Showing posts with label gender path. Show all posts
Showing posts with label gender path. Show all posts

Saturday, April 11, 2026

Your Gender Path maybe Different Than Mine

Image from Erik Mclean
on UnSplash. 
 

Even though many of us share similar paths to our dreams of becoming successful transgender women or transgender men, often our paths diverge and we end up going different directions.

Most of us start out on our own without the help
of an understanding sister or mother and must fill out our gender workbooks as we go along. There is no one to tell us what to wear or how to act in our younger years as a cross-dresser. We just know we have conflicting ideas on what we are doing. On one hand, we cannot wait to put on the pretty dresses we found that still fit us, but on the other hand, we felt guilty doing it. It was somehow taking away what was left of our fragile masculinity.

At that point, most of us were willing to sacrifice that masculinity for the intensely intoxicating appeal of looking at ourselves as pretty girls, especially before puberty got ahold of us and testosterone poisoning set in. We all know what happened then, our bodies grew angles instead of the curves we admired on the girls around us and life would never be the same again. From that point forward, many of our paths seem to diverge. Over the years, I have heard from several readers who put down their urges to be feminine with no problems until much later in life. While others followed a more focused stairstep path which meant meeting and learning from other cross-dressers or transgender women searching for their true meaning to life. I know when I first discovered there were others like me who shared gender issues and I could go meet them; there were many layers of people who attended the socials. Anyone from cigar smoking men in dresses still going overboard to preserve their masculinity to completely femininized transsexual women whose next stop was gender surgeries.

It was then that I began to see and appreciate the different layers of the gender community I was seeing in person for the first time. I could almost compare it to the amazing number of cosmetics I saw the first time I went shopping with my own money to buy my own. The entire idea of going to a mixer of my peers did not work for me at all. I became more confused about where I fit in on the gender spectrum than when I started. I knew I was much more than a part-time cross-dresser but was not committed enough to consider complicated and expensive gender realignment surgeries which were still fairly rare back in those days. The direction I decided to take was one of experimentation which I found set me apart from many of the other gender conflicted individuals I had met.

I certainly would not recommend the direction I took because it involved a certain amount of risk and way too much alcohol in the mostly gay venues I initially was going to. What happened was, I used the fake courage of the alcohol to allow me to take ill advised chances in places I should not have been as a single woman. Especially a transgender one. I was fortunate when I escaped unharmed in a couple of situations I should have never found myself in as I was dressed way to provocatively for where I was going and one time in particular found myself having to be bailed out by my second wife who had warned me ahead of time about my mini-dress being way to short. I attracted the unwanted attention of a cross-dresser admirer who was huge and had me trapped in a small hallway with nowhere to go when my wife grew curious and came in time to rescue me. Believe me, it took me a long time to live that incident down with her.

Even when I became a regular in the big public straight sports bars I was going to, I would not recommend my methods of establishing a path to gender freedom as a trans woman. Being a single woman in a public place can sometimes be dangerous to the point where you don’t see many ciswomen do it. They always bring a friend or two for safety which it took me awhile to finally come to the point where I could do it too. My only recommendation is to act like you have a friend coming to join you by acting as if you are talking to them on a cell phone, or “save” a seat next to you with your coat if it is wintertime. Better yet, you can solve the problem completely by sitting at a dining room table, but what fun is that?

Another way to attempt to find companionship is through the use of social media. I tried that too and had to sort through a tremendous amount of trash before I hit the jackpot with the person who turned out to be my third wife Liz. Unbelievably, she contacted me on a social media site which I was listing under woman seeking woman. Better yet, it turned out we were within driving distance of each other and began to correspond until I became brave enough to talk to her on the phone. I was so ashamed of my voice to do it. I finally jumped off the deep end and had success as we started to date. That was over twelve years ago and we married and are going strong I am happy to say.

I see and hear from so many transgender curious people who are on the gender edge in their life with no evident way out. My only recommendation is that at some point you need to take chances if you ever want answers in your life. The only certainty is if you do nothing, nothing will happen. I’m sure I don’t have to tell you that you do have to be careful though with all the scammers out there these days and all the negative people you may encounter if you decide to go public. With the political arena and anti-transgender laws which are being passed in many states such as my native Ohio.

No path is right and who is to say, your path is not right for you even if you decide to stay in your closet which is safe and not risk giving up things such as spouse, family, friends and employment. Maybe you can experiment too as you discover which path is right for you. As I said, be careful of the stop signs and bumps ahead.

 

 

Saturday, April 4, 2026

Easter Envy

 

Image from Annie Spratt
on UnSplash. 

Once again, it is Easter and time for some ciswomen to model their new colorful, feminine dresses and accessories to the world.

Like most of you, I remember the envy I felt when once again I needed to be forced into a restrictive suit and tie for one of the rare occasions we went to church. Why couldn’t I be one of the girls in their Easter finery. All the envy in the world I felt did me no good as off to church we went. My parents thought I just did not want to go to church (which I didn’t) but did not realize the real reason. I was just jealous of the girls.

Back in those days, I had very little inkling of how my desire to look like the other girls ran much deeper than I ever thought it would. I was scratching the surface of where I would end up in life as a fulltime transgender woman. I thought it was an innocent hobby that perhaps some day I would grow out of when the opposite happened. I grew into it. If I had any idea of all the growing pains I would feel over the years as I grew into my true self, I don’t know if I would ever undertake the gender path I did.

The truth of the matter is that I did not think I had any choice. I was born into an unforgiving male world that I was expected to excel at. I knew too that if my cross-dressing or gender secret was uncovered, I would be sent to a psychiatrist and told I was mentally ill. I did not know exactly what was going on with me, but I knew I was not mentally ill for just wanting to be feminine. On the other hand, I knew my WWII/Depression era parents would have any idea of what was going on with their eldest son to take any creative measures to help. The first measure would be acceptance. In my wildest dreams, did I ever think they would buy me a pretty new dress for Easter and do away with my suit and tie forever. My parents were simply not built that way so that they could step out of their rigid parenting box to help me. I was stuck in a male world until I could figure a way out on my own.

Over the years, regardless of setbacks such as military service, I was fairly successful in my male life. Which ironically made it harder for me to give it all up and cross the gender border when the time came. One thing I never lost was the envy I felt for all ciswomen who inherited from birth what I wanted so bad. I kept remembering the girls and women in their Easter dresses, even though I rarely wore a dress as I attempted to blend into the world as a woman. It seemed fashion had gone away from the frilly feminine basics once I arrived at the point where I could take advantage of the new world I was in. For years what I did take advantage of was the fashion trend where I could wear oversized sweaters with miniskirts, flats and opaque tights. Sadly, fashion moved on, and I needed to also if I was still going to blend in with the world as a transgender woman. Not only did I have to try to equal the cis women I was around, I needed to be better. So, I went with denim mini’s with long flowing tops to attempt to hide my oversized male torso.

Even with all the effort I was putting in, it never seemed to be enough to compensate myself for not being the pretty girl in her new dress at Easter. Ironically, then I found out from my wife Liz how she was a tomboy and did not like all the frilly Easter fashion she had to wear and was always under inspection from her mom on getting her new white tights dirty. I learned the view of the other gender side was not always the better one. It left the door open for a greater understanding of what females go through to be socialized into women and why some never make it.

This Easter, if you are religious, I hope you have the opportunity to celebrate the true message of the day and you don’t get hung up on what the ciswomen and girls around you are wearing. Although, I don’t see many women getting all dressed up for any reason anymore. Maybe if I attended any sort of church services at all, I would.

At any rate, celebrate Easter in your world the best you can!

 

 

 

 

 

Saturday, March 14, 2026

I Could Never Say No

 

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




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

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

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

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

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

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

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

 

 

 

Tuesday, October 7, 2025

I Never Missed a Beat

 

JJ Hart


Once I started down or up my long gender path, I never missed a beat, even though on occasion, the beats were far apart.

The beat started when the first time I experienced the thrill of experimenting with my mom’s clothes, I knew I was hooked as much as the garters I learned to use way back then to hold up mom’s hosiery. From then on, I went in as many spurts as I could to try to achieve my ultimate dream of being a girl, rather than just looking like one. The problem was I was restricted to hiding my gender ambitions from a totally unforgiving world. Primarily, an ultra-curious slightly younger brother who seemingly was always around. Locking myself away in the bathroom away from him only had the chance of working so many times as the instances I had of being totally alone were rare.

Even so, I managed to perfect my makeup routines in the rare moments I had. Perhaps the days of watching mom put “her face on” did me good. At least I had a working knowledge of how makeup should work, even though I struggled to improve my efforts and not look like a clown in drag. I wanted desperately to look like the other girls around me I saw at school. So much so, I daydreamed my life away wanting to be them. Luckily, at the time, I did not know how many beats I would have to make to reach my feminine dreams.

It turned out the biggest obstacle to my transgender dreams turned out to be the looming possibility of military service in the Vietnam War. It lasted so long in my youth, I literally started to worry about it when I was fourteen. At the least, my worst-case scenario of being drafted and sent off to war would wreck any ideas of fast forwarding my gender goals for years. Three, to be exact when the worst case happened, and I did get drafted. Then I took the option of serving an extra year to try to work in an Army vocation of my choice. As destiny would have it, everything turned out the best it could. Even to the point of seeing the world and coming out to very close friends that I was a transvestite. Which, in the long term, set up another problem.

The problem turned out to be that I was not being honest with myself or anyone else. I missed a beat in the worst possible way. I was not so much a transvestite or cross dresser, I was something much deeper than just having an innocent desire to wear women’s clothes. Deep down inside of me, a little voice was beginning to be heard that I wanted to again be a woman in my own right. The clothes I resorted to calming my desires meant little to nothing to me in the long term of my life. Worse yet, I missed many crucial beats of my life, as I ignored the little voice which was threatening to grow into a loud roar.

All of it set me up to escape my gender closet and begin to seriously explore the world as a transfeminine person. I needed to see if I could make it at all. When I did, the beat of my life began to totally pick up and I discovered I could make it as a transgender woman…if I wanted it bad enough. Plus, I needed to figure out what was I prepared to lose if I made the major step and transitioned into my version of womanhood. A long-term marriage, family, friends, and job potentially could all be gone if I followed the beats of my heart.

In what now seems like a blur, I was able to put less than desirable transition decisions behind me and then struck gold. Which was my experience with on-line relationships. After being stood up on countless (dates) my wife Liz of over a decade reached out to me saying I had sad eyes, and we have been together since. Never missing a beat.

Needless to say, that inner voice I mentioned deserves praise also. When given a chance, she led the way into a new exciting world of ciswomen I had only dreamed about. Even though I had gone down such a long gender path to arrive where I am today, it still does my soul good when a neighbor calls Liz and I “ladies” on our walks when we meet up. After all, I am just making up for lost time and missing many beats.

 

 

 

Friday, December 8, 2023

Burning Bridges

 

Image from Marcus 
Clemens on UnSplash

Yesterday as I sat waiting for my wife Liz at one of her doctors appointments, I had a chance to pause and reflect back on my long and often difficult transgender journey. 

First of all I marveled on how I was accepted as me. Not necessarily as a woman or a man but as just me. The whole process to arrive took me over fifty years of my life to get here. A place where I could feel secure and relax with just being my authentic self. Then I started to think of how many bridges I torched to get here.

My main problem was my old entrenched male self. Even though he never wanted to be a part of my life at all, once he did, he never wanted to give up what he earned. So he fought completely to maintain his edge. He had an edge in what I like to call the "three F's" or family, friends and finances. He had built all three and was able to maintain a great job to support his other interests. In the meantime my feminine self was doing all she could to break out of the confines of the closet she was in.  She went as far as starting small and large gender fires designed to sabotage his very existence. 

The biggest bridge she tried to burn was the financial one. What happened was I began to stop at venues close to and even part of the places I was working at during the same period of time. My thought pattern was, they wouldn't recognize my feminine self as my male self. I was wrong and they did. Leading me to all kinds of potential embarrassments if anyone told my wife they saw me. The prime example of it almost happening one night was when the disc jockey (who also worked for me as a cook) played "Dude Looks Like a Lady" immediately after I showed up. Fortunately, my wife didn't notice anything but I most certainly did. I knew then, the world knew I was a cross dresser. 

Deep down, I thought if my deepest secret was discovered I would be relieved and I would have the chance to live the transgender life I had always dreamed of. Sadly I still had too much to lose such as the first two "F's" or family and friends. It wasn't until much later, when my friends and family started to pass away and I reached an age when I could retire on Social Security did I finally see a path forward to leading a transgender life. 

What a relief it was yesterday to know I had reached a point in my life when I didn't have to be so self destructive.  No more severe mental illness or thoughts of self harm. I could sit and be reassured I wouldn't have to burn any bridges anymore. 

My Gender Workbook was Blank

  Image from Marcus Winkler on UnSplash.  Somedays, I prefer explaining the trip up my gender path as filling out my gender workbook . Of co...