Showing posts with label male to female. Show all posts
Showing posts with label male to female. Show all posts

Thursday, October 9, 2025

I Almost Waited too Long to Transition

 

Image from Lizgrin F 
on UnSplash.

I almost went too far when it came to not deciding to transition from male to female in my life.

During the previous half century of cross-dressing my life away in the mirror, I put off making my final decision so many times. One of the main problems was, I was sixty years old and was forced to consider my mortality, which I had always taken for granted. Plus, another issue I had was feeling just a little too comfortable with all the male privilege I had struggled to build up in my life. Often it seemed, destiny had stepped into my life to guide it a certain way because I was very self-destructive and selfish. So much so that my mom always said I had a guardian angel riding with me when I did stupid things behind the wheel. All along, of course, I was trying to hide the pain of hiding who I truly was.

On the other hand, I was basically an impulsive person who felt all rules were temporary and could be worked around. Such as my time in the Army when I was able to land a job with the American Forces Radio and Television Service (AFRTS), which was nearly impossible to do. In the meantime, I was facing the biggest struggle of my life as I needed to figure out what I was going to do about my gender issues. It was always the elephant in the corner of every room I was in.

What I decided to do was research as much as I could my dream goal of living a life as a transgender woman. When I did, my very real struggles began. Early on, nothing came easy on my gender path. I was being laughed at when I went out in public as a novice until I got it right. As I fortunately exited that portion of my life, I was able to see more clearly what I was up against, and it was daunting. I had very little idea of the layered lives ciswomen lead as compared to men. When I realized what I was up against, I needed to set my transition timetable back. And to make matters worse, my male self was becoming increasingly successful in his life. Building up a solid base of marriage, family, friends and job. How could I ever replace all of that and when could I do it.

The only recourse I had at the time was the worst one I could consider. Internalize my deepest gender thoughts and keep trying to attempt to do the best I could to survive a life caught between the two main primary genders. Three days as a trans woman and three days as a man was killing me and I tried to no avail to take the extra day off to relax. It turned out I could not because all I thought of on my supposed day off was what I was going to do the next time I went exploring the world as a transfeminine person. Which brings up a good point, during this time of my life, any thoughts I had that I was just a cross dresser were slipping away. Only to be replaced by the fact that I refused to accept. I was more a woman of my own making than I ever thought.

One way or another it was in my fifties when I began seriously researching the word transgender and what it meant to me. I was happy when I finally found the terminology which applied to me but again what was I going to do about it. I was not getting any younger. I still made the worst of all possible choices and continued my path of least resistance. At least that is how it appeared to the outside world which I was effectively hiding my efforts of femininizing from them. I had won my award as a strong male role model with a good marriage, family and job, and now I wanted to give it all back for a radical gender change into womanhood.

When my sixtieth birthday rolled around, I finally decided I needed to make a major change before it was too late. I went to a doctor and took the steps to be approved for gender affirming hormones or HRT and the real changes started. As good as I felt though, I could not shake the sorrow I had from moving permanently away from my male life. Even after my mental health improved.

Finally, I realized I had waited too long for the change and should have had the courage to do it long before I did. But at least I managed to make the major gender change I did before it was too late. And what about my elephant who was my constant companion? I set it free.

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.

 

 

                                                                             

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.

 

 

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.

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 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.

 

 

Monday, September 8, 2025

Gender Dreams

 

Image from Greg Pappas 
on UnSplash.

This morning when I woke up, I took a moment to remember the sadness I felt when I got up in the morning and I was not a girl. I had the same sad realization, I was still a boy and nothing had changed. Plus, it is important to point out that I had no other dreams when I was young such as being a professional athlete or a doctor. All I wanted was to be a girl. I figured I was the only boy in the world who felt that way.

It was on those mornings when I needed to realize I was still male, and I had a long trip to make if I ever was going to change it. As my life became more complex, so did my gender dreams. Sometimes, I could not wait until I went to sleep to see what sort of dreams, I would have that provided me a respite from the days activity of being a man.

It was not until I decided to come out of my closet and test the world as a transgender woman, did my nights began to change. Replacing dreams with action was often a very scary proposition. But it was one thing I had to do if I was ever going to see if I could make it to a new transfeminine world at all. Would the public ever come to a point where they would accept me as more than just a man in a dress. Out in the world to be laughed at. If I could never make it past that point of being a cross-dresser, did I want to go on any longer and forget all the dreams I had. I finally discovered there was much more to being a woman than appearance and it was just my male ego trying to influence me.

Still, as I struggled along in my novice cross-dressing years, my gender dreams began to change with it. Instead of just wanting to be a woman, I started to dream of how it would be to live as an attractive woman and not have to worry about my presentation so much. I think it was because I was becoming more confident in myself, and my subconscious self was adjusting to the new me. More or less, I was reacting to the kinder, gentler world I was in as a transgender woman, and I loved it.

My main problem then was, could I make it to my dream when it became a reality. I was frustrated when I thought I could see the finish line and it was taken from me due to unknown transitional experiences such as what would I do about supporting myself if and when I made the decision to go from a male world to a female world. And would I need to prepare to be lonely the rest of my life because the possibility of someone loving and accepting a trans woman were exceedingly rare at my age of sixty. I was fortunate and exceeded all my dreams when I was financially able to take an early retirement and support myself and found my wife Liz (or she found me) on an online dating site. At that point forward, I had painted myself into a corner and I had no real reason to not follow my dream of being a transgender woman full time. Because I had finally faced up to myself and realized I had always been trans parttime, even though I could not share it fulltime with the world. 

As I faced up to reality, my nighttime dreams began to change also. Slowly my old male is disappearing from my subconscious too, He is being replaced by new dreams with me living as my true, authentic self. Maybe it is because he was pushed out of his final hiding place in my mind. Whatever the case, I was not sad to see him go.

I wonder now, what my childhood boy would think if he could see me now. Doing much more than just hiding in a gender closet waiting for brief moments to escape and explore. I am sure he never thought he would have the ability or confidence to be who he always wanted to be. Not an athlete or a doctor, just myself…a woman. I certainly had to come a different direction to claim my prize but maybe by doing so, I appreciate it more because it was never just given to me.

The boy I was would have never known his dreams would have never turned out like this, and being happy would not have been so far away also when she was playing with the girls. Where she always belonged.

Sunday, September 7, 2025

Off or On the Transgender Highway

 

Image from David Valentine
on UnSplash. 


When I seriously pursued my male to female life as a transgender woman, along the way I was fooled into thinking I was on a smooth fast interstate highway.

What happened was I was stuck on slow-moving two-lane gender roads and going nowhere for years. Plus, I needed to keep an eye out for potholes bumps and sharp curves. Too many times, I led myself down dead-end streets when I transitioned. The entire process just slowed me down and I lost decades in the process. Then I discovered one of the main problems I had was my old male self was exercising too much influence on my life. My main example I always use were the ill-advised fashion choices I was making when I tried teen girl outfits in my thirty-year-old testosterone poisoned body. I was guilty of not looking around and noticing what other women my age were wearing or what I could wear to disguise the defects I inherited with my body. Even though I was always going to be a big woman, there were plenty of other women my size to blend in with in public. While I am not a huge proponent of age women’s fashion, I am a proponent of looking good and not shocking the world.

One way or another, as I was able to put most of the fashion mistakes behind me, I was able to speed up a little and enjoy the new small gender towns and cities I always wanted to visit as a woman when I was a man. There were to be no more miserable vacations when all I thought about was when I could cross-dress again in front of the mirror. I was far beyond that point. I had developed the confidence I needed as a transfeminine person to take the next two-lane highway ahead and see where the journey took me. More than anything else, the mini trips taught me I could not go to sleep on my gender journey as I was risking my life as I knew it at the time.

In many ways, I was used to the pressure of discovery all along since it had started when I was so young. I just ended up accepting the pressure as a way of life for me if I was ever going to achieve my dream of living as a transgender woman. It all started with the threat of a psychiatrist visit when I was quite young, all the way to losing my family and job if I was discovered later in life.

Perhaps the biggest mistake I made on my road was trying to internalize the entire process and going through the infamous ill-advised purges of everything feminine I owned. It turned out to be one of the dead-end roads I was facing when I found I could not purge my deepest feelings of wanting to be a woman. In no time at all, I was back on the road and ready to try to get on the gender interstate. Many times, I was guilty of taking the wrong exit and having to go back to start all over again when I made the wrong choice of a venue and tried out a red neck, rightwing venue when I should not have. One time, I even had the cops called on me when I visited one venue, I was not familiar with.

After being told to leave, I quietly did and regained my composure up the street at a place where I knew I would be accepted and got back on the road. Once my transgender life began to speed up, I was able to stay on the interstate gender highway thanks to a lot of help from my cisgender friends who taught me more than they ever knew about discovering myself as a trans woman. More than anything else, they propelled me forward towards my dreams. They validated me to a point where I did not have to hide myself anymore on a bunch of dark deserted two-lane roads and stay on the well-lit interstates. I mention them a lot because without them, I could still be hiding my true transgender self away in my dark closet.

It took me so long to transition, I wore out a couple of vehicles along the way, but I finally did it. Regardless of the naysayers who said I was not trans enough to make it, or I passed as a woman out of sheer willpower. I accepted my life for what is was finally at the age of sixty and did what I should have done years earlier. Stood up for myself and started gender affirming hormones (HRT) which was like getting a new sports car to drive on the gender interstate. Again, I was able to leave a lot of negative people behind and live the dream I always wanted to live, as a transgender woman.

 

 

 

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.

 

Sunday, August 31, 2025

Long Labor Day Weekend

 

Image from Anna Storsul
on UnSplash

Labor Day weekend is upon us in the United States which gives us an opportunity to take an extra day off and think about what got us here and how close we are coming to losing it.

Even though I have never been in a union myself, I am an amateur historian and know what unions did to transform this country. All you need to do is some basic research on how bad working conditions were in the steel industry as well as coal mining and elsewhere to see what unions brought about. So, on Labor Day, I salute them.

Elsewhere, the weekend this year features some beautiful weather with sunny blue skies and very low humidity for a change around here in the Ohio River Valley (Cincinnati.) Of course, the early fall like conditions won’t last forever and soon we will be back into summer’s last call. In a couple of weeks, my wife Liz and I will be headed for the East Coast, Boston, Maine and more so I am hoping for the reasonably good weather to hang around until then.

By now, you may be asking what does any of this have to do with being transgender? The answer is it has everything to do with being myself as a transfeminine person. Since this marks our fifth bus tour over the years of hanging out with other cisgender women waiting for my chance to use the bathroom, I still have lingering paranoia with using women’s rooms which goes back to my earliest days of cross dressing in public. Even though I have not had any problems in the past with anyone else, I still have the idea it only takes one bigot on the bus to ruin my trip. At least, this time we are traveling through more liberal blue states, so I won’t have that to worry about. As I said, my lingering fear is subsiding, so I can concentrate on having a good time and seeing the sights of New England. The last trip we were on a woman asked if Liz and I were sisters, so you cannot get more validation than that.

Closer to home before we leave, tonight we are going to dinner at our favorite restaurant with her son. It is another venue I have rarely ever been misgendered in and have never had any serious problems. It always feels good to just exist and enjoy myself since I worked so long and hard to get here as a transgender woman. The more I can fly under the gender radar in today’s world, the better I feel.

Before we go, I will have to shave closely, apply moisturizer, powder and lipstick before I change out of my The Ohio State sweatshirt and into a frilly feminine top and brush out my hair. All of which are still fun for me to do. Not just something I have to do to present better in the world.

Finishing out the day, it will be time to head home and watch the end of summer Cincinnati fireworks display. The display is always huge and attracts nearly a million people on both sides of the Ohio River. Back in the day, when I was younger and another person, I used to come down every year for the Booms. But age and mobility have caught up to me, taken their toll, and we just watch them on television now. Then let the out-of-control neighborhood idiots set their fireworks off and scare the animals and any near veterans with combat PTSD. Out of the two cats Liz and I have; one hates any sort of loud noise.

As with many other holidays, Labor Day presents yet another milestone in my transgender life. I can remember quite vividly when I used alcohol on holidays to dull the pain of not having the chance to spend them as my feminine self. I was fortunate to have escaped my closet and the control alcohol had on me before it was too late. It turned out it was all in front of me all along if and when I had the courage to reach out and seize my opportunity to transition and just be me.

I guess you could say, I needed to labor to do it, but it was worth the effort. When we toast ourselves tonight with our Margaritas, I will propose a toast to all the work we three have put into to where we are today. And, to all of you, no matter where you are today, have a chance to pause and celebrate the gender journey you are on, or have yet to do. Buckle up! It is one hell of a ride. 

Thursday, August 28, 2025

Gender Immigration

 

L'eggs said it best.


With all the negative publicity being brought to the new immigrants to this country by the orange felon/pedo in Washington, I thought it might be time to connect the dots to my own immigration. A gender one.

My immigration plans began as a vacation. I was tired of the male world I was competing in and taking a break as a cross-dressed girl in makeup was a great way to escape my life. Little did I know, from these humble beginnings, I was starting a lifelong journey which in many ways, I am still on over a half a century later. Had I known, I would have ever attempted to undertake such a radical immigration.

Early on, I was just looking to grab the so-called low hanging fruit of cross dressing. I enjoyed the feel of the clothes, all the way to the thrill of hose on my freshly shaven legs. Then, I slowly began to realize so much else was happening. Increasingly I wanted to be more and more like a girl and started to wonder about pushing my male self out. It was difficult because I came from a highly male dominated family. As I pushed forward, my immigration into the feminine side of life became more intense. I tried my best to acquire new more fashionable clothes and even bought my own makeup and panty hose. Do you remember the “L'eggs” panty hose which came in plastic egg shaped containers which it seemed you could buy everywhere, and is still made today. I learned the hard way; how easy it was to destroy a pair when I unfortunately ran one of the legs. Ruining my outfit.

Progression was slowed by a late-teen collision with serving time in the military due to the Vietnam war. Obviously, I could not bring any of my “stash” of women’s clothes or makeup with me, so I was stuck. No more gender immigration for at least three years of my young life. There were several major positive things which happened for me while I was stuck being a man in the Army. A prime example was all the traveling I was able to do around the world in places such as Thailand and Europe (Germany). The whole process enabled me to keep my mind off my gender issues and set me up with the idea I could outrun my problems. Which, of course, turned out to be impossible. Which should be the topic for another blog post.

After the Army, my life changed again as I entered the world of parenthood. Being a parent of a daughter was an unexpected but pleasant surprise, and my gender immigration was put on hold briefly again. I say briefly, because I discovered my transgender issues ran deeper than I had thought. My presentation as a novice transfeminine person was coming along. My first wife did not care, and I was able to explore my potential future as a gender immigrant at events such as Halloween parties. Each party to me represented a chance to see how I was being accepted as a woman in society.

After a few years, I ended up divorcing my first wife and marrying my second. She also knew about and accepted my cross dressing from the beginning of our relationship but never accepted me being transgender as I immigrated towards being a woman. My male side was like being the Titanic, slowly sinking and then picking up speed with her fighting me all the way. It turned out, the issues I was facing were like the tip of the iceberg. With most of it being hidden from everyone. Including me. She tragically passed away before the final resolution in our relationship was ever decided.

When she moved on to the other side of existence, it was left up to me to decide the future of my immigration. I had certainly paid my dues by taking on all the menial and not so menial work of being a woman. I was on gender affirming hormones and was living as much as I was able as a transgender woman, so I was close to filling out my immigration papers and was ready to go into a world I had only dreamed of. My presentation had improved to the point where I was not the most attractive woman in the room, but I could handle myself to the point where most of the world just did not notice me. So, my immigration was more successful than I ever thought possible.

Perhaps the best part of immigrating was learning to accept and love myself for who I really was. Which meant all the hassles I had over the years as I tested out the world, made my immigration worth it.

 

 

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 ...