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

Monday, July 20, 2026

Exceeding my Expectations

 

JJ Hart

I once worked at a great job where the company’s motto was, we exceed expectations.

As luck would have it, about the time I worked there was the same time that I really kicked my gender explorations into hyper-speed. It was the time when if I was not spending time with my second wife or working, I was out the door as a novice transgender woman learning the world. Looking back, that period of my life seems like a blur as both sides of my gender personality competed for attention.

In many ways the competition was not fair because I was beginning to feel so natural in the feminine world as my fear of doing it subsided. I was discovering that my testosterone poisoned body could indeed be shaped into something that could blend in with the ciswomen who ran the world I wanted to be part of. My confidence rose every time I succeeded in presenting successfully in the world as a transfeminine person. I was exceeding my expectations and many times I could not believe it was me.

To do so, when I could, I picked out many feminine things I could do to prove to myself that I could. Such as the time I was able to do the “Black Friday” Christmas shopping with the overwhelming majority of the women in a mall I always wanted to go to back when malls were still the place to be to shop after Thanksgiving for deals. I had tried for years to schedule such an adventure but finally, the sun, moon and stars came together for me, and I was able to do it.

When I pulled into the mall, it was already packed and I was lucky I found a close parking place to a side entrance and wore my most comfortable boots with my big soft sweater and leggings to brave the Ohio cold and headed inside the warm mall. As I said, the place was packed with women on a shopping mission, and I soon learned they could not be bothered with worrying about a single trans woman going about her business. Sadly, I did not have a long time to spend there because I needed to go to work later in the afternoon, so I had to leave my adventure behind and drive home. But, on the plus side, I could mark another experience off my feminine bucket list as I finally was able to take on the world as a woman during one of their favorite activities…getting the best shopping bargains at the post-Thanksgiving Black Friday deals.

As I took that off my transgender bucket list, I needed to rack my brain to think of other primarily ciswomen dominated things to do. Next, I decided to try my hand on seeing if I could be accepted in a couple of the small lesbian bars I had heard of in the Dayton, Ohio area. I turned out to be extremely successful in one of them and extremely hated in another. Which at the time, I did not think was too bad. The venue I was intensely disliked in was essentially a lesbian biker bar which did not accept trans women such as me at all. But the other bar did and I ended up having several great experiences there.

Such as the night when I was forced to sing karaoke by a super-butch lesbian in a cowboy hat who I did not think she ever realized I was trans. At any rate, I made sure I had paid for drinks and left before she realized why my voice was deeper than hers when we both tried to sing a classic country song by “David Allan Coe.” Then there was the night I was approached by another butch who bought me a beer and told me she ought to pick me up and take me home with her. The only problem was that I was still married at the time, and my wife would have never believed me if I told her I was abducted by an alien lesbian. Probably the best part was, out of all the people I knew in the bar was the main bartender who by accident I learned knew my male self. I never knew if she had given my secret away that the “lipstick femme lesbian” everyone was approaching was transgender. Before I found out, sadly the venue had closed, but my expectations were exceeded when I knew I could be accepted by the lesbian culture.

Perhaps my biggest win came when I was able to get away from the gay venues, I was seeking refuge in from the world and try to become more of a regular in all the straight I sports bars I used to be a regular in when I was a man. I say the biggest win because for the first time in my life I was coming out of my gender shell with the chance to learn who I really was in my new trans womanhood. All of my expectations were quickly exceeded the night I finally gathered my courage to go back to the nights I thought I was only a part-time cross dresser and prove myself wrong. I was so much more as I struggled to learn about and live my reality. The night I did it for the first time at a TGIF Fridays, set a standard for me and taught me a lesson I could never unlearn, I could never go back to being a man again.

Setting up a whole new set of expectations for me was never easy. Especially when it comes to something as complex as living as a whole new gender. I was naive about how complex a ciswoman’s life could be, as I primarily learned I had so much more to work through than just worrying about my appearance. Which was just the first high heeled step into the real world of women. Many times, I needed to kick my heels off and dive barefoot into the girls’ sandbox to survive and exceed all the expectations I had ever had.

Hey You!!!! Thanks for reading along with all my writings and as always thanks for any comments you may have.

 

 

 

 

 

Sunday, July 19, 2026

What Will You Do with your New Time?

 

Image from Elana Korcheva
on UnSplash. 

When we come close to completing a major portion of our gender recovery project as transgender women or transgender men, we suddenly learn we have more to do. It seems our work is never done.

In my case, my wife Liz and I were talking about the rare chance I had to stop my previous life as an unhappy man and start all over as a pleasant trans woman. As she wisely said, not many humans ever have the chance to stop, start over and live their lives again. Then I began to think of all the people I called “Trans-Nazi’s” who just gave off the vibes of being evil people.

I first ran into them on an on-line site I found when I first bought a home computer and started exploring cross-dresser or transgender web sites. Back in those days, complete sex change or gender realignment surgeries seemed to be rarer than they are today and those individuals who went through them were expected to move on completely from their former male life and start all over as a complete woman.

On the site, many of the transsexual women banded against the cross dressers and even the newer transgender women for some sort of supremacy simply because they had more operations than the other person. It did not matter to them when someone such as myself pointed out that my gender was always located between my ears, not between my legs. I was always placed in the gender “pretender” crowd which never made me happy as I waded into the “discussions.” As you can imagine, quite a few of the “discussions” grew quite heated behind the screens of gender computer warriors. On occasion I wondered why we were spending all this time and energy fighting each other when so many others in the outside world wanted to attack us anyhow.

Once I made it away from my computer and into the twisted reality of the old transvestite- transgender mixers that “Tri-Ess” and others put on, I was able to meet some of the “Nazi’s” one on one and changed their name to me as the “A-Lister’s”. They were the predecessors to the girls in the “Mean Girl’s” movies and reminded me of some of the less than pleasant popular girls who set themselves up on some sort of a pedestal when I was in high school. During these social mixers of course, I was left out from being with the “A” girls because I could not match their spectacular femininity. Again, I could not understand why they decided to not bring the best of femininity with them instead of the worst. But the result was that I just wanted to tag along when they went to special gay venues after the regular activities were over and most of the attendees had given up and returned to their rooms.

It turned out, once I got to know one of the “mean girls”, she wasn’t so mean after all and I was invited to her restored home in nearby Columbus, Ohio. She threw very small and diverse parties, and I learned a lot of what I thought I wanted to do with my future as a transgender woman from her. Unlike me, she was headed towards a complete gender realignment surgery, and through our discussions she helped me to determine what the best path may be for me. In her own way, she taught me to be gracious and giving in her femininity.

In other ways, her get-togethers were teachers for me. Such as the time I was in danger of being sexually molested and over-powered by a much bigger man who had attended the party as an admirer (and was only saved by my wife after he cornered me in a narrow hallway.) Plus, the first time I found I could be attracted to a lesbian and her with me on a night when my wife did not attend with me. We ended up leaving the party early and going to a big lesbian/gay venue, but it all ended there because I was married. The only problem I had was being able to make it to all the parties I wanted to because I had to work many weekend nights in the restaurant I was in.

Since I needed to make a living, I found other ways to spend my increasingly beneficial time learning what my future may be like as a transfeminine person. Even though I knew I would never be as attractive as my unintended mentor, I needed to find out if I could still make it to my dream goal of womanhood on my own terms. Too much was riding on my ultimate decision not to research it totally. Which meant trying to establish myself as a new person in straight venues I was used to. To my surprise, I was able to with relatively no problems as most of the world did not care if I was trans or not.

More than anything else, during this time, I was trying to rebuild myself into a person that never gave away any of her male past, unless I was forced to like when I came out as the person, I always was to my daughter, who accepted me and my only blood relation still alive (my brother) who did not. Which resulted in an ugly breakup which on occasion I go into. The easiest thing to say is that we have not interacted for over a decade now.

Through it all, I decided to listen to the person I trusted the most, which was my wife Liz and try to build my new feminine life as close as I could to my mentor (Michelle) so long ago in Columbus. I wanted to be a kind and giving gracious woman. Who used her extra time in life to love and cherish her new family and forget my largely toxic background.

I just had to take my extra time and make it as worthwhile as possible.

 

 

 

 

 

 

Saturday, July 18, 2026

Gender Gatekeepers in the Way?

 

Image from UnSplash

Perhaps you have gender gatekeepers blocking your gender transformation.

It is often a hot button issue for people drawn into the fray by unreasoning political debates which more times than not center around transgender girls in sports as well as trans women and men using the restroom of their choice. The problem is we all have had the gender label slapped on us from birth if we liked it or not. And what’s that old saying about everyone having assumptions? Everyone has one…Well that certainly applies to gender also. Gender is such a powerful building block for humans today, as they think they are vested in a certain gender simply by being born into it.

As far as gatekeepers go, leading the charge along with the religious right are the Trans- Exclusionary Radical Feminists or TERF’s for short. Mainly TERF’s arrived on the scene around 2008 as a way to block transgender women from having any access to women’s only spaces. Even though I would venture a guess that the average trans gatekeeper has heard the TERF term at all, she still attempts to practice it. My prime example was the night a ciswoman was yelling at me at the top of her lungs in a women’s rest room (at a venue I was a regular at) by calling me a pervert for just trying to pee. After she backed down, I got her to even give me a card to her beauty salon she ran, so I could pass it along to the very powerful LGBTQIA+ organization in town. Even though I emerged with a modest sense of success, the experience still influences me to this day. Even though I have been able to use the women’s room for years now with no problems.

Another problem I see in our trans world today are the people who assume (yes, I used that word again) that they have reached a certain age, they can be anointed with the term woman or man. When becoming a woman or a man is a socialized term and just because you were born female or male, you don’t have an automatic right to it. Beyond everything else I have gone through to achieve a transfeminine womanhood; this fact has given me more confidence than anything else when I am being stared down by an unfriendly person anywhere, I go. Chances are, I have gone through more to achieve my womanhood than they had, mine just came from a radically different path. Plus, it was more mentally driven as I rejected the gender status I was born with.

Even so, it took me a long time to not fear the gatekeepers who were trying to keep me from experiencing my dream goal of slipping behind the gender curtain and seeing if I wanted to permanently live there. To do so, I needed to take chances with my male life which had provided me with so many positives. Also, I needed to overcome the haters who thought I was up to no good as I tried to learn a new world.

From my days dealing with serving teams in the restaurant business, I learned of the power of Alpha-females. Or I discovered once I was accepted by the Alpha women in the bunch, the easier time I would have it. Many times, my plan worked to perfection when my gatekeepers paved the way for me and opened doors, I never thought possible. I was approached for the first time in my life by well meaning women who were curious about me and more importunately shunned by potentially toxic men.

As I bring up the gender with the frail sexuality (men) I need to mention most all of them were all too happy to act as gatekeepers to me. Unless they wanted to treat me as some sort of a fetish object, they were all too happy to slam the door on me. Even the gay men who just saw me as another drag queen. I grew used to having my hands well out of the way when I was dealing with a cisman.

The more I tested the public as a novice cross-dresser or transgender woman, the more skilled I became on testing the gatekeepers I was going to face. My biggest drawback by far was adjusting to the passive aggressive attacks from ciswomen who for one reason or another were out to get me. I learned a smile from some women was just masking their claws that were out to get me and I needed to move on from them quickly. As I learned, the more I was able to become my own gatekeeper and even help a few others come out for the first time themselves in the public’s eye. I was humbled and flattered anytime it happened to me.

Today I believe that the government gender gatekeepers have been emboldened by their recent political successes. But even that is being challenged here in backwards Ohio as the number one anti-LGBTQ politician in the state is being charged with child sex crimes. I bet that sounds familiar right? Whatever comes from the charges here in solid red (conservative) Ohio, it is the slightest chink in the armor of the heavily gerrymandered Republican party and brighter days may be ahead of us.

What it has to do with you is an incredible chance to vote and change the system. No matter if you are a beginning cross-dresser looking for answers in your dark closet, or an out and about transgender woman or transgender man, you need to have your voice heard. Because when you finally make it out of your closet, you will need the fewest gatekeepers in your way as you follow your gender path. Look at them as some sort of a gender haunted house of scary attractions you have to overcome to make it.

Gatekeepers can be won over and help you to survive in the world if you are a survivor and want to make it. It is a learning experience but an interesting one if you take the time to enjoy it.

 

 

 

Friday, July 17, 2026

Trusting the Process

 

JJ Hart Very Early On, 
Trusting the process in a 
rest room. 

One of the hardest things to do as a transgender woman or transgender man, is to trust the process as you continue along your gender path.

Especially when your path is lasting longer and taking you places you never thought of going to. Then you have the probability of picking up more of the gender baggage than you never thought you would. Trusting what you will take with you and what you will leave behind becomes a huge problem.

As you build your new personality, you can use your old gender baggage as positive building blocks if you can take the leap of faith to learn from your past. Perhaps, more than anything else, you must trust in yourself to believe in what others may think of you. This was very important to me as I began to build from my small core of ciswomen friends and have the courage to spread out into society.  I started following my new wife’s Liz lead and joining her spiritual group to start and then spreading out further into other “Meet-Up” groups in Cincinnati which matched our potential interests such joining writers’ groups for me, along with craft groups for Liz. It worked well for me as I was able to work my way out from being so shy around strangers and build more trust in myself.

Trust comes with a couple of drawbacks such as what if your trust is betrayed and how you will ever build trust again. Going way back to my second marriage, I destroyed most of the trust my wife and I developed over the years by breaking the deal I made to never go out of the house alone cross-dressed. I certainly was not proud of what I did but just could not stop myself from doing it. Essentially, I felt as if I was cheating on her with another woman who just turned out to be me and whatever she did was just not good enough for me. As I was busy destroying her trust, she was correct in telling me I made a terrible woman, and it had nothing to do with my appearance. Which at that time meant the world to me.

During this time and beyond, it was difficult for me to try to trust the process I was on during my gender journey. It seemed nothing was going fast enough for me to ever see if I could make it to my ultimate goal of living full-time as a transfeminine person. I guess if you take into account all the years, I spent cross-dressing my life away from the male world I disliked so much, it is no wonder I felt that way.  From start to finish, it took nearly a half a century for my male to female femininization project, which should have been more than enough time to trust the process and have faith where I was going.

My excuse that I always hang onto is that my male life was not that bad and my male self was a powerful ally with my second wife on me ever transitioning into transgender womanhood. And did I trust what all of that meant to me anyhow. I did realize any sort of a gender transition would mean I stood a very real chance of losing all the materialistic male privileges I had built up over the years. In an instance, my spouse, family, friends and job could be wiped out and I would have to start all over again. At that time, I did not think I trusted myself to do it, so my made the worst choice I have made in my life and tried to juggle a life somewhere on the gender border between male and female.

As I am always hesitant to write about, my choice to walk the narrow gender line wrecked my mental health and led me to a self-harm event. I was already diagnosed with being a Bi-Polar depressive person, so it did not take much to send me over the edge. Fortunately, I had a good therapist to help me realize my truth and help me through it. I was slowly coming to a point where I could trust the process and understand where I truly fit into the grand plan of my life the way it always was meant to be. I should have never embarked on any path to being male at all. A place which was foreign to me and I just did not belong. I was no wonder I felt the way I did around other men I was with. Full of mistrust in them for the most part.

Once I was over that hurdle in my life, I needed to begin to trust the world through the eyes of a trans woman which was hard to do. Mainly since I knew the way toxic men treated women from my past. Once again, cis women with their open minds to me joining their club were my secret to building trust again. Even though I still carried the scars from attacks by passive aggressive ciswomen, I was able to build my own new life with a feminine confidence I had never had before. I felt so good, I went ahead with my long-awaited legal name change and even longer awaited plan to be approved for HRT or gender affirming hormones. By doing so, I effectively painted myself into a gender corner I could not escape from. I had to trust the process and not try to turn around no matter how attractive the idea sounded at times when I learned what I was losing with my male privilege being taken away.

Primarily, I lost much of the knowledge of life I had learned as a man as well as needing to keep a closer eye on my personal security. Which was quickly at risk as a transgender woman joining the world for the first time and learning first hand what ciswomen already knew about being around toxic men.

As I said, trusting the gender process path I was on was never easy, but it turned out it was the only path I had.

 

Thursday, July 16, 2026

Finding Comfort in your Own Skin

 

Image from Ayesha Rosley
on UnSplash.

I believe the way to finding comfort in your own skin as a transgender person is having the confidence to do it.

Just think of all the time you may have spent in front of your mirror as you gathered the courage to take on the public and work from there. Like many of you, I experienced severe gender dysphoria every time I looked in the mirror and saw a man dressed as a woman and was afraid to go out into the world and face the public. To this day, on occasion, I still suffer from my lack of confidence in who I really am when I look in the mirror in the morning. I do my best to just ignore it and move on and take on my day knowing I am doing my best with what I have to work with. Or as a transgender woman friend once told me, I pass out of sheer willpower.

My willpower was tested during the many times that I failed in public and needed to start all over again. At that time, I had very little confidence that I was doing the right thing with my life. I had to go through years of trial and even more error before I began to build the confidence I needed to succeed in the world as a transfeminine person. When it came right down to it, many times I was excited about the prospect of going through another trial to learn if I could be successful. When I was a success as a trans woman, I wanted to do more on my transgender bucket list of things to try in the new exciting world I was in.

Most the major changes for me came when I began to really look around at what all the ciswomen in the world were wearing and I needed to put away the stubborn attitude of what I thought I should look like. As I began to successfully blend in with the world at large, my confidence began to rise, and I could relax and feel more comfortable in my own skin. It was the beginning of a life-changing gender experience which I discovered I was along for during a very bumpy ride.

In many ways, the ride to being comfortable was like my favorite roller coaster ride at a big nearby amusement park. Often the ride up was slow and uncertain to the top but was made up by the rush of going down the gender hill. It did not take me long to appreciate the rush of coming down my own personal coaster. Even though I feared climbing the heights I was climbing (as well as the threat of falling) the risk was worth it as I began to carve out a small life as a trans woman. Which I always wondered if I could do at all.

I found I could do it thanks to the welcoming embrace of several ciswomen I was introduced to. It was scary yet powerful when I began to receive invitations to special girls ‘nights out. Once I figured out what I was going to wear, then I needed to figure out what I was going to add into the conversation with the other women who I had never met. I desperately did not want to act standoffish and worse yet bitchy by not joining in with the other women who I had a chance to make friends with. Looking back, I think I was successful because outside of one woman who kept glaring at me, I was treated well by everyone else. All this sudden attention led me to a newfound confidence in being in my own natural skin that I never had before in my old male life where I always needed to be on the outlook for someone trying to take away the life I had. I was always competing for what I had earned in a what you had done for me recently world.

The reverse was true in the transgender woman’s world I had found my way into. As I became more confident and successful in just being the me, I always wanted to be, the only competition I ever felt was when I needed to use the women’s room in a venue, I was not a regular in. And even that began to fade when I learned the proper etiquette to use in the typical women’s rest room. There was no thrill in doing just what came naturally, just the relief of being allowed in women only spaces to do it. Taking away any sort of a transphobe’s argument against me using the restroom of my choice.

In my case, becoming comfortable in my own skin was a constant problem which started with the way I was raised. My parents were long on material support and short on any emotional needs I may have had. Which led me to be alone with my gender dysphoria. It was a very lonely, confusing place to be and left deep scars on my internal confidence as I had no deep connection to what my true gender skin really was. The male world I was forced to live in, and the female world I wanted to be in. So, for me, the process of gaining any sense of who I really was a difficult and time-consuming process. Plus. My confidence was so fragile that the slightest problem could send me back to my cross-dressing drawing board to look for solutions.

Over the years, I flat out wore that old cross-dressing drawing board out until I began to figure out my problems were right in front of me. All I had to do was have the courage to do something about them. One of the problems was  they were so much deeper than just trying to look like a ciswoman. I was tired of thinking I was fooling anyone into thinking I was a ciswoman and settled into trying to build myself into the quality new feminine me I wanted to be as I had earned my womanhood from a difficult, unique path.

I seized the opportunity to finally be comfortable in my own skin.

 

 

 

 

 

 

Wednesday, July 15, 2026

Existing in a Male World from the Perspective of a Trans Man

Image from Nicola Dowie
on UnSplash. 
 


In response to yesterday's post praising transgender men, I received a comment from “Gio”, a trans man who follows my writings and thoughts.

Here is his comment word for word on what he has gone through during his transition from female to male:

Thank you JJ for this nod. You know, they are a tough bunch, on the exterior. They are also exhausting. Try to teach them how to be a real gentleman and right out of the gate they label you a sissy. I always counter with being raised to respect and honor women. In the Italian Culture in which I was raised the women were savvy. The women in my family ran the show and they somehow left the men feeling like they were in charge. I witnessed this with my parents (first generation born in America) and my grandparents (immigrants - who escaped Mussolini; everything old becomes new again but that's another story). The Cis men I encounter, many of whom are wealthy Trump supporters, posit they own their women. She is to do what they say. A woman, if raped, deserved it because of how they acted or what they wore. It boggles my mind. So, I remind them that women are to be revered, they remain underpaid yet they have more talent than their male counterparts. I remind them that if married they took a vow to cherish and protect their wives. I could go on and on here. Suffice to say, it’s usually a bipartisan type of conversation and they often end pleasantly. Luckily, I've not been fired yet because mostly these are the people who keep me employed. I'm also amused by how they request me as their chauffeur to drive their wives and daughters. It's these little things that cause a ripple effect”. First of all, “Gio” thanks for the comment!

I really liked your insight into how exhausting men are because on the few times I went out with a man, I could not relax and be myself when I was catering to his ego. In my family growing up, we were a heavily male influenced crew but like you, mom ran the show from behind the scenes, so I learned a lot from her on how to be a woman, She is rolling over in her grave as we speak to hear of such a thing but it is true.

Fortunately, since I am retired, I don’t have to worry about working with any tRumpters and their backward gender ideas. But when I was employed, I always did my best to protect and advance the careers of the ciswomen around me. To the point of even hiring a transgender server at one of the restaurants I worked at. Sadly, I was transferred and she was fired by the next manager, but I tried to do my part.

Looking back, it was my love of sports and military service which kept me from wearing the “Sissy” tag early in my life and when I advanced as far as I did up the business ladder I was in, I understood that males form teams and I was able to benefit from that even though I detested everything I was doing most of the time when I needed to play the gender game I was in. Maybe the whole time, I was exhausted too about playing the male game and just wanted out to go to my transfeminine world. I took what my mom taught (more than dad) and was able to beat the system which was stacked against me.

When we are transgender, it is certainly a complicated world we live in when we need to go outside the confines of a so-called normal world. The old world is on its way out and hopefully a younger more progressive gender-neutral generation will power a better world. Especially for transgender men such as “Gio” who was kind enough to share his thoughts with us on his world.

 

Friday, July 10, 2026

It's Your World to Live In

 

Image from Gabriel Silverio
on UnSplash. 

When it comes down to it, it is your life to live and no one else’s. But life comes in the way.

The problem is often for transgender women and transgender men, it is easier said than done to live our own lives. Especially for those of us who had to wait until later in life to go after our dreams of transitioning into a feminine world. Perhaps, you were like I was and called selfish for my one-sided obsession about even seeing if my male to female dreams could ever become a reality. My second wife was fond of telling me my cross dressing should not be all about me.

The longer I pursued life on my new transfeminine gender path, I realized she was right. In order for me to move ahead in a world which felt so natural to me, I had to be selfish. It was the only way I could make the difficult decision to take a leap of faith and try to jump the gender border.

Back in those days, the only thing I could hang my pantyhose on were the annual Halloween parties I was going to dressed in my feminine finest. During these early parties, I learned a few of the basics I would need to survive as a trans woman later in life. Such as how visibly trained the human animal is to the genders, and if I was to go to the feminine side, everyone (male and female) would be noticing me. My new visible role in the world took some time and effort to get used to, but I did finally do it when I learned to dress to blend with the other ciswomen around me. It was my life to live, and I was coming closer and closer to deciding how I wanted to live it.

Before I did, I discovered I still had a whole lot of living to do before I made my decision. The problem was my male life on occasion was not that bad. Which gave me false hope that I could save it. All it did, as I juggled two genders at once, was to make my life a mental health hell as I struggled to maintain any sort of life I wanted. On one side, I had the increasingly financially successful male self-making it harder to give up all that he had earned and the male privileges which came with it. Struggling with my feminine side which felt she was in a more natural position to thrive. The end result was whatever decision I made just had to be the right one. With so much at stake in my life, I needed to go back to being very selfish with myself to make it.

In the meantime, I went into a heavy experimentation period of my life as a novice transgender woman. My goal was to try to live every moment that I could discover what a ciswoman has to go through in her life. So, I could tell if I wanted to do the same thing. I wanted to be more than the “pretty, pretty princess” that my second wife always called me when she was trying to make fun of my femininity to learn what she was really talking about. It was a struggle, but eventually I did by setting up my own version of a transgender bucket list of things to do. What did a ciswoman know that I did not became my main goal in life when I shed my male clothes and went out in the world as a trans woman. Overall, my plan worked well for me except the times I tried too hard and ended up in redneck bars where a single woman should have not been to begin with.

I did so much, I wore out my bucket list of obvious things to do and began to examine the difference between male and female privilege in society. Losing my male privilege brought about no real surprises such as having my intelligence challenged and learning to be more careful with my personal safety. While the main feminine privilege I felt was the freedom to be myself in the world and went way past just having doors opened for me by men. Needless to say, I was in love with the whole path I was on as a transfeminine person and could not wait to get back to it anytime I had to leave and go back to my increasingly unwanted male life.  I was stubborn but then again, I slowly realized I could never go back to the life I had lived before. No matter how successful it was.

As I reached the age of sixty, I could put it off no longer no matter how stubborn my male self-had become. When my second wife passed away from a massive heart attack, he was left with no allies in my life to fight with and was done. I had paid my cross-dressing dues by doing the best I could with what I had to work with appearance wise and had gone out of my way to experiment with how ciswomen live by putting myself in actual situations in life which I could expect to happen. After all of that, I just needed the final push off my gender cliff, and land in a world of my own choosing. Without a perpetual balancing act.

In other words, I guess you could say I went too far in paying my own dues during the approximately fifty years it took me to lead a life to discover who I always was. I decided long ago tt was too late to cry over what I did or did not do and to look forward to the time I have left in the world. At the least, I found living a life on both sides of the binary gender border was as scary as it was interesting. How many other humans get to experience what a transgender women or transgender man gets to see in one lifetime.

Sure, we experience our ups and downs but so does everyone else and we can have such an interesting path to claim a life which was always meant to be ours.

HEY YOU! Thanks for joining me in my journey and commenting or clapping for my posts. You make it all so worthwhile.

 

Thursday, July 9, 2026

On a Gender Vacation without a Passport

 

JJ Hart

I saw on the news this morning that shortly after the Fourth of July holiday is the busiest time to travel during the year. It got me to thinking about my own major vacations when I shed my male self and began my life as a transfeminine person.

Mainly, I remember the times when I just needed a passport to go past my natural fears, put my cross-dressing past behind me and step into the world of a transgender woman. That invisible passport was difficult for me to come by since I needed to overcome my fragile confidence to step out of my gender shadows to get it. It was difficult because my earliest days of going public as a trans woman were often brutal when the public got ahold of me and I was laughed at routinely. It literally took me years of work in my cross-dressing workbook to get to the point where I could go out into the world and make a good effort to blend in. When I did, I began to earn my vacation away from my male self.

The more vacations away from him that I had, the more I began to appreciate the new world of ciswomen I was allowed into. As rock and roll idol “Billy Idol” was singing, the more I did, I wanted “More, More, More.” (Rebel Yell, 1984) Early on, I was naive and did not realize what I was getting myself into and partially thought my need for a gender passport would eventually burn itself out and go away. But of course, the need to have a passport just burned brighter in my soul. It seemed because of the need for femininity increasingly felt so natural to me.

It turned out at that time, when I was out in the world as a trans woman, either I was getting it very right or very wrong. Mainly because I did not know what I was doing such as how to move the best I could as a woman or how I communicated with other women at the time. Because they were overwhelmingly the only people who were interested in talking to me at all as nearly all men shunned me. I was amazed at how many women in their own unique way wanted to see my gender passport and let me in behind the gender curtain.

It all led me to finally legally change my name with the help of my daughter. We came up with a family name which honored one of my grandparents and my mom too. Who never supported her new daughter, but I forgave her and took her first name as my new middle name anyhow. As a plus, my new initials were easy for my three young grandkids to remember me by, so the name was well accepted by all.

Since I had my new permanent name in place, I could start building a new permanent feminine persona every time I went out to try to carve out a new life as a trans woman. As I was carving, sometimes I hit very hard granite and had to stop and start over until I could find the sandstone softer rock and keep moving towards my gender goal of living fulltime as a transfeminine person. As I carved, I needed to make certain I was always on the outlook for cave-ins which could cause havoc with my male life. Which was still very much in the picture. Because he still controlled most of my life the public saw as well as life with my second wife (who wanted no part of losing a transgender spouse) and a very good job I had at that time too.

As life moved on for me, I discovered brief moments of gender euphoria which kept me going through the dark days of my male to female femininization. Such as when I was able to leave the gay bar venues which I felt uncomfortable in and set out to be accepted in straight sports bars which I knew so well as a man. I was in my gender heaven when I worked my way into regular status in several of the venues I coveted. Once I was accepted by the staff, I could be accepted by their customers also and I thought I had it made. Sadly, by that time the one lesbian bar I used to go to and was accepted in closed its doors and that outlet for me was over.

These days, the closet thing that I have (so far) to an actual passport is my drivers license which has a “F” for female on it and my relocated copies of my name change documents I recently went with my wife Liz on the three-hour round-trip journey to my hometown to pick up. With all the turmoil caused by the idiots in Washington DC it seems in the future I may need a real passport to vote. So, I am getting ready for that if I need one.

Other than that, I am satisfied with the lifetime of progress I have made by having a suitable passport which allows me to live a public life mainly with the acceptance and help of the ciswomen around me. I was able to ignore the occasional hater like the pharmacist long ago when I started HRT who insisted in a crowded pharmacy in screaming loudly did, I know what the Estradiol medications would do to me. Not that she cared, but I promptly took my business elsewhere. It was no business of hers to judge me anyhow and try to out me to the world.

The passport I earned allowed me to open fantastic gender doors that I never thought I could do and the one I need to get will allow me to vote I am afraid here in backwards Ohio. I am not planning to ever travel outside of the country again in my life, so I won’t need a passport for that. Just the one I have already earned the hard way along my gender path.

I would like to take this opportunity to thank all of you who take the time to read along with my writing! It always means so much when you take the time to read and comment.

 

 

 

 

 

Tuesday, July 7, 2026

Dreaming in "3-G"

 

Image from Amin RK
on UnSplash.

Dreaming in “3-G” seems to be coming natural for me these days.

Somehow, I have skipped the old two gender dreams I was having and replaced them with a more complex series of dreams I can remember in the morning when I wake up. I call them three gender dreams.  It’s kind of like going from black and white movies back in the day to full color masterpieces.

Here is an example. Recently I was having a dream that I was a guy but later became a woman complete with a new bag of lipstick. I wondered at the time how the lipstick got there but I had no answer as the dream moved on. Also, I have noticed recently that my dreams have been shifting out of my old male world and into my relatively new feminine world. I suppose I was expecting miracles when I thought fifteen years of fulltime transgender life could replace sixty years in the male world. In my subconscious.  

All my gender dreams can be traced back to my earliest days of life when I had vivid dreams of being a pretty girl and being very disappointed when I woke up in the same body every morning. But as I remember, my dreams were all in “2-G” and involved me in one of the two main binary genders, male or female.

I find it interesting that some transgender women or transgender men who I happen to talk about concerning their dreams say they are always their authentic gender self when they dream. When I have always been a mixture. I suppose that it is another complexity of what trans folk go through. The only constant in all my “2-G” or “3-G” dreams I have had over the years is that from most of them I was having a positive experience that I wanted to continue. Such as in my early years when all I really wanted to do was present well enough to make it in public as a transfeminine person. Who could blend in with ciswomen everywhere and not cause any extra attention.

What confused me was when I was starting to successfully lead a trans woman’s life, why it didn’t it follow me more into my dream world. I took what I could get and kept moving on with my own male to female femininization program. Dreams were just an integral part of keeping my gender sanity along the way. They helped with dispersing all the pressure in life I was feeling from juggling two genders. Plus, I have considered too that the anti-depressant and anxiety medications I am on may contribute to the vivid dreams I have been having.

I also find it strange when I have a “3-G” rare negative dream. I would have thought that with all the success I finally had on my gender path, I would not have an ugly dream about someone pulling off my wig in public. Especially since I have not had to wear a wig in almost a decade and never had anyone try to pull mine off when I did. It is my own version of a nightmare-cross dresser style.

At the least, when the “3-G” dreams don’t turn ugly, they are cheap entertainment and I wonder how I got here. When I do, the answer always comes back loud and clear that I made it to the place in life where I always should have been. And my dreams just are a reflection of that.

Maybe too, my dreams are finally transitioning to my current feminine self. Which is currently making the transition to just being the me I needed to be. “2-G” or “3-G” dreams should not matter anymore as they are just a needed respite from the real world we transgender individuals must put up with.

No matter where your dreams lead to, I hope they find you in a good place in this sometimes-negative world we live in today. We need all we can get to lead a quality life away from all the gender haters and bigots and a little daydream of how your future could be can never hurt anyone.

This is just a little shorter post than you are used to seeing from me today as I have to get mentally prepared for my Veterans Administration assigned psychiatrist virtual visit. I thought it would be a fun time to write about the effect dreams of all kinds have on our lives as trans people.

Good night!

 

 

 

 

Sunday, July 5, 2026

I Could Never Take my Trans Life for Granted

 

Image from Jeffrey Clayton
on UnSplash.

I learned early on in my life to take nothing for granted.

Especially when I was experimenting with my mom’s clothes and makeup. I needed to use every instinct I had to not get caught cross dressing as a girl. Which I tried to do as much as I could, so I had to never take it for granted I would never get discovered and sent off to see a psychiatrist. My paranoia ran deep back then of my parents sending me to a stranger who would tell me I was mentally ill. Which deep down, I knew I wasn’t. I just wanted to be like the girls around me.

My parents, from the “greatest generation” of the WWII and Great Depression years of our country’s history always made sure I took nothing for granted also. If I got B’s on my report card, where were the A’s I should have been getting. Was how I was raised. The only other real aspect of my life they thought they had to worry about was my interest in sports of all kinds. I was never the athlete my brother was so I was left on my own to do what I could athletically in the small rural school I went to. Even when I did manage to make the football team, I couldn't keep my mind on practice when all I wanted to do was be a cheerleader in their fancy short skirts and be admired by all the boys in school. I admired them too, just because of how badly I wanted to be just like them, and I never took it for granted that I couldn’t. It just frustrated me when I never did.

The years went by; in a hurry it seemed and even I was able to improve my feminine femininization to the point where I wanted to get out of the mirror in my closet and try out the world.

It was a good thing that again I should take nothing for granted that I would have no problems when I went out for the first time. Even though the mirror at home told me I made my male testosterone poisoned self into an attractive woman, why was I getting laughed at by mainly teen aged girls in public. I was stubborn though and kept going back to my cross-dressing drawing board to make any attempt possible to improve my appearance. What I finally learned was I needed to quit dressing the way my old male self was telling me to do and start dressing to blend in with the world of ciswomen around me. To do so, I reversed my fashion course from wearing clothes for teen girls when I was in my thirties and start concentrating on doing my thrift shopping to develop a more realistic fashion approach. That helped me overcome my thick male body with big shoulders that I had been cursed with by male puberty.

I had a dreaded inverted T body shape with broad shoulders, no hips and narrow legs to deal with. I took nothing for granted and set out to attack my fashion problems with better fashion choices. Since I was told I had good legs at the Halloween parties I went to, I built up from there while at the same time, keeping my legs not being a total focus to my look. As I built up from my legs and I wore Demin skirts often, I used foam pads under my panty hose which gave me the illusion of having hips. With my size, breasts were always a problem because I always wanted to be proportioned correctly and have the right wiggle to them. But not too big and look like a clown in drag. I struggled to find what I wanted until a cross-dressing friend of mine gifted me a set of silicone breast forms when he purged his extensive collection of cross-dressing materials. Then I could finish hiding my broad shoulders with longer straight hair wigs which fell loosely over my body.

Speaking of my body, you may have noticed I did not mention anything about restrictive shapewear. I always disliked the feel of being restricted in any way other than panty hose and padding, so I took the diet approach to losing my male stomach and did not have to worry so much about all the potential problems which might happen when I used the women’s room, do my business, wash my hands, smile sweetly and move on.

The one major accessory I was still lacking was confidence that I could present effectively as a transfeminine person in a world where ciswomen ran the show. In my mind, I was still the frightened cross-dresser leaving my closet and mirror for the first time and getting laughed at by the public. Out of sheer willpower I kept on taking nothing for granted until my life as a transgender woman became realized and I began to feel better and enjoy myself in the new, exciting feminine world I was in.

My ultimate goal was to someday have my own “padding” or curves thanks to HRT or gender affirming hormones. I was fortunate that in my later years in life when my testosterone was on the decline anyway (at the age of sixty) I received a doctor’s approval to start the hormonal program and all the changes which happened. Over the years, I was able to develop my own breasts, hips and soft skin as I have never taken the hormones for granted because I know not everyone has the health to do it.

I even went through the efforts of getting approved by the Veterans Administration health care system (which I was a member of) to get approved again for my hormones and take nothing for granted. I guess in many ways, the paranoia of the kid looking at himself in a dress in a mirror all those decades ago never left me. Deep down I still fear for those younger than me in the system having to put up with all the extreme transphobia in the world today.

We can never take anything for granted when our basic lives we value so much are at stake. Be safe out there.

 

 

 

Saturday, July 4, 2026

It Is the Fourth of July and are We Better Off?

 

Image from Ben Maher
on UnSplash.


It’s the Fourth of July and a time to celebrate the first two hundred fifty years of the United States.

I don’t want to be negative, but I am wondering what there is to celebrate if you are a transgender woman or transgender man. Making my point was the recent crooked Supreme Court decision which rejected helping trans athletes around the country by denying the request and sending it back to the states where they know the heavily gerrymandered Republican legislatures will keep rejecting our rights. Here in my native Ohio, the ruling was the kiss of death for the very few transgender athletes who could have benefitted from it.

Then there is the ongoing dilemma of what to do about our rapidly decaying dementia ridden convict/traitor in the White House he is trying to destroy. What will he try to do next is the problem when it comes to the LGBTQIA+ community as a whole.

As I always say, his effects cause harm to current out and visible transgender people as well as potential future harm to those of you in the closet who are seeking a way out. The most immediate way out is to NOT stay home and get out and vote for your freedom in November. You may desperately need those rights when you decide it is time to come out of the closet.

It is a difficult road we have chosen to live and holidays such as the Fourth of July spotlight the good and the bad that our country has chosen to do over the years such as take away the native American lands and build some of the new country on the backs of slavery. Certainly nothing to be proud of.

It all brings back remembrances of the T-shirt I wore to several Pride celebrations so long ago which said: I am a transgender veteran who fought for your rights to take away mine.

I just hope that none of the bleak scene I have painted is not too far gone to repair and my Social Security benefits continue to be there when I need them, and my transgender grandchild will be able to still work towards a bright future that they have.

I have every hope in the world that the old dinosaurs will fade away and a new generation can come along and right the ship before it is too late.

Finally, I am sorry I cannot come up with a more positive post on such an important day in our country’s history. But it would be dishonest of me to break my tradition of writing from the heart as the basis of doing this at all.

In the meantime, I still proudly display the flag I served in the past and hope for a better future.

 

 

 

Friday, July 3, 2026

Staying in Rhythm as a Trans Woman

 

JJ Hart gaining my rhythm with women.
I ma in first row on left.

 

It took me years to get into rhythm as a new transgender woman when I no longer considered myself a weekend cross-dresser.

The main problem I had was I needed to go back and forth between my male life and the feminine life I was trying desperately to learn. My wife and I had come to an uneasy truce about my increasing need to explore the world of ciswomen. She thought it was fair that I took three days out of my week to cross-dress and would even see that I had the money to go to a motel to complete my male to female femininization. Anything but me leaving the house dressed as me.

As you can tell, that was more than a fair deal but not a deal I could keep. Every time I was getting used to the makeup, clothes and movements of being a woman, I had to have it all taken away with a jolt of reality when I had to go back fulltime into my unwanted male world. Before long, I grew tired of the truce and having my gender rhythm destroyed and started to leave the house as me any time I wanted. As with most good times, my brief on an off life as a transgender woman was threatened with ending as my second wife discovered me time after time, I had excuses for being dis-honest and jeopardizing the good marriage I had but deep down I had no choice if I wanted to keep my feminine rhythm going.

Through all the good times and bad times with my second wife, I was learning what it would take for me to express my femininity and it was all me who drove us to our breaking point. More than once when I tried things such as gender therapy to curb my desires to be a woman. The only time that therapy helped me was when I was diagnosed with being a Bi-Polar depressive person which said a lot to me. Mainly it explained why I was spending days at a time not wanting to get out of bed and others when I thought I could conquer the world and it had nothing to do with being transgender. After trying several medications, I did not tolerate well, I found some that I could, and they keep my moods stable to this day. I was able to work my depression issues into my life and build them into the rhythm so I could live a good life.

Even with all the success I was having on my depression medications, I still had to face the problems I had switching back and forth between the two main binary genders. Most of the time on a daily basis. As I would rush home from work, pull off my shirt and tie and be the woman I always wanted to be until my wife came home. I was able to juggle my genders and make some sort of a life with all of this until the untimely passing of my wife from a massive heart attack at the age of fifty. Even though we never saw eye to eye on my transfeminine desires, I still loved her deeply and our marriage made it to the twenty-five-year mark.

Naturally, the whole tragic deal sent me into a tailspin, and I had to figure out what to do about my all of a sudden very lonely life. Was I going to go back to try to establish a male life with another ciswoman or get rid of my male life altogether and start all over as a transgender woman.

By this time in my life, I did not want to try another relationship with a ciswoman I would have to lie to, so the answer was clear. Take all the time and effort I had put into building my new rhythm as a trans woman and head for a new life. All the time and effort I put into presenting as well as I could as a woman, as well as communicating well as one too came back to help me. Confidence as well as an extreme amount of destiny opened doors for me that I never thought possible would happen. As my third wife Liz told me very few people ever have the opportunity to stop their lives, learn from their mistakes, and start over again. Don’t screw it up.

I took the insight I received from my time as a man observing how ciswomen live around them and tried to mold that into a new life. Because I fell into the arms of loving women during my male to female transition, I did not have to worry about such rhythms such as my sexuality ever becoming an issue. I had always desired women sexually as a woman myself, and nothing had to change. Add in my passion for history and sports and I hit the trifecta of being exactly in the place I wanted to be. Through it all, I could not believe it was all finally happening to me after all the years of sneaking around and struggling with my gender.

Better yet, I had reached the point where if I looked like a woman, walked like a woman and communicated as a woman, then I was a woman. Even though I did not gain my status the same way most women do. Their gender rhythm came naturally while I needed to work to find mine was the only difference.

Even though I was a slow learner when it came to learning to finally live how I was always meant to live, I was a survivor which was all that mattered and when I learned my feminine rhythm I never had to let it go.

As always, thanks so very much for reading along with my exploits in exploring the transgender world. Any comments you might have are always appreciated!

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Tuesday, June 30, 2026

I Was Afraid of the Truth

 

Image from Brett Jordan
on UnSplash, 

It took me a while to understand that facing the major truth in my life was not possible early on for me.

As I cross-dressed in front of the mirror in my early years, I could not believe it would be a part of my permanent existence. Even though, it was screaming at me that it was. I learned quite early, just looking like a pretty girl (or so I thought) for just a quick moment in time never held up and very soon I would be wondering what it would be like to live among the girls around me as one of them. In other words, I did not know I was much more than a casual cross-dresser attracted to feminine makeup and clothes, I was so much more. Later I would learn I was a transgender woman when the term began to be popularized.

Even when I realized, for the first time in my life, I had found a term which described me, I did not totally accept it. My truth still evaded my consciousness.  I was afraid to face it and lose all the male privilege I had built up.  All along, I resisted building up those benefits, but then again took them when they were offered. Which deep down made me feel like some sort of a gender hypocrite. Regardless of my guilt, I needed to work my way through my gender issues all alone and I had no gender workbook to follow. No all-nighters with girls my age to learn what it meant to play with the essentials of makeup and clothes all the way to learning the foundation of what it would take to build me into a mature transfeminine woman someday. If I worked hard enough on my goal.  

I was frustrated even more when I got the tiniest bit of gender euphoria when I was able to go out in the world for the first time as a trans woman and do my own clothes shopping in women’s clothing stores. Even to the point of being emboldened enough to use the changing rooms to make sure my selections fit me as well as could be expected before my weight-loss program. Increasing my shopping confidence was the fact that the clerks did not really care about my gender as much as they did about my money. Another truth I needed to learn the hard way and not be so naïve.

The deeper I got into the world of cisgender women, the more I wanted to stay. As my time behind the gender curtain was beginning to feel so much more natural every time I did it. Sometimes, the whole process felt so good, I almost panicked because I did not know if I was ready yet to give up all my male existence. I had too much vested in him to just give him away, so I continued to explore my new world as a transgender woman.  

My bottom line at that time was again what was I going to do about an unapproving spouse who was still my best friend and major problems about what I was going to do about finding work as a new trans woman. I was intimidated and forced to deny my gender truth for many more years. I tried all sorts of ways to do it. I tried everything from therapy, to trying to drink it away, to trying to outrun my truths by changing jobs and moving my family many times. Of course, none of it worked and still I refused to face the facts that were staring me down in the mirror every morning that I was not meant to be a man at all. It was like life was playing a cruel prank on me because on occasion I could still be a success in a male life without really wanting to. It seemed that every time I did enjoy myself as a man, my woman self would come along and do him one better.

Finally, I had reached the point of no return and just had to begin the series of moves I would have to make to put my male behind me forever. Tragically, my wife passed away leaving me alone to do whatever I wanted, and I was old enough to retire early and sell collectibles online to scrape up enough money to survive, so destiny all of a sudden was opening doors for me to live my inner gender truth. And to make matters even better, I even gained approval from a doctor to start on HRT, or gender affirming hormones that I had always dreamed of taking. The changes I went through under the new hormones proved to be miraculous for me. As all the external and internal emotional changes took effect were worth the wait. Even though I waited until I was sixty to start them.

Perhaps the HRT hormonal shift was the final straw in me having to face the biggest truth of my life. I was a woman pretending to be a man all along.

Truth was always hard to face for me as I did my best to run from it or just ignore it…it never went away proving my transgender womanhood was the only way could go if I wanted to respect myself in the end. Plus, the end of my life was not getting further away at my age. If I was going to act, it was a now or never situation.

One night when I was out to be hopefully left alone in one of my favorite venues to watch sports and drink beer, the blinding realization that my male life was over came to me. The only future for me could be feminine if I was going to be able to live my truth. It was when all the disastrous gender wars I had lived with over the years came to an end and I all sudden, was on the right path.

Most importantly, I had worked hard to know it was the right one.

 

 

Imagine your Dream

  JJ Hart on left, Pic Nicking with Liz on right. Yesterday, I went with my wife Liz to her appointment with her “vampires” to have her bloo...