Showing posts with label ciswomen. Show all posts
Showing posts with label ciswomen. Show all posts

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.

 

Tuesday, July 14, 2026

In Praise of Transgender Men

 

Image from Aiden Craver
on UnSplash. 

I am fairly certain that this is the first time I have written a post which almost exclusively deals with transgender men and how they relate to trans women. But it is long overdue as I know I have several transmen who join me on occasion and read along.

Plus, they are kind enough to comment on my writing to give me an idea of what life is all about from the other side of the major transgender border. Sometimes I even have a hard time remembering what the time was like when I was struggling to be a man, so I can understand and comment back.

My actual dealing with trans men goes back to my first dinner date as a transfeminine person. At the time, the person who asked me out identified as a super butch lesbian who had not yet decided completely to live a male life. We went to dinner at TGIF Fridays and yes I was scared to be on my first date as he reminded me of later. It was the first time I was not in complete control (or thought I was) for a date and I got to see life through a whole different viewpoint.

To this day, I still follow his social media to see what he is up to and on very rare occasions in the past, he included me in some of his observations which happened when he transitioned from the other side.

It turns out, many of the same obstacles of crossing the gender border are the same but just reversed of course. Such as the problem of suddenly using the opposite restroom that you were used to using. I wondered what the shift was like from a brand-new male viewpoint when you were expected not to make any eye contact with another guy in “the room”. You were there for one reason only, and that was not to socialize, do your business and get out. Then there is the problem of having to use the stall to pee and having another guy hear you do it. As we all know, cismen have a very fragile sexuality which could be challenged unknowingly at any time when you play behind the gender curtain from female to male.

Not so long ago, I received a comment from a trans guy named “Omey” who said he was not accepted much anymore by the girls he used to know but I would think leaving the girls club would not be dealt with so harshly as leaving the men’s club is for transgender women. I know the club house door was slammed shut on me quickly when I left the men’s club for good. Again, it goes back to a man’s basic lack of belief in his sexuality. I found ciswomen did not care as much that I was living in their world as much as men resented me leaving theirs. And I wonder what transgender men face as a challenge from other men as they try to break into the “team.” Because, like the rest of us, they have no gender workbook to work from.

I know I am forgetting many of the details that went into being a successful cisman for me such as the one-on-one confrontations I had with other men. I was fortunate in that I had built up enough male privilege to get by. Basically, other men could not challenge me at work because I was the boss and could fire them. Even though that was always my last resort. I also found that men are more effective when they build teams and women when they are allowed to form cliques behind alpha-females. Which I know is a stereotype but a successful one for me.

Then there is the argument who has an easier route to passing in the world as their chosen gender, trans men or trans women. I am biased, but I think trans men have an easier time of transitioning into the public once testosterone has a chance to take hold of their body. It is the reason we see so many transgender men later in life with male pattern baldness. Before the baldness sets in, trans men also have the benefit of a good haircut which can make them appear more masculine where transgender women usually must wear wigs because their baldness has set in already.

The more intrusive cosmetic operations from both sides of the gender spectrum are pretty much a give and take in my opinion. Trans women can’t wait to grow their own breasts through HRT while trans men want to go through the traumatic operation to rid themselves of theirs. It’s all a matter of which side of the spectrum you are on, but trans women are more apt to go through more severe facial femininization surgeries to rid themselves of their testosterone poisoned male features. Not to mention the incredible expense most must go through to do it.

My praise goes out to the transgender men who can bring the best examples of the feminine culture with them. Such as deep love and understanding and applying it to a masculine world which desperately needs improving. There are far too many toxic males running around these days. I know early on I benefitted from the understanding of trans men and found them to be so much more intellectually stimulating than cismen and their drama. That is why I so enjoy hearing from trans men, ciswomen and the rest of you on a regular basis.

I am sure, no matter where you end up as a trans man or transgender woman, you are more than happy to give up your place in your old gender world to anyone who wants it. We just need to be allowed to take the best of both worlds and build a better one from it.

Thanks again to all of you who read along and even take the time to contribute to my writing! I’m sure in this post I have skimmed over many of the obstacles transgender men face, and I just hope I flipped my usual script and mentioned a few.

 

 

Sunday, July 12, 2026

A Want...or a Need

JJ Hart Discovering her Needs
I am in the first row on the left.

When a want turns into a need, sometimes you can feel it. Other times, not so much as if it sneaks up on you from behind.

As I began to wear dresses and makeup as a young boy, for the most part, it was because I wanted to do it. Cross-dressing just relieved the pressure of my unwanted everyday male world. It did not take me long to figure out my want was much more than just a casual appreciation of women’s fashion and makeup.  I did not know it then (and the term had not yet been widely used) that I was transgender more than a cross-dresser. I could not feel the change because I did not have the gender knowledge to do it.

Life began to change for me when I started to cross-dress for the thrill of it and attend Halloween parties. The parties ended up teaching me the basics of being a woman in public around people I knew, and I wanted to take it a step further by not having to wait another year to try again to get out of my dark closet and into the world. That is when my story turned out to be dark as I was not met with many positives by the public as a novice trans woman, cross-dresser or whatever you would like to label me as. To too many people, I was simply a man in a dress and clown makeup. I learned the hard way to get back to my drawing board and work harder on my feminine craft to find out if I was ever going to be able to succeed at all at my dream.

I also learned that if I was ever going to find success on my gender path, I was never just going to make it by just thinking it was just a want. It had to become a deep-seated need. I went back and dieted, worked on my skin and did everything I could to improve my testosterone poisoned body. All it really taught me was how much deeper I needed to travel along my gender path to make it at all and I needed to do it very badly. As the pounds melted off, I was able to find more stylish feminine wardrobe items to fill out my fashion needs and dress for success to blend in with the rest of the ciswoman crowd. Who I learned the hard way, were the people who ran the world I was attempting to be a part of. Or I could go casual if I needed to and a more polished business look when I needed to upscale my appearance. Fashion-wise I was learning that looking the best I could and blending in with the public at the same time was a definite need not some sort of a frivolous want just to justify something I wanted.

The more I tested the world as a transfeminine person, the more I needed to do to help myself along in the learning process of just belonging in the world I always should have been a part of to begin with. It was a real chore just to put the mirror image I thought I had perfected into the public and into motion to see how it worked. For the most part, I was improving to the point where I needed to start trying to communicate with the world as a more complete trans woman. As I always point out, the communication challenge to me was immense because I had always been a lazy communicator in my life. By that I mean, I had never really had to listen closely to what another man was telling me. I knew instinctively how to respond to another man but was clueless when it came to woman to woman talk. Which I always had known was different but how different I did not know until I was made aware of it. For example, for the first time ever in my life I needed to really stop and listen to whomever was talking to me. Were they trying to point out danger to me or just being friendly as a ciswoman who was curious of me or a toxic man who just viewed me as some sort of a fetish object.

Quite possibly, the communication aspect of my male to female femininization need passed my desire to be as attractive as I could as a transgender woman in the world. Instead of just wishing and wanting to be accepted as an equal by the other ciswomen I met, I needed to make it a priority. I even swallowed my pride and took female vocal lessons to make the process easier. It was difficult, but I think I gained enough confidence to help with my overall presentation and life.

I was helped too when the pressure to succeed was relieved here and there by the new success I was having in the world carving out a new life which on one hand to be terrifying and on the other feeling so natural like I was coming home to the self I always should have been.

I found I did not discover all my true self until I could step away from me for a minute to look at how far my gender path had taken me. After years of experimenting and trying different things, I finally achieved my need to be allowed to play in the girls’ sandbox and I was not disappointed with what I found there. Even though I had to put up with the occasional hater or TERF who wanted me out, but the majority of women made me feel welcome in their world and that was all that mattered to me.

The sandbox provided me with firm lessons and reassurance in what I was trying to accomplish in life. The want I always felt was always a hidden need which took me years to realize was my true problem in life to solve.

I hope you can realize your true wants and needs on your gender path also and life becomes easier for you if you are searching like I always was.

 

 

 

  

Saturday, July 11, 2026

It's a Lonely World

 

Image from Jarle Johnasen
on UnSplash.

It is a lonely world for many transgender women and transgender men as we journey along our dark gender paths.

As I always point out, like so many of you, I got a late start on filling out my gender workbook on how I was even going to begin a transfeminine life. Before the word was even invented. I was not invited to any overnight stays with the girls I admired so much to take advantage of early make-up tips and even feminine peer pressure on the clothes I was wearing to do a better job of looking the best I could in front of the mirror. Ironically, I was probably ahead of most girls age-wise when I started wearing makeup and shaving my legs, but I did not know that because I was not allowed behind the gender curtain to play in the girls’ sandbox.  

Looking back, I thought for a while there was always a chance I was going through some sort of a phase and I just could not be the only boy in the world with a strong desire to be a woman someday.

To make matters worse, I was always exceedingly shy back in those days which made me an introvert, and I had a tendency to not trust others. That would manifest itself much later in life when I had a very difficult time making close friends. Especially with other men. Who I thought would never understand my deepest darkest secret which by then I knew was no innocent phase in life I was going through. Not surprisingly after a while, I lost most of my shyness around ciswomen and enjoyed my time with them even more. Even though my true motives were never revealed that I just wanted to be like them in the worst way possible and I was just trying to see what it took to live their lives.

Even though I was still married to a couple of very different women through this portion of my life who knew of my cross-dressing desires and did the best I could to surround myself with other women, deep down inside I was still lonely. It never occurred to me why and what I could do about it for years. I just never realized for the longest time that I was living much of my life completely backwards. I was never meant to be a man and was forced into it by a cruel twist of fate I could do nothing about. Being a woman trying to live as a man put a terrific strain on me and caused me to constantly dwell on what I was doing wrong to feel so lonely.

When I finally made it out of my gender closet and into the world, my loneliness amazingly began to go away when I started to interact with other women. While men shunned me, ciswomen were curious why I was in their world. When they found out I was not some sort of fraud and a honest human being, it was OK to talk on a shallow level. Which was fine with me because I was so lonely after my second wife unexpectedly passed away. Her death taught me to never take anything for granted again and I set out to live more deeply as the transgender woman I was becoming. Just breaking down the gender barriers I was doing was never enough to get behind the gender curtain. I needed to do more.

Primarily, I needed to learn all over again how to talk to people. Mainly women but also men. Women I found came at me from all different directions and practiced a lot of nonverbal communication. I needed to practice the art of passive aggressiveness also when I found a smiling woman was not necessarily a friendly one. Until I proved to be up to the gender communication challenge, life became very interesting. Perhaps you have noticed that for the most part I left men out because for the most part, they left me alone. Which was fine by me, because with most of the men I did encounter, all I did was soothe their ego. Payback I guess from all the time I spent in the male world.

By this time in my life, I was looking at being sixty directly in the eye and could see very few avenues available to me to combat the extreme loneliness I felt at the time and had just figured I would have to spend the rest of my life by myself. As someone once said, the darkest hour is always right before the dawn and that is what happened to me. I already had my casual lesbian friends who met with me several times a week to watch sports and drink beer until my current wife came along online of all places and we cemented a wonderful relationship. Firat of all, Liz made me a believer in myself again. A confidence I had always had as a man but never as a trans woman.

Unbelievably, destiny had worked its magic, and I found someone to love in the world again and we lived close enough to make a romance work. As long as we are together (over twelve years now), we will not have to experience any lonely days in a cold world ever again.

For those of you who want to know more about how I did it was the only way I made it out was putting myself out there in that same cold world. I had to battle my fears by going out in big straight sports bars and becoming a regular. And, beat all the long odds to find a romantic partner on an online dating site. My big break came in the sports bars when a bartender I knew as a regular set me up with her single lesbian mother who I am friends with to this day. My moral to the story was I needed to put myself out there before I could reap the benefits, but I know the world has changed and you have to be careful.

One way or another, we transgender women and trans men live in a potentially very lonely world which is a shame because we have so much more to offer than the average human because we have seen so much in our lives.

Thanks for reading along and contributing with claps and comments! Hopefully I can come up with something meaningful to you.

 

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.

 

Monday, July 6, 2026

Just Feeling Good Being Me

 

Image from Mathilda Khoo
on UnSplash.

Just feeling good being me took me years to learn. In fact, I needed to go through three male to female transitions to get there. 

First, I needed to go through all my cross-dressing years and feel the angst of how I looked above everything else. In fact, when I go back and read some of my very early blog posts, all I basically mentioned was my presentation as a woman and not how I felt as one. It probably was because I did not feel transfeminine at all at that point in my life. Or, in other words, I had not matured yet in my journey to transgender womanhood.

I wonder if I had known what a long and winding route, I ended up taking, if I would have still attempted it years later. But it turned out, life had a different path for me than nearly all the other people I knew. Since I was deprived of having any input on where I wanted to go with my gender struggles, I was left on my own to find my way. Many times, the only clues that I got came from the dreams I was having that I was actually a pretty girl and was very disappointed when I still woke up in my male life. I was not feeling good at that point until I could make it back to my makeup and dresses to cross-dress in front of the mirror. That was all well and good, except the time feeling good, or gender euphoria I learned it was called, did not last very long.

Somehow, the good feelings took over regardless and I pursued a feminine life even harder. It did not matter that the more I tried to do to transform myself into a pretty girl could result in disaster if I was ever discovered. I don’t know how I never was, except mom maybe knew and just did not want to bring it up thinking I would outgrow it. It turns out the only thing I outgrew was her clothes and I had to be resourceful to find fashion items that I could add to my wardrobe and wear. Like one day in junior high school, I found a discarded stretchy elastic skirt that fit me, and I brought it home with me and cherished it for years to come. I was fortunate in finding me a pair of girls’ shoes in my size at the store where I had first gone shopping with my own money for makeup. I could even afford them along with being able to buy a new pair of panty hose. To come up with the money, I worked a rural newspaper route and put the money I earned together with money I earned from doing chores around the house. I was on a mission to succeed feeling good as me, as a girl.

The mission was due to be paused as military duty came my way during the Vietnam War as I ended up serving three years in the Army. My new task was to put my cross-dressing life on a back burner as I went away to serve. Even though I was bitter at the time since I was drafted by the government to do something I was totally against, I got a lot of good from it as I traveled the world (covering three continents in three years) and learning powerful lessons about life. Army basic training in particular taught me what I could do to survive on a temporary basis without a skirt and makeup to fall back on.

Even on those long-forced marches I was on, during a not so mild Ft. Knox winter, I learned to always look ahead and not behind me. I used the lesson on the days when I encountered a gender hater or TERF (cis woman gender gatekeeper) who wanted to berate me because I knew I could outlast them. The TERF just couldn’t grasp that I was not there to threaten their femininity, I was there to be me and live mine.

After all that learning experience, I still had a long way to go to feel good about being me. As I always say, I was similar to most other men in not understanding what really goes into a ciswomen’s life. It did not matter that I had spent my life admiring women from afar, I was still a novice at trying to go behind the gender curtain to truly understand a woman’s life. And I would not come close to feeling better about the gender disconnect in my life until I did.

I left the world of gay venues and started to enjoy my new life in either one of the very few lesbian bars which were still open at the time, or one of the big straight sports bars I was used to going to as a man. All I knew was I was being accepted as the transgender woman I always wanted to be as a regular in those venues and I loved putting my old male self completely in my past. The new strangers did not know anything about him and the positives and negatives about his life, and I wanted to keep it that way. Until I found a few friends I could trust. At that point only could I begin to fill out my life’s story to them. While at the same time never alluding to the fact that I ever lived a male life at all.

I was a little slow, but my life came full circle from being a part-time cross-dresser to a transgender woman, back to just being who I was always meant to be (me) and I could feel good about who I was for the first time in my life.

Earlier in this post when I was mentioning my military experience, I wanted to take the time to thank Dana and Bobbie for their input on my Fourth of July post. They were both in the Navy and Bobbie in particular is very active in the state of Michigan pushing equal rights for the LGBTQIA+ community. I know too there are other trans vets who follow along and I appreciate you too! All of you who just read and or comment are always deeply appreciated. Trans vet or not.

 

 

 

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!

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Thursday, July 2, 2026

The Best Advice I Never Got

 

Image from Frame Harriak
on UnSplash. 

The best advice I never got came from no one.

There was no one there to tell me anything about what I was doing when I was doing my best just to be feminine. No one to tell me my skirts were way too short and tight and my makeup looked like I just left a circus clown drag show. And better yet, no one to tell me I was heading along a gender path which would ultimately ruin my life if I kept it up.

The only person who was screaming in my ear initially as I cross dressed in front of the mirror was my male self-telling me to hurry up and get done before I risked discovery and the end to the world as I knew it. This was the time too when my feminine side was lying to me by telling me I was a pretty girl. Maybe I could see some of my femininity in my pre-male puberty years but quickly faded with my bodily changes.

As life progressed as it always does, I witnessed the battle of my voices as once again my male side was telling me to stop cross-dressing and never do it again and my feminine side saying keep on trying and things will get better. Even though it was difficult to listen to the best advice I never got I kept deciding to pursue my feminine side and see what would happen,

At that time, I was stuck in a series of Halloween parties where I could dress as myself and not fear reprisal. Plus, I could judge how I was doing with what I wanted to wear and with how far I had come with my makeup skills or lack of them. I was aware that I was at risk for stirring up potential risks of being discovered when someone would ask who shaved my legs and applied my makeup. I just said I shaved my own legs and did not mention who did my makeup because my second wife did not wear any. I was normally Ok because it would take another ciswoman to question my makeup because if a man did, I would figure he may be part of my femininization club. I learned so much from the Halloween parties I went to that not going to them dressed as myself was the best advice I never got.

I think it is ironic that that almost everyone has advice for everyone else except when it comes to transgender women and transgender men. It seems, our situation is so unique that the only advice someone can come up with is just not do it. They have no understanding of what we are going through, and it is so much deeper than just wearing clothes of the opposite gender. Maybe that is why I never got any advice from anyone except one of my self-proclaimed gender therapists who told me there was nothing she could do about me wanting to be a woman. Like a dummy, I ignored the only good advice I could have received at the time.

It wasn’t until I started reading certain on-line computer sites did, I really encounter advice as transgender “Nazi’s” as we called them. Who continually did battle with many cross dressers, who received little or no respect from the transsexuals as they were called then. Being the cynic that I am, I enjoyed quite a few of the comments as the gender battles raged on. Seemingly, respect from some on the site was only gained by how many gender surgeries you had gone through. Why I needed to wait to receive advice I did not want from an internet site which should have been welcoming to all but wasn’t.

By the time I hit my experimental stage to judge where I should be in the world as a man or a trans woman. I was not in much of a mood for much advice, and it was the best advice I could ever get. I was very much on my own in the world as a new transfeminine person and loving it. If someone had told me to stop what I was doing, I would have said hell no as I was having the time of my life.

I think other ciswomen sensed my confidence in who I was and mostly just interacted with me out of curiosity and at the same time, without knowing it showed me the way behind the gender curtain. I needed their help to achieve my dream, and not much advice. As the curtain parted and I learned what I needed to exist in a world I had only dreamed of, the best advice I got was none because I did not seek it out.

I cannot say I did not need advice when it came to making my final gender decisions. Primarily the day when my future wife Liz saw me mentally struggling again with my gender issues and flat out told me she had never seen any male in me. Go ahead and transition into a feminine world. In all fairness, I heard the same thing from my second wife years before but could not figure out how to do it. This time I could do it and received a doctor’s approval for HRT gender affirming hormones and major changes to by external and internal body was underway.

It turned out to be the best advice I ever got. Especially when my stubborn self-listened and decided to change my life for good. To the place it should have always been. Making my way in a world of ciswomen. Now I want the time back that I lost, but it is too late. I will just have to take my own advice and make the best life I can with the time I have left.

Thanks to you all who read along with all my experiences. Hopefully they will help you with yours and of course I will offer my own advice from all that I learned when you comment. Without all of you, none of what I do would be meaningful to me.

 

 

 

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.

 

 

Monday, June 29, 2026

Dealing with Stress as a Transgender Woman

 

Image from Ksenia Berjoz 
on UnSplash.

In the male world I did not want to be in, I had a difficult time responding to pressure except where I worked where oddly enough, I thrived.

I suppose the gender pressure I was under started very early in life when I needed to struggle mightily to even find the private time to even try to be the pretty girl I wanted to be in front of the mirror. From my early cross-dressing years, instead of growing away from feeling the pressure I was feeling, I grew into it. On one side, I had the fond thoughts of gender euphoria dominating every spare moment that I had and on the other side I had the reality of having to compete in a world I never wanted to be in. Football was a prime example of me trying to overachieve and ended up breaking two bones doing it before I just quit.

Moving forward to the time when I left my closet and started to discover the world as a novice cross-dresser or transgender woman, the pressure was on more than ever before to succeed as neither of my egos were taking getting laughed at by the public well. My feelings hurt, and the pressure as I said was building to do something about it.

The first thing I knew I could do was go on a diet which quickly slimmed my body so I could find and wear more fashionable clothing and started to take care of my skin better everyday after I shaved. All of this helped me to feel better about myself, and I kept on trying to perfect my makeup techniques to improve my public presentation. With all of this, it still took me quite a while to build my fragile confidence to a point where I could go out in public again.

Then I found myself in a spot where pressure was coming at me from different angles. On the days I thought my makeup and clothes were at their peak of success, the pressure would set in about how I was moving as a transfeminine person in the world. I needed to concentrate on two things, not moving like a linebacker in drag and making sure I put a pleasant look on my face. Replacing the male scowl I had perfected for so long. If I was enjoying my new life, I would have to make sure I showed it to the world.

As I did all of that, my inner pressure began to change once again as I began to free myself from the drag atmosphere of the gay venues I was going to (where I was considered as just another queen) and into the straight world I was used to where I could at least have a fighting chance of being treated as another woman in the world where the ciswomen ruled the scene I wanted to be accepted into. For the most part, I discovered that most ciswomen did not notice me, or if they were, they were just curious why I was trying to play with the girls’ club and leaving the universe of men.

At that point, I nearly panicked from all the pressure I was under as I desperately tried to maintain what was left of my male life which included my wife and job and at the same time try to allow my feminine transgender side to flourish also. My main reason to panic came when I needed to learn immediately how to communicate one on one with other women. To relieve the pressure, I went all out and even took feminine vocal lessons and I had to focus for the first time in my life on really listening to what someone else was telling me because I found that ciswomen were the masters at non-verbal or passive aggressive communication and used both methods to by pass the men around them. Which was the main reason men said they could not understand women. The women had set it up that way.

I did maintain that life as long as I could before the pressure increased again until the forms of relieving it, I was using, just did not work any longer. On top of that, I was becoming more and more self-destructive, and I kept putting my life in danger. Fortunately, before anything severely happened to me because of the pressure I was feeling nothing severe happened to me and I began to build a new exciting life out of the ashes of the male life I used to live. I took what I could from him and added it to my new transfeminine life I was beginning to carve out for myself.

Magically then, much of the pressure I was feeling about my male to female femininization started to drain off me. I can’t take all of the credit because I fell into the open arms of so many ciswomen who had problems of their own and took the time and effort to help me with mine. All their efforts reinforced why I wanted to be allowed behind the gender curtain to start with.

After the pressure was released, it was like the sun came out to me on a cloudy day, I can’t say how much weight was lifted from my shoulders when I finally saw the sunlight and decided to put my male self in my past and begin HRT or gender affirming hormones under a doctor’s supervision.

I can’t say before then I had any knowledge at all how to live a life without experiencing gender pressure. As I matured into a confident transgender woman, I finally realized I did not have to live that way, and I had the built the confidence to change it.

Certainly, living under pressure is no fun, and I would not wish it on anyone. Also, I know everyday humans have stress in their life, but I am biased, but I think transgender women and transgender men have more than their fair share to deal with. How we are able to handle it can define our lives.

 

 

 

Sunday, June 28, 2026

Swimming Upstream as a Trans Woman

 

JJ Hart. Pride image.
Ohio River in background.

I was very stubborn as I hung on to my male persona as long as I could. In the meantime, the struggle between my two genders was monumental.

Since I started life as a biological male, he sprinted off to an unfair advantage over my feminine self. Mainly because, like it or not, being male brought with it a series of benefits I would come to call male privilege. Even though it was hard to do, each time I was moderately successful as a boy I was rewarded. Even though, deep down, I did not want to be because I knew someday, I might have to give up all that hard earned male baggage to lead the life I always dreamed of, as a  transgender woman. Full time without any restrictions.

Along with being stubborn concerning my chances of ever living my transfeminine dreams, I was also very naïve when it came to having a grand plan on how it would ever happen. When I looked at the stream that crossed my gender path, at times it would become a river that was hard to cross to get to the feminine side I wanted to be on. There were times too, when I miscalculated the depth of the water upstream, I would have to face to get to the other side.

As the water subsided, and I could try to get out of my home mirror and into the world, I ran into new situations which would define parts of my life, and I would not know it yet. Such as the Halloween parties I went to as a woman and were immediately shunned by my male friends who were there also. Little did I know that later in life when I began to explore the world as a transgender woman, men shunning me would be a common theme. Ironically, at the same time, I was learning the opposite would happen with women. Particularly lesbian women. For the first time, the stream was busy pushing me in a way I never thought possible. It happened one of the nights I was a guest at the LGBTQIA+ diverse Columbus, Ohio parties I always went to.  That night a lesbian I had never seen before showed up with a friend and the attraction between us was real. We ended leaving and going to a big lesbian venue to see what was going on and we spent the rest of the evening getting to know each other, but I was still married at the time, and nothing ever came of seeing the first lesbian who was interested in me.

All I knew at the time was I was treading water as fast as I could just to stay afloat in the dual gender world, I was trying to live in. One big life jacket which was thrown at me was the attention I was receiving from gay and straight ciswomen. It meant I would never have to approach the potentially unpleasant situation of exploring my sexuality and I never had to go past the point of kissing men at all since most of them did not want to approach me. At any rate, I always thought I was never attractive enough for them, but when I reached an island as I was swimming upstream, I had the chance to pause and realize I did not need a man’s validation to make me a complete transgender person anyhow. There were plenty of fish in my sea and I needed destiny to lead me to one. Which it did with Liz who I later married and have been with well over a dozen years now.

Another thing my stream taught me was to never feel totally comfortable and rest much at all because something would come along and knock me back into the deep water. The problem was I was still catching up on the life that ciswomen grew up living, and it was very complex. I knew it would be, but sometimes I was just caught off guard and think did that really happen.

On the other hand, when I finally was able to relax with all that I had accomplished in my gender workbook, I was so much happier in life. I finally began to realize that I was never a man at all, just a woman trying to live her life from a totally different perspective than most anyone else. Then, it made sense to me why my life was always such a struggle because I had two powerful influences battling each other. The most powerful one had to finally win out, and my inner femininity won out.

If I had it all to do over again, I would have to tell myself to follow my instincts and stay out of the water before swimming upstream became exhausting and I almost went under for good.

I know I have many readers on different parts of their gender journeys looking for any guidance possible. All I can say is that at some point you need to be honest with yourself and decide to take the most natural path you can take. Maybe you can cross-dress enough to keep one foot in the stream and one foot out and that is OK too. I just could not do it that way, but that does not make it right or wrong for you.

For the most part, I still think society is still set up for men to succeed but that is changing. And, when you are a trans person continuing up your gender path, just consider the world is still in flux and the future is feminine no matter long the old white male dinosaurs hang on. Regardless, either way you must make your own way in your own gender stream, and you will have to expect at some point to swim against the current. It is just the nature of the beast we transgender women and transgender men must face in life.

Just be very careful and follow your true gender core and you can make it.

 

 

 

 

 

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 work...