Showing posts with label trans woman. Show all posts
Showing posts with label trans woman. Show all posts

Saturday, February 28, 2026

Innocent until Proven Guilty

 

JJ Hart


In many ways, this post is an extension of yesterday’s article. It involves the constant gender dance my second wife of twenty-five years and I had through in our marriage until she passed away.

Most of the problems occurred when I could not face the truth about myself. I was much more than a casual cross-dresser and just having the occasional chance to dress in front of the mirror in my feminine clothes was just not enough to satisfy my dreams of becoming a full-fledged transgender woman someday.  That was when I entered the most shameful time of my life when I like to say, I started to cheat on my wife with another woman who happened to be me.

As with most cheating episodes, mine became very complex. First, I started innocently enough with me taking short trips out of the house by walking around our neighborhood. When I got away with that, I started driving around as a trans woman to nearby cities where no one would know me. It was when I began to gather the courage to get out of my car and start exploring clothing stores, malls and book store to name a few. Before I knew it, I was hooked and I was having lunch on my own, just to see how successful I would be as a novice trans woman. Amazingly, I found the world was mostly nice to me and I kept experimenting. Which put me directly in the crosshairs of what I pledged to my wife. That I would never go out in public as a woman. She even went as far as letting me have the money to rent a motel room where I could dress and go out.

I even abused that privilege and still left the house on a regular basis. The problem that I had was removing all the traces of makeup that I was wearing when my wife was gone and I had to pass her strict inspection when she got home. Before long, regardless of how hard I tried to remove all my makeup, I was guilty until proven innocent. My wife knew I had been out, no matter how much I lied and tried to talk my way out of it.

Once I started seriously down my gender path to trans womanhood, I can confess I was never quite innocent. I would look for any opportunity to get out and about and improve my worth in the world as a woman. To be sure, I was not proud of what I was doing, but the whole process felt so natural that I just had to keep going and challenge myself to see what was around the next corner of my life. Even though the whole lifestyle change I was going through was so scary, it was also exciting and natural. As if something deep down inside of me knew I was on the right path.

As I always say, all of the lying and sneaking around took a tremendous toll on my mental health. All of my insecurities came to light when my normally honest life was torn apart by lying so much to my wife. I guess you could say too, for a while I was lying to the world about who I was too when I first started to go out in the world. I was guilty with strangers who did not know they were interacting with who I really was, not some sort of drag act. In fact, it took me several meetings with the same people to overcome that major obstacle in my life. The last thing I wanted back in those days was to be connected with any of the negative talk show press the cross-dresser transgender community was getting. Or even worse when we were being compared to someone who was up to no good by disguising themselves as a woman to commit a crime.  As a group back then, we were guilty until proven innocent.

I was fortunate in that I managed to purge my feminine self about six months before my wife died, so at least, I could do the right thing and honor my promise to her for a short time. For a number of reasons, it was the longest six months of my life.  It turned out when she passed, I would never have to consider purging again. Except when I made the major decision to finally give away all my male clothes for the last time. The best and most complete purge I ever made.

As I reached that point in my life, I vowed that honesty would always be the best policy and I would always be innocent until proven guilty. It turned out my inner hidden female had always thought the same thing and when she had the chance to see the light of day, she made a honest attempt to do the best she could to take the ball and run with it. When that corner had been turned, it was like I had been freed from a giant weight on my shoulders. I could breathe again and be fully proud of who I had become, a whole transfeminine person.

I can’t say it enough, the days and years of lying and deception on my part was totally my doing because I did not have the courage to face who I really was. I have no excuse for my cowardice except for my male self just did not want to give up what he worked so hard to obtain.

Certainly, I would not wish any of the gender turmoil I went through on my worst enemy and if the politicians who keep passing the anti-transgender bills across the country had to walk a mile in our shoes, they may have a whole different understanding of what we transgender women and trans men face on a daily basis. Then we would be judged to be innocent until proven guilty, which we rarely are.

 

 

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.

 

Thursday, February 26, 2026

Honesty was Always the Best Policy

 

Image from Jon Tyson on 
UnSplash. 

Very early on in my life, I thought my default mechanism to anyone challenging my masculinity would be to lie about it. Fortunately, I did not have to take that route often because of all the elaborate ways I utilized to hide my feminine desires. Examples were the times I was competing in sports or working on cars. People close to me just assumed I was a “normal” male.

It wasn’t until much later in life when I began to get serious about dating women, did honesty become a real priority when it came to explaining my life. My first experience with telling a woman I was serious about, has been relayed several times here as recently as in the last several days. She is the one I coerced into dressing me head to toe as a woman which was the first time a ciswoman had attempted to do it for me. The whole plan turned out to be a disaster because of so many things. As I have mentioned before, I just wasn’t that impressed with the outcome she presented to me as she applied my makeup and the long blond wig I so desperately wanted. By then, I had spent years doing my own makeup and I thought I did a better job.

Little did I know that disappointment would only be the beginning of many with her. Being honest in our relationship early on led to an engagement but then a total break up because of a date I had with Uncle Sam and the Vietnam War. Rather than support me as I served, my then fiancé insisted I tell the draft board and the world I was gay to try to not get drafted which would have been a total lie. I knew I was a cross dresser but also had a pretty good idea I was not gay. Instead of wrecking my personal life as I knew it, we broke the engagement and went on our not so merry ways. I knew where I was headed, the US Army for three years. It was not the most pleasant time I ever spent in my life, but at least I was honest with myself.

Time went by in the Army until I found myself in a place to exercise some of my cross-dressing desires by going to a hospital Halloween party I was invited to by friends. By doing so, I through caution to the wind and decided to go all out dressed as a woman. I only had about eight months or so to go in the Army, so I was willing to risk getting in trouble to satisfy my need to cross-dress after such a long time of being denied.

All three of my closest friends that I socialized with all the time were at the party too, and as luck would have it, several weeks later, the subject of our “costumes” came up after a long night of enjoying very good German beer. When my turn came to talk about how I had went to all the effort to femininize myself for one night (including shaving my legs), I finally just was honest with my friends and told them I was a transvestite and the Halloween party was far from being just a one night deal of seeing what it would be like to dress as a woman. It was the first time I had ever admitted to anyone that I had a fondness for being a woman, so it was quite the liberating experience.

It was also a far-reaching experience because included in my group of friends was a woman who I got to know quite well. So, well in fact that later on we went on to be married and she became the mother of my only daughter who I cherish to this day and is one of my biggest supporters. Obviously, from day one in our relationship, she was aware of my feminine desires and accepted them.

Much of the same happened with my second wife, who was much more strong willed than wife number one. Even so, I felt honesty was the best policy and I nervously told her again I was a transvestite or cross-dresser before we were married. Ironically, the problem came with me not cheating on her with myself. What I was increasingly doing was doing exactly what I had sworn not to do. Leave the house dressed as a woman. By doing so, I broke one of the main bonds of our marriage which was not lying to her about what I was doing all the time.

Needless to say, like any other ciswoman, my second wife had keen instincts of what I was doing and was constantly on the outlook for things like extra forgotten makeup on my face when I was out and about as a novice trans woman. Since I prided myself in the rest of my life on my honesty, the constant lying I was doing to the woman I loved broke my heart. Especially when I could not stop doing it.

My heart was further shattered when she passed away quite unexpectedly from a massive heart attack and I was on my own after twenty-five years of marriage. The only redeeming thing I did was completely purge my feminine side for six months before she died. Even to the point of growing a beard. It was the only thing I could do to try to redeem myself.

Ironically, her death forced open the biggest door to my honesty there was, being honest with myself. When I looked deep, I found that all along I had been just wasting my time trying to be a man with all the privilege that came with it. I had learned to play the male game effectively but did not want any thing to do with my gender prizes after I won them. Being honest with myself for a change was the best feeling of all except I did feel guilty about all the stress and tension I had put others through because of my inner weakness. Total honesty certainly would have been the best policy in my life.

 

 

 

 

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.

Friday, February 20, 2026

Time Flies When you are a Crossdresser

Image from UnSplash. 
Since now I have been blessed with making it to the age of seventy-six, I spend a lot of time wondering what I did with my life.

As I mentioned in yesterday's post, I spent much of my time running from myself by changing jobs and moving my family. At the same time, I was doing all of that, I was busy cross-dressing to keep my fragile mental health together. I started the same way most of you with gender issues did by trying on my mom’s clothes and moving on from there. The urge was so strong that I even went out and got a newspaper delivery route (back when newspapers were relevant) so I could make extra money to buy my own makeup, panty hose as well as other feminine items I could afford. Before I knew it, I was becoming fairly proficient at applying my own makeup. So good that the first time I talked a ciswoman into making me over into a woman, I thought I had done a better job with my makeup.

Those were during my college days which were split in two by my military duty during the Vietnam War and all cross-dressing activities were brought to a complete halt. When you are younger, years are more precious and the time away from my makeup, dresses, and wigs seemed impossible to face. Somehow, I made it through and even discovered the magic of attending a Halloween party dressed as a woman while I was in the Army. The good news is I did it but the bad news was the time was very limited, and I had a lot to go over in my mind including Halloween was then another year away. What would I do in the meantime to help solve my cross-dressing dilemma.

What I tried to do first was to drink my gender problems away, which only partially worked because when I sobered up, my issues were still with me and sometimes potentially worse when one night in the Army I told three close friends I was actually a transvestite and like to wear women’s clothes. Not just at Halloween. I was lucky, the word about my gender issues never got out to my higher ups and I went on to serve out my time with a honorable discharge.

When I rejoined civilian life, I had the chance to seriously consider making the gender jump from a male life to a female one. Following serious consideration, I felt the leap would just be too far to make, so I reluctantly chose to stay on the cross-dressing path I was on. To do just enough in front of the mirror to maintain my sanity.

Nothing changed until I began to leave my mirror behind and experience life in the public eye as a novice cross-dresser. Or so I thought. All was good, until the night something clicked in my mind when I was getting ready to go out to the straight venues I was visiting when I left the gay spots behind. As I examined myself in the mirror, I stopped and said what I was doing.  I suddenly felt empty and needed more and then concluded I had taken just dressing as a woman as far as I could. I needed to experience the next step which was actually interacting one on one with other women as an equal. Even though the idea scared me to death, I needed to hitch up my big girl panties and transition again into a full-fledged transgender woman. The venue I chose was TGIF Fridays I was familiar with as a man and I knew if I could make it past the hostess stand with no extra attention, I had a good chance of finding a seat at the bar with the other women who were just getting off work at the nearby mall. Amazingly, my plan worked to perfection, and I made it to the bar and claimed my seat. The bartender waited on me without showing any signs of gender disgust and I even ordered a second drink to celebrate my successful major transition in life. From serious cross-dresser to novice transgender woman. Even saying the word felt good to me.

By the time, time was flying by as I was trying desperately to build a new transfeminine life while at the same time maintaining a long-term marriage and successful job. I found I was not too successful as a juggler because the same time I was feeling good and natural as a trans woman my male life would sneak back it and ruin it for me. Eventually, it all became too much for me to handle mentally, and a suicide attempt followed.

Maybe I spent too much time in my life obsessing over my feminine appearance which I attribute into being a very serious cross-dresser. Certainly, all the successful public appearances I made as a woman were not helping me with my ultimate goal of living my dream. In the long-term, I never bargained on going through two major male to female femininizations to even come close to discovering if I could find my true life and live it as a successful trans woman. Maybe I was too shy or scared to go too fast. One way or another, it is too late now to cry over torn panty hose. Life gives us only one chance to get it right.

Wherever you maybe in your gender transitory journey, I hope you can steer clear of the major roadblocks’ politicians are attempting to out in our way as transgender people. May your path be as smooth as possible as your own time flies by as a cross-dresser or transgender woman.

  


Thursday, February 19, 2026

What is Chasing You?

 

Image from Filip Mroz
on UnSplash. 

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

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

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

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

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

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

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

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

 

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.

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.

 

 

Wednesday, January 21, 2026

Staying Calm

 

JJ Hart, Cincinnati Pride

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

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

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

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

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

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

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

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

 

Tuesday, January 20, 2026

Her Way or the Highway

 

Image from Joshua Rondeau
on UnSplash. 

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

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

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

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

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

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

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

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

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

I was more like my mom than she ever knew.

 

Saturday, January 17, 2026

No One Way is Correct

 

Image from Gabor Kaputi
on UnSplash. 

Even though we transgender women and trans men often follow similar gender paths to get to our goals or dreams, it is still true that one path (the one you are on) is the only correct one. Plus, don’t forget there are so many side trips to take such as surgeries and hormones to help us along.

For example, I read about and hear from other transgender women who have elected to undergo major and costly gender surgeries (like Amber) which they deeply feel they need to feel whole, while me, on the other hand have decided to steer clear of any surgeries. Mainly because they don’t define me as a trans woman. I know what my brain is telling me gender-wise and just don’t need the corresponding equipment between my legs to improve my overall being. Although let me say I understand why somebody else would and if I was younger, I might have considered the surgical route. It just took me too long to figure out who the true me was.

Other than surgeries, I took the same path as many of you. I experimented with my mom’s clothes and makeup since I did not have any sisters, all the way to service in the military from those of you who are approximately the same age as I am such as Bobbie W. who even served on her version of the American Forces Radio and Television service as I did, although she was in the Navy. It amazes me how small the world has become because of the internet that many of us did not have in our formative cross-dressing years. Besides Bobbie, over the years, it has amazed me how similar some of our paths have been and it would not have surprised me if we had not met along the way. Except if you were like me, you were desperately attempting to hide your true self from everyone else in the world.

Then there were the evenings when I did see another transgender woman in one of the venues, I was a regular in, other than Racquel who was a trans friend of mine. One in particular was at a TGIF Fridays I went to quite a bit. I watched this well-dressed large woman step up to the bar and order a red wine, then before I could even attempt to introduce myself, she was gone and I never saw her again. So, on that occasion, I did have my path crossed by another transfeminine person since I could not attach a label to her such as a very accomplished cross dresser. Outside of a few “women” I saw shopping in the grocery store over the years, I learned how rare our tribe really is.

One of the reasons we are so rare is that all of those still in the closet due to their gender issues have not had the chance to be out and be counted. Mainly because of all the male baggage they have fears of losing. It is terrifying to think of losing baggage such as spouses, family, friends and jobs to name a few of the bigger ones. At least it was for me as I went through life frustrated with the amount of male baggage I was accumulating.

Even though, when I started blogging years ago to pay forward and help others similar to me in the closet, it occurred to me my plan had backfired to an extent, and I became a role model to some of my readers. Some even wrote in and called me some sort of a hero to them which humbled me because I never set out to do anything like that as I was just trying to live my life the best I could. Writing about my life was Now adays I keep trying to say I am no hero but merely someone who was terrified to leave her closet and live in the world as I knew it. Certainly not a hero by any sense of the word.

Recently, another point that I have been trying to make is there is no right way to achieve leaving your closet and living an authentic feminine life. Sure, it takes a lot of work and effort to achieve doing something the greatest majority of humans have never considered trying. Especially when we live in a negative atmosphere where a certain melon felon and his political party are trying to demonize us. Hopefully, that all will stop happening when the population finally tires of us and seizes the opportunity to vote on the real issues. Which makes it so important that even if you are in your closet, you vote your true conscience this coming midterm. So much for my political rant which is urging you all to get on the right gender path and stay there through the elections and beyond.

In the meantime, always hope for the best when you are out as your authentic transgender self. Your confidence will keep many of the middle of the road haters and bigots away because humans are like sharks, they sense blood in the water. How you get there is determined by many factors, but the main one is you can only gain confidence by going out into the world in your heels and doing it. Other than that, a disarming smile will take you a long way too. Keep in mind that most people don’t care about you, they are only concerned about themselves, and you will be ok.

As you do it, don’t worry about making the big mistake and you will be much freer to be you. You are on the right gender path because you are on it. Sure, it will have many curves and roadblocks but sometimes all of them make the journey much more worth it.

 

 

Friday, January 16, 2026

You being You or Playing up Being Different as a Transgender Woman

JJ Hart
At first glance, the statement of what makes you, you, seems like an easy one to answer. Especially if you are not transgender. Because you are in the majority and not perceived as being different.

For cisgender women or men, lives are set up to be lived in a certain pattern from birth till death. Using a baseball reference, life throws you a real curve ball when you are trans. Because you are different and often pay the price. The sad part is, for the longest time, we have such a hard time explaining to others our gender issues when we don’t understand them ourselves. In my case, it took me years to come to the conclusion I was not a man cross dressing as a woman, I was a woman cross dressing as a man, and I was not stuck with some sort of a weak excuse such as I was a woman stuck in a man’s body.

I grew up in a semi-dysfunctional family which valued being different. Until it infringed on what mom and dad thought was right. So having their oldest son want to be their daughter would never have been accepted. Or that was way too different for them to understand. I basically went on with my life knowing I was different and not knowing the information I needed to know if anyone else felt the same way.

Before I knew it, I was on the path to male privilege if I just did my best to earn it. The only problem was, I did not want to be on it. It was as if some invisible force was keeping me there against my will. Sometimes, it was easier not to expend my energy fighting my gender issues than to actually begin to leave my mirror and seek out attention in the world. It was only then did I begin to learn if my transgender dreams could ever become a reality or would forever remain a dream until I die. I just knew, both of my parents had lived relatively long lives so I should have time enough to do what I wanted.

In the meantime, I did what was expected of me. Such as reproducing an offspring daughter, earning two college degrees and serving my country in the military. I was not different than many of the other men around me, and life was a blur during this time. The worst part was, I was still not coming any closer to learning if I had any possibility of living my transgender dreams other than the occasional Halloween party. I was still paranoid that others around me would learn of my gender difference and often I would wake up in the morning wondering if I was a man or a woman. Which certainly set my day off on the wrong foot and I am not even adding in the vivid dreams I was having when I was a pretty woman. It would often take me hours to fully return to the disappointing relationship I had with my life as a man.

All the relationship did was continue to cement my unwanted claim of being a semi-successful man. I often wonder what I could have accomplished if I could have given my male self the full attention he sometimes deserved. Not the partial attention he received when I was inwardly thinking of what my life would be like if I could live it as a transfeminine person. It was as if something was telling me to put the brakes on acquiring any extra baggage as a man that I would have to get rid of when and if I was able to transition from male to female. It turned out, the learning curve I went through as a male helped me anyhow as a transwoman, because I was a stronger person. Which really came in handy on those lonely nights when I was out trying to be myself and not the self that made me different.

It was not until I made my gender differences an accepted part of me did I begin to experience success with finding new friends in the world. Since I could not deny what I was, why not utilize me to make me more attractive and I don’t mean in the physical sense. I was like other cisgender women who may not be the most attractive woman in the room but there was something about them which set them apart with their inner glow. I knew if I could harness my inner glow, I could go much farther in life and dispel for good that there was any dreaming left for me to do.

Literally without thinking about it I had crossed the line and transitioned again. I had went from being a serious cross dresser all the way to being a transgender woman and then to being just me. I had spent all the time around the cisgender women that I knew for them to accept me as an equal behind the gender curtain and I did not have to feel any different any longer. I did not have to seek out a mirror to reinforce in my mind who I was. I had sorted my male baggage and kept what I wanted and discarded the rest, so I was ready for my next big challenge which was being approved for gender affirming hormones or HRT. When my body took to them so naturally, I was able to take another big step towards doing away with what made me different from other ciswomen around me. In fact, I wondered what hormones some of the mean women I knew were on. They must have had an overdose of testosterone somehow in their diet.

While it is often difficult to emphasize the differences which make you different as a transgender woman or trans man in today's world, your differences can still be a positive influence when someone gets to know the real you.

 

  


Thursday, January 15, 2026

Gender Lost and Found

Image from Jon Tyson on UnSplash.

I spent most of my life in the gender lost and found department.

It all started when I discovered my fascination with my mom’s clothes and was lost when I outgrew all of her wardrobe. I was fortunate when I found a elastic, stretch mini skirt in a box outside the girls’ locker room one day and managed to hide it away in my gym bag and take it home for myself. What was lost was now found.

Along the way, I ended up wishing my overall gender dysphoria could be solved as easily as finding a skirt I could squeeze into and wear. It was only the beginning of a lifelong search to finally face up to who I really was. Until I faced up to the fact that I was never male at all, I was lost in a life I did not want.

Slowly but surely, I began to find my way out of my dilemma. But before I did, I needed to gather all the courage I could to leave my mirror and experience the world, as terrifying as it was as a transfeminine person. It was only then could I see the possibilities of what my future might hold if I actually followed my dreams and was able to live a life on my terms as a transgender woman. Along the way, I found out more about myself than I lost as explored the world. Surely, initially (as I always point out) I was treated rudely in a world which was different back in those days. The world was more likely to find humor in my efforts to be feminine than today when more and more people are just mean. To a point where they will share their unwanted bigoted feelings with you. Every time I was laughed at as a novice cross dresser, I resolved to head home to the safety of my mirror and attempt to fix the problems which were holding me back.

What I found was, I was not trying hard enough to blend in with the ciswomen around me. I needed to lose my male ego which was telling me to run from the criticism I was receiving and for the first time, pay attention to what the world was trying to tell me. Get out of the teen girl fashions I was trying to be seen in and start trying to determine my strengths and go from there.

The more I learned about presentation as a trans woman, the easier my life became as I began to test the boundaries of what I could do. For the most part, I was successful in building the basics of a new feminine life other than the times when I tried to go too far into venues I should have never considered trying. Ironically, one of the biggest set of venues I needed to lose were the gay bars I was going to. Even though, for the most part I found I could express myself there, my growth as a person was slowed dramatically. I tired of being rejected as just another drag queen and wanted to find something more. Losing the gay bars except on certain occasions was the best move I made except when I found acceptance in a small lesbian tavern I went to regularly along with the bigger sports bars, I found that I could be a regular in also.

As I expanded my feminine horizons, I lost more and more of my male self who had always wondered what it would be like to go to his favorite venues as a woman. I found I was right and enjoyed myself even more as a transgender woman. Especially when I went there enough to be recognized as a person, not some sort of a man in a dress. My golden rules of being accepted almost always worked for me as there were three. Number one, be friendly and not be a bitch. Number two never cause any trouble, and number three always tip well.

The only problems I found were when I needed to separate who I was in the real world when I needed to go back to being a man and existing in my working world, I increasingly wanted nothing of. It was a fast-moving pressure packed macho world which I could never see myself doing a male to female transition in, so I was lost in limbo much of the time. It was the only major problem I found I could do nothing about and had to give up a well-paying job when I retired to a fulltime transgender woman’s world. At least, I found my knowledge of competition carried me over quite well into the women’s world I was in. Of course, I needed to lose all my male privileges’ I had gained over the years and start all over again and often I learned the hard way that women compete just as hard as men. Just in different arenas.

Once I learned the new rules, I was learning quickly and even enjoying my feminine world even more than I thought I would. Probably because I was dealing from a position of gender strength because of all the time I had spent in a male world. Many times, I found I knew what potential problem would be coming at me before it even appeared. One of the gifts of being a transgender person.

Of course, now I feel that I have found much more than I had ever lost. I look back at my all too lengthy male life as the chance I had to learn the basic building blocks of life which I would need later to succeed at being a woman. From there I needed to take all the benefits I found as a new feminine person and use them wisely. To squander all that I had learned would have been a tragedy as I wasted all my time in the gender lost and found.

 

 

 

  


Innocent until Proven Guilty

  JJ Hart In many ways, this post is an extension of yesterday’s article. It involves the constant gender dance my second wife of twenty-fiv...