Showing posts with label fashion. Show all posts
Showing posts with label fashion. Show all posts

Tuesday, July 22, 2025

A Tale of Contrasts

 

Image from UnSplash.

No matter how you cut it, our gender is a tale of contrasts.

From the earliest age, we are forced into rigid gender roles, who for most people, work out quite nicely because they never question their assigned roles. Then there are those of us who just as early in life begin to question our placement on the gender spectrum. In my case, I knew something was wrong, I just could not figure out what. Then, as I became older, I made the discovery every morning when I had to determine what gender I had to be for the day. A jarring discovery to be sure.

Naturally, since I was born male, I needed to own up to the fact I had to do my best to face the world each day as a guy until I could slip behind my own gender curtain and put on women’s clothes and makeup. Early on, as I lived my limited feminine life in the mirror, I thought appearance was my number one goal towards living my gender dreams. It was not until much later in life did, I began to understand how wrong I was. There were many more contrasts between men and women that I ever dared to think about. Mainly because I was viewing how women live only through rose colored glasses as I thought they had easier lives than men.

It wasn’t until I began to pay my gender dues as a transfeminine person, did I begin to see the reality of what I was looking at if I decided to transition. As I was making my way into what I call the girl’s sandbox, I was getting tested regularly to see if I belonged. On some days I was successful and happy and on others, I was getting beat up (or clawed) and needed to retreat before I came back for more. One thing was for sure, all of this testing from other women was doing me good, because I never quit trying.

The main thing I did learn was one that I vaguely knew, women had their own world away from men and had their own alpha’s who ran the show. Once I was accepted by them, the rest of my life as a transgender woman was so much easier. But, on the other hand, the testing process was so much harder because the alphas were so much more wary of me wanting to be in their world. My second wife was an alpha and she made sure I worked long and hard to even try to earn a spot in the sandbox. An example was one of the many times she told me there was so much more to being a woman than just looking like one and it took me years to understand what she meant.

Perhaps the second most difficult part of being accepted in the feminine world was being able to communicate with other women. Out were the days of trying to bluster my way through a conversation and in were the days when I needed to look another woman in the eye and appear to be less threatening. While at the same time having eyes on my back for a passive aggressive attack. I learned the hard away on that to never trust a smiling face completely.

As I learned to communicate with other women, my life in public became so much easier and I could begin to relax more as I was beginning to put my entire feminine picture into focus. I could forget about completely focusing on my looks and movement and could concentrate on being social with the world. Which was important to me since I had always been a socially active person. Plus, as I always mention, men were never much of a factor to me since most of them ran and hid from me completely. Which was OK since I did not really know how to handle them as a transgender woman either.

My life of contrasts was coming to an end when I entered the final chapter with gender affirming hormones or HRT. The hormones were magical when they started their changes on me. I think most people consider external changes such as skin, breasts and hair to be important, and they are but to me, internal changes were more important. In a remarkable short span of time, I became more emotional as my world softened. Making me into a complete person.

I am biased, but I think my tale of contrasts made me into a better human being as I could understand both binary genders better. Since I had lived in both. Plus, after having the chance to live as both, I made the right choice to live as a transgender woman, even though at times, it was an intensely lonely and difficult journey. Which could be another blog post.

Sunday, July 20, 2025

Can You Ever Enjoy the Ride?

 

Image from A. C. on UnSplash.

Lately, it has occurred to me how often I did not pause to enjoy my gender journey.

Perhaps it was because for the longest time I experienced very little gender euphoria for two reasons. The main reason was, I was never raised to feel any joy in my life. Nothing was ever good enough. So, when I entered the world as a novice cross dresser or transgender woman, life was very tough. The other main reason was, I was approaching my life from the exact wrong way. Deep down I knew when my “buzz” went away so soon from merely dressing up in feminine clothes in front of the mirror, I was doing something wrong. I did not know then my gender issues ran much deeper than just a love of fashion and makeup.

Before I knew it, I was in a vicious gender circle in my life when I needed to dress up rather than wanted to. There was a huge difference. When I needed to cross-dress, I had the tendency to take more chances and jeopardize my life as I knew it because I knew there was no way my parents would ever understand how their son was really their daughter. Plus, there were many other distractions too, such as not being able to afford my own wig until I was well into my college years. I hated running around with a towel on my head fantasizing that I had a full head of luxurious girls’ hair.

There was always something I was reaching for which ruined my present enjoyment. Such as a better dress, shoes or makeup which could help me look better as I had neared an impossible ideal of attractiveness. Facing my reality of appearance when the only feedback I had was in the mirror. As we all know, the mirror has a tendency to lie to you if you are not careful, and I needed a way to test my presentation as a transfeminine person in the public’s eye. Easier said than done, when I was busy living my own down low in a male life I was frustrated to be in anyhow.

Very quickly, I learned the mirror had been lying to me as I was rejected by the public. To succeed with my dream, I needed to pause my life and attempt to find out why I was having all the problems I was having. Almost immediately, I determined I needed to get my male self out of the way. He was dictating how my fashion presented itself and it was all wrong. For any number of reasons trying to dress sexy in the wrong places was getting me into trouble. My guy was dressing me for other guys when I should have been dressing for other women. Once I figured out, I was not a teen aged girl, my public life became decidedly better.

So much better, I was even able to enjoy several of the solo nights out I went on to be by myself. Even though I knew I was a transgender woman, I was just being me, and the public (amazingly enough) was accepting it also. My mirror even came back into play, and I used it more often in places such as women’s rooms to adjust my hair and makeup.

Life then began to roll on very fast. All the way to the point I was having a difficult time keeping up. I was learning so much about the feminine side of life, it was too late to turn back then and more and more, I was discovering how much I loved this new side of life I had always dreamed of.

Also, my life was reaching a new level of complexity as I was shutting down the male side and giving full access to my female side who had waited so long to be free. My problem was I was still trying to live part time in both genders as I transitioned, and I was afraid of what would happen when I lost all my male privileges. Finally, my mental health could take it no longer and I had to jump off the gender cliff I have written about.

As I jumped, the ride down was scary but fun in its own way, not unlike a big rollercoaster at an amusement park, the ride up in many ways was worth the ride down. All the fear and terror I had experienced when I had come out to a close family disappeared when I was accepted by my daughter and my wife Liz and a warm set of relief sat in. I could not wait until I could get back in public and live my true existence out of the closet. I was creating my own universe for a change and not relying on someone else to do it.

I began to build my own female privilege and thrive in it. It continues till this day and is the topic for another day. In the meantime, I often try to pause my life and enjoy where I am in my life.

 

 

Sunday, July 13, 2025

Painting Myself into a Corner

 

Image from UnSplash.

I was always an adequate house painter and not much more.

Possibly my biggest problem was ever finishing a project. Every time I would start, I got bored and quit before the project was done. There were even times when I would unknowingly paint my way into corners. Little did I know, all of this would carry into my life as a cross dresser and later a transgender woman.

Like many of you, I started experimenting with my mom’s clothes which I became attracted to at a young age. It was most likely a carryover from watching mom (and admiring) put on her “face” or makeup as she called it. I wanted to see how the whole girl package worked for me. At that point, I began to place myself in danger of painting myself in a corner I could not get out of. The corner I am referring to is being caught and facing irreplaceable damage to my life as I knew it in a male dominated family. As the oldest son, I was expected to carry on a macho tradition.

The problem was of course I did not want anything to do with male tradition because I was enjoying my alone time cross dressing as a girl so much. I worked onward on my feminine artwork, as I sought to buy my own makeup and pantyhose from my allowance and newspaper route money. Then I experimented with my limited time until I became a little bit better and did not look like a clown in drag. I was slowly finding my voice as a transfeminine woman.

The more I discovered, the more I risked painting myself into a corner. When I was in the corner, sometimes I paused to look around for a reality check. An example was the night I was in one of my regular venues dressed to fashionably blend in with the rest of the women and I needed to discover if I wanted to escape the corner I was in at all. It turned out I loved the real me and wanted more time out of my closet. I was beginning to learn who I really was, but it turned out I would have many more corners to paint myself into. Such as settling into one new person and not changing each time I went out into the public. I was shocked how quickly people remembered me; I needed to wear the same wig as a start to solidify my future in the world as a transgender woman. In a way, the experience was boring because I was always enjoying my newfound ability to shop in wig stores for the so-called perfect hair after waiting all those years to do it.

Another of the major corners I painted myself into was how I ended up just pursuing the basics of communicating with an all-new world. I never expected people (particularly other women) would ever want to talk to me as a woman because they rarely wanted to as a man. My guess is the women were just curious about me wanting to be in their world, or just I did not threaten them anymore when they let me behind their gender curtain.

In many ways, my decision to undertake gender affirming hormones was me painting myself into a corner was the biggest risk I had ever taken. Undertaking HRT was my own ride or die. Either I made it as a transgender woman with the help of hormones would preclude me ever going back to a male life I never asked for, or I would have to find another way out. Spoiler alert: I was fortunate when I cleared the medical screening, I needed to begin what I considered to be lifesaving hormones, and I flourished. My decision could be compared to a gender insurance policy. I was making sure I was successful when I finally synced up my inner and outer selves.

Today, I have put down my paint brush and concentrated on living my life as a supported transfeminine person. Sure, I confuse some people with how to refer to me, but that is their problem not mine. They need to be educated to the world anyhow. Transgender women and transgender men are not their enemy, but their ignorance is. I filled my world with acceptance from a loving world and watched many other people paint themselves into their own corners. I took many risks along the way to do it and out of sheer will power to do it.

I have felt the depths of loneliness, all the way to having a new family all my own (except my daughter of course, she was always there). I don’t think I would recommend such a unique human journey to anyone else, but it was anything but boring.  As a painter, I have finally come close to finishing a project.

 

 

 

 

Friday, July 11, 2025

It's Just Life...Not a Joke

 

Image from Engin Akyurt on UnSplash.

It took me awhile before I finally came to the point in my gender transition when I gave up and thought the whole process was just life and not some sort of an evil joke.

I had struggled enough through the years when my male self-put up quite the struggle to exist at all. It was as if he was on a slippery slope towards losing his life altogether. To make matters worse as I always point out, my male side’s life was not always that bad. I had a long-term marriage, close friends and a good job to fall back on when I needed it.

Through it all, I thought it was only the draw of the feminine clothes which kept me longing for another trip to the mirror. I did not realize my feelings went much deeper than that. I was feeling life itself. It took me many years and even decades traveling a very curvy and bumpy gender path to realize where I was. Plus, many times, when I realized where I was, I became scared of losing everything. Falling off a gender cliff became a real possibility.

No matter how frightened I became, somehow, I kept on moving forward thanks mostly to the brief moments of gender euphoria I was feeling. The interludes helped me to determine if my dream goal of living a transfeminine life was possible at all. Back in those days, I was immersed in the struggle to present well as a woman and not much else. In fact, when I go back and read my earliest blog posts, I cannot believe how much they emphasize fashion and makeup. It all happened long before I needed to learn the layers of life a woman goes through to live her life. It was like my wife told me be man enough to be a woman. In those days I was not as I made weak attempts to live in both main binary genders.

In the short term, I did not understand what my wife meant as I became semi successful in presenting well in the world as a woman, but I had not paid my dues. I found I would have to wait until my wife had passed away before I could earn my way behind the feminine gender curtain to be allowed in by the ciswoman gatekeepers. It was about that time too when I began to understand my dream of ever becoming a fulltime transgender woman could be possible. It was much more than a hobby or part-time profession; it was my life. Then my realization led me to understand what my wife was talking about. I needed to set off on an all-out journey to live my best life as a transfeminine person. I even needed to understand questions about my own long held sexuality. If I lived as a woman, would I suddenly have to like men sexually? I just didn’t know until I set off to experiment.

Along the way, I did manage a couple dates with men which led to kissing but not much else and I did not feel much of a spark of any kind. On the other hand, I was surrounded by curious ciswomen (including lesbians) who wanted to socialize with me, so I was happy, I had always been a contradiction in terms socially, meaning I always enjoyed company even though I was shy and I could continue to feel that way. My life was beginning to come together in ways that I never imagined possible.

For example, I never imagined I would have been able to enjoy a small closely knit group of women friends who taught me more about life than they ever knew. Without any pressure, I was able to sit back and live vicariously through them and primarily how they lived their lives without the validation of men. It was not too long until they began to invite me along to their lesbian mixers, which I loved. I was even approached by other women and kissed. Which provided me with a huge amount of validation.

With my sexuality and life coming together, I could concentrate on enjoying my life on my new gender affirming hormones or HRT. The hormones went a long way in syncing up my internal and external self. Along with softening my skin and facial lines, my whole world was changing too. My emotions heightened as well as my senses as the world around me was softening. A perfect match to my rapidly expanding social life.

I will never know if waiting so long to transition into a feminine world was worth it or not because I had so many excuses why I never had done it. All I really know is, I did it before it was too late and have never looked back. That’s life.

 

 

Tuesday, July 8, 2025

When Being OK was not Good Enough

 

JJ Hart and wife Liz on right at Picnic.


I grew up in Ohio raised by greatest generation parents who lived through WWII and the great depression. Often, they were long on material support and short on emotional backing.

The main thing I remember from my childhood was, nothing was ever good enough. Take school for an example, while I excelled at subjects such as History and English, I really struggled with the Math and Sciences. Even still, I was expected to bring home straight A’s on my grade card every year. I had no excuses, especially when I went to high school where my mom was a teacher. She was pushing me hard for good grades to make it possible to get accepted by a good university.

I guess I became used to the pushing and figured nothing was ever good enough for myself and it carried over into my gender issues. Every time the mirror lied to me and said I was an attractive girl, I did not believe it and had to discover another way to prove it. Very quickly I learned I needed to replace the mirror with the public. Leaving my dark, lonely closet was the only way I could learn if I could ever achieve my dream of living a transfeminine life. It took every bit of courage I could muster to do it but if OK was not enough (by just standing in front of the mirror), I had to force myself into the world.

When I did force myself, it was like I was getting adjusted to a new pair of shoes. At first, I was tight and uncomfortable before I started to relax and began the basics of enjoying myself. I say I began the basics, because at every turn on my gender path, it seemed I was hitting a wall. Those were the times I needed to step back and decide if I was doing the right thing.

Those examples and failures proved to me I needed to keep going. Mainly because I felt so natural when I was pushing the envelope to leave my male self behind and live more and more as a transgender woman.

On occasion, proving OK was not enough and trashing the envelope almost got me into trouble. Mainly when I began to walk the fine line when I lost my male privileges. The most important being personal security. I was out and out lucky and escaped personal harm by men in the world. I wasn’t smart enough or experienced enough to sense the danger zones women are raised around. I learned quickly to park in well-lit areas or to ask for friends to walk me to my car. I did not want to be a statistic.

As I went through the process of living within the same parameter’s cisgender women have to face, I became a sponge of sorts. Nothing I did as I transitioned was ever good enough as my parents’ lessons oddly came back to help me. I was especially attentive when I went out to socialize with my women friends. They never realized what they did for me as I formed my own version of womanhood. In many ways I became a gender hybrid. It was impossible for me to leave decades of living an impacted male existence behind me, so I tried to take the good with me. For example, I was fortunate to have worked around women in the restaurant business for most of my life and I knew the trials and tribulations cisgender women faced in the world.

To this day, I have not shaken the idea of just being OK is just OK. I must be better just to be successful in the competitive world of women. I knew they could be competitive but not as much as I discovered when I finally had the chance to play in the girl’s sandbox. The whole process made me a better person in the long run, but it was surely difficult at times. Often brief moments of gender euphoria kept me going in my darkest gender hours. That was when I needed to provide electricity in my closet to give me the ability to see right from wrong.

Since my parents were my driving force behind my personality, I never had the chance to thank them for what they did. My Mom knew about my gender issues and chose to ignore them, and my dad never knew so I doubt if either would be pleased about their child raising outcome. They never knew how well OK was never enough worked out for me in my life.

 

 

Monday, July 7, 2025

Trans Girl on the "Down Low"

 

Image from Josh Withers
on UnSplash.


According to Wikipedia, down low is basically an African American term for gay cruising of other men. For this post, I am going to use it in another sense.

First of all, I need to take you all back to when I first considered my down low to be as I cheated on my wife. But I was doing it by cheating on her with another woman, which happened to be me. Of course, nothing made what I was doing right but I could not stop doing it as it had a powerful draw on me. Those were the exciting days of leaving the gay bar scene behind me and begin exploring the world of straight bars as well as lesbian venues.

Very soon, my success turned to failure as I began to feel guilty about lying to my wife about what I was doing. I tried my best to rationalize my thoughts because after all, I was having no physical contact with anyone. Male or female so I could not be accused of cheating, but I still was. The reason was, I had made an agreement with her that I could go out in public several days a week. Providing I never left the house cross-dressed. It was a sacred promise she never forgot and one I could not keep once I began to develop a transfeminine life.

Very soon, I felt as if I was still on the down low every time I snuck out of the house dressed as a woman. As I was basically doing as much as possible. The reason was, I was learning so much about the feminine world I had always dreamed about, I could never turn around and go back to my male life.

It was more exciting to stay on the down low until I could figure out what to do about the life I was leading. In fact, I because the more I experienced the new world, the more natural I began to feel as I was able to put the image I always saw in the mirror into motion. In many ways, I began to feel so natural as a transgender woman, it was difficult to ever return to being a man at all. I had to consciously tell myself I still was a part time man when I worked. So much so, I was beginning to be called ma’am when sir would have worked for the occasion. Still, I was secretly overjoyed when it happened.

Sadly, through it all, my marriage really suffered. Mostly because I was and am a very honest person and hated lying to my wife about what was really going on with me. Often, I learned when I lied one small time, I would have to lie more often to make up for it. An example was one year when we took a week for vacation and headed north to try to escape the heat. About two days into the vacation, I became increasingly mean and irritable because I really wanted to be spending my time traveling as a woman. Finally, my poor wife had had enough and asked me what was wrong. I lied again and internalized my feelings enough to get by, and we could eventually enjoy ourselves. Deep down, I hated myself for it.

Life began to finally slow down for me as I reached certain milestones in my transfeminine life. I was beginning to communicate with the world and started to feel much better about myself and at the same time my down low activities slowed down also. At least to a point where I could control them. It was around this time too, when my wife’s health began to really decline. It did not know it then, but she only had approximately six months to live. For some reason, I decided to go on a major purge and throw most of my feminine things away and went all the way to growing my version of a beard. It turned out, I did the best I could for the remainder of her life.

When she passed, of course I was tragically shocked and lonely, so I reached inward. The beard went away quickly, and I was able to restock my clothes and makeup. In no time at all, my inner feminine self was coming to my rescue. I began to retrace my steps I had taken as a novice transgender woman, and reestablished myself fairly quickly in the venues I was a regular in.

I was totally freed from the down low experiences from my past and could concentrate on going out to being alone. In other words, I wanted to be around other people. I just did not want them approaching me.

It worked in the short term until I began to socialize with and started to build a small circle of friends who knew nothing of my previous self. I never had had to go on the down low again.

 

 

Saturday, July 5, 2025

Affirmation Day

 

Image from Cate Bligh
on UnSplash

A much-needed affirmation day for me is here.

Today is the event I have written so much about. By pure chance, three of my daughter’s family have graduated from various institutions and will celebrate today.  

With a little luck (and planning on my daughter’s part) my transgender grandchild will return from their post-graduation trip walking the Appalachian trail. They graduated with a degree in nuclear engineering from The Ohio State University in the winter and immediately landed a job with the Navy as a civilian in Maine. They and theirs are their chosen pronouns.

Not to be outdone, my son in law is receiving his MBA this summer and my youngest grandson is graduating from high school. A group of overachievers to be sure!

This is where my affirmation comes in. The entire event is a safe space for me to go to where I can recharge my gender batteries for the future. Plus, my best ally, my wife Liz, will be by my side.

To be on the safe side, I have been planning ahead for months on what I am going to wear. I am aiming to be dressy and feminine without going overboard since I don’t know much about the venue.

I chose my favorite lacy feminine top and am pairing them with comfortable leggings and shoes since I don’t know how far I will have to walk. As always, I don’t want to stand out, I want to blend in. Sometimes, there are pictures taken, so if I get one, I will pass it along.

Past that, I have been able to do much of my pre-body preparation in advance, so today all I need to do is a close shave, makeup and hair to get ready. We have a reasonable drive to go north to Dayton, Ohio from Cincinnati to arrive at the venue.

As we go and I get my gender batteries recharged, I will let you know what happens.  

Thursday, July 3, 2025

Emerging as Your True Self

 

Image from JC Gellidon 
on UnSplash. 

Emerging as your true self after a lifelong gender struggle is often very difficult.

It starts very early in life when you discover you are in the wrong place at the right time, or the right place at the wrong time. Whatever the case, your struggle to find yourself begins. In my case I began with explorations into my mom’s clothing which lasted until I could no longer fit into any of her clothes. If you had suggested to me my final emergence into the world would take as long as it did, I would not have believed you. It was a long journey until I finally took the transition step to live as a full-time transfeminine person at the age of sixty.

Some of you may ask why I waited so long or since I did, why couldn’t I just wait for it a little longer into my senior years. On the other hand, I felt if I did not do it then, I would never have the chance. So, I pulled the plug on my old male life and emerged new as a transgender woman. It was never easy, but I made it.

Others may ask why I never opted for any gender surgeries of any sort. I did not because I was on the borderline to being able to present well enough as a woman to get by and I did not have the insurance or the finances to do it. Plus, I was superstitious about having any operations on my body since to this day the only surgery I have ever done was getting my tonsils taken out. I decided to set my gender dysphoria aside and work with what I had or pass out of sheer willpower as a transgender woman friend once told me.

I can’t tell you how many times my willpower was challenged before I made it to the point of emergence in the world. The seemingly endless times I was sent home in tears when my cross-dressing plans went wrong. Fortunately, I was stubborn and kept on moving towards my dream of possibly living fulltime as a woman. I replaced my willpower with confidence since in most cases, I was following my path in the most difficult way possible, without the help of any facial feminization surgeries. For the most part, makeup art was my way around having no expensive, painful operations until I could begin gender affirming hormones.

For me, the hormones worked miracles inside and out. Outwardly, my skin softened along with my facial angles of manhood, and I could use less makeup. Also, on the plus side, my hair grew quickly and fully since I inherited no male pattern baldness which made wearing any sort of a wig a thing of the past for me. What really changed was my overall view of the world. Suddenly, my view softened as my senses heightened. I felt emotions such as I had never felt before, and I learned how women complained they were always cold (except during menopause) because I was in my second puberty and cold all the time.

During this time, emergence became a slippery slide for me. The HRT hormones were quickly making it impossible to go back to my male life because I did not want to. Why would I want to trade in all the work I put in to travel my long gender path for anything? I finally gave up on all the resistance I was putting into retaining any of a life as a male I never really wanted. The only remaining reason turned out to be me losing all the white male privileges I had worked so hard to gain. For that reason, I put off emerging and attempted to briefly live a portion of my life in both binary genders. Something I would strongly suggest not doing. For me, trying it wrecked my mental health and nearly my life. My male side was hanging on and very materialistic while my female side was discovering a magical life is the best way I can describe it. Afterall, I could see my best-case dream life within reach.

Through it all, I think being approved by a doctor for gender affirming hormones was the biggest moment of my emergence as a fulltime transgender woman. With the help, I was able to carve out a new life and put the old one aside. I was able to see a new world with the help of new friends who never knew the old me. The essence of emergence when someone else could enjoy the company of my new feminine self. HRT was just a kick start to make it to where I wanted to be. I needed to take it from there and make my emergence complete.

 

 

 

Wednesday, July 2, 2025

The Second Act

 

JJ Hart doing Trans Wellness Outreach. 

Will the second act of life be better and more successful than the first? How many people even get a second chance?

That is the question I needed to answer when I finally shed my male life and entered a transfeminine existence. Since I did it at the age of sixty, I have had plenty of ground to catch up with. Many times, it seemed I never would. My internal gender clock was moving one step forward and two steps back as I attempted to transition. I had times when the picture was clear in my mind, and I was able to put it into motion. Such as the night I took myself out to see a major Christmas light display in a nearby village and was warmly accepted in my soft bulky sweater, leggings and boots. Then, as I rode the wave of gender dysphoria, I would do something wrong such as how I was moving. I am fond of saying, I looked like a linebacker in drag.

The problem was, if I relaxed at all going into the second act of my life, I had the tendency to fall back into old habits. I was learning the hard way over and over, to take nothing for granted in my new life. Many times, I tried and failed not to be too hard on myself since I was making up for a first act in my life which lasted so long, and I had to concentrate so much on it just to survive. It was around this time when my male self really began to set up roadblocks on my gender path. Suddenly, he began to see that this road I was on was not a phase or joke and I was deadly serious.  He started to ask questions such as how I was going to live in my second act with no job and how I was prepared to do it without the wife I dearly loved and had been married to for nearly twenty-five years. To be sure, all very real and very scary questions.

I put off deciding my life as long as I could as I attempted to learn if I could really live a transfeminine life at all. Were the obstacles insurmountable or not. Through it all, the one overriding feeling which kept me searching was the deep down feeling I was doing the right thing. I was headed in the direction I should have been going in my life all along and I kept going through the ups and downs of transitioning into my second act.

Once it was clear I was successfully transitioning into my second act, I needed to make sure I was doing it correctly. It turned out I had all the help I needed. In addition to the cisgender women I always mention, there was one important person I don’t mention enough. That person turned out to be very real and important to me. She was my inner feminine person who had been waiting for all those years and decades for her chance to fully come out into the world. Once she finally did, she knew completely what to do and what was ahead for my second act of my life. Mainly, all the nuances of life as a woman if I really wanted to go there. She knew the best part of my life was yet to come.

More importantly, I had finally made it through the bleak years when often I thought there would be no tomorrow. Or at least my dream of living a feminine life would never be realized. Often it set off a series of insecurities in myself which set back my life. Act one was bleeding because I could not get to act two.

When I finally made it to my second act, it was as if I had lifted a heavy weight off my shoulders, and I came to a point where I needed to be more understanding and approachable in the world. I could not get away with the old male ways of internalizing my feelings and start living again. If I did try to hide as a transgender woman, I would never have a chance to provide myself with a positive outlook to other women and not come off as an unfriendly transfeminine woman which was the last thing I wanted or was.

Since I was one of the few humans who ever had the chance to stop their life and begin again so there was no way I could mess it up. I needed to enjoy life and live it the best I could.  

Tuesday, July 1, 2025

Being Your Mother's Daughter

 

Image from Bence Halmosi
on UnSplash. 

What if your dream came true and you could have started your life as your mother’s daughter?

How would life really have been if it could have shared that special mother/daughter bond we can only see from afar.

As I changed my Estradiol patches this morning, I stopped to think how my mom and I would have gotten along if my gender world had been different. I know for sure; everything would not have been so rosy if I was living my dream. I remember vividly being able to sit back and watch mom expertly apply her makeup before she went out in public. Which her generation always did. I wonder now when she would have let me start experimenting with makeup if I was her daughter. I think now, I was wearing makeup before she would allow me to if I was in the feminine world I so dearly wanted to be in. I was also fairly sure I was shaving my legs sooner than she would have allowed.

The reason was, she probably never understood having a son who was really her daughter was all about. If I was her daughter, the pressure would have been on to conform to her ideas and rules. We were so much alike to begin with I am sure we would have fought continually. The gender grass always looked greener from the other side as I grew up. Especially when it came to the world of fashion. I had always admired the clothes girls around me were able to wear when I was stuck in the same old clothes.

It was not until much later in life when I started to really learn of the fashion problems my second and third wives had with their moms, did I begin to understand what they were going through. For example, my second wife told me several times about how she snuck out of the house with her skirt at one length (for parent approval) then when she was out of sight, she rolled it up to make it a forbidden mini skirt and supposedly mom never found out. On a more cruel side, my third wife Liz’s mom constantly harassed her about her weight. I can’t imagine how bad that made her feel. The closest I could come was if my parents ever berated me over a bad athletic play I made. Which they never did.

Overall, I wonder if any bond mom and I would have ever come up with would have been one existing of competition. I am sure my female self would have been struggling as much as my male self to gain any respect at home. All the way to the college I was going to attend. Mom was a graduate of an upscale public university in Ohio as well as being an active alum of one of their sororities. I am sure she would have pushed me (as her daughter) to follow in her footsteps, which would have been another problem.

I wonder if at any point in time, my dream of growing up as my mom’s daughter would have turned into a nightmare. Although, nightmare might be too strong of a term. Better yet, a struggle would have been better to use because both genders have their problems if they are over able to arrive at adulthood and claim the title of women and men. As I said, being a transfeminine person always seemed to be the best way to exist (for me) in life. I would never need to worry about being shipped to fight in Vietnam or summoning my courage to ask a girl out, among other things. On the other hand, I never had the opportunity to be asked out if I was a girl. Certainly, there was a positive give and take to both genders, but I was only seeing the good.

Would mom have taught me the basics of makeup? Or would I have learned it from girlfriends at weekly sleepovers. I am slightly biased, but I think I would have learned from my female peer group more than mom. Having never had the chance to learn, I will never know and since mom rejected any sort of discussion on my transfeminine life, there never will be any way to find out. She passed years ago.

It wasn’t until years later did, I have the chance to learn what I missed or didn’t when I grew up male. It finally took a group of women took me through the process of being a woman. In essence making up for what my mom missed doing. I inherited her stubbornness to do what was right and her ability to keep going until she arrived where she wanted to be. It would have been interesting if she had ever accepted the fact she had a daughter, not a son.

 

 

Sunday, June 29, 2025

It is Just a Phase?

Image from Claudia Love on UnSplash.

Have you ever been accused of just going through a phase?

Drawing from several comments from other transgender women and trans men, including myself, I have heard us being accused of just going through a phase when it comes to being transgender.

There was a time in my life when I seriously hoped I was just going through a phase when it came to my love of dressing in feminine clothing and makeup. I wanted it to be just an innocent hobby I could put down and walk away from at any time. As years went by, I found I couldn’t replace my so-called hobby with anything else in my life. I did the worse possible thing, I tried to internalize my feelings hoping I could somehow ignore them, and the phase would go away. Of course, it never did.

I always thought my mom knew I was trying on her clothes and putting on her makeup but never said anything because she thought I was going through a phase. Obviously, she was wrong! She never had the courage to call me out on what I was doing until I brought it up to her in a very ill-fated attempt to come out when I was discharged from the Army many years later. She quickly rejected my attempt to clear the air by volunteering psychiatric care. Of course, I refused her offer because I knew I was not mentally ill. I just wanted to live a transfeminine life on my terms. We never mentioned it again for the rest of her life but at least I tried to explain my deepest secret to her.

The phase idea came to be one idea I always ran from. I did not feel deep down my feelings were a phase but still was afraid to face the truth. I ended up moving many times and trying many new jobs just to try to outrun my gender feelings. It all was exhausting to my already fragile mental health. In fact, my initial gender therapist diagnosed me as being bi-polar when all along I thought I was just terribly depressed when I never thought I could achieve my dream of living as a full-time transgender woman. I was depressed when I considered the extreme distance I still had to travel, just not as bad.

As I still managed to progress along my gender pathway, I still encountered phases I needed to go through. The major one was what I called my teen girl dressing years. As I survived my urge to stuff my oversize male body into skimpy fashions, I was quickly laughed back into my closet several times before I learned the proper way to attempt to blend in with what other women my age were wearing. Easily, it was the most difficult phase I needed to deal with. Mainly because I was so stubborn.

It turned out the stubbornness I possessed was just what I needed to keep going. Deep down I knew I was in the middle of one of the most complex journeys a human can take, and I could be successful if I tried hard enough. It all meant I needed to earn my way through the feminine gatekeepers I faced to be allowed to play in their sandbox.  I was petrified when I needed to actually begin to talk one on one with other women. Very early on, I was frightened of their reaction when they learned I was not a cis-gendered woman. This was before I learned my path to womanhood was as valid as theirs. I just came to mine along a different path. Amazingly to me, the doors were opened to me, and I was permitted to play behind the gender curtain.

It was around this time when I began one of the most powerful phases of my life, when I made the correct decision to begin gender affirming hormones, or HRT. I say powerful because the new hormones I was prescribed by a doctor turned out to be everything I dreamed of and more. If anything, else, the hormones proved my whole life was not a phase. Now I felt as if I was arriving home in the deepest sense. If you compared my hormonal life as a circle, I was completing mine. The effects of HRT made me feel whole as a transfeminine woman. I could feel deeper, be more emotional and enjoy the world as never before.

I proved, more than ever before, my life was not a phase, I was much more than just a man putting on a dress. I proved all along I was a woman putting on a male face and clothes all along. At the least, I could rest easily knowing what my gender issue was all along. Not a phase but my life.

 

 


Friday, June 27, 2025

What Did I Miss?

 

JJ Hart at her first Girl's Night Out

Often, I am sad when I see a group of young girls playing. All too often, I wonder what I missed when I was growing up.

I then remember all the times in school when I was forced to play with the other boys and not join the girls’ group to learn what they were up to. Essentially what I missed was the chance to fill out my own gender workbook.

Since I believe women are socialized and not birthed, the early interactions of the girls robbed me of getting a head start towards my own unique womanhood. So, my gender workbook remained mostly blank for years, until I could claim the experiences, I needed to begin to fill it out.

Ironically, as I write about often, the greatest majority of my first interactions with the public came with other women. Then, I did have a chance to start to catch my gender workbook up as the other women indirectly (and directly) shared the pluses and setbacks of their times growing up and passing the gatekeepers into being treated as a woman, not just a female. At the time, I was so afraid of testing out the gatekeepers to see if I could be admitted that I never tried. Instead, I hid my desires, until I was sure I could make it. Still, it was very difficult to make it because of my continued shyness around strangers which was compounded by my transfeminine life. There just were not many like me in the world to pave the way.

As I began to pave the way, I needed to smooth out my journey. First, I had to figure out a way to properly dress my testosterone poisoned body so I could present well as a woman. To do so, I needed to become a regular at all the area thrift stores, as I shopped till I dropped for just the right fashion piece to add to my growing wardrobe. Once I did that, I could continue building my own path to maybe discover what I had missed not growing up as a young girl.

Surprisingly, as I began to be invited to special girls’ nights out, I began to learn I was not missing out as much as I thought. I discovered what I always had thought was true. Takeaway the talk of sports and business which men talk about and add in softer subjects such as family and friends, and I could indeed survive the new world I was in and not sit around like I was a hermit. I needed to hit a middle point of being interested in the conversation and adding in just the right amount of conversation. Such as, I found I could still talk about my daughter and grandchildren and still be relevant to the rest of the group.

What I was doing was skipping ahead in my workbook to sections which would include usage of the women’s restroom. I learned the importance of looking another woman in the eye when I met her because I could on the new side of the gender border I was on. My workbook said I could and should to survive and even thrive. I knew I had made it to some sort of a gender promised land when I was asked by other women to make the “sacred” journey to the rest room.

Even with all this happening, I was still frustrated by all the sections of my workbook which were blank. Deep down, I knew I could never reclaim the early years I had being forced into the male square hole I was in when I knew all along, I should have been in the round female hole. Perhaps the most frustrating part of the whole process was, the more I was forced into the male side, the more I was rewarded into acceptance. I refused to throw away my transfeminine workbook anyway and just hid it during times when I was forced into the Army during the Vietnam War.

For some reason, my workbook always resonated with me as I went through the down times. It was my shining light when I needed it to be. I just overcame the beginning chapters which were missing. My path to womanhood would just have to be different and in many cases more difficult than the average cisgender woman. I had to be better just to survive in a new world I was just learning about since I was not allowed to learn about it early in life. As I watched the other girls around me, often my jealousy grew because I never had the chance to wear pretty clothes or gossip with the other girls.

I learned my gender workbook was fragile too and could be changed or corrected at any time when I had misread certain situations. Which I write about often. I just stored the information away for use later. I am still adding to my workbook to this day.

 

 

Wednesday, June 25, 2025

Catching Up

 

JJ Hart, Hot Summer Day.

This morning was a day to catch up and run errands.

Because of the continuing heatwave we are under here in Southwestern Ohio, I needed to get an early start. For example, it is nearly ninety degrees (F) before eleven AM with heavy humidity. So, by early I meant the pharmacy I was going to did not open till nine o clock. Plenty of time for me to have a leisurely morning as I got ready. By getting ready, I did not mean I had to go to any elaborate means to do it. Basically, all I needed to do was shave closely, apply moisturizer, makeup and brush my hair. I figured the least which would happen to me was I would see two different people in drive thru’s.

Of course, I was wrong because my second stop involved an up close and personal interaction with a coffee shop employee who was taking orders outside the window since the equipment had broken down in the heat. It turned out all my built-in paranoia of meeting strangers was unfounded for at least today.

First, the guy at the pharmacy had the personality of a cardboard box and could have cared less about me. And, as far as the girl I interacted with personally with the second drive thru went, she was very nice to me, and I felt as if I was welcome.  Especially since she knew I (assumed) I was transgender. Whatever the case, I felt good as I headed home before the traffic became worse again.

Speaking of going out, my wife Liz and I’s trip up to Dayton, Ohio during the upcoming Fourth of July weekend is rapidly approaching. My daughter is having a graduation celebration for her family. My oldest grandchild graduated from Ohio State last winter and is coming home from hiking the Appalachian trail before she takes a job in Maine this fall. In addition, my youngest grandchild is graduating from high school, and her husband is receiving his MBA. The event is being held outside, so I need to plan accordingly. I have picked a very feminine top to go with leggings and flats so I can be appropriately feminine without going overboard.

It does not seem possible, but the next big event is Liz and I’s big trip to New England in the fall. Just like that, another summer will have gone by. At my age, there is no way I should be wishing time away. As my mom was fond of saying, age is like a roll of toilet paper, the closer to the end you come, the faster it goes. As with most things mom told me, she was right.

It seems, no matter how small the public interactions are, when I am positively impacted, the better my life is. It is like charging up my gender battery. I constantly need it. Such as the positive interaction I had today.

Tuesday, June 24, 2025

Painting a Picture

 

Image from Vinicus Amix
Amano on UnSplash.

During my life, I have never been accused of being an artist. In fact, I would mess up drawing stick figures.

The best thing I could do was connect dots. Which I needed to do quite often in my gender conflicted life. Basically, the main dots I needed to connect were, was I a boy or a girl. It ended up taking me far too long to finally connect those dots and attempt to draw my gender picture.

When I began to experiment with makeup, I learned the basics of facial artwork and even I could make myself look better in the mirror. Mainly, though, I struggled along until I summoned the courage to request a makeover from a professional makeup person at one of the transgender-cross dresser mixers I went to. He did a miracle job and transformed me into a woman who I only had dreamed of. Most importantly, he was able to explain to me what he was doing in a step-by-step format that even I could understand. I looked so good, I was invited along by the “A” listers, as I called them when they went out to explore other venues after the mixer was over. I even got the last laugh over all of them when a man tried to pick me up in a venue we were in, and they were not.

Sadly, the success I felt from the mixer did not last long when I had to go back to the real world, I was a part of. When I did, I became mean and nasty to my wife and others around me. All the way to almost losing jobs because of my attitude. No way to paint a picture. Somehow, I needed to get better before I self-destructed my life.

I hung on until I did get better when I had the chance to leave my closet more than once a year for Halloween parties. I was aided by the fact that my artwork with makeup and clothes continued to improve until I looked better than some sort of a circus clown in drag. I simply had to if I was ever going to have the chance to live my dream. Through it all, it did occur to me how difficult the process was going to be. I was painting two pictures at the same time, one as a transfeminine woman. One as a successful man. The stress of doing so nearly killed me. Being a man was easier because of all the white male privileges I had gained but being a transfeminine woman felt so exciting and natural when I painted her.

By the time I had gotten this far, I found I had painted myself in a corner. I could see the finish line for a change, while at the same time, I had a wife I loved, a family I loved and a good job to protect as a man. Decisions, decisions were wearing me down. Primarily because it was so frustrating to me to have worked so hard throughout my life to paint two pictures, only to have to finally choose between the two. What I did was let the public choose which picture they preferred. Since my transgender woman had an unfair advantage, she won the contest easily. She got to start all over again and learn from all the mistakes her male counterpart made and go from there. Time and time again, the public picked her.

Putting the finishing touches on my feminine portrait proved to be easier said than done. First, I needed to come out of my closet to what was left of my blood family. I received a 50/50 reception when I was accepted by my daughter and rejected by my brother. By this time both of my parents were deceased. Predictably, both coming out events were scary and quickly resolved. My daughter wondered why she was the last to know while my brother did not have the courage to stand up for me to the rest of his extended family. We have not spoken now in over a decade. Sad but true, he never wanted to see my finished portrait. Conversely, my daughter and I are closer than ever.

But then again, are our portraits ever finished until we die. Shouldn’t we always be making small upgrades the best we can? Plus, age should put us in a better position to do it. Sure, painting two completely different gender portraits at the same time was difficult and at times required tons of skill to keep one hidden. But somehow, I was able to gain the artistic skill to make it happen.

The powerful draw of an overwhelming dream was all the motivation I needed to become a better artist and provide the background I needed to live a life as a transgender woman.

Monday, June 23, 2025

The Biggest Lie

 

Image from Dave Goudreau 
on UnSplash.

Sadly, the biggest lie I’ve ever told in my life regarded my biggest truth.

The lie of course, regarded my gender identity. For simplistic reasons I could say the problem I faced early in life was having a complete lack of information to lean on. It was back before the internet information years, and I thought I was the only boy in the world who wanted to be a girl part of the time.

To compensate for my cross-dressing activities, I was prepared to lie my way through it. If I was ever caught red handed because of leaving lipstick on my fingers. Due to whatever circumstances which were beyond my control and very lucky, I was never caught by my family. Although I always have wondered if my mom somehow knew but hoped my fascination with her clothes was just a phase I would grow out of. The best part was, I never was caught or questioned so I did not have to lie my way out of an ill-advised trip to a psychiatrist. Back in those days, being a transvestite (the term which was used) was a mental illness problem. Not something I wanted to face. So, I hid in fear.

As I weighed the two alternatives, fear or lying, I chose to internalize the fear I was feeling every time I put on feminine clothes. Once again, I was able to put off lying to the one biggest person in my life…myself.

All was well until I was discharged from the Army and returned to civilian life. Once I did, I began to pick up where I had left off with my gender issues. I even went as far as almost telling my first wife who was also in the Army and was being discharged several months after I was, to expect a totally different me when we met again. I was totally thinking of meeting her as my transfeminine self. As much as I secretly wanted to, deep down I knew I was not ready for such a big move, so I hid my feelings again and lied my life away, for a while.

You know what they say about lies, the more you lie, the more you have to. Just to stay above water. Before long, I was drowning in my own personal lie, until I met my second wife. She was much stronger than my first wife who never said anything negative to me at all considering my gender issues. I often thought wife number one would not protest at all if I told her I was leaving for a period of time for sex realignment surgery. She was just too easy, and I divorced her to be with my second wife who also knew of my cross dressing. Which started out good but deteriorated

I say deteriorated because my second wife did all she could to support my growing gender issues until I had outgrown both of us. All of the times she encouraged me to go ahead and rent a motel room and spend the day out as a woman taught me valuable lessons. First and foremost, I could make it in the world as my feminine self after all. Then, the big lies started as I began to go out on my own when my wife was at work, from the house. Which was something I told her I would never do. By doing so, I began to live the biggest lie of all, as I was increasingly aggressive in my attempts to do more and more in the world away from my masculine self.

Naturally, the tailspin I put our marriage into put a strain on both of us. Especially when she caught me going out. When she did, a massive fight would break out for days until somehow an uneasy truce would be called. At times, things would be so bad, my wife told me just be man enough to be a woman. The problem was, I was still lying to myself thinking I could keep my married life balanced with my transfeminine one. I just was not that good a juggler to do it. Again, mainly because I could not face my truth.

Sadly, my second wife passed away before I faced my truth. Being the wise one in the relationship, she knew me better than I knew myself. Pushing me to pay attention to what it really meant to be a woman.

Now I just wish I did listen to her and went ahead and transitioned. Sure, it would have been difficult but living the life we lived was difficult too and I could have started living with a clear conscience. Being the stubborn person that I was, I kept on living a lie until I could take it no longer and finally made the move into a life I could enjoy as a fulltime transgender woman.

By the time I transitioned most of the important friends I had known (including my wife) had passed away. Leaving me alone in the world to carve out a new life in my sixties. It would have been very difficult, but I wish I had listened to my wife and been man enough to be a woman sooner.

 

 

Sunday, June 22, 2025

Building Bricks as a Trans Girl

 

Image from Marcus Spiske
on UnSplash. 

If nothing else, my long life has been a series of gender building blocks.

Ironically in my youth I spent hours building small houses with a set of plastic building blocks I was gifted. That was until I discovered the joys of mom’s clothes and began to admire myself in the family’s hallway mirror. Little did I know, from those humble beginnings, I was heading towards building a lifetime of building blocks. Transphobes as well as other assorted bigots were ruining my early days as a transfeminine woman. Which meant I needed to sort through my gender bricks until I could survive.

Very early on, I knew I needed to build a strong closet. To quote a famous “Doors” song, I was a “Rider on the Storm.”  Somedays my storm would be less as my gender dysphoria subsided on others it was unbearable and all I did was think about the next time I could cross dress in front of the mirror. It was on those occasions; the mirror would play tricks on me and tell me I was an attractive woman. I say tricks because on a good day, I had not mastered the art of makeup or fashion. I needed to be persistent in my building blocks because I would never have been successful if I did not. My dream of living a life in a transfeminine world was proving to be much more difficult than I ever imagined.

It turned out my wife was right, I did make a terrible woman until I paid my dues, but I couldn't pay my dues until I built enough gender bricks to be allowed behind the gender curtain to learn the nuances of doing it. One thing I did know was that I was my gender journey of a thousand miles did begin with that single step in front of the mirror. To keep up with my journey, more and more bricks would be needed for me to succeed. Once I was behind that imaginary but so real curtain, I became a complete sponge to be the best transfeminine person I could be. Some days I was thrilled to be where I was and on others, I was scared to death. Building a new life from scratch with very little help proved to be intimidating.

I learned and became better at dodging the barbs and smirks of the haters in the world. I had built enough bricks to replace my old gender closet with a new one which was built to last me. The new closet was good enough to take me to the point where I could authentically begin a new life as a transgender woman. Which meant I needed to be better than the average cisgender woman just to get by.

The women around me who helped me build my new gender fortress were the gate keepers who never knew how much they helped me live my dream. I was able to layer my feminine experience all the way to success.

Little did I know when I was a kid trying on my mom’s clothes for the first time, how far I would need to go to survive. My last adventure turned out to be my best.

 

Friday, June 20, 2025

A Trans Girl in the Arena

 

JJ Hart at a Witches Ball. 

Or, should I say, a scared trans girl in a new arena.

As I started my gender transition from male to female, I truthfully did not have an idea of the complexity of what I was getting myself into. I had closely studied the ciswomen around me for years to try to see what made them tick and how they survived the challenges in their lives. I also learned the hard way; I could only go so far until I was allowed behind the gender curtain.

My first initial shock when I entered the arena of life as a transfeminine person was everyone would be looking at me. Sure, I was used to the fact that all men looked at women and judged them, but I was not prepared for women doing the same thing and even more so. Since I was never the most attractive woman in the room, I did not have to worry about most men giving me a second look. Except those men who desired me for what I was, a transgender woman.

Women were a completely different deal. I found quickly how another woman could look you up and down, and head to toe. Judging me without saying a word. It took me awhile to get over the experience and plan for it. If I was going casual or professional, it did not matter, I needed to be perfect in my presentation. From accessories to shoes, I needed to shine, or blend. In other words, I needed to be better than the average ciswoman to survive in the new arena of life I chose. An arena where everyone noticed who I was or wasn’t.

After the initial shock wore off, I learned that this part of my new transfeminine life was just something I needed to get used to. For the most part, I was used to men shunning me and women showing interest in me because they were curious what I was doing in their world. I ignored the men and concentrated on the attention I was getting from the women because I was learning so much from them about how to survive in the new gender world I was in. Sure, I suffered several bumps and bruises along the way, but I survived and moved forward. Sometimes quickly, sometimes slowly until I found my way.

Being a trans girl in a big arena surely brought on a new set of challenges when I lost all of my male privileges. Such as my right to personal security and my right to express myself to the best of my ability. I was used to being able to scare off most all of potential physical danger as a man, which of course was all lost as a woman and I was nearly attacked several times before I learned. Also, being excluded in conversations simply because of who I was became a common place. Both aspects of my life were something I did not quite bargain for when I entered the new arena I was in.

The nuances of living in a new arena became a common place for me. As I transitioned from cross dresser to full time transgender woman, I knew I was in the right place, and I could see the so-called finish line ahead. Or so I thought.

Now at the age of seventy-five, I can see the finish line but for the most part it has nothing to do with my gender arena. The finish line I am seeing has to do with my own mortality and how my family will remember me. In many ways, I am the unintended role model for my transgender grandchild who is facing an uncertain world. I say unintended because I had nothing to do with my grandchild’s life choices. They (choice of pronouns) are just fortunate in that their parents are so supportive of the life choices they make coming from such a diverse family environment.

I believe we will never stop transitioning in our lives. We keep transitioning all the way to the grave as transgender women and trans men whose families refuse to bury the trans people as their authentic selves. The final battle and insult. The arena never seems to be quiet at all.

At the least I could say, the journey to the gender arena and the successes and failures on how I survived were never boring and not something the average human will ever know. Perhaps, it is part of the reason we have been demonized by a certain political party when most of the population has never met a transgender person. If they ever stepped into our arena and saw our life firsthand. They would know, we are not such monsters after all, just average people trying to make it in the arenas we chose.

 

 

 

 

 

 

 

Thursday, June 19, 2025

A Trans Girl and her Hair

 

JJ Hart and Mega Hair. Most of
it is tied up behind my head.

Certainly, one aspect of life transgender women share with cisgender women is the love of their hair.

Very early in my life and for years following, like so many novice cross dressers, I had no access (financial or otherwise) to buying a wig, nor did my mom wear one. I was stuck wearing a towel around my head and imagining I had beautiful flowing hair.

I needed to wait until my college years before I could afford to buy a wig, which supposedly was for my fiancé who I desperately wanted to not like it. To me, it was long blond, thick and beautiful, and I couldn't wait to try it on. I was still firmly in the closet to her in those days, so I needed to figure out an excuse to wear it.

Finally, I could not take the pressure any longer and came out of my closet to her and asked her to dress me head to toe as a woman with (you guessed it), that beautiful hair to finish off my outfit. As it turned out, that one day of satisfaction of cross dressing would come back to haunt me later. To make a long story short, she held my gender issues against me and threatened to leave me if I did not tell the military draft board, I was gay when they came after me during the Vietnam War. We broke up when I refused her demands and fortunately, I got to keep the wig. Years later, I found I received the better end of the deal.

After I was discharged from the military, I did have the financial resources to purchase more wigs and was able to be successful on occasion when I did not simply try to buy the longest hair in the wig shop, I went to. I normally traveled at least fifty miles to get to a quality venue to purchase a new wig. I was obsessed with my hair; it was the crowning glory of all the work I put into my fashion and makeup. As with many other aspects of learning to blend in with the other women around me, I took the wig obsession too far. I was beginning to be involved with the public far too often to change wigs every day. They were beginning to know me looking a certain way and I needed to stay on course to carve out a niche as the new transfeminine person I wanted to be. My clown wigs, as I called them, went into a storage bin, only to be seen again on Halloween…maybe.

The biggest jump from there came when I started to grow an amazing amount of my own hair when I started gender reaffirming therapy or HRT. The prescribing doctor told me that I would grow a lot of hair, and he was right. He noticed at the age of sixty, I had no signs of male pattern baldness which I carry over to this day.

Another person who noticed my hair was my daughter and for my first birthday following coming out to her, she offered me a trip to her upscale beauty salon for a color and style of my new hair which was all mine! Naturally, I was scared to death to go but the experience opened so many doors for me. The main door was the understanding of why so many women make a priority of going to a hairdresser to look good. As I soaked up the atmosphere at the salon, I thought I could skip my daily dosage of estradiol tablets I was on at the time were not needed because of all the estrogen in the air. Even though I was still frightened, I still loved it as I was the center of attention for my hairdresser and my daughter who was hovering nearby.

From that point onward, wigs were in my past and I needed to concentrate on my own hair. An immediate problem was I couldn't see the back of my head and did not have a wig head to rely on to turn the hair around and see the back. It did not take me long to master the art of holding another mirror up, catching the reflection in the main mirror so I could see the back of my head. Initially, I compared it with seeing the dark side of the moon.

I know my experience with hair turned out to be very lucky in my world of genetics. While I did not have to put up with expensive wigs, going to a hairdresser is certainly not cheap. Plus, for me at least, I think the ability to go without wigs was one of the most important aspects of me presenting well as a woman.

Maybe it was karma making up for all those years I had to have short hair, when I was finally allowed to grow it out. Whatever the case, I share with women everywhere, trans or not, the importance of having good hair. Plus, you can still have great hair with your wigs, if anyone asks if it is your own hair, you can truthfully answer, yes! I bought it.

 

Saturday, June 14, 2025

A New Day

 

JJ Hart, Dining Out. 

This post is a little shorter than the recent ones I have posted but no less important and it involves last night's trip to a restaurant venue we always go to.

It seems, every day is always a new day for me. Last night, my wife Liz met her son for dinner at our favorite restaurant where we dine approximately every other week.

As luck would have it, since the venue is large, we have had the same server several times before. About three visits ago, I wore my new Margaritaville T-shirt I bought during our winter trip to the Florida Keys. Even though I thought it was appropriate to drink a Margarita when our regular server promptly called me the dreaded “sir” word. Sadly, my Jimmy Buffett Margaritaville shirt was not feminine enough for me to pass the gender test. So, I needed to relegate it to just wearing around the house. I was sad.

Last night was different. I wore one of my most feminine lace trimmed tops and our regular server seemed a little gender confused but did not call me “sir” and I was satisfied. Also, one of my favorite things about the venue is I never had any problems with being mis-gendered by anyone. I could just relax and be myself. It was one of the first venues where I could sit and ponder the old days when I struggled to exist as a transgender woman at all. I was revitalized every time I went. Which made it a new day.

In many ways the process taught me how far I have come in living my gender dream, but in so many ways can not give up or relax the process. Even though I don’t wear a lot of makeup, I need to make sure I wear the basics every time I face the public. No pun intended. The moment I let my guard down; I could be reverted to the “sir” word I worked so hard to put behind me.

In many ways, when I transitioned from a cross dresser to full time transgender woman, I knew every day would have to be the new normal for me. There would be no more planning ahead three days or so for the special days when I could face the public as a transfeminine woman. I would be doing it every day. I went into a major wardrobe expansion mode. Just to keep up being in a new gender world. As soon as I dropped my guard at all, I would risk slipping back into the world I waited so long and worked so hard to get out of. Fortunately, I was very paranoid about doing it and I was able to translate my fear into positive feelings about what I was trying to do.

There were many steps backwards on my journey to discover how uplifting and pleasurable my life could be at the age of sixty when I seriously began my transition. The longer I was able to live this new life, every day turned out to be exciting and I was less vulnerable to outside threats to going back to my ingrained old male life. Eventually, life took care of itself as I found new friends and part of my family accepted me. I was able to live long enough and escape the self-destructive behavior I exhibited. Life was just a huge circle, and I was on the slippery side of the circle. I could risk everything to selfishly live my life and make everyday a new one. Or stay the same and wither away.

Naturally, making every day a new day was a challenge. Waking up every day addressing a new life was all I asked for and all I ultimately received. It was who I really was and proved to be a wonderful overall experience of gender transition.


A Tale of Contrasts

  Image from UnSplash. No matter how you cut it, our gender is a tale of contrasts. From the earliest age, we are forced into rigid gender...