Showing posts with label trans women. Show all posts
Showing posts with label trans women. Show all posts

Saturday, September 5, 2026

See and Being Seen as Me

 

JJ Hart (center) with Liz (left) and 
daughter (right) 

Yesterday was one of those rare days when I needed to get out in the world and do several errands with my wife Liz.

The errands revolved around going to two of her doctor’s visits she had in one day. That means playing the eye game in waiting rooms for me because I always want to see if anyone is paying attention to the only transgender woman in the room. I am happy to say no one did and I went on with my life.

Since I was only going to waiting rooms, there was no reason to do anything else but dress casually and cool since our temperatures were supposed to reach near the one-hundred-degree mark (F) for the day. So, I chose my lightweight new “The Ohio State Buckeyes” shirt and a pair of leggings for the day since the “Buckeyes” first game is coming up later tomorrow. Also to try to stay cool, I pulled my very long hair back and went with a light foundation and lip gloss.

One way or another no one in waiting room number one paid me any attention as I played a quick “eye-tag” game with them to again see if there was any recognition of me as anything out of the normal.

It was not so long ago that I would have been paranoid about even going at all, but I am happy to say all the old fears are past me now. It is certainly no fun waiting for my wife Liz in a doctor’s office but it is something we do for each other when we can and I need her help when I need to go to the downtown Cincinnati Veterans Administration hospital for an appointment because it always involves a lot of walking which I need help with. It is a great tradeoff for me.

In the second waiting room, ironically, it was my Ohio State shirt which got me into a conversation with a woman who was older than even me. She noticed my shirt and asked if I had any grandchildren who attended school there and I said one graduated and one had just started a year ago. She responded that she had one of her grandchildren who had attended OSU a couple years ago and was a physicist now and I told her my oldest was a nuclear engineer as a civilian for the Navy in Maine and they seem to like it. The conversation was pleasant and made the time go so much faster as she waited for her husband to get through in the bathroom and left before Liz returned.

Speaking of kids, today is my daughter’s fiftieth birthday and I would like to send out my wishes to her as she climbs a mountain somewhere in Maine. All I know about it is, it is on the end of the Appalachian trail. I am so proud of her and my son-in-law for raising such a diverse and successful family which includes one transgender child who is in Maine. She has always been one of my biggest supporters.

It is always good to get out in the world and be accepted as a transgender woman Making myself available to do so has sometimes been a difficult task to take on, but I was fortunate enough to find ways to do it.

I am not sure that there is ever an easy path to living a transgender life and a trans woman or trans man. Genders are so ingrained in us from birth that they are so difficult to change. We get to a point where we try to internalize our truths. Making them an even bigger burden to take on. Now, just being able to interact with another woman on an equal basis means so much to me and takes back to the days when I was just learning to do it. Then, as in now, the secret to doing it was having the confidence to do it. Which for me, was never an easy thing to do because I was always so shy to start with. It seemed to me that once I built my frail confidence to a point where I could enjoy it, something would come along and destroy all my work. Really, it was not until I brought what was left of my of my old male building blocks into my life’s equation, did I begin to see true improvement.

Among other things, he taught me how to stand my ground as a trans woman during the difficult times. Deep down I was learning the life choices I was making were the correct ones.

Which takes me full circle into being relaxed as a transfeminine me in a room full of people yesterday and being able freely being able to talk to a ciswoman about family in another waiting room. I was able to learn the right way to do it from all the girls’ nights out I was invited to where the main topic was not work but was family.

On the other hand, part of me is like our old family cat as he seems to never be totally relaxed. Even when I am in the middle of a conversation like I was yesterday, I was still closely observing the ciswoman I was talking to see if she had any spark of knowledge that I was a transwoman. Perhaps my life experiences will make it impossible for all my paranoia to totally go away.

Best yet, both appointments came back good for Liz’ health, which was a great relief.

In the meantime, again Happy Birthday to my daughter who has been so supportive of me over the years and I hope those of you who are just finding your way long your gender path, I hope all goes well for you and thank you for reading!

 

 

Thursday, August 20, 2026

Burning my Gender Bridges

 

Image from Issiac Viglione
on UnSplash. 

The first time I tried a dress on and put on mom’s makeup, I burned a couple of my gender bridges. Because deep down inside I knew I could never go back.

After a few missteps, I became quite used to it. Even though what I was doing by cross-dressing and building new bridges was quite risky to the only life as a boy I had known, I kept on burning the old bridges and building new ones. Fortunately, the new bridges I was building were the product of better construction than I had ever known before, I still had such a long way to go.

Early on, the problems I faced were simply formed by the lack of experiences I had being a feminine person at all. My gender workbook had never been filled out because I had never been allowed to hang out with the girls and have the chance to understand their lives. There were no girl’s sleepovers for me to go to get peer input into how I was dressing or ideas on how I should apply my makeup. It seemed as if I was stuck forever in my male world and I could not get out.

Another problem I had was I built too many invisible bridges that I did not need to. I was and am a worrier and I routinely build structures just to jump off of them it seemed. That has continued to be a lifetime problem of mine as we can take yesterday’s routine trip to the drugstore as an example. The store is very close to my house but yet I needed to worry about getting there and back in one piece, as well as what I was going to wear and not forget all the items I needed. Of course, I just dressed casually for the trip and it came off without a problem as I got everything, I needed including birthday cards for my daughter’s upcoming dinner my wife Liz and I are hosting her for before she heads off to Maine to climb a mountain to celebrate her 50th birthday. Already, I am stressed about what I am going to wear to the restaurant.

As I matured into a more complete transgender woman, of course I discovered more things to build bridges on or around my life. For the longest time, I refused to face the truth in my life that I was always meant to live in my femininity and leave my male life behind. It was then I started to run, move often and change jobs so I could better support my two women. My second wife and myself. All my building was doing was destroying my already fragile mental self as I desperately looked for answers which were there all along. Anyway I tried to cut it, I should never have been forced into a male box when I was born and had no power to do anything about it.  

It wasn’t until I got out of my gender closet and became familiar with the world as a trans woman, did I really have to begin to burn my old male bridges to the ground. Specifically, when I got out of the gay venues, I sought out some sort of safety and solace in and started testing myself in the real world did I discover how many bridges I had destroyed and how many more would have to go. If I was ever going to have the opportunity to live my dream. I was running as fast as I could in my high heels away from my old male privileges I took for granted until I torched them. Such as sacrificing part of my intelligence and all of my personal safety when I was allowed behind the gender curtain and out of the boy’s club.

The bridge which surprised me the most was when I needed to communicate with the world of ciswomen who let me in and wanted to know more about me. It was a shock to my system to have to actually carry on a conversation or better yet begin one because I did not want to come off as being unfriendly with another person, mainly women. The overwhelmingly group of men as a whole left me alone since they had the sense, I was a traitor to their club. It turned out that if I did not want to burn the bridges between men and myself, they did it for me and they were replaced by the ciswomen I felt more comfortable around anyhow.

When I worked on my male to female transition, the bridges I was building had to be so much stronger than they had ever been before. Mainly because I was risking life as I knew it to do it. Over the years, I had accumulated so much male baggage I needed to figure out what to keep and what had to go so my bridge would carry the load. My baggage included the usual suspects such as spouses, family and friends as well as employment. Again, I was fortunate when I discovered other women with the same interests as me such as watching sporting events.

Lately, I have been receiving comments from readers who are just beginning their gender journeys and the only advice I can give from the other side is to build your bridges well to withstand the changes you will go through. And don’t forget there are many ways to achieve your goal. You can go the surgical route to transform yourself into the person you always knew you should be and go the hormonal route like I did when I was able to thrive with the help of a few ciswomen who showed me my way to build my own bridge into a feminine world. The end result should be whatever feels good and natural to you, you should go with. The one life you have to live should be yours, even if your path to doing it may be a little more different and difficult than everyone else’s. Don’t be like me and take years running from your truth before you face it and win and are able to proudly walk across your bridge.

 

 

Wednesday, August 12, 2026

All Along I was Just Me

 e

Inage from Gayatri Malhotra
on UnSplash. 

It took me decades of living to realize the simplest of all realizations…just discovering who the true me was all about.

It turned out I was so much more complex than the friends I had around me in how I felt about life. Which often help me back because I could not express how badly I wanted to be a woman. What I did was, I took the natural male response I inherited and internalized all my feelings. Naturally, the male response did not work and all it did was wreck even further my already frail mental health. If I could not cross-dress my anxiety increased and when I did my paranoia kicked in when I thought, I was getting caught.

As I added years to my life, the complexity of being a gender dysphoric person grew with the years. What did I do? I tried to outrun my problems. It wasn’t until the Vietnam War years and beyond did I learn that I would have to stop being a victim and stand up to living a life outside of the shadows of being a man. The idea of moving my family around and changing jobs all the time until I finally landed a job I wanted in a location, I wanted to be. That meant I climbed out of fast food and landed in a full service, casual dining chain which served alcohol which was exactly where I wanted to be.

With my dream job in place, I could concentrate on my feminine side by beginning to go to the small diverse LGBTQ parties I used to go to in nearby Columbus, Ohio. At those mixers, I was able to meet transgender mentors who would define my future. From them, I learned a path to my dream may actually be possible. The me I had always dreamed of was finally beginning to emerge. Much to the chagrin of my long-time second wife who actually went with me to a few of the parties. Probably, just to keep track of me. One thing was for sure; my wife never liked the trans woman I was becoming. Back in those days, I was still trying too hard to dress to impress and my wife was right, my dresses were too short, and my makeup was too heavy for her liking.

As she normally was, my wife was right about my appearance, and I tried my best to tone it down when she was around. Most of the time to no avail. I was stubborn and had to live out my so-called adolescence years of cross-dressing before I learned how to dress to blend in with my wife and the ciswomen around her. As I always say, sadly she passed away before she ever got the chance to meet the mature transgender me. I know we could have not stayed married but maybe at least be friends.

The question became, what was I doing with my time when I was discovering who I really was. What I was doing was exploring as close as I could what it would be like to live a whole new life behind the gender curtain. For the most part, I was successful as I made my way from the relative safety of the gay venues I was frequenting and jumping into the more challenging straight sports bars I was used to going to as a man. By never causing any trouble, always smiling and most importantly by tipping well, I was able to establish myself as a regular in several venues which seemed unreachable to me just a short time before. Most importantly, I was able to bring my love of sports from my male life into my female life with no problems. Which was a surprise to me.

As I did, I discovered the true me was not that far removed from the old me. Basically. I had just changed my appearance and gave up basic male privileges such as perceived intelligence and personal safety, and the best was yet to come as I was able to begin to move around freely as the new me in a world run by ciswomen. Quoting my second wife, I didn’t “make” a terrible woman after all. Primarily because I was not “making” anything. I was becoming me. Sure, I knew on occasions I could have done a better job, but I never allowed myself to be a victim and moved on back to my gender path. Which was beginning to change dramatically because I was beginning yet another  major gender related transition in my life.

First, there were the two obvious mental transitions I went through including the initial once when I realized I was so much more than a weekend parttime cross-dresser which went all the way to that fateful night at a local TGIF Fridays when I had had enough of that thought pattern and went out to be with the other ciswomen just getting off of work at a nearby mall.

From that moment on, I knew I could never go back to my old unwanted male self. But still, I felt as if something was missing in my life. It was because I was still missing the obvious transition of all as I finally realized I was never a cross-dresser or a transgender woman; I was just me.

I wish I could take credit for being persistent and intelligent that I kept on pushing to find me but I can’t. That credit goes to all the ciswomen who I became close to over the many years of struggle I endured. And yes, my second wife is included because she was the first to say be man enough to be a woman and make life easier on both of us. As we all know, many women are good at reading small lights inside of a person (unless you are fighting an unsupportive spouse) which is a point for another blog post.

I can’t say enough positive about all the women in my life who helped kick me out of my male nest and into the world of women. They knew me better than I knew me.

 

 

 

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.

 

 

 

 

 

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.

 

 

Monday, July 13, 2026

Gender Binges

 

Image from Andy Arjun
on UnSplash.  

Binge cross-dressing happened a lot to me when I was quite young.

Once I was able to scrape together my meager finances to put together a small wardrobe of feminine clothes that barely fit me, I could not stay away from wearing them more and more. In fact, I was able to come up with two main hiding places away from the prying eyes of my family and most importantly, my slightly younger brother. It was about that time that I really became involved with binging in my new clothes which I felt made me look like a pretty girl.

Very soon, regardless of the risk involved with me cross-dressing as a girl, I was doing it as much as I could get away with. I think now that my mom had to know something about my cross-dressing but was either afraid to say anything about such a complex subject or thought it was a phase that would go away. Obviously, the joke was on her. My wanting to be a woman never did go away; I just matured into it. Plus, back in the late 1950’s and early 1960's, there was very little good information about gender issues to deal with, so we were on our own as gender issues were called mental illnesses. Which even I knew at such a young age was not true. For all I knew at the time, I really liked experimenting with mom’s clothes and makeup and binge dressing was becoming routine.

As I said, once I began to mature into being a more accomplished cross-dresser (even before I considered myself transgender) I managed to dress more and more. I was even able to buy a beautiful long blond human hair wig that she hated and I loved. Finally, after I changed girlfriends, she went away and I kept the most important part of the relationship to me which of course was the wig. It brought me to a whole other level of cross-dressing away from Halloween wigs into the real deal. Back in the 1960’s when miniskirts were in, I could not wait until I could find a chance to slide on pantyhose and miniskirt and top it all off with my blond wig. Yes, I did binge any chance that I got!

Sadly, my binge dressing needed to come to a complete halt during my military years in the Army. Instead of worrying about how short I could wear my miniskirts, I had a more immediate and important problem of how to deal with weapons and drill sergeants in Army basic training. How I survived was that I put all my fond memories of cross-dressing in the back of my head and daydreamed about the future I knew I could have shaving my legs again and binge dressing as a woman.

After I served my time in the military, the only immediate release I had from all the tension I felt to be feminine at all was with all the many and varied Halloween parties I went to. During that time, I went from being a French woman with my blond hair, black outfit, tights and beret, all the way to professional woman one year when I was mistaken for a ciswoman just getting off work. The good news was I was learning a lot, and the bad news was Halloween only came about once a year. I needed desperately to find another way to binge with a purpose and express myself as a transgender woman. A term I was beginning to accept as my own.

Once I began to accept who I was, I needed to set out to prove it to myself and the world that I could live my truth. It was then that my binging took a whole different direction from where I was before. Thanks to the basic acceptance I gained from successful Halloween parties, I had the confidence to know I could look the part and blend in with society as another ciswoman. Little did I know then, the hardest part of my male to female femininization project was yet to come.

It took me finally getting out of the gay bars I regularly went to for some sort of validation I never received and into being accepted as a regular in many of the straight venues I went to and enjoyed as a man. My validation as a regular gave me the confidence to keep trying to improve myself as a transgender woman rounding out her life in the world. As I achieved goal after goal I set up on my trans bucket list, I really binged out every chance that I got which put me into a direct collision with my second wife who did not want to live with another woman and my male self who was dead against giving up his life all together.

By all out gender binging, I had set myself up for an internal war I was fortunate to survive. It took me all I could do to keep all my lives together as the years progressed. All I knew was I was able to carve out a dream existence as a transfeminine person. No one knew of my male past, and I loved experiencing every moment of my new life. Deep down, for once I felt I was fighting my self when I was binging as a trans woman and expressing my true self.

By turning back, the clock the best I could, I tried to take the best that I learned from my male life and apply it to building a solid base for my female life. I think it worked because I was able to decide which of my male baggage was important enough to bring along and I benefitted from being blessed with a long life, so I can see a number of important things come full circle (which is another blog post.)

The bottom line is I have always been an impulsive person which helped me all the times I just had to binge to satisfy my needs. Dealing with my gender issues was just an integral part of that.

 

 

 

 

 

 

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 2, 2026

Gender Evolution

 

Image from Hoite Prins
on UnSplash

Sometimes I think I give the wrong impression when it comes to my reactions to cross-dressing as a whole.

In reality, the last thing I want to do is put myself up on some sort of pedestal because I have survived my own personal gender wars and evolved from a young boy experimenting in his women’s clothes to living full-time as a transfeminine person in the world. After all, I was the one who spent nearly four decades cross-dressing my life away trying to make a final decision on which way my life would take me. So, saying “just a cross-dresser” would be totally wrong for me to do. In fact, cross dressing saved my life from taking off the overall pressure I was feeling from living my gender conflicted life. Just the slightest glimmer of hope I got from the mirror was all I had to get by and I used it to the max.

As I look back from the journey I took from wearing my mom’s clothes when they still fit me, all the way to getting rid of all my male clothing altogether (except my Army uniform), it was quite the lifetime of evolution. Sadly, not all the times were good, but they were all deep learning experiences. Such as all the times I was dressing to thrill myself. Not to properly attempt to blend in with the ciswomen around me. Very difficult lessons to learn as I needed to put my faux teenaged cross-dressing years behind me quickly if I ever wanted to be a success. I was far from being a teen girl since I was in my thirties with the testosterone poisoned body I was working with. I needed to evolve and do it fast if I was ever would be able test the idea I could survive as a transgender woman, leading a successful life.

Suddenly, out of the clear blue sky which was my existence more or less back in those days, something mentally clicked in me as I was preparing to go out into the world one night. As I slipped into my panty hose and heels, put on my makeup and wig, my whole thought pattern changed. I was no longer trying to just go out and successfully present well as a look-a-like ciswoman, I was going out to fit right into their community as a novice trans woman. The thought hit me like a thunderbolt and scared me to even think that way, but I could feel my life making a seismic shift for the better. If I could be successful, which still was a big question.

I am not shy about writing about one of the most exciting nights of my life went I went to mingle with a group of professional ciswomen who worked at a nearby mall. I don’t know what scared me worse, the fear of being recognized as an intruder and embarrassed or the fear of knowing if I was successful, I could never go back to the male life I was starting to evolve away from. I just know I was so scared I thought I would need an oxygen tank to help me breathe when I went in the venue to mingle with all those young attractive women.

You can probably guess what happened from there. I was very successful and knew my future as a cross-dresser was behind me as I had evolved into a novice transgender woman. Complete with two new straight venues I had established myself in as a regular. Something I never thought possible just a few months before when I was frequenting gay venues getting mistaken for just another drag queen. I should be more appreciative towards the reaction I received from the gay community because their attitudes sent me flying to places, I knew and enjoyed as a man. If I had evolved enough as a trans woman to do it.

At that point, my evolution into being allowed behind the women’s gender curtain was forced fed to me quickly. Mainly from other women who I met and wanted to help me adjust to the world I so desperately wanted to be a part of. Sometimes, I was overconfident and was sent back to my gender drawing board when I tried to go too fast, too soon but I never had to go back to the days when I was learning to adjust to the world outside my closet as a cross-dresser. Every angle I pursued in the world seemed to be new and exciting as I learned my feminine lessons well. You might say, I was the ultimate gender sponge because I was finally realizing my gender light at the end of the tunnel was not the train and a good life as a transfeminine person was certainly possible if I kept evolving. All the years of worrying about my future I had wasted in my life were just that…wasted and I needed to move on.

Better yet, I learned the world of ciswomen I was evolving into was worth every bit of the work I had put into it. Sure, I did encounter a few haters, bigots and TERF’s (ciswomen who hated me) but with my newfound confidence I had evolved into, I could quickly ignore them and get along with my life. If I got to the point where I ever needed my new friends to step up for me, they would but I had made it to the point where I could fight my own battles if I needed to.

In many ways, I see the evolution of transgender women and transgender men as the future as now the genders seem to be blurring for the younger generations. Maybe when the old white men finally die out, their bigotry will die out with them. Right now they are scared of the potential a trans tribe carries to understand what goes on both sides of the gender coin and we will be allowed to evolve back to where we were with native American cultures which honored us. But that is an evolvement topic for another time.

Thanks for reading!

 

 

Monday, May 11, 2026

The First Time

 

JJ Hart

There are plenty of first times in a person’s life that we can set up on a pedestal and remember. Such as, the first time you had sex or the first time you drove a car can create some memorable experiences.

I venture a guess that we transgender women and transgender men have more than our fair share of first times to look back on. I know I do. For example, I remember vividly the first time I went exploring in my mom’s garment drawers, and deep down something clicked inside me that I was on a new and exciting path I could never get off of. I also remember the first time I drove a car on a country road at the age of fourteen when no one else was around and I remember the first time I had sex with a woman, and she told me that I would never forget her and she was right.

For many reasons, these were the easy firsts to remember other than times such as when I was in the delivery room for the birth of my only child and negative ones such as when I needed to go to Ft. Hayes in Columbus, Ohio for my draft induction physical. Standing in a room full of naked men was not my idea of fun and a first time I did not want to revisit. There were also lesser first times such as graduating college and receiving my honorable discharge from military service that I was proud of but not as much as I was when I started to fill out my gender workbook and begin to advance towards a stable transfeminine future. It was only then that I began to grasp the importance of life’s first times that I was sometimes racing past before I even knew it. I was so bad about not living in the present and appreciating it for what it was. I was always thinking about the future before the present was over.

When I began to search for my feminine self in the world, I needed to stay in the present more than I had ever needed to in the past. If I did not, I would forget what I was trying to do that night as far as being a novice cross-dresser or transgender woman. I could be mirror-ready with my clothes, makeup and hair and still destroy that image with the wrong movements if I became too careless and forgot where and who I was. Who I was, was the most important time of my life as for the first time, I was attempting to see if I could (against all odds) survive a dream run towards my goal of living as a trans woman in a world of ciswomen everywhere.

As I did become successful, my mindset began to change, and I started to think of myself of a transgender woman more than some sort of a casual cross dresser. I knew it was completely a mental move but still a very important one as I scaled the steep walls of my gender path. At the time, the term transgender was just being used more and more, and for the first time in my life I found something that really described who I was. All those years I had gone to those “Tri-Ess” cross-dresser social mixers were wasted because I still came away with the idea that most of the others were not like me. It took me a while, but I finally began to appreciate the individual that I was for the first time. When I began to remove the cross-dresser word from my mental vocabulary, I was beginning to insert the use of woman and inwardly began to refer to myself as a she, became a milestone in my existence because I was coming to the point of understanding for the first time, I was a woman. Just one with a unique background which should be celebrated, not scorned.

My only problem I had with the whole direction I was heading in my life with my feminine self was that the potential I had to hurt others I loved in the process. And if I had followed my instincts and done the male to female transition, would I had been better off in the long run. For the first time in my life, I felt as if I was wasting my life as a man. What was left of it was only the physical image I presented to the world when I worked and when I was around friends. I was still under the impression I needed his male privileges to exist in the world which were nice to have in the short term but had to go for the first time when I decided to transition into a new, exciting transfeminine world.

Not to say the new world did not present constant challenges to not slip back into my old ingrained masculine ways from living nearly fifty years on and off in that world I was born into without a choice of getting out of. It seemed I was in a dark closet I could not get out of until I made more than a few serious efforts such as going out and carving out my own new life with people who knew nothing of my past. For the first time, I made it in a world full of ciswomen who saw nothing wrong with me being behind their gender curtain and it was as if I had always belonged to the new world I was in. Which was true, I had never been able to get there until I took chances and made the effort. Of course, back in those days, the world was in essence a kinder and gentler place with people less inclined to be in others business.

In my male life, I had always been quite guarded because I did not want anyone in my gender business. As I went female, everything changed and I did not mind anyone knowing my big secret. I was a woman of a transgender background, and I found people who respected me for my honesty on how I was living my life. For some reasons, especially lesbians who let me into their world, and socialized with me as we were regulars watching sports in a few big venues and regulars for the first time at lesbian mixers, I was invited too. In fact, often I was a better “mixer” at these socials than my friends were. I was having fun for the first time in a long time in my life.

I was moving so fast, I finally had to slow down and think of how far I was able to come with the help of my small circle of friends and my future wife Liz. I needed to work on staying in the present for the first time in my life I had a present worth living for, not just going through the motions.

Thank you all for staying with me through all my experiences, and responding with claps, comments and suggestions. As I always say, without you all, none of this is worth it to me.

 

 

 

Saturday, May 2, 2026

The Last Line of Defense

 

Image from Gayatri Malthroa 
on UnSplash.

Throughout nearly half of a century, my male self-fought the complete transition I made into a feminine lifestyle.

During that extended period of time, I think I tried everything possible to convince myself that I was wrong to want to play in the girls’ sandbox at all. As I mentioned in yesterday’s post, I “purged” many times of my feminine belongings. Leaving me with nothing but my most cherished pieces of girl’s/woman’s clothing and makeup. The makeup was easy because I knew I could always buy more. Perhaps the most precious items I never threw away were the nice wigs I was able to buy and the silicone breast forms which ironically were given to me by a fellow cross dresser who was purging also. Deep down inside, I knew I would need the wigs and breast forms again when my urge to cross-dress returned. As my own personal history told me it would.

It turned out that purging was not my last defense, no matter how hard I tried. In fact, the more I tried not to be feminine in any way shape or form, it seemed I slipped closer and closer to it. Especially when I learned I could dress to blend with most of the ciswomen around me. It was then I learned how natural I felt when I began to get it right and could feel all the gender euphoria I could feel.

What I did continually feel was my masculinity slipping away and I only used it on occasions with my wife in mixed company and when I was working in a high-pressure environment. For years, when I was out in the world experimenting living a new life, I felt as if I was sliding down a steep hill towards a transgender cliff which I had no idea of how I would be able to land.

In all fairness to my second wife, she never opposed me cross-dressing and knew about it when we got married. But on the other hand, completely opposed any idea of me becoming a transfeminine person. Between her and my male self, they made formidable opponents in my life when I thought about living as a trans woman. What made it all worse was when my wife kept saying she did not want to live with another woman and did not agree to that when we got married and I had to agree with her. Putting me in a very difficult situation in my life. I escaped the best I could by sneaking out of the house behind her back at any given time I found to test the world time and again to see if I would be allowed to go back behind the gender curtain. Which in many ways, represented escaping the last defense to staying in the male world I had.

Of course, my wife found out on numerous occasions what I was doing as a trans woman and resisted all my progress. When she did, we had giant battles which she normally won and I tried the therapy route to help me with my gender issues. Therapy helped me in many ways in my life but not so much with my deep-seated gender issues. I was expecting too much when one therapist told me if I thought our sessions would ever relieve my tensions, I would be wrong until I was able to make the final decision on if I was able to be a woman or not. At that point, I had two of the most far-reaching quotes that I ignored which were told to me. One of which was the time I was told I was the only one who could decide my gender future and the second was when my wife told me to go ahead and be man enough to be a woman. I was so sure I could do it my way and it cost me dearly. Especially, in terms of my overall mental health when juggling two genders and two lives at once became too much to handle. I did not know if I was coming or going on which day it was on how I was expected to act.

As many of you know, my second wife tragically died of a massive heart attack, leaving me with only my male self to do gender battle with. His last defenses deteriorated quickly as I became deeply unhappy and lonely and took solace in my inner female self for comfort. She stepped up big time, and very soon when I was not working nights, I was in one of my regular drinking venues seeking company. That was when I discovered I had more in common with the lesbians I met than with any man. Since most of them rejected me anyhow for leaving the good old boys club. I was able to say good riddance and go forward in my life into a world I never thought possible could ever be a part of. I had never really got along well with men in my life, and it turned out nothing had really changed. Except the way I was exploring the world. Finally, as my true self. As I was finding me after all those years of searching.

The last defense my male self-had was when my third wife Liz and only daughter came to my rescue with unwavering support for my final dive off the steep gender cliff. They made the landing very soft, and even easy. More precisely, Liz made me a believer in myself again and my daughter gave me support I needed from what blood family I had left since my brother rejected me, and my parents had long since passed away. Add in the couple of lesbians I always socialized with and I had all the support I needed to succeed in where I had dreamed of going and being accepted behind the gender curtain.

By far, I would be remiss if I did not mention the power of HRT or gender affirming hormones in removing any of the final defenses my male self-had going for him. I could not believe how fast the hormones acted as my body began to change, inside and out. It would take a whole post to describe all the impacts the hormones made to me. In fact, I have my annual appointment with my endocrinologist coming up this week, and with it, the chance to get refills on my hormonal patches.

Maybe I can thank her then for helping me to win my battle with my male self. Since I receive my HRT meds through the Veterans Administration, I always hope nothing changes from the top down with my ability to keep receiving a huge part of what makes me whole. I worked too long to get here.

Thanks again for joining me on my journey and I hope my experiences help you too.

Any comments, claps or subscriptions are welcome and make my work so worthwhile!

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Friday, May 1, 2026

No Laughing Matter

 

Image from Priscilla Du Preeze
on UnSplash. 

I am always amused when someone thinks I had a choice to follow my transgender path. Obviously, they were not there for all the trials and tribulations I had and the extreme harassment I received as I came out into the world. All the times I hurried home crying when I was stared at or glared at by the public before I was able to improve my feminine presentation to the point where I could blend in.

I did all I could to improve my testosterone damaged body by going on a crash diet and did my best to improve my skin by using moisturizers everyday after I shaved before I went to work. Why would I attempt all of that if I thought crossing the gender border was just a choice I could make. The farther I went, the more I had to do to improve. Mainly because it felt like it was the right thing to do.

Perhaps the most important sacrifice I needed to be prepared to make was losing my white male entitlements or male privileges. Even though I did not respect the growing rights that I had obtained through hard work as a male, I needed to keep in mind continually I did not really want them anyhow and there were better days ahead if I ever had achieved my dream of living as a transgender woman fulltime.

Through it all though, I wondered why all this gender turmoil was happening to me. Often when the poor, poor pitiful me aspect of my life was at it’s worse, I would “man-up” and purge myself of most of my feminine belongings. As most of us know, purging does not work for any length of time. All it did for me was make me go out and buy more makeup, clothes and shoes to express my femininity again. A total waste of money, but at least I always tried to build back better following every purge I tried. Finally, I looked back at purging as just another rite of passage I needed to through as I followed along my gender path to success, and I was able to put my transgender victim mentality behind me.

As I grew older and set in my cross-dressing ways, I knew increasingly I had no choice in how I lived my life. I was rapidly going through yet another gender transition from just having a so-called hobby into being a transgender woman. I was doing more than just shopping for more and more clothes and was trying out new ways to experience the world the way ciswomen do. I started doing a portion of the grocery shopping successfully as the new transfeminine me all the way to starting to do all my Christmas shopping in unique situations also. Just to see if I could.

At that point, the things I needed to go through to survive in life became increasingly evident to me. I would need to express myself as a woman and I had no choice but to do it. I also knew the risk I was taking when I thought about losing the male life, I had worked so hard and long to be successful at. What would my daughter think of her new dad was one of the few variables as I knew I would lose my long-term marriage and great job that I had. I needed to know beyond a shadow of a doubt I was doing the right thing, and I truly had no choice but to stay on the course I was on. This is where my transgender humor comes in. Why would anyone ever put themselves through such a life full of turmoil if they ever had a choice. Or, when just putting on a dress becomes so much more than a fun experience, where do you go then?

It is no secret where I went and I had the chance to experience so much more in my life because it is exceedingly rare when a human gets the chance to experience both sides of the binary gender spectrum. The problem is we transgender women and transgender men don’t have a chance to enjoy the trip because of the pressure we put on ourselves to perform behind the gender curtain we chose. If we are not doing it to ourselves, the pressure is certainly on from the public to do it too. Especially these days with the charged anti-transgender political attitude we are seeing from the orange menace in Washington DC, and in many states such as my own native Ohio.

If we can ever get the public at large to understand we trans people never had a choice on the life’s direction we ultimately took, we would come out so much further ahead. Sadly, the path to get there does not seem to be getting any closer for many of us as the things we have to go through just keep on coming. I know for those of you who are still on your transition path or even consider it, it is a major step to take. Hopefully on the way, you can take the time to stop for a moment and enjoy how far you have come. I always thought if it does not kill me, it will just make me stronger would help me along. And on a lesser scale, the old sticks and stones may break my bones, but words can never hurt me saying really applied to me also.

When you are on your path long enough to realize there is no turning back, you will also know you had no choice but to keep going towards your goal. It was never easy, but so worthwhile as you navigated the final blind curves, potholes and stop signs. At the least, you will know you lived a life where you had a choice and made the most of it.

Plus, certainly it was no laughing matter. 

As always, thank you for reading along with my experiences. Any comments, extra claps or subscriptions are welcome!

 

 

 

 

Thursday, April 23, 2026

My Gender Workbook was Blank

 

Image from Marcus Winkler
on UnSplash. 



Somedays, I prefer explaining the trip up my gender path as filling out my gender workbook. Of course, the problem I had doing it was I had absolutely no help. No mother or peer group pressure to tell me if I was doing right from wrong when it came to cross-dressing myself as a girl or applying makeup.

Ironically (as I said in a recent post), knowing my mom the way I did she would have been against me shaving my legs and wearing makeup as early as I did as her secret daughter. I was only trying to get a head start on writing my own gender workbook and trying to catch up with all the girls around me who also were sneaking around wearing makeup and wearing panty hose.

It was fairly easy for me to make up my own workbook rules when it was just me and the mirror to deal with. No matter what I did as far as my feminine presentation was concerned was accepted by my mirror which kept lying to me and telling me I was a pretty girl. Which was much easier before I hit the curse of male puberty and all the changes my body was going through. I was seeing unwanted growth and angles while the girls I envied around me were getting curves. When I went to bed every night, I dreamed of my life being different but of course it never was. I would not get the curves I wanted until decades later in life when I was fortunate to have good health enough to be able to start HRT or gender affirming hormones.

There turned out to be tons of effort I needed to put into my workbook before I could arrive at the point where I could even think about starting hormones. The shortcuts I kept trying to make never seemed to work and usually got me in trouble. When I did find trouble by trying to do too much with poor fashion choices, finally I gained some sense, rewrote my gender workbook and went on to successfully try to blend in with the world of ciswomen as a transgender woman. Looking back, I think that page of my book had so many erase and start over marks that I could barely read it.

When I really began to get serious about seeing if I could be successful as a trans woman was when I desperately needed my gender workbook to help me, but it just couldn’t because I had not put the time and effort into filling it out. I had never given enough thought to how different the lives of men and women really were. Perhaps you remember the book “Men are from Mars and Women are from Venus” which when I read it, I wondered where trans people came from. I did not know yet we transgender women and transgender men get to occupy a special planet all our own with our unique knowledge of both men and women.

As I first began to mature into a more complete transfeminine person, I sometimes discovered my mental gender notes became overwhelming, and I needed to head back home to go over in my mind about what just happened to me. Good or bad, it did not matter. What was most unexpected to me was the amount of acceptance I received in the new world I was in. I had become used to the glares and abuse I took when I went out of the house in my early days and learned the majority of the world did not care about me one way or another. All the way to those other women who encouraged me to be in their world. Nowhere in my gender workbook did I ever imagine such a thing ever happening to a person like me just trying to find a new foothold in the world as my authentic self after all the years of struggling.

Sadly, there were still times when I ran out of ink to write in my gender workbook, and I attempted to purge everything I had accomplished and go totally back to my old safe male world. As most of us know, purges never work, and before I knew it I was out buying more feminine clothes and makeup to femininize myself all over again. By doing so, I finally came to the point of stopping obsessing over how I looked and settled into just being the person I was meant to be all along. I just did not want anything to do with me being a privileged male anymore, I just wanted to live out the long-held dream goal of mine to live as close as I could to a woman.

Even at that point, my gender workbook was different than other trans women friends I had known when I made the decision to live my life without all the major gender realignment surgeries and facial surgeries the others had gone through. I had two comments which described me the best when a transwoman friend of mine said I passed out of sheer willpower and another which came in on a comment and said I was just another old guy on hormones. Both were right in their own ways, and I wrote a mental note in my workbook that I would never be the prettiest woman in the room, but I could be the nicest. As far as the comment on me being an old guy on hormones, I wondered if the commenter was just jealous and it did not matter anyhow because I had always considered my gender to be between my ears and not between my legs and I had made it through life as far as I did with no surgeries at all, so there was no need to risk damage when I was older.

Also, I was fortunate to have been able to have other ciswomen around me help finish my gender workbook to where it is today. More than they ever knew, they taught me how to validate myself as a trans woman and welcomed me into their world. A major accomplishment in my life.

 

See and Being Seen as Me

  JJ Hart (center) with Liz (left) and  daughter (right)  Yesterday was one of those rare days when I needed to get out in the world and do ...