone ever put themselves through such a life full of turmoil if they ever had a choice. Or, when just putting on a dress becomes so much more than a fun experience, where do you go then?

It is no secret where I went and I had the chance to experience so much more in my life because it is exceedingly rare when a human gets the chance to experience both sides of the binary gender spectrum. The problem is we transgender women and transgender men don’t have a chance to enjoy the trip because of the pressure we put on ourselves to perform behind the gender curtain we chose. If we are not doing it to ourselves, the pressure is certainly on from the public to do it too. Especially these days with the charged anti-transgender political attitude we are seeing from the orange menace in Washington DC, and in many states such as my own native Ohio.

If we can ever get the public at large to understand we trans people never had a choice on the life’s direction we ultimately took, we would come out so much further ahead. Sadly, the path to get there does not seem to be getting any closer for many of us as the things we have to go through just keep on coming. I know for those of you who are still on your transition path or even consider it, it is a major step to take. Hopefully on the way, you can take the time to stop for a moment and enjoy how far you have come. I always thought if it does not kill me, it will just make me stronger would help me along. And on a lesser scale, the old sticks and stones may break my bones, but words can never hurt me saying really applied to me also.

When you are on your path long enough to realize there is no turning back, you will also know you had no choice but to keep going towards your goal. It was never easy, but so worthwhile as you navigated the final blind curves, potholes and stop signs. At the least, you will know you lived a life where you had a choice and made the most of it.

Plus, certainly it was no laughing matter. 

As always, thank you for reading along with my experiences. Any comments, extra claps or subscriptions are welcome!

 

 

 

 

Wednesday, April 29, 2026

Connecting the Gender Dots

 

Image from Beya Yurtzkuran'
on UnSplash. 

Connecting all the dots in a life when you have gender issues is never easy.

Especially so when your life’s workbook is completely blank and you have nowhere to go but to struggle. The great majority of transgender women and transgender men grew up with unapproving parents and/or no peer group pressure to shape our gender youth and help us along. At the best, the closest dots we were trying to connect were fuzzy and far away.

On the other hand, with me, my male dots were always crystal clear and easy to at least try to connect. If I was successful on a sports team, I would connect an easy dot is a great example. But if I was cross-dressing as a girl in front of the mirror, I was always confused on how I should act or feel. The only certainty I had was I knew I wanted to feel pretty.

As I progressed through life’s lessons, I learned the impact of achieving the connecting of my feminine dots while at the same time, leaving my male ones behind. Sacrifice became the ultimate name of the game. Especially when my second (out of three wives) kept calling me selfish for my complete pursuit to begin to leave my male past behind and live as a complete transfeminine person. What made matters worse was the fact that my gender dots on both sides of the spectrum were becoming clearer. I was becoming more successful as a father and as a provider as I advanced in my chosen profession, but at the same time, I became better and better at presenting myself as a convincing woman. For the longest time, my dots formed a parallel path. Heading ultimately for a collision.

I was stubborn and tried to separate the dots I was connecting until it affected my mental health so badly I could do it no longer. I was like a juggler trying to balance the two main binary genders as fast as I could and it nearly cost me my life. I was finding it harder than ever to separate my old unwanted male self from my new exciting yet terrifying new feminine self when one side began to bleed into the other. For example, when I was in a company meeting full of men, I would daydream how it would be if I was there as the only woman. Before reality would slap me down and back into the present.

Finally, I could take it no longer, and I began to give up on connecting any more of my male dots at all. I figured if I connected any more dots, it would just create more baggage I would have to deal with when I male to female transitioned. Mentally, I began to make contingency plans on what to do when I could ever connect my female dots and live out my dream. It is when I began to kick my experimentation portion of my life into high gear. I wanted to make certain as little as possible would be standing in my way as I moved forward in life. I needed to deal with the possibility I would lose contact with my wife and family then figure out what I would do to support myself financially. I was fortunate when my daughter stuck around to support me when my only remaining blood relative (brother) did not and I was old enough to support myself on an early social security retirement I earned and selling collectables my second wife who tragically passed away, and I collected over the years. So, I had connected all my obvious dots fairly well.

From there, the most challenging aspect of life I needed to face was the actual one on one daily living a trans woman has to take on. Learning the lessons a ciswoman is raised to know as she transitions from a female to a woman. Such as the shifting from white male privileges to the female privileges that I had only had the chance to dream about and not know because I had never been allowed behind the gender curtain. Once I was allowed behind the curtain, many aspects I never fully realized ciswomen actually go through became a reality to me. I was connecting my dots and maturing into the transgender woman I always dreamed of becoming. All my misconceptions about just achieving the appearance aspect of femininization faded away as I learned there was so much more to me than just trying my best to have an attractive face. It was quite the shallow existence for me as I needed to develop myself into a quality new human being that the world reacted to on a everyday basis.

As it turned out, HRT or gender affirming hormones took final care of the attractive part of my being as I went from being attractive to being the real me. Because the hormones softened my skin and facial lines and helped me to grow breasts, hips and hair. Like I said, all of which were the real me just waiting all this time for the changes to happen.

All the dots I connected were in a big circle. I went from a young boy for the first time being amazed at what he saw in the mirror (and wondering what was next), all the way to being able years later to being able to find the real me and live out my goal of crossing the gender border into a transfeminine world. I could not wait to give away all my male clothes; enjoy the new hormones I was on and live a new life. I was even able to take vacations with my third wife Liz to places I had never been before. All as my new self.

I can’t say connecting all my dots was ever fun and at times very scary, but they were always with me as I lived my life. At my advanced age of seventy-six, I am fortunate that I had the chance to find the real me before it was time for me to connect the final dot and step into the next dimension.

 

 

 

 

 

 

 

Tuesday, April 21, 2026

More Changes

 

Image from Brad Starkey 
on UnSplash.

More changes are coming to our house beginning today. Thanks to my wife Liz, we are tearing out one of our old bathtubs and putting in a new walk-in shower. Which is perfect for my immobile status and makes it less dangerous for me to take a shower.

You would think, by this time in my life, I would be used to change but it seems I have just become more set in my ways as a senior citizen transgender woman. As with many of you, our gender issues changed us for the first time quite early in life. Mine manifested itself the first time I felt the magic of trying on my mom’s clothes and I worked my way forward from there.

At that time, I labored under the impression my love for feminine clothes would eventually go away but it was something I ended up growing into rather than away from. The older I got, the more skilled I became at acquiring key items in my wardrobe and hiding them away in places even my younger brother would not find. I even increased the number of odd jobs I would do (such as a newspaper route) to augment my meager allowance and allowed me to buy items such as makeup and panty hose which felt so good on my legs I was shaving earlier than probably half the girls my age that were allowed to do. To shave them I had to use my mom’s electric shaver which I needed to carefully clean after every use. Again, somehow, I managed to escape detection as I continued to cross dress.

It wasn’t until my military days that I really began to push for more changes in how I was approaching my femininity. It was a Halloween party I went to when I only had about eight months left to serve that changed everything. For my “costume” I chose a slutty woman’s look to go with my friends looks. Further down the road, during a night of drinking fine German beer, my “costume” came up in a casual conversation with three of my closest friends, including my first wife. As we talked about the amount of time and effort to look the way I did, I finally thought to hell with it, and told the group I was a transvestite (the term of the day) and I liked to wear women’s clothing. Surprisingly, no one cared and life went on normally for me even after for the first time in my life I risked it all and told someone else my deepest darkest secret. I felt like a huge weight had been taken off my shoulders, but my freedom was fleeting because of what I did in the Army. If anyone of my higher ups had found out about my secret, it could have easily caused me to have be put up for a dishonorable discharge with less than the eight months I had left to go. Which would have been heartbreaking with all the changes the Army had put me through.

As I always write about, my newfound freedom to tell anyone else about my ongoing male to female femininization project came to a screeching halt when I tried to tell my mom. She rejected me totally and sent me scurrying back to my closet as far as telling any blood family about my potential transgender dreams. The only close person to me that I knew was my first wife and surprisingly her sister who told no one. I think sometimes by coming out the way I did at Halloween parties was a plea for the public to listen to me and when I did ever transition, no one would be surprised. Surprisingly, I was so macho in my male life, nobody ever did. Including the few people who were still alive years later when I came out. All I got was surprise from the people I knew. The main reaction was that I seemed too macho to ever be a woman. 

All the changes I went through as a novice transgender woman in my thirties and forties were immense as I learned what I was really facing if I followed my gender path to my ultimate goal of living fulltime as a trans woman. I kept being stopped by blind curves and huge Ohio potholes as I learned the hard way what ciswomen must go through to live their daily lives. I had become a social person later In life and desperately needed it to continue when I went behind the gender curtain and emerged a better person. I spent so many evenings planning to be by myself that the loneliness was really getting to me before changes suddenly began to set in. It all started when a bartender at one of the venues I visited often set me up to meet her lesbian mother to have a casual drink where she worked.

We became friends and were able to see each other often until another woman entered our little group and we became a friendly threesome and gathered to watch sports on the big screens. Of all things, the third woman was another lesbian who slid her phone number down the bar to me one night when I was alone and I responded feeling much better about myself.

The most amazing experience I had was yet to come when my future wife Liz responded to an online ad I placed. Predictably, I had to sort through the ton of online responses I received all the way to being stood up on pre-planned meetings with men I met online who I refused to not meet in public. I met Liz on the other hand in one of the sites where I was advertising in a “woman seeking woman” room and she responded to me and kept responding until we set up our first date midway between our homes which were approximately seventy-five miles apart. We went to a drag show then to a Renaissance Festival and fairly soon she invited me to move in with her. That was over twelve years ago, and I surely made the right decision.

With all this social success, I need to point out again how many dues I needed to pay before I was successful. I look at it as a full circle karma payback to all the lonely times I spent after my second wife died along with most of my closest friends. I had nowhere to turn for comfort and was forced to step out of my usual social conditions to look for connections. But that did lead me right back to the old big sports bars I so enjoyed and felt at home in as a man. Again, a full circle social moment. At least, the bartenders would socialize with me if I did not cause any trouble and tipped well. At that time in my life, any interaction was welcome as I went through the biggest changes in my life.

Change is a natural part of life anyway, but it seems we transgender women and transgender men have more than of our fair share of change to deal with. To be sure it is difficult as we pay our dues to live a life as our authentic selves.

 

 

 

 

 

Thursday, April 16, 2026

We Must Be Better

 

Image from Ecaterina 
on UnSplash


Yesterday I wrote a very short post about going to the doctor with my wife Liz. During the post, I put quite a bit of emphasis on what I was wearing, just to look casual. Following the post, I received a comment from “Dana” exploring her own feelings about presenting in the world convincingly as an older transgender woman. She said (and I paraphrase) we older trans women must be better than the average ciswoman to survive in the world.

Of course, I agreed and took it a step further. Young and old, in no matter what we do, transgender women and transgender men must be better than their cis counterparts in everything they do.

It all started with me when I began to seriously get out of the mirror as a novice crossdresser and into the world. One of the first things I needed to do was upgrade my very limited fashion wardrobe. I found out the hard way; I was too heavy to attempt to find fashionable clothes for larger women like me. Immediately, I went on a diet which melted off nearly fifty pounds of weight. Which made all the difference in the world for my shopping confidence when I haunted the thrift stores for the best clothing bargains I could afford on my still limited budget.

At the same time, I concentrated on taking care of my skin by using cleansers and moisturizers every morning after I shaved. My skin did improve and I could use less makeup for a better overall effect. Through it all, I considered it a labor of love if I was ever going to present better in the world as a trans woman and not be mocked.

Finally, I did make it to a point where I could blend in with the ciswomen around me after learning many brutal lessons which sent me quickly home in tears. I found out the hard way I had to be better, just to be average and blend in with the world which was seemingly out to get me. Probably the main thing I had going for me was how dedicated I was to be staying on the gender path I was following. I always knew it was going to be rough but not as tough as it was turning out. I had a lot of dues yet to pay if I was ever going to make it to my dream of living as a transfeminine person. I thought I knew a significant amount of how women live but I had no idea of the complexity of life I was facing. Which was exactly what my second wife was trying to tell me every time she sensed me drifting away from being a cross-dresser towards starting HRT and living as a transgender woman.

What she did not tell me was, in order for me to make it, not only would I have to be average as the new person I was exploring being, I needed to be better. I was fortunate and stuck to my ideas of exploring the world around me as a trans woman mainly because I little voice in my head kept telling me I was doing the right thing because I felt so natural when I was living it. I emerged from this time in my life with a few scars from the experiences I was going through which healed quickly as I moved on to better things.

In essence, I found I could be better and carve out a new feminine life from scratch. A place where no one knew anything about my old male life and my present seemed to be more positive than my past ever was. In my way though I still had the usual male baggage problems such as an unapproving spouse (whom I did not blame), a family, and a very good job I knew I was going to lose if I did what I knew deep down I would have to do. Jump the male to female gender borders and finally live where I wanted to live from the beginning.

At the same time, I found the more complex my life became as a trans woman, the better I needed to become to protect it. On the girl’s nights out, I was invited to for example, it was key that I never went into my past very far and outed my deeply rooted male past. The example included the time I spent with my lesbian friends who would have not enjoyed any stories I had of my male past if I ever let my guard down and just blurred relevant details of my past. My willpower kept me going until I never thought about my past at all, except that it was a bad dream.

If you are on the fence considering coming out into the world as yourself, just remember to build yourself up to the point where you are the better person as a transgender woman. Perhaps then, you will have reached a place you were never able to find in your old unwanted male life. And key to the whole process is when you are feeling natural as your feminine self. By then, you will know that you have made it to a good place on your gender path. But if you decide not to go any farther, that is OK too. It is your life to live to its fullest, and your journeys into the feminine gender will have taught you so much about the need to be better.

I get asked all the time how I knew about my gender issues, and the simple answer is I always knew and refused to do anything significant about it. I was stuck in my male box from birth, and he was a powerful influence on me until I knew once and for all the only future for me was as a trans woman. Somehow, I just knew the truth about myself and quit fighting it. It was all for the better.

 

 

Monday, April 13, 2026

I Got Scammed

 

Image from Markus Winkler
on UnSplash.

Years ago, I discovered I was scammed when I attempted to climb my gender path towards my dream goal of living completely as a transgender woman.

My first mistake was believing what I saw in the mirror when I was cross-dressed as a girl was a true indication of what I really looked like. The mirror was more than capable of lying to me by telling me I looked attractive, when I really looked like a circus clown in drag. It wasn’t until I began to go out in public as a feminine person, did I find out the brutal truth of how far I still had to go to present well as a novice cross dresser in public. Rather than create attention to the way I looked, I needed to blend in with the average ciswomen around me and just get by.  I was scamming myself to think otherwise.

Sadly. The scamming continued unabated until I woke up to the true world around me. My life was restricted by outdated thoughts I carried through from my still very active male self who thought dressing sexily was the way to go. The only good thing that happened during this part of my life was that I went through my cross-dresser “adolescence” fairly quickly and began to attempt to dress my testosterone poisoned body the best I could to hide my flaws. I was aided by fashion styles back then which favored miniskirts, bare legs, opaque stockings with oversized sweaters. I was even able to continue a version of the fashion basics when I changed into a bohemian style denim mini along with a flowing loose top to hide my oversize male torso. For once, fashion trends were playing in the right direction for me and my scamming decreased from my male self and the public.

At that point, I shifted my emphasis on where I was going when I was learning the world for the first time.  Initially I chose more malls and safe places such as coffee shops and bookstores until I got bored and chose other venues to go to at night when I began to sneak out of the house when my wife was working. At first, I was satisfied with going to a few male gay venues in downtown Dayton, Ohio. Even though I did not like the overall atmosphere of the places, I kept going because I thought they were safe. That was until I was stopped on a sidewalk outside one night by two men looking for a handout and I was lucky I still had a five-dollar bill to give them, so they left me unharmed. I learned a valuable lesson that all ciswomen knew which was to always be careful of your surroundings and I never went back there again unless I had friends with me.

I also felt I was scamming myself and wasting my hard-earned money by going to gay venues at all. Lesbian bars for the most part were fun for me for a number of reasons. Including the attention, I would receive on occasion from a few of the other patrons. Male gay bars however just treated me like any other drag queen which I hated. I even had a hard time being served which drove me away. It was then; I decided to stop being scammed and take my business to straight sports bars where I knew I could enjoy the atmosphere if only I could be accepted.

I was surprised how quickly I was accepted at venues I used to frequent as a man, and I felt comfortable in. The difference in venues was in the straight sports bars, other women wanted to actually talk to me. Which opened up a whole new world of possibly being scammed by ciswomen and their passive aggressive behaviors. I don’t want to recall how many times I went home with claw marks on my back after I assumed another woman’s smile actually meant she was being friendly with me. That scam became old quickly and I learned to be careful in the world in a whole different way.

The biggest scam of all came when I learned I was not a man cross-dressing as a woman, I was a woman cross-dressing as a man to get by in a life she never wanted. If I had only learned that earlier in life how much easier I could have made it on myself. No such luck, as I was destined to be scammed by a world and my male self into thinking I was doing the right thing by fighting hard to keep my manhood. These days, I am older and wiser when it comes to scamming myself and have accepted the transgender truth, I always denied myself.

As I wrote in a recent post, I would not recommend the path I took towards achieving my dream because the world has changed since I did it. Harsh anti-transgender politicians have made it harder to come out in the world as well as making it harder for some of us to exist at all. (Like in my native Ohio). Hopefully though, the younger generations seem to be resistant and blind to the bigotry of their elders and there is hope for the future. That was, none of us will have to worry as much about scamming ourselves or each other about who we truly are. Just people who have been around forever and are trying to live a basic, honest life.

One way or another, the path we have chosen as transgender women and transgender men is much more difficult than the average person next door. And I can add scammers along with stop signs, blind curves and steep hills on our route to finally discover who we are with the opportunity to live it. It just makes it worse when we learn the person who was our main scammer was ourselves.

As always, thanks for joining me in my journey. Any comments, claps or subscriptions are always welcome!



 

Saturday, April 11, 2026

Your Gender Path maybe Different Than Mine

Image from Erik Mclean
on UnSplash. 
 

Even though many of us share similar paths to our dreams of becoming successful transgender women or transgender men, often our paths diverge and we end up going different directions.

Most of us start out on our own without the help
of an understanding sister or mother and must fill out our gender workbooks as we go along. There is no one to tell us what to wear or how to act in our younger years as a cross-dresser. We just know we have conflicting ideas on what we are doing. On one hand, we cannot wait to put on the pretty dresses we found that still fit us, but on the other hand, we felt guilty doing it. It was somehow taking away what was left of our fragile masculinity.

At that point, most of us were willing to sacrifice that masculinity for the intensely intoxicating appeal of looking at ourselves as pretty girls, especially before puberty got ahold of us and testosterone poisoning set in. We all know what happened then, our bodies grew angles instead of the curves we admired on the girls around us and life would never be the same again. From that point forward, many of our paths seem to diverge. Over the years, I have heard from several readers who put down their urges to be feminine with no problems until much later in life. While others followed a more focused stairstep path which meant meeting and learning from other cross-dressers or transgender women searching for their true meaning to life. I know when I first discovered there were others like me who shared gender issues and I could go meet them; there were many layers of people who attended the socials. Anyone from cigar smoking men in dresses still going overboard to preserve their masculinity to completely femininized transsexual women whose next stop was gender surgeries.

It was then that I began to see and appreciate the different layers of the gender community I was seeing in person for the first time. I could almost compare it to the amazing number of cosmetics I saw the first time I went shopping with my own money to buy my own. The entire idea of going to a mixer of my peers did not work for me at all. I became more confused about where I fit in on the gender spectrum than when I started. I knew I was much more than a part-time cross-dresser but was not committed enough to consider complicated and expensive gender realignment surgeries which were still fairly rare back in those days. The direction I decided to take was one of experimentation which I found set me apart from many of the other gender conflicted individuals I had met.

I certainly would not recommend the direction I took because it involved a certain amount of risk and way too much alcohol in the mostly gay venues I initially was going to. What happened was, I used the fake courage of the alcohol to allow me to take ill advised chances in places I should not have been as a single woman. Especially a transgender one. I was fortunate when I escaped unharmed in a couple of situations I should have never found myself in as I was dressed way to provocatively for where I was going and one time in particular found myself having to be bailed out by my second wife who had warned me ahead of time about my mini-dress being way to short. I attracted the unwanted attention of a cross-dresser admirer who was huge and had me trapped in a small hallway with nowhere to go when my wife grew curious and came in time to rescue me. Believe me, it took me a long time to live that incident down with her.

Even when I became a regular in the big public straight sports bars I was going to, I would not recommend my methods of establishing a path to gender freedom as a trans woman. Being a single woman in a public place can sometimes be dangerous to the point where you don’t see many ciswomen do it. They always bring a friend or two for safety which it took me awhile to finally come to the point where I could do it too. My only recommendation is to act like you have a friend coming to join you by acting as if you are talking to them on a cell phone, or “save” a seat next to you with your coat if it is wintertime. Better yet, you can solve the problem completely by sitting at a dining room table, but what fun is that?

Another way to attempt to find companionship is through the use of social media. I tried that too and had to sort through a tremendous amount of trash before I hit the jackpot with the person who turned out to be my third wife Liz. Unbelievably, she contacted me on a social media site which I was listing under woman seeking woman. Better yet, it turned out we were within driving distance of each other and began to correspond until I became brave enough to talk to her on the phone. I was so ashamed of my voice to do it. I finally jumped off the deep end and had success as we started to date. That was over twelve years ago and we married and are going strong I am happy to say.

I see and hear from so many transgender curious people who are on the gender edge in their life with no evident way out. My only recommendation is that at some point you need to take chances if you ever want answers in your life. The only certainty is if you do nothing, nothing will happen. I’m sure I don’t have to tell you that you do have to be careful though with all the scammers out there these days and all the negative people you may encounter if you decide to go public. With the political arena and anti-transgender laws which are being passed in many states such as my native Ohio.

No path is right and who is to say, your path is not right for you even if you decide to stay in your closet which is safe and not risk giving up things such as spouse, family, friends and employment. Maybe you can experiment too as you discover which path is right for you. As I said, be careful of the stop signs and bumps ahead.

 

 

Memorial Day 2026

  Image from Richard Sagredo on UnSplash. It does not seem possible to me, but another Memorial Day has come and gone. A time to remember t...