Showing posts with label JJ Hart. Show all posts
Showing posts with label JJ Hart. Show all posts

Sunday, October 5, 2025

Trans Girl on a Cliff

 

Image from Majestic Lukas
on UnSplash. 

A few years ago, sixteen to be exact, I found myself at the ultimate crossroad in my long gender journey.

I was sixty at the time and I had pursued all the mini gender bucket lists I could to see if a complete male to female gender transition was possible, and it certainly was. More precisely, I was becoming successful at carving out a completely new life as a transfeminine person with people who never knew anything about my old male past.

For some reason though, my old male self-refused to let go, causing me undue stress and tension. He kept arguing that there was simply too much hard-earned male privilege to just throw away for good. Plus, once I went down the final path to trans-womanhood, there could be no turning back. The cliff I kept sliding towards was increasingly steep every time I looked at it.

Through it all, I managed to turn a deaf ear to him and looked ahead to a new exciting life which felt so natural. Which is one of the main reasons I did not back down into my previous world of serious cross-dressing adventures. At that point, I needed to assure myself that my new feminine life would be more than adventure, it would be a heavy dose of reality with no turning back to the male clothes still in my mental and physical closet. More than anything else, the new Estradiol hormones I was on helped me mentally to prepare for the new life I was to face, while the clothes in my closet were just waiting for a visit to my local thrift store to give away. It was an emotional day when I severed ties with the last of my male clothes, but I did it anyway and the only thing I saved was my old Army uniform.

Ironically, when I did all of that, I was between serious relationships and all alone in the world to make and live with my serious gender decisions. There was nobody else to discuss my decision with. Just me, all by myself, which gave me wonderful clarity of thought. As the fog of the regular world dissipated, I was able to see clearly down the cliff and determine what the future held for me if I followed my ultimate dream of being a woman. Finally, after the umpteenth time of worrying over my decision, I decided to make it and take the weight of worry off of my shoulders. To ignore the cliff, I was facing, and jump was liberating to say the least. It was like I could breathe again.

As I made the final tumble down my gender path, I remembered all the twists and turns I made to make it. All the times I was laughed at or worse as I learned my lessons I would need to survive if I ever decided to make the final transition. Of course, I knew little to nothing about what I was doing so I was caught making up my woman’s world as I went along, with no help for the longest time. Once I got the help I needed, I was far along in my transgender development in the world, and I used the help I received from my cisgender woman friends to round out my personality and make my jump off the cliff seem easier to take.

With everyone’s help, I jumped and felt as if I could fly in the new feminine world I had chosen. There was no unexcepted crash and burn that I had feared for so many years. I had done plenty of prep work in the major areas I needed such as appearance, communication in the world, and so much more such as what I would do to support myself since I knew coming out on my old job would be impossible. The nights I spent going out in the world by myself as a transgender woman were behind me and I could look forward to a new future. I worked hard to jump from that gender cliff and have a safe landing.

My friends helped me to socialize more at lesbian mixers than I ever thought possible and I was able to retire early on enough of an income, so I did not have to worry about going back to work again, so my main bases were covered. It turned out, all those years of worrying what would happen if I jumped the gender border were wasted as I went all out to make sure I could make it as a transgender woman in the world.

Who knows, maybe all the extra work I did in the world just helped me make the landing I went through a little less intimidating and softer.

Saturday, October 4, 2025

Be Safe rather than Sorry

 

Toxic male from UnSplash

Before I begin this post, I have a disclaimer. I did not follow what I preached many times when I opened my dark gender closet door and ventured out into the public. I broke many unwritten rules I knew were true.

I will say, the times when I came out were much different than today. Not so much kinder and gentler to transgender women and trans men. Mainly, what I am referring to is the person at the top ruining the nation we have, and I don’t have to mention who he is. Basically, he is the top toxic male who empowers all the other toxic males who potentially can give us trouble. There is a real difference in just being laughed at all the way to being physically attacked.

In my case, as I always mention, my initial problem was drawing attention to myself rather than learning how to blend in with other women. I was fortunate I grew out of that phase quickly before I got into trouble other than just being laughed at.

Another of the main issues I encountered was how I was presenting myself once I was fairly confident, I could get by. What I mean was I was going out primarily as a single woman. Which is primarily something ciswomen just don’t do. They believe there is strength in numbers I just did not have. To make up for it, I tried to make sure I did not sit down next to a man if I could help it, and if there just happened to be a vacant seat, I tried to mark it is as mine. What I tried to do was use my cell phone as my major prop. Especially if it was during the warm weather months when I could not throw my jacket over the seat next to me and reserve it. Often, I would act like I was texting a potential friend on the phone who was going to join me. Anything to throw a toxic male off my path.

 I learned quickly when I discovered how much nonverbal communication went on between women that men knew nothing about. One night I had a prime example when a toxic man tried to strike up a conversation with me at one of the places, I was a regular at. When he did, I received a nonverbal warning from one of the bartenders I knew about him, so I rapidly left the venue before anything happened.

All of those methods I used helped me to survive in a new exciting world as I left the gay venues behind me and started to learn what the real world was all about. All very important points if I was ever going to make it to my dream of living as a transgender woman. My learning experiences turned out to be tremendous.

As I said, times have changed today and so much more is at stake for all of us. Whereas a couple years ago, a stranger would be less likely to say anything to you. These days, all of that has changed. There is more pressure on all of us to put our best foot forward as transfeminine people. I always mention the weight I lost when I first came out. Which helped me to buy more stylish clothes and obviously look better. At the same time, I began a very serious skin program which started every day after I shaved. I was doing as much as I could to improve my overall feminine self. All of it gave me confidence to move forward, which I needed badly.

Finally, I would be remiss if I did not mention the loss of your male personal security when you enter a new feminine world. Don’t take chances with your security by doing the things cisgender women already know. To the best of their ability, they try not to park in dark unmarked areas unless they have strength in numbers. As I read, in some areas, women even have to guard their drinks from toxic men trying to drug them. Can you imagine that? Well, you have to when you go through a male to female transition.

This entire post urges you to be on your game when you come out. Among other things, be careful how you carry your purse in crowded areas. It all adds a level of acceptance as a trans woman which goes far past your basic appearance which of course is important too.

In todays’ world, it is important to know your circumstances at all times, not unlike a cisgender woman who learned what to do around toxic males. Look at it this way, you will be a more complete woman ready to earn your place in today’s world.

 

 

Friday, October 3, 2025

No Way to Solve a Problem

 

Image from Babi on UnSplash.

When I discovered my true gender issues that were disrupting my life, I needed to try to solve the problems they created.

In order to do it, I set out on a lifetime journey of discovery. Like most of you, I began my explorations in my mom’s clothes and even tried my hand with her makeup samples. My mirror often lied to me and told me I presented as a pretty girl. Of course, in my pre-teen years before testosterone began to change me, I had an easier time of looking the best I could as a young girl.

When testosterone came along with puberty my problems became real. At the same time, I was becoming better at hiding my collection of feminine clothes I found and was able to buy from my meager allowance. I became very resourceful when it came to my cross-dressing desires, as I even resorted to a cheap Halloween costume wig to get me by for years until I could finally afford to buy one.

As I chased my feminine tail from one close call to another with my family, I wondered why I was cursed with the gender problems I had. In addition, I felt as if I was the only one who had them. I was trapped in a male dominated family who would never understand a boy who deeply wanted to be a girl. My only choice was to keep trying the best I could to solve my problem.

It took me years to realize my so-called problem was more of an opportunity than anything else. But first of all, I needed to face my problem woman to man. No more of my second wife telling me to be man enough to be a woman. It turned out, I was man enough to be a transgender woman, but it was going to be a real battle. By this time in my life, I had accumulated quite a bit of male privilege I knew I had to lose in order to be successful. Basically, for a while, my female self’s main strengths where she felt so alive and natural when given a chance to shine.

As she took advantage of her time in the public’s eye, almost all of my problems seemed to melt away, and I began to feel having the opportunity to experience both binary genders up close and personal in my life was not a problem at all. I just made it one due to my inability to deal with it. I just had too many gender obstacles to overcome. I had accumulated too much male baggage I doubted I would ever be able to live without. It turned out, I could live without most of them, and surprisingly, I could bring some of the baggage along. My prime example was my lifetime love of sports, which I found a group of cisgender women who were as serious about sports as I was, so I was able to fit right in and even have fun.

The new and improved me proved I had lived most of my life as a man as a lie. All the time I spent worrying about wearing dresses and makeup was a waste of time. I had my whole life backwards. My wife was right; I was not man enough to be a woman for the longest time. Once I was though, I never looked back. I can’t say I was prepared for all the changes I was about to make; I was excited about the opportunity I was given to make them. Which most people never get.

It was certainly never a way to solve a problem; I learned the hard way.

 

Thursday, October 2, 2025

If I Had Known Then

Image from Hc Digital 
on UnSplash. 
The age-old question is, if I had known then what I know now, what would I have done differently.

Realistically, since I don’t have some sort of a magical time travel machine, I could not do anything differently. But if I had it all to do over again, I would have tried to come out of my male gender closet much earlier in life. I would have taken advantage of the youth I had and invested it in progressing to being a transgender woman. Even though I was well into my thirties before the term “transgender” was even invented or discussed. The truth of the matter is, I wasted too much time between Halloween parties when I could safely cross dress as a woman. Finally, once a year just wasn’t enough and I needed to open my closet door a little more and explore the world as a transgender woman.

If I had known then, I would have realized there would be no shortcut towards my ultimate goal of living as a trans woman. I would have to find my own unique path to being a woman that any other female has to do. For years, my second wife tried to tell me the truth, but my male ego stood in the way, and I refused to listen. I thought just looking the part of a woman was enough until getting out into the world proved me wrong. I needed to pay my dues just like any other cis woman before I was allowed to play in the girls only sandbox. It was a difficult struggle to get there, full of many setbacks, but somehow, I persevered and kept moving forward, often at the expense of my marriage and my male life. Primarily, my marriage since I was very close to my wife and she was my best friend. If I could go back, I would have tried even harder to be closer to her before she suddenly passed away at the age of fifty.

I would tell her she was my role model and all I really wanted to do was to have her like my feminine self, which she obviously did not. Instead, we fought like cats and dogs until she would tell me to go away and be a woman and spare her the pain. As much as I secretly knew she was right, I was still determined to hold the marriage together and pursue my transfeminine dreams the best I could. It all turned out to be the wrong plan and I suffered. There was not enough therapy in the world to help me through such a cut and dried situation. Sooner or later, I would have to make a decision in my life and choose between my two strong women…my wife and my inner feminine self who was becoming stronger and stronger by the day.

If I had it all to do over again, I would have set my male self aside and det out to build a new life as the transgender woman I was always meant to be. In the short term, it would have been difficult, but in the long term I would have been happier, and my mental health would have been better with the gender pressure off. Also, I need to bring up my excessive use of alcohol to mask my pain. Somehow when I drank, I felt more like a man and less like the woman I wanted to be. It was not until I was well into my male to female transition that I could decrease my addiction to alcohol and now I am lucky if I have two drinks a month.

Even If it is impossible to go back, I wonder how my life would have been if I had pulled the plug on my male life earlier. I certainly would not have missed all the time I was daydreaming my life away about how it would be to live a feminine life. How much better and productive could I have been. On the other side of the coin, I know I would have lost valuable time learning all I needed to learn to survive in such a new radical feminine world. Time seems to always erase the negatives and accentuates the positives.

Even still, knowing how successful I was able to be in my gender transition, it is impossible for me to not think what could have been possible if I had made the move earlier.  Even though my path was difficult enough, I may have had a smoother path if I had done then what I know now.

 

  


Wednesday, October 1, 2025

Just a Man in a Dress?

 

JJ Hart (left) with wife Liz.


Just a man in a dress has been used to describe me in my past.

I suppose it was true to an extent when I was a part-time cross-dresser. But it all changed when I finally grasped the idea, I was so much more than a cross dresser, I was transgender. Ironically, the idea came to me out of the blue one night when I was going out to be alone. As I was applying my makeup and getting dressed, it occurred to me that my life was different. Instead of just wanting to look like a woman, I wanted to interact with the world as a woman. The whole idea terrified me, but I knew if I was successful, my life would never be the same again.

To be successful, I knew I needed to be very careful to blend in with the professional women I had seen previously in the venue I chose for my grand experiment. To scout it out, I went there as a man to get my potential timing down. Once I did, it was time to try to increase my confidence and calm the major fear that I had that I would be called out as a man in a dress. Looking back, I think I sat in my car for a half hour adjusting my makeup, before I gathered the courage to go in. Making a long story short, I was successful and managed to even stay for an extra drink before I left and I was right, I knew my life would never be the same again. I had crashed through my cross-dressing barrier and landed comfortably in the transgender phase of my life.

As I changed, I had the baggage of two worlds to bring with me. One was my past as a man and the second was my experience as a crossdresser. Of the two, my male past was the most difficult to shake, mainly because I had worked so hard to maintain it. I desperately did not want anyone to see I was feminine at all. It turned out I was so successful portraying a man, that everyone I knew was surprised when I transitioned. It was difficult to explain to them I was so much more than a man in a dress, I was a transfeminine person. Then I needed to explain what I meant about that. At that point, I found actions spoke louder than words and they had to see me repeatedly as my dominant feminine self to understand where my life really was.

These days I am so fortunate to be surrounded by people who accept me for who I really am, so much more than just a man in a dress. They shield me from all of the evil stupidity coming down from the orange felon and his minions in the white house. I feel so sorry for the transgender troops who were loyal, qualified members of the miliary who lost their jobs out of ignorance. You all know how I feel about what is going on in Washington, so I don’t have to repeat myself, and ruin this post.

As far as the day-to-day world went for me, I discovered I was remembered easily, so it was not too difficult to begin to build a new feminine person from scratch. I needed to decide on basics such as wearing the same wig and using the same name to get me by. What I was doing was changing wigs and names thinking the process would help me pass magically as the woman I so desperately wanted to me. What I learned was, there were no shortcuts on my male to female transition path. If I was going to make it to my goal of living fulltime as a woman. I also quickly realized, once someone saw me a couple times as my authentic self, they knew I was much more than a man in a dress.

My disclaimer in all of this is, I am not in any way putting myself up on a pedestal and saying I am better than a cross dresser. On the other hand, the opposite is true. I appreciate the time I spent crossdressing. The whole experience taught me so much. Perhaps the biggest lesson was I could make it to my dream of transgender womanhood if I worked hard enough. I most certainly did not think at any point my journey would be as complex as it was. I found to be successful; I needed to be better in life than the average cisgender woman who had huge benefits on me from growing up female. Catching up proved to be difficult to do as my gender workbook was blank. As I always say, I am not taking all of the credit for my success and putting myself up on some crowded pedestal. I found cisgender women to help me.

They realized early I was so much more than a man in a dress and stepped up to help me into their world.

Tuesday, September 30, 2025

Damn its Hot in here

 

Image from Jon Tyson
on UnSplash. 

It is “patch day” for me. One of the days during the week when I change out my Estradiol hormonal patches. Every time I do it, I take the time to remember the changes I went through when I started gender affirming hormones or HRT.

Of course there were the much-publicized changes such as breast growth, changes in skin, and generous hair growth. Very quickly, I was able to put my wigs away and have my own hair styled professionally and begin to use much less makeup to present well. What I did not count on was the internal effects the HRT had on me. All of a sudden, I had emotions I had never had before, and I could cry.

One of the more humorous experiences I had was the night I experienced my first ever hot flash. I was out to be alone that night and was completely caught off guard when the heat hit me. In fact, I had just stopped thinking about how chilly it was in the venue and how I might have to put on my jacket to stay warm. Something I never had to do back in my male years. Suddenly my own thermostat seemed to be ruined, and I was paying the dues for all the times I thought the women around me were just making it up when they said they were cold. Then, I did not need my jacket at all when all hell broke loose, and I felt as if I was on fire. I quickly looked around to see if anyone else noticed my predicament, but no one did. I wondered at the time how they could not, but my heat must have been internal in nature. Later on, that evening, I tried to explain what had happened to me to my cisgender friends and they just laughed me off saying welcome to their world.

Now patch day once a year comes down to my annual mammogram. Since my maternal grandmother passed away years ago from breast cancer, my primary medical provider at the Veterans Administration makes sure every year I have a mammogram to be safe. If you have never experienced a mammogram, there is some brief discomfort but nothing like the alternative. So, I consider it a rite of passage when I have one.

It turned out for me there were many rites of passage to come as I went through a male to female transition. I had taken the appearance aspect of transitioning just about as far as I could and then faced a real decision in my life. Should I seek out a doctor to prescribe gender affirming hormones. I went to my local Dayton, Ohio LGBTQ resource guide and found a doctor and decided to make an appointment to see if I was healthy enough to begin HRT. This was way back in the days before the VA decided to include hormone therapy as a choice for gender dysphoric vets, so the doc I chose was the only logical choice. He asked me a few key questions about what I was prepared to lose of my male lifestyle and then approved me for a minimum dosage of medications to start my journey.

I started on pills and very soon they became a lifeline for a better world for me. Fairly quickly, after I showed no ill effects to the new hormones, I was prescribed larger dosages, and my body took to them naturally.  Then it got hot with my thought pattern of what I was going to do about all the changes which were happening to me. I was appearing very androgynous which was noticeable to others who knew me, so I needed to change my transition timetable because I was running out of time. In short, hormones slammed the door shut on my male life I had worked so hard to achieve. It was mine to give away, and I gladly did it.

Now, as I change my hormonal Estradiol patches out, I stop to remember the old male days and how I felt in my body and say a silent prayer that I have suffered no ill effects in my decade plus journey on HRT. I always take time to urge everyone considering femininizing their body through hormones, to seek guidance from a doctor before you do it. As I have seen the results of unregulated hormone therapy. The process is nothing to play with.

As I look back on the benefits of all the therapists and doctors I have seen over the years (and continue to see), being able to feel the heat of becoming a transgender woman was worth the effort.

 

 

 

Monday, September 29, 2025

Gender Awakenings

 

Image from UnSplash.

Gender awakenings came early and often for me. I say early because from my earliest days of conscious life, I knew something was not right about me. As I always point out, this was in the 1950’s in the dark days of the pre-internet era when any gender information was difficult to come by. To make up for it, I experimented wearing my mom’s clothes and trying to apply her makeup the best I could. Then I would wear out the carpet in front of the hallway mirror admiring myself. Somehow, I convinced myself I was a pretty girl ready to go out into the world.

When I finally broke out of my closet and tried out the real world as a novice cross dresser, I received a rude awakening. Initially, it came from groups of teenaged girls I encountered in the malls I went to. They were brutal and not shy about laughing at me. Too many times, I was sent home wondering what the problem was with my image or presentation as a woman. One thing was for sure; the mirror was lying to me when it told me I could pass with no problem. I just had to do better if I was to survive in chasing my dream of living as a woman. In fact, at times it looked as if I had no chance of ever making it at all.

Fortunately, as dreams went by, I found I had an achievable one as the years went by. But achievable never meant easy. I had many negative transgender awakenings mixed in with just enough gender euphoria to keep me moving. It could be as little as encountering a group of teen girls with no reactions, all the way to having lunch when I went out to shop. What I was slowly doing was replacing my mirror in the hallway with the world. Maybe this male to female transition trip was not going to be so difficult after all.

At this time, over confidence got to me on several occasions when I had left the relative safety of the gay bar scene and tried to move to more familiar venues such as sports bars and even lesbian taverns. The problem was, I became too comfortable when I was accepted and had a tendency to slip too far back to old unwanted male roles. Keeping track of where I was in my new life and taking too many chances. I was guilty of being in the wrong place at the wrong time and nearly suffered from it until I learned my male privilege of safety no longer applied. I also was not prepared for how fast I lost part of my intelligence when I was dealing with men. Very early on, I found myself being completely ignored when I ended up with a group of men. Even though, I knew more than they did.

As I learned I would have a much easier path to acceptance from other women than men, I discovered the hard way that was not always the case. The well documented times when I had the police called on me for using the women’s room at one venue, all the way to being called a pervert in another place come to mind. Those were deep wounds to overcome but somehow, I did and found stable places to go to which accepted me for who I was. Even to the point of protecting me as their token transgender woman. The basics of smiling often, causing no trouble, and tipping well did wonders for me.

Even still, I had to be careful because I had a wife, family and job to come home to after my dream evenings as a transfeminine person. Soon, the delicate gender balance I was trying to maintain became too much to bear. I was to the point where I was just waiting for the next high heeled shoe to fall, or the next gender awakening to occur. I just knew I had come too far to turn back now, and my dreams were within reach. Only my big three stood in my way and destiny was coming along to take care of them.

My wife suddenly passed away, leaving me free of anyone except myself to answer to when it came to my gender awakenings. Plus, the only person I really cared about in my family (my daughter) became my staunchest ally when I came out and I took an early retirement, so I did not have transition on a job of any sort.

Once my gender awakenings started to come, they came fast and furious like a runaway train. The best part was, the whole process felt so natural, I never wanted to turn back.  Somehow, I kept the train on the track.

 

 

 

 

 

 

Sunday, September 28, 2025

Gender Evolution

 

Image from Kyle
on UnSplash.

After all these years of pursuing a male to female gender transition, I view the process as evolution.

I am biased, but I think I have been fortunate to have lived through all the ups and downs of gender dysphoria to be able to have an up close and personal look at how both of the two main binary genders live. Similar to being able to actually live on the economies of Thailand and Germany when I was in the Army during the Vietnam War. By living on the economy, I mean I received off base housing and food pay from the Army, so I went on base only to work. Seeing how other societies work did wonders for my young self.

It took much longer to do the same thing when it came to my gender issues. I knew they were always there from a very young age, but I had no help to discover what my issues really were. I needed to live my life as a transgender woman to learn what I needed to do to achieve my childhood dream of living as a woman. No being a doctor or lawyer for me, I wanted to be a woman. At the time, I was naïve and thought all I needed to do was work on my appearance in the mirror and I could reach my dreams.

As my gender evolved, I needed to evolve as a person with it. What kind of a woman would I become became a major issue. I could be a standoffish bitchy woman, or a worldly feminine being who enjoyed being herself in the world. Ironically, my male self-helped me to arrive where I wanted to be. He had over the years provided me with ciswoman role models to look up to and try to evolve into overtime. When you added a potent mix of male and female into my personality, I ended up with the perfect mix. Even though I was appearing more and more as a female, my old male self-provided me with a firm base to evolve.

One aspect I do not want to underplay is how long it took me to do all of this. As I evolved, I began to make mental mini bucket lists of things I wanted to do in my exciting yet terrifying transfeminine world. The only problem I had with making bucket lists was I was spending too much time in my male life daydreaming of the next time I could be feminine. All too often, my gender lines blurred, and I needed to make sure I kept my male and female lives separate. It was intensely difficult for me to do as I was increasingly discovering I wanted and could pursue a life as a transgender woman I always had wanted to do and still was unable to do because of the male life I had worked so hard to build. The pressure just kept on building as I continued to try new things as my feminine self. I was in an intensely lonely world at the time as I left my closet.

I evolved to a point where I was able to create an entirely new person from the two, I had left behind. I transitioned again from being a basic weekend cross dresser into an accomplished transgender woman who could blend in with the world at large. Suddenly, I went from being shy and backwards to being confident and aware of my surroundings. Which I found I needed to stay safe in my new world. It was then I found many women were curious and friendly towards me while nearly all the men ignored me. Which I had no problem with as I had evolved past caring what they thought.  They had kicked me out of the men’s club.

As I look back at this time of my life, it seems to be a blur of activity.  Since I had changed my gender outlook in the middle of my life, I was learning from watching my new women friend’s what life was all about. Primarily, since most of them were lesbians, I found I did not need the validation from men to feel good about myself as I fit in with them. Evolution felt so good, I wanted more out of my new life. Again, I was fortunate when my wife Liz approached me online and we struck up a love affair which lasts till this day. I never thought I would ever find someone to love me as a sixty-year-old transgender woman at all, but I did.

My final evolution turned out to be wonderful, and I understand now why all the gender bigots hate us so much. We transgender women and trans men have had the chance to do what they never have had the chance to do. Experience both sides of the binary gender experience. The haters will just have to work their way through it. We have evolved and they have not.

 

               

Saturday, September 27, 2025

Transgender Dreams

 

Image from Maximus Beaumont
on UnSplash.

Over the years, I experienced slow progress towards achieving my transgender background which I refused to accept.

What I did to exist with my gender dysphoria was to cross dress when I could, all the way to attending Halloween parties completely dressed as a woman every year. When I did, I could judge the reactions of the public to me. Eventually though, the part-time cross-dressing and annual Halloween parties were not enough. Which led me to explore more and more the world as a novice transgender woman. Being a novice, I suffered too many bumps and bruises as my world changed from male to female. Primarily because my male ego was suffering at the abuse he was taking when he tried to give up control to my long hidden feminine self. He thought wearing ultra short mini skirts would be enough to gain acceptance into a female world.

When just the opposite happened, he needed to grudgingly give up more and more control in my life so I could progress and even briefly thrive as a transgender woman. When I started to look around at other women around me and began to blend in with them, I started to be successful in my life.  In fact, I was too successful at times when I started to be accepted in the world. I began to look for more places to go to see if I could progress my life as a transgender woman. Keep in mind, at that time, living a life as a transfeminine person was still a distant dream. Fortunately, I was receiving enough positive feedback to keep moving.

I discovered most of the world did not care about me, even though I felt all eyes were on me as a woman. Women were looking me up and down to see what made me tick while at the same time, for the most part, men were ignoring me because I was not that attractive. I started to progress in my new gender when I began to have confidence in myself knowing the world could get over it when and if I ran into any problems I could survive. At the same time, I was improving my wardrobe and makeup skills, which helped me to improve my life as a transgender woman. All of a sudden, I realized I could achieve my dream of living in a feminine world, but I still had a long way to go.

Progression began to happen much more quickly, even though I had roadblocks on my path in areas such as communication. Naturally I knew women had an entirely different way of communicating than men. Direct communication was out, and passive indirect communications were in. I needed to learn quickly how to look another woman in the eye and try to judge what she was thinking about me.

Through it all, I had a wife and very active male life to deal with. Neither wanted me to succeed in my dream life.  At certain points of time, the noise of life around me was deafening and neither would step up to help me as I was trying to adjust to a new scary existence. I was alone. I thought. But I wasn’t, I had my long hidden feminine self to step up and help me. She took over as if she had never been forced into the background her entire life. She led me to be the person I should have always been.

I was able to progress through the final steps I needed to make to succeed. The combination of women friends, experience and hormones (HRT) provided me with the final push to shove my male self into the closet for good. Even still, the final decision to give all my male clothes away took a lot of thought. Finally, one night, I could take the pressure no longer and needed to make the move to live my dream. When I did, the pressure was off, and I had a new lease on life. Once I lifted the weight I had carried for so long, I was a new person and had progressed towards my dream. I also wondered what took me so long to make the move. Fifty years of cross-dressing and testing the world was far too long and my mental health suffered because of it.

Finally, I made the choices which should have been obvious to me all the time and decided to reach out and grasp my transgender dreams.

 

 

Friday, September 26, 2025

I am Transgender but I am Me

 

JJ Hart, Mystic Connecticut.

I received several interesting comments on my post yesterday on restroom usage while traveling.

The most interesting one said something to the point that I did not mention I was a transgender woman. I guess because I have been writing a blog which focuses on my transgender journey for over a decade now, I take it for granted everyone knows I am a transfeminine person. Which is wrong. I should never take anything for granted when I write.

The truth of the matter is I have evolved as I have transitioned from the male gender to the female gender. All I know is, everything I ever dreamed of was being able to live as close as I could to being a woman. Over the years too, I have been attacked on what I meant about being a woman with one person even calling me just another old guy on hormones. I felt the comment was humorous and the person who said it was probably jealous, and I moved on.

Much of the problem many people have with the term woman is deciding who gets to have it. Long ago, I realized women were not born into the world, females were, and women were socialized beings which is exactly what I was. I just arrived at my womanhood from a different path than they did which meant I needed to take a different road to acceptance. To do it, I quickly learned not to out myself as transgender, or even try to “fool” the public into thinking I was a cisgender woman. When I became the person, I was always destined to become, I became successful in the world. It is the primary reason I don’t mention the fact I am a transgender woman in my writings.

Plus, I don’t know what the real difference I have anymore when I describe my dealings with the real world if I am trans or not. One point I did miss out on yesterday was mentioning the help and kindness I was offered due to my mobility issues. Thanks Denise. In today’s world, it is rare to be part of strangers offering kindness of any kind. And it is important to note the men on the tour did not step up in anyway to be social, just the women. Which has very much been the story of my transition from its beginning. Women were much more able and willing to let me into their world than men ever were. Again, I was on familiar ground, and I let it all go. With my acceptance from the ciswomen around my wife Liz and I who constantly referred to us as ladies, I did not need any reassurance from any of the men. Or should I say validation.

So yes, I am transgender but more importantly I have followed a very difficult path to be me on mostly my own terms. I went through more errors than trials than I can ever mention to arrive at where I am. I had a late start to be sure when I had no feedback on appearance and building myself as a woman. I made a lot of mistakes to be sure but somehow, I made it to where I could play in the girls’ sandbox.

On the other hand, I helped myself completely when I started gender affirming hormones. When I did, I was able to sync up my inner and exterior selves and have a better understanding of what the world really meant to me. I was so much more than just an old guy on hormones, I was an old guy who was going through some amazing changes as my skin softened, and my hair grew long enough to have it professionally styled. More importantly, the inner changes I went through were more profound as I discovered emotions and senses, I never knew I had. Such as becoming sensitive to temperature and smells as never before.  The whole process opened a new world for me and at the same time gave me more confidence in being me.

It was not until then did I realize how far I had come. To be sure, there is a thin line between me being transgender and just being me. If someone decides to dislike me because I crossed the gender border, it is on them, not me. All I know is, the whole amazing trip made me a better person.

Finally, thanks for the thought-provoking comment. I hope I have answered your question. I am a transgender woman but I am also just me.

 

 

Thursday, September 25, 2025

Restroom Adventures

 

Image from CDC on UnSplash

Since my wife Liz and I went away on a trip to New England for so long, I have several restroom adventures to share.

The main one I did not think of was what would happen when I needed to seek out an open handicapped stall to use because of my mobility issues. I needed all the help I could get to make my way around to get to the toilet.

The first big issue came in Boston, where I was not expecting any difficulties. The first problem came when the only elevator down to the restrooms was broken and I had to try to use a steep set of stairs to make it to the restrooms themselves. I guess I looked unsteady enough for a younger man to offer to help me down the steps. But I made it alone. Then I found the handicapped stall and it was empty. The only bad part was the lock on the door was very flimsy, but by that time, I had no choice but to try it anyhow. In the beginning, all was good, and I finished my business with no problems. Then I heard a mom and young daughter enter the room. At that point, I tried to pull up my leggings and get myself together before BOOM, the kid barged through my stall door before her mom could stop her. Fortunately, I had my leggings almost all the way up as the mom pulled the kid out of there and all was alright. I went ahead and washed my hands and swiftly exited the restroom with a slight smile on my face.

Another one of the positives which happened on the trip was I got a chance to work on my voice again. It turned out I needed a passable voice to get me by in the restroom which on occasion was really crowded. Several times I had to respond to someone inquiring if the stall was occupied. The last thing I wanted to do was respond to another woman asking if the stall was occupied with a man’s voice. I did well enough I guess because no one ever questioned me on it.  Which gave me extra confidence to carry on other conversations with other women on other topics.

No matter how many rest stops the bus made, there still were times when I had to use the toilet on the bus. It was times like these when I was happy, I could sit down to pee. If you ever tried to negotiate moving around on a motor coach, you know what I mean, At the least you have to be very careful and at the worst, you have to be really careful to check the seat before you sit down. Even though I have to give the Amtrak train we took from Boston to Maine passing marks for timeliness and comfort, the restrooms left a lot to be desired and in fact, one seemed to be flooded and out of use. Fortunately, I did not have to go and let another woman take my spot.

Similar to so many other bus trips we have taken, in a relatively short period of time I was accepted for myself and no indication of any pushback of any one on the tour except that one guy on the first day who made the point of pointing me out to his wife From then on, I ignored him and everything was OK. It seems there always needs to be at least on hater these days wherever you go sadly.

Traveling while transgender will always carry extra baggage and we did not even go on modes of transportation such as flying which brings with it a whole other set of potential problems. Once I conquered my rest room fears, I was able to bond with the other women on the trips, and all turned out to be a good move. I made it through mentally and physically, so we have another trip planned. The whole process keeps me challenged and aware of my transfeminine being alive and well. Which is what I need at my age of seventy-five.

The restroom adventures just turned out to be the icing on the cake, it even got to the point when other women were helping me to the restroom. I needed all the cisgender acceptance I could get to build confidence. In fact, I found myself in situations where I was in danger of outing myself. Which is a topic for another blog post. 

Tuesday, September 23, 2025

Back from Vacation

 

JJ Hart at Faneuil Hall, Boston.

My wife Liz and I’s vacation from Ohio to New England was wonderful.

Of course, there were many highlights which I will try to remember and pass along also. but first I needed to conquer my fears of getting along with any potential problems with a stray gender bigot on the tour. I was afraid of losing my restroom privileges. I really don’t know why I feel this way because this was the sixth tour with Liz, and I have been on with no problems. I guess paranoia runs deep.

At the beginning of the tour, I passed another couple on the way to the restroom. Then I got the nudge from the man to his wife to look at me which I dreaded. At dinner that night, we needed to sit in parties of four and no one wanted to sit with us. By this time, I was not feeling good about the rest of the trip and to hell with these other people.

At that time, things started to loosen up as I began to engage with most of the other women. When I did, everything turned out to be in my head. As I began to actively smile and engage with the other women on the trip, they engaged with me. So much so I encountered two occasions when I needed to back off my interactions before I indirectly outed myself. It turned out that one other woman who appeared to be my age told me she was from the same hometown I was from and even went every summer to the same fishing camp for vacation. I was going to ask her what high school she went to, but then I thought better of it because my mom taught at one of the three high schools in town and it was a possibility she could have had mom for a teacher and knew she only had two sons. The other interaction was with a German man who was from Stuttgart, where I was stationed when I was in the Army. I did not want to go deeper with him either and never mentioned I was in the Robinson Barracks area of the city when I was there. One way or another, it turned out to be a small world with those two.

After I had conquered my socialization fears of others reacting to me being transgender, I was able to relax and enjoy the wonderful scenery of upper New England in states such as Maine, New Hampshire and Vermont. Liz and I even had great train experiences from Amtrak, a lake dinner train, and the cog railway which went up Mt. Washington. We were fortunate to have great weather all the way including our trip to the peak.  

Since I needed to take my mobility device with me, which is a cross between a walker and a roller, I learned the importance of finding handicapped accessible areas which there were many. In fact, my mobility issues overcame my misgivings of my being the only transfeminine person around. I was just being me. I only lost the first day of worry before I gained my confidence back that I had as much right on the trip as anyone else.

As I said, we had a great time and enjoyed the diversity and beauty of New England and Boston. I will have several side stories to share with you about Boston and Harvard themselves in separate posts. As well as a post about the unique rest room challenges, I faced.

Thanks for sticking with me in my absence.

Friday, September 12, 2025

'Cation

 

Headed for Maine!

I will be off-line for approximately the next ten days because my wife Liz and I are headed off from our native Ohio on a bus/train tour of Boston and New England.

Mixed in with all the planned activities are my usual paranoias with acceptance and restroom usage. It helps we travel this time through more liberal minded states, rather than the deep south where we went last trip we took. For the record, this is our fifth trip with this company, and I have had no issues with what bathroom I was using, so you would think I could quit worrying about it. But I can’t completely. I just want to relax the best I can and enjoy activities such as a lobster bake (lobsta!) as well as other fun things to do in Boston up to Maine.

Sadly too, I need to rely on having an accepting driver who will help me unload my collapsible rolling walker so I can get around easier. The last driver we had helped me totally and his tip reflected it.

I am also looking forward to having another “lobsta” roll with butter along with a Maine Whoopie Cake which I had when we went up there a couple of years ago.

Most of all, I will miss checking in with all of you every morning with my ideas with how my life as a transgender woman came about. I could take my laptop along but decided against it. Primarily because I think a break will help me clear my mind and do better when I get back. Plus, I know pictures of me are not my strong point, and we are trying to get better on this trip. Maybe I will have more to share with you.

See you in ten days!

Thursday, September 11, 2025

Gender Blockers

 

JJ Hart, picture taken after mixer.

Gender blockers often came fast and furious at me as I lived my life.

First, I needed to figure out how to camouflage my big boned testosterone poisoned body so I could present well enough in the world to get by, once I arrived there. Which in itself was a big enough hurdle to face. Then I summoned the courage to go out of my closet and into the world, I learned the hard way how much further my trip would take me and how many people would try to block me.

At the beginning, it was never easy, especially around teen girls who always seemed to figure me out and have quite the giggle at my expense. Often, it took weeks for me to recover, go back to my cross-dressing drawing board and try the world out again. Fortunately, these were the days when I was attending the cross dresser-transgender mixers and parties in nearby Columbus, Ohio. At these events, often I was able to compare myself to others around me with the same gender issues and see how I was doing with my presentation.  Also, I left the diverse parties I was going to by discovering a deeper understanding of where I possibly was going in my life. I was learning I was so much more than just a man with a hobby of looking like a woman. I kept going back to the fact that increasingly I wanted to be a woman. It was my dream.

Often, my dream was shattered by a number of outsiders. While my wife was very supportive of me as a cross dresser, she completely drew the line at any suggestion I was transgender and had nothing to do with me starting HRT. Then she would team up against me with my male self who was beginning to feel threatened with losing his world. Mainly because I was beginning to have an idea of how my gender dream could become a reality. If my male self was becoming successful in conquering all the blocks and hurdles, he ran into, why could not my feminine side do it too.

At times, my male to female transition process was allow and tedious, and at other times fast and exciting. Frustration would set in when I would try to spend three days a week concentrating on my transfeminine side of life, only to have to revert back to my old male side the remainder of the week. Including my job which was male dominated. The whole back and forth gender life destroyed my fragile mental health and made my life hell, except when I was in my transgender phase. I had too many plates in the air which I was trying to keep spinning. Sort of like trying to keep several girlfriends happy at once.

I could finally take it no longer and needed to try to start removing my roadblocks one at a time. I began with the social roadblock. Could I actually begin to carve out a brand-new life as a transgender woman where no one knew of my past. To my surprise, I found I could. Probably because when I got past the point of thinking I was trying to fool anyone into thinking I was a cisgender woman, I just became me, and I was good enough not to scare anyone away.  One roadblock cleared. The next thing I needed to figure out was how I was going to support myself. Because transitioning on the job was out of the question, I needed to find a different answer. I took so long to do it, the problem solved itself when I got close to a point where I could take an early Social Security retirement and then sell the many collectibles my late wife and I had collected to survive.

With all the gender blockers to my dream out of the way, I needed to push my own feminine self-improvement program ahead. It meant seeking out an understanding doctor to prescribe me gender affirming hormones. When I did, I was able to see and sense a noticeable difference in my external and internal self. My skin softened and my hair grew so I could use less makeup and leave my wigs behind for good. All of which helped me to present better in public. Internally, I could not believe all the changes HRT was helping me with. I was more emotional as my world softened. For the first time in my life, I could cry tears of sadness and even joy.

From then on, I had paid all my dues and was ready to settle into the dream life I never thought I could obtain.

Finally, as a serious side note, it is 9-11, never forget.

Wednesday, September 10, 2025

Change was Coming

 

JJ Hart

As I grew into myself, I learned the truth. Change was coming if I liked it or not.

Change was one of the reasons I loved the fall season so much. As the weather cooled off and football came on, I could go through my feminine wardrobe and see what I could keep and what had to be discarded. Plus, I can’t forget Halloween which of course is the cross dressers’ national holiday in October.

Sadly, as the leaves began to change and fall from the trees, the whole time was bittersweet for me. The worst fall I could remember was when I was on a six-month delay to join the Army and I was working at a small radio station in Bowling Green, Ohio. If you are not familiar with that part of northwest Ohio, it is very flat to the point that any hills are manmade. One night, I was just driving around feeling sorry for myself as I looked ahead to Army basic training and I was so sad as the leaves blew in front of me. If I could have cried, I would have, but tears were nearly impossible for me in my male pre-HRT days. Similar to everything else in those days, I internalized my feelings and tried to move on as deep down I knew change had to happen.

During that time, I almost outed myself to my roommates in the apartment I was staying in until I left for basic. On one trip home, I brought back one of my favorite outfits along with a wig and makeup to Bowling Green. One day when I left, I assumed I had hidden my belongings well enough to not be discovered but I was wrong, and one night when I was preparing to surprise a male visitor to the apartment, after I went to work of shaving my legs and face, I checked for my clothes, and they were gone. I certainly thought, for a while change was coming then it was not. No one said a word to me and very soon, I was off to play soldier anyway so nothing else mattered.

Back in those Vietnam War days, basic training was an intense team building experience when a few drill sergeants needed to try to get a bunch of raw recruits ready for possible combat. During this time, the only way I could keep my girl self-alive was to bury her deeply in my subconscious mind, So, when we were on long forced marches around Ft. Knox, I made sure I thought about the well-being of my girl and the changes we would go through after my military service was finished.

Looking back at the three years I served; the time now seems like a blur and when I was discharged, I came really close to making a big change then by picking my future wife up at the airport cross dressed as my transfeminine self. I even went as far as hinting as such when I wrote her a letter. (Remember those?) Again, my male self-won out and I decided not to, and my big change had to go back to coming again. I did not have the courage yet to face my gender truth and took the easy way out and went back to accepting all the male privileges I had earned.

It was not until I became a parent and had reached my thirties did change to me become a real priority. I will always remember my thirtieth birthday being my hardest because I still hadn’t decided what I was going to do with my life. Sure, I had employment and financial issues to be aware of but again the underlying big elephant in the room was what changes would have to happen with my gender. I knew it was never going to be easy to present well as a woman, and I needed to work extra hard to earn whatever passing grades I could achieve in the public’s eye. Once I made the mental changes to proceed, much of my work became cosmetic in nature.

I was able to move the elephant aside and set about learning what it would take me to really live life as a transgender woman and not just be the “Pretty, pretty princess” my second wife called me. As change set in, I learned very few trans women or women at all live the life of a princess and I had a lot of work to do to put my male life behind me.

The last major change I put myself through was the hormonal one when I started gender affirming hormones. The HRT allowed me to sync up my external and internal selves and live a more productive life as a transfeminine person.

Tuesday, September 9, 2025

Dressing for Success

 

Image from Mohammad Nadir
on Unsplash

During my earliest days when I was forced into being a boy, anytime something negative or even challenging happened to me, I would run home and seek solace in my soft and colorful feminine clothes.

Soon I called the cross dressing I was doing, dressing for success. Mainly because I felt better as I did it. The sad part was, very soon the feelings of gender euphoria went away, and I was back in my unwanted male world where I was expected to succeed. During that time in my life, I was able to barely keep my head above water and still slowly improve my feminine basics in such things as the makeup arts. I guess all those hours of watching my mom apply her “face” as she called it, came back to help me. This was the 1950’s when women took their appearance much more seriously than today. All women were expected to dress for success.

As I barely stayed afloat with my cross-dressing challenges, it soon became more evident to me that there was much more going on with me than met the eye in the mirror as I tried to appreciate myself. It was about that time, when the internet showed up, and I was able to research terms such as gender dysphoria and transgender. Suddenly, I discovered who I might be and certainly found I was not all alone. It all started to make sense why my urge to cross dress never really seemed to go away. It was always with me in the back of my mind.

Soon, as I joined the world as a novice transgender woman, dressing for success largely depended on if I could go out into the world and blend in. I began the easy way by trying my hand with shopping mall clerks who for the most part were only nice to me for the money I needed to spend so I could be more fashionable and feminine. From there, I branched out to challenge myself by stopping to eat lunch and face servers one on one to see how I did. I did well, and very rarely did I have to run home and wonder what I did wrong and go back to my gender drawing board. I did not realize it but what I was doing was replacing my mirror time with time in front of the public. A very valuable learning experience as I discovered venues such as coffee shops, bookstores and even antique malls where I could shop and relax.

Each experience helped me to learn more about myself as a transfeminine person and then dress for success from it. To quit being so flamboyant with my wardrobe and wigs became my new goal as I was settling into my new life. People began to know me quicker, so I needed to be better in my approach to dressing for success. I learned I did not have to lose any of the enjoyment I experienced as a trans woman; I just needed to follow the lead of the cisgender women around me. I did not necessarily have to dress down for the grocery store and up when I mixed with the professional women out for a drink, but it helped me to feel better and relax. Plus, heels and hose would have certainly not worked when my lesbian friends, and I got together.

At times I even took my dressing for success to the extremes to be able to judge what the public was thinking of me. I used to wear my best sunglasses so that strangers could not see my eyes and tell I was looking at them, but were they looking at me? And one of my favorite “props” to use when I went out to be alone was my cell phone which I always had handy when I turned out to be the only woman at the bar. That way, I was trying to show anyone else I had someone else on the way, and I was saving their seat.

To be sure, dressing for success as a transgender woman was always a more complex process than doing it as a man. From undergarments to accessories such as jewelry, wigs and purses, women naturally lead a more layered life which can be reflected in the way they dress. I certainly had many more compliments on my outfits as a woman than I ever did as a man. Primarily, it was because it was something men never do and often, many cisgender women used compliments as simple conversation starters when they were curious about me.

As with all cisgender women, dressing for success is something transgender women must learn. The problem being we come from such a vastly different background to do it. Almost none of trans women had the benefit of peer pressure and a mom to guide us through the initial makeup process. Our workbooks were blank when we started our gender journeys. Playing catchup was not a fun game to play for me as I found making up my face was different than painting model cars. Most certainly, dressing for success was a lifelong experience for me.

 

 

Trans Girl on a Cliff

  Image from Majestic Lukas on UnSplash.  A few years ago, sixteen to be exact, I found myself at the ultimate crossroad in my long gender j...