Showing posts with label makeup. Show all posts
Showing posts with label makeup. Show all posts

Thursday, March 19, 2026

How Much Discipline do you Need

 

Image from Brett Jordan
on UnSplash.



One thing I learned the hard way in my transgender travels from male to female was that it took an intense level of discipline to do it. In fact, cross-dressing as a girl was the first thing I ever did in my life which took a large amount of discipline. School was easy enough and sports were something I always tried at but never excelled at.

Growing up, I was always under pressure from my parents to finish any projects that I started and do them right. That is when the struggle began. I have written fairly extensively about how I struggled with the makeup arts when I first discovered all the makeup samples my mom had stashed in a drawer beside her sink in the bathroom. Using the samples meant I would have less chance of discovery when and if she discovered someone was in her makeup.

The only parallel I always use was how I tried miserably to paint all the plastic model cars I put together. My cars never seemed to come out as well as my friends and I really did not want my makeup to be the same failure as my attempt at modeling cars was. For the first time in my life, I developed the discipline to do something about wearing makeup and I set out to become better at it. Which included being able to purchase the right supplies with the meager amount of money I had to work with. I was under a lot of pressure when I did my own shopping for feminine accessories, so I needed to make sure I did not make a mistake and buy something which made me look like a clown in drag going to the circus.

Little did I know, developing discipline in my feminine pursuits was just the beginning of a lifetime search for a transgender future. Every time I turned around, I faced a new challenge, it seemed like I first went out in the world of ciswomen. Where I needed to be better to just survive. A prime example was early in my life as a novice transgender woman, I had a difficult time of getting out of the mirror and putting a complete feminine image together for the world to see. It seemed as if every time I thought my makeup and fashion looked good, my movements and voice were totally off, and I would ruin the whole image. I just had to develop the discipline to do it all and complete myself as a transfeminine person.

Experience was the only way it happened. The more I went out into the world, the more I learned about if I could ever achieve my trans woman dreams. It was very important to me to explore all my options before I made such a huge and important decision in my life. Before long, I was sneaking out of the house every spare moment I had to live the new life I was carving out as a transgender woman. The problem was, the whole experience was terrifying while at the same time, it felt so natural. Further confusing me on which way I should go with my gender issues.

One way or another, I was developing the discipline to conduct myself in the world of women with my own set of standards. I learned to dress and makeup myself to blend in where I was going and more importantly how to communicate with others around me when I got there. It took tons of discipline to do it. Especially when I was making the mistake of trying to live in both binary genders at once. I needed to force myself to make sure I was projecting the right gender at the right time mainly when I was at my job as a successful man. I can’t tell you how many times customers tripped up and called me “mam” when I was going about my male business. Secretly I was pleased but could not show it. The bigger problem I always mentioned was that the gender ping-pong I was playing took a tremendous toll on my mental health. Switching back and forth was terrible.

The only positive was that I developed more discipline than I had ever had before. When I was a man, I knew I was temporarily holding on to a lifestyle I no longer cared about and when I was a woman, I totally had bought into where I wanted to go with the rest of my life. The only thing left to do was to seal the deal and do it. And learn the fine little nuances ciswomen know how to exist in their world. Like figuring out who the alpha female is and going after her approval. Through it all, I was building layer upon layer of confidence in myself. Which I would need later when the dark period of being extremely lonely set in. The intimidating thought of finding anyone remotely able to partner with again looked very dim until all of a sudden it was not. That is when I found my current wife Liz over a decade ago and she made a believer out of my self again and I could drop all my personal defenses to ever loving someone again.

It turned out that all the work I put into disciplining myself into being a totally different person worked out for the best. I emerged from my work with a newfound lease on life as the transgender woman I had always dreamed of becoming. I proved my parents wrong. I could take on a project and see it through successfully. Just not the one they had chosen for me. I tried once to come out to my mom and was rejected and never to my dad, so I doubt they would have ever approved of what I did. Even though what I did was save my own life by shattering my gender shell.

It took a lifetime worth of work to improve my feminine discipline. Mainly because I was blindly entering a world of ciswomen I knew nothing about as my gender workbook was blank when I started. After making up for lost time, I fairly quickly caught up and entered the world as myself.

 

Wednesday, March 18, 2026

Time is All I Had

 

JJ Hart, Trans Wellness Outreach. 

Time is a fickle beast which sometimes comes back to help us, and other times it comes back to haunt us.

Depending on how far you are in your gender journey, perhaps you can remember your first experiences with the clothing of the gender you desired so much. Then again, I have heard from several readers who started their explorations at a much later age. Either way, time became a concrete reckoning to be dealt with. Mainly because time is a finite way of restricting all of us during our lives.

Since I have been fortunate to have been given a long/full life to live (I am seventy-six), I have seen my life come full circle in several areas. I have seen the joys of gender euphoria which kept me going when I hit the deep depression of stop signs and blind curves on my gender pathway. Through it all, I tried my best to learn from all my mistakes and successes. Little did I know I would live long enough to take advantage of everything I had learned. Or much of it as for much of my life I was always second guessing the decisions I was making. Did I make the right decision on taking a new job, or more importantly when I started to go out in public as a transgender woman and risking it all, was I doing the right thing.

What I did not take into consideration I had no real choice in what I was doing. From birth I was destined not to be the male person I was supposed to be. I had bigger and better things ahead of me if I broke the mold and was able to do it. I had the time to finally decide which path was right for me as I diligently explored the world of all the cisgender women around me. Then, a major roadblock arose when I was not allowed behind the gender curtain. The only time I was really getting out in public as a trans woman in hiding was at Halloween when nearly everyone knew me as a man. I badly needed other escape routes into the public eye if I was ever going to have the time to achieve my dream.

It turned out time was cheap in the middle years of my life as they turned out to be a blur. More and more, I began to sneak out of the house and explore the world around me as my transfeminine self. It was only then that I began to be allowed to be behind the gender curtain to see if life there what was really what I wanted. Spoiler alert, it was very much what I wanted as I even though many times I was terrified (yet excited) when I explored. I thought I had forever to do it and took my time trying to find new things to do as a transgender woman in a woman’s world. Which at times, still had me baffled about how it worked because I was still carrying around too much of my old male baggage. His expectations for the most part of how a woman acted in the world were formed from stereotypes he learned growing up as he watched women from afar and for the most part putting them up on a pedestal.

What I did not realize was my indecision to go all the way into the women’s world I was immersed in, was costing me years later on in life that I wanted back. Like everyone else I had assumptions, and mine were that I had plenty of time to research the difficult layered life of  and being a woman, when I simply did not which led me all the way to the age of sixty before I made the fateful decision to throw gender paranoia to the wind, pursue HRT, and change my life forever. While I still had the time because all the people I loved and respected in my life were rapidly passing away around me. The finality of death became a very real reality to me and if I was ever able to live my gender dream of living life as a woman, I had better do it while I still had the chance to enjoy it.

All I had was time was quickly fading away with all the people around me and I had very few people to make my own gender reveal to. For the most part, except for my brother and sister-in-law, my gender reveals were successful with most people telling me they were happy to see me happy. I guess one way to look at it is, if you wait long enough for your reveal you can be the last man standing becoming the last woman standing.

Going back to a theme which has popped up around here recently, if you are transgender you have given up all your rights to be a second-class citizen. And at least all you have going for you is that your journey has been an interesting one. From the earliest days of admiring yourself in the mirror all the way to earning your way behind the gender curtain, you have done it all.

Even though it maybe took a few years to do it, you know how difficult it has been to do it and every step needed to be carefully planned. One false move could send you back down your path and sometimes even worse than that. Ridicule by spouse, family and friends can happen at the same time your gender privileges were revoked. You feel helpless until you get your feet back on the ground to where you can continue and begin moving to a place where you always have known you should be.

For me, the time was now or never when I decided to live full-time, I had taken working on my feminine presentation, as well as being out in as many situations (good and bad) as I could. Anymore and I was just wasting my time and kidding myself if I did not pull the plug on my male life and get on with my future which I felt could be bright.

I saw the light at the end of the tunnel and for once it was not the train. I had paid my dues and was ready to live my life the way I wanted. Even though I ended up taking so long to do it, I was happy when I did. Age turned out to be more than a number for me, it turned out to be the magic time of my life.

Thanks to all of you for taking your precious time reading along!

 

Saturday, March 14, 2026

I Could Never Say No

 

JJ Hart with two Special People who 
made it Impossible for me to say No.
Liz on left, daughter on right. 




I discovered early in life that saying no to cross-dressing as a girl was something I could never do.

I tried many times, but I was a miserable failure as the pressure would build to run to my makeup and wardrobe to look at myself in the mirror. I even went as far as trying to shave the ugly unwanted hair off my legs with my mom’s electric razor. When I did, the world seemed to come together for me…for a while. Like clockwork, I could almost predict when the pressure would start to build again to cross-dress. Like most of you, I even purged or threw out most all of my feminine belongings in a wild rush which felt so good at the moment, until my old urges came rushing down on me. Saying no was just not an option.

For a while, I thought being feminine to the point of living as a transgender woman fulltime was always going to be just a dream. At other times, I thought that some point in my life I would just outgrow my gender urges and revert to a fulltime male life, no matter what my brain was telling me. I guess you could say, sometimes I thought a permanent purge would be in my future. I was kidding myself. That permanent purge never came as I tried many times to no avail. It seemed each time I tried to say no, my urges to follow my transgender needs came back even stronger. This time fueled by the positive feedback I was receiving when I was able to present better going out in public as a novice trans woman in a world of ciswomen. Just entering their world was much more difficult for me than I ever thought possible.

One of the problems was my old male self and my second wife did not participate in my dreams. It was far from my wife’s fault because none of what I was doing was anything she signed up for when we got married. She tried to help as much as she could, but my dream was growing so fast I could not control it. I started out the marriage as a cross-dresser and now I was into a transgender woman, and I did not have the courage, or knowledge to explain it. I just knew, I could not say no to pursuing my dreams. I am sure all she saw was her man slipping away. Sometimes slowly and sometimes quickly and I understood why she did not like it.

As I said, I really always knew saying no was not an option in my pursuit of a transfeminine life when I really went out into the world and found myself in the middle of new friendships who knew nothing of my past. growing Just trying to look the part of a woman faded away as I always thought it would when I found myself at the point of wanting to be that woman. Doing my best to communicate with the world on their terms. As I continually searched my soul for guidance on the path I should take, the answer always came back the same. Follow your instincts and do what you need to do to feel natural. With input such as that, why should I ever say no to myself again.

Finally, I reached the point of no return in my life when I needed to look at myself in the mirror to see who I really was. With no makeup at all one morning, I had a chance to see the real me and the words my wife Liz said to me came through loud and clear. There was no male in me and for once everything with a “no” word in it made sense. Plus, I was mentally exhausted from fighting myself all my life. I had enough, and it was time to make my final decision.

When I replaced no with yes, my life opened up to new horizons I never thought possible. Yes, meant I could be the long-hidden self I could never find. If you are on a gender path of your own, I hope you can do a better job of facing your truth than I did. I kept saying no too long and missed a significant amount of my life trying to outrun myself. On the other hand, changing a gender is a huge move, and one that cannot be taken lightly. You have to get to the point where saying no is not an option to you anymore.

 

 

 

Friday, March 13, 2026

The Power of Fear

 

Image from UnSplash.


The power of fear has always been a major factor to be dealt with as I made it through life.

At the beginning, I always used to run from fear by heading home to my makeup and skirts. Then, when that did not work as well, I needed to find another way to deal with the stress my fear brought on. All of a sudden, the extra feelings I brought to the whole cross-dressing experience began to be intertwined with the fear I felt about having my deep dark secret discovered. Every time I was not discovered, the relief I felt was intense.

As I grew older, the stakes I felt grew bolder when I took my image in the mirror public and into the world. The more I attempted to do it in public, the more my fear of discovery grew right with it. I guess it was because at the same time, my male life was flourishing and it was becoming riskier to give it all up, no matter how self-destructive I continued to be. I operated with the idea that if I had nothing to lose in life, it would be easier if I was discovered and life as I knew it came to crushing down on me.

My prime example of turning abject fear into success came from the night I decided to try going into one of the big venues I had visited as a man but this time as a woman. Something clicked in my mind, saying I was no longer a cross-dresser, I wanted more, like a ciswoman in the world doing the same things I had done as a man. Before I did though, I needed to see if I could even cross the threshold in the TGIF Fridays I was going to, to try to find a seat at the bar. Sure, I could have chosen a table instead, but I wanted to go all out and try to look for more interaction at the bar instead.

As I sat in the car, before I went in, I was literally so scared I could hardly breathe. I don’t remember how many times I checked my hair and makeup in my car mirror. Finally, I had enough, hitched up my big girl panties, took a deep breath and headed for the venue’s entrance. Deep down I knew if I was successful, I was facing yet another major transition point in my life and I knew I could never go back. Spoiler alert, I worked my way through all the fear I was feeling and managed to have an enjoyable time with the rest of the women just getting off work at a nearby mall. Even to the point of ordering another drink. Plus, I was right, I found my life could never go back to the male existence I was forcing myself to live. I had discovered new transitions as a transgender woman in the world.

More importantly, I discovered fear of what I was about to do in my new exciting world just came with the territory. It became as much a part of me as a well-worn set of panty hose when I went out into the world. Eventually, I just learned to live with my misgivings about giving up all my male privileges I had earned in life. Another example came much later after I had completed my male to female femininization, even to the point of starting HRT, or gender affirming hormones.

It happened one hot summer day when my future wife Liz suggested we go to one of those auto junk yards where you pick your own parts. We needed a side mirror for one of our cars and it would be much cheaper if we could find one there. All of a sudden, my old fears materialized about going back into a male-dominated environment. Again, I remembered the old days when I battled fear all the time and I had to keep reassuring myself I was not back in the not so good old days, and I would be fine. It turned out, all the fear and trepidation I felt about going was wasted because the men at the junk yard barely noticed me as they went about their business and we found a mirror for our car.

These days, since I have been out in the world for over a decade now, almost all my lifetime fears and anxieties about being a woman have passed like I do most of the time now. Mainly, I pass now as old which there is nothing I can do about. There are times when I do miss the adrenaline flow of being afraid propelled me into the world as a novice transgender woman. I do think, however, that conquering my gender fears came from my days in Army basic training when everyday we needed to fight to make it through. Then somehow, I used it all to help me be a better woman. Before I became a better man at the very end before I transitioned because I was allowed behind the gender curtain to get a look at how ciswomen live.

The end result was that fear helped me battle through the conflicts I felt because of gender dysphoria. It sounds different I know, but that is the way it worked for me.

 

 

 

Monday, March 9, 2026

Set in Stone?

 

JJ Hart

When we are born, we are assigned a gender which is arbitrarily based on our genitals the doctor sees. Often, at that point, gender reveal parties are set up by new proud parents. Of course, the problem is what if the child does not agree with how the reveal was going but had no say in the process. That was exactly where I found myself.

I was born as a first son into a male dominated family, so as I grew, I learned what was expected of me. Be a success, compete for it and earn my male privilege was my only path. I was caught with no way out, seemingly, I was stuck in stone. My only path to sanity was the very limited time I had to cross-dress in front of the mirror and try to transform myself into the pretty girl I always wanted to be.

The first time I saw a glimmer of hope in my future as a transgender woman was when I started to go to Halloween parties dressed as a woman, just to see how I was perceived. Overall, I felt as if I got a fair reception and could not wait for Halloween to roll around again. I found I could not wait and began to come up with other ways to test my feminine presentation in the public’s eye by simply going out to malls and women’s clothing stores. Looking back, some of my adventures were just OK and others were brutally bad as I learned what I was doing. One of the main things I learned was presenting as a woman was not set in stone. Often, I could take advantage of the seasonal variations in women’s fashion to change up my own look, which made the fashion process so much more challenging and fun. I needed to up my diet game to fit into more stylish clothes I hunted down at the thrift stores I shopped at. I liked many of them because I could try on my potential treasures in the women’s dressing rooms with no problems.

All of this led me to believe that maybe my gender situation was not set in stone, perhaps I could find my way out of the life I was given. I just needed to be sure that escaping the stone I was in did not put me in quicksand. Or was the transgender frying pan worse than the fire. With my newfound confidence, I set out to discover the answer to as many of my gender questions as I could. I knew I felt an energy in life I had never felt before and it felt so natural that I wanted to experience more. But even with all of that, it wasn’t enough to keep me satisfied with my slow transition. The basic question remained that could I ever gain the courage and where with all to live my dream of existing as a full-time transgender woman on my own terms. Sadly. I was not going to learn that answer for years because my male life kept getting in the way.

By in the way, I mean he kept setting up major roadblocks of my proposed path such as what to do about my wife of twenty-five years and the very successful job I had worked so hard to get. I cherished both of them and did not want to let them go. I am sure, this sounds familiar to many of you in the same situation. Especially when you think your male situation is set in stone and you can’t get out.

I thought the same thing for years as my mental health deteriorated as I drank way to much trying to self-medicate my problems. The part I never understood was how I could think what was true today would be true tomorrow. Destiny for me completely turned me around during the dark days when my wife and almost all of my close friends passed away, leaving me almost completely by myself. Except for my daughter and my brother. On top of all of that, the Veterans’ Administration healthcare system, which I was a part of suddenly approved the use of HRT or gender affirming hormones for qualified veterans who were approved through a therapist to receive them. I was approved and prepared myself for my second puberty and the greatest most profound changes of my life.

Suddenly, everything I thought was set in stone, was not. I was free to live the way I had prepared for all my life had come true. I could even dare to be happy for the first time in my life. It was always set in stone that happiness could not be part of my life. Thankfully I was wrong about that. It was just a matter of learning where I truly belonged and then getting rid of that giant roadblock I was born with. My so-called gender because it turned out to be true, I was never supposed to live a male life after all. All the years of struggle and emotional pain were wasted on a fight that I was never destined to win.

As I always say, I was not a man cross dressing as a woman, I was a woman cross dressing as a man to just get by in life. I was fortunate in that my gender destiny was not set in stone no matter how determined my family around me was to keep me male, I always found a way to sneak around their backs and keep that feminine flicker of hope alive. Now it is able to burn brightly due to no small help from mainly new friends and family. Roadblocks were moved and now the path is straight and smooth as I am able to live the dream I always wanted.

As I said, remember that today does not dictate what tomorrow may bring. I always say, life can change on a dime. If you can find the dime.

 

 

 

Thursday, March 5, 2026

More Euphoria

 

Image from Marcus Winkler 
on UnSplash.

Yesterday, I wrote a post describing the joys of gender euphoria and promptly received this comment from “Joey”:

Hello JJ! I am Joey. I discovered your blog today from a link on Stana's blog, femulate.org I am a crossdresser who presents male while wearing tasteful, feminine outfits. I do feel some euphoria, primarily when I have been out in normal life while dressed pretty for a couple of hours, and all of the stress hormones go away. Only my wife and a few other people know about this side of my life, so it is stressful when I go out in public every week or two. But after the stress, it is very freeing and happy!

First of all, Joey, welcome to the blog! Hope you enjoy it. The feelings you described were similar to mine too. I know I could not wait until I could shed my male clothes, wear something pretty and sample what the world had to offer for me that day before I had to go back to my old boring stressful male existence. Sure, I felt stress going out as a transgender woman when I first started to do it, but it was nothing compared to my male life. When I was mistaken for a ciswoman, my heart literally sang with joy, and the best part about it was, it all felt so natural. What a homecoming!

My only caution about seeking out more of the male to female femininization process is, it led me to take premature chances with my life. I did not understand all the layers that went into a woman’s life and the only way to gain understanding was by doing it. It was only then that I was given the opportunity to look behind the gender curtain to see what really went on. As I did, I was surprised to learn that many things were the same and women learn in their lives to keep certain things secret from men. Which is why both genders have such a difficult time understanding each other. For example, ciswomen have developed two basic ways of negotiating their lives which have to be understood by any novice transgender woman.

The first is the use of non-verbal communication. Women often give information to other women through their eyes and bypass men all together. I can’t tell you how many silent warnings I got from other women when I was in potential danger from a toxic male.  The second major lesson I learned was how to operate in the new world of passive aggressive women. I needed to have my head on a swivel to look for some other woman coming after me after she initially was smiling and was nice to me. I looked at both of these major changes in my life as just another way of playing the game, and the only problem I had was switching gears when I had to go back to my male life. I had built a career of being aggressive in my business and the change was often difficult for my mental health.

Even though the path went quite slowly for me several times in my life, on occasion, it sped up. Almost to the point of being out of control. My male self-had a unique way of saving his existence when it was on the brink of being taken away. Which made matters worse in my convoluted gender world. How could he continue to be so strong in his resistance when my gender euphoria was so strong when I was successful as a trans woman? I am sure you can understand my dilemma and perhaps have even been there yourself. Somehow, someway, I needed to arrive at a point where I did not define myself as a transgender woman. I defined myself as just me.

Sadly, that point did not come for many years in my life. As my male self-fought long and hard for his right to live on in the world he was successful in. Many times, I good old shot of gender euphoria was all I had to keep going if I was ever going to have a chance of reaching my feminine dream of attempting to live full time. Fortunately, for my life-long dreams, my gender euphoria turned out to be strong too, in its own way. Far past the feel of hose on shaved legs and the sound of my high heels when I walked, all the way to having the confidence knowing who I was. Acquiring the ability to look and another woman eye to eye and communicate on her level was so important to me as I needed to break the communication gap I had with the world when I started to live as a transgender woman.

I am aware that gender euphoria can be different for all of us as we follow our gender paths. Referring back to “Joey’s” comment that she enjoyed being tastefully dressed when she went out. That became so important to me too when I was able to begin to blend into the everyday world as I knew it. Out went the too short miniskirts, replaced my more tasteful denim skirts was a prime example. I was told my legs were always a fashion positive for me so I wanted to show them, but I learned moderation was the best way to go when it came to my male to female femininization process. When I did, my moderation led to a different kind of gender euphoria when I searched for the best way to find my dream.

Euphoria, I found, is also joy of living in a feminine world. Where I always dreamed, I could be. More importantly, once I got there and was living my dream, it was everything I thought it could be and I started to wish I had not waited so long to do it. Of course, thinking that way was just wishful thinking because we are given only one life to live.

I learned I had made the best choice I could and living as a woman was the way to do it.

 

 

Friday, February 27, 2026

The Dream was Never Out of Sight

 

Image from Egor
Vikrev on UnSplash

On occasion, I write about my ultimate dream of someday living as a fulltime transgender woman. As is the case with any dream, making it a reality is often very difficult, and it forever remains a dream. The main problem I had was having the confidence to move ahead on my seemingly endless gender path. Somedays, it was like I was walking on air in my high heels and others, it was like I was walking through quicksand. I would be confidently clicking away in my heels until I hit an unseen crack in the sidewalk and almost broke my ankle, which was a prime example of my life at the time.

Even on the days when I was doing my best impression of a linebacker in heels, I tried to keep my head up and look to the future. Hoping for a better day when I could do a better job of presenting in the world as my dream woman. Growing up in my male life, I was accused continually by my parents of never finishing a task. It turned out, working towards my dream of crossing the gender border was the first real project I never quit on. Take my use of makeup for example, I would not rest and kept experimenting until I got it right. I became so good that my second wife would break down and ask me for advice on how to do her makeup. I don’t think she ever knew most of my makeup knowledge came from the night I gathered the courage to take off my wig and makeup and have a true professional redo my face and more importantly explain to me what he was doing as he did it.

Those were my shallow days of thinking being a transgender woman just meant looking like one. As I was told many times by my second wife, I made a terrible woman because I had not paid my dues to achieve my own womanhood. The whole process set my dreams way behind because there was little to no way of me sliding behind the gender curtain to gain the right to play in the girls’ sandbox. How could I ever achieve my dream, if no one would let me in was the frustrating question which I had over and over again. In the meantime, I was stuck cross-dressing in front of the mirror and keeping my dreams alive and knowing deep down someday I would achieve my own unique transfeminine womanhood.

The main problem I had was gaining the confidence I needed to keep my dream alive because deep down I had doubts about whether I could ever make it. Because at the time, all I had were the annual Halloween parties I went to. Even the parties were a struggle on occasion as I needed to figure out my “costume.” I went from thinking that sexy was the way to go, all the way to trying to fool the other attendees into thinking I was a ciswoman who just got off of work. By the time several Halloweens had rolled by, I had achieved my dream of being mistaken for a woman but then was faced with the dreaded what then? Looking ahead at waiting another year for a costume party was unbearable and damaged my dreams of trans womanhood. I knew from my party results I was becoming tantalizing closer to my dreams but getting there still seemed like they were miles away.

As I finally began to leave my mirror and gender closet and explore the world, I began to understand what my wife was trying to tell me. I was a terrible woman out of ignorance as I tried to mold an entirely new person. All I had to work with was my appearance which was just skin deep when I needed to communicate with mainly ciswomen in their world for the first time. For my “sandbox” I chose the bar scene which I was used to and provided me with many unique situations. Many of which I don’t recommend. Along the way, I found myself as a single woman in a bar attracting unwanted attention until I built a group of friends to mingle with. Fortunately, the vast majority of those people who wanted to interact with me were women, so I did not have to worry about a bunch of drunk toxic men.

As I survived this stage of my life successfully, it was time to seriously consider where I would go next. Would I stay where I was at, afraid to go any farther, or would I be brave and take the next step which would be HRT or gender affirming hormones. Following much thought, I decided to seek the HRT path by going to a doctor. By doing so, I discovered what a huge portion of my life I was missing. My body took to the hormones so naturally that I felt I should have been on them my whole life. Just another indication to me of how close my gender dream had always been. I just needed to reach out and grab it.

Perhaps, you may have a similar dream for your life. Mine turned out to be a single-minded pursuit of me wanting to cast aside being a man and start being a woman. Regardless, the way I did it could be different from yours. I chose a “stairstep” method of my male to female femininization process. What I mean is, every time I was successful at one level of my transition, I needed to choose another gender project. If I wasn’t shopping for that new favorite outfit, I needed to figure out where I was going to wear it, is an example.

When I finally made it to the point of being able to live my dream, I certainly had paid my dues and had a lot of help from friends to therapy. They all helped to lift me from being a so-called terrible woman into a well rounded trans woman living her dream which was never far out of sight.

 

Wednesday, February 25, 2026

Everything was OK Until it Wasn't

 

JJ Hart. Frozen in Florida

So many times, when I was caught between my genders, I learned everything was Ok, until it wasn’t.

A prime example would be when I was coming home from a night in the gay venues I was frequenting and my car decided not to start when I was twenty miles away from home. Then I needed to figure out how to get the car home before my wife came home and took off all my make-up acting like nothing had happened. What I did was call a towing company and get the car towed back home as I sat in the cab with the driver, trying my best to present as a blond woman just trying to get her car home. Somehow, I did make it that night and learned to never take that car again when I went out on such a pressure packed adventure.

Sadly, I needed to learn the hard way as I followed my gender path through many blind curves and major potholes. I would usually start out with a final look in the mirror thinking I made an attractive woman from the testosterone poisoned male I had to work from. Confidently, I moved ahead to whichever venues I decided to go to that night. And the stakes were raised significantly when I decided to leave the relative safety of the gay venues behind and attempt to see how I could do in the straight world of big sports bars. It turned out, if everything was going to be OK, I would find out quickly.

Normally I found everything was going to be OK, except on the nights I encountered problems using the women’s restroom and I ended up having the police called on me. That turned out to be more embarrassing than anything else because the cops had better things to do as I was just sent on my way. A more embarrassing night came along much later when a group of drunk guys decided it would be fun to play “Dude Looks Like a Lady” about five times in a row on the juke box. Which ended me getting asked to leave by the manager, even though I was a regular. Well, liked by the staff, who actually tracked me down at a close venue not long after and asked to come back. Telling me, the manager who told me to leave got fired. I was flattered and accepted my welcome back because everything I thought was OK, actually was.

Other times, I was not as fortunate as I began to learn the basics of being allowed to play in the girls’ sandbox. Learning the time-honored tradition of passive aggressive behavior which ciswomen practice so well, proved to be a challenge. I was used to taking another man at face value most of the time until he proved himself unworthy which did work with women. I learned a smile could be hiding something much more sinister. Resulting in claw marks down my back. Once I did, again everything really did turn out to be OK and stayed that way for the most part.

In no way, do I want anyone to think this gender male to female feminization project was a quick one. There were so many nights when I hurried home to return to my old unwanted male self that I wondered what I was doing. I was risking so much on what often seemed to be an empty dream of someday being able to live as a fulltime transgender woman. What kept me going was the deep feeling I had that when I was my feminine self, I felt so natural and I felt as if I somehow was home. And someday, all the setbacks I had would just disappear and everything would truly be OK.

Through the magic of gender affirming hormones (HRT), and strong ciswomen role models, I was able to weather the transition storm I was going through. I knew everything was going to really be OK when I found I could validate myself in the world as a trans woman without the validation of a man, or anyone else. The whole process was so much more complex rather than just looking like a woman. I needed to be my own woman, on my own terms so I could exist on the path I had always been on. Even though sometimes I did not realize it myself. Those were the days of feeling like a failure when a group of teenagers laughed at me for how I looked. Rather than staying and trying to do better, I had to run home crying and go back to my cross-dressing drawing board. Seeking the idea that everything was going to be OK, even though it was not at the time.

As I said, what kept me going was a small spark of feminine energy deep down inside me. Knowing for sure, being the woman I dreamed of being was going to be an incredibly complex gender journey to make. Just lacking the communication skills, I needed to survive in the world as I went one on one with other women made my life a scary one. Since I was shy to begin with, I needed to start from scratch in a new world and work hard to gain an equal footing as a novice trans woman trying to make it alone in the world until I was able to make new friends.

The new friends I made helped me to cushion when I got into situations when everything was OK until it wasn’t. During those times, I could fall back into the group and learn from what was going on. Every learning experience became so important because I could make sure to never try that again. Even what was left of my stubborn male self-learned the misconceptions he had about how women truly lived and did he really want to let go of his life for good.

When he did, I found that everything was going to be OK and it always was.

Sunday, February 22, 2026

Did I Believe in Magic?

 

Image from Delphian Lacub
on UnSplash.


It is rare, but on occasion, I still hear the question of when I knew I had gender issues.

The truth of the matter is, I always knew I was transgender. I just did not know how to express it until I was older. It was after my early explorations into my mom’s clothes did, I realize the potential magic I was holding when I carefully tried on her clothes knowing fully it would not be long until I would outgrow all her wardrobe and I would be in never-never land when it came to finding feminine clothes to wear.

Somehow in the near future, I made do with stretching elastic girl’s clothes I found in the lost and found box at the school I went to. I had a short skirt I managed to squeeze into that I cherished forever it seemed. Around that skirt I managed to build the basics of my style with the money I earned from allowances and stray jobs I found. I delivered newspapers and even mowed a cemetery for a dollar a hour in the hot summer sun, just so I could sneak out to a store and buy more feminizing items. Through it all, I believed in the magic which made me who I truly was.

It was always difficult for me to hang on to my trans truth because at the same time I was experimenting with being a girl, my male self was actually able to establish himself successfully in the world. Which just served to tear up my fragile mental health enough. Until you must wake up in the morning wondering if you are a boy or a girl, you don’t know what I am talking about. I would not have wished it on my worst enemy.

On certain occasions, my magic was strong and I felt like a girl when I looked at myself in the mirror. On other occasions, life was hell when I could not find the time to sneak around and cross dress as the girl I was. It was during those times; I had to rely on just that small amount of magic to get me by. One of the problems was I was so envious of the other girls around me at school in their pretty clothes and admiring looks from all the boys. I dreamed of being just like them.

It wasn’t until I began to explore the world as a novice transfeminine person, did I finally realize what my magic was all about. All of the doubts I had on where I was headed in my life began to dissolve when I began to feel so natural in my progression. Life was a blur as I was going out to be by myself in the world as a transgender woman. By doing so, I was able to meet strangers who accepted me for who I was. For the first time in my life, I was able to shed the long shadow of the remnants of my male past.  Every night, I was able to find my way out to one of my regular venues, be it lesbian or straight, I never wanted to return to my male self at all and lose my magic.

It turned out, my magic never went away, it just became stronger. So much so that I made the move to forever give up my male ways and start gender affirming hormones or HRT. The hormones just reaffirmed and strengthened my belief that magic could happen and I could indeed be the transgender woman who could forever lose her male past and survive. I could change my life from being married, with friends, family and a great job into a much more mellow existence.

It just took me too long to realize how deep my magic went in my life, and how backwards I had my whole existence and how much pain it caused me. It was my fault because I did not believe in my own magic enough to do something about it rather than be a part-time cross-dresser. I always point out I have nothing against cross-dressers at all because I depended upon it to live my life for so long.

Did I believe in magic? No. Should I have, absolutely.

 

 

Tuesday, February 17, 2026

Is It All Competition

 

Image from Gavin Allenwood on 
UnSplash. 


As I began to follow my gender journey, I did have some sort of an idea on how cis women compete in the world and how it differs from men. The one mistake I did make was thinking women somehow operate in a kinder/gentler world when it comes to competition.

Once I was allowed to play in the girls’ sandbox and get into a couple brief but intense scuffles with other women, I learned the hard way that women were into it as much as men when it came to what was important in their lives. The difference being was what was important. Men of course, compete in athletics and business while women tend to build their lives around family and home. And let’s not forget the influence of appearance with women. While it is a shallow existence, some women have a tendency to make friends and socialize with other women who fit in with their appearance. I remember quite clearly trying to watch my pre-teen granddaughter try to socialize with and fit in with a much prettier girl at a birthday party she was at. This extended with me all the way to a lesbian mixer I was at one night when a friend of mine wanted me to approach a very pretty femme lesbian for a date for her. It turns out that both my granddaughter and lesbian friend were both out of luck.

Not unlike when men try to date beautiful women and get rejected. I know when I started down the path of getting out in public as a novice transgender woman, I was only concerned about my appearance. I felt I was working to compete one on one with the other women in the world I met. How was my makeup, hair looking and did all my accessories match the rest of my outfit was all that was important to me. It took me awhile to go through this portion of my life as a cross dresser and emerging as a wiser more mature feminine person.

It was also about this time when I started to really engage with other women. Which was a real challenge because I was so timid. What would I say and how would I say it became I bigger priority other than just how I looked. I discovered too, the power of the submissive compliment to start a conversation. An example was when another woman would come up to me and compliment my earrings to start a conversation. When in reality, she was just curious to find out what I was doing in her world. In particular, I found out that I needed to beware of the you look great compliment because it could be tied into a compliment such as a man dressed as a woman.

It turned out, when I built my own circle of ciswomen friends, I did not need to worry as much about competition in the world anymore. When I was approached, it was when I was part of a group of out-going women who without thinking, shielded me from any negative people. The process worked wonders for me because I could set back and learn how to act from the other women around me and only step up and out when needed to secure my place in the group.

Slowly but surely, my competition turned to confidence that I could live the dream life as a transfeminine person I never thought I could be. I began to join writer groups with my wife Liz which in turn helped build further my new life because these people never knew anything about my previous life as a male. It all separated me from my old unwanted life and propelled me into a future I so wanted.

Furthermore, I did not have to compete in the world with other women. If they had a problem with me, so be it. It was their problem not mine. I did not have to please everyone was a powerful moment in my life. But without all the gender competition I went through, I would have never made it to the point I am today. I learned from how men compete with each other as well as women from both sides of the gender spectrum. Typically, men don’t compete well with women at all, and I knew that going in. So, I knew what to expect. With other women though, I did not have any idea at all. It took me a long time to learn feminine competition and how it worked.

As I said, once I did learn to compete in the real world as a trans woman, my life changed for the better and I truly began to live the life I always dreamed of.

Sunday, February 15, 2026

Missing in Action

 

Image from Miquel
Adjuelo on UnSplash

The reason I have been missing in action this time started with a fall I took a week ago. It was bad enough my wife Liz had to call the squad (ambulance) to get me on my feet and to the hospital. It turned out the flu I had contacted on our vacation had gone to my lungs and was causing the start of pneumonia.

In the emergency room the gender questions started almost immediately. I had two nurses checking me in  It did not take long to happen.  As one of them was checking my records which I knew said female, the squad driver came through and called me “sir”. So, the nurse appropriately enough asked me what I would like to be referred to as. I explained I was still biologically male but was living as a transgender woman as well as living with a woman and that was where the mistakes happen. She had other things to do and quickly moved on from me without commenting. But I knew the gender fun was just the beginning because this was not my first hospital rodeo.

I was prepared to lay my naked gender self out to a multitude of strangers I did not know. The only thing I was sure of I was not prepared to spend five days in a hospital to do it. Of course the first thing that  happened was the nurses had to get me into one of those infamous hospital gowns which are open in the back and begin to start to stick me in the arms to begin all the spots they would need to inject me with fluids and draw blood work which turned out to be a daily occurrence.

As far as my being humbled when my male nakedness was exposed was when the staff had to install a device to hopefully catch all my pee before it hit the bed. For the most part the device worked but when it did not, I had to be totally naked to the world as I was cleaned up. I was fortunate in that I had a staff take care of me who did not seem to care about my gender at all except for one nurse who infuriated me by referring to me as “buddy”. She might as well had been calling me “sir”. But for the most part, I received good treatment and eventually was released back to the loving care of my wife, and my daughter and son-in-law even drove down from Dayton, Ohio to visit me. They brought me flowers and candy on their seventy-five-mile trip. (one way).

The whole adventure was obviously not planned, so I did not have a chance to even clean up and shave before I went. So my best foot forward was in leggings, tennis shoes and a sweatshirt. But even as the admitting nurse said, they don’t expect everybody to be fully made up when they enter their care. Which made me feel better.

Speaking of feeling better, finally I am catching up on my sleep and feeling rested from my daily blood draws which had to be done at 5: 58 am every morning and even a person coming through at 2:00 am one morning to make sure I was wearing my safety sox…really? I guess it is no wonder why I feel so tired. If the sickness doesn’t make you tired certainly the hospital stay will do it for you.

As far as anyone else questioning my gender, they never did or did it behind my back where I could not hear them. Now my goal is to start writing again on a regular basis as my health returns. Thank you all for your patience.

 

 

 

Friday, February 6, 2026

Invisibility as a Trans Girl

 

Image from Lindsey Feanzke
on UnSplash, 

Another major realization I had during my wife Liz and I’s vacation journey was how invisible I had become as a transgender woman.

It was not an easy realization to come by since I have been out in the public eye full time for over a decade now. During that time, I went through all the stages of going from sheer panic all the way to suffering from impostor syndrome when I found myself in a feminine world for the first time. Along the way, I had heard the term stealth applied to the impossibly feminine transgender women I had seen who had passed the public perception of beauty easily. A standard I never thought I could reach with the testosterone poisoned body I had to work with.

In many ways, I found I never could but then I began to look around me at all the other ciswomen in the world who did not achieve a high standard of classic beauty either. And they found a way to lead successful fulfilling lives as women. When I realized they had a path, I knew I had one too. I could be secure in my own womanhood even though my path was different than most of the world. The only real problem I had was dealing with the late start I had dealing with my realization that I was a transfeminine person all along. I was blessed with having the advice or criticism from moms or peer groups to help me out of my gender shell. I only had a mirror which was highly capable of lying to me on my feminine presentation. Even though I looked like a clown in drag because of my poor makeup skills, my mirror friend kept telling me I was pretty.

It was not until It began to have the courage to use the world as my mirror did life begin to change for me. I needed to pay closer attention to what the ciswomen around me were wearing so I could blend in with them and not create unwanted attention to myself as a transgender woman. In other words, I did not know it yet, but I had my first lessons in being invisible in the world as the person I had always dreamed of becoming.

Little dd I know, the more I was out in the world, the more lessons I would have to learn to just survive carving out a new niche in my life. It was one thing to talk to myself in the mirror and a whole other to communicate one on one with another woman n the world. Early on, before I gathered much courage in what I was doing, I would lay back and let the other person (normally a woman) take the lead in any communication efforts she wanted to do. I found it was the best way to go as I learned what the gender I so desperately needed to be a part of operated behind the gender curtain which men could only guess at. I became comfortable in women only spaces such as restrooms and parties where men were not invited. In doing so, I was making myself more invisible as a trans woman and more visible as a well-rounded person.

All of this brings me back to what “stealth” as a transgender person means to me. For the longest time, as I said, I thought the word applied to only the upper echelon of transsexual beauties I saw online back before anyone could use filters to make themselves look better. Back in those days, feminine facial surgery was the way to go to re-arrange what you were born with in the appearance department. Seeing how I could not afford any surgery and was still working as a man, I was stuck with trying my best to improve my looks through the miracle of makeup.

By this time in my life, I was approaching my sixties and had managed to carve out a nice little life with affirming women friends, I decided to take to heart again what my trans friend Racquel had told me years ago. She profoundly said I passed out of sheer will power and I took it as it was intended. That I would never be the most attractive woman in the room but I could survive anyhow as I found my path as a transgender woman beyond the point of ever living a male life at all and I was now invisible to the world as my former self. After all the decades of attempting to live as a mix of the two main genders, I had made it to the point of just being me. More importantly, I was able to show the public around me who I was too. Now, it could be when one ciswoman on the trip came up to me to tell me how much she respected me coming along on the tour, it could have been she was referring to me making my way with my walker on wheels, or the she sensed I was transgender. One way or another, I respected what she said.

It turned out she was not alone. To my surprise, I had several other couples tell me the same thing and they were the ones I least expected to do it. Which teaches me once again not to prejudge people ahead of time. Shame on me, because I hate it when people prejudge me.

I guess becoming invisible for me came the same time I learned to just be me and I my life’s journey just happened to include being transgender. Now I need to keep trying to adjust to my new realizations. Since it took long enough for me to do it.

 

 

Thursday, February 5, 2026

The Return Home

 

JJ Hart, on a chilly
Florida beach night.

The return home from a rather lengthy vacation always presents a bittersweet time for me. While the trip to Florida went well and for the most part exceeded my expectations, our return to our home in Cincinnati and to our very lonesome cat was welcome. Similar to being able to sleep in our own bed again.

During this trip we played hide and seek with several major weather systems. In order to stay ahead of the foot of snow, which was heading for our native Ohio, the bus tour company decided to leave a day early and take a different route South to Florida. It proved to be a masterpiece of planning because we faced just a tiny piece of snowy weather around Knoxville, Tennessee and none of the dreaded ice. Which went Southeast of us.

By nature, I have become a worrier in my old age, so on top of thinking about all of the weather issues we would be facing, I had to put the restroom anxiety I always feel in the back of my mind. Which was a good thing because outside of a few startled looks I received from other women on the tour, I had no problems with my choice of restrooms I used. In fact, the biggest issue I faced was trying to wait for a handicapped accessible stall to use which really helped me with my mobility issues, I was able to not use my cane at all and rely heavily on my walker with wheels.

Past the restroom issue, I had to adjust to using my most feminine voice again. An issue because I don’t have to think about it as much around home because I don’t interact with strangers much. Day one proved to be more challenging on my part because I was so shy with the others on the tour, and I was afraid I was coming off as unfriendly or bitchy. I was fortunate in that we had two experienced tour guides who helped me find handicapped accessible ramps and restrooms.

As past trips and experiences have taught me, when I take the first step with a smile and friendliness on my part, most people respond the same way. So, by the time the tour of Florida was over, several of the other travelers made it a point to tell me how nice it was to meet me. I couldn't believe how good it made me feel. It was enough to warm me up even in the record Florida cold spell they were suffering through.  It was so cold and windy for them that they canceled one of the Everglades boat tours we were on. It all worked out for the better for Liz and I because we got extra time to explore the beach which is why we went in the first place. Plus, the leisure time helped me to recover from all the days we spent which required lots of walking. In fact, one day when we went to the Hollywood Beach area of Florida, we ended up walking over seven thousand steps, well over what I was used to.

Overall, I had a very good time on this trip even though it was to a part of the country I don’t agree with as far as politics are concerned. But my native Ohio is rapidly trying to become just as backwards as far as transgender rights are considered.

What did I wear? The whole trip was casual themed and all I took along was my best leggings and jeans, along with a solid pair of tennis shoes for walking. Other than that, I wore sweatshirts. With a daily shave and a liberal dose of my favorite foundation powder. I was ready to go for another day of cold Florida.

As I said, we made it home safely and had a good enough time that my wife Liz is planning the next trip which may include something to do with train travel. Plus, I will be writing more about other in-depth events on the trip.

Wednesday, January 21, 2026

Staying Calm

 

JJ Hart, Cincinnati Pride

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

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

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

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

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

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

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

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

 

How Much Discipline do you Need

  Image from Brett Jordan on UnSplash. One thing I learned the hard way in my transgender travels from male to female was that it took an in...