Showing posts with label relationships. Show all posts
Showing posts with label relationships. Show all posts

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.

 

  


Friday, October 17, 2025

Here Comes Tomorrow

 

My wife Liz, anniversary image.

Liz and I’s wedding anniversary was yesterday, and of course we had to go out and celebrate the event. It is actually our third anniversary after being together well over a decade.

Over the time I have written this blog, I hope I have not been short on trying to relay what my wife Liz has done for me. So much, as a matter of fact, she kicked me totally out of my closet, and showed me tomorrow was here. I could live a life as a transgender woman, finally free from my old male self. She was the direct opposite from my second wife who kept telling me there was no way she wanted to live with another woman. Liz told me she saw no male in me at all, and the rush was on to complete my male to female transition.

By the time all of this happened, and my second wife passed away, I was well into my sixties and had given up any hope of ever finding another serious relationship. Preferably with another woman who would accept me. As I always point out, to combat my severe loneliness, I was working the bar scene and even tried online dating which turned out to be a joke…until I met Liz. Or she met me. She responded to a “woman seeking woman” ad I put on a dating site and as luck would have it, she lived relatively close to me in Cincinnati. At the time she commented on the picture I used, saying I had sad eyes. Which I did, seeing as how I was going through the toughest time of my life. I had just lost my wife of twenty-five years as well as nearly all of the close friends I had to death as well as losing my business. I was grasping at any straw I could to stay afloat, sad eyes or not.

The only main straw I had was my sudden dependence on my strong inner feminine self. In a time of darkness, when my male self-had deserted me, she stepped up to provide the comfort and strength to move on. It was up to her to carve out a new life with new friends who had no previous contact at all with my old male self. Against all odds, in a sometimes-hostile world, she managed to do it, and my life slowly began to improve. With all the help and attention, I was receiving from my new ciswomen friends, I did not have to even give much of a second thought to the men who were afraid to approach me or just wanted to treat me as some sort of a fetish object. With my base sexuality settled again, it made it easier to feel secure in myself and move on with my male to female transition. Often it seemed my life was coming full circle and Liz was a major part of it.

During our anniversary dinner last night, we were fortunate that the venue was very empty without even the usual screaming kids so we could reminisce about our past and dream about the future. And of course, Liz took all the credit (as she always does) for reaching out to me first as a “woman seeking woman” post was an exceedingly rare response coming from any other women in those days. Plus, I was not shy in pointing out I was a transgender woman made my odds even more remote. If I received any responses at all, I felt like I had won the lottery of dating as a trans woman.

Because of Liz, I won the lottery for all the reasons I went into and more importantly, my gender transition which was always tomorrow became today. It was time to give away my remaining male clothes and follow Liz’s instructions on following my heart. A heart, it turned out, was feminine to start with and needed little to no encouragement to live. Regardless, when tomorrow finally came, it hit me hard and I needed time to adjust I really did not have. I needed to fall back on the decades of cross-dressing practice I had to feel more comfortable in the world. When I did, the joy of life I experienced was wonderful and even more so because I had someone special to share it with.

To be able to live the way I do still feels like a dream to me and Liz has helped me to realize my transfeminine dream more than anybody else ever did in my previous life.

Happy anniversary Liz and may we be able to celebrate many more together. And, thanks to all of you who have joined me in my journey. If you have not reached your tomorrow yet, keep trying. I am living proof it can still happen.

 

Tuesday, February 14, 2023

Happy Transgender Valentines Day

 

From the Jessie Hart Archives
my Valentine Wife Liz on left,


This Valentines Day I have decided to write about  loves I experienced during my life. I have been fortunate in that I have always had a cis woman who more or less put up with me. In chronological order, here they are.

The only woman who did not know I was at the least a cross dresser when we met and dated was my first fiancĂ©. She ultimately became the only woman to ever attempted to completely dress me up as a woman from head to toe. As exciting as it was for me initially, the newness wore off and problems set in. I can't say my cross dressing led to our ultimate separation before I enlisted in the Army. During my interaction with the military draft board, she told me to tell them I was gay to get out of serving to stay home. If I didn't, she told me she would be done with me. When I refused, she followed through on her threat and I was done with her which was probably the best thing that had happened to me to that point in my life.  I was now on my own when I went off to Army basic training at Ft. Knox, Kentucky.

Ironically, my second big romance came courtesy of the Army in Germany. Once I was there for awhile during my two year tour, I met a WAC. Known back then as the Woman's Army Corps. We started to date to the point we decided to keep seeing each other after we were discharged from the military. She knew I was a cross dresser from the beginning of our relationship so I didn't have to worry about telling her my innermost secret. To make a long story short, we ended up getting along well enough to get married and she gave birth to my daughter. Who turned out to be my only child.  The relationship lasted nearly five years until I was literally knocked over when I met my wife to be of twenty five years. It was love at first sight and somehow, someway I knew I just had to establish a relationship with her.

After a lengthy courtship behind my first wife's back, I managed to win her over. Even when I told her I was a cross dresser also. I can't say the twenty five years were not at times rocky but for the most part they were interesting. Even though she fought completely any thoughts I was transgender, I still loved her dearly until her completely surprise death at the age of fifty from a massive heart attack. I was destroyed for years.

I was still very much dealing with a possible transgender transition when I met Liz and several others who helped me more than they ever knew. It has been over eleven years ago since Liz and I met and we were married last October at the urging of my daughter. Just one of the major things I remember about our relationship over the years was when Liz told me she had never seen anything but female in me.

Over the years of my life I have been fortunate to have been loved and to love several Valentine's which passed through. Perhaps being transgender made the process a little different of course I can't speak for others. But since I came from a family who wasn't known to show emotions and even speak of love, being transgender or not has made the love experience special to me.

Happy Valentine's Day to all of you also and thanks for reading along.  

  

Saturday, November 5, 2022

A Transgender Friend

 Do you have any transgender friends? I myself have many transgender acquaintances but not many I would consider to be friends. Perhaps the entire process is a holdover from my previous male life when I could count the friends I had on one hand. Along the way, right or wrong, I learned to shield myself from other persons. I was good at flirting with women and acting as if I was macho with other men. As I wrote, most of this carried over when I began my gender transition. 

Photo Courtesy 
Racquel

Along the way, I did have a transgender woman (left) acquaintance whom I called a friend. Since that time years ago we went on our very separate ways. She is much younger than I and underwent several body changing operations while I forged forward making the best of what I had. She is the one who told me I passed in the public eye out of sheer willpower. 

Maybe I am too demanding when it comes to expecting friendship to develop from just being an acquaintance. After all, just being transgender is a wonderful starting point to knowing another person. But then again, the transgender community is so segmented it's no wonder many of us struggle to gain what we call a true transgender friend. One problem is when certain social media platforms encourage you to gather an immense number of "friends" . Most of them you have no chance of ever meeting. 

Closer to home, I am fortunate to be able to live close to a fairly large metropolitan area with several well developed LGBTQ organizations. At the least the organizations give transgender women, trans men and even allies/spouses a chance to get together to discuss issues. For others in mostly rural areas, social interaction is limited to on line meetings. Sadly, I notice many of these on line relationships to be extremely limited in duration.

In transition, so many of us lose access to our previous access to friends and family, we become desperately lonely. Too many often fall prey to on line scammers, promising much and delivering heartache. Desperation runs rampant with many transgender people who are seriously lonely.

Finding a true transgender friend has been difficult for me. Mainly because I don't socialize much anymore and I was able to find and hang out with cis women friends as I transitioned. Before that time I could safely say I was a part of the seriously lonely portion of the community. Plus, how I made my way to freedom was one I would not necessarily recommend to others. My salvation involved plenty of alcohol and taking too many ill advised chances on social media. Before I happened upon the friends (yes I said friends) who helped me out of my social funk, I went through many times I was out and out gas lit when it came to a potential date. It's one of many reasons, I cherish the friends I made then to this day.

On the other hand, I know more than several transgender women and men I deeply respect. Even still, I hold out a precious few people I count as friends.  

Gender Hide and Seek

  Image from UnSplash On occasion, I look back at my decades long journey to live as I really wanted to live as a transgender woman as a ro...