J.J. 's Condo

Visiting Andy Warhol as a Trans Woman

2026-05-17T10:06:30.492-04:00

The late Candy Darling.

Years ago, The Ohio State University was hosting a huge exhibition of the work of artist “Andy Warhol”.

Since we knew how trans and LGBTQ friendly Warhol’s work was to the community, a small group of my transgender women friends hopped in my SUV and we headed to nearby Columbus, Ohio to check the exhibition out for ourselves.

The first thing I noticed from my friends was that they were all wearing their high heels which had a strong probability of becoming very uncomfortable if we had to walk long distances. Since I knew the campus a little bit, I knew we would, so I chose more comfortable flats for the walk. I was happy I ended up sacrificing fashion for comfort because we ended up having to park a distance away from where the exhibition was being held.

Of course, we expected no push back at all from us being there to see Warhol’s work and especially because of his connection with trans stars “Candy Darling” and “Holly Woodlawn” who was featured in “Lou Reed’s" famous song, “A Walk on the Wildside” which among other things mentioned shaving legs and he becoming a she. So, we felt no apprehension about going and mixing in with the surprisingly large number of families that were there. Of interest, here was what Warhol said about Darling: “Candy didn't want to be a perfect woman—that would be too simple, and besides it would give her away. What she wanted was to be a woman with all the little problems that a woman has to deal with—runs in her stocking, runny mascara, men that left her. She would even ask to borrow Tampaxes, explaining that she had a terrible emergency.”

For the most part, the group of girls I went with behaved themselves and blended in quite nicely with the crowd of people around us except for there is always one who tries to ruin it for the rest of us. I had the misfortune of being on an escalator immediately behind a trans woman I had barely met when all of a sudden, she grabs both sides of the escalator and spreads her legs up in the air and wide apart. I was in shock that she needed to pull off such a low class move with all the kids and families who were around. I guess she wanted to show off her recent genital realignment surgery to the world, but I let her have it. Saying I wanted no part of her exhibitionism.

Other than that, I enjoyed the exhibition immensely as I was able to learn more about Warhol than I ever would have had a chance to do on my own without the support of my transgender women friends.

All too soon, it was time for us to leave but way too early for us to go home. So, we decided to try out a well-known gay venue in Columbus that we had never been to. The place was packed, mainly with gay men, a group of lesbians, and a group of intoxicated cross dressers who I did not know it then would come back negatively to impact my visit with my friends. Since I was driving, I needed to only have a couple of beers and just in case, needed to use the women’s room before we left on the long trip home. As always, I tried to wait for the best opportunity to use “the room” until I got to the door and it said for use by “real women” only. Which I was later able to find out was because of one of the intoxicated cross dressers breaking all the sacred restroom rules in front of a lesbian when she was in there with him. I guess he did not even sit to pee and urinated all over the toilet seat before leaving without washing his hands. It was no surprise the sign was on the door as the drunk ruined the privilege of using the women’s rest room for all of us.

I was rather naïve that day and had never been around any transfeminine people in my life that could not conduct themselves properly in public. But, like any other group there are always a couple rotten apples that spoil it for the rest. I resent them because it makes it harder for the rest of us to live a so-called normal life.

The trip back home from Columbus to Dayton, Ohio was thankfully uneventful as we talked about everything, we saw at the Andy Warhol art exhibition at Ohio State. About how Warhol was so much more than just a soup can modern artist we had heard of and specifically his dealings and support of Candy Darling and other trans women such as Holly Woodlawn. In fact, there were so many exhibits of his writings and interactive learning also that it was almost too much to take in at one time.

As far as the “Flasher” went, I never saw her again as she lived in a rural area north of where I did and worked at a well-known big box store. I hope she was able to mature and put her exhibition days behind her, and I knew the restroom actions by someone or someone’s in the cross-dresser group were not representative of all CDs everywhere. But there are still repercussions when you cross the gender border into someone else’s sacred space. You must take care not to overextend your welcome.

If you ever have the chance to see and visit a Warhol exhibition, be sure to do it. Maybe you will be like me and come away with more of a respect for his work than I ever had before. He certainly represents another era of life which will probably never be seen again. In fact, there is a huge museum dedicated to the pop icon’s work to visit in Pittsburg Pennsylvania if you are close enough to visit it.

Chance versus Choice as a Trans Girl

2026-05-16T09:58:45.865-04:00

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.

When Every day is Day One

2026-05-15T09:46:04.580-04:00

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.

A Trans Girls' WOW is Real

2026-05-14T09:53:29.924-04:00

Image from Raamin Ka
on Unsplash.

One of the many reasons I kept moving towards my dream of living as a fulltime transfeminine person were the “WOW” experiences I was having.

Of course, I was a fan of the gender euphoria I experienced when I cross dressed in front of the mirror as myself for the first time. The downside was the buzz from the euphoria did not last that long and then I was stuck back in the life of my unwanted male self. Deep down I knew there was much more to what I was doing except putting on pantyhose, makeup and a dress. I just was not ready yet to face my truth in life.

As I got older and more experienced in being a cross-dresser, I began to separate the gender euphoria episodes with the WOW times I had on very rare occasions. I suppose the reason was that I felt the euphoria so much deeper in my soul that I was doing the right thing with my life. It was then, that I began to seek out a term which described my life to me and it just happened to co-inside with the new use of the transgender word. When I first read about it on our new computer, I thought WOW that is me and I finally made a discovery I could really use to feel like I was not alone.

This new thought pattern led me into the belief that I was no longer a man dressed as a woman when I left the house, I was a trans woman of my own experiences capped off by the TGIF Friday’s experience when I gathered the courage to go out one night and mingle with a group of ciswomen just getting off of work at a nearby mall. It turned out to be a first of a kind WOW experience as I was treated fairly and even managed to put my fear aside and stay for a second drink when I pondered the fact that my life would never be quite the same again.

As I followed up on my Friday’s experience, my emphasis began to be on increasing my visibility out of the gay venues and into the straight ones. I WOW ed myself when I was able to be accepted as fast as I was in most of the liberal places I chose to try. Such as sports bars where I could enjoy a large beer and follow my favorite teams. No longer as a man but as a transgender woman when everybody of any worth left me alone. The WOW was real when I followed my basics of never causing any problems, being friendly to the staff and tipping well. It worked for me nearly every time except when I slipped up and tried to go to a couple redneck venues just to see if I could.

I think then, my WOW’s slowed down as I needed to slow down my advance into the world of ciswomen because of negative pushbacks from my male self and my wife. Both of whom did not want to see me as a woman of any type. My male self because he did not want to lose any of the male privilege, he worked so hard to build up, and my wife because she did not want to lose her husband. Both were quality opponents and put up very big fights. At the time, my inner female simply retreated and waited for her chance to live as part of my overall dream. She had temporarily lost the battle but eventually would win the war.

In order to win the war, my feminine self-had to continue to have the courage to carve out a totally new life as a trans woman in the straight venues I mentioned. I had WOW moments when I was even able to communicate effectively with men who were not intimidated by a woman who had left the men’s club. The whole process just helped me to be a better, more rounded person. I figured if I was starting from scratch again in life, I better do my best to do it the right way.

I must have been successful, because I was able (with a little help from destiny) to start a new complete life as a transfeminine person. My biggest WOW I always mention was the small group of diverse women friends I was able to fit into. Most were lesbians but some were not and even one was transgender. The best part was that I was beginning to enjoy my new life immensely and was starting to fit right in as I build in layers of living between the new feminine me and my old male self no one ever knew. Mostly from going to artists’ and writers’ meetups in Cincinnati as a total stranger and sharing my ideas of writing a blog. It all helped me to establish myself as me and help do away with the remaining shyness I had from meeting strangers.

The only real negative I had was a chance meeting with a drunk lesbian bigot who wanted to know my “real” name. The more I attempted to ignore her, the more she would not leave me alone until my future wife Liz came back and ran her off. The whole negative experience happened years ago at a lesbian Valentine’s dance in Cincinnati, but I remember her obvious dislike for me to this day. Certainly, a negative WOW since my relationship with the lesbian community had always been so positive.

As you can tell, my WOW experiences always came from me stepping out of my male gender box and trying new things. Some successful, some not but if I did not try, I would have never known how bright my future could be. My lesson to all of you is to be careful as you follow your own gender journeys, the world is a changing place for all of us and finding our niche is becoming harder. Hopefully, you can stay the course and be successful.

Who You Going to Call as a Trans Girl

2026-05-13T10:03:45.578-04:00

My friend Raquel

One of my biggest problems when I decided to test the world as a new cross-dresser or transgender woman was having no one to ask about my issues. For example, why was I getting “clocked” or read every time I left the mirror and went to the mall. It turned out that the issue was just tied into how I was dressing my male contoured body by not doing my best to blend in. Ciswomen everywhere were laughing at me from my cross-dressing mistakes and ruining my all-important confidence.

As I said, I had absolutely no one to go to, to discuss the problems I was having in the world. I had no mom to try to rein me in in my trans-teen years or a peer group of girls my age for me to copy. As it was when I was mom’s phantom daughter, I ended up wearing makeup and shaving my legs before most of the girls my age were allowed to do it. Mom, for some reason, never looked for the tell-tale signs of being a curious girl from her oldest son.

Skipping ahead quite a bit, my closet was truly dark in the years before the internet when all there was, was Virginia Prince and “Transvestia” or the “Tri-Ess” social mixers I used to attend every time I could. My hope was that I could find a friend or acquaintance that I could get to know to understand our unique gender issues, but it never worked out that way and I still did not have anyone to call with my cross-dressing problems. The only thing I walked away with was I came away with being more confused than ever before. I did not know how many layers of individuals I would be able to meet at the social mixers I was able to attend. Many more levels than the publications I was reading from “Virginia” led me to believe that existed when she was calling her group as one for heterosexual men only. She probably needed to turn a blind eye and ignore all the activity going on beyond the hotel room doors where the mixers were being held. There was most likely different kinds of mixing than Virginia and the “Tri-Ess” groups would have approved of.

All sexuality aside, there was a diverse group of people who attended, all the way from men in dresses with cigars and cowboy hats trying to hide their femininity to the ultra-feminine “A” listers who were on their way to gender alignment surgeries. Neither of which did I fit in with. I was somewhere in between once again with no one to call or hang out with and exchange trans-girl talk.

It turned out, I only made one significant trans friend and that was Raquel before she moved away from our native Ohio to Dallas, Texas. Even if we were on slightly differing transition paths, we still had enough in common to get along and socialize. She was headed towards gender operations and attracting men while I was on the path of staying the same physically and hanging out with lesbian women. Opposites do attract too in the world of transgender women when we keep an open mind about who is on the right path. The whole situation with Raquel briefly gave me a person to call, and I truly appreciated it even though we have not seen each other in person for years as she is still in Dallas and I am with my wife Liz in Cincinnati.

As I bring up Liz and other ciswomen who were instrumental in bringing out my best as a transwoman, my interactions with them brought on an entirely different dynamic. It was not as if I was calling them for advice on my male to female femininization project, they were always there if I needed them. I was still embarking on an intense learning project as I crossed the gender border for the first time. So, I needed their input like how my lesbian friend Kim handled a man harassing her in a sports bar about her “Pittsburgh Steelers” leather jacket. I did not have to call her for her knowledge; it was right there for my taking. Learning is always easier if you are having fun, and I was having a blast.

We transgender women (no matter where you are on your path) begin our lives as adults on the outside looking into to the world of ciswomen we so completely want to be a part of. In my life I went full circle of having my first fiancé dress me head to toe as a woman when I took the time and effort to call her. She ended up holding it against me for the rest of the time we were together and worse yet, I was not that impressed with her makeup job anyhow. In my circle, she was actually the only ciswoman I sought out for help. The rest, I learned the art of femininity by osmosis or by just observing everything my friends were doing and thinking I could do it too.

The main big problem comes when our frail confidence is shattered when someone says we can’t succeed and major setbacks occur. Unless you are fortunate enough to have an understanding spouse or friend to help you through the rough patches, it still is hard to find someone to call. My suggestion at that point is to seek out help from a local LGBTQ group you can interact with. In person or even virtually until you can regain your confidence about your authentic transfeminine self. Where there is a will, there is a way out of the darkest gender closet.

When you do, maybe you can reach the best step ever and be able to pay forward your confidence in life to help others in need. Which is my main goal for writing this blog. I don’t want to see anyone suffering needlessly in their dark closet.

Success is no Accident in the Trans World

2026-05-12T10:25:33.803-04:00

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.

The First Time

2026-05-11T10:12:40.188-04:00

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.

Mother's Day and the Battle for Gender Supremacy

2026-05-10T10:25:55.419-04:00

Image from Daiga Elaby
on UnSplash.

Before I get started on today’s post, I would like to mention Mother’s Day, and all it means to me. First of all, it gives me the chance to remember all the problems my mom went through to have me. Such as, going through three still born babies before my parents kept trying and had me. Without their determination, I would not be here today. Which is the main reason why I adopted my mom’s first name as my legal name when I changed it years ago.

Plus, even though my mom and I were much alike and fought quite a bit through my youth, I managed to use her as a roll model as I slowly grew into the daughter, she never accepted having. I view her now as a one of kind woman who presented herself to me as an unknowing roll model. Happy Mother’s Day to all of you reading today who may be ciswomen and birthed your own children! We all know how important you are to the world. If your mom is still around, do your best to try to bridge the gender gap. Although I was never able to do it with mine before she passed away years ago.

Now, on to the post for today which has to do with my remaining male gender and how he got in the way of my transfeminine progress in life. I already mentioned the fights I had with my mom as she taught me to fight like she did. Bring anything you could think of to make sure you have at least a decent chance of winning the battle you were in. I think she indirectly taught me valuable lessons about fighting as a girl because I had to resort to being mental and not physical with my fighting.

As it turned out, just the aspect of having fights with other males never materialized much with me as I was growing up. I tried to hide behind liking sports and cars to hide my true love of fashion and makeup to keep the bullies away and for the most part it worked. It also worked when I failed at trying something such as sports, getting beat, and having the chance to run home and soothe my feelings behind one of my favorite dresses and makeup.

This plan was all well and good when I was just dealing with just minor athletic events and became much more serious when it came to activities such as work and life in general. I quickly learned that if I was to be successful, I could not just take my feelings home and cross-dress, I needed to stay there and fight. I needed to push hard to keep my transgender issues at bay and take care of myself. Even though in the background, my feminine self was always waiting to get out and thrive in the world. Sort of like that app on your computer which is always running in the background. Because every situation I faced, I secretly wondered how I would face it as a trans woman. At that point, I needed to face the real possibility that I would just have to experiment with new situations in life from the view that ciswomen do.

That was when I got out of the gay venues I was going to and back into the straight venues I had grown used to going to as a man. Of course, I found the entire process to be extremely terrifying yet natural as I settled down into my new world. A world where I did not have to worry about what my feminine instincts were telling me as I was actively acting upon them. I was free and gender for once was not getting in my way. All I had to worry about was my fear of discovery disrupting my new life.

To my surprise, most of the world around me did not seem to care there was a novice trans woman around them. No one screamed “Hey! That’s a man” when I entered the room and at the worse all I received in response was a few stares. Mostly from women. When I did, I always made sure to stand up straight and try to make eye contact if a could as if to say what is wrong with you? There is nothing wrong with me. As we all know, humans are like sharks in the water who are attracted to blood. When I showed the hard-earned confidence, I gained to project my authentic feminine self, the sharks left me alone. I can’t emphasize enough though the bumps and bruises I took to my ego to find the much-needed confidence to get by.

I did get by and stopped most all my gender battles which helped me to end all the self-destructive behavior I had carried around with me for decades. It certainly took a while for all the emotional scarring to go away and for me to clean up my act. As I always say, it was like a huge weight was lifted off my shoulders when I finally gave in to the transfeminine person I always was meant to be. And I was allowed to continue to fill out my gender workbook as I was socialized in the world of ciswomen by the small group of women friends, I had built around me. I was able to learn a little or a lot from all of them except for one. Which was my biggest issue…

In other words, the biggest boulder on my path to move was getting my male gender out of the way. He was stubborn and hung on to his male privileges as long as he could. All to no avail. I finally had to give up on trying to use all my old male strength to help me and resorted to a more feminine approach of slowly chipping away at portions of the rock. Success led to more success and before I knew it, I had a new exciting path to my future open for me ahead. It was bright, exciting and I never wanted to even think about going back.

Graduation Season

2026-05-09T09:55:19.598-04:00

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!

Working Smarter not Harder as a Trans Girl

2026-05-08T10:04:29.200-04:00

Image from Erik Mclean
on UnSplash.

Before we get started on today’s post, here is a little background on my annual visit to the endocrinologist yesterday at the Veteran’s Administration in Dayton, Ohio.

It turns out, I was just wasting a lot of mental time and effort as I was worried about this appointment. I was worried that she would not renew my Estradiol prescription for the next year. But she did with no questions asked. The only other real problem I asked was why my Estradiol blood levels dropped as much as they did on my last visit to the vampires to have them checked. She did not know and thought I should have them checked again and see where they checked out. So, that is where we left it.

In the same vein, I had a great question from reader “Morgan” asking me if I could sense any differences in my moods when my levels went down since we both are older and on the hormonal patches. I told her no, I did not see any difference except in a new infuriating amount of hair I needed to get rid of on my arms. Since that time, the hair seems to be retreating, so hopefully that signals my levels returned to where they usually were. And, as far as moods go, normally I do feel an overall sense of wellness on the days I change my patches as well as a welcome swelling of my breasts. I hope that covers the question Morgan, and thanks for asking.

As far as the deeper problem of feeling so much paranoia that I felt before the appointment, I think it goes back to my entire progression on the gender path I took to my transfeminine womanhood. It always seemed I was working harder not smarter as I attempted to fill out my feminine gender workbook as fast as I could. It was because I did not have the benefit all the other girls had growing up in a world of ciswomen where I was excluded. Every gender stop sign that I faced deepened my paranoia that I could ever have a chance of making it to my dream goal of crossing the male to female gender border and settling in as a successful transgender woman.

The first part I faced was just working to blend in with the ciswomen public I was around. I wanted to live the old saying that if it walked like a duck and looked like a duck, then it was a duck. My problem was even when I thought my clothes and makeup were on point and looked good, here I was walking like a circus clown in drag in my high heels. Putting my transfeminine persona into motion presented a real problem for me. It seemed like it was not so long ago that I was having the problem learning how to walk like a man out of puberty so I would not be called a sissy by the bullies and here I was trying to reverse the process. It took me a while to try to perfect my version of a woman’s unique style of movement but with a lot of practice I calmed my paranoia when I entered a room full of strangers and did the best I could. Then, I needed to work smarter, not harder trying to remember which gender I was on which day I was presenting. I worked in a pressure packed male dominated industry and it was as if the clock had been turned back and I was worried about being called a sissy again.

Another problem I was having was keeping my mind on whatever gender I was. An example would be all the time I wasted at work wondering what it would be like to live the life the ciswomen around me were living. Or better yet, daydreaming of the next time I could try when I could flip the switch and sneak out of the house again as a convincing transgender woman. If I could reclaim just a portion of the time I wasted, I worked harder not smarter as a person caught between two genders, what a relaxing, extra successful life I could have led. I was stubborn though and persisted through the decades just getting by thinking I could juggle being a parttime woman and a parttime man. Finally, it all became too much for me to handle mentally, so I needed to make a choice. But even then, I had to make certain that I was making the right decision, so I set out to change my path into a more challenging direction.

What I did was to throw caution to the wind and try to experience situations I always wondered what it would be like if I was an actual ciswoman. To do so, I had to finally earn my way behind the gender curtain and really attempt what my own unique path to trans womanhood really required of me. Essentially, the whole process required total commitment from me, and I needed to start making future decisions which would dramatically change the rest of my life. I was nearing sixty and my transgender biological clock was ticking loudly in my mind. If I was ever going to make my move to live fulltime as a woman, I better do it and it was time.

Better yet, I had a circle of women friends to help me socialize into the feminine community and I set out to secure a doctor’s approval to start HRT or gender affirming hormones. The timing was all right for my big move, and I no longer had to work harder more than smarter to do it. Most importantly, my paranoia about doing it all was at an all time low as for a change, destiny was on my side. Against all odds, I was able to meet a stable loving woman online as well as my daughter came on to accept me when I told her my deepest secret about wanting to be a woman my entire life.

Karma was coming around to pay me back for all the paranoia I experienced when I was working harder more than smarter. For the first time in my life, I allowed myself to be happy.

Endocrinologist Visit Today

2026-05-07T09:20:43.039-04:00

JJ Hart at a recent
Cincinnati Pride. Ohio River
in background.

Just a shorter post because my endocrinologist annual visit is today.

The only paranoia I have is that for some reason, she will not renew my HRT medications for Estradiol and Spironolactone. You may ask why I would have any nervous energy before my virtual appointment, and it is because I am part of the Veterans Administration health care system which is always making changes.

Recently, I had another one of my medical providers “retire” and I needed to switch my care from the Dayton VA to the Cincinnati VA which is closer to me. Fortunately, I was able to make it a seamless switch and even was able to visit my local VA clinic for my initial appointment with my new therapist, which I really liked. But all of that had to do with my mental health medications which the VA puts a higher priority on than prescribing medications which have made my gender transition possible. In fact, it was not so long ago that the orange felon in Washington DC assigned a new VA commissioner who was making threatening suggestions about doing away with gender affirming therapy in the VA altogether.

To my knowledge, nothing ever really became of that statement and the rank-and-file VA employees found ways of getting around it.

Another paranoia I have is my “Endo” in Dayton is being retired too and I will have to seek out new assistance in Cincinnati which in itself is not a bad thing except when it comes to where I must go for appointments. Going to the main VA hospital downtown is always a congested mess and I always must ask Liz to take me because of my mobility issues. If I can just go to my local clinic or have a virtual appointment, there are usually no problems.

My current “endo” usually prescribes me a years’ worth of medications unless there are any changes in my Estradiol blood levels. For some reason, after years of staying the same, my levels went down quite a bit on my last test. Which is the last thing I wanted to happen. So I will have to see what she says about it because I am still undecided on switching from patches to injections at my age.

Most importantly, I am who I am, and my HRT does not define me but it surely has helped. I will never forget all the extreme gender changes my new hormones put me through and would hate to lose all I gained. Who knows, maybe I am just building bridges to climb when I don’t have to with this upcoming appointment. She will maintain the long-term stability and status quo we have built up over the years, and our annual visits will continue.

One way or another, I will let you know.

Life is Too Short to be Ordinary.

2026-05-06T10:33:08.510-04:00

Image from Frolicsome Fairy
on UnSplash.

I saw this quote on a television show I watch regularly and it resonated as a transgender woman with me. Here is the quote: “Life is too short to be ordinary.” I immediately thought that a trans woman’s or trans man’s life is anything but ordinary in the world we live in today.

I also thought of a few of the final battles I had with myself before I finally gave in to my feminine desires at the age of sixty and decided to try to enter the transfeminine world permanently. It was never a move I took lightly, which was probably one of the reasons it took me so long to make my final choice to join the girls’ club and leave the good old boys’ club behind.

What I attempted to do was weigh all the good and bad I had accomplished in my long life and use it to make my decision. To be fair, I did have many male experiences which I felt I needed to take into consideration as positives I would have to leave behind if I proceeded with my male to female feminization efforts. The end result was I found that I did not live an ordinary life for several reasons, and one of them was because I spent so much time on the gender path I obsessed about. The others involved just the ordinary life’s challenges that everyone goes through such as maintaining a family, a marriage and trying to be successful in a profession you can tolerate. I kept coming back to my gender issues which set me apart from the great majority of the world, in a good way.

Along the way, I had come to appreciate the difference between the two main binary genders by actually having the chance to live them. It occurred to me that I was having a chance very few humans have the chance to do and I should make the best of it and keep going. At the time, I was spending approximately half of my time in the world as a transgender woman anyhow, so the jump to going fulltime was becoming less and less intimidating to me.

One of the main final factors I needed to consider was how natural I felt living in each gender I was trying to maintain. After hours of thought and contemplation, I came to the realization I had never felt natural as a man. I had to struggle to make any long-lasting friends and it seemed all my accomplishments were for my public persona only. As I always say, I was never a man cross-dressing as a woman. I was a woman cross dressing as a man. From that, I realized I had always felt more comfortable as a feminine person and time was running short for me to grasp the opportunity to change for good. I was sixty at the time and it did not take a genius to realize I had lived more years than I still had to go on this earth.

Finally, it struck my stubborn head that I had been blessed to live everything but an ordinary life and I should follow my natural inclination to stay in a feminine mode. When I did, it was as if I was allowed to take a ton of rocks from my shoulders. As I assumed the life I always should have lived, I began the finishing touches of my new existence by being approved for HRT or gender affirming hormones by a doctor I read about in a local LGBTQ newspaper I saw. My body’s reaction was simple and to the point and I could hear it saying what took you so long as the changes from the hormones were so natural and immediate. In fact, the changes came so fast that I needed to move up my timeline for when I would transition completely away from my old male self.

It does not seem possible that all those gender changes were over fifteen years ago now and my world changed as positively as I ever hoped that it would. The path I took was completely personal and had its share of stop signs and blind curves but somehow, I made it. Probably because my inner self felt it was the only way to go. If working from a male background to being a transfeminine person was the way my path took me, I would gladly go along for the ride. The ride turned out to be uniquely interesting along with being extremely scary when I gave up and lost all my male privilege before I learned the essence of having female privileges.

I was fortunate that I was blessed with a healthy long life. Long enough to see the circle come around from gender darkness to light. So, you could say, my life was long enough to make it interesting and look around all those steep walls and blind curves to see what was on the other side waiting for me.

If the world would let it be, gender is just a human need on a spectrum like so many others and trans people are just trying to live their lives like so many others. And I know gender is much more than a black and white reality to all of us. You can view yourself anywhere from a weekend cross-dresser all the way to a post-op woman and all should be accepted under our complex umbrella of people. It’s just another way we are far from ordinary and difficult for the average person to understand. It is also difficult to explain to a loved one when we do not fully understand what is going on ourselves, which often takes a long time to happen.

Rest assured that even if your life may be different and/or difficult at times, I will be far from ordinary.

Thank you all for your comments, claps and new subscriptions! Without all of you, none of what I try to pass along would be worth it.

Courage or Something Else?

2026-05-05T09:42:54.605-04:00

Image from Miquel Bruna
on UnSplash.

Recently, I have exchanged a few comments with a reader named “Janie” and we somehow got into the subject of being courageous in our male to female gender transitions. Also, on occasion, I get someone calling me courageous on how I decided to follow my path to leading a transfeminine life.

The problem is I never considered myself courageous as I tried and tried to establish myself where I could blend in, in a world of ciswomen everywhere. Here are two examples, the first coming from “Janie.” When she said she wished she had the courage (and I am paraphrasing) to come out as a full-fledged transgender woman as a teenager. On the other hand, I wished I would have had the courage to follow my instincts and come out of my closet when I was honorably discharged from the Army and had very little male baggage to think about. I was still becoming established in the working world, had no children yet and a future wife who did not seem to care what I did. I would never again have that sort of opportunity to live a life as my authentic self without waiting on the world to catch up.

It turned out that I still had a lot of living to do before I could find my way up my path to being a fulfilled transgender woman. Sure, there were plenty of opportunities to overcome when I was petrified to try to overcome my male self and enter the world of women, but I never thought I needed an extraordinary amount of courage to do it. I always reserved that amount of praise for war heroes and first responders who ran towards danger, not away from it. I was not running towards danger; I was just doing what I had to do to survive.

Ironically, the world evolved around me when it came to gender issues over the years. You may remember when the film “Tootsie” came out and gave a realistic idea of what ciswomen go through in the world through the ideas of a man (Dustin Hoffman) living the experience. Sadly, the new look into the genders did not last until today when coming out into the world possibly did take a lot of courage after all. Lives could be wrecked when you would not be fully accepted as a trans woman with your spouse, your family, your friends and your employment. Especially today when the orange Russian asset in Washington DC is leading the charge against us for no real reason.

Getting back to the task at hand, the something else when it came to the courage question, as I said, came down to pure survival. Not some sort of a hobby of putting on a dress and makeup to attempt to look good as a woman. The problem was that I knew at a very early age just looking at my girlish image in the mirror was never going to be enough to satisfy my gender desires. I simply wanted more. To live like the girls around me I so envied in school. An idea which would come back to heavily influence my life in later years. I fought my feminine instincts hard, which ended up doing nothing more than potentially destroying my mental health and my life as I led a very self-destructive life. It seemed everything my male self-had built up, I needed to try to tear down. I would not have wished what I went through on my worst enemy. So, I set out to do what I could to save myself.

During those days of discovery, I learned firsthand the idea of having persistence over any idea of having courage. Survival became my goal in life as I set out to build a feminine lifestyle from scratch. Deep-down, the idea kept coming to me that I was doing the right thing, no matter how painful it might turn out to be. In fact, I went all the way back to my childhood, so I knew it was more than just a temporary rush of gender euphoria as a trans woman when I was accepted in the world. I was surviving as me with little or no courage needed. Just a liberal amount of fear on the occasions when things were not going so well like when I had the police called on me for using the restroom of my choice. It was my own fault for being in a redneck venue I had not taken the time to set up being a regular yet. Then I never had the courage to go back.

I will never try to speak for “Janie” or anyone else who regularly reads my work, but on my end, no matter how much I did not respect the work my male self-did for me over the years there are certain things I would have really missed if I had followed my instincts and come out before I had the chance to build any sort of a life. I would have missed the once in a lifetime opportunity to have a wonderful daughter and a loving wife which I was with for twenty-five years until her untimely death. We had many good times, interwoven with the bad caused by my gender issues. I don’t know if I would have ever had the courage to ever totally leave her and wished she could have been around to experience my growth into a mature transgender woman. Of course, now, I will never find out.

As you can tell, I really don’t believe courage had that much to do with my development as a transfeminine person. On the other hand, a heavy dose of persistence mixed in with the ultimate need to survive allowed me to make it to where I am today. I know I am basically just dealing with semantics anyhow so the only thing that matters is how you survive. With or without HRT or any gender surgeries or with extensive work it does not matter as long as you are happy and thriving.

Thanks to “Janie”, Christine and all of you who have taken the time to comment on my topics. Without all your input, my work would not be worth it.

Pressure Tested as a Trans Woman

2026-05-04T09:38:51.770-04:00

Image from Jayson Hendrickson
on UnSplash.

As I moved along in life, I became pressure tested on both sides of the gender border.

On the male side, I became embroiled with restaurant jobs which involved immense amounts of pressure to succeed and on my female side, I felt the same pressure to succeed when I was finally able to leave my mirror and enter the world. For the most part succeeding as a male meant more financial rewards, while the success as a transfeminine person meant more inner freedom to express myself.

Ironically, my success as a novice cross-dresser or transgender woman often came at the expense of my male self when he failed at a project in life and came running back to dresses and makeup for comfort. Even that became old though when my trans woman kept increasing the stakes in the basic battle to just be seen in public. She wanted more than the easy trips to women’s clothing stores where money was more important than gender. As she began to interact more completely in the world, the pressure to be tested time and time again increased dramatically. Especially when she had to do more than try to communicate with more than a simple “Hello” or “Thank You.” For the longest time, I was panicked and very insecure about holding any sort of a conversation with another person, woman or man.

The way I relieved the pressure of communication was simply tied to doing it over and over again until it became as natural to me as possible. I learned from my feminine vocal lessons, it was not as much about what you were saying as how you were saying it. And how I could interject little feminine vocal patterns into my speech, even though I still had a deeper voice than most women. I say most women because I immediately began to notice a few ciswomen who had lower voices but still managed to communicate in the world with no problems. All because they had the benefit of growing up around other women. As I said, the only way around my communication potential problem was to hitch up my big girl panties and begin to communicate with the world. Which in some cases was one of the last frontiers I needed to face as I climbed out of my mirror and into the world as a trans woman.

I discovered I did not really know any pressure on my initial excursions as a feminine person until the time came to use the restroom. Initially, I was very intimidated and made sure I waited until “the room” was empty before I snuck in to use it until I began to build some confidence in myself. When I did, I began to learn restroom basics such as making sure I took the time to smile and interact with any other women I may encounter. The exact opposite than what I was used to in any men’s room I used. Since I was not using the women’s room as any sort of a fun test just to prove I could, I needed to learn as much as I could about other women because of a natural need to do so. I did things such as trying to mimic the sound of “flow” when I went to the woman close in the stall next to me and of course, I needed to remember to look for toilet paper, hang my purse up and always, always stop to wash my hands as I examined my hair and makeup in the mirror. No matter how much of a hurry I was to get out of there.

Surviving the restroom wars gave me the confidence to lose some of the pressure I felt as I entered the world for the first time as a transgender woman. From there I could move on to bigger and better things such as being recognized as a regular in the selected venues I wanted to go to. When I did, I knew I would have the backing of the staff if and when I was approached by a gender bigot or TERF (ciswoman bigot) about what I was doing there at all. In fact, I think I became the token trans woman at several venues who were proud of their diversity and safely for the LGBTQ community.

If I was a more intelligent person in math, maybe I could come up with a quotient relating to how pressure relates to confidence, but I cannot. I am stuck just trying to explain what it meant to me and what it might mean to you if you are considering a gender journey such as mine. The easiest way to describe it is that it is an intensely personal journey that is often lonely and full of self-sacrifice. Which could also describe why the path or journey is so full of pressure to succeed in so many different ways. I say that because I learned on my path that there were so many different ways to achieve my dream of living the way I wanted to as a fully functional transfeminine person. Primarily I learned I did not have to be the most attractive woman in the room to be accepted. Maybe I could make it on my personality. Which is exactly what many ciswomen do.

When the pressure was off, the pleasure set in for me and I could begin to refine who I wanted to be as I pursued a rare second chance in life to rebuild myself in the image I had always dreamed of. I was fortunate when I found the right people, cis women, to help me along in ways they never knew as I filled out the little nuances of my gender workbook. As I always say, I had no idea of how many layers women have to go through other than men just to live their life.

I don’t think I had a choice in my life to not live the pressurized existence that I lived. It was all built into the path I chose to take, and I grew used to it. As a transgender woman, often it seemed I had more than my fair share of pressure to deal with. That is why as a tribe, trans women and trans men have proved to be very resilient over the time we have populated the world. Regardless of what haters and bigots think.

My Last Date as a Man

2026-05-03T10:00:00.187-04:00

JJ Hart in the long black wig
I wore to the concert.

My last date as a man was very eventful as destiny was sending me a powerful message.

It all began a couple of years after my second wife passed away and I decided to again seek out feminine companionship from a ciswoman. Then I made a mistake and became enamored with the mom of one of my servers at the restaurant I owned. Mom was about my age and extremely attractive and I gathered up the courage to ask her out when I learned she was single. From there we went on several dates including one in her native Cincinnati. I was quite naïve and thought things were going fairly well until my daughter got me two tickets to a “Joe Cocker” concert at an outside summer festival near to where she lived in Dayton, Ohio.

I guess the idea of perhaps meeting my daughter scared her off, because after initially saying yes, a week before the concert she abruptly said no and I wasn’t to call her anymore. By this time in my life, I don’t think anything could surprise or hurt me more than what I was already going through, so I picked up the pieces of this brief ill-fated relationship and prepared myself to move on. But I had one problem, what was I going to do with the other ticket I had for the concert. Then my mind came up with a plan, why not invite my feminine self? It would be yet another test to see how successful my transition was coming along as well as soothing the ego wounds from being turned down by what turned out to be the last date I would ever have as a man with a ciswoman in my life.

At that point, I was very much still in the closet to my daughter, so I planned to pick up the tickets as my male self then go home later and get ready. Getting ready proved to be an adventure as I knew I could put together an upscale/casual outfit for the evening. I ended up choosing a black outfit with a three-quarter sleeve mesh top and wide legged silky black pants with black sandals. Topping it all off, I chose my long black straight-haired wig and sunglasses on my head as an accessory. After carefully applying my makeup, I was ready to take on the world as a transgender woman out to her first concert. I felt good and confident for a change as I left the house for the half hour drive to the concert venue.

Once I arrived, I gathered myself, checked my makeup and took off walking to the concert which was filling up with people fast. Since it was still light outside, I could wear my sunglasses to check out anyone who was staring at me without them knowing. I was relieved when no one noticed the tall, long-haired woman in black making her way through the crowded sidewalk to her seat. I even had enough time to walk up to the concession stand and order me a refreshing drink before the late “Joe Cocker” started his show. By this time in his career, he played his hits and I was happy.

I ended up immensely enjoying the concert. Even more so since I was spending unique public time with my transfeminine self. I walked away from the experience with a new-found confidence in myself to live my life the way I had always dreamed of. In a world where ciswomen ruled. And maybe most importantly, I don’t think I embarrassed myself by the way I looked.

Maybe I was a little too over dramatic when I mentioned destiny setting in that night, but it did because never again did I set out to date a ciswoman as my male self and go through all the dating contortions I hated so much. I don’t know why but I always had felt so much more at ease when I was dealing with women as a trans woman and I never looked back.

My last date as a man was uneventful because it never happened it seemed for a reason. In the future I was able to have much better times going to places such as roller derbies with my lesbian friends where I could relax and have fun. Something I rarely did when I was trying to date as a man.

The Last Line of Defense

2026-05-02T09:55:49.273-04:00

Image from Gayatri Malthroa
on UnSplash.

Throughout nearly half of a century, my male self-fought the complete transition I made into a feminine lifestyle.

During that extended period of time, I think I tried everything possible to convince myself that I was wrong to want to play in the girls’ sandbox at all. As I mentioned in yesterday’s post, I “purged” many times of my feminine belongings. Leaving me with nothing but my most cherished pieces of girl’s/woman’s clothing and makeup. The makeup was easy because I knew I could always buy more. Perhaps the most precious items I never threw away were the nice wigs I was able to buy and the silicone breast forms which ironically were given to me by a fellow cross dresser who was purging also. Deep down inside, I knew I would need the wigs and breast forms again when my urge to cross-dress returned. As my own personal history told me it would.

It turned out that purging was not my last defense, no matter how hard I tried. In fact, the more I tried not to be feminine in any way shape or form, it seemed I slipped closer and closer to it. Especially when I learned I could dress to blend with most of the ciswomen around me. It was then I learned how natural I felt when I began to get it right and could feel all the gender euphoria I could feel.

What I did continually feel was my masculinity slipping away and I only used it on occasions with my wife in mixed company and when I was working in a high-pressure environment. For years, when I was out in the world experimenting living a new life, I felt as if I was sliding down a steep hill towards a transgender cliff which I had no idea of how I would be able to land.

In all fairness to my second wife, she never opposed me cross-dressing and knew about it when we got married. But on the other hand, completely opposed any idea of me becoming a transfeminine person. Between her and my male self, they made formidable opponents in my life when I thought about living as a trans woman. What made it all worse was when my wife kept saying she did not want to live with another woman and did not agree to that when we got married and I had to agree with her. Putting me in a very difficult situation in my life. I escaped the best I could by sneaking out of the house behind her back at any given time I found to test the world time and again to see if I would be allowed to go back behind the gender curtain. Which in many ways, represented escaping the last defense to staying in the male world I had.

Of course, my wife found out on numerous occasions what I was doing as a trans woman and resisted all my progress. When she did, we had giant battles which she normally won and I tried the therapy route to help me with my gender issues. Therapy helped me in many ways in my life but not so much with my deep-seated gender issues. I was expecting too much when one therapist told me if I thought our sessions would ever relieve my tensions, I would be wrong until I was able to make the final decision on if I was able to be a woman or not. At that point, I had two of the most far-reaching quotes that I ignored which were told to me. One of which was the time I was told I was the only one who could decide my gender future and the second was when my wife told me to go ahead and be man enough to be a woman. I was so sure I could do it my way and it cost me dearly. Especially, in terms of my overall mental health when juggling two genders and two lives at once became too much to handle. I did not know if I was coming or going on which day it was on how I was expected to act.

As many of you know, my second wife tragically died of a massive heart attack, leaving me with only my male self to do gender battle with. His last defenses deteriorated quickly as I became deeply unhappy and lonely and took solace in my inner female self for comfort. She stepped up big time, and very soon when I was not working nights, I was in one of my regular drinking venues seeking company. That was when I discovered I had more in common with the lesbians I met than with any man. Since most of them rejected me anyhow for leaving the good old boys club. I was able to say good riddance and go forward in my life into a world I never thought possible could ever be a part of. I had never really got along well with men in my life, and it turned out nothing had really changed. Except the way I was exploring the world. Finally, as my true self. As I was finding me after all those years of searching.

The last defense my male self-had was when my third wife Liz and only daughter came to my rescue with unwavering support for my final dive off the steep gender cliff. They made the landing very soft, and even easy. More precisely, Liz made me a believer in myself again and my daughter gave me support I needed from what blood family I had left since my brother rejected me, and my parents had long since passed away. Add in the couple of lesbians I always socialized with and I had all the support I needed to succeed in where I had dreamed of going and being accepted behind the gender curtain.

By far, I would be remiss if I did not mention the power of HRT or gender affirming hormones in removing any of the final defenses my male self-had going for him. I could not believe how fast the hormones acted as my body began to change, inside and out. It would take a whole post to describe all the impacts the hormones made to me. In fact, I have my annual appointment with my endocrinologist coming up this week, and with it, the chance to get refills on my hormonal patches.

Maybe I can thank her then for helping me to win my battle with my male self. Since I receive my HRT meds through the Veterans Administration, I always hope nothing changes from the top down with my ability to keep receiving a huge part of what makes me whole. I worked too long to get here.

Thanks again for joining me on my journey and I hope my experiences help you too.

Any comments, claps or subscriptions are welcome and make my work so worthwhile!

No Laughing Matter

2026-05-01T10:18:38.543-04:00

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!

In Praise of Femme Lesbians

2026-04-30T10:05:46.713-04:00

Image from Alexander Krivitsky
on UnSplash.

Back in the day, femme lesbians were known as “lipstick lesbians” and were usually in heavy demand from butch and super butch women in the community.

As I write this post, it brings back many unique and even pleasant memories for me. Why? It is because during that time in my life, I was desperately seeking where I fit in on the gender spectrum. As I drifted from point A to point B, I discovered the only place I really fit in was with the lesbian community. If I could only be accepted which was far from a given.

It all started with me when I was going to several mixed, male and female gay venues in Columbus, Ohio years ago. One night I was in a very crowded venue trying to get drink when I very butch lesbian offered to buy one for me. It was the first time I felt as if I was in the right place at the right time and someone appreciated me for who I was. It all started me on a path I still am on to this day with my third wife Liz who identifies as a lesbian. She was the one person and only one who had told me she never saw in male in me, but I am getting ahead in my experiences on how I arrived here.

It all basically started seriously when I started to go regularly to two small lesbian venues in Dayton, Ohio. One I was accepted in and one I was not. The one I was not accepted in showed their dislike for me in many ways, including shutting off the juke box when I played Shania Twain’s “I Feel Like a Woman”. No sense of humor at all! The other venue was the total opposite, and I even discovered I knew one of the bartenders from my male life. It was there that I had many exciting adventures into a terrifying world I did not know much about except when I was drawn to it and it was drawn to me. Going all the way back to one of the many diverse parties I went to in Columbus, Ohio when I hit it off with another woman and we took off and visited a very popular gay night spot called “Wall Street”. Since I was still married at the time, nothing happened except again I learned where I really belonged on the gender spectrum.

Through most of it, I was playing the odds, I could explore the world as a femme lesbian and still get home and cleaned up before my wife did. One night in particular was rough when a butch in a cowboy hat demanded that I sing karaoke with her, make no mistake that I am a terrible singer and wanted nothing to do with her but she was convincing and I thought of the only song that I knew to sing to was “David Allan Coe’s You have Never Even Called me By My Name.” And here I was sharing a microphone in my blond wig and tight jeans with a butch in a cowboy hat doing my best to let her do most of the singing. By the way, “David Allan Coe” just passed away recently in his eighties, and after I was done singing, I got the hell out of there when the butch said my voice was lower than hers and I never saw her again.

Other than my brief singing career, I had many more interactions with lesbian women and even my first time I was asked out to dinner came at the request of a super butch who went on to transition completely to a transgender man. Even though I was scared to death, I still managed to have a good time which set me up for future successes when I went to lesbian mixers with my friends. They were shy but I was not and ended up in several interesting situations when one woman said she should buy me a drink and take me home with her (I got the drink but did not go home with her) and the night I was caught kissing a strange woman by the pool table in a venue we were in.

Perhaps, other than the karaoke experience, the evening I was asked by my friend to be her “wing person” and approach another woman about getting her phone number for my friend. I never got that phone number, but I did get a once-in-a-lifetime experience to remember.

Being accepted the way I was by other women saved me from having to consider my sexuality at all. In fact, I was enjoying much more attention as a transgender woman than I ever had as a man when it came to other ciswomen. I think it was because I represented an alternative to many lesbian women who had experienced men in their past and did not identify as “Gold Star” women. Gold Star lesbians identify as women who have never been with a man sexually. To all the ones that did not wear their “stars” proudly, I represented a unique gender middle ground. It helped me too, when the ciswomen I encountered did not have the same sexual hangups that most men seem to carry around with them along with their fragile egos.

Maybe the best part was that I did not have any problems fitting in with my image as a lipstick or femme lesbians and was well aware of all they had in the LGBTQ community to make societal inroads which we always desperately needed. I desperately needed it too as I searched for where I belonged in life. All along I was a femme lesbian hidden behind layers of masculinity waiting to get out and enjoy the world. It was quite the coming out process for me. As I learned I could validate myself as a person without the help of a man which was exceedingly difficult for me to do sexually or mentally. Thanks to all the women I met, I never had to do it.

Connecting the Gender Dots

2026-04-29T09:55:57.168-04:00

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.

Stopping when You are Ahead

2026-04-27T09:55:56.340-04:00

JJ Hart. Girls Night Out.
I am top left.

Somehow, I never learned to stop when I was ahead when I was growing up. Or, as my parents always said, I tried when I was given an inch, I always tried to take a mile.

That whole idea really manifested itself when I began to explore my gender desires and start to cross-dress in my mom’s clothes. As I perceived myself to be successful with one new look, I always wanted more very soon. I could not stop when I was ahead and kept on pushing the boundaries of danger when I cross-dressed at home in the bathroom. Even if my brother was home too. I was risking what I had of the young male life I thought I needed to protect.

Somehow, my guardian angel was looking over me as I never got caught as a kid with my cross-dressing activities and I simply wanted more than I could get most of the time such as a nice, fashionable wig. Rather than the Halloween store wigs I was stuck with. Due primarily to financial constraints. During this time of my life, I was stuck with just being able to dream of what my life could be like when I grew into a more complete transfeminine person. It turned out to be a long (decades) away from coming true. Take wigs for example. When I finally arrived at the point where I financially could afford it, I went overboard on haunting the local wig stores around me looking for just the right wig which I thought would be the perfect addition to my hair collection to allow me to present better in the world. As I did it, mostly all that I accomplished was acquiring quite the collection of potential drag clown wigs which I did not have the patience and/or knowledge to take care of.

At that point, I could not stop when I was ahead or behind my quest to be at least an attractive woman. Every time I experienced the least little bit of gender euphoria when I went out in public, it fired me up and encouraged me to do more. Unfortunately, that meant taking extra chances with my actions and ultimately my safety. I needed to learn the hard way what ciswomen were raised to know about not putting yourself into potentially dangerous situations. I barely lucked it out when I escaped situations with no harm to me, so I essentially did not have to stop when I was ahead as a trans woman. I just had to be wiser when my male privileges were stripped away such as the personal security privilege men inherently have.

As I emerged as a wiser novice transgender woman, the reality of what I was attempting set in and I could not stop. Even if I was ahead. I began to set up a stairstep approach to my male to female feminization process which would I hoped, give me a more in-depth look at a woman’s life behind the gender curtain. Which I had spent countless hours thinking about. I started to consider all the things I wanted to discover as a woman that I had dreamed of as a man which led me to set up my own transgender mental bucket list of things to do. Basically, I set up activities at levels of difficulty. So, when I accomplished one I did not have to stop and move to another. Using the women’s room was a prime example of sliding behind the gender curtain and using a women’s only space. I knew a little of what to expect from my days as a restaurant manager when I needed to monitor how the women’s room was kept for problems I could encounter. Not starting from scratch helped me to survive in my new world with cis women.

Fortunately, I spent much of my time in the world successfully as I learned the basics of how ciswomen live. By doing so, I simply could not quit and kept on trying new things. My bucket was quickly being worn out by the challenges I was facing. Mainly by meeting the number of women who showed interest in me. I have always thought they were just curious about what I was doing in their world and was I living my life the best I could in the girls’ club. In my case, I was different and hopefully presented the best of the two main binary gender worlds as I socialized with many different women who seemingly were happy to see me.

By this time in my life, I simply could not stop what I had started as far as chasing my femininization process. It involved doing a deep dive into how women communicate and compete with each other, among other important things. Probably, communication was the most difficult aspect of my transition to learn. For the first time in my life as a transwoman, I needed to listen closely and completely to what was being said to me for hidden meanings and nonverbal cues. Then, as far as competition as a woman was concerned, I needed to learn that women compete just as hard as men. Just on a whole different spectrum of passive aggressive actions and reactions. Believe me, I learned the hard way a number of times when I made the wrong move and needed to watch my back from a smiling face who was out to get me.

Once I succeeded in learning all of my feminine lessons, my confidence was at a all time high. Especially with the small group of lesbian friends I had build around me by sheer luck. They ended up protecting me during my fragile times I was learning the final ropes of what it would take to round myself out as a transgender woman. By this time, my inner self could take over after being buried all those years and end up running my life’s goal that she always had a hand in. After waiting all those decades to live, she no longer had to stop while she was ahead. She was home and I was a whole person.

My Life's Passion

2026-04-26T09:52:50.392-04:00

JJ Hart on vacation
last winter.

Without a doubt, the one passion which has consumed my life the most has been my desire to be a woman.

I continually write about my youth as a confused boy wondering if I was the only boy in the world who wanted to be a girl. My desires extended all the way to what I wanted for Christmas (the doll baby I never got) all the way to when I lied about what I wanted to be when I grew up. Rather than rock the boat I always said some sort of a male profession such as a doctor or a lawyer rather than what I really wanted to be, a woman.

All I could do was take refuge in my mirror which told me I made a pretty girl out of the boy I was at the time. It became a passion for me to use as much of my free time as possible to cross-dress. At the same time, I became really good at acting like a boy by playing sports and having an interest in cars. I was so good, it kept the bullies away until male puberty invaded my body. Outside of hating the changes puberty was making to my body, I remember being intensely aware of my new masculinity and what to do with it. Even walking like a man was a chore for me to learn to do. I was so afraid of walking like a “sissy” and be made fun of by the bullies that I feared what to do. Little did I know that later in life my passion would be to unlearn all that I needed to learn at the time about being masculine.

As much as I tried and as tormented, I because of my gender passions, I could not seem to lose my desire to be feminine over my hated male image. At the time, I was in the midst of what I call the information “dark ages” before the internet and any social media input. Even the word transvestite was new to me as I struggled to find my footing in life. In other words, my gender closet was very dark and lonely, with little opportunity to have any future at all in my passion to understand and be feminine.

I stayed that way until I grew older and my passion included receiving my cherished issues of “Transvestia” magazine and I could read the “wisdom” of “Virginia Prince” whenever I could get my hands on another issue. For a while I thought it was working until I began to read about the social mixers certain chapters had to meet and greet other cross-dressers or transsexuals as they were known back in those days. Amazingly, one of the chapters in my native Ohio held mixers on a fairly regular basis that I could attend. I thought for sure, meeting others with similar gender issues could help me but I was wrong. Their passions exposed the many layers of where I could fit in (or not) with the remainder of the cross-dressing community and at the least, I hoped I could come away from the social by making a friend or two.

The only thing that really came out of the mixers was the knowledge that another chapter was coming close to establishing their own socials in Columbus, Ohio which was vastly closer for me to attend. Maybe I was too standoffish or even shy to make what I would call friends, but I continued to keep going any way and even was rewarded with invitations to smaller more diverse parties in Columbus which did not have to supposedly adhere to all of “Virginia Prince’s” archaic rules such as admitting heterosexual members only. As I said, the parties I went to were very diverse from lesbians to cross dresser admirers all the way to transgender women getting ready for gender realignment surgeries. The learning process I went through every time I went fueled my passion to learn more about my place in this new exciting world, I was becoming a part of. I could not wait to be invited to the next party.

I felt so secure from my party experiences, that I decided to do more exploring in my own in public. That is when I began to seek out the straight venues I used to go to as a man when I always wondered what it would be like to experience them as a woman. My passion for my new life exploded when I discovered I could be accepted which kept me out of the gay venues which I did not feel comfortable in at all. I was able to go out to be alone and mostly socialize by myself for the most part as I worked hard on my passion to fill out my gender workbook which was seriously lagging behind my fast-paced life as a novice transgender woman.

By this time, I had decided I had made the right decision to follow my feminine passion and try to survive in a world run by ciswomen. My path felt natural and I was rapidly coming close to the time when I was going to push all my male privileges I had earned to the middle of the table and bet my life on the transfeminine path I was on. I could not believe that my entire life’s dream/goal was suddenly within my grasp. If only I had the courage to finally follow through on my passion.

I did follow through and with the help of my future wife Liz, I went on HRT, threw out or gave away all my male clothes and never looked back on my male life except to decide which baggage to bring with me. I even went as far as taking female vocal lessons to try to teach me all important feminine communication skills which I desperately needed. It all turned out to be a labor of love as I listened and learned from the world around me.

The boy so long ago in the mirror finally had his deep-seated passions rewarded.

Burning my Gender Bridges

2026-04-25T10:11:12.776-04:00

Image from Kellen Riggin
on UnSplash.

Sadly, following my gender path included burning many bridges behind me which connected me to my old male past.

I think the problem stemmed from the self-destructive behavior I always exhibited when I did anything remotely successful as a man. I still had not yet faced the fact that I wanted nothing to do with being a guy, and everything that came with it. Including the potential of living with the white male privilege that was an automatic addition to my life.

Then, there was always the part of relief if I was ever caught cross-dressing early in life. Finally, I would be exposed as the deeply feminine person I really was. Life was much simpler back in those days, and I wondered how bad it would be to go to a psychiatrist and try to explain to him or her how I was not mentally ill; I just wanted to be a girl and my ultimate goal in life was to grow into a woman someday. The only way to get there was to risk everything and not get caught, but I never did and did not have to burn any bridges to find my way into early forms of conversion therapy.

It was not until much later in life did, I really began to torch my bridges behind me. The problem was, I needed to build my bridges longer and stronger to carry all the increased male baggage I had accumulated. Most of which was against my will. This was when my male life was outpacing my female life and I was building a small family and a very good job while at the same time managing to hang on to a long-term marriage where my wife was learning about and fighting against any thoughts of me sliding towards leading a transgender lifestyle. I desperately did not want her to be on any bridge that I burnt, and the pressure built on me not to light the match on my life if I took the huge step and decided to keep femininizing myself.

As I reached deeper and deeper into myself looking for an answer, I felt increasingly natural when I was attempting to put together my feminine self. No matter how risky burning my previous gender bridges behind was, I could not shake the idea I was doing something right by transitioning my old male life away.

The next big problem I faced was letting the world I was in know I was switching from my male club membership to the girls’ club. As I was being increasingly successful in carving out a new secret life as a trans woman, I did not want it to be secret any longer. So, I did the natural thing for me, I tried to make it impossible for me to turn back on my gender path. I started to go into my own restaurant dressed as me to see if I was recognized which I quickly was. I could have lost my executive general manager’s job immediately if I was but I was prepared to burn that bridge when I came to it. Looking back, it was not the smartest decision I ever made in my life but one I was desperate to make as my female self was crying out for attention.

When I progressed to a certain point in my male to female transition plan, burning bridges became just an automatic part of the plan because I did not need the male part of my life anymore, I was getting rid of. The prime example as I always point to is the night that something had changed in my thinking that I was not cross-dressing to go out and socialize, I was finally trying to formally join the world as a full-fledged transfeminine participant. The evening was a resounding success, and I knew from that point forward that I could never go back to being a man again. I could see my bridge burning over a not-so-distant horizon and it actually was scary and good at the same time.

I probably would have burnt more bridges earlier in my life if it was not for my second wife and my male self who was hanging on for dear life but still refusing to give up his hold on me. They put up a formidable fight to the point of putting out the fires I started on purpose. It lasted until my wife passed away, leaving only my weakened male self to fight me.

The final bridge to burn was when I was approved for HRT or gender affirming hormones. It was an all hands-on deck torching when my external and even internal body began to change. My sudden change in skin tone, slightly protruding breasts and longer hair which I refused to cut gave my external transition away and the part no one saw, but I felt, such as my emotional growth made itself known to me.

Following years of gender turmoil and change, having nothing in my way felt very good and I loved the hormonal changes I was going through with my new wife Liz. Which was well over a decade now. As I said, burning bridges in my life was always a scary idea but one I needed to do to get to where I wanted to go as a transgender woman surviving in the world of ciswomen everywhere.

I was fortunate in that I did not get burned as much as I did along the way in the process. I must have been quicker than I thought as my trans destiny showed me the way during the darkest nights. Who knows? Being caught on one of my bridges may have been for the best when I needed to work my way out of danger, but it never came to that with me. I became quite good at burning my bridges…or lucky.

Thanks to all of you who have taken the time to comment, clap or subscribe and just read along with me.

Without you, it means nothing!

Nothing Lasts Forever...or Does It?

2026-04-24T10:41:03.364-04:00

Image from Lucas Stankey
on UnSplash.

Yesterday when I first went to the bathroom to begin my start to the day, I turned the light on and was greeted by a slight “pop” and the bulb going out. I was disappointed that it was one of those bulbs that is supposed to last forever. Then, I began to think that nothing lasts forever, especially light bulbs no matter what they say.

As I normally always do, I took the idea I was following to another level and compared it with my old broken-down self. No surprise, but I was not built to last forever either. Just like my transgender desires, or were they? I know when I was very young trying on my mom’s clothes and makeup, I thought perhaps I would outgrow my desire to be a girl as I became older. As it turned out, the opposite was true. I did not outgrow my desire to be feminine; I grew into it as I became more skilled in applying make-up and cross-dressing myself the more, I wanted to try my newfound skills in the public eye.

When I accomplished the seismic shift from mirror approval to public approval, I knew any approval would not last forever because of the mixed reactions I was having in public where I tried to go. Outside of the usual gaggle of teen girls who would laugh at me, I found that the largest part of society did not notice me when I took the effort to blend in with the other ciswomen around me. The mistake I was making was very simple when I finally took the time to figure it out. To dress for success did not mean to dress to attract unwanted extra attention. Success meant that I fit in with the public at large. Carefully, since I was a large woman, but a woman none the less when I presented myself correctly.

At that point, the responsibility of being a stable presentable transfeminine person began to set in. Just looking the part of a woman would not last forever as by then I certainly knew I would never just outgrow my feminine desires. By responsibility I mean it became time for me to fully accept what I was becoming in the world. To catch up, I took feminine vocal lessons to improve the nuances of my speech patterns and worked hard to listen to my progress. If nothing was going to last forever in my life as a trans woman, I was driven to do it right. Outside of the very good job I had and the relationship I was desperately clinging to with my wife, being a transgender woman who passed in the world was my ultimate goal.

That point in my life became a blur as I was learning almost daily what went on behind the gender curtain, I was given access to. It was not all good, but I knew the bad would not last forever if I continued past the stop signs, I encountered on my gender path to my ultimate goal of shedding my male past. The best part was no one knew him and I could build a new life from scratch with the good and bad of living as long as I did as a man. Everything was going so well for awhile that I was waiting for the next high heeled shoe to fall on me since nothing lasts forever. Sadly, I was right when my personal world around me began to rapidly crumble.

I call it my dark period when almost everyone I cared about passed away. I knew about the finality of death because of my parent’s death, but I wrongly assumed I would be the first to go in the small circle of friends and family I had built up because of my self-destructive lifestyle.

The person who helped me out of my dark age was my wife Liz who made me a believer in myself, and my forever could be with her. That was over twelve years ago now, and I hope it can go on forever too. I am just grateful I was able to find her when I needed her the most because I was drinking way too much and struggling.

The moral to the story is that life is but a circle and you can ride out the down parts if destiny shows you the way. It was true for me that the darkest hour was right before the dawn when I attempted the ultimate self-destructive act of all. Taking my own life. I failed and ended up being able to live the most exciting and self-fulfilling days of my life. I would have missed everything from the tour bus experiences Liz and I took all the way to being humbled in my two fairly recent hospital stays for Covid and pneumonia. Sometimes I think I was just given the chance to do as much living as I could in the time allotted to me. Being transgender just added to the mystique of my life.

Whatever the case, I was completely wrong when I was a kid thinking I would grow out of my dreams of being a woman, transgender or not. Growing into my dreams was certainly the most challenging thing I have ever attempted. Sometimes causing me joy and sometimes causing me extreme pain and suffering.

I know nothing lasts forever, but when mine ends, I will know I gave it my best shot.

Recently I learned that even backwards Ohio who only concentrates of passing anti-transgender bills, is considering a bill which would legalize euthanasia for terminally ill persons. Even though I seriously doubt the republican legislature will pass the bill, it would be nice to be able to end your own life when the time has come and gone to do it. I would love to have control of my own destiny. Nothing lasts forever, including humans.

Sorry to end this on such a negative tone but death is as sure as birth and we need to make the best of it.

My Gender Workbook was Blank

2026-04-23T10:05:30.430-04:00

Image from Marcus Winkler
on UnSplash.

Somedays, I prefer explaining the trip up my gender path as filling out my gender workbook. Of course, the problem I had doing it was I had absolutely no help. No mother or peer group pressure to tell me if I was doing right from wrong when it came to cross-dressing myself as a girl or applying makeup.

Ironically (as I said in a recent post), knowing my mom the way I did she would have been against me shaving my legs and wearing makeup as early as I did as her secret daughter. I was only trying to get a head start on writing my own gender workbook and trying to catch up with all the girls around me who also were sneaking around wearing makeup and wearing panty hose.

It was fairly easy for me to make up my own workbook rules when it was just me and the mirror to deal with. No matter what I did as far as my feminine presentation was concerned was accepted by my mirror which kept lying to me and telling me I was a pretty girl. Which was much easier before I hit the curse of male puberty and all the changes my body was going through. I was seeing unwanted growth and angles while the girls I envied around me were getting curves. When I went to bed every night, I dreamed of my life being different but of course it never was. I would not get the curves I wanted until decades later in life when I was fortunate to have good health enough to be able to start HRT or gender affirming hormones.

There turned out to be tons of effort I needed to put into my workbook before I could arrive at the point where I could even think about starting hormones. The shortcuts I kept trying to make never seemed to work and usually got me in trouble. When I did find trouble by trying to do too much with poor fashion choices, finally I gained some sense, rewrote my gender workbook and went on to successfully try to blend in with the world of ciswomen as a transgender woman. Looking back, I think that page of my book had so many erase and start over marks that I could barely read it.

When I really began to get serious about seeing if I could be successful as a trans woman was when I desperately needed my gender workbook to help me, but it just couldn’t because I had not put the time and effort into filling it out. I had never given enough thought to how different the lives of men and women really were. Perhaps you remember the book “Men are from Mars and Women are from Venus” which when I read it, I wondered where trans people came from. I did not know yet we transgender women and transgender men get to occupy a special planet all our own with our unique knowledge of both men and women.

As I first began to mature into a more complete transfeminine person, I sometimes discovered my mental gender notes became overwhelming, and I needed to head back home to go over in my mind about what just happened to me. Good or bad, it did not matter. What was most unexpected to me was the amount of acceptance I received in the new world I was in. I had become used to the glares and abuse I took when I went out of the house in my early days and learned the majority of the world did not care about me one way or another. All the way to those other women who encouraged me to be in their world. Nowhere in my gender workbook did I ever imagine such a thing ever happening to a person like me just trying to find a new foothold in the world as my authentic self after all the years of struggling.

Sadly, there were still times when I ran out of ink to write in my gender workbook, and I attempted to purge everything I had accomplished and go totally back to my old safe male world. As most of us know, purges never work, and before I knew it I was out buying more feminine clothes and makeup to femininize myself all over again. By doing so, I finally came to the point of stopping obsessing over how I looked and settled into just being the person I was meant to be all along. I just did not want anything to do with me being a privileged male anymore, I just wanted to live out the long-held dream goal of mine to live as close as I could to a woman.

Even at that point, my gender workbook was different than other trans women friends I had known when I made the decision to live my life without all the major gender realignment surgeries and facial surgeries the others had gone through. I had two comments which described me the best when a transwoman friend of mine said I passed out of sheer willpower and another which came in on a comment and said I was just another old guy on hormones. Both were right in their own ways, and I wrote a mental note in my workbook that I would never be the prettiest woman in the room, but I could be the nicest. As far as the comment on me being an old guy on hormones, I wondered if the commenter was just jealous and it did not matter anyhow because I had always considered my gender to be between my ears and not between my legs and I had made it through life as far as I did with no surgeries at all, so there was no need to risk damage when I was older.

Also, I was fortunate to have been able to have other ciswomen around me help finish my gender workbook to where it is today. More than they ever knew, they taught me how to validate myself as a trans woman and welcomed me into their world. A major accomplishment in my life.

A More Innocent Time

2026-04-22T10:36:19.880-04:00

Image from Arun Sharma
on UnSplash.

On occasion, I look back at the early days of my cross-dressing past wistfully thinking those days were the innocent ones of my life before everything began to get more complicated.

In those days, all I needed to do was make sure I did not destroy mom’s pantyhose or stockings and be careful to put back her clothes where I found them. I guess I was successful because she never said anything to me. Using her makeup was much easier because she always kept samples in a side drawer in the bathroom, I could experiment with. At that time, the whole cross-dressing experience seemed to be an innocent game. Except for my deep paranoia about getting caught. Even the paranoia led me to being more creative about hiding my feminine clothes and makeup. What I had of it.

When the reality of serving in the military during the increasingly deadly Vietnam War slowly but surely made its way into my life, much of my innocence began to go away. The stark reality of going without my dresses and makeup for three years of my young life began to set in. After I passed my draft, medical exams and tests there was nothing I could do about it. Because I was not prepared to run to Canada to evade serving in the military. During that time as well as many years after I was honorably discharged from the Army, I continued to be quite naïve or innocent that all I needed to do to survive as a transgender woman in the world was to do my best to look really feminine. These were the days when my second wife and I battled back and forth about how I was cross dressing as a woman. She always thought my makeup was overdone and I was too fond of wearing “girly” fashion for her tastes. I tried to tone it down for the occasions we went out as two women but her expectations of me were so strict that if I followed her directions, I might as well not bother cross-dressing at all.

Even though I lost most of the battles with her about my evolving fashion sense, I won a few wars when she had to ask me for makeup guidance when we were going out to a fancier setting. Revenge was sweet. For a while, life was very routine for us as we both had challenging employment when we moved from our native Ohio to the suburbs of New York City, a real culture shock to us both. I was disappointed when the more liberal attitude I expected in the big city never materialized because we had to rent from an elderly Italian man and his wife who I knew would have never accepted a trans woman in their apartment. Long story short, my wife loved NYC while I disliked it and started my habit of rapidly changing jobs and moving to outrun my gender issues. Undoubtedly, I had entered one of the most exhaustive phases of my life as I tried to balance my growing transfeminine desires with a wife, a job and a family.

By this time, my growing one on one interactions with the public were driving what I had left of my innocence away. I began to realize that I was locked in a life-or-death gender struggle which may be impossible to ignore. What did I do? I exchanged my exhausting job changing for settling down in one great job opportunity, and at the same time begin to explore the new and exciting world of being a trans woman fulltime. For a time, I was fulfilled by both aspects of my new life until I began to be overwhelmed by the speed both my job and me being able to carve out a life as a new trans woman was coming together. I never imagined I would be so successful, and so terrified about what I would do about them together.

I like to refer to the process I was going through as trying to piece together a large, complex puzzle of life. On one hand, I had my male side loving the financial increases he was seeing. Then my female side pushing back to what was more important. Making money as an unhappy man or living a softer more fulfilling life as a transgender woman. Almost daily I struggled with finding the right pieces for my puzzle. All I accomplished was taking all the satisfaction I was feeling from either side as they battled on.

As I faced the new world I was living in, I was determined to be less self-destructive but that did not work either as I continued to do things like go to my restaurant competitors dressed as my authentic trans woman self. I was not that good, and it did not take long for the gossip to get out about what I was doing. Sabotaging all that I had worked so hard to achieve in my career to finally let people know who I really was. I was destroying once and for all my male past and the innocence was gone. However, with the loss of innocence came the deep feelings that I had finally made the right choice and everything I had done in life directly or indirectly had influenced my future. My primary example is fathering my daughter, who over the years has accepted me and I love very much. Without being forced into the Army where I met her mother, I would never have had the experience of my life. I am just fortunate that I was destined to live as long as I have to have the chance to see the pieces of my puzzle come together and have a chance to experience one of the most interesting and scary experiences a human can take. That of course is crossing the gender border from male to female to live on the other side.

I was never good with puzzles, especially my own, and to lose my innocence finishing mine was a real treat.