Wednesday, June 24, 2026

What is a New Trans Girl to Do?

 

Image from UnSplash. 

I recently received a comment from “Mira” concerning writing more about what happens when you are a new transgender woman out in the world.

Thanks for the comment, “Mira”, on such a complex subject. The first thing I can think of being so different for me was that everyone was looking at me. As a man, I was used to admiring well dressed and attractive women but got used to the fact that I was nearly invisible to the world as a guy. In essence, other women and men all notice other ciswomen who go out of their way to at least look nice. Which was what I was doing when I went out in the public’s eye to see how well I could present myself as a transfeminine person.

Maybe the most important hurdle I faced at this time on my gender path was looking like I was trying too hard to look like a woman. The initial attempts I tried to make such as wearing too tight and short skirts, produced laughable results when I was laughed at in reality.  On the other hand, you need to take an accurate assessment of your basic strengths and weaknesses and go from there. I know you may think you may have very few strengths when you are trying to dress your testosterone poisoned body, but you may be surprised. Many men are blessed with passable looking feminine legs, which is a place to start building your presentation from. I learned my legs were good from the Halloween parties I went to in my mini dresses. So at least, I had a positive place to start from when I began to go out. Until I began to overdo it and feature my legs over my biggest fashion problem…my broad torso and shoulders. I still wore my denim miniskirts but with large flowing tops which were able to hide my shoulders as I got by.

The difficult part for me was getting any realistic feedback from anyone. The only feedback I received on a regular basis was from my mirror which I found had a habit of lying to me and from my wife who would dismiss me as only being the “pretty, pretty princess.” I did not want to be a princess; I just wanted to present as well as I could in the world as a transgender woman. I understand now what my wife was trying to tell me about being feminine would take more effort than just looking like a ciswoman and I would have a long way to go.

The next big step I took as a novice transgender woman was to not be afraid when someone wanted to know more about me and I don’t mean in a close, personal sense. As most of the many ciswomen I encountered just wanted to sell me something (clothing store clerks) or were just curious about what I was doing in their world. Once they were satisfied, I was not up to no good and I just wanted to be part of the girls’ club, they were happy and went on their way. Except for a few who stuck around and I was able to make friends with. Which came much later in my trans life when I grew more comfortable in my new skin. And speaking of skin, if you are overweight, consider going on a serious diet like I did to slim down and look better in more stylish clothes.

When you are new to all of this, it is easy to feel selfish when you are obsessed with how you look and act as you try to determine if you truly belong in the new world you are exploring. All of that is a natural reaction to letting go of the male world (or female world for you trans men) that you had to work so hard to survive in. Often against your will. Plus, learning all the nuances of a new gender is not and never will be easy. Especially if you transition later in life such as I did. The reality of the situation is that you have accumulated much more gender baggage to deal with over the years, and you must start deciding early on what you are going to do with it.

Backtracking a bit, what I remember the most about my early years as a transfeminine person was the panic I felt when I entered the world for the first time. Mainly because I had lost all the defense mechanisms I learned as a man. I could no longer rely on my size in a potential problem situation or my intelligence to win a discussion. My best offense in the new world I wanted to be in was to plan ahead and do what ciswomen do, not get into the situation to begin with. As far as intelligence goes, just plan on losing yours if and when you encounter a serious discussion with a man.

As you walk up your gender path as a new trans woman, validation as a person becomes a valued piece of your new personality. In my case, I was never attractive or interested in men enough for them to be in my world, so my validation had to come where it had always come from in my life, from other women. When I see many of the transgender women bemoaning the fact they don’t have a man, I always say, don’t overlook having a woman love and validate you. Always leave your future options open because anything can change in your life when you are trying to cross the gender border.

Finally, “Mira”, try to develop a thick skin and learn from your possible presentation mistakes when you begin to go out. Especially today with many areas of society being so volatile when it comes to trans women and trans men. When you are a quick gender learner, your life can come together faster than you ever thought. Be prepared, it could be an interesting one. Stay safe and thanks again for the comment and I hope that I have answered most of your question.

 

 

 

 

Tuesday, June 23, 2026

I Wish I Knew Why

 

Image from Anderson Rian
on UnSplash.

It is not like I am new to being out in the world as my authentic feminine self, so I don’t know why I feel certain ways.

One of them happened this morning when I needed to take our car to the shop to get the oil changed before we take a rather lengthy trip to my old hometown later this week. As I have written before, I am still fearful of going by myself to any male dominated businesses.

I think it goes all the way back to when I was a kid when I used to go with my dad to an auto parts business a friend of his owned. There were never any women, and I felt totally out of place. At the time, I felt it was because I was young at the time and I would grow out of feeling self-conscious there. But now I think, it could have been my inner female rebelling at the ideas of being around all that intense masculinity.

Back to this morning, even though I did get an early start, I wanted to be there when they opened at 7:30 AM to get my paranoia over with. I was worried since we are headed into a holiday weekend, they would be busier than they were. Which was a moot point, since I had to figure out what I was going to wear, shave, put on my light makeup and head out the door. After doing all of that, I was still out the door by eight and still was able to get right into the oil change location.

Since I would not be getting out of the car for either of the places I could go ultra casual and wear my jeans along with my “Libra” themed burgundy tank top which I wear with my long hair pulled back so it softly falls over my shoulders which is my revenge for having to cut my hair extremely short when I was young and even later when I was in the Army. I am very fortunate in that I have never had any male pattern baldness, so I have always had a great head of hair.

It turns out all my paranoia was unfounded as none of the male workers did anything out of their way to make fun of me and were professional in every way. Before I knew it, I was on my way and breathing normally again. On my way to my nest stop at my wife’s Liz and I’s favorite coffee shop to pick up coffee and a light breakfast. Other than having coffee and food we like, the coffee shop also has a LGBTQA+ flag proudly on one of their walls. Again, the person who served me was very nice and put me at ease.

On the way home, during my short trip trying out the world again as an independent transgender woman, I was wondering if changing my estrogen HRT patches out today had anything to do with my moodiness about going out in the world alone. Friday, when I make a much longer trip back to my old hometown, Liz will be going with me as I must pick up more copies of my name change documents from all the way back to 2015.

Sadly, I have more negative memories of my hometown than good ones, but I need the legal copy with the judge’s signature on it for a life insurance policy I forgot so long ago. I can procrastinate with the best of them!

To make a small joke about my visit to have the oil changed this morning is that all my fluid levels turned out to be OK. Maybe the true win was to realize what the basic reason I still fear going into male dominated spaces so badly. It is a deep-seated problem which goes back to my youth which makes it very difficult to get rid of.

 

 

 

Monday, June 22, 2026

Gender is a BIG Deal

 

Image from Dwayne Joe
on UnSplash.

Gender is a huge deal in our society in America and around the world. You can’t go for a minute on the news or social media without someone pointing out how powerful their gender is.

Plus, just consider how many “gender reveal” parties that are going on these days before the child has a chance to choose for themselves. And I won’t even get into intersex children which have to with whatever a doctor decides about their ambiguous gender at birth. How confusing can that be to overcome later in life.

Regardless, gender is a big deal. We are expected to abide by the results of what our genitals are telling us. Not regarding at all what our minds are screaming at us, that something is certainly wrong with what we are being told. For me, it was being shoved into a dark hole with no way out. Mainly because I was born as the eldest son into a very male dominated extended family where women ruled from behind their men. Maybe that is where I learned the hard way on my own, what it meant to be a strong ciswoman. In her own way, mom held the family together in many ways that dad did not as for years, he was busy being the main provider in the family. Leaving me to wonder what I could ever do to follow in her footsteps.

It took me years of experience of being a cross-dresser, then a transwoman to decide which direction my life should take me. Towards the masculine side I was born into, or the feminine side which I kept leaning towards in so many ways. My male gender kept pulling me back to a life which I had become comfortable in and just did not want to let go. More precisely, it took me five decades of searching to finally decide which life I wanted to lead. The one I was currently comfortable in, or the new exciting life I felt so natural living. A homecoming of sorts.

I write often of my experimental gender years when I did my best to learn if I entered the world of ciswomen for good. Since I did not have the feminine upbringing, they did, I had many surprises. Some good, some bad but the bad ones brought with them an opportunity to improve. That was when I found how big of a deal gender was with some people while others just seemed to take it for granted. Such as the gender haters such as TERFS who women who fanatically guard their femininity like some sort of mean gatekeepers who want to keep all transgender women out. Fortunately, in my life, I have only encountered evil TERFS who resented me for just wanting to cross the gender border and live as a transfeminine person. I learned to ignore them and they eventually went away and left me alone.

Then, we cannot ignore the effect of the ultra-masculine and feminine athletes of the world have on the youth they have looking up to them all the time. It is more apparent during Pride month when baseball teams attempt to honor their LGBTQIA+ fans by wearing rainbow themed uniforms and some teams protest.  Can you imagine that happening in the National Football League where over the years, only a few players have come out as gay. Percentages dictate there are more (even transgender players) who are still in their closets in the NFL. Whatever the case, it is obvious gender worship overcomes hero worship most of the time with young fans. At least with the lucky fans who do not have any gender issue problems like I did when I was young. I knew I could never play professional football but as a fallback, could I ever become the woman I dreamed of.

As I continued to attempt to find my way in a new world, I did not know how many stop signs I would encounter. First of all, how I looked then as I improved my feminine presentation, what was I going to do about how I was moving about and communicating with the world. All the way to using the restroom of my choice (women’s). Sure, I was scared to enter women only spaces, but I learned through careful observation that I could use the restroom I wanted to if I was careful to follow all the rules. Which I could write a whole other post about. To put it briefly, the greatest majority of ciswomen I faced in the restroom were just there to do what I was doing, and it was no big deal. They were just going where their gender had always told them to go. I had never had that luxury, so I needed to learn what they had always known. My gender workbook had no chapters on using women’s only spaces.

It was also important for me to get out of the gay venues I was always going to and test the world one on one as myself. There was no way to tell if I could ever be successful as the person I dreamed of if I was always only perceived as a drag queen. I knew it would be difficult for me to be mistaken for a ciswoman in society, but I hoped I could make it as a successful transfeminine person just getting by in the world. The more I lived in this new world, the more I knew how big a deal it was to me and I tried even harder. Mainly to become the friendly outgoing woman I always wanted to be. Going back to my young male days.

I discovered too that I had a huge sense of accomplishment when I was able to carve out a new life for myself. Mainly in the straight venues of the world, I used to frequent often when I was a man. It was all I could ever ask for and so much more.

Gender turned out to be the biggest deal of my life.

 

 

Sunday, June 21, 2026

In the Wrong Room

 

JJ Hart

The first time I realized I was in the wrong room was when I was out as my transfeminine self in one of my regular venues when somehow, I found myself with a group of four men. Let me preface my thoughts by telling you the men were just having typical men type discussions on sports and work and no one was a rocket scientist.

Very quickly, after I was made to feel below their dignity to even acknowledge me, I went away with my first lesson learned. Stay out of male conversations unless invited, and even then, don’t expect your opinion to count for much. It seemed I had entered a place where my impostor syndrome was replaced by out and out rejection. I wasn’t worried about being in a group of ciswomen being worried about what to say and do, to entering a place where I was not wanted at all. I just can tell you this, I was never treated rudely by the women I faced in my first girl’s nights out as I was during my impromptu meetings with men. Which helped me to understand I was headed in the right direction on my gender path.

It could be too, that I did not give men a fair break. I was not attractive enough to be desirable, and I had not developed any sort of personality, yet which gave me any other positive characteristics. In other words, I was still an unsure new trans woman who had just left the men’s club, and it showed. At least to a transgender man who asked me out to a dinner date and later he said I was scared and nervous on our date. He was right, and I was just going through being in the wrong room as myself.

Fortunately, that feeling of being in the wrong room did not last long as I grew more adjusted to my new life as a transfeminine person. My inner self kept telling me I was in the right room at the right time as I felt natural doing it. As we all know, confidence plays a huge part in being successful as transgender women and transgender men and when I gained the confidence, I needed to say to the world who I was, there was no turning back. The more I accomplished in my new life, the more I realized that my male life was living a lie. The problem was that just deciding I was not going to live that lie any longer was not going to be as simple as just doing it. Because I had accumulated so much male baggage along the way as I fought to succeed in a world I never really wanted.

Even though I was fighting to switch rooms, the battle was never easy because of the major roadblocks which were in my way. Primarily, the roadblocks came from my second wife who was struggling to maintain her marriage to a man who did not want to be one and my male self who was fighting for his total existence. To make matters worse, my life as a man was not that bad all of the time, so the gender decisions I needed to make were so much more brutal in nature.

When I finally found myself in the right room as a trans woman, I found I needed to furnish it into what I needed to live. It was totally barren of anything I would need to live successfully, and I had to start by doing the best I could to present well as a woman and then learn the basics of survival in a world run by ciswomen. It was their room I was trying to be given admission to but not before I earned my way in.

That was when I needed to take a deep dive into myself and produce more of a one-sided effort to do something than I had ever tried before. Always before, when I was trying something new, I would get discouraged and quit, but this time I could just not and kept trying because I knew my dream of living as a transgender woman was certainly achievable. Before I did, I needed to somehow be allowed into other women’s lives and rooms to see how they lived. I was especially interested in the women who were not especially attractive because they showed me the importance looks do not have to play in a woman’s life. There were plenty of other things in a ciswoman’s multi-layered life to concentrate on other than beauty.

Since I lacked beauty, I needed to decorate my room with it, I needed to seek out other ways to do it. Such as was I treating other women the way I wanted to be treated became a main goal. A smile took me so much farther than my old male scowl designed to keep people away that I could not believe it.

Once I learned the difficult lessons of feminine decoration, I no longer had any vestiges of being in the wrong room. In fact, the deep belief that I was in the right room kept me going through out the trying times of legal name changes to the fun times of HRT therapy which sent me into the second puberty of my life. It turned out, it was the one my body was always waiting for.

Rooms are always difficult to plan for as you decorate a new one. Especially if your gender workbook is blank and you are struggling to catch up. The paintings on my walls were of my friends who showed me the way as well as my wife Liz and daughter who finally kicked me out of my old room and into a bright new one. As you can tell, they all mean so much to me.

As all of you do who follow along with my experiences and daily goals on a regular basis. Without you all, everything I do would be worthless, so thank you! And I hope the room that you are in is not a closet you are trying to find your way out of. Hopefully, you can do it soon.

 

 

 

 

Saturday, June 20, 2026

Memories or a Dream?

Image from Ian Dooley
on UnSplash

Too many times, when I went out into the world for the first time as a new transgender woman, I wondered if I was making a memory or living a dream.

Sadly, most of the time I was working so hard to succeed for the first time in a new exciting world, I did not have the time to know if I was making memories or working my way towards a lifetime dream. There was simply not enough time to do all I wanted to do, such as present well enough to blend in with the ciswomen around me. It was like I was driving a new car, and I did not know all the new features I was trying to master. How was I ever going to stop being a man with all the male looks such as a scowl and how I walked and turn myself into a pleasant looking feminine person as I camouflaged all the testosterone damages male puberty had caused me.

There turned out to be a way after I worked my way through not dressing like a teen girl which just drew negative attention to me. Certainly, creating more negative memories than positive ones and my dream of living as a full-time transfeminine person, remained just that. A far-off dream. At first, I had many memories to make and learn from as I followed my dark and lonely gender path. Perhaps my biggest problems came when I realized I was trying too hard when it came to expressing my own brand of feminization because I was working so hard to catch up with my own gender workbook and decide where I wanted to be.

The only dreams I was having during this time of my life were the rare occasions when I went to sleep and dreamed that I was the attractive woman I always wanted to be and the pressure was off to look a certain way as a woman which I had always lived with. I was obsessed with trying to try any beauty secret I could to improve my appearance in the world. This obsession very much was with me until I began to settle into my own beauty routine

 The dream took a giant step towards materializing when my daughter took me to her up-scale beauty/salon and spa to color and style my hair for the first time when it had grown long enough to do it. Even though I was scared beyond belief to do it, I knew this was a golden opportunity to go behind the gender curtain into a female dominated space I had never dreamed of going before. It was amazing as I wrote about several posts ago, and I knew right then why ciswomen were so adamant about having their hair done a certain way. I could not wait until I could scrape up the extra money so I could afford to go back. Plus, with my new hair, there was no way I could keep on presenting male in the world as I knew it.

I was so obsessed with putting myself out into the world, I needed to think of different ways to do it and build more memories such as when I started to meet the ciswomen and lesbians who would form my circle of friends and help me slip across the gender border and behind the gender curtain where I desperately dreamed of being.

At this point, I always mention the good and the bad that happened to me along the way to validating myself as a transgender woman. It took a lot of confidence I didn’t have to make it happen. Too many nights of rejection when I attempted to push the gender envelope too far and was sent home in tears with my new dreams shattered. When it did happen, I needed to rely on my deepest inner feminine self to assure me everything would be OK and these were just memories which happened to be unpleasant to add to my dream. She told me that the roughest dreams you ever had are the ones you had to work extra hard to achieve.

Sooner more than later, I began to have more pleasant memories than bad ones and my ultimate dream again began to come into focus. If I tried hard enough to accomplish all my feminine goals, I could join the others ahead of me in the transgender community I was familiar with and leave my male past behind me forever.

Surely, there is a big difference between memories and dreams. I consider memories a less than physical form of dreams. Meaning memories are easier to come by and dreams are something a human should always have to keep their lives headed in a more positive direction.

Depending upon where you are on your gender path, maybe you are just in the dream phase of where you want to be and that is fine. It is when you begin to build memories of your journey do you start to build the blocks you will need to make it through. During Pride month, no matter what you may read from haters, TERF’s and bigots, you should be proud of the gender dreams you have.

You are worth it and often there are more silent allies and developing transgender women and transgender men that you know who are ready to join society. Just look at your memories and dreams as what you had to go through to arrive where you are today. Someday you may be able to become that confident trans woman you only were when you were asleep.

When it comes right down to it, it does not matter if you are clinging to memories (past and present you are making) or the life you are dreaming of living, The most important thing is the self-love you are able to give yourself. Without it, you have a difficult time loving anyone else.

Thanks for reading along with me and thinking of your own memories and dreams. Any of your comments are always appreciated!

 


Friday, June 19, 2026

A Lifetime or First Times as a Trans Woman

 

Image from Mahreal Boutrous
on UnSplash. 

As humans, I know we all experience quite a few first times in our lives. However, I think transgender women and transgender men tend to have more firsts than the average human.

During my life, every time I thought I had it together and there was nothing else to learn, along came something totally different to prove to me I still had a lot to prove to get to the next level of life I was trying to reach. This happened to me as a man and as a woman. My prime example was when I was in my twenties and totally out of control trying to drink my gender issues away and my daughter came along. Causing me to change my thinking about life radically because having a child was not something that I had planned on. Let’s just say the “protection” gave out and here she was. My very own daughter that I loved and love very much.

The initial problem I had as a first-time parent was what I was going to do about my gender issues which were increasingly looking like they were not going away, ever. What did I do? I tried to hide my femininity behind a wall of false male bravado which as we all know was a short-term solution to a long-term problem. So, I needed to set out to discover how long term my “problem” was.

Using a well-known phrase that I learned at one of the places I worked at, I did not have a problem. I had an opportunity to improve. To do it I would have to have the courage to take a different approach to life which would include a series of first times. The courage I am referring to was when I hitched up my new big girl panties and went out into the world for the first time as a novice cross-dresser or transgender woman searching for her identity. In those days, my first times were filled with rejection in the public’s eye and plenty of disappointment to deal with until I understood what it would take for me to present well enough to get by in the world of ciswomen that for the first time I learned really ran the world I wanted to be a part of. If I wasn’t attempting to be validated as a trans woman by men, first I needed to be validated by women.

Once I broke limits of what I was trying to accomplish in the world as a transfeminine person, the challenges and first times came quickly rolling in. The opportunity I had was trying to understand how deep my gender urges ran or how badly did I want to sacrifice my male life and live as a woman. What I decided to do was undertake a deep dive into what I “thought” a ciswoman’s life was all about, and what it really was. And more importantly, could I ever be allowed behind the gender curtain to see for myself if I wanted to play in the girls’ sandbox.

For the most part, I was successful as I accomplished my lists of firsts such as taking feminine vocal lessons, all the way to attempting to carve out my own new life away from any vestiges of my old male existence, Often, my life was a blur as I tried to balance what was left of my male existence with my new exciting life as a trans woman. Not only did I have to do my best to blend in with other women physically in the world, now I had the extra pressure of communicating for the first not as a man, but woman to woman. The last thing I wanted to do was come off during my final test with a stranger as some sort of an evil bitch just because I did not want to talk.

For some reason, during this portion of my life I was not having any problems attracting attention from ciswomen. After a lifetime of basic rejection from women, I tried to reach as a man, all of a sudden for the first time, I was having success as my transfeminine self. Even though I did not completely understand what the reason was for my success, I did not want to jinx myself and do too much and go back to rejection and loneliness again. So, I kept up what I was doing and for the first time built a new base to my life.

I had two reasons for my success as I looked back on those days. The first was, my inner feminine self-had so long to sit back and observe what I was doing with our lives that she knew exactly what she wanted to do when she had a chance to run the show for the first time. And the second was told to me by a person much wiser than me long ago that very few human beings have the chance to stop their lives and begin again, so don’t screw it up if you do. I was able to listen to both.  

Sure, I went through two lifetimes of first times with all the bumps and bruises which normally come with such adventures. When I think back to all those early days in the malls when I was getting laughed at for my weak initial femininizing attempts, I don’t see how I made it at all. I guess something deep down inside of me kept telling me that this was just an example of the first times I would be facing my whole life if I continued along the gender path I was considering.

I was far from deciding if I could ever slide behind the gender curtain to learn if I really wanted to be there. But somehow, I knew I would never forgive myself if I did not try. When I did, for the first time I found myself off the self-destructive male path I was on and on to a rewarding and healing path I loved as a transgender woman.

 

 

Thursday, June 18, 2026

My Biggest "AHA" Moments

 

Image from Valentia Conde
on UnSplash.

During the long gender path which I have been fortunate to live, I have had many “aha” moments to look back on.

The problem I had was realizing that the times in my life were something I would forever remember, forget immediately, or just refuse to understand what they meant after my own ignorance set in. For my first example, I have to go way back to the first times I was exploring my mom’s clothes and makeup. I knew something was up, but I did not know exactly what and how deep it would run with me. All I knew was my desire to be feminine in any way was deeply forbidden in my family and most of society which called it being mentally ill at the time. Through it all, even though I did not fully understand what was going on with me, I did think I was mentally ill for thinking it.

That was the good news. The bad news was I was decades away from understanding the “aha” moment that I was living the wrong life as a man all along. Even if I was warned by a therapist that I respected very much that she could essentially do nothing about me wanting to be a woman and I was on my own to save a marriage that I really wanted to save. If I would have listened to her and started my male to female femininization earlier, I would have saved myself so much inner turmoil that it would have been amazing. But I did not and stubbornly hold on to the idea I could live as a man while at the same time cross-dress when ever I wanted as a woman.

Another problem was, I had moments when my feminine world was opening to me and I thought, “wow is that what being a woman was all about.” Like the day at the grocery store when I positively melted a young bagger who was stuttering as he shyly asked if he could take my groceries to the car. Right then I knew why I had such a difficult time talking to pretty girls in school when all my perceived smooth vocal abilities just disappeared. It was a giant “aha” moment when I had the chance to reverse course and cross that gender border so long ago.  

As I held on for dear life that I was just following my hobby as a cross-dresser, slowly but surely the idea of going through another male to female transition gained on me. I went back to the times when I was thinking that just putting on makeup and a dress was good enough. I always wanted to do more like the pretty girls around me did at school. I wanted to be the one being chased for a date in my new pretty clothes any time that I could. Which turned out to be never back then. Years flew by before they ever did as I began to test the world of ciswoman as a novice cross-dresser. Then, one night out of nowhere, the thought came to me that I was done just looking like a woman again, I wanted to inter-mix with them and see if I could be accepted. If I was, from that point forward I would change my self-gender perception from just being some sort of a harmless hobby to thinking about myself as a thriving transgender woman. A super scary, but exciting thought because once I went there and was successful, I could never go back to ever just thinking that I was just a man again. A real, enduring “aha” moment in my life.

The problem I had was once that I was becoming successful as a new transfeminine person, how could I stay there. Initially, I made up a new feminine persona to go with my new look. I wore the same wig and used my same new name every time I went out and before I knew it, I was being treated as a regular in all the venues I was testing out in the straight world I knew before as a man. Another big “aha” came when I was able to break the influence of all the gay venues I was going to which I really disliked and was accepted as me in a new world. Then I learned I could have fun doing it as I enjoyed my new feminine self so much that increasingly I did not want to go back at all to my old male world.

As I did, I began the all-important job of getting rid of all the male baggage I did not want or need anymore. At all costs, I hoped I could maintain a relationship with my daughter which I did, and if my brother did not accept me, so what. Which he didn’t and we went our separate ways as those two were the only two blood family that I had left. With all of that turmoil behind me, I was free to concentrate on my transgender future which did not include any surgeries at my age of sixty, but hopefully a chance to test out my body on HRT or gender affirming hormones. I was approved first by a doctor and then by the Veteran’s Administration to begin the hormonal treatment and positively loved it. It was as if my body was saying the hormones were an “aha” moment and were the missing ingredient to leading a fuller transfeminine life.

I am sure there were other “aha” moments which turned out to be bright light posts on my often dark and lonely gender path. Such as when my current wife Liz came into my life to love me and make me whole again by saying that she had never seen any male in me. I never realized that I had built up that much good karma to help my life along.

Thanks for reading my lifetime of gender experiences as a transgender woman. Hopefully, you can gain some insight to help you along.

 

Wednesday, June 17, 2026

Living the Dream before it Consumed Me

 

JJ Hart

As I crossed the six-decades portion of my life and spent at least five decades of it trying to stay under control by cross-dressing, I was trapped and had nowhere else to go.

It happened because I had embarked on such a complete path of looking like and moving like a ciswoman and my gender bucket list was shrinking due to too much use. All the trips to malls, antique stores, and thrift stores just became boring when I was passing through them with no problems. Even though I was bored, the idea of being successful as a transfeminine person still consumed me. And, to make matters worse, I was finding less challenges to undertake as I increasingly painted myself into a gender corner I had always dreamed about but never thought I could reach.

I always made excuses such as I was never going to be good looking enough to present well in the new world I was seeking when truthfully my overall confidence as a trans woman had more to do with my approval than my appearance ever did once I had went beyond the basic point I needed to be to blend in with the ciswomen around me. Life changed when I realized there were plenty of women in the world who dealt with being bigger in stature and even had broad shoulders such as I had. My realizations helped to give me the boost I needed to continue to let my so called “hobby” consume me.

The reason was that I was ignoring the fact that cross-dressing was much more than a hobby, it was becoming a lifestyle. The biggest problem was that nothing I did as a novice trans woman was ever good enough. Even my second wife did not like the person I was becoming when I took the time and effort to show off to her as I thought were my best feminine efforts. Even though I desperately was seeking her approval, it was becoming obvious to me that my inner feminine self and my wife were lining up to fight it out. I was left behind to pick up the pieces as I was realizing how consumed I was when I had one of my rare, sanctioned (by my wife) outings at Halloween in NYC when my wife decided she did not want to go with me. The night turned out to be a dream evening as I ended up going out with four other women dressed to thrill as I was and they all happened to be as tall as I was in our heels. The night even ended on a high note when I was asked to dance by a guy in the venue we went to. I turned him down because he had no idea that I had one basic difference from the other woman I came with.

Anytime I experienced such a wonderful evening such as that Halloween party, I wondered if the gender euphoria I felt was worth it when I came crashing down. I was consumed with the moment and wanted to re-live it time and time again, but I was tucked away in my male work world and could not get out. Looking back, I don’t see now how I survived the balancing act I was putting myself through. I needed to physically show up as the man I never wanted to be. While at the same time spend all my mental energy remembering the transgender woman, I was. If I could have cried during that time in my life, I am sure I would have cried myself to sleep many nights worrying about my gender dysphoria and how it always threatened to wreck my life. Even to the point of almost destroying my marriage to the woman I loved deeply when my frustrations would boil over into yet another fight about me. Some of the fights were so severe that my second wife told me I was not man enough to be a woman, or why didn’t I just go away and fix the problem and make both of us happier.

Perhaps, by this time, you are wondering too why I did not take her advice and do it. The main reason was, at that time, I was not ready to give up totally on the life we had together when I was a man and even though I was increasingly being consumed by the idea I could be the trans woman I always dreamed of, I was not ready to pull the cord and jump out of the plane just yet. Because I was still afraid of the new gender heights I was reaching and selfish enough to think my wife may still come around to accept me. For those of you who don’t know, she never did and died tragically of a massive heart attack at the age of fifty.

The whole experience sent me into a major negative tailspin which I had a difficult time emerging from. I think the only reason that I did was because I had let my feminine self-consume me, and she could not wait for the opportunity to take over and live. My life had come full circle, and all the time and effort I put into my male to female femininization came back to help me. I had already put the work into how I wanted to look with my make-up and fashion basics and was already out into the world actually discovering how it would be to carve out a new transfeminine life for my very own. I had gotten what I needed as I moved ahead towards beginning HRT or gender affirming hormones. Which were something I always wanted to try as part of my overall commitment to being as close as possible to being who I always was destined to be.

When life consumed me, I was always somehow able to accept it and even thrive with it. Even though it took me decades to do it with all the ups and downs of what I had to go through. At the least, it made life interesting.

 

Tuesday, June 16, 2026

So Many Ways to Come Out

 

Image from Nicola Dowie
on UnSplash.

Recently, I had a response from a young transgender man on how he should attempt to come out to the world.

First of all, thanks for the comment and yes there are many ways to leave your closet and enter the world of the gender you are trying to live among. I know too that I have many trans men who stop by and read my comments which flatters me because as we flip the gender script, often the worlds we must conquer are not that different. Gaining the female or male privileges when you feminize or masculinize yourself often are the biggest issues. After you come out to spouses and family.

Over the years, I have read about coming outs that have ranged from just showing up cross-dressed as your authentic self, all the way to writing letters trying to explain the way you feel. As far as I am concerned, just all of a sudden showing up as a woman (or a man) has too much of a shock value and is counterproductive when you are trying to explain how you want to live to the person sitting across from you. Writing a letter may be more preferable if you feel more comfortable expressing yourself with written words rather than speaking one on one with someone. In my case, even though I did not feel comfortable talking to family about my upcoming changes, I hitched up my new big girl panties (under my male clothes) and asked to speak privately with those family members closest to me.  My first attempt at coming out was with my only child, a daughter and as I always write about, she took it extremely well. Just to show me life could never be that easy, my coming out to my only brother went off the rails quickly and we have not spoken since about 2014.

Having said that, I do caution trans women and trans men who are just coming out to family and loved ones that you are in a marathon not a race and sooner more than later, your family might come around. Plus, there is an increasing amount of information available now to explain your desire to live as yourself. If you have the chance, you maybe able to direct them towards the positive aspect of what you are doing and away from all the negative news they may see from politicians on the media ads. In my case, the split between my brother and I ran so deep when he refused to stand up for me and invite me to our family’s traditional Thanksgiving Dinner, I just can’t forgive him for that.

On the positive side, the relatively few people who knew the former me notice almost immediately that I am happier now. And if you give someone the chance to calm down and see the real you, they will respect that and the real you.

Of course, as we flip back to the negative side, there are always those family members that will try to throw religion in your face. Unless you are more of a biblical scholar than I am, I usually just give up on them.

Overall, I find the different sides of transitioning between transgender women and transgender men to be interesting. Since I was raised around the male dominated world of trying to force my way through difficult situations, I never gave much thought to trans men having to adjust to not being passive aggressive so much. Then there is always the idea of using the restroom which hangs over both of us. Even though trans men are in a new world in a men’s room where no one wants to make eye contact or speak, there is always the idea of having to still find a stall to use. Which conceivably could attract unwanted attention depending upon how well you present and how long you have been on testosterone. I know I have oversimplified the men’s room process and if you are a trans man, I am always up for ideas on restroom survival.

Flipping the script again, using the women’s room as a trans woman is something I know quite a bit about. The first thing I quickly learned was I needed to make contact and speak when someone else was in “the room.” From there, much of what I learned was either common sense such as never placing my purse on the floor and making sure my stall still had toilet paper all the way to trying to pee in the bowl a certain way to mimic the ciswoman in the stall next to me. Then, no matter how much I was in a hurry to leave, I had to always stop at a sink, check my face and always wash my hands.

Anyway, you cut it, when you have desire to cross the gender border either way from male to female or female to male, you must learn so many nuances of the moves you are making. Even though there are strict rules you need to follow, often times you will find yourself making up your own rules as you go along. It is just the nature of the ultra-serious game we play. What has worked for me in the past may not work for you and often I hear from readers who have supporters and non-supporters in the same family. The only advice I can offer is to embrace your new gender allies and hope your detractors come around.

The end result always must be it is your life to live and you need to live it to be happy. Sometimes your path will lead you the wrong way, just like your GPS does on occasion but it is not time to panic until you can get readjusted. Be patient, and it will happen.

As always, thank you for the comments I receive, often they are difficult to answer seeing as how we dealt with such a complex issue such as gender. I just hope, in my small way I can help.

 

 

What is a New Trans Girl to Do?

  Image from UnSplash.  I recently received a comment from “Mira” concerning writing more about what happens when you are a new transgender ...