Showing posts with label transfeminine person. Show all posts
Showing posts with label transfeminine person. Show all posts

Thursday, October 29, 2026

Transitioning Was Nothing but a Circle

 Over the years, I was able to go through several major transitions other than the obvious ones. 

Similar to many of you, I started by going through my mom’s clothes looking for the rare ones I could wear. Then I extended my explorations into her makeup and used her electric razor to shave the unwanted hair off of my legs. I did not know it then, but all my work to be feminine was just the start of a lifetime full of change. At that time, I thought that my change would be limited to the clothes and makeup until a little thought kept sneaking in that I was still missing something in my life. Finally, I discovered the missing link was the fact I wanted to do more than look like the girl, I wanted to be the girl. 

Since I was in complete denial from the world around me, I needed to work hard to hide my feminine supplies I had worked so hard to accumulate. My newspaper route with the pittance I received as an allowance did not go too far when I had the courage to sneak out and buy my own panty hose and makeup. Just by starting to buy my own feminine articles was some sort of a transition because it was the first time I was able to stand up and support myself as a feminine person. No matter how much courage it took me to do it. Plus when I ran my own hose, it was on me to replace them.

As I grew up, life became more complicated along with my gender dysphoria which had grown from a simple look in the mirror in the morning to a full-fledged urge to do more with my cross-dressing urges. Sooner than later, the urge to break out of my dark lonely gender closet would overcome me and I would have to address my needs to be a woman in the world. I was very naive and did not have a complete idea of what that meant but my voice was telling me it was time to try for the next transition in my life. 

Before I tried, I needed to take stock of what I had to work with and have some sort of an idea of where I was going to try to go. At first, I threw caution to the wind and started to just park my car near closed shops in a shopping center where I lived. Which turned out to be no challenge at all. Then I stepped up my cross-dressing game and decided I would go to one of the nearby major indoor malls around me and see if I could make it as a novice. The answer was a resounding no and I was sent back home several times in tears after being laughed at. I would have to work harder to make my new transition work or give it up all together. 

By this time in my life, I was tired of giving up on the things in life I really wanted, so I was in no mood to give up my biggest dream of all which was living a life as a transfeminine person. Even though I had such a long way to go to get there. I never counted on so many transitions which were both physical and mental. The external feminine person I was building had to be the best I could do and then combine my image with my mental strength that was telling me I was doing the right thing. On occasion too, the transition was all mental when all of a sudden I began to think of myself as more of a woman of my own making than a serious cross-dresser at all. At that point, I began to relax and enjoy my time around ciswomen more as an insider and not as a cis man looking to join the girls’ club. 

As all of this was happening, on my own personal homefront gender war was breaking out. As what was left of my male self and my second wife were fighting me over transitioning any farther into my dream world. At the same time I was dreaming of changing my legal gender markers to female from the hated male and starting HRT gender affirming hormones, my wife and male self stepped up their war against me. In a tragic and unexpected way, I won the battle when my second wife unexpectedly passed away from a massive heart attack, leaving me all alone to do what I wanted. 

It turned out, all the groundwork I had set up on all the previous transitions I had gone through came back to help me. My Veterans Administration therapist came through with all the paperwork I needed to start the ball rolling for me to change my legal name to a more proper one which came from generational family names rather than feminine idols I had encountered in the past. Then I used my new name to get a new driver's license back then in Ohio which is not allowed today. Thanks to backwards Republican lawmakers which leads me to being able to change my birth certificate which is nearly impossible to do. For the same reason. 

Perhaps, most importantly, I was able to accomplish all of this at the same time my social life was picking up as a transgender woman. I was able to establish myself as a regular in straight bars outside of the gay venues I used to go to where I was treated as just another drag queen. It all worked together to provide me with another major transition in my life. A chance to live as I always should have been. 

Ironically, all these changes and transitions I went through just took me back to me and made me have regrets about the process I should not have had. I did not ask to be born into the restrictive male box I was born into and needed to quit being a victim to eventually get myself out of it. I feel good.

Thanks for reading along with my trip back to being myself! Comments are always appreciated.

JJ Hart on my way. 



Monday, October 26, 2026

The Waiting Game

 

Image from Levi Mear Clancy
on UnSplash

As transgender women and transgender men, we often play the waiting game in life. In my case, I played the game frequently as I could not wait for the next time I could cross-dress 
and could put on makeup.

 

Early on in life I was naïve and thought that eventually I would grow out of my desire to be a girl if I just waited long enough. Of course, that never happened and I grew into a more established cross-dressing life, all the way to being a proud transgender woman. Often, I was very frustrated when I had to wait in my gender journey to clear obstacles in my path such as three years in the Army, the raising of my family and other things too numerous to mention.

 

There was also frustration when I had to learn what I was doing as I tried to cross the gender border. It was not as easy as just putting on a dress which fit me and applying skillful makeup. It took an extreme amount of time away from my unapproving family, a younger brother and an extreme amount of practice to do it right. None of the process was as easy as I had imagined but for the first time in my life, I was dedicated to doing something right and that was coming as close as I could to becoming a pretty girl. Adding to my increasing problems was that I had no choice but to go through male puberty with all the unwanted masculine qualities I received but had not asked for.

 

It seemed, the older I became the waiting game for me increased completely with it. I was still trying to carve out time to cross-dress in my closet which in itself was becoming increasingly frustrating. The time was upon me to leave my closet for the first time and see if I could make it in the world as a feminine person. Somehow, I gathered the courage to go out and then was completely rejected by the public. All my failures combined to send me back to my gender closet and return to my waiting game. Finally, I reached a point where I could wait no longer and kept trying the world until I got it right and I was blending in with the world at large where I was going. When I did, my paranoia about going out decreased and my confidence increased as I began to relax and enjoy myself.

 

As all of this was happening, it was becoming increasingly evident that a tour of duty in the military was going to be in my future. To attempt to stay out of combat in the Vietnam War, I decided to enlist for three long years, and avoid the draft. My problem was at that time in my life, three years seemed like an eternity. Especially away from my dresses and makeup. As well as the new long blond wig I managed to purchase for a girlfriend I had in college who hated the wig, so I managed to get it back. A dream came true for me until I had to leave it behind for three long years until I could get back home and wear it again.

 

When I served my three years and was back in the civilian world, I again was naïve and thought most of my waiting game was behind me. In fact, it was just getting started when the Halloween parties I went to as a woman, showed me that I could possibly live my dream of a transfeminine person after all. I just had to find the hidden keys to unlock my future which was not going to be easy as I thought it was going to be as I delved further into what I would have to do to survive and thrive in a world made up by ciswomen. As much as I had studied the world of women around me, I was not ready to go behind the gender curtain and be admitted into the girls’ club. A woman’s life was much more complex than I ever imagined and the first fact that I learned was why cismen and women do not understand each other. In order to make it into the girls’ sandbox, the first thing I needed to do was understand the new form of communication I was challenged to learn. It was true that men were from Mars and women were from Venus and initially, I felt I was on the Moon. The ultimate gender traveler.

 

The positive part of my life at that time was, my waiting game was speeding up, and I was learning new lessons on where I should be in the world nightly when I went out to socialize with my new ciswomen friends. Without them knowing it, I set back and let all of them be my feminine teachers as I tried to round off what was left of my old male life. Even still, I was impatient about how my life was going and wanted to know what was around the next blind curve on my gender path. I had waited long enough with the time I had spent by myself trying to learn a new life which included a whole new gender language.

 

Before I made the final decision to end my waiting game and jump into the girls ‘club I needed to pause and look back and see if I was making the right decision with my life. Since I was giving up almost all the male privileges, I had worked so hard to gain. I finally got so frustrated with myself that I had to do something about it. I was tired of worrying every moment of the day about what I was going to do. One night I said enough was enough and it was time to begin HRT gender affirming hormones and leave my past behind.

 

I will never think that the waiting game I played was a good thing, but it turned out I had to play out the cards that I had. We are all different which makes us human and interesting as trans folk. We just must get the remainder of the world to accept us. The fact remains the world does not take the time to understand us. So do not expect it. What you can expect is a fair break from the world as you follow your path. That way your waiting game may be a little easier.

 

Thanks for listening to my waiting game I was playing. Any comments are appreciated.

 

 

 

Sunday, October 25, 2026

Denial will Eat You Up

 

Image from Annie Spratt 
on UnSplash.

Over the years, turmoil from my gender dysphoria just tried to destroy me. Much of it came from the confusion I felt early in life as I tried to figure out if I was a boy or a girl and could I ever escape the gender box I was born into.

Perhaps the worst part of my inner gender feelings came from not knowing if what I was doing in front of the mirror was really doing me any good or was just a stop-gap measure to get me by to the next time I could cross-dress as a girl. Were my limited mirror experiences all that I would find to get me closer to my lifetime goal of being a transfeminine person. On my own terms. What no one told the young me was that the rules of my life would dramatically change. No one told me then that I would take three years of my life to serve in the military and then go through many years of therapy for a manic-depressive disorder. I was just a confused kid.

As I matured and went through the unwanted terrors of male puberty, I started to feel the pressure for the first time to fight back my gender dysphoria and do the so called “right thing” and just relax in the gender box which was given to me. Somehow, along the way, I had learned the powerful/destructive male response to some problems called internalization. I learned it from my dad as he never showed much emotion at all except when he was angry with us. Most certainly not the ideal environment for a gender dysphoric child to grow up in. There was no way I felt comfortable in going to my dad and telling him I wanted to be his daughter. So, the years went by with me internalizing all I felt the best I could. 

It was not until many years later when I was honorably discharged from the Army did, that I began to feel the increasing depression which was gaining on me. I knew something was not right and I sought out my first therapist for help. From him I learned one of basic truths of therapy, you only get out of it what you put into it. I got absolutely nowhere with my first therapist when I mentioned my cross-dressing and my growing depression which was beginning to seriously threaten my life I was building as a man. He finally prescribed some medications for me which made me feel worse and sent me on my way. I did not know what I thought would happen except nothing which did and my depression over my life began to build to the point I was not happy unless I was out in the world testing out how I felt as a novice cross-dresser.

Regardless of how negative my experience was with my first therapist; I set up other appointments to see another therapist who advertised gender therapy to try to save my rapidly dissolving marriage I was with my second wife. It was with her that I discovered another two truths about myself and the world of therapy. The first was that I was much more comfortable talking to another woman about my feminine desires than a man and for therapy to do me any good, I would have to listen to what I was told. For example, I completely ignored her when she told me there was nothing, she could do about me wanting to be a woman.

On the positive side, we talked about the major depressing lapses I was having in my life and how I spent days when I did not want to get out of bed. She diagnosed me with a form of Bi-Polar depression and prescribed me medication I take to this day which helps stabilize the chemicals in my brain which caused my extreme depression. On the negative side, I was left on my own facing my own battle about who I really was when I looked in the mirror. I was still years away from solving the major question of my life. Sadly, I was wasting valuable time in my life making the decision I always knew was true. I was always a woman pretending to be a man the best way I knew.

The best idea I had was to go out into the world and see if I could make it in a universe ran by and for ciswomen. A world which operated on a separate plane than cismen. I will always be thankful and amazed at the number of ciswomen who welcomed my arrival into their world and showed me the way behind the gender curtain. Where I always wanted to be in my life as part of the girls’ club. It was only then that doing my extreme gender turmoil begin to subside and I could relax and even be happy when I was out in the world as my feminine authentic self.

At that point, I needed to pause and reassess where a life of living a lie had taken me. All I did know was the HRT gender affirming hormones I was prescribed by my Veterans Administration therapist were miracle workers for me. I have spent time mentioning the external changes such as a softening of the skin, longer hair and bigger breasts which came along faster than I even hoped for on my femininization timetable. But I spend less time mentioning the internal changes such as emotions which came about quickly too when I found out how it was to cry. It was as if my body was syncing up with my external woman in the world by saying what took you so long.

As I said, the hormones forced me to play my feminine hand and with help of my circle of women friends, it was time to permanently leave my old male past behind. Sure, not all he had done was bad, but still there was enough negative to want me to leave him in my past and forget about all the gender turmoil behind me. 

I know I get comments all the time from those of you who have not had the chance to free yourself from the chains of your closet. I hope you have the chance soon to escape into the true world you always deserve.

Thanks for reading along, commenting is always appreciated!

 

 

 

 

 

 

 

 

 

 

 

 

 

Wednesday, October 21, 2026

Destiny or Blind Luck

 

Image from Maia I on 
UnSplash.

As I mention often, escaping the restrictive male box I was born into turned out to be not an easy task. So difficult that I wonder how I ever made it and consider if destiny or luck was involved.

Since my life was laid out for me in what I was supposed to do with my male privilege, the choice to be a female was not included. I was expected to grow up, be intelligent enough to go to college and marry another woman from the college I was attending and help the family’s genetic pool flourish. Not much of that happened as I did go to college but never met the girl of my dreams enough to want to spend the rest of my life with. In fact, I had the sneaking suspicion the only woman I wanted to spend that much time with was me. Several obstacles were stopping me such as the male box I was in and my problems escaping it.

It turned out, the only serious feminine relationships I had were my form of the gay term “beards”. I just needed a ciswoman by my side to convince the world that somehow, I was “normal.” The same way some gay men use a wife and kids to somehow hide their true selves from the world, I was doing the same thing. Over the years, I discovered that was not so much the case because I was learning I just liked being around women much more than men. So, it was more of a destiny sort of thing coming through as I would realize later as I went through my male to female femininization transition.

Just using the femininization term might be wrong because I was just expressing what I had always known about myself but could not bring myself to express. All I needed to do was refine the process of how I was ever going to achieve the goal of living full-time as a transfeminine person. Far from the casual cross-dresser I was lying to myself that I was. That was when I went through another major gender transition. As I mentally moved away from my cross-dressing mentality, back to an idea I had so long ago when I was admiring myself in a mirror at home in dress and makeup. I thought then this was fine, but there had to be so much more. As in me being a girl myself.

For the longest time, I went through differing stages of emotion all the way to a self-pity form of being a victim to a problem that I knew little about and felt that I was the only boy in the world that wanted to be a girl. Then along came the world of computers and social media and the world opened to me that I was far from the only pseudo male who wanted to be a ciswoman and did not care what it took to get there. I quickly discovered too, by going to “Tri-Ess” mixer/socials that I was not going to find my answer there either. I did not find that magic friend that I could talk about my gender secrets with because everyone I met was not enough woman for me, or too much when it came to the rare transsexuals in the room.

I did what I always had done, I went back to my own feminine drawing board and at the same time continued to be an intense student of every woman around me. Destiny, not luck was driving me forward in a single-handed pursuit of my unique womanhood. The problem was I became a very selfish person with only a couple goals in mind. Advance my femininization process and, at the same time, advance in my job so I can finance it. I knew for sure destiny had me a comfortable seat on a runaway train and I just had to make the best of it. Another obstacle which kept popping up in my way was the fact I could never make it across the gender border and behind the so-called sacred gender curtain without help from my destiny. My wife said it best when she called me a terrible woman and it had nothing to do with how I looked. The fact was that I still had years of socialization to go through before I could truly say I did not make a terrible woman and she was wrong.

I thought that since I was “making” something, I better do a good job at it. Since very few humans have the chance to stop their old life and start all over again. Except that was not entirely true as I began to think about it, destiny and being female was always apart of me. I just did not know how to express it. It turned out to be on me to learn to express myself the way I needed to be to do more than survive in the world I was in, I wanted to thrive as a transgender woman. A world I was in a rush to learn as much as I could to experience. My woman was always living rent free in my head and wanted more, and I was ready to give her more access.

With extra access, my life became easier to live as I was able to feel comfortable in my new feminine life. My vision of destiny became easier to understand too as there was no luck with what I was doing. I had earned every bit of my progress by living it and it all felt so normal. Sure, as I always point out, there were many obstacles in my way. Including a strong constant denial coming from my old declining male self. Who was a “self” in title only as all his male privileges were slipping away. I had good teachers who taught me where my true validation in life should be from…myself, especially from other cismen who were resentful that I had left their club.

I had claimed my freedom from their club, and what I always wanted to do was claim my destiny. There was no luck with it.

 

 

 

 

Tuesday, October 20, 2026

Seeing It All Clearly Now

 

Image from Lola Rose
on UnSplash. 

As I journeyed for years along my decades old gender path, I discovered I could see life much more clearly.

Going back and forth across the gender border from male to female allowed me to see what goes on in the lives of both binary genders. Something that is very rarely accomplished by very many human beings who are stuck in their restrictive gender boxes from birth. But, what about the rest of us who for some reason, got put into the wrong box and were forced to live a life we never wanted until we went out on our own to change it. That is where we start to see the changes in our gender set in. Or maybe something was wrong when we were put into neat little boxes at birth.

In a classic what goes around, comes around, we go around searching for our authentic selves as transgender women or transgender men until if we are lucky, it comes around back to discovering our true selves later in life. How we can come to that conclusion is as different as human beings can possibly be. Some of us take shorter routes than others. If I use myself as an example, I took decades to come to my gender truth that I was hiding from me the whole time. If I had the courage to face my truth earlier, my life would have been so much different. I am sure it would not have been a completely positive experience, but at least, I would have been working towards living a transfeminine life much earlier than I did as a serious cross-dresser.

I was the classic person who does not see the forest for the trees. Since all my trees had a big transgender marked in every one of them and I thought it could not be for me. Even though I was going as far as cross-dressing three out of the seven days of the week if I could get away with it.

At the least, during those three days of the week, I was learning to present better in the world the way I always wanted to. As I did it, slowly I was seeing what I needed to know if I had what it takes to cross the gender border for good and would the grass be even greener when I did it. Plus, as I always mention, I had an increasingly successful male life and family to deal with. At the least, my second wife knew about and reluctantly approved of my cross-dressing but always drew the line if I was thinking about going ahead with the next step for me. Which would have been HRT-gender affirming hormones. She always said she did not sign up to live with another woman, and I never had the courage to tell her she already did. In the meantime, I clashed with my two main ciswoman role models, my mom and my second wife. I admired them for being strong women until it came to the times, they did not accept me.

The problem was I was seeing clearly the trans person I was becoming and every positive step I took led me to believe I never wanted to go back to the male life I never asked for. Most importantly, I was building the confidence to do it and ignore the gatekeepers like my wife and mom. I felt deep down, if I kept knocking on the gatekeeper’s door, someone would let me in, and I could experience for myself what went on behind the gender curtain.

When I finally made it behind the curtain, I found the feminine reality I was always looking for. Far past the shiny fashion, hair and makeup intangibles all the way into the complex lives that ciswomen lead. By that time, I had paid plenty of dues to get there and just figured my socialization as a woman was part of life I should cherish. If anyone wanted to get in my way, shame on them because by that time I could see clearly who I really was in my unique form of womanhood. Other women saw me too when I was asked to pose for a book about different women for a judging in Chicago years ago. It was to be my only experience as a photographer’s model, and I was nervous, but I enjoyed the attention immensely.

The rest of my life was not as exciting as posing for a photographer, but in other ways, as satisfying also. I was enjoying building new acquaintances with my wife Liz as we went to writers and crafters meetup groups to intermix with total strangers. The whole experience helped to get me out of my shell and lift the fog away from whom I was destined to be in life. Most importantly, I was happy doing it. Something I was never allowed to do when I was growing up when doing good was not good enough, there always had to be something better. I never imagined how much that carried over into my adult life until I began to come out of my gender shell. Even still, I had to work my way out of the idea that there always was a better dress or wig I could buy which would magically transform me into an attractive passable woman.  It was all good until I looked in the mirror or went out into the world attempting to be myself. Some nights being myself was within reach and some nights it just was not and I needed to go back home disappointed.

I went back to my gender drawing board continually until I slowly got it right and began to present myself in the way as the trans woman, I wanted to be.  I took advantage of all the time that I wanted to see the best woman I could become on my own terms. It was the best I could do. I was done with all the denial I had put myself through which should be the topic of another blog post.

Speaking of another post, I always invite you to join me again and read along. Thank you! 

Comments are always welcomed. 


 

 

 

 

 

 

 

 

 

 

Monday, October 19, 2026

On the Path to Being Me

 

JJ Hart. On the way to
being me.

On the road to being me sounds like one of the old “Bob Hope” and “Bing Crosby” classic movies if it was not so real.

It just so happens that the road I chose took me decades to travel and I finally arrived when I was in my mid-fifties and I tried to internalize my gender dysphoria by being an occasional but serious cross-dresser. Since I had very few natural feminine qualities, I had a lot of work to do.

Little did I know the lengthy journey in life that I was on would take me down so many side paths including three marriages. Including the one I am on now. All except one lasted over ten years, so I guess you can say I made up for in loyalty for what I lacked in other areas. Such as reoccurring gender problems I shared immediately with my wives before I married them. The major problem I had was I was never being honest with myself about who I really was which was a shame because deep down early on my path I knew I wanted so much more in life than just wearing the clothes and makeup of the women around me.

When I thought I was taking the easy way out about hiding my deepest desires, I was only masking my problems which made me a very bitter and nasty person to live with. Not a good recipe for a stable marriage, but somehow, I managed to maintain them anyhow. At the same time, I was trying to internalize my gender dysphoria, I would put extra pressure on myself to do more in my search for my own brand of womanhood. What I did not realize was all that I was doing when I began to explore the world outside of my closet was just socializing myself to the male to female femininization path I was going down. And every high heeled step was getting me closer to my goal. Even though, it was taking its own sweet slow time to do it. I found that every time I took a step forward, I would catch myself taking two steps back.

What would Bing and Bob do should have became my motto as I moved on in my mainly male world I was stuck in and could not get out. The only thing I did know was that I was stuck in a cruel gender comedy show I needed to get out of. I wanted so bad not to be perceived as a clown in drag coming from a local circus. The only thing I could do was stay on the dual path I was on to maintain the only life I knew. We were living paycheck to paycheck at the time so there was no way I could quit my job and try to start a new life over. I did the best I could to keep a balance between my two genders until the cavalry came to rescue me. The only problem was that the cavalry never came and I was on my own and was forced to learn to stand on my new high heels.

For years, I went into a self-imposed transgender exile as I needed to do a deep dive into who I really was and what I really wanted in my life. Sadly, I kept on betraying my true feminine side for my macho male side who was only good for paying the bills. The only relief I got came as I learned of the term transgender and immediately appreciated how it affected me. No pun intended, but it fit me to a “T” since I knew I was much more than a casual cross-dresser at the time. But at the same time, I did not have the desire for any extensive/expensive gender alignment or facial femininization surgeries, Somehow, I was going to have to find a way to pursue my trans womanhood on my own terms. All that was remaining was to figure out what those terms would be.

The only thing I knew for sure was I was becoming certain about who I wanted to be. I was tired of lying to myself and decided to start to carve out my own authentic transfeminine life. As I did it, I was beginning to get my glow back and love the skin I was in. The problem I had was loving the skin I was in, but I had not considered all the aspects of what I was seriously considering. For example, how was I going to tell the remaining close family and friends around me and how was I going to support myself when I started to live my dream life I always dreamed of doing. It turned out my procrastination came back to help me when nearly all my immediate blood family had passed away. Along with the only long-time male friends who I still had. Since I had always had such a difficult time making friends with me, I was not worried about making anymore anytime soon. It all left me too how I would support myself financially.

Once again, procrastination worked when I waited long enough to transition that I was old enough to collect my social security and sell collectables on the side so I could get by. I made enough money to keep going out in the world as a trans woman and keep carving out my new and exciting life. I went up, down and sideways to do everything right in my power to finish my dream of being able to live fulltime as a transgender woman on my own terms. My own terms were very simple; I just had the basics of living how I wanted. But again, I was frustrated when I went to do it. I wanted the path to finding my future to finally end and I could get on with my new life.

Most importantly, my new life was all I expected it would be and I could not wait to experience more of it.

Experience in life is all we have and I hope you get a chance to experience yours!

Thanks for reading along and any comments are always appreciated.

 

 

Saturday, October 17, 2026

Was It Ever Too Easy or Difficult

 

Image from Brian Lawson
on UnSplash.

Looking back at your gender transition, was it ever too easy or too difficult? From many of the comments I receive, I would say the answer is difficult. Even if you are an everyday cross-dresser all the way to a post opt transgender woman.  

For me, it went both ways like my gender as it depended on the experience or even the day. For example, when I was getting laughed out of venues I should have been passing in, my whole life was too difficult as the opposite of gender euphoria set in. My inner stubbornness set in, and I just had to do something to make my life better.

By this time, I was in survival mode. Clinging to every shred of gender euphoria I could find. By taking the time and effort to make my dysfunctional life better, I was making it worse. Just in time, when I was in total despair, I learned what I was doing wrong in the world to blend in and begin to prosper as a novice trans woman. Mainly I was dressing way too inappropriately for a woman my age, and when I started to look around at the ciswomen around me, life began to change. As I began to build a new professional women’s wardrobe, suddenly I found myself presenting and blending into feminine situations I never could before. It was not easy, but I was getting closer.

By closer, I meant my all-important confidence that I was doing the right thing was growing too. It helped when I was able to look another woman in the eye and have a face-to-face conversation too. It was very difficult for me to get there because of my inherent shyness and other factors but with a lot of work I did it. I was far from perfect, but I was learning.

Before I knew it, I became an accepted regular at the ciswomen’s get togethers after work at a local TGIF Fridays and I was in heaven every time I did it and wanted to branch out into other similar venues which accepted single women at their bars. Even though I was having no problems at those venues, it was never easy for me as I was always waiting for the other foot to fall when someone would ask me why a man in a dress and makeup was doing there. Needless to say, it never happened and I was able to enjoy my drinks in peace. I did not think of it then, but I was suffering from an age-old condition which was instilled in me as a kid that nothing was ever good enough. If I was succeeding in the venues I was going to, why shouldn’t I try new ones.

In other words, I was not stopping my trip up my male to female femininization journey to enjoy my progress. I was still looking over my back for trouble. Another problem I always mention it was how ill-prepared I was for the internal lives' women lead. I had never been allowed to see behind the feminine gender curtain and was left to my own to imagine how it was. Naturally, I played up the good such as the pretty clothes, hair and makeup and downplayed aspects such as passive aggressive behavior all the way to having to learn all the basics of womanhood from peer group approval. I had no sleepovers with other young girls to work with or mascara lessons from mom. As it turned out, I was probably wearing more makeup at a younger age as the daughter she never faced the fact she had.

Which always made another part of my life difficult because deep down I wanted for her to accept me for who I was. Even though I tried to explain to her one night that I always wanted to be a woman, the best she could do was reject me and offer therapy. We never mentioned it again as I struggled for acceptance in my new feminine existence. I could never understand how she could reject me so quickly with no discussion whatsoever. She was part of the “greatest generation” which I guess did not include emotional support for gender issues. Since I was used to my parents not making my life easier emotionally, it was easier for me to move on.

As I did move on in my own new and exciting transfeminine world, I was able to discover social sources of emotional backup they never knew they provided. What they provided was a learning experience for me to do away with any vestiges of my male past. After the years of fighting the gender changes, he was facing, my male self finally gave up his throne fairly easily and let my long hidden feminine self-take over and erase the scars from all the fighting she went through. Most importantly, my new circle of ciswomen friends never questioned my femininity and I flourished with them. Making up for all the lost time I had as a man trying in vain to hang on to what he had in male privilege he had earned but had never had the chance to appreciate because he never really wanted them after all.

It all brings me to the now of life. I still bear the recent scars of the two new Veterans Administration nurses who kept referring to me as “he” behind my back because my doctor never does. The difference is now the gender slings don’t hurt for long because I have long since concluded, I am only me and that must be good enough. Plus, I just learned that the VA is facing a shortage of the Estradiol patches I use and I only have a couple weeks of patches on hand to use. So, once again, hormonal injections may become a reality for me. It’s another bridge I am building that hopefully I will not have to jump off.

Perhaps I will always carry with me some of the difficulties which come with a transgender life that I never started with any natural feminine qualities. Testosterone poisoning tore me up and I have paid the price ever since. But, like before, I will get over the bad and embrace the good from the family and friends who are around me.

Thanks for reading along and I hope you gained serious insight from my writings. Any comments or claps are always appreciated by you!

 

 

Wednesday, October 14, 2026

She Was Always There

 

Trans Ohio Symposium
JJ Hart

No matter where I went in my life, she was always there.

It did not matter if I was in the middle of playing a football game as a defensive end, she was always with me wanting instead to be a cheerleader. She carried over into my everyday life also as I daydreamed all the time what if would be like to cross the gender border and live a feminine life. As I dreamed my life away, my feminine side may have had an unfair advantage because I was only seeing the positives of being a girl or a woman. It seemed so unfair to me that they could wear all the pretty clothes, have long hair and not have to worry about being forced into military duty during the Vietnam War. Plus, why did I have to be the chaser whenever I wanted to ask someone out. I never saw the competition between the girls for attention, being able to wear makeup and more. They were far from the simple life I was seeing but had no one to tell me so.

Even so, she was always lurking in the background as I fought off the shyness, I felt when I had to be around people I did not know in public. Especially other girls. I did not know then why I was attracted to them in a non-sexual manner because it would be the way I would live my life as I grew older. I learned my natural comfort zone in public always came with other women and I never felt comfortable making friends with men at all. Maybe it was because she was always there in the background. Telling me what to do.

When she did, often major conflicts in my life would occur because in my male life I was always trying to put up a macho front to keep the bullies away. It was difficult to do when she was always whispering in my ear, I was doing the wrong thing when all I was doing was to survive my gender dysphoria and live. It was the beginning of a lifetime of warring genders that would consume me to the point of self-destructive behavior.

When I progressed in my career into management, she was always with me when I needed to handle the women in my crews different than the men. She was studying the way I handled myself and how the ciswomen I was dealing with handled me. Primarily, I learned a lot about how women exist with each other and how alpha females can control a clique of other women. It would be valuable experience later in life for me when I was trying to gain acceptance to the girls’ club. If I had an alpha or two helping me along, they could make my life so much easier.

It began to matter more to me when I began to listen more and more to the feminine voice who was talking to me. She was a powerful influence when other women approached me to investigate what I was all about. Somehow, I was like them but yet so different as a transgender woman. I would have to learn how to build trust with other women as a like minded person and only use the long unwanted male basics of my life when I was asked to. Such as when women asked me questions about understanding their boyfriends or husbands. The last thing I wanted to say was I never understood them either, so I helped the best I could and I was flattered by the questions.

Most certainly, she was more than in the background when I started to explore the world as a trans woman. To do it, interaction and communication was the key as I had to come way out of my closet to do it. I even went as far as taking feminine vocalization lessons to learn more about how to communicate more effectively one on one in the world. The lessons were wonderful and taught me more than I ever thought they would. I knew of course that ciswomen had their own way of communication, but not as much as I learned about the nuances of feminine speech patterns. It was a huge change for me as I had developed many bad listening habits as a man that I needed to change…quickly, if I wanted to survive and thrive as a transfeminine person. Such as beginning to closely listen to what another person was telling me rather than skipping over it to how I was planning on answering it.

As I added layer upon layer in the world to the feminine self I was building, I did not have to pay attention to the woman within me that had always been there in the background. She was having a chance to see the fruits of always being with me come to bear as she was able to take over my world. Since I had already put in years of effort into my presentation as a trans woman and had taken it about as far as I could, my background woman was overjoyed to see me take the extra step and listen to her where to go next. That step was to put the communication mode fully into my life and complete my feminine image in the world. I finally made it out of my closet’s mirror and had a chance to be happy. Something that was never emphasized in my family when I grew up. I did not know how to act with such a new emotion.

Then it became time to flip my gender equation. My male self still vaguely exists as my female self runs my life. I discovered it was nearly impossible for me to erase the decades I had in life doing my best to make it in an unwanted male world. So, I tried to take the best and leave the rest behind. It is working for me so far.

Speaking of working for me, I will not be writing tomorrow as I must go to my new Veterans Administration clinic for my annual checkup, Flu and Covid immunizations and even blood labs. I have not had any problems for years at the VA because of my gender, so I do not expect any tomorrow. But if past Flu and Covid shots are any indication, I will not feel like writing. If any thing crazy happens with the clinic’s personnel disrespecting me, I will report it.

Thanks as always to reading along with my gender journey exploits. Hopefully my thoughts can be of value to you.

 

 

 

 

Tuesday, October 13, 2026

Spending Your Whole Life Changing a Person

 

Image from Hoite Prins
on UnSplash. 

Sometimes, change comes slow in the life of a transgender woman or transgender man. I can speak from experience since my change came roughly over a fifty-year span.

During the old if I had known then what I know now experience, if I had known my male to female femininization project would have taken that long, would I have tried it at all. Then again, I would have had too because becoming a woman with my own standards was always the main dream I always had. I never knew how I was going to make it, or if I even could but I was determined to try.

And try, I did. Repeatedly until I came closer to getting it right. I spent countless hours in front of the mirror as a youth trying to get my makeup and clothes just right and dreaming of the day when I could afford a nice wig. I had had enough of my short male haircuts, and as far as change of hair styles went, I would be forced to wait until after I got out of the Army before I could begin to grow my hair out to where I wanted it. In the meantime, I was able to buy a beautiful long blond wig to help my change along.

About that time, I realized I could help my way along with a major change by going on a crash diet. By doing so, I was able to lose enough weight so I could finally fit into the more fashionable women’s clothes I was finding at all the thrift stores I was shopping at. Even the weight loss, along with my new skin care program, did not help me enough in the change department. I wanted more in my desire to be the most attractive woman I could possibly be and worked constantly at it. Much to the chagrin of my second wife who wore nearly no makeup at all. We clashed about it all the time, but I stayed on my path to always do better.

Sadly, before my second wife’s death, my formative years of change as a novice transgender woman set in. I wonder now, how I made any strides with all the restrictions which were put on me. I did know one thing that I could not see any real changes in my feminine life until I could make it out of my restrictive lifetime closet and be allowed to explore the world. Something my wife was dead set against, adding an extra barrier on my gender path. In place of being able to explore more in the world, I daydreamed my life away. Thinking what it would be like to live the experiences I had as a cisman as a woman. I would like to get back just a portion of the time I wasted daydreaming and have often wondered what I could made of my male self if I had been constantly focused on him. Of course, I could not get the time back and had to make the best out of what I had been given.

When I was able to finally break out of my closet and begin to explore the world as a transgender woman, change began to come quicker for me. I got to the point where I could not wait for the next time I had the chance to go out so I could have the opportunity to learn more about the life I should have always been able to live. In an extraordinarily short period of time, I was able to establish myself and begin to carve out a new and separate life away from my old male one. For once, I did not have to wonder what the life of a ciswoman was like as I was experiencing it for myself. The time was especially valuable to me when I began to lose most all my friends to death and I was desperately lonely. I needed a new place to turn and all the changes I had worked so hard on over the years really came back to help me.

Perhaps the biggest change which helped was that I came back as a wiser/nicer self than I ever was before. All the years of watching and learning from the ciswomen around me did come back to help me after all because I learned that all women did not fit the kind and giving stereotype of the feminine world everywhere. I gained some basic knowledge of which women to look out for in the world and how to change around their often-passive aggressive spirit. Lessons I learned the hard way on many occasions when I learned a smiling face did not mean a smiling spirit.

If I had not let a lifetime of change help me, then shame on me. So, I needed to make the best of a life which on occasion seemed to be totally out of reach. It was not until I realized it was that I resolved myself to do the little things to make me a better transfeminine person. That is where the little circle of women friends who I built up around me came in to help me. All the girls’ nights out and lesbian mixers helped me to round off the remaining rough male edges that I had and send my life in the right direction where I did not need a man’s support to validate me as a person. Another woman’s validation was just as valuable to me without all the resultant drama and sexuality questions I would have had to have gone through.

I suppose all the changes I went through in the military when I was stationed on three continents in three years got me used to change and in fact, I often craved it. It worked to my advantage later in life when I had all the gender changes I could handle. Even though my immensely influential male self as well as me trying to appease my second wife went, they never won and I changed anyhow. A drastic change from societies’ standards as I was able to cross the gender border and femininize myself from male to female.

I certainly was fortunate to be able to do it all and see the world the way I could behind the feminine gender curtain. Even though I ignored the obvious about myself and it took so long to do it.

Thanks so very much for joining me on my gender journey!

Any comments or thoughts are always welcome.

 

 

 

 

 

Saturday, October 10, 2026

Sink or Swim Time

Image from Jeremy Bishop
on UnSplash.

Coming off all my new and exciting Halloween adventures, it was time for me to decide if I was going into the deep end of my gender pool to see if I could sink or swim for my life.

One way or another, I knew I could not wait another full year to leave my closet and explore a feminine world which I had barely learned anything about. What I learned was that I loved the femininization process and wanted to know more. I loved the process of learning to apply makeup properly and the feel of the clothes, but even more the fact I was just a little closer to living my dream of how a ciswoman really lived. To accomplish it, I would have to keep swimming in my pool of life. Especially when I was in over my head.

I caught myself in the deep end too many times when I did not know what I was doing in the early days when I was struggling to blend in with the world and essentially disappear to most of it. In the shallow end of the pool, I discovered most strangers did not care about me anyhow as they went about their everyday lives. It was the deep end where I ran into problems. Since I always considered myself a quality student of the women around me, I quickly found how little I really knew about where I wanted to go as a novice transgender person.

It was not until I learned how complex a ciswoman’s life was as compared to a cisman’s did, I figure out how far I would need to swim to make it to my dream. To make it, I needed to become a long-distance gender swimmer while I stayed in the deep end. To stay where I wanted to be in the pool, I needed to fight back all the fears I had of stripping myself of the male life I had tried so hard to build up and start all over again. To make matters worse, I was highly insecure about if I could ever make it to my goal at all. You have probably heard the old saying that you must dream about something to do it and I was having a difficult time even dreaming about my own unique path to womanhood. At the time, and into the future I knew I could not afford any expensive gender surgeries so I would have to go the distance on my own out of sheer will power as a transwoman friend once told me.

The only things that kept me going were the deep sense of feeling natural when I was following up on my feminine instincts and an even deeper sense of gender euphoria any time I succeeded. Maybe I could make it after all and be more like my transgender woman friends I so admired at the diverse parties I was a regular at in nearby Columbus, Ohio. I figured they had made it in the deep end of the gender pool and so could I. Plus, every party I went to seemed to teach me more about the life I was expected to live as a trans woman without any gender realignment surgeries. Which separated me out from most all the other accomplished transgender women I met in Columbus.

From there, I left the gay venues I was relying upon for socialization and ventured into the straight bar scene I mention so much. It was all part of treading water in the deep end of the gender pool until I figured how I was going to make the next move. Either give up and go back or keep on swimming. Along the way, I became tired of all the effort I was putting into my new life as a transfeminine person until new energy came along to keep me going.

I cannot say I was not in danger of drowning if I did not vigorously keep swimming towards my dream goals in life. My already strained mental health was already causing me to be very self-destructive and a danger to myself, so I was in a bad place to be if I was in the deep end of the pool struggling to figure out my future. To make matters worse, nearly everyone I was close to in my life passed away within three years of each other leaving me in shock and nearly all alone. Somehow, I found the inner strength I needed to stay afloat until I was able to reach out to a whole new set of women friends who enjoyed my company. Above anything else, they saved me from drowning while at the same time teaching me the fine points of being a woman. I tried to thank them, but they never understood and we continued to have fun together.

Included in the group was my current wife Liz who met me in an online dating site against all odds when I was in a lesbian woman seeking woman group. It turned out we lived semi close together and were able to correspond online until our first date at a drag show. We have been together nearly fourteen years now and married for the majority, so I consider that a great success story which makes up for all the down times I suffered.

If you are considering a swim into the deep end of your gender pool, make sure that you are sure you want to give up everything you may have to not turn around and go back. It is never easy and each of us has their own particular path to follow and you need to claim your successes when you have them. Gender euphoria is often brief and fleeting for those of us who have not been blessed with many natural feminine characteristics. We just have to work harder to even stay in the pool and take everything we are given to stay afloat.

I have had several recent comments from readers who are in despair because they have nothing to work with as a novice transgender woman or cross dresser but do have several understanding ciswomen who accept them to fall back on. A great way to study the fact that all women are different and more than a few might be closer to you when it comes to shapes, sizes and personalities than you think.

As I always say, I hope you can find your own path on the way to your own personal gender freedom. Thanks for reading, and commenting!

 

 

  

Monday, October 5, 2026

Living Rent Free in my Head

 

JJ Hart. First Beauty Salon
Image

Living rent free in my head quickly became the motto of my feminine self.

It all began when I was very young exploring my mom’s clothes and makeup then expanded from there. Very early on, I gladly gave up the space in my head to a new and exciting person. Anything to escape the unwanted male prison I was living in. I did not like the day-to-day life I was forced to live as a male but could do nothing about it.

In the meantime, I was busy making space in my closet for a new person who was very demanding. She had to have clothes, and makeup to the best of my ability. And the problem was, I had to hide all of her from my family and friends because discovery would have been disastrous. As back in those days, any sort of gender dysphoria was considered a mental health issue. A place I certainly did not want to go.

As I matured into a more established cross dresser, there were several times when my closet experienced severe ups and downs when I needed to expand or limit the size and space I was working with. Perhaps, along the way, you have heard me refer to the term “purging” which means to throw away all your feminine items and resolve to go back to living a stress-free male life. For me at least, it never worked and just caused me to develop more stress later when I did not take care of the other inhabitant who was living rent free in my head. Always after purging, I found myself coming back stronger and better than ever when I remodeled my small closet into a more organized version to who I really was.

Who I really was became a very difficult answer for me to consider in my formative years coming out of the closet. Basically, the only constant I knew was I felt very natural when I was in my feminine mode and I felt a much deeper draw to it than just the thrill of wearing woman’s clothes. I did not know how I would get to a more transfeminine experience but just knew I needed to try. The problem was my male life kept getting in the way by throwing up obstacles such as military duty, marriage and jobs in my way. As much as I was fond of the woman living rent free, she was incapable of paying any of the bills which were coming my way after I got out of college and the Army.

Until I could go further in my feminine explorations, and hard as it was for me to do, I just had to back off most all I was trying to do for my ever-demanding transgender self. Once the term became popular and I could read up on it, the more trans made sense to me. So, I slapped the label on my other person living rent free in my head as it made sense to me and made me come closer to understanding the person I really was. As some wise person once said, you need to understand the problem before you can do anything about it. But before I could go any further, I needed to research what exactly I was getting into if I entered the world of ciswomen everywhere.

My world of exploration began in gay venues where I was just treated as another drag queen and even discriminated against on occasion. I quickly said enough was enough and I gathered my courage to attempt to establish myself as a regular in a few of the straight venues I had visited regularly as a man. I always had wondered when I was male what it would be like to go in several places, I was a regular in as a woman and finally I got the chances to try. I was overjoyed when I was successful in my attempts and quickly found myself in a world I had only dreamed of.

When I was doing all of this, I pretty much left my old closet behind completely as I stepped out into the bright lights of the world. After I accepted the fact, I would never be accepted in the world as a ciswoman, I set out to prove I could make it as a woman on my own terms and I did. I discovered I just had to live with my truth and most of the world would just be curious about me or just not care. All I was looking for was an even break for my rent-free person, and she got it. In fact, she got more than she ever bargained for as in a relatively short period of time, she was carving out an entirely new life as a transgender woman. My new woman friends knew I came from a different place than them but did not care.

It was a joyous occasion as all of them helped me to close my old closet for good and what about that rent-free person that lived there? She took over my life, saved the good through out the bad and overall constructed a new life for me that I had never dreamed of. As I suspected, she was not a squatter in my closet after all, she was the real deal all long and all the attention she demanded was paid back to me totally when the time came for pay back. In addition, she was nice and gentle about my male to female femininization project by telling me I had it all wrong. I was a woman hiding as a man for most of my life.

I was stubborn and shame on me for not realizing and reacting to my truth for as long as I did. But once my person in the closet took over with the addition of a few HRT gender affirming hormones, she was on her way to a freedom she would never have to give up again.

Hey you! Thanks for reading along and or commenting. Anything you do is appreciated and I hope if you are stuck in your closet, you can find your way out too.

 

Sunday, October 4, 2026

Peeling Back my Gender Layers

 

JJ Hart with "Brutus Buckeye"
In the Ohio State Student
Union. 

Following the awakening I received from the numerous Halloween parties I went to “costumed” as my authentic feminine self, I needed to determine the complex path I would take so I could survive in the world.

What I ended up deciding on was a layered effect as I learned the ropes of the feminine universe I had only dreamed of living in. Like many of you, I started slowly with trips to my closet’s mirror, cross-dressed as what I thought was a pretty girl. In essence, the mirror provided me with my first layer to build from. Since putting on mom’s clothes was a relatively easy thing to do, I needed to concentrate on wearing her makeup which was not. No matter how hard I tried at applying makeup, I somehow ended up looking like a rodeo clown in drag. Adding this layer of expertise to my attempts to be pretty were intimidating before I started to see improvement.

Once I started to believe I had mastered the makeup arts part of my new life, I needed to add a new layer and set forth to do more about doing what I could to counteract the testosterone poisoning of my recent puberty. Since there was nothing, I could do about certain aspects of my body, I needed to do better in hiding them to the world when I started to leave the closet and explore. Those were the days of crash dieting and hunting through many thrift stores for just the right fashion item I could not live without. Mirror worship came back to help me during this layer of my life when I could honestly tell myself if an article of clothing really flattered me or not. I needed to get out of my teen cross-dressing fashion years and into a more realistic look I needed to blend in with ciswomen everywhere.

Blending in brought a whole new layer to my gender existence. To my relief, women had more of a tendency to embrace who I was becoming in their world, while cismen everywhere shunned me for leaving their club.  It all was an extension of my life as a man because I had never had much of a liking being around other men anyhow. I guess it all was a precursor to the person I was destined to become as a transgender woman. Probably, more than anything else, the Halloween parties I learned from helped me to be a success during this layer of my life when I was allowed to learn the basic differences between the two main binary genders. And landing squarely in the middle of both until I decided once and for all which direction my life would take. Should I take the easy way out and stay a very serious cross-dresser or follow my instincts and achieve my dream of living a transfeminine life.

To do so, I would have to add layer upon layer to my life by taking the old male building blocks I had used to get me by and use them as a foundation to build a better future. Little did I know what I was getting myself into as I was going past the princess-appearing layer of my life. For once, I was going to have to not listen to what my parents said about me when I approached any project I took on. To put it bluntly, they always told me I “half-assed” everything that I did just to get by. To advance through the gender layers that I wanted to, I knew I could not take the old approach to life I had always taken or I simply would not make it to my dream. It suddenly looked as if it was getting closer and closer to becoming a reality.

Before I just set all the male privileges I had learned aside, I needed to see what I was getting myself into. What would I really face as a fulltime trans woman if I ever decided to cross the gender border. I was selfish and wanted to see if I could peel back all the diverse patterns of life a ciswoman goes through before I went down her path. I was lucky in that all the right gender doors opened for me as I learned the ropes of being a woman in a supposed male dominated society. To do it, I needed to learn to leave the male domination behind me and learn a whole new society which existed for and about women. But I needed to earn my way in from all the gatekeepers in my way. I learned it was not going to be easy.

It did not help that initially I was so timid when I presented myself the keepers of the feminine world and it took me the “two C’s” to overcome it. The “two C’s” I speak of are courage and confidence. I needed the courage to think I was ready for my next gender layer and the confidence to do it. Somehow, I needed to get back out in society and prove myself all over again and carve out a totally new life as a trans woman for myself. I needed to keep reminding myself that yes, I was different, but what was wrong with that. I would never be a ciswoman but my socialization as a woman came from a whole different world you would not understand unless you lived it. Surprisingly, the gatekeepers let me in and I decided right then that HRT or gender affirming hormones should be in my future to provide a major kick forward in my transition femininization journey. I had done most of the hard work peeling back the layers I needed to learn if I wanted to do it and now it was time to take the easy hormonal way towards my future. I say easy because my body took to the hormones like what took you so long and all the changes seemed so natural.

The main thing I learned along my gender path was the number of layers I would have to peel back to achieve my goal. I knew going into it that nothing would be easy, but nothing prepared me for what I was about to face. Once I did face my reality that I was feminine all along, it was clear sailing to my dreams.

As always, thank you very much for reading along and I hope my experiences can help you along your gender paths. Comments are always appreciated.

 

No Learning Experience is a Waste of Time

  Image from Christian Lue on UnSplash. Now that Halloween has come and gone, I am sure that some of you took advantage of the freedom of th...