Showing posts with label gender dysphoria. Show all posts
Showing posts with label gender dysphoria. Show all posts

Thursday, February 19, 2026

What is Chasing You?

 

Image from Filip Mroz
on UnSplash. 

As human beings, we all have something that is chasing us. As transgender women or trans men, that something which is chasing us may be more serious.

As we all know, gender is one of the most basic wants and needs for a person. At birth, we are put into a male or female box which is often very difficult to change. In my case, I was born into a very male dominated family as their first-born son, so changing anything with my gender was totally out of the question. In addition, information on gender dysphoria was difficult to find in the pre-internet days.

All of this set me up for a chase which would dominate my life for nearly five decades. Mainly because my male self-had a huge head start on the race to claim myself. He was born into male privilege that he just had to compete in the world to claim. Along the way, he managed to do quite well in the privilege race, which made it more difficult to give up his male life when the time came to do it.

As I became older and more settled into a routine, what was chasing me became more evident. I wanted to be a transgender woman more than anything else in my life. It all set me off in a collision course with changing jobs and moving from my native Ohio as I desperately tried to outrun what was chasing me. I thought each move I made would bring me closer to living the dream life I always hoped was possible. Examples included moving from a small conservative town in Ohio to the huge metro New York City area so I could be closer to a more liberal cross-dressing area. Even though that proved true to an extent, I found I still had the same restrictions on expressing my feminine self as I had in Ohio. So, I moved back to a very rural area where I thought I could hide my cross-dressing ways. Ironically, the best move I made was the next one when I moved back near to Columbus, Ohio where I could reconnect with the small group of diverse friends I had made before at crossdresser-transgender mixers I had went to.

Through it all, all my running was becoming increasingly exhaustive on my mental health. I was taking one step forward towards my goal of living a transfeminine life, while at the same time taking a step or two back when my public persona as a woman was discovered and I was crushed mentally. I kept going back to my gender drawing board until I got it right, or to the point where I could go out in public without the fear of abuse.

When I did reach that point, the feminine person chasing me upped her game and I needed to get better when I interacted with the world. What happened was people started to recognize me, so I needed to start building a whole new person. I needed to choose a new name to fit my personality and stick with it. Which also meant I needed to attempt the most difficult task of all for me, the time I spent communicating one on one with other women. I needed to throw my innate shyness out of the window and learn the basics of eye-to-eye communication which I learned was so big with cis women. Plus, I really wanted to learn to interact with women because I could learn so much from them while at the same time not coming off like a mean bitch.

As I learned to relax and interact with my new world, the inner female which was chasing me could relax a little too. At the same time, my male self-began to finally realize he was losing the race for dominance in my world. More and more, I felt the fear of giving up my male privileges fade away as the introduction of female privileges set in. For the first time in my life, I felt free of the gender struggles which had defined me. I remember vividly the night I sat by myself and added up all the pluses and minuses to the moves I was considering making. The end result was in my life as a novice transgender woman, I had never felt so natural and free. The decision was an easy one for me as I decided to take the next step and seek a doctor’s approval for gender affirming hormones or HRT. A move I considered for once and for all, end any questions about what was chasing me.

That decision brought all the exhaustive chases to an end in my life. The only problem was it took me until the age of sixty to face my inner truths and find peace in my life.

 

Monday, February 16, 2026

Did I Do It Right

 

JJ Hart

As I slowly made my way through the process of recovering in the hospital from pneumonia, I had a lot of time to think about the gender decisions I had made during my life.

The first time came as I was being checked in in the emergency room, I had a chance to watch the older ambulance driver flirt with the attending nurses in the hospital. As I did, I wondered how it would have been if I had not suffered from any gender dysphoria in my life at all. What sort of a male life could I have lived without all the distractions I had. I also knew as a male, I did my share of flirting with women too.

Then, when I was really feeling sorry for myself as I had to expose my male nakedness to the nurses when they took care of me in bed, I wondered if I had actually taken the measures to have more gender realignment surgeries. Did taking the easy way out come back to haunt me. Because I decided against having any surgeries at all. My gender was always between my ears and not between my legs as I had decided. Plus, I was successfully beginning to build a life as a transgender woman as I was, so why fool with success. Every turn I made on my gender path presented me with an opportunity to face a different challenge, even though most of them terrified me. As I moved forward into a feminine world, my main goal remained just to do it right. Humans rarely get a chance to do their lives over, and I better not screw up my chance at mine.

As I lay in the hospital bed thinking what I would have done differently, the answer came back to me loud and clear. Nothing I could have done different would have helped me except maybe coming out of my gender closet into the world quicker. But even that idea had strings attached because the world back then was a totally different place. In many ways, it was a softer, gentler place for transfeminine people to exist in but in other ways, just as difficult. Perhaps too, it could have been just my perception of the world because the whole process was new to me at the time.

Did I do it right? Who is to say what is right from wrong when it comes to a gender transition. Some have intricate surgeries and some don’t is just the beginning of all the differences in the paths we can take. And surprisingly there is no right or wrong answer. Which is the conclusion I came up to as I laid in my hospital bed awaiting my next challenge to my gender. Thankfully, most of the staff just didn’t seem to care. I was just another face in the crowd to them.

My next challenge is to totally rid myself of all the vestiges of this crummy disease. I am still fighting a bad cough as well as a stopped-up nose, so life could be worse. My blood pressure also has been running too low, so I am monitoring that.

Enough whining, I am happy to be home where I can truly rest. At least I know I did that part right.

 

Saturday, February 7, 2026

Gender Hide and Seek

 

Image from UnSplash

On occasion, I look back at my decades long journey to live as I really wanted to live as a transgender woman as a roller coaster sort of ride, which had its share of major ups and downs. For a time too, I looked at where I was going a something like a drug addicts plunge into despair. When I was sinking deeply into the lost feeling of my gender dysphoria.

What happened was, the pendulum always swung back after I had another satisfying session in front of the mirror admiring the pretty girl I had conjured up in my mind. I became so good at doing the routine in front of the mirror that I could count the days when the pressure built up to a boiling point and I would have to come out of hiding and cross-dress my body again. If I could go back and do it all over again, I would have recognized I was much more than just the average cross dresser, I was trending towards being a transgender woman, way back then. Years before the term trans was even invented and used.

The older I got and had finished my military obligations; I grew more complex on how I played hide and seek with my gender emotions. Particularly, when I began to go out in the public’s eye more and more. In fact, my entire gender focus began to shift from just admiring my self in the mirror, all the way to beginning to forget about my male self all together. It took me years to arrive at the final conclusion my life was leading me to, but I did it. I was never a man crossdressing as a woman; I was a woman doing my best to cross dress as a man and failing miserably at it. Even though I did make small strides towards becoming a man my family could be proud of, my life as a guy just was never enough.

My major problem was I was pulling too much attention away from my male life and I was beginning to not hide it well at all. to live as one of the main binary genders just kept increasing to a point where I could not take it any longer and I tried to punish myself through a series of self-harming events. The hide and seek game I had played so well, began to collapse around me. I felt like the incompetent juggler who kept dropping everything he was trying to juggle and when it did, the pressure increased to a point where my mental health could not take it any longer and I felt the only way out was through a series of severe self-harm events like taking my own life. I guess you could say, the ultimate game of hide and seek when it came to my gender issues.

Looking back, playing a lifetime of hide and seek was no fun when it came to dealing with my gender dysphoria. Knowing for sure which gender I was when I woke up in the morning was a benefit, I never had the chance to appreciate in my life until I was in my sixties. For years though, if I had had the courage to face who I was, I would not have had to play hide and seek at all. It was like I knew what was behind door number one all along and was afraid to choose it.

Now I know why I never liked games at all.

 

 

Wednesday, January 21, 2026

Staying Calm

 

JJ Hart, Cincinnati Pride

Many times, staying calm as you traverse your gender path is easier said than done. For example, take the early days of exploring your mom’s clothes to see what still fit and how well you thought it made you look in the mirror. Just the sight of your girlish self-brought a palpable change to your excitement level that you would never forget. Then the disappointment set in and your calm was shattered when you knew you had taken the last little bit of time you had to take off the makeup and clothes and return to the boring male world you were forced into.

At that point, as you grew up, it became evident that taking the time to cross dress as a girl anytime you could calm you down and made life easier…until the pressure built up and you could cross dress again. In my case, before long, to stay calm in my life, I needed the effort I put into looking like a girl. If I did not, all I would worry about was the next time I could apply makeup and a dress and look at myself in the mirror.

For some reason, when I was young, I thought age would temper my urge to be feminine. Then the internet came along (with social media sites) and I discovered there were others with like interests in femineity. I also learned new terms such as transgender which for the first time, I thought applied to me and the gender dysphoria I was suffering from. The whole on-line process took me out of the printed confines of “Virginia Prince” and her “Transvestia” publication and into a world I could communicate with. Suddenly, my calm was shattered again as I needed to sneak around my wife’s back on our computer to see what I could learn and wonder if I could ever achieve the attractive beauty of some of the cross-dressers I saw. I even discovered a contact relatively close to me that I was conversing with until my wife caught up with me and I needed to stop to retain the uneasy calm we had in the marriage.

As luck or destiny would have it, staying calm became increasingly complex for me. I had started to explore the world as a transfeminine person with some success. So much so that I could not keep my mind off what I was going to do next as a novice trans woman when I went out in public the next time. The pressure to balance a life in two genders was tremendous and the only time I ever remember being calm was when I was out living my new life as a woman. But again, the feeling of calm was fleeting as I had to hurry home and change back to no makeup and skirts to my male work-a-day world and at the same time hiding my true transgender self from my wife and most importantly myself. It took me years and years to understand the true basis to all my jittery problems, I was fighting a male gender the whole time I should have never been born into.

When I gradually began to understand what I was up against as a gender conflicted person, I turned to therapy as a solution. As with anything else in life, I suffered through bad therapists and benefitted from good ones. One of the good ones was the initial gender therapist I went to in Columbus, Ohio when I saw her name in an ad in a LGBTQ newspaper I was reading. The sad part was that in true male form I refused to listen to her advice when she told me there was nothing she could do with me wanting to be a woman and I would have to decide someday what decision I would make. If I had listened to and heeded her advice, I would have been able to build the calmness of choosing my dominant gender long before I did.

The next two therapists I tried were terrible and knew little about gender issues at all, so I kept searching for another good one which I found in all places like the Veterans Administration. She had a great basic knowledge of the LGBTQ community and was willing to help me through my Bi-Polar depression issues also. The luck of the draw, again went in my favor as she even helped me in the legal change documents, I needed to change my gender within the VA and out in the world. During this time, it was difficult to remain calm because of all the positive changes I was going through, and my life was so exciting.

When I really calmed down was when I was approved for HRT or gender affirming hormones. The HRT took off the remnants of my testosterone poisoned personality. Or I should say, took the edge off all my feelings of aggression and panic. Very quickly my whole world softened, and I could see a future again. It was a true calmness of existence that somehow, I had always craved but had no idea how to achieve it. Little did I know, I was on the right path the whole time and did not know it. Worse yet, my path led me to being addicted to stress in pressure packed jobs on top of my gender issues. I just did not know how to be calm and slow down and enjoy the present.

Our lives come at us quickly, so that is my excuse for living mine the way I did. Looking back, I do think I was able to use the basic building blocks of my male life to build a stable future as a transgender woman. I equate it to going back to school and getting credit for courses you already took. Life around you changes but certain basics always stay the same. The best advice I could have had for myself is you only have one life to live. Try to sit back and stay calm so you can enjoy it.

 

Tuesday, January 20, 2026

Her Way or the Highway

 

Image from Joshua Rondeau
on UnSplash. 

Very early on, it became evident to me that my feminine self was very demanding. Who knows, maybe she took after my mom who had to be strong in a very male dominated family.

Wherever it came from, I always felt a strong push from her to be let out into the world to live. Even so she would have to wait years and go through constant trials and tribulations to do it. The gender journey I was on proved to be much longer and challenging than either of her competing souls thought possible. Nearly a half a century of trying before I got it right.

To make matters worse, my male self never was one to give up easily and he fought every move intensely along the way. Making everything even worse was that he was fairly successful in carving out a life he never really wanted as a man. The more baggage he accumulated, the more difficult it became leaving it all behind in a male to female transition situation.

Even more stressful was the fear of the unknown which followed me everywhere. It started with the feelings of not knowing if I was a boy or a girl when I was growing up and continued onward from there. Seeking gender answers always took a lot of energy out of my life that I wished I could get back. Of course, that was impossible and I needed to learn to live with the way I was with my gender dysphoria until I hoped I could do something about it. What I did do was get out of my closet/mirror and began to see what the world would be like for a transgender woman like me. Would it be her way or the highway after all. Following a rough start with my public presentation, I lost nearly fifty pounds of weight and began to perfect my art of makeup. I put a tremendous amount of work into my feminine presentation, more than anything else I had ever done in my life.

As it turned out, all my effort was rewarded and my transfeminine self-began to emerge and live her life. The days of just going out to be alone in the world subsided as I was able to make new social contacts for the first time as a trans woman. For the first time in my life, the gender teeter-totter I was on began to favor my feminine side which proved to be a real problem for my male side who still was working fulltime in the world and bringing home a good income. I was actually ahead of my timetable in how I wanted to work out the gender issues in my life and increasingly it was becoming her way or the highway when it came to my life.

The pressure to change became enormous and wrecked my mental health leading me to alcohol abuse along with self-harm (suicide) attempts. I drove too fast and took too many chances hoping something would come along and put me out of my misery. Nothing ever did until I realized the answer was screaming at me all along. I should have never been born into the male world that I was and now would have to overcome the testosterone poisoned past I had lived to do something about it.

Her way became a real reality to me when my second wife passed away unexpectedly from a massive heart attack at the age of fifty. I was so disappointed that she never did anything about her health until it was too late that I never properly grieved the loss of someone I had been married to for twenty-five years. Instead, I turned to the waiting arms of my feminine self for comfort in my times of severe despair and loneliness. She was all I had as I sleepwalked through my life, and her highway began to look better and better. My new timetable of a possible jump across the gender border dramatically increased when suddenly the greatest barrier to stopping my leap had been taken away.

Before I knew it, the new highway I had dreamed about living on was upon me and it was fast and smooth since I had worked through most all of the bumps and potholes earlier than I had experimented. For once, I was not frustrated with all the time it took me to make my final gender transition decision. I always compared the road I was on to the Autobahns I drove when I was in Germany which were always well maintained and built for high speed. I even had to be careful that I was not going too fast as I had to figure out who was left to talk about my authentic self. My daughter came first, which went exceedingly well and then my brother which went exceedingly bad. Then I moved on to what was left of the very few friends I had left or just began to not see them anymore as I built my new life.

I am very glad now that it was her way or the highway in my life. She kept telling me it was the way life should have always been and the brief moments of life I saw which were so fluid and natural were only the beginning. Maybe I had been too cautious for my own good when I tried to take the back roads towards becoming a full-fledged transgender woman, but it was the only way I knew. Hiding who I was started so early in life, I never saw my way out of it for so many years until it was too late. I was stuck in a habit I could not get out of. Until I woke up to the fact that her way or the highway was a realistic path my life should take. I have enjoyed the highway ever since.

I was more like my mom than she ever knew.

 

Friday, January 9, 2026

If You Dream it, Can you Do It

 

Image from Alaric Duan
on UnSplash.

Dreams can be a motivational tool or a cruel mistake to follow.

Often dreaming it and doing it are two vastly different things. As I always mention, some of the most serious and reoccurring dreams I experienced were those which I was a pretty girl and those dreams carried over into real life with me wanting to be a woman when I became older. For years and years, it seemed to be an impossible dream. As it was impossible to see the future.

Initially, the future just looked bleak to me when my cards told me I would be a male for life. I was born into it, now I had to get over it. I can honestly say I worked hard at being the best man I could. Even to point where I did not appreciate the toxic male behavior, I was witnessing around other males I was with.  I am sure now, I was feeling how my feminine side was reacting to the spectacle I was witnessing. It certainly affected me when I first encountered toxic males when I entered the world as a transgender woman. I was paranoid and considered myself an easy target for them. Still, my dream would not go away, and I continued along my path to gender freedom. Sometimes, my life was like I had climbed a big hill and from the summit I could see my dream life in the distance. If only I could get there and was it just another impossible dream.

In the meantime, I became as good as I could on leading a life which included a heavy dose of male status quo. In other words, I was doing all the right things possible to maintain a proper male life, while at the same time attempting to still see if my dream was a possibility. There were just too many gender variables to ignore. Such as spouse, family, friends and employment. I just had to see if my dream could ever become a reality, and if it could, how would I do it. As I was heavily embedded in the male culture and it seemed as if I was getting deeper in over my head every day. I became so sick and tired of having two people compete for my life and every time I did something as a man, having my woman want to do it too. There was no escape, even on vacation when I was trying to run from myself. All that happened was I would grow frustrated with my situation and ruin the whole vacation with my wife when she kept asking what was wrong. There was no way I could tell her the truth and that I rather be spending my time as a woman.

Until I made it out into the world as a novice transfeminine person, did I begin to see I could indeed have a chance to make it to my ultimate goal of joining the society of cisgender women as much of an equal as I could manage. Or would I be roundly rejected and my dream shattered. Of course, during this time of my life, I needed to really consider what I wanted (or needed) to do. Happily, I discovered there was a place in the world for trans women like me if I approached my dream the right way. I decided to try to slow my life down so I could see the big picture. What the big picture showed me was there indeed was a path to my dream.

One of the biggest lessons I learned was to quit obsessing about worrying so much about my appearance and start concentrating on me the best I could. I had spent years doing appearance and achieved all my goals for presenting as a woman. Then it was time for the me who was waiting for her chance to shine for all those years could come out and not  to be outdone. She did not disappoint and she quickly surpassed what my male self-had attempted to do for all those years and proved she was much more than a dream. She emerged as a real person who had paid her dues. I was not the prettiest girl in the room, but I could be the nicest and let my personality rule.

Because of several fortunate events, I was able to see my dream up close and seize it. I am sure if you asked that kid gazing at a girl in the mirror who was him if he would ever make it to living his dream of living as a woman, he would have said you were crazy. He had no way of knowing all the ups and downs and twists and turns gender dysphoria would take him during his life. If nothing else, it made life interesting and taught me a lot about human nature.

For me, dreaming it was doing it. Mainly because I had no other dreams to sidetrack me. I was very much a live and let live person and let life come to me. Except of course, when it came to my gender issues which took years to overcome.

Being humans, we all have different dreams, and I hope whatever your dream is, that you realize it and make sure it is not a nightmare, Surely, if you do your research, it won’t be and you can live your version of yourself as a transgender woman.

 

 

Tuesday, January 6, 2026

Running...Always Running

 

Image from Filip Mroz 
on UnSplash. 

During my life, I have never thought of myself as a runner of any sort. I have never completed any marathons, or long distance runs anywhere except the Army in basic training when I had to.

In basic, all I really learned about running was to never try to look behind you and see how fast if anyone was gaining on you. Mainly because I was never the fastest person running and I was trying to compete against the clock. Not another person. Lessons which came back and helped me later in life when I set out to battle my gender dysphoria. I would have been so much better off if I had never looked back to see who was chasing me.

For the longest time, I took up too much of my mental universe either worrying about what someone else thought about me or worse yet, feeling extreme jealousy over the way another woman looked. I discovered that I was just wasting my time when I spent too much time or effort on both. Which I was doing. There was no way possible that everyone was going to accept me because no matter what I was doing, there seemed to be to be someone else on my wavelength to tell me something was wrong with what I was doing. And as far as being jealous of the way another ciswoman looked, I discovered later in life that there had not been a woman born yet who did not find some sort of flaw in the way she looked. My job was to do the best I could and work with what I had to present my best transfeminine to the world.

Instead of turning around and wasting time and energy watching who was gaining on me, to succeed I needed to throw all my limited resources towards filling out my gender workbook as fast as possible. If someone did like me because I was a transgender woman, that was their problem not mine.

The main problem I needed to solve about me running from my problems was all the moving and job changes I was putting myself and my family through. Even though all the job interviews and moving around was exhausting, I used the process to run from my inner most feelings…that I wanted to quit being a male and live a feminine life. Behind every job move that I made, there was the ulterior motive of wanting to make my life back then as a cross dresser potentially easier. Ultimately, that is the reason I made moves from places like my conservative hometown in Ohio all the way to New York City where I thought I could find a much more liberal existence.

Finally, I went nearly full circle and landed back in my old hometown, but the difference was this time I would be much closer to Columbus, Ohio where I had contacts in the cross dressing-transgender community. By doing so, I even managed to land a much better job which I had worked for years to get. For once, it seemed I was putting my running life behind me, but I really wasn’t. Not until I finally was able to face myself about my true lifelong issues such as (you guessed it) why I wanted to be a transgender woman. To do so, I still had the usual obstacles in the way such as what was I ever going to do about the twenty year plus marriage I was in and the great job I had worked so hard to get, Stopping all the running I was doing was never going to be easy but I kept painting myself into corners I could not easily escape from when on the occasions I was successful in my feminine presentation led me on to wanting more.

More meant taking an increased number of chances with a male life I should have been satisfied with. All my plans were coming together except for the most important one. Except for the most important one I had been running from my entire life. What was I going to do about my increasingly relevant feminine life. The stress I was under became tremendous. Afterall, I was trying my best to juggle two binary genders at the same time. Lucky or not, I was still able to keep most of my feminine life a secret from most of my acquaintances and I continued on as long as I could before the running had to come to a complete halt.

During my life, I was able to only make and keep a very few male friends and as destiny would have it, they all passed away (along with my wife) in a short span of time. At that point, there was no reason to keep running, so I was able to stop and take the easy way out for a change. I chose going all out into a transfeminine lifestyle and never look back with the help of gender affirming hormones or HRT.

When I stopped all my running and faced the truth, I had been avoiding all along, the feeling I had was euphoric and one I had never experienced before. My next step was not to hold it against myself that I did not stop running much earlier in my life and take the lessons I learned about not looking back in the Army. I never knew what happiness was until I did it.

 

Monday, January 5, 2026

What was Meant to be, Will Be

 

JJ Hart doing Trans Outreach program.

The longer I lived and experienced a feminine based experience, the more I realized my life was turning into what I always expected it to be.

Yesterday, I spoke about the “aha” moment I had when I transitioned from being a serious cross dresser to living as a novice transgender woman. Even though I was scared to death to do it, after the experience was over, I felt so extremely natural I knew my life would never be the same again. In other words, my new life as a trans woman was always meant to be and felt like it. Over the years of thinking about my new life and seeking answers, the only excuse I could find was that my mom had several still births before me and resorted to the new (at the time) DES drug which was prescribed to help problem pregnancies. DES was known to flood the uterus with estrogen to help the birth mother and was “rumored” to be a cause of gender dysphoria in children later in life. But all of that was just a theory.

I was left to be on my own forever wondering why I felt so natural when I tried to cross that gender border into womanhood. As my mind wandered into all the different scenarios I could have been confronted with, nothing was ever placed in concrete. As much as I disliked competing in the male culture, still I was relatively successful in doing it and had managed to carve out a life in a gender I wanted nothing to do with. So, it was not that.

The older I became, and the more experience I forced my way into, the more I felt living in a cisgender women’s world was the place for me. If I could make it happen. First, I needed to get past my appearance paranoia/obsession and open my eyes to what was really going on around me in the world when I was exploring it as a transfeminine person. I was naïve in my gender thinking about women as a whole and tended to put them all up on a pedestal. Which I found out was completely wrong.  Quickly I learned that although women operate on different wave lengths as men, almost all the basics were still there for me to learn. At that point, I had plenty of other “aha” moments when I realized the intricacies of how the two main binary genders operated on a daily basis.

I learned too that there were simply some things I could not do by simply observing the ciswomen around me, I needed to interact with them before they would let their guard down and let me see their true selves. The more immersed I became in their culture, the more I wanted to be and again for the first time in my life I began to feel natural in my own skin and felt like my life was meant to be.

I found I was a quick learner when it came to being a quality trans woman and not a standoffish bitchy one. I learned I could make friends easily with most all other women and the rest did not matter anyhow.  Most of them were evil in their own ways, and I did not need their problems if I was ever going to get where I was trying to be. I had bigger issues to face such as how I could learn to communicate effectively as my new, out, authentic self who I learned could not wait for her chance in the real world. She knew exactly who she wanted to be if she ever got the chance. All of a sudden, I was having fun in my life again and the male to female transition problems I was experiencing began to fade into my past. Even though I carried an immense amount of baggage with me from my male life, I was still able to pick and choose what I always wanted to remember from the male world I came from.

If I paid attention to the knowledge, I had gained from having experience on both sides of the gender border, it gave me a real head start on how to conduct myself around men and women. I even was asked questions from women about how to deal with their man and how he may be feeling and I was very flattered to have tried to help.

As I always bring up, my biggest problem with all of my gender transition was how long it took me to do it. Waiting until the coast was clear and when I was nearly sixty years old took away valuable years of my feminine life which I could have experienced more of the world. If I had it all to do over again, I would have been braver and known the huge gender move I was about to make was always meant to be, so just do it. Pull the bandage off my old male life and get on to the future.

Maybe, if I ever have a tombstone, I can have it engraved with the simple words, “She was always meant to be.”

Monday, December 22, 2025

The Hustle and Bustle of Christmas as a Transgender Woman

 

Image from Clarke Sanders
on UnSplash.

Doing the Christmas shopping shuffle as a transgender woman, often takes a lot of courage and confidence to do it.

Over the past couple of weeks, I have written about my holiday adventures leading up to the big day. From taking a short trip to Clifton Mill to view their extensive, festive lighting display all the way to letting two men load my heavy purchase for me at an Oak furniture store, I stretched the boundaries of what I was used to as a new cross dresser or trans woman in public. After it was all said and done, even though I was terrified most of the time, I was happy I tried it all. I came out of doing the Christmas shuffle with much more confidence in my girl self than I had going into the season.

In fact, as I have written before, Christmas quickly outpaced Halloween as my favorite holiday. Why? There were several factors, such as the length of the season and the creativity I could put into celebrating it. Plus, for once, I was doing good for others by buying gifts for them as I shopped. I positively loved it and wondered where the experience had been most of my life.

If you are a procrastinator and last-minute gift shopper like I was, doing the Christmas shuffle as a transgender woman is ideal for you. As you can get lost in the crowds quite easily and no one pays attention to a single woman out doing her late shopping. Custom made for you to do your shuffle and head back home.

I was fortunate when my second wife left her bookkeeping job and took a managerial position at a large bookstore chain. So, at Christmas, she was very busy and worked many hours. It was easy for me to schedule my hours around hers, so I had plenty of time to get out of the house and do gift shopping. I could obsess on wearing just the right outfit to blend in with a busy world and at the same time, search for just the right gift. Along the way also, I could stop in and grab a bite to eat at a restaurant and again stretch my ability to deal one on one with the world as a transfeminine person. Yet another reason, I came to prefer Christmas over Halloween because I hoped I was not perceived as a man wearing a costume, or worse yet some sort of drag queen.

As the big day approached, the sky was the limit for me. I did my shuffle as much as finances allowed and stockpiled my gifts for my special night where I stayed home with some high-powered eggnog and wrapped my treasures to go under the tree if they would fit. Of course, my wife was close to being a professional gift wrapper and I was just the opposite. But as the eggnog kicked in, I did not care, and besides it was the thought that counted. Right?

Finally, the big day arrived and I was shuffled out. Plus, we had family connections to visit all day on Christmas day. My thoughts for once were in other places than doing my precious shuffle which I had learned so much from. After the day wound down and my wife and I were alone, we opened the final gifts from each other. Which included a gift for my feminine self. I will forever remember a nice fancy fuzzy baby blue sweater she gifted me. It was snug fitting and I filled it out nicely with my new silicone breast forms I received from a cross-dresser acquaintance of mine who was purging. Naturally, that part of our gift giving day was the part of the day which was the most anticipated for me. I was like a little kid, brimming with anticipation.

Every year after the intense transgender Christmas shuffle was over, I had the chance to sit back and reflect on all my experiences and what they meant. Without hesitation, I think the confidence I built up from going out in the world as my trans self was the most important aspect of what happened to me. I learned what it meant to blend in with ciswomen around me and survive better than I ever could before. I also discovered the vast majority of the world did not and does not care about having a transgender person in their midst. The biggest difference is that back then, we did not have a Russian asset in the White House leading his blind, spineless party into demonizing a small portion of the population. Back then, I was merely a curiosity to many people, especially ciswomen.

When my second wife passed away, the need to do the major Christmas shuffle went with her too. The only blood family I had left was a brother and a daughter to worry about at all during the holidays. When I came out to them, I was roundly rejected by my brother and completely accepted by my daughter and her family. So, I broke even and even did better when I considered the relationship, I was able to build up with my daughter, son-in-law and three grandchildren. I won the family coming out shuffle in a big way.

Even still, sometimes I miss the hustle and bustle of doing the transgender Christmas shuffle as over the years, I have gone nearly the entire direction in the other way. It is hard to say what I miss most but it probably having the financial resources to buy basically as many gifts as I could afford might be it.  Maybe it all came from having a guilty conscience from sneaking out of our house to join the world as my authentic true self instead of my old boring male self and breaking the pledge, I gave my wife that I never would.

Whatever the case, I was extremely selfish and was a contradiction when I did it to buy gifts for others. I guess it fit in with the whole contradiction I felt from my deep-set gender dysphoria to begin with. I dealt with it all the best I could, did my Christmas gender shuffle and moved on with my life making the most of it.

 

 

Sunday, December 21, 2025

Earning my Way into the Sandbox of Women

 

Image from Juli
Kosalapova on
UnSplash.

I call being accepted in the feminine world of ciswomen around me, as being able to play in their sandbox.

Getting a chance was similar to living a dream and very difficult for me to do. To begin with, I needed to lose whatever weight I could off of my very male dominate frame and take better care of my skin, so I could use less makeup. I desperately wanted to be pretty but accomplished it as naturally as I could. Motivation to do both came easily for me because I was obsessed with doing something very well in life that I cared so deeply about. Surprising even myself, I was able to shed nearly fifty pounds as well start moisturizing daily after I shaved. Obviously, the weight loss helped more dramatically when I could shop for a better selection of stylish women’s clothes in my new size and the decrease in makeup I needed spoke for itself when I presented better in the world.

Even with those positive results behind me, I was still very naïve and had very little knowledge of what I would have to do to be let in to play in the sandbox by the alpha female gatekeepers. As my second wife was always fond of telling me after major fights, we had that I made a terrible woman. Then she added she was not talking about appearance. Which was good since I had just had situations where I was mistaken for a ciswoman to back me up. Then I was confused, if it was not my feminine appearance holding me back, what was it? What would make me a better woman after all.

From that point on, I set out on a mission to understand what she was telling me but I had a major drawback…I was still living the vast majority of my life as a man and as such, ciswomen would not allow me back behind the gender curtain. For the most part, I was stuck in my part-time cross-dressing ways until I could find a better way out. The sandbox remained a faraway dream.

The main problem remained. My male ego would not easily let me pull down my male defenses to see and learn what really went on in a women’s world which operated quite nicely with or without male influence. For the longest time, he (me) refused to listen to women the best he could to learn what they were really saying when he was stuck playing the game behind the gender border. I felt as if I was in East-Germany behind the Berlin wall of gender. I knew I wanted to escape but did not have the willpower to do it. I was a victim to my newly discovered transgender hopes and dreams. At that point, I still had not realized how far behind my gender dreams being a victim made me and I still felt sorry for myself because of all my gender dysphoric issues.

As I always point out, it was not until I began to experience my version of womanhood in the public’s eye did anything begin to change for me. All the effort I put into my appearance came back to help me get my high heeled foot in the door with other women. Then the real work began when I needed to communicate and interact with them. What happened was many other ciswomen were encountering me on a regular basis in the venues where I always went, so I needed to develop a stable feminine persona to go with my appearance. What would I call myself and what wigs would I wear every time I went out are prime examples of what I am talking about. I was getting to the point where I was staring my forties in the eye and I knew I was not getting any younger and in the back of my mind, I had a sneaking suspicion that I had lived my life all wrong up to this point.

Rather than bemoan all of the mistakes or missed opportunities I had as a male, I needed to face the fact I was wasting my time as a male anyhow because I was always meant to be female. I went home and wrote in my secret diary that I was not a man cross dressing as a woman; I was a woman doing her best to cross dress as a man and build a life on a house of cards.

The realization of my true gender status enabled me to be my real self to the public and ciswomen responded well to my truthful gender identity. Even if they were curious what I was doing in their world and why I wanted to play in their sandbox and work my way into coveted woman only spaces. Finally, I was coming to the point where I could think I achieved my own womanhood, just in a different way than most ciswomen. I was still relevant to the world and should be allowed to play in the sandbox.

Another big lesson I learned was that once I was in the sandbox, I needed to work harder to stay. One slip up back to my old male self, and I would be labeled an impostor and barred from the box. Faced with the task of starting all over again. To the best of my ability, all of my feminine mannerisms, interactions and vocalizations had to be perfect. I was so afraid most of the time until I finally began to relax and have confidence in myself.

The best part about the entire process was I survived to write about it and hopefully to inspire others in this very trying, difficult time to be a transgender woman to make it also. We all have differing yet similar paths to make it to the women’s sandbox. Just don’t expect the process to be all positive and you can make it by hopefully finding ciswomen who knowingly or unknowingly help you along. Those minor claw marks you might receive like I did down my back were just learning marks and helped me along. More than the women scratching me ever knew.

They helped me to earn my way into playing in the women’s sandbox. The claw marks just equated out to the stripes I earned when I was in the Army.

 

 

 

 

Monday, December 15, 2025

More Downs than Ups on the Gender Roller Coaster

 

Image from Pietra K. 
from UnSplash.

The gender rollercoaster of life was very real to me.

That is the reason I attempt to mention all of the ups and downs I have experienced over the years as I battled gender dysphoria. For me, the trip up the coaster was not often worth the trip down as my depression set in. Until I received the proper care for my depression, I would often not want to even get out of bed for days at a time. Of course, I could not do that, and life would have to go on. That life included an increasing interest in cross-dressing. When I was on an upswing, life was better and I thought I was even making strides towards possibly living my future dream of living in and competing with a world of cisgender women. All of which had a very large headstart on me towards possibly achieving their womanhood before I could.

All this turmoil sent me down the rollercoaster of life and right back to where I started from…deeply frustrated. It was not until I began to leave my closet or shell and explore the world, did I begin to experience any relief. In the world, I discovered that not everyone noticed me and it was true what my second wife told me that it was not all about me. I was relieved when I learned that most of the world was just living life on their own terms and outside of few haters, I could live my life too. It was when I discovered that I was able to ride the level part of my dysphoric roller coaster, for a while.  

It never failed that when I started to come off the flat spot of my coaster, I needed to fight my depression again. Nothing I was doing was good enough as a man or a woman. I was so involved in wanting a transfeminine future, I could not maintain a good solid relationship with my long term (25 years) wife. The only things I was doing was keeping my head above water at work as I carved out the beginnings of a new transgender life. While I did all of this, I managed to make myself miserable as well as those around me. If I could not live with myself, how could anyone else, was my main thought pattern as I rode the roller coaster of life. All I knew was, I needed to hang on tightly for the ride ahead.

Of course, you all know I did manage to hang on, or I would not be here writing this today. Many times, it was because deep down inside I had this unmistakable idea of what I was doing was right. I had waited a long time in line to ride this gender rollercoaster, and I was not ever going to give up my spot. Once I came to this conclusion, I was able to stand in line with other ciswomen and not be so intimidated. And they were less intimidated by me and the rollercoaster hit another exhilarating turn as it headed into a tunnel. This time though, coming out of the dark did not mean I was heading into so much depression. Still, I knew I had a lot of work to do before I could reach my goal or dreams of living a fulltime transgender life.

Every time I thought I had finished a ride on the roller coaster, I found I needed to turn right around and get right on. A ciswoman’s life was so much more complicated than I had ever planned for, there were more challenges ahead. I still had key decisions to make concerning how I was going to live my new life. Such as how I was going to support myself and what was I going to do about telling my remaining family and friends that all along I had been living a lie. Last but not least, I would take the major step of seeking out approval to begin HRT or gender affirming hormones.

Amazingly, each time I jumped on the roller coaster, my rides became shorter and less eventful. I had taken the time and effort to set myself up as a regular in certain venues I went to all the time, so I did not have to go out just to be alone. I was always a social animal as a man and now I was too in my new exciting feminine world. Most importantly, I was able to develop a small circle of ciswomen friends who unknowingly boarded the coaster with me. They showed me the final steps I would have to take to get off my lifetime ride permanently. Maybe the best part was they never knew what they did for me. Eventually, what came out of it all was my marriage to my third wife Liz. A lesbian ciswoman who was instrumental in kicking me off my roller coaster permanently.

Even though I was ultimately successful in reaching my transgender dreams, I am not so sure I would recommend how I did it to anyone. I took too many chances and consumed too much alcohol along the way. Often, I used alcohol to give me a false sense of security when I was riding a scary coaster. Those were the days when I had to internalize my emotions and fear and “be a man.”

Finally, and thankfully, the world around me changed and I stepped down off my roller coasters all the way to less intimidating merry go rounds. Even they didn’t last as I decided to leave the gender amusement park altogether. Truthfully, I never got much of anything which was amusing anyway, and on some occasions, bigots and haters even put me into the freak category. Sadly, I never won any prizes for the most rides on a roller coaster or had a chance to reach for the ring on the merry go round. I was at least a survivor. I did not have to be a man at all.

Tuesday, December 2, 2025

For Better or for Worse

 

JJ Hart. 

In this case, for better or for worse should not be totally applied to the state of a transgender person’s marriage. Although, it often is.

In this case, I am talking about what happens when we attempt to break out of our dark, lonely gender closets and enter the world. I write long and often concerning the struggles I had when I first tried to come out of my mirror and appear in front of the public as my authentic feminine self. By doing so, I quickly learned I was in over my head as a novice transgender woman or even a cross-dresser. Even worse, I had my second wife telling me I had no idea of what it was like to really be a woman. Even though I was stubborn and did not totally believe her, I set out to discover what she was trying to tell me. The worse part when I tried to find out more about cisgender women was, I was not prepared to go behind the gender curtain to find out what was going on. In reality, I was years away from having the experiences of knowing what my wife was talking about.

At that time, I was still obsessed with how I made my male to female transition appearance wise. All I need to do is go back through all my old blog posts to see how vain I was about how I looked like a cross-dresser and how it dominated my life. As I focused on every little aspect of my appearance. At first, it was all great fun before I began to focus on a higher goal. Something kept telling me I was going to have to do more than just look like a woman to ever satisfy my gender dysphoria which would not leave me alone. As I wiped the makeup off, I sadly knew my male life awaited me again. I so badly wanted off the gender merry-go-round I was on then get on with my life.

It helped a little bit when I finally came to the conclusion, I was more than a weekend cross-dresser and fit the definition of a transgender woman perfectly. All of a sudden, my life had some sort of a meaning it had been lacking. I began gaining access to cisgender woman spaces I had been denied in the past and I was able to see what my wife was talking about. Or I was paying my dues to achieving womanhood on my terms. The better of for worse began to sneak in when I found all the negatives I would have to learn as a transfeminine person. Primarily when my male privileges were taken away and I lost all my personal security I had taken for granted my entire life. And the easy access I had to just going to the rest room as a man. Going as a woman, was such a different experience I could (and have) written complete blog posts about my experiences.

The better part of all of this was, I did not have to put up with the male drama that most ciswomen go through in their lives. I was a prime example of a terrible male partner for my wives to live with. Time and time again, I tried to not be selfish with my desire to be a woman and have it destroyed our entire relationship. The worse of the better or worse was when I became completely jealous that my wives could live as women and I could not. I just could not help myself. Plus, when I came out fully and transitioned I did it in the company of ciswomen who I was used to and did not ever have to adjust to male drama again. I am now married to a ciswoman lesbian who I have been with happily for over a decade now.

I was fortunate when my best transition plans worked out as well as they did. I love it when a plan comes together and even though it was a blind plan, somehow it still came together. It helped when my feminine inner soul was able to take over and run my life. She had been waiting for years, not so patiently wanting her turn to live. She provided the backbone and comfort I needed to move forward in the latter stages of my male to female gender transition.

What I considered a burden, and the worse part of my life, turned into the best part of my life when I was able to experience my impossible dream of living as a transgender woman.

 

 

 

 

 

 

 

Wednesday, November 26, 2025

My Thanks to You

 

Image from Priscilla Dupreez 
on UnSplash. 

As another Thanksgiving approaches, it is time again to give thanks to all of you.

I know the holidays are a difficult and lonely time for many of us in the transgender community and many of us have reached out to non-blood acquaintances to fill the void we lost from an unapproving family. I make no secret of the problems I faced with my only brother on Thanksgiving over a decade ago.

I was just coming out of my gender dysphoric closet and needed to tell what was left of my family about my desire to live as a woman. It just so happened; my timing was perfect as the holidays were right around the corner. Rather than just show up as my transgender self, I decided to do the right thing and ask my brother and sister-in-law if they still wanted me to come to dinner. I was quite naïve at the time and was riding the high I felt when I received an all-out acceptance from my daughter.

I should have known better when the Thanksgiving door was rudely slammed in my face and I was told it was best not to come. I should have known better that my brother would not stand up for me in the face of strong disapproval from his rightwing Southern Baptist in laws. Pressure was thicker than blood with him and we both went on our separate ways. I have not talked to him since and have not missed the interaction.

As I said, my daughter, along with my future wife Liz stepped up in a major way. Not only was I invited to one family function, but I was also invited to two and I had plenty of turkey to eat.

I hope something like my experience has happened to you. Perhaps in the meantime, you have found non-blood friends to fill the family void you lost from rejection. Sadly, Liz’s dad has passed away and her only brother wants nothing to do with Thanksgiving, so the only dinner we are going to is at my daughter’s mother-in-law's up in Dayton, Ohio. For the first time in many years, her son is supposed to come along so it will make it a family get together.

In many ways, I feel as though I have all you regular visitors to the blog as family also. As you have read along with me, I feel you know more about me than most anyone else. In fact, my daughter set me up with a book writing subscription service so I could write about my life to my family after I am gone. I am at question number eighty-one so far.

I hope in many ways; this beginning of the holiday season brings a festive start for all of you. If you are traveling, be careful and make it safely to your destination.

Once again, thank you for joining me here for my journey no matter where you are.

 

 

 

Tuesday, November 25, 2025

Stopping was Never an Option

 

Image from Josiah Niklas
on UnSplash.

Very early on, during my very confusing crossdressing years, I wondered if I could just stop the madness of wanting to change my gender as I grew older. I did not know at the time that stopping would not be an option.

As I grew older, my desire to be a pretty girl (then a woman) grew with me. The more I cross-dressed in front of the mirror, the better I became at the basics of makeup and whatever fashion I could get my hands on. Plus, the better I became, the more I wanted to do more to improve myself. Increasingly I knew stopping and purging all my feminine clothes was never going to be an option even though I tried and tried. At that point, I tried a clumsy attempt to come out to a couple friends I had but was rudely rejected. I needed to return to internalizing all my feelings of wanting to be a girl if I was to survive in my world. Which was cruel and unusual punishment for me and more importantly, my fragile mental health. I was already stuck in long periods of depression before I was diagnosed as being bi-polar by a therapist I went to as I grew up and away from my parents.

When I did move away to college, I actually lost my desire to cross dress and act like a girl for almost a year. I did not know how to act when stopping all of a sudden became an option.

Of course, before I knew it, my gender dysphoria came creeping back into my life. I then needed to build my wardrobe fashion, undergarments and makeup all from scratch. I vividly remember the trigger object which started it all. My future fiancé for some reason, found a short wig to cover her long straight hair, and tried to surprise me with it. I was not pleased and let her know it. I then set out to get her a wig I liked. Funds were tight as I worked at a small radio station where I went to college, but I managed to scrape together the money to buy a beautiful long blond wig I had seen in the window of a beauty shop in my hometown. Under the guise of buying, it for her, I had really wanted it for myself. As luck would have it, she did not like it, and I was able to “inherit” the wig when we separated years later.

I kept the wig until I joined the Army for my Vietnam War tour of duty and beyond, as I was able to hide it away on the rare occasions, I could use it to “top” off my outfit when I cross-dressed. Even with all the traveling I was doing with “Uncle Sam” I still was able to anchor myself with the belief that stopping my idea of being a woman was not a fairy tale and could still be possible someday.

It wasn’t until I seriously began to explore the public’s perspective of me as a newly minted transgender woman, did the world start to change and I knew nothing that I was trying in my new world was going to change…ever. Even still, ever became a big word for me as I hit a series of roadblocks to become a full-fledged transfeminine person. Just when it seemed I was moving in the right direction, something would come along and temporarily stop me. At that time, through all the roadblocks, I finally realized I could see my dream of living like a woman was certainly not an option and it would be a shame to waste all the time and effort I put into my path.

I also needed to make the final decisions I would need to successfully put my male life behind me. What I would do about supporting myself and coming out to my remaining family became very important decisions. My only child (daughter) made it easy on me because she accepted me totally. While on the other hand I was rejected by my only sibling (brother) and we became estranged. My parents, second wife and most of my friends that mattered had passed away which made my coming out process easier. One way or another, I had decided to go my own way no matter what anyone thought.

If I had realized earlier that stopping my male to female gender transition was never an option, life would have been so much easier for me. I would have been allowed to live the best I could, make all my mistakes earlier and achieve my ultimate dream sooner. Rather than stubbornly hanging on to a male life I was born into but never wanted.

 

 

 

Honesty was Always the Best Policy

  Image from Jon Tyson on  UnSplash.  Very early on in my life, I thought my default mechanism to anyone challenging my masculinity would b...