Showing posts with label lesbian. Show all posts
Showing posts with label lesbian. Show all posts

Wednesday, October 15, 2025

Pause and Reflect

 

Image from UnSplash.

Yesterday, as I waited for the doctor to see me, I had a chance to pause and reflect on my long gender journey so far.

In doing so, I had the opportunity to think about how scared I was in the early days of going to the doctor as well as other things. Naturally, I discovered some other things I was trying in the new world I was in, totally over my head at times. On occasion, I don’t think I point out enough how little I had to work with when I started my male to female gender journey. I was from a very male dominated family so there were no understanding moms or sisters to help me. In addition, my body was very testosterone poisoned which meant I had no effeminate body parts to work with, except my legs which I received several compliments on at various Halloween parties I went to as a woman. While I was flattered by the attention, I rapidly became more paranoid. I began to take compliments on my legs by thinking the people left out the part that I had on my legs as I had good legs as a man dressed as a woman.

As I reflect on those confusing days, I wondered how I had continued to persist as well as I did. I guess the reason was because what I was considering doing felt so natural even though it was so scary to me. I spent hours and hours pausing my life and reflecting on where I wanted to go. Too many hours, to be exact as I needed to be careful, I was missing out on my regular life as a man. Even though I did not worry about losing my male life the way it was. I wanted him to go away, but I needed to make sure I did it right. In doing so, I was selfish. I wanted to keep some of my male privilege and transition at the same time. All I did was hurt myself and those around me in the short and long term.

In the short term, I knew had problems dressing my body as a woman. I had the overweight thick torso and broad shoulders to worry about which would not go away no matter how much I attempted to display my legs. I was doomed to failure by wearing too many short miniskirts. My male ego was working overtime, and it cost me many embarrassing moments in the public’s eye before I finally learned my lesson and learned to blend with the percentage of the world I really needed to deal with, which were the other women. It is like the other women I dealt with at the VA yesterday, I made sure I thanked all of them for being there, and they really appreciated it and treated me better. In the past, I would have been too shy to do such a thing.

As I continued to reflect on my past evolution of my transfeminine person, I remembered again how self-conscious I was on my early visits to the VA clinics I went to for care. I was so afraid of being stared at, all the way to being laughed at. Which I never actually was. It took me several years of progress to overcome where I was in life. It took me the visits I made to the venues I went to when I left the gay bar scene I was involved with and moved on after I was tired of being mistaken for a drag queen. Which I had nothing against, but it just wasn’t me.

At this point, I was wondering exactly what to do. Some I have talked to mentioned the “courage” word with me when I thought of going out in the world. On the other hand, I thought pursuing a transgender life was in many ways, my destiny I had been working on for decades. As I reflected, I thought how right I was. From the mirror to the world, I had carefully followed my path and just had to keep doing it. Or, instead of courage, I would never forgive myself if I had never tried to try out living my dream. Especially when I had proved to myself that I could do it. I had a giant inferiority complex concerning my entire life as a trans woman which I had to conquer.

By this time, my doctor was ready to see me, and I needed to return to the reality of today’s world. At the advanced age of seventy-six, I view each annual exam as very important of course. Even though it was invading my time to pause and reflect.

 

Saturday, October 11, 2025

National Coming Out Day

 


National Coming Out Day is today around here.

Of significance to me is the input I was asked to provide in my Veteran’s Administration LGBTQ support group. In the group, there are equal members from the gay, lesbian, and transgender communities. Yesterday, I was asked when I came out.

I said I came out when I was sixty, or sixteen years ago. Then came the questions of how I actually made the decision to come out in the world as a transgender woman. Since my time to explain was relatively short for such a complex subject. I did my best to explain all the nuances of giving up a male life I worked so hard to maintain. Then I needed to try to explain the unorthodox way I did it. I wished for the freedom of having the written word to do it, so I jumped right in and quickly started how I left the gay bar scene and went to the straight sports bar scene, just to prove I could. Making it all concise was an issue but I did the best I could.

Then the questions shifted to how or who helped me on the special day when I decided to give up all my male clothes, start gender affirming hormones and come out. That person was my wife of ten years plus, Liz. They asked how we met, and I said she literally picked me up on an on-line dating site called “Zoosk.” The lesbians in the group enjoyed the story saying it took a good woman to finally help me coming out. Which I said was true.

I appreciated the fact that the LGBTQ group wanted to hear my story, and I tried to mention all of us are different. If you are considering coming out, naturally it is one of the biggest decisions you will ever make in your life. We have to sacrifice family, friends, jobs and more to live our dreams. There is also a new transgender woman in the group who felt safe enough to explain her gender issues last week. Her story meant a lot to me and I appreciated her tears of joy of being able to talk to someone else about her coming out story.

No matter where you are on your coming out journey, hopefully you will have the support you need to achieve your goal. Remember, it is a marathon not a sprint and there may be many bumps and dead ends along the way for you.

For those of you who have come out, hopefully you are able to live your best life. Congratulations! Now with the current anti transgender climate from the orange Russian asset, we need you more than ever before.

 

 

Friday, October 10, 2025

No Addiction...Just Fact

 

Image from Yumu on
UnSplash.

Perhaps many of you went through the same misgivings about our male to female transitions as I did.

First, I felt it was a simple fetish with the new feminine clothes I was trying to wear. Then, when I outgrew the fetish idea along with mom’s clothes, I needed to try to determine exactly what was going on with me and my gender issues. With no help, and stuck in a very dark closet, I felt alone with no one to talk to. Thank goodness for the “Transvestia” publication by Virginia Prince coming into my life by pure accident which gave me hope for the future. There were others like me who wanted to look like women and have mixers with each other. If only I could make it to one, maybe some of my gender questions could be answered. While entertaining, the mixers I discovered which were close enough for me to attend, did not really answer many of my deep-seated questions. Such as why I was wearing women’s clothes as much as possible. Was I addicted to the clothes or was something else going on.

It did turn out that something much deeper with me was going on. It took me years to figure out the truth. Something much deeper was going on with me and my deeply held gender issues which should not have been problems at all, if I had faced up to them. I was not addicted to looking like a woman, the fact was, I wanted to find my own version of being a woman.

Then the real search for my identity began, as I finally had the courage to open my closet door and go out. In the beginning, ever so briefly until I built up my confidence as a novice transgender woman. Ironically, back then, the term transgender had not been widely used. There were only transvestites (or cross dressers) and transsexuals who wanted to have major surgeries called sex changes. Through this period of my life, I had the uneasy feeling I did not really fit into the transvestite or transsexual mold. I was different and still confused. All the diverse parties I attended were not helping me decide where I really fit.

Still, I kept trying to find my way, and I kept meeting more and more people on the gender spectrum at the parties I went to. From cross dresser admirers to impossibly feminine transsexuals, to the occasional lesbian, I was able to broaden my knowledge of the gender world as I knew it and further research where I belonged. By meeting all of them, I was able to determine where I wanted to be in the world as a transfeminine person and go from there. Plus, I did know, once and for all, the simple act of looking like a woman was not an addiction for me. It was a deep issue which sooner or later in my life I would have to face.

At that time, my progress was slow but steady as I made a far-ranging group of acquaintances in the gender community I was visiting. On one side, I was dealing with Ed, a part-time closeted cross dresser who had a crush on Michelle. A beautiful transsexual woman we both knew. I was stuck in the middle of that strange relationship. Trying my best to be understanding. All I knew was, the interactions I was having were not helping me with my issues which once again I was internalizing. The same thing I perfected in my male life which was so bad for me. I finally came to the point where I realized I needed to be my own person as a transfeminine person. I knew for sure; I had the dream of someday living fulltime as a woman. I just had no idea of how I was going to get there. I set out to discover answers to the many questions I had.

Such as, I knew I was not a cross dresser or transsexual. I was transgender looking for my path. Was I gay? What was my sexuality going to be under the gender affirming hormones I was seriously considering taking. It took me many years of searching before I finally received some long-awaited answers. And would I ever have the courage to face who I really was.

I was fortunate as I always mention that a small group of lesbians took me in and pushed me along my transition path. My sexuality did not have to change and that was one big question out of the way. My validation came from other women, not men and that was a fact.

Once I fully escaped my gender closet, I could look around with confidence and know my new transgender life was not built on addiction that I tried to solve, but on the facts, I refused to accept. I was never meant to be a man, and I was living a lie. The problem was I became good at the lie, and it was difficult to give up. Finally, I did learn through all my searching what the difference was between addiction and lie. Not a fact.

 

 

 

 

Wednesday, October 8, 2025

Trans Girl Acceptance Versus Competiton

 

Image from UnSplash. 

As I increased the intensity of my male to female gender transition, I was under the mistaken idea that women were not as competitive as men. Very quickly I discovered I was wrong. As with many other gender specific issues I faced, women compete as intensely as men, just on their unique level.

When I grew out of my teen girl dressing stage and began to blend in with the ciswomen at large in the world, I received my first real taste of feminine competition.  As a  man, I had always thought women dressed for other men, when if fact, they were dressing for other women. Once I got that through my thick head, life as a novice transgender woman became easier for me and I could finally progress in my journey out of my closet into the real world.

As I progressed. I wasn’t totally clueless about the differences between genders. My entire life, I had made it my business to study the world of women in case I ever made it in their world. Little did I know how difficult it would be for me to gain acceptance from the alpha female gatekeepers to the world I always wanted to be part of in the worst way. Perhaps, the most important lesson I needed to learn was how ciswomen competed in life. I had always assumed one shallow fact that women only compete on an appearance level. When in fact, they compete in a very complex layered system.

Maybe you have heard the term “Mama Bear?” It refers to women who intensely support their kids and family as one example of how women compete outside of just looking good. My daughter is a great example of a “Mama Bear” as she goes out of her way to protect her transgender child. There are plenty of other examples I have of women competing on a level which includes appearance. My company I managed a unit for used to throw lavish holiday parties which the women managers would go all out for in their gowns. Of course I was jealous as I was stuck in restricting, boring men’s clothing when I would have loved to have been in one of the fancy gowns. But I missed my opportunity again.

I found out too how women compete to keep their man. In yesterday’s post, I recounted an encounter I had with a less than pleasant woman who came back from the restroom and found me talking to her man. They left the venue quickly and I was left with claw marks down my back. Somehow, she thought I was competing for her man, and I never made that mistake again.

Another example could be the number of ciswomen who have no problem with transgender women or cross dressers as a group, UNTIL gender issues invade their own family and their husband comes home and opens up that he wants to be a woman. Then the real work begins from both man and wife as they try to discuss a gender transition. Afterall, what would the wife tell her friends and family.

The flip side of feminine competition is the wonderful world of cisgender woman acceptance. Depending on who you are asking for acceptance, expect a long journey of approving yourself as a worthy candidate for womanhood. As my wife told me so many times that I made a terrible woman, I needed to find out what she meant because I was beginning to have success in my feminine appearance. In her defense, she was right and until the gatekeepers let me behind the curtain to learn the world from a woman’s perspective. I did make a terrible woman.

Maybe you have known that one special ciswoman or two who have had that seemingly unlimited ability to love and accept the world. It is true that nothing can replace a woman’s love. And I have benefitted from them my entire life. Starting with my own mom, who after three still births kept trying until I came along. Plus, I can’t forget the wives who had loved me in their own unique way while I was on my solitary often selfish journey to transgender womanhood. It was not their fault I refused to face my gender truth.

Finally, it was an assortment of women such as Liz, Hope, Kim, Nikki and others who believed enough in me as a person to let me in to their world. They were my gatekeeps who showed me I didn’t have to compete with other women to be successful in my new life. Acceptance from them was all I needed. When I needed to compete, I could do it on a woman’s level because I had been there and done it.

 

Monday, October 6, 2025

Can a Trans Girl Achieve Gender Parity

 

Image from Buddha Elemental 10
on UnSplash.

The main question I have is, have I ever achieved gender parity as I have gone this far in my male to female transition.

During my earliest days in the world as a novice transgender woman, I learned the hard way when I presented as a woman properly, I lost a portion of my intelligence immediately. Especially when I had the rare occasion to interact one on one with a man. My tow truck driver, for example, is my best one when one night when I first decided to go out on my own, my car broke down on a fairly busy road. Much to my chagrin, my problem attracted a well-meaning policeman, so I had him and the tow driver to deal with.

The first thing they did was huddle together and decide which route was the best way to get my car back to my house…without me. Who was I anyhow? Just a blond that needed help finding her way home, I guess. Then, when I was forced to ride back with my car in the cab of the truck, I found how much intelligence I had really lost. I was forced to act like I knew nothing about how his tow truck worked when in fact I did know a wheel was round and the cables on the truck were very strong. Before the short trip was over, I even found out what lunch his wife had packed him for work. I suppose I should have been happy, nothing out of the ordinary happened and he never seemed to let on he was helping a trans girl.

Through all of my early days of learning the gender parity I was experiencing, I needed to learn to keep my mouth shut around men and try to soothe their egos and the exact opposite around ciswomen. I threatened men and for the most part they ignored me, and women were curious and wanted to know what I was doing in their world. In my life as a man, I had never attracted so much female attention. While I was flattered, I tried my best to learn from all the new interactions I was having because often, all was not at it seemed with other women. When I played in their sandbox, I needed to learn all of their rules to achieve any amount of parity. Quickly I learned a smiling face did not always mean an accepting woman when passive aggression set in. I had one brutal night when I was caught just talking to a woman’s husband when she went to the rest room. When she came back, she was not happy with me and soon after the couple left the venue and I was left with claw marks down my back. Lesson learned.

The older I get, the more I think the reaction from toxic men in society is a reaction to gender parity. More than ever before, women are trying to step up and be the quality leaders we so desperately need. I can use my trans grandchild who uses the they and them pronouns as an example as they just started a job as a nuclear engineer following a graduation from The Ohio State University. They got a job as a civilian with the Navy so I hope they can be successful before the current batch of felons in Washington catches up with them. But that is a topic for another blog post.

One thing is for sure, when you jump the binary gender border from male to female, you will feel an instant change. I could no longer rely on size and bluster to get me by in the world with my male privilege. In order to be successful in the new feminine world I was in, I needed to be better as a transgender woman. I had to study and be comfortable I all the feminine areas such as restroom etiquette. Out were the days of just going to the men’s room and ignoring everyone else and in were the days of looking other women in the eye and smiling. For the most part, gender parity at that time meant being accepted in the world of women. How to start or continue a conversation beginning with an innocent compliment became important to me.

Right or wrong, any gender parity with men faded in importance with me as my lesbian friends taught me how important self-validation was without a man. I knew and my friends knew I was a valued person in their eyes, even though I had come to my womanhood from another path.

As society tries to minimize our importance as women, especially transgender women, it is time to realize the unique circumstances that brought us to the place we are today. And what we can add to our broken society in the future. So, I have achieved gender parity in my own way.

 

 

                                                                             

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.

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.

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.

 

               

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.

 

 

Thursday, September 4, 2025

Why Would I do this to Myself?

 

JJ Hart, Club Diversity
Columbus, Ohio.

Even though it has been years since I have been asked the question which asks why I am transgender, I withheld all my sarcastic comments such as I found my gender dysphoria in the bottom of a cereal box and thought of a concise truthful answer.

The truth is I had always known but was afraid to accept it. In the meantime, I set out on a slow, often torturous process to reach my impossible dream. To all the naysayers I interacted with, I just wanted to say, if I was not serious about switching male to female lives, why would I do this to myself. I knew early on I brought a lot of the problems with the public I faced on myself because of my novice attempts at presenting myself to blend into society with other women. I was coming off like a clown in drag, rather than someone who was seriously trying to jump the gender border from male to female. I was not playing around.

As my old male ego suffered, my feminine ego persisted and finally I did better in the world. I think too, the world took me seriously for the first time and did not have to ask the “why” question. I discovered too, that most of the world was just doing their thing and could care less about me if I could just blend. As I did blend in and began to carve out a new life for myself, the “why” of what I was doing became more personal and pressure packed. I was risking a successful male life I had worked hard to achieve, in order to live a new life which was so scary and at the same time felt so natural. I was having fewer people ask me why I was doing this transgender trip to myself.

Which brings up the question why any of us would transition ourselves if we were not desperate to do it. As an example, my own personal example was all the self-destructive behavior I put myself through including suicide and alcohol abuse. I was a living example of why I would do all of this to myself to be a transfeminine person. I was serious about what I was doing and needed to continue up the gender path I was on.

What helped me too was when I began to see the same people more than once. Since I was easy to remember, strangers began to put a name to my face, and I began to become a regular in several of the straight venues I went to. I just followed my tried-and-true idea of if I was friendly, did not cause any trouble and tipped well, I would be welcomed repeatedly.

The farther I went along my gender path, I began to wonder what sort of a transphobic gender bigot or female TERF would even question why a transgender person does what they do. Such as making all the sacrifices we must make to live the life we desire such as risk losing family, spouses and employment. Slicing off a major part of our life and starting over is intimidating enough without the naysayers questioning it.

On the other hand, there were things I wanted to do to help my feminine transition along such as losing nearly fifty pounds and beginning to take better care of my skin. Suddenly, I had access to more fashionable clothes which fit better, and my makeup was easier to apply. All because I took the time to take care of my transfeminine self. When I did so, even the haters I still encountered needed to get over it because I was more secure in myself. Even though I was increasingly successful in the world as a transgender woman, humans are like sharks, and every now and then I needed to fend off any unwelcome attention I might have attracted.

Possibly, the most important answer to the “why” question came when I decided to seek a doctor’s help and begin gender affirming hormones. Naturally, the decision on HRT was a major one and not a decision to be taken lightly. At the time I started hormones, I was leading a healthy male life which would have to change. I knew all along, I had come too far on my gender path to turn back now and quickly learned I had made the right decision to start HRT. My life blossomed as never before, and I never missed my old male body and emotions again.

By this time, I had married Liz and settled into a transgender dream world I never thought I could achieve. I guess I was to the point of if I could dream it and could do it. Which is a topic for another blog post altogether.  Plus, I had answered the question once and for all of why I wanted to do this to myself. It was fulfilling my own personal destiny.

 

Wednesday, September 3, 2025

Fight or Flight?

 

Image from Anna Deli
on UnSplash.

As a man, fight or flight became very important to me. Primarily because I needed to become the protector of the loved ones around me and myself.

To be clear, I was never much of a physical fighter, but as I grew into manhood, I was not shy of confrontations either. I could use my size and or male knowledge to back off most potential opponents. For the most part, it was a straightforward proposition. Rule, or be ruled.

Of course, when I transitioned from my unwanted male life into a new exciting feminine world, my idea of fight or flight needed to dramatically change, before I got hurt.

Not too long ago, I had a question from one of my readers asking me what the most important male privilege that I lost was. I replied, the loss of my personal security. I found out quite quickly how dangerous men can be to women a couple times right after I transitioned and left myself in compromising situations around toxic men. I was fortunate my second wife was around to bail me out the first time and I was able to spend my last five-dollar bill to pay two guys off to leave me alone on the second. The best five dollars I had ever spent! (There probably should be something to the effect I was cheap but not easy brought up too!)

All kidding aside, escaping these situations taught me valuable fight or flight lessons. Gone were the days of out bluffing other men in potentially harmful situations, and in were the days of planning ahead to stay out of situations which could cause me trouble. Keep in mind also, I was spending most of my time out to be alone in those days, so I as completely alone as a transgender woman. If I passed as a cisgender woman, was I in better shape than if I was read as being a trans woman. There was no good alternative, and I always kept flight ideas in the back of my mind if I needed them. I think one of my biggest paranoias was having some bigot sneak up on me from behind and pull my wig off. Which never happened.

Through it all, I suffered from not having a girlhood to grow up in where I could learn the lessons all cisgender women know. Such as doing their best not to find themselves in dark unlit parking lots alone. Following my close call on a dark city street outside two gay venues, from then on, I had a trans man friend of mine walk me to my car to be safe. It was a different experience to be sure for me, but there was/is safety in numbers when it comes to leaving your male safety privilege behind.

When it comes right down to it, your fight or flight chapter of your gender workbook needs to be filled out quite quickly. I know several transgender women who carry weapons in their purses for protection. Even though I was infantry trained on weapons in the Army, I choose not to arm myself because of the fear of shooting myself. My wife Liz and I have talked about the possibility of buying pepper spray as a deterrent, but we just don’t really go anywhere where we could be in danger of using it. So, we have not acted on any moves to arm ourselves yet. Plus, Liz went through some intensive martial arts training several years ago which she could use. There is a plan for us to use if we have to fight in an increasingly toxic world in which I am just about totally worthless at the age of seventy-five and with mobility issues. Ironically, I have experienced yet another full circle moment in my life as I have gone from a fight-first mentality, all the way to a flight first priority. I guess it comes with the territory of being a senior citizen transgender woman.

Whatever the case is for you, please be careful in whatever path you choose to go as a transfeminine person. Just use your new feminine wiles to help you stay safe just knowing it is a possibly toxic world depending upon where you live. I have an on-line acquaintance who lives in rural Tennessee who has been slowly coming out in the recent months, and by sheer willpower, she has chosen to stay and fight for her existence. It takes a lot of courage to say to one of her neighbors who threatened her job by saying she was transgender, to get over it, but she finally did. And she still kept her job, so it is possible to fight instead of fleeing. As I said, just be careful if you do it.

I think the worse bigots to fight are the Bible thumpers who want to quote scripture to you. I am far from a biblical scholar and can never remember a rebuttal to use when and if it ever happens to me. It never has because I would have to fight not to flee the situation.

 

Tuesday, September 2, 2025

The Same Old Road

Image from Danijel Skabic
on UnSplash. 
Quite early in life, I grew tired of the same old gender path I was on. Although I could not exactly put a finger on what was wrong with me, I knew something was. What is that definition of insanity? When you do something over and over again and have the same results, I think it is.

Also quite early, I thought I was the crazy one because of my deep-seated desire to be a girl when I was being forced into being a boy from birth. Little did I know, I was destined to become a late gender transitioner in life and must deal with my own form of insanity for fifty years, before I had the courage to do something about it and get off the same old gender road I was on.

As I traveled, it seemed like I was getting better than ever at finding every bump, curve and pothole along the way. Possibly, I was attempting to make my male to female journey even harder, just to prove I could do it. As I like to say, my gender workbook was blank and everyone around me could tell it. Plus, when I first began to get serious about trying out my feminine self in the world, the only outlet I had were the annual Halloween parties I went to. Early on I tried to dress sexy/trashy and then after a couple of years built myself up to trying to present as a cisgender woman at the party. Which surprisingly I was able to do way back when I was still into Halloween as my outlet from the same old gender road.

The best part was, I was able to locate side roads along the way as I was able to present better in the world as a transgender woman. The side roads enabled me to explore different rabbit holes and dead ends to see if I could survive in a new exciting environment. When I had the courage to do it, the road actually smoothed out for me, and I enjoyed myself more than I could ever dreamed I could. Even with all new gender euphoria I was experiencing, I still had to be more careful than ever that I did not crash and burn my male life…yet. I still needed him and what he could provide such as all the male privileges he had worked so hard to earn.

One way or another, I was definitely not on the same old road as I continued to experiment with living as a transfeminine person. I made mini bucket lists of the new things I needed to accomplish each day as a transgender woman and set out to do them. The list could be as small as working on a more feminine walk, all the way to going to a new venue I had never been to before as a trans woman. More often than not, I found the world accepted me as just another woman and did not really care. The whole experience was a confidence booster and enabled me to travel roads which were not the same old ones I was experiencing as a man. One of the main road twists I always mention was when I was able to escape the gay venues I was going to and finding other lesbian or straight venues which supported me.

Suddenly, I was having so much fun choosing all the new roads I found, I had a difficult time deciding where I was going to go. I never thought I was any good at road building until those exciting days when I was finding myself in the world. Some nights, I even felt like I was on some sort of a feminine interstate highway with all the interaction I was having with cisgender women I ran into. Sadly, I finally needed to slow down before I wrecked and burnt myself out, but not before I experienced more than I ever thought I could. My dream life was right down the road, if I could just reach it. I stopped, looked around and I found, all those years thinking I was crazy because of my gender issues were wrong, and I should have listened to myself long ago and I would not have to gone down all the rabbit holes I went down and then being stopped at dead end streets to prove to myself I was still the man I never was.

I was never good at auto mechanics as a man, and it showed when I tried to keep driving down the same old gender roads. As a transgender woman, I was able to take the pressure off driving down the same old roads.  

 

  


Monday, September 1, 2025

The Second Time Around

 

JJ Hart (middle) at my first
Girls' Night Out. 

If you are one of the rare human beings to experience a second time around in life, you owe it to yourself and others to live it the best you can.

Being transgender can give you that rare insight into two of the main binary genders which should give you an edge in dealing with the everyday world. Having an intimate knowledge of whatever the other gender maybe thinking of us as trans women or trans men brings out fear in the public's eye. Who are we to possess such a wonderful scope of knowledge anyhow? It is especially bad with the male gender who has such a poor grasp of their sexuality to begin with. I know when I transitioned from male to female, one of my main concerns was my own sexuality. Was I expected to suddenly change my sexual preferences which had always been with women and suddenly start liking men. I even went to the point when I first came out when a straight woman friend of mine told me to buy bananas and practice. I will let your imagination do the rest.

We all know though there is so much more to a gender transition than sex when you set yourself up for the second round in life. I found I was leaving a life as a man where I was mildly successful and entering a totally new world full of women who were able and willing to question my existence in their world at all. Away from men, the women were a complex tribe, and it was difficult for me to be given the access to play with them behind the obvious gender curtains. First and foremost, just looking like a woman just got me in the game and the difficult part was just beginning. I spent hours and hours in the world just learning how to be the new me.

Suddenly, before I knew it, the doors to a totally different world opened for me and I was invited to the girls’ night’s outs. The invites could never replace the learning experiences young girls have when they are in their formative years and they get to go to girls’ overnighters with friends, but they were all I had to attempt to catch up on my gender homework. No chance to experiment with makeup or gossip about boys or other girls.

The main problem was, I had another male life to deal with at the same time. Looking back, I don’t know how or why I put up with all the gender stress and tension I did to make it to my dream. I guess the reason was I did not have the confidence to know if I could make such a major life changing step at all. We all have a lot to lose when we undertake such a step, don’t we? Plus, as I slid towards the idea I could live fulltime as a transgender woman, I was being accused of being selfish. Which made me feel guilty until I finally came to the conclusion I was being selfish. Because I had to save my own life.

As I was accepted into the girls’ sandbox around me by the majority of the women around me, my confidence grew that I could indeed live a second time around life as a transfeminine person. My long hidden inner female took over and surprisingly became a rather social person as I formed bonds with my small group of lesbian friends which was the best of all worlds for me. As I always say, the first and main thing my friends taught me was I did not need a man for validation. Which included my sexuality. All I needed to do was still keep an eye out for the rare bigot who hated me for no real reason. It turned out the haters would have to go through my cisgender friends to get to me, if they wanted to.

At that point in time, I met my wife Liz, and my second time around became easier and easier for me to live up to. I say live up to because I found myself at a point where I always dreamed of being. But I never thought I could make it. Never say never became a reality for me when Liz told me she never saw anything male about me. I was in gender heaven and stayed there until I realized what a heavy burden I needed to face. Here I was with the rare chance for a do over in my life and to not repeat the same mistakes I made as a man.

So far so good I think as I head down the stretch run of my life and I can be thankful for the chance to live two lives regardless of what the gender haters say.

 

Wednesday, August 27, 2025

All I Had was Time

 

Image from Natalia Rabinovych
on UnSplash.

When we are younger, time seems like it is less of a commodity. When we are in school for example, all we want to do is graduate into the world.  For transgender women and transgender men transitioning, we often take time for granted. At least I did.

As I was coming out of my gender closet, regardless of not having much guidance on where I wanted to go to achieve my dream of living as a woman, I took my time. For a while, when I had finished serving my time in the military, the only outlet I had to being out in the public’s eye were the yearly Halloween parties I went to. Finally, I could see the writing on my gender wall and knew I would somehow have to do something, so I did not have to wait another long year to go out again. Time was being wasted.

It turned out, I could not see the forest for the trees, because there was a huge world just waiting for me if I just had the courage to do something about it. I needed to hitch up my big girl panties, not be a victim because of the bigots, and do something about escaping my closet. The problem was, I was always making excuses about why I could not do something as a novice cross dresser or transgender woman. So, what if my ego was wounded when I was laughed at early on, I just needed to go back home and figure out what I was doing wrong and fix it. Time was going by, and I was not getting any younger. Little did I know then, as I was in my thirties, how much farther I would have to travel.

I had my own transgender biological clock I was dealing with. Like any woman, I knew I only had a finite number of years to look my best to try to socialize in the world. All of this happened before I learned appearance was just the stepping off point when I tried to interact with the feminine world. My wife tried to tell me, but I would not listen, and I lost years in my male to female transition to learn for myself what she was talking about. Again, I was spending too much time as a victim wanting my wife to explain what she was talking about and not explaining it better to me. The problem was, I would not have listened anyway, my old male ego was still too strong.

In the meantime, I was getting myself caught up in major gender contradictions. I was spending up to three days of my week trying to learn the basics of being a transfeminine person and then turn around and having to revert back to the old male life I increasingly wanted no part of. It was no way to live and often I felt as if I was one of those jugglers I saw on television when I was a kid, keeping several plates balanced at once in the air. Ultimately, the entire gender back and forth nearly killed me.

My suicide attempt, among other things, woke me up to the fact I did not have all the time in the world. Especially if my self-destructive actions were trying to take it away. If I ever was going to have a chance to achieve my dream of living as a transgender woman, I might have less time than I thought to do it. At that point, I shifted my transition plans into high gear and began to explore in earnest if I could do it at all. Maybe it was my impossible dream. One way or another, I was in my fifties and needed to decide what I was going to do.

As I began to carve out my new life as a transgender woman, I needed to quickly learn what worked for me and what did not. My biggest move was when I worked my way out of gay venues where all they did was perceive me as a drag queen and enter the real world where I needed to prove I was more than just a man in a dress, wearing makeup and a wig. With more than a little help from my inner female who had waited so long to live, I was able to establish myself as a viable person to the public. As my trans woman friend Racquel said, I passed out of sheer will power, which I did. I proved I was not trying to fool anyone into thinking I was someone who I was not. For better or for worse, my friends knew they were dealing with a unique woman who had used her lifetime to arrive at the same point as they did.

Maybe I had spent my time wisely. One way or another, I learned a lot about the binary genders as time flew by. 

 

Pause and Reflect

  Image from UnSplash. Yesterday, as I waited for the doctor to see me, I had a chance to pause and reflect on my long gender journey so fa...