J.J. 's Condo

Using yet Another Term

2026-06-09T10:38:43.308-04:00

Trans Tennis Star
Renee Richards circa 1976.

Recently, I used the term “dead name” to describe my old male name which I legally changed years ago. Rather than using “dead name”, Kayla wrote in and responded by saying she uses “former tenant” when referring to her former self.

I liked the idea and decided to pass it along to all of you for your consideration. I mean it is not like we have enough other terms which have evolved and even disappeared over the years. If you are of a certain age, you probably remember when transvestite was used as a term to describe many of us with gender issues. Then there is the term “transgender” which (according to Wikipedia) was originally used in 1965 by psychiatrist John Olivien then popularized by Virginia Prince in the mid 1990’s. Which was when I began to hear about being transgender and how it applied to me.

It was not until I began to go to the old “Tri-Ess” social transgender-cross dresser mixers, did I really begin to grasp the differences in the terminology to describe myself which was becoming more and more important to me. During the earliest times I can remember coming out to anyone was in the mid to late 1970’s when I used the transvestite term rather than using cross-dresser which perhaps would have been easier for the other person to understand. At the time, I was selfish and was not so concerned about what the others thought about me as I was about preserving my male self and was not coming out to many others anyhow. I stayed with thinking I was a transvestite which was not as far along on the gender disruption order as transsexual which meant to me as wanting major surgeries to live fulltime as a woman. At my age, “Christine Jorgensen” was the first person I remember as a well-known transsexual when she published her autobiography in 1967. The year I graduated from high school, so I had a real interest in secretly trying to find a copy of her book and try to read it which I never did. The closest I ever came was finding a copy of the “Renee Richards” book “Second Serve” which was published in 1976. I found it interesting when I researched Richard’s book in Wikipedia, no reference was made to her being a transsexual woman, only a transgender one.

About that time was when I began to seriously feel as if I fit the definition of a transgender woman more than any definition, I had ever seen before. I was somewhere off in a never-never land between being the cross-dresser I always perceived myself to be and the transsexual self which was rapidly disappearing as a term.

For me, at least as I “matured” into a “transfeminine” person which supposedly first appeared in a “Tapestry” publication from Tri-Ess in 1985. About the time I was seriously looking for ways to escape my gender closet. Also the time for me when I began to have serious access to the internet and social media which over the years was to open many new doors for me as well as many new terms such as the use of LGBT at all as many more letters were added to support different gender communities. In my latest search, I found the term is up to LGBTQIA+ to include all the variations on the gender spectrum.

Then there is gender fluidity which I have known a few people who have described themselves as such over the years. In fact, we had a gender fluid person attend our support group meeting here in Cincinnati years ago who went only with their middle initial as a name and refused any of the traditional he or she pronouns. I often thought maybe I was actually gender fluid growing up on the days I wanted to be a girl instead of the boy gender I was born into.

In another support group years ago, I mentioned another group catch phrase centering around Hormone Replacement Therapy or HRT. I called it HRT and Andi gently reminded me that a better, in-depth term, would be gender affirming hormones which made sense to me and I try to use both to this day.

Now I get to throw another gender term into my years old trashcan thanks to Kayla. I will never have to use a term I always hated anyhow to describe my ascent to being a successful trans woman in a world of ciswomen. Which, for the sake of staying with the theme of this post simply means a woman who was born female and still identifies as a woman.

I suppose the meaning of all these labels simply shows what a complex community the LGBTQIA+ really is and the most important thing is that you find the little niche you need to survive in. If you can follow all these changes, you deserve all the progress you have made. When push comes to shove all these terms are just semantics and you deserve more as you enter your authentic life.

I know there are other labels I have missed. I hope I have covered the major ones that helps us all and my “dead “name is now truly dead.

Destination Unknown

2026-06-08T10:07:48.194-04:00

JJ Hart and wife Liz on Right.

Through most of my life, I have taken the path less traveled to an unknown destination. Many times, I have thought I knew where I was headed, only to be faced with many stop signs in my way. It was like the night I took the night bus to Ft. Knox, Kentucky to begin my Army basic training. All I really knew was I did not want to be there and I would be in for more unpleasant situations than I wanted to count. All without my precious feminine wardrobe, heels and makeup to fall back on.

To make matters worse, some of the other men on the bus were not so silently crying about their fates which were coming up, quickly because before we knew it, the bus arrived at the not so beautiful, winter-time hills of Ft. Knox and we were greeted by drill sergeants and loaded from the bus into our waiting barracks. In a small way, I guess I was fortunate that I had two friends who were drafted ahead of me into the Army who told me what to expect and gave me some sort of confidence that I could successfully survive whatever was ahead.

Actually, for me, basic training went fast seeing as how I was facing an extended period of my life without the feminine fallbacks I had always known to get me by. Keep in mind too that the Army in those days was deeply gender separated and there were no women to interact with anywhere where I was at all in basic training. So, I was forced to do all my interaction with other men which I had never been good at. It turned out to be a learning experience I will never forget and even gave me extra insight about how competitive men interact with each other when there are no ciswomen to show off for.

Through it all, my inner super repressed feminine self was busily recording all of this for use later on in my life. Any spare moment I had when I was doing some sort of a mundane task in the chow hall for dinner like peel potatoes, I was given the chance to day dream off to the future and think of the new car I was going to buy with the money I was saving because of Uncle Sam taking care of everything I needed. I dreamed of buying a new wig and clothes and making it a point to slowly drive past my first fiancé who had rejected me when I was drafted into the military. She thought I should have tried to get out of serving because I was a cross-dresser. Which was close enough to being gay for her to get me rejected from duty.

When my three years of military service was up and I returned to the world I knew before, I returned almost exactly where I was with my cross-dressing when I left. The only difference was when Halloween rolled around and the newly restored Ohio Theatre in Columbus was having a costumed “Spook Out” with their newly restored theatre organ providing the background sound live for the silent version of the “Phantom of the Opera.” It was an opportunity for me to jump out of my dark gender closet and present my true self to the world for the first time since I was a civilian again. For the evening, I was the long blond-haired woman in heels and a minidress which of course included my freshly shaven legs and new panty hose. Outside of the heels beginning to bother me as the evening wore on, I had a wonderful time. Especially when I had the chance to see and appreciate the other costumes.

From there, the only problem I had was thinking about waiting another long year to be able to come out of my closet and express myself as a transfeminine person. I had just spent three years of my life waiting for my freedom from the Army and I did not want to wait anymore. My solution was to open my closet door and have the courage to come out on my own and not wait for another year. I knew in order to do it; I needed to take my feminine presentation standards way beyond what I was doing for Halloween if I was ever to make it in a world of ciswomen. Certainly, I made mistakes along the way as I stumbled out of the closet but managed to maintain the balance on my heels to get by in the world.

Thanks to previous life lessons I had learned to rely on myself, my inner female finally had her chance to come out and shine in the world when I started out evenings to go out and be by myself and ended up talking to other curious ciswomen wondering what I was doing in their world. I had learned to outgrow my shyness around strangers and become a social person, so my “plan” worked to perfection. I did not have to go out anymore to be by myself and my previous unknown gender destination was becoming clearer to me.

For the first time, I was able to see ahead of myself for future reference the stop signs I would face. Such as what was I going to do about all the male baggage I had managed to build up over the years against my will. If you are trans, you know what I am talking about such as spouses, family, friends and employment to begin with. Along the way, I have written entire posts about the power of stop signs and what they mean to transgender women and transgender men. I can only say, when you have negotiated all your stop signs and reached your unknown destination, you will have reached your own little utopian space because it feels so natural to you. At least it worked that way for me.

Thanks for reading along!

Any comments are always welcomed!

Hey You!!!! Meeting Myself in the Middle

2026-06-07T10:17:30.571-04:00

Image from Adam Winger
on UnSplash.

For me, meeting myself in the mirror was never easy to do. While the group of boys I grew up around were blissfully doing boy things without a problem, I was struggling with the idea that I wanted to be a girl.

Sadly, for the longest time, I thought that someday I would have the chance to outgrow what would become for all to call gender dysphoria. For me, I was just a kid with problems I had no idea of how to conquer. Through all this time of my life my favorite quote to pass along was when some adult asked me what I wanted to become when I grew up, I could never tell the truth and say a woman as I lied and said a doctor or a lawyer. The only thing with certain that I knew was I would get an immediate trip to the psychiatrist if I had ever told the truth compliments of my parents.

As I always say, age entitled me to a chance not to outgrow being a cross-dresser but did give me the opportunity to meet myself in the middle and start to mature into the transgender woman I am today. Before I did though, I needed to come up with an understanding of what the middle of being me really meant. What made it all so difficult was that my male life when it was going well it was very good, but when it was bad, I wanted out immediately. As I ran to my makeup, dresses and heels for comfort in the mirror.

The middle began to be harder and harder for me to find when I left the home mirror, gathered my courage and headed into the world as a transfeminine person. Many times, I could almost see and sense my middle person in the public mirrors I was still using to build myself up in places such as clothing stores in the malls and changing rooms I had started to use in all the thrift stores I was shopping to discover the latest fashion item I could wear. I was never any good shopping for women’s clothes as a man, as my feminine self-wanted to do it all and make all the final choices for herself.

In addition to fighting for the middle with my male self, I needed to fight my second wife for the rights to her husband. Like my male-self, my wife was a formidable opponent to any idea of me transitioning any further into the feminine world I increasingly wanted to live in. In many ways, she held all the gender cards because she knew I was a cross dresser when we met but never/ever agreed to me going past that point as she said she did not sign up to live with another woman. For whatever reason she never liked the transgender woman I was becoming and passed away before she could meet the finished product I had become. I don’t blame her because she just got caught in the middle of me not wanting to admit to what I always knew deep down…there was actually no middle point to me, I was destined to eventually live my life among ciswomen as an equal transgender woman.

The problem was, getting to the point of realizing all of this was easy to write about and harder to do. The biggest mistake I made was thinking my gender balance between male and female was so good that I could live as both in the world. While I maintained a long-term marriage and a good job. Trying to go all in on both genders cost me my already fragile mental health as I was still trying to do my research in the public eye about which gender direction I wanted to go. Long story short, I found without too much trouble I could carve out a new feminine life without the world questioning anything about my old male life. As I surveyed the world suddenly, I could see gender possibilities opening for me that I never thought possible before.

During this time in my life, I think I met myself in the middle too fast and tried unsuccessfully to slow my progress down until I could figure out what to do about the rest of my life. Primarily my second wife and my very lucrative job. Plus, on the other hand, I had put this gender teeter totter in motion, and it increasingly looked as if I could not get off. I kept up the old male charade I was forced to live as long as I needed to, and with the help of a few ciswomen friends, I was able to find a new middle point in my life as a trans woman. Which seemed to work well, until HRT or gender affirming hormones came my way, and the balance of my life was changed forever.

I had always viewed the possibility of me taking the gender altering hormones as a line of demarcation of me never going back to my old male life and it was. From the obvious growth of my breasts and hair to the overall softening of my skin and facial lines the changes came fast and furious and again I was forced to move up my timeline to discard (or give away) all my old male clothes and set my sights on a new bright future. Away from all the uncertainties of going back and forth between the two main binary genders of womanhood and manhood. My lifetime of juggling identities went away, my mental health improved as I entered the world I had always dreamed of my entire life that I had finally earned my way into.

The “earn” word is important here because of all the trial and error (mostly error) I put into finally facing the reality of my true gender and forever stopped meeting myself in the middle. Was it worth it? Sure, because I ended up not having any choice after all.

Who Had it Easier

2026-06-06T09:58:37.443-04:00

JJ Hart

The most ridiculous understatement I ever made to myself was thinking how much easier women have it in their lives than men do.

Those were the simpler days of just envying all the girls around me for their ability to wear pretty clothes when I was stuck in my usual boring male attire. As you can tell, my adolescent thought patterns about gender were much shallower back in those days. All I knew was I was having issues with going through male puberty and all its hair and added angles to my body while the girls were adding all the curves I so desperately wanted. It was about that time when I started to further torture myself by having dreams of being a pretty girl when I just had to wake up again to the same old world, I was so tired of at such an early age.

Another benefit I saw from the outside from being a girl was on the dating front. From my ultra shy vantage point, boys had to do all the work to chase a girl but gave it no thought to be a girl with no boys having any interest in you at all. It seemed all my ideas came from the problem I had for years of not being allowed to see behind the gender curtain to go through the insecurities of a girl’s puberty. As their bodies ramp up the necessities for possible childbirth later in life. Which leads me to this, the incredibly short period of time a ciswoman has to level out their hormones and have the chance to live a so-called normal life. First, they have to go through puberty which shapes their bodies then go through child birthing years which strain their bodies and then go through menopause to reduce all the hormones again. Not to mention all the monthly menstrual periods most women must live with too.

In the days when I was busy with just being the “pretty, pretty princess” as my wife called me, she was taking me to task about never experiencing the so called downs of being a woman because I just wanted to appear as one, perfect my makeup and wear my pantyhose and heels as much as I could. For years, I went on clicking my merry way in my heels not giving much thought to what she was telling me. It was not until many years later that my heels finally led me to a path where I could finally learn what she was talking about.

Essentially, what I was able to learn from being a transgender woman and being able to live on both sides of the gender border was that both genders have their challenges. That humans are born as male and female, then get socialized (if they are lucky) into men and women. We transfeminine persons just were born into an unwanted male gender and were socialized into our chosen lives as trans women. The whole process gives us a deeper understanding of the world as we look into who has it easier in life, ciswomen or men.

Since the socialization process of being a male was what I was born into proved to be partially successful one for me, I have always thought men have had it easier. And women have it harder because they must put up with men. Even though, my gender dysphoria issues made me difficult to live with as a husband, I somehow have always found a woman to make the journey with me. Someday, I will have to write a post on the differences of my three wives during my life.

As I continued in vain to find the easy way out in my life, being a guy was the way to go as I found success in being able to bluster my way through in many situations and in others wondering how I would approach them as a transgender woman.

Finally, my gender travel took me behind the gender curtain where I could hear firsthand the experiences of all my ciswomen friends. It was not until then did I realize the grass was not always so green on the other side of the binary gender border. The only problem I did have was reversing all my experiences in the conversations we were having from male to female, so I did not out myself to my friends. I knew I was beginning to be successful when strangers outside of my circle of friends began to ask me questions on what to do about getting along with their boyfriend. I was flattered that other women had trusted me with their problems and were looking for input.

My own socialization journey had taught me that neither gender had it easier. Stereotyping here, men largely bluster and run when they can’t get their way and women are left to raise the kids and pick up the pieces. It is difficult to take such a complex subject such as gender and not stereotype something about it at some point, so I apologize.

I am sure that no matter where you are on your gender journey, you will encounter your own set of standards when it comes to the male and female genders and where you fit. It will certainly be an interesting journey with many individuals trying to tell you to stop. At that point, you must decide if maybe you have had it more difficult than either of the two main binary genders you have encountered. Many of them simply will not have the understanding it takes to approve of your journey, and you will have to move on. But, on the other hand, there could others who approve of you and even want to help. Just be careful that you know which is which.

When it comes right down to it, that girl you envied from afar in study hall, all the way to the woman whose fashion and passing privilege you admired so much both had their own problems to deal with. You just must get behind the feminine gender curtain to figure out just what they were.

When I Quit Recognizing Myself

2026-06-05T10:14:41.964-04:00

Image from Vinicus amiz
Amano on UnSplash

When I thought of the subject of this post, I thought that was an easy topic. From the very first day I had a glimpse of myself in the family’s full-length hallway mirror I partially thought I did not recognize who I was looking at. Sadly, even with all the work I was doing to look like one of the pretty girls I admired so much, I still looked like my male self-wearing a dress with makeup. Most likely, the biggest problem in looking like a girl back then was the lack of access I had to my hair. I was cursed in being raised in an era when young boys’ hair style was short or shorter and a crew cut was considered a longer style. Dad took my brother and I to the barber with him every couple of weeks and we got our burr haircuts without question. If you don’t know, burr means almost no hair which was decidedly not what I really wanted on my head. I had no choice but to go along with the program, and had to use my imagination, along with a towel when I cross-dressed as my authentic self. Who was just learning to express herself. Even if it was only to be to myself.

It turned out to be years later that I began to be skilled enough to begin to match my exterior self with my feminine inner feelings. I had help from a professional makeup artist I will never forget who had the skill set to show me what I doing wrong with my makeup and the verbal skills to explain to me how to improve my life through ideas such as foundation basics to cover my beard and contouring my face to bring out the highlights I did not know I had. When he was finished, I truly did not recognize who I was looking at in the mirror. Plus, I really enjoyed all the compliments I received on my appearance from several of the attendees at the transgender-crossdresser social mixer I was attending. Once I was given that basic skill set to make myself up, I was able to start buying higher end cosmetics which flattered me even more.

In many ways, for a while when I did not recognize myself in the mirror, it scared me. Because I was losing touch with all my male past which had made me…me, for my entire life. I was shocked the first time I lost some of my basic male privileges I had always taken for common I would have such as my intelligence when I talked to men and my personal safety when I found myself in contact with a toxic one. Quickly, I needed to come up with a plan to support my new life as a transgender person without the old ways which I had been successful with until I could develop new ones.

Of course, too, there were my usual problems dealing with gender dysphoria when I thought I had done a wonderful makeup job only to see my male self-looking back at me in the mirror. Then, to add insult to injury, if I was being successful in navigating the world as a transgender woman, my impostor syndrome would set it. Impostor syndrome to me made me feel as if I was an impostor in the world of ciswomen and should not feel as if I belonged there at all. Who knew, just being a trans woman would bring all the baggage with it. When I ceased to recognize myself, I learned all the rest the hard way.

Even with all the new roadblocks, I began to do more than just survive in the new feminine world I found myself in. I began to thrive as I started to carve out a new exciting life where no one knew anything about my past as an unhappy man. I never let on to my past except to let strangers know I had been married in my past and had lost my spouse to a heart attack without ever mentioning which gender she was. As well as mentioning I did have a daughter when it came to family discussions. Technically, even though I did not birth her, I was in the delivery room for her birth which was as close as I could come with the circumstances I had to deal with.

Finally, I arrived at the point when I cherished the times when I did not recognize my old self and hated the times when I could still see his image slipping through when I looked for the first time in the morning in the mirror before I had a chance to put on any makeup. Rather than feel anymore of the pain of gender dysphoria, I got to the point of thinking I was stuck with what the world had given me as far as my appearance went. The idea I used worked well because I felt I never looked as bad as I thought and certainly not as good as I arrived at the point where I was erasing my male self for good.

I would be remiss if I did not mention the role gender affirming hormones or HRT played in all my progress in my lifetime male to female femininization project. While the hormones did not make me anymore or less of a trans woman. They certainly made me feel the process more. Almost immediately, as my skin began to soften and my breasts began to grow, I began to feel emotions flow through my body that I had never felt before in my life. My facial angles also began to soften, allowing me to do less contouring with my makeup when I went out was one of the good things which happened. Along with me not recognizing myself when all a sudden it was me who was reaching for her coat saying she was too cold in a venue, and I was not making it up.

I guess you say I covered about as much ground as I could erasing my old male self without going through any major (or minor) operations. But I did make it to the point where I did not recognize any of my old self anymore.

When Nothing Else Mattered

2026-06-04T10:01:43.054-04:00

Image from Klara Khokhlova
on UnSplash.

Perhaps, similar to many of you, you have been described as selfish when you pursued your gender desires. I know, I was by my second wife as she told me many times my desire to be a pretty cross-dresser in my life was not all about me.

During this time of my life, sadly or not, all my spare thoughts and time dedicated to my cross-dressing activities, so yes, it was all about me. I did my best not to be that way, but I was failing miserably. Especially when I figured it out, I could leave the house as me and do a portion of the household chores such as grocery shopping. I figured by doing so, I was helping my wife and at the same time helping myself.

The more proficient I became at doing my new portion of some of the weekday household chores, the more I felt that nothing else mattered to me than my quest to explore my inner femininity. Increasingly, I broke the rules and made excuses to leave the house and explore the new, natural and exciting world I was experiencing.

As years always do, mine flew by in a blur as I became more proficient in perfecting my feminine appearance and it began to be more apparent to me that the life as I was living as a man would have to be sacrificed at some point if I wanted to pursue my dream goal of living as a transfeminine person. That is when I began to fall back on my ill-fated male habits of internalizing all my feminine feelings. Hoping that eventually, they would just go away. Compliments of my latest purge of my cross-dressing belongings.

Very soon, it became evident that all the purging in the world would not rid me of my deep-seated gender issues and nothing else began to matter, not even the massive fights my second wife and I were having when she caught me out of the house as myself. I would go to any extent possible to try to mend the wounds from my breaking the promises not to ever go out again unattended, all the way to promising I would go to a therapist in Columbus, Ohio who specialized in gender care to attempt to solve my “problem.” Even then, I would not listen to the therapist who told me that my gender issues were not a “problem”, and there was nothing she could do about them. I made the mistake again of thinking there was something radical I could do about how I was attempting to live my life. I could keep trying to sneak out of the house and try to learn more about my possibilities of living life as a transgender woman, while at the same time continue to live with my wife. She always know I was a cross-dresser but was completely dead set against me going any further towards being approved for gender affirming hormones (HRT) and living as my authentic self.

Perhaps the biggest problem was I was not sure what my authentic self really was. I knew I loved my second wife as much as the day I married her years before, but I really was not sure of how deep my transgender issues were going to run. Plus, all the research I was doing into a new life, jeopardized my old life which at times was not so bad because I was accumulating all the male privileges such as wife, family and job that I did not necessarily want to get rid of. The whole situation just mentally tore me up as I did not know what gender I was going to be from day to day. Was I going to try to be my true self or go out into the world again and “act” like the strong man I was not.

It all led me to feeling completely detached from the world and wanting to end it all because I felt so worthless to everybody. Fortunately, after I hit rock bottom, I got help from a good therapist and was prescribed medications which helped my on-going Bi-polar disorder and anxiety. It turned out my anxiety was triggered in many ways by my gender issues so that was easier to solve, but my depression was not so my new meds really helped. Giving credit to where credit is due, my help came through the Veterans Administration health care system and as luck would have it, I was teamed up with a therapist who knew what she was doing when it came to depression and LGBTQ care.

By this time, my second wife had tragically passed away from a major heart attack leaving me totally alone with my thoughts. Quickly, since nothing else mattered, I took the path of least resistance into my own form of womanhood. All those dues I was paying as a cross dresser working with my appearance came back to help me when I could hit the ground running in my heels (not really) and concentrate on rounding out my persona of the trans woman I wanted to me in the world of alpha cis women around me. I was able to see and learn from what they did to make their lives more fulfilling as women, and I wanted to do that too. I was having fun while at the same time was secretly learning everything I could from the ciswomen around me.

Most certainly, nothing else mattered when I sought out approval for my gender affirming hormones from a doctor I found in an LGBTQ newspaper. Along with the hormones, I was putting my new life together by legally changing all the gender documents I could with the VA and in the civilian world. Very soon, my old male life was in my past and my “dead” name faded away.

The only thing that did matter was building a new life with my third wife Liz, a lesbian ciswoman who accepted me for what I was. I could not let a second chance such as that pass me by.

Gender Evolution

2026-06-02T10:07:57.319-04:00

Image from Hoite Prins
on UnSplash.

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

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

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

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

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

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

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

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

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

Thanks for reading!

Visiting the Vampires

2026-06-01T10:10:53.139-04:00

Image from Mike Lloyd
on UnSplash.

Today was a rushed visit to the Cincinnati Veterans Hospital for bloodwork before they shut down for a week to switch over to a new digital system that we all know will cause new headaches.

Most all my bloodwork can be done at an off-site closer clinic to my house which does not require a trip downtown into a very congested area. Plus, with my mobility issues, it makes the entire process of going downtown for specialized work very unpopular with me and my wife Liz who must do all the driving.

The specialized test I needed to get done before the shutdown June fourth was for my Estradiol blood levels. For some reason, my levels had dropped nearly fifty points from a level they had been at for literally years. For that reason, my endocrinologist requested another test of my HRT levels. When this level comes back, if it stays low, it will be interesting to see what ideas she has, such as maybe doing away with the patch system and switching to injections which for no real reason, I have always stayed away from. I am not afraid of needles; I am just lazy about the possibility of giving myself injections. One way or another, I will have to jump off that bridge when I come to it. I think my hormonal levels have jumped back up because of an overall increase in the fullness of my breasts, so I may be jumping to conclusions I did not have to.

Past that, we were able to beat the rush this morning at the VA because the vampires (blood lab people) open up at six thirty and we were able to get an early start and be there before seven. For the appointment, I chose a three-quarter sleeve feminine lace trimmed blouse, leggings and flats. Along with a light application of makeup which seemed to work because I was not misgendered at all and was actually smiled at by several men who passed me by on the way to the second-floor labs. I will take that as a win everyday since I have had mixed results over the years at that hospital. Usually, the smaller clinic I go to is better because they know and remember me, but they just could not do the specialized Estradiol test because they needed to send it out for testing.

Now I play the waiting game (which if you were in the military, you know what I am talking about) before I can get the results back. I doubt if it will be very soon because of the overall system disruptions which are coming up.

This is a short post today because it is my transgender grandchild’s birthday today who is working up in Maine and I have to send them birthday wishes plus a small gift. Happy Birthday “A.”

More Serious Stop Signs

2026-05-31T10:07:06.961-04:00

Image from Steve Lieman
on UnSplash.

“Tia” wrote in yesterday and commented on my recent “Stop Sign” post. She wanted further insight into what my biggest stop signs were and how did I get through them.

First, thanks for the insightful comment, Tia and here are the answers as I remember them now.

By far, my biggest stop sign was put directly in my path by my second wife. As I was stuck between the rock and the hard place with her because of the transition I was slowly making from cross-dresser to transgender woman and my wife. Rightfully so, my wife pointed out I was breaking the marriage covenant we had and she did not want to be married to another woman. The last thing I want to do here is make her the bad person in all this gender turmoil because she knew and accepted my cross-dressing before we got married.

She even went as far as attending the social activities I went to in Cleveland and Columbus, Ohio and supported my efforts to leave the house to explore the world as a transfeminine person for the first time by backing me with money for motel rooms to get ready in. The only real stop sign I had was to agree to never leave the house dressed as me. Was it enough for me? No. I blew right through the stop signs and started to throw caution to the wind and go out into the world like the authentic me. Regardless of the heavily populated area of town, we lived in.

I kept on doing this until I was caught time and time again by my second wife and could not lie my way out of me breaking our agreement. I resorted to even going to therapy for help which never actually came. Mainly because I was not doing anything wrong in my struggle to just be the inner female I always thought I was. I even had a therapist I respected totally tell me that and I just ignored her. Thinking I could balance my gender issues and fight on to maintain the status quo. By ignoring the stop signs I was facing, I was just making my life worse and not helping our relationship in the long term which I will get back to later. Because, as it turned out, there would not be a long term relationship anyhow.

In the meantime, as I became more serious about the possibility of living out my life as a transgender woman, I began to see other stop signs ahead. They were major signs too such as how I would support myself in the world without my wife and perhaps the rest of my family. Obstacles which face nearly all transgender women and transgender men as we attempt to cross the gender border and live out our lives as normal everyday citizens. It is difficult to end one life, pick up the pieces and start over again. Something I wish all the transphobes who try to attack us would try to understand but that is a whole other topic.

Pure destiny helped me to negotiate the other major stop signs I faced with the attitude that if others could complete a male to female transition, why couldn’t I. Life became a circle for me as I went through the darkest period of my existence before I was able to pay my dues and take advantage of the new world I was in. The most tragic part was losing my wife to a major heart attack. I never ever thought she would ever die before me with the stressful lifestyle I was leading but I did, which led me to wonder what I would do about the biggest stop sign of all in my life. In the new darkness as I searched for my new path which had existed so long. All I needed to do was remove the stop sign and continue to live.

I also found I needed to do a quick look into who was important to me in my life and who I could afford to lose if I crossed the gender border. In my darkness I guessed my daughter who would support me and my only brother would not. Which was exactly what happened. It has been over a decade since I have talked with my brother, and my daughter has become one of my biggest supporters. My parents had long since passed on so I did not have to worry about coming out to either of them. Even though I did try to come out to my mom years ago and was rejected. I took that stop sign down and forgot about it.

It seemed, once I got used to taking down my gender stop signs the easier it got. Although that was not necessarily the case. Destiny stepped in again and provided me with an age excuse when it came to how I was going to support myself. I was fortunate to have worked a good job with a good wage which helped my Social Security retirement payments. I turned out if I was able to sell the collectables my wife and I had collected over the years, I could retire and support myself. Which saved me having to look for a job as a new transgender woman.

Of lesser importance was when the Veterans Administration started to provide care for gender conflicted veterans such as me. I jumped at the chance for lower cost HRT meds and the mental care to get them. The mental care provided me with a qualified therapist who helped me with the legal documents that assisted changing my legal gender markers within the VA and the public sector.

Perhaps removing the biggest stop sign of all that remained was discovering a loving relationship which I could cherish for the rest of my life. That person of course was my wife Liz who discovered me on an online dating site. I was always a social person and had resigned myself to a life of being alone before I met Liz and we are still going strong over fifteen years later.

I hope all of this answers the questions Tia and all of you may have had about my transgender stop signs and how I handled them. Some stopped me for years while others I simply rolled through or ignored altogether but one way or another I made it. As always, all of your comments are appreciated!

Looking Both Ways at Stop Signs on my Gender Path

2026-05-30T10:11:52.587-04:00

Image from Alex Azerbache
on UnSplash.

I learned the hard way; I needed to look carefully both ways when crossing my gender path from male to female. If I did not, I ran the risk of being caught in the wild world of everyday traffic around me. When I left my mirror for the first time, gathered all my courage and went out into the world, I discovered basically three groups of people.

By far, the biggest group I didn’t need to pay much attention to were all the people who were going about their lives and not needing to notice anyone else. The second group was smaller and mostly just curious. They were mostly women and were curious why a man would leave a life of privilege to want to live as a woman. Or at least try to look like one. Sadly, the most vocal of the three groups were the gender bigots, TERFS (cis women who hate trans women and want to deny our existence) or just plain haters who wanted to make my business theirs. I learned the hard way several times to take nothing for granted when I went out in the world and look both ways at stop signs on my gender path.

I also learned the hard way that no matter how good I thought I looked and moved on a certain day, someone would always see through my efforts to be a presentable transgender woman and take exception with it. Some were mean and wanted to make fun of me, and some were not but I always had to be aware of the possibility of ill-will coming my way. I needed to come to a full stop until the unpleasantness went away, and I could go about living the new life as a transfeminine person I felt so comfortable in. When my confidence began to grow to a point where I could navigate most of the public comfortably, I did not care what the occasional gender bigot thought, and my confidence turned out to be my biggest weapon against hatred against me. It was tough to do, because the confidence was so frail but somehow, I was able to do it as I became more effective in my feminine presentation skills.

It probably was because this was the time of my life when I was obsessed with every little aspect of my appearance as a woman. Every now and then, I take the time to go back and read some of my earliest posts and I am continually amazed about appearance centric my writings were woven around. Just the right amount of makeup and how I did my eyes, all the way to just the right accessories to go with my outfits were prime examples of what I was writing about. It was no wonder that my second wife delighted in calling me the “pretty, pretty princess” when she told me I knew nothing about being a woman.

Rather than discourage me, her comments spurred me on to try to figure out what she meant. All along I thought I was the ultimate student of the ciswomen around me, only to learn I had not yet scratched the surface of what I needed to learn to earn myself a spot in the girls’ sandbox. Looking back, I do think my expertise in making my feminine appearance better did help me because for the most part (except for my wife) most ciswomen knew I was serious in my journey to be let behind the gender curtain as I needed to stop on my gender path, look both ways for ciswomen, let them through and then move ahead on my own. And by the way, the “princess” got her revenge one night when my wife needed to ask for advice on which makeup to wear.

When I finally was allowed to play in the girls’ sandbox, the stop signs I routinely faced really began to multiply. I had gone the extra distance to lead my inner feminine trans person out of the mirror and into the world by doing a deep dive into the basics of makeup and appearance all the way to working diligently on my feminine movements so I would not look like a linebacker in drag in heels at the mall. All my efforts worked out so well that the world wanted to communicate with me. Which put me into shock because I was woefully short on any experience to do it. All I had ever done was speak very briefly with cashiers and was not prepared to carry on any sort of a conversation.

All I did know was ciswomen communicate on a different wavelength than men and I needed quickly to find out what it was and how to do it, so I could survive my next stop sign. Surprisingly, I was a quick learner and mimicked the women around me the best I could until I became semi-comfortable in conversations with them. Primarily, I learned that for the first time in my life I needed to listen closely to what another woman was telling me because she could be talking in feminine “tongues.” In other words, I learned ciswomen use a lot of nonverbal communication when they don’t want men to know what they are talking about and use a lot of passive aggressive words when they communicate. When I stopped at the verbal stop sign, I needed to use extra caution to make sure a smiling face was not hiding behind my back aggression when we interacted.

I survived my communication days partially from taking feminine vocal lessons which specifically helped me to use terms which were more feminine in nature and not so male orientated. Which I was used to. I said I was a quick learner, but learning fast was all I could do to survive in the new feminine world I loved so much. I found myself immersed in a labor of love that I wanted more and more of every night that I spent interacting socially with my ciswomen friends. It was like I was back in grade school again learning the basics of being a quality feminine person.

From then on out, the only stop signs I saw were the ones I learned on my new path with women to stop at which they had done their whole lives and I was making up for in my own way quickly. The “pretty, pretty princess” had grown up, but sadly my second wife missed my progress when she tragically passed away early in life from a massive heart attack. I don’t think we could have ever stayed together. Being friends on the other hand was probably a possibility because we were together for twenty-five years of our lives. It will be forever one of the mysteries I will never solve. A giant stop sign.

No Participation Awards for a Trans Woman

2026-05-29T09:59:18.466-04:00

Image from Brett Jordan
on UnSplash.

As I traveled up my very long gender path with all its stop signs, I realized there were no awards for just participating coming my way. In fact, just the opposite was true.

Every time I was able to cross dress in front of the family mirror and not get caught, I experienced major gender euphoria but no awards because I knew I would just have to go back to my boring male life which I wanted no part of. Since my feminine self was deeply hidden from the world, there were no awards when I mastered a certain make up look or did not run my panty hose. On the other hand, I could expect some sort of gratitude when I achieved good results as a boy. I hated the total imbalance of the system I needed to live under with no available choices coming my way soon.

It wasn’t until much later in life did, I began to experience any participation awards at all. In the very beginning after trips to the big malls I was going to, even on the nights I was laughed at and scorned for my appearance, I felt at least I had tried and needed to go back to my cross-dressing drawing board to come up with ideas about what I was doing wrong. After setting aside my stubborn ideas of trying to dress sexy like a teenaged girl, and dressing age appropriate I was able to blend in with the ciswomen around me and not cause any undue attention to myself. I gave myself a bigger reward when I reached that major milestone in my life back then as a part-time cross-dresser.

Then, I became frustrated because it seemed the awards began to become harder and harder to come by as I started to overachieve as a transfeminine person seeing the world for the first time. Those were the days of trying to overcome a portion of my guilt for sneaking out of the house dressed as me by trying to do things which helped the household such as grocery shopping or better yet, trying to find my wife a garden gift at one of the nearby antique malls I went to. She was a huge gardener, and I thought an occasional gift would please her but probably pleased me more because it helped soothe my guilty conscience and gave me an imaginary award to put up on my mantle. I wish I could say I had a lot of awards, but they were very difficult to come by. Plus, my collection would be destroyed every time my wife caught me out of the house, and I became discouraged and decided to purge all my feminine belongings only to have to start all over again. Until I realized purging was fruitless and my desire to be a woman ran too deeply than just having the clothes, shoes and wigs that I had collected.

Overtime, with all the purges I attempted, I became better at keeping key items of my wardrobe I would need if (ha-ha) the urge to be a trans woman hit me again. I was not the sharpest tack in the box and still had not realized being trans was apart of me and would never just go away.

In the meantime, I continued to go out at night in the world and collect my participation awards as I learned what it really meant to be myself. To do so I needed to leave the gay bars behind that I was frequenting where they only thought I was a drag queen and try out the real world for a change where at the least I could be accepted as a woman from a different past. To do so, I needed to hitch up my big girl panties and do a deep, scary dive into the world I wanted so desperately to be in. I was growing increasingly tired of living a lie as a man and wanted out. In the beginning, I still took what I thought was the easy way out. By going to venues, I frequented often as a man and had wondered how it would be to live it as a transgender woman. It also helped that I was able to see how single women were treated in the straight places I was considering going. The last thing I wanted to do was to feel unwanted or afraid being a single woman in a venue full of couples.

After much thought and caution, I tossed my misgivings aside and considered what was the worst that could happen. My frail ego would be destroyed, and all my participation awards would be destroyed was my first thought. Then, I relied on all my new-found confidence as a transgender woman to succeed at my first big moves in straight venues in the world around me. To my amazement, I was treated well in my new world, and no one laughed at me or treated me with disrespect as I left my unwanted male privileges behind to learn what all the female privileges were all about.

I learned immediately one of the benefits was just being treated nicer. Even to the point where I was invited to staff girls’ nights out when the bartenders were concerned, I was lonely. Which I was. Better yet, one bartender set me up with her single lesbian mom whom I remain friends with to this day. Ten years later. There would have been no way that I could have made friends as easy as I did as a woman than I ever did as a man. A major reward for all the years of work I had put into succeeding on my gender path to my dream.

Another major reward I have received over the years comes from all your comments and feedback to my experiences. Originally, the idea was to write a blog (before I even knew what was one) to help others with similar gender differences so they could learn from them. Thanks to you, the idea has grown way past my expectations.

Thank you!

She Was Living Rent Free in my Head

2026-05-28T09:29:54.780-04:00

Image from Nathan Dumlao
on UnSplash.

It took me years to realize that I had a tenant living rent free in my head all along.

I should have known from day one when I was going through my mom’s clothing that she was here to stay. In fact, she increasingly demanded more and more space in my head to justify her life as a cross-dresser or transvestite as we were called back then. I would need to wait several years for the transgender term to even become popular in our gender diverse society.

Also very early, I realized that the small closet I gave her to exist in just was not going to be enough. When she succeeded in expressing herself in the world in the smallest of occasions, she wanted to increase her space in my head. Prime examples were the days in school during study halls when I should have been actually studying. But I wasn’t as if I was having too much fun envying the girls around me who I desperately wanted to be like the next time I had the rare chance to be by myself and cross-dressed as a pretty girl in the mirror. And I realized I did not want them sexually as much as I wanted to be them physically and mentally.

It was during that portion of my life that I completely did not have any idea of how much rent-free space my evolving trans woman needed for her share of my head. Now I want back all the time my male self-spent fighting her for my life as I lived it. The gender ripping and tearing was certainly no fun, as both genders in my head fought for their right to survive. For awhile I tried the old male fallback of just try to ignore my number one problem in my life and she would somehow just disappear. When, in fact, the opposite was happening. The thrill of putting on a dress, hose and makeup would go away, and in its place, I would have a deep-seated feeling of just doing what was coming to be just natural for me. It was increasingly evident that I would need more space for my rent-free tenant to operate in as she went out to explore the world as a novice transfeminine person.

Following more than a few rough patches when she was going out in the world, my woman began to understand the sacrifice of her male ways it would take to survive. She became more serious and began to work on the basics such as presenting herself convincingly in the world. I went on a crash diet and succeeded in taking off enough weight so I could go down a size or two in the world of women’s fashion and I could find and wear stylish clothes for a change. Along with that major move, I began to take extra better care of my skin. Using a good moisturizer following every shave. Which paid off by not having to use so much foundation makeup and I could look so much more natural as if I was not trying so hard to look like an attractive woman. The trips I started to make to the department store makeup counters for guidance certainly did not hurt my progress either.

I was learning the hard way that I could not cut any corners if I was to be successful in my quest to present successfully in a world of curious ciswomen. I needed to give my rent-free tenant the opportunity to expand her space in my head and the finances to do it. I would be spotted a mile away as a man trying to be a woman if I used cheap makeup and did not do my best to shop for (and try on) clothes that fit me and even flatter my testosterone poisoned figure that I could do very little about. I did learn from my observations of the ciswomen around me that there were women of every shape and size that I could copy from and be successful. Which gave me the positive energy to carry on and pass as a trans woman friend of mine said, “Out of sheer will power.”

Even though the progress of my rent-free tenant was not moving along as fast as she wanted, there were still major obstacles in my way to deal with. Such as what would happen to my twenty-five-year marriage, my relationship with my daughter and the problem of finding a new job as a trans woman in the world. To be sure, all were major obstacles to deal with, so my tenant would have to be patient as she was beginning to understand she was the only tenant left in my head with any power. My male self was just going through the motions of life to keep a job and the outwardly show of male privilege in my life.

Finally, it was time to go on gender affirming hormones and allow my tenants to switch places. My previous rent-free tenant had earned her right to live as the dominant person in my life and my male self was left to pick up the pieces. I should say baggage more than pieces, because that is what he left me to consider in my new feminine life as a fulltime transgender woman. It was difficult to do, but I was able to keep several of my main male building blocks of my life such as my will to succeed and a deep-seated desire to bring my hobbies with me such as my love of sports. Which I learned was alright when I made ciswomen friends with the same passion for sports that I had built up over the years of my life.

While I certainly would not recommend a life like mine to anyone. Letting someone live rent free in your head for all those years was never easy. Perhaps, the only positive was, having all that time to learn the world as a trans woman gave me a stable basis to work from. That is my excuse, and I am sticking to it.

Transgender Challenges

2026-05-27T10:07:51.527-04:00

Image from Beta Builders
on UnSplash.

For me, the challenges of being a transgender woman ran deep and came often.

The first challenges I faced were just keeping my small collection of feminine belongings secret from my younger brother and parents. From there, my dealings with my cross-dressed self and the world only would intensify as I grew up. Very soon, the move from closet to the mirror would not be enough to satisfy my gender curiosity, and I began to leave the house when I could dress in my clothes and makeup for small walks to our rural mailbox. As puberty took its toll, finding anything to wear became my biggest problem because I was outgrowing my short mom’s clothing. She was only five foot two.

Somehow, I beat the challenge of keeping my deep gender secret to myself and kept up my routine of taking every spare moment to satisfy my desire to be a girl. Of course, it took me awhile to come close to perfecting anything which came close to being acceptable when it came to applying makeup and even shaving my legs. Which I was probably sneaking around and doing before most of the girls I was around who I envied so much. As it turned out, the magic of makeup really escaped me until I had the courage to accept the challenge of having a professional makeup artist do my makeup (and explain what he was doing) at a transgender-cross dresser social I was attending in Columbus, Ohio years later. The makeup pro taught me the basics of foundation, contouring, eyes and lips among other helpful tips. All the compliments I received showed me I was indeed on the right path I had chosen in life, and I could at least expect to fit in with other ciswomen in the world on a regular basis.

Then, as I always point out, the real work and challenge of what I was setting out to do set into my life. At the same time my male counterpart was beginning to establish himself as a successful person in his chosen career. As much as my self-destructive personality kept trying to tear down all he accomplished, it never worked, and he succeeded anyway. Which meant he was increasing the amount of potential baggage I would have to account for if I was ever going to reach my goal of living as a successful transfeminine person.

What hurt me was when I miscalculated what it was going to take to live the life I always dreamed of. The challenge was making the jump of just looking similar to a ciswoman, all the way to having a basic idea of how she lived her life. A great example of how my cross-dressing fun and games became very serious when just after I decided to go full time as a trans woman and had given away all my male clothes, my wife Liz’s dad passed away and I needed something appropriate to wear to the viewing and funeral. I was fortunate that I had several items of clothing in black, so I could be properly dressed for the occasion. A long way from the day-to-day life I was expecting to challenge me as I went through my male to female femininization project.

It turned out to be a huge step in my life when I finally accepted the challenge to live the life, I was always destined to live. I was no longer the lost kid in the mirror desperately cross-dressing his life away dreaming of a world he could not be part of. I was a full-fledged adult with a rapidly clearing view of the challenge ahead if she wanted to survive. Perhaps you noticed I used the “she” pronoun as I increasingly adopted it as my referred self. It made me feel more complete as a transgender woman. If I did not believe in myself at this point of my life, how could I convince the world who I was anyhow.

The next big challenge to me was seeing if I could be approved for gender affirming hormones or HRT which I am still on (thankfully) to this day. Before I did anything with the hormonal challenge, I knew I would have to seek out a doctor’s approval to see if I was healthy enough to do it. I was able to find an ad for a doctor in nearby Dayton who said he specialized in hormonal care and I made the appointment which would change my life forever.

In our first meeting, the doctor gave me a brief physical, asked me a few questions about what I knew the HRT would do to me and started me on a minimum dosage to see if there would be any ill effects. There were not, and very soon I was on a larger dose of the magical hormones my body seemed to take to naturally and the changes to my body were on. In fact, the changes began to happen so fast, the challenge then became to move up my timetable on when I was going to give up what was left of my male existence. It was becoming increasingly difficult to hide my growing breasts, softening skin and long hair from the public and all the internal changes such as emotions from myself. I finally had enough and embarked on the greatest challenge of my life at the age of sixty. I put nearly half of a century of a part-time cross-dressing life behind me and never looked back.

Destiny helped me too, when the Veterans Administration health care system which I was a part of began to treat gender dysphoria in veterans with hormonal care. I needed again to go through the approval process and made it again as it seemed as if the challenges would never end. It was worth it because it tied me in with the VA’s mental health system for my depression and anxiety issues. As luck would have it, I was paired up with a mental health professional who I was with for years and helped me with all my issues such as having my legal gender markers changed within the VA and society at large.

I guess the challenge of any first-time experience can be traumatic for any human being. It just seems unfair that transgender women and transgender men have more than their fair share of challenge.

The Original Witches Ball as an Up-and-Coming Trans Woman

2026-05-26T10:16:30.833-04:00

JJ Hart.

Back in the day, the Cincinnati area used to host what was called the “Original” Witches Ball around the Halloween season of course. It was called “The Original” because several copycat dances had sprung up attempting to copy the success of the first one. Of significance to me was the ball that year was actually the third date my wife Liz and I had been on. Our first two dates had been to a drag show and a Renaissance festival, so another themed date would fit right in until we got to know each other better.

Perhaps the highlight of the witches’ ball was the venue itself. It was in a huge vintage Victorian house which had been expanded in the past to include an auditorium with a balcony and stage. For the evening, I thought I would go all the way in black with a hand-picked outfit guaranteed to be fun and just a little on the sleezy side. I went with a short black sleeveless minidress with black panty hose, a sequined net shawl and black heels. Since I was not quite to the point where I could style my own hair and wear it, I decided to wear a long curly black wig I had purchased a long time ago. For the party, we were even able to reserve a nearby hotel room so we could get ready and spend the night without having to worry about driving since it was within walking distance.

As I was to discover later in the evening, the only mistake I made in my outfit was the high-heeled shoes I chose to wear. As the night wore on, so did the strain the shoes put on my feet. Fortunately, I was able to kick them off at key places in the venue which had carpeted floors. I guess you could say I paid the price for fashion the night of the witch’s ball. Other than that setback, I had a wonderful time with Liz enjoying the entertainment on the main stage. The costume contest (which I did not enter) and all the exotic belly dancers who performed during the evening in another part of the venue.

All too soon the party was over, and my head was still spinning over all the wonderful costumes I saw, all the vendors with their merchandise and even getting an introduction to the “Captain Jack Sparrow” impersonator who complimented me on my “costume.”

I was hoping the alcohol I consumed would dull the pain in my feet for the walk back to the hotel in my heels, but it didn’t and off came the heels and on came the sidewalk in my panty hose for the short walk back. For all the fun I had, the brief pain was worth it. Little did I know at that time, I would be able to return to the witches’ ball in the future in a much bigger role as a behind the scenes organizer. And Liz and I would be able to cement our relationship with other entertaining dates.

It turned out that the witches’ circle Liz was already part of when I met her wanted to try to take on the huge task of organizing and putting on another annual ball. The first thing they needed to do was negotiate a rate for the same venue, which was crucial for the success of the event. Since I enjoyed being part of the group putting together another ball, I was given the opportunity to set up a vendor’s table to sell cookbooks and other crafts the group had put together. The fact was not lost on me that I had transitioned with all of them from a transgender woman to just another integral part of the group. Or circle that it was referred to.

We only managed another couple of balls in the original venue it had was so uniquely designed for. Old and spooky to start with, it was simply ideal for what we wanted it for but the newer future places just did not come up to its standards of uniqueness, and the attendance began to decline. I did add an image showing what I did wear to the last of the old-style Cincinnati Witches Balls. I chose my black silk pants with a red sequined sleeveless top with my own hair this time around topped off with an oversized black hat you can’t see in the picture. Furthermore, I learned my shoe lessons this time around and wore a pair of sensible flats. The only positive I got from researching where we could have our next event was being invited to visit possible venues. Many of which were in Cincinnati brew pubs which meant I could sample some good beer.

These days, the Witches’ Ball event still hangs on in a vastly smaller form as it is held now only in a local bar. I, however, will always remember what the event meant to me. I was able to express myself for the last time in a hyper-Halloween atmosphere where I attempted to dress as a sexy woman and this time with a date who would become my wife later in life. From then on, I transitioned male to female into a world I had only dreamed of and any work I did on the ball was from my new viewpoint. Not to mention, I really appreciated the lack of special attention I received just because I was a trans woman in a group made up primarily of ciswomen and a few men.

I would have never thought just going to such a special venue for an outstanding event would lead to such far-reaching circumstances for me. It proved once again how life can be a strange but wonderful set up of possibilities which are there for you if you can ever set out to achieve them. For many of us that is the problem which hurts us in life. If it is something you can’t overcome.

Thanks for reading along and adding your comments. It makes it all so worthwhile for me!

Memorial Day 2026

2026-05-25T09:10:33.063-04:00

Image from Richard Sagredo
on UnSplash.

It does not seem possible to me, but another Memorial Day has come and gone. A time to remember the weekend means so much more than just another day off to observe the official start of summer.

Being yet another survivor of one of our countries’ endless foreign wars makes me feel resentful that so many lives were wasted. My time to serve came during the Vietnam War and I was proceeded by several soldiers I knew who never made it back home without paying the ultimate price with their life. That is what Memorial Day means to me, and it should always be a solemn observance for all of us.

Then, what about all our transgender brethren who served in those thankless wars who died without ever having the chance to live a life as their authentic selves. Many enlisted to prove their manhood and ended paying the ultimate price in combat. They need to be remembered too.

I know this is a very short post by my standards, but I just wanted to pass along my deep felt thoughts on this special day for me. The day which is not for all veterans who served. Just for the ones who gave it their all.

Take the time today to remember them all.

You Never Know until You Try

2026-05-24T10:06:10.639-04:00

Image from Leo Visions
on UnSplash.

You never know until you try was drilled into me as a kid by my WWII generation parents whenever I was facing a potential difficult situation. Little did they know, their insistence on me trying to do the improbable would come back to haunt them in a very different way. Back in those days (in the 1950’s) gender issues were referred to as mental illness and any reference to their eldest son being mentally ill would have been frowned on, so I was stuck wondering if I was really a boy who wanted to be a girl.

The only thing I knew to do was to keep cross-dressing in front of the family’s full length hallway mirror. Imagining I was one of the pretty girls I desperately wanted to be. At the time, I had no idea my gender issues would last the better part of fifty years and take up huge portions of my life. Not that I could have done anything about it if I had tried which I did a number of times when I purged nearly all my feminine belongings swearing never to pick them up again. I was stuck being a male and somehow, I needed to make the best of it. Like so many people I knew with gender issues, purging never worked. The pressure built until I could take it no longer and again, I was accumulating women’s clothes again and wearing them.

At the least I tried to go back to mentally being male full-time and failed miserably at it. All I knew was when I was not thinking about getting out of my dark, lonely gender closet, I was not happy at all and when I at least tried to be me in the mirror it took the pressure off. Even if it was only for a while. At the same time, I was acutely aware that I was doing the best I could to see if I could improve my appearance as a pretty girl. How I never got caught doing all of this, I will never know, and I even resorted to taking plastic bags of clothes and makeup into the neighboring woods so I could escape the prying eyes of my slightly younger brother and family.

My mentality of never knowing you could do something until you try really came to the forefront when I was drafted into the Army during the Vietnam War. Instead of taking the two-year plan with a ticket to Southeast Asia, I took a chance and signed up to try to get a job I wanted in the American Forces Radio and Television Service. With a lot of luck and the help of a congressman whose radio station I worked for, against all odds, I got one of the sixty job slots in the Army for AFRTS. It turned out the whole process turned my life around and taught me that anything could be possible. If you went out of your way to try. Probably the most valuable lesson that I could have ever learned as I looked ahead at my path to becoming a successful transfeminine person. If it had worked for me once, why couldn’t it do it again.

As I set out to leave my gender closet behind and improve my life, I know I took on a journey I would not readily recommend to others. When I started to leave the mirror and join the world as a trans woman, I used a tool that I had already used effectively as a man in my previous life. It was alcohol, and I knew I could use it to build up much needed courage to be in the world as a transgender woman and not get myself into more trouble as I was presenting as a single woman in an establishment which served alcohol. Gay, straight or lesbian, it did not matter. I found I could get by if I stayed out of the redneck leaning venues. I was also well schooled in the artform of driving while buzzed from all my days in the Army when I did all the driving. More than anything else, this was back in the days before the major crackdowns on drunken drivers, so I was safer, and in NO WAY do I recommend what I did.

Also, what I think is tougher these days than when I was intensely lonely and looking for companionship is the world of on-line dating. When I was seeking a date, I played both sides of the gender coin, because I was in the unique position of being a transgender woman who favored lesbians. Looking back, I think I got the most attention from men seeking men dating sites. But just knowing that the amount of trash I would receive was at its best humorous and at its worst, a disaster because I refused to meet anyone in a public place which was not of my choosing. I was stood up more times than I would care to count or remember because my life was destined to change forever when I met my future wife Liz on a woman seeking woman dating site.

Liz responded to my picture saying I had sad eyes which was entirely possible at that time of my life. Amazingly, she lived relatively close to me in a town (Cincinnati) that I had always admired. From there, I began to become involved in her friend’s girl’s nights out and I was able to do more to learn what was behind the gender curtain than I had ever thought possible. The entire on-line dating world for me proved again you never know what you are going to get until you try.

These days again it is more problematic to find someone online with all the scammers out there, but destiny can never find you if you never venture out of your dark lonely closet and light up your path to a brighter future.

I wonder what my deceased parents would think now of what they taught me so long ago.

Being Hyper Focused as a Trans Girl

2026-05-23T09:54:06.628-04:00

Image from Maxim Tolinisky
on UnSplash.

As I followed my path into transgender womanhood, I found several times that I was too focused on my goal of presenting successfully as a woman when I went out and tried to join the world.

Essentially, what I mean is I was trying too hard to mimic the way ciswomen look and how they move about in the world. I had not yet had the time out in the world to develop the muscle memory I needed to be at my best with others. I so badly did not want to slip back into my old male ways and look like a linebacker in drag in high heels in the mall. In the meantime, I was spending every spare moment I had by myself to try to practice my best feminine walk.

The problem became when I was practicing too much and forgot where I was. Looking feminine in the least at work would not have been good for my macho career. I did the best I could with the time I had to work with just was not enough to create the habits I needed to progress the way I wanted to towards my transfeminine dream. Every time I went out, I would do something wrong and destroy the image of being female that I was trying to portray. If I had my makeup, clothes and hair to a point where I was satisfied, something would come along like catching one of my heels in a sidewalk crack to hurt me. I was very frustrated at the time until I finally began to relax and began to enjoy the new world I so badly wanted to be part of. As I did it though, I was totally surprised at how complex the entire scope of what I wanted to do as a potential successful trans woman would be. My life was like one of those huge “Bloomin Onions” you get at steakhouses. Every time you peel back a layer, you find another layer to surprise you.

As it turned out, at the time I was peeling back more gender layers much quicker than I had ever imagined. I was dodging all the stop signs that I thought I would have and was able to look around my world and enjoy what I saw. Most importantly, I was becoming the me I always wanted or destined to be. Again, I was being blindsided in that I would have to go through yet another transition as my life was coming full circle. I was not becoming someone different at all. I was just becoming me.

The one remaining aspect of my transgender being I did have to remain hyper focused on was when I began in depth communication with other women. I was always paranoid that I would give away too much of my old male past when I was talking with another woman. I worked so hard to be in the world as I was, I did not want to out myself as an intruder. Quickly, I made strides to learn the different way ciswomen communicate that men just don’t understand such as non-verbal cues about danger and happiness. All the way to the power of passive aggression that women use so effectively. To aid in my efforts, I even took feminine vocal lessons to learn key terminology I would need to complete my communication efforts in the world.

As I followed this new direction on my gender path, I did slide back into being hyper focused in my quest to be me. I was intently watching all my new ciswomen friends to see how they lived their lives and how I could fit in. In essence, the new me needed a new place to live and they gave it to me without ever realizing what they were doing because they took their lives behind the feminine gender curtain for granted and I never could. And still don’t to this day since I spent so long trying my best in the dark to get there. I guess I was paying my dues as I learned what my second wife meant when she called me a terrible woman. Back then I was, but I did not want to make that mistake again. So, I became hyper focused on a new goal…earning a spot behind the gender curtain.

My confusion set in because I learned early in life what it took to survive behind the male gender curtain, but I had no clue at all what it would take to survive as a trans woman. Because I knew I would never be able to have such life altering experiences such as carrying and birthing a child such as ciswomen have but on the other hand, I still had a very unique way to my womanhood which still counted. I just had to wait and earn my way back to being me. Furthermore, I did not want to completely throw away everything that I learned for fifty years living in a man’s world. I just wanted to take the building blocks I learned and use them so I would be able to be a quality transfeminine “me” person and never be told again I made a terrible woman. If I was “making” anything from scratch, I wanted it to be presentable to the world.

Once I was able to stop being hyper focused on my early experiences with makeup, hair and appearance, reality in the world set in which meant I would have a chance to live my dream of throwing out or giving away all my male clothes and starting all over again. I hope being a hyper blend of the two main gender binaries helped me along once I finally sensed the true path I wanted to be on.

The ups and downs of life on the journey I took was never easy, but worth it when I made it to the surprise location I was heading for that I never realized. All along, I was just focused on being me.

Letting the Light Into my Trans Closet

2026-05-22T09:58:42.915-04:00

Image from Sahin Kalijii
on UnSplash.

Growing up, I had what I considered to be a very dark and escape proof gender closet.

I was part of the pre-internet/social media generation so I could not find the latest online tutorial on improving my makeup skills. And of course, I could not run to my mom or girls’ peer group for any information either. I was stuck with no light in my closet all by myself it seemed.

I stayed that way for years until gender pioneers such as “Virginia Prince” began to shine her faint light into my closet. I had little to no knowledge that individuals such as me even existed in the world. Once I did, I was very relieved I was not the only transvestite as Virginia called us then in the world and I set out to meet others. Before I could open my closet door even a little, I had to convince my second wife that it would be OK to do it. She had known from the beginning of our relationship that I was a cross-dresser but did not like it when I began to let others know of my so called “hobby.” It actually marked the beginning of me opening my closet door to the world and proclaiming I was a transgender woman, not a part time man putting on a dress and makeup.

Along the way, another problem I had was deciding when to take the chance to open my closet door and to which person. I did myself no favors when for the most part, I tried to internalize all my feminine feelings which made me an impossible person to get along with when I was looking in the mirror at my male self and hating what I saw. All the times I ventured out of my closet only to have to hurry back in was wrecking most of my life as I knew it. Not to mention the life with my wife who I envied because she was a ciswoman, and resented because she would not let me explore a feminine side which was trying to see the light of day.

I found my male self-had installed a powerful spring closer on my closet door which was designed to keep me in. Deep down he knew his part of my life was in danger every time I was able to escape the closet and get out into the world. I felt so enlightened and natural when I did, I never wanted to return to my male life and all its drudgery. I was so sick of wearing the same old collection of ties to work every day when better/brighter fashion choices awaited me in my closet at home.

I discovered that the more I outfitted my closet with brighter lights and bigger mirrors, the more I wanted to test my new fashions, wigs, and makeup in the world. Away from my mirror which had the tendency to lie to me. I can’t tell you how many times the mirror told me I looked great only to be rejected quickly in the public’s eye. It took me years to realize that I was expecting too much on just looking like a ciswoman, I had not yet paid my dues on becoming myself and then having the ability to relax and enjoy myself even more.

It helped me too when I began to venture further away from my closet as my confidence as a transfeminine person began to grow. To get there, I needed to be able to look another woman in the eye and communicate one on one with her about the world around us. Men entered the picture too but briefly since most of them did not want to have anything to do with me anyhow. More and more, I did not have to scramble back to my closet following a bad day or night out into the world because I was doing better in my feminine life. All my male could do was sit back and helplessly watch as his hold on me slipped away and all he ended up being was a provider because of his good job.

I arrived at a point when I needed to expand the small dark transgender closet, I had always lived in. It all began with me having to accept who I really was and had much more to do than just expanding my closet for all the feminine clothes I was buying. I was making a huge lifestyle choice that I had spent way too long deciding to make. All of this moving things around in my life led me all the way to leaving my closet totally behind and looking for a transgender house to live in. I had taken my time (decades) to make my decision, and it occurred to me that I had taken too much time but by then there was nothing I could do about re-winding the clock. I took the good and lived on until I was able to carve out a new transfeminine life.

As I look back, it does not seem possible to me that I have come from the lost, lonely boy staring longingly at himself dressed as a girl in his closet’s mirror to the person I am today. But none of would have been possible had I not been able to embrace the help of several key ciswomen around me to make it happen. I wonder what would have become of me if I was not able to meet them. On the bright side, stepping out of my closet (as scary as it was) enabled me to meet all of them to start with. So, destiny was on my side as my life went full circle from a dark closet to the bright existence I live with my wife Liz now. I was just fortunate as my hunches that everything would work out if I stayed on my gender path. I just had the super strong hunches that they would.

Thanks very much to all of you who read and interact with my writings. All comments are always welcomed!

Staying Calm as a Trans Person

2026-05-21T09:53:00.618-04:00

Image from Matteo Vistocco
on UnSplash.

Many times, during our lives as transgender women and transgender men, staying calm in the face of adversity is not easy.

Perhaps the worst time I had staying calm ever in my life came fairly early on when I encountered a hostile, aggressive woman in a rest room I was simply using to pee. It all happened by accident when I was looking at the door of the women’s room at a venue where I normally had no problems, so I could judge when the room would be empty and safer to use. I had judged correctly, and the room was empty when I entered it and I had my choice of stalls. As I finished the business I came for, I left the stall and started to wash my hands when this woman burst through the door and started calling me a pervert, My first reaction was shock because I had never had any problems before from the staff when I used the woman’s room in that venue. Then, I became angry that this woman who was a total stranger to me was calling me a pervert.

My mind was turning quickly as I fought to stay calm and say something to the angry woman who was completely out of control and fortunately, she gave me the insight to do it. Somehow, in our brief conversation, I got out of her what she did for a living, and she said she owned her own beauty parlor. When she did, I asked her for a card so I could report her business to the very strong and influential LGBTQ organization in town during those days. I never got her card as she turned around and stomped out of the restroom, and I only saw her one more time walking past me in the venue. I glared at her as she refused to even make eye contact with me. So, at that moment staying calm (no matter how hard it was) worked for me.

It is my opinion that the ability to stay calm mainly comes from having confidence in yourself. Normally from years of interaction with the public as your authentic transfeminine self. Like anything else, confidence is very fragile and can be destroyed at any time as you advance up your gender path. You might think you have done the best makeup job ever and was able to find a comfortable outfit which really flattered you, only to find out it did not and you needed to go back home and try again to reset your confidence. There would have been no way early in my life that I could have ever survived the bus tour vacations that my wife Liz took me on where I needed to interact with many different ciswomen on the trip and get along with them in all the restrooms we encountered.

After I enhanced my feminine appearance and attitude with the HRT or gender affirming hormones I was approved for, I discovered a new calmness I had never known before in my life. Which probably came from the hormones themselves, and the fact I was no longer battling being something I just wasn’t. I had achieved all the male accolades and benefits I had ever dreamed of but then did not want them. And I was surprisingly calm when they all went away, never to return again.

Another big surprise was how calm I stayed when I was making more gender transitions in my life into my own form of transgender womanhood. I negotiated all the phases such as being terrified on occasion when I tried out new venues, all the way to when I was making several unexpected transitions, I did not see coming. Even though, I knew what was coming if I was able to survive or even be successful when I went out for the first time at “Fridays” to mingle with ciswomen just getting off of work at a nearby mall, I knew I could never go back to believing I was some sort of a weekend cross-dresser who wore women’s clothes as a hobby. It all was an extreme revelation to me, and I had a very difficult time staying calm through my whole adventure.

On the other hand, staying calm was much more difficult when it came to how fast I was being accepted in my desire to carve out my own transfeminine life. The public was accepting me way too fast and challenged my life and communication skills that I was always putting off. All my procrastination did me no good as the world came crashing in around me and I needed to do things such as feminine vocal lessons to catch up. Thankfully, the world gave me the chance to catch up and again I return to the new calmness I was feeling. These were the days when I was learning almost daily what I would need to do to survive as a trans woman in a sometimes-hostile world. Obviously, I did not want to be called a pervert again for simply wanting to pee. Perhaps I paid my dues, because nothing remotely coming close to that ever happened to me again.

Perhaps also, I am not giving the impact of the HRT hormones enough credit. Even with the minimum dosage I began with, I could feel substantial changes in how I viewed the world. The hormones simply took my male edge off and mellowed me right out like I had always been destined to take them.

Over the years, I have learned to try to separate the always present anxiety I feel about everyday life from the new calmness I have developed over the years. Which in turn has helped my fragile mental health. Which has been quite an accomplishment. Hopefully wherever you live, the anti-transgender pendulum has begun to swing back the other way for you. Even here in Republican led backwards Ohio where I am from, the leading anti-trans bigot in the legislature has his own problems after news surfaced of him being in bed with an underaged girl. Sounds familiar. Right?

Maybe the future is not so dim after all since the world is waking up to the fact that the transgender population is not the problem after all and the rest of the population needs to stay calm around us.

A Special Kind of Crazy

2026-05-20T10:08:37.372-04:00

JJ Hart

In my youth and even later when I was struggling with my deep-seated gender issues, the thought entered my mind that I may just be a little crazy to think that way. I even went as far as telling others I was not the well-adjusted person they thought I was.

Looking back now, I think I was just preparing in my own way to tell others I met that I wanted to be a woman. Which I never did for decades when it became obvious to strangers I met at cross-dressing, transgender socials I went to that I wanted to be feminine, or I would not have been there.

The first time that I told anyone that I liked to wear women’s clothes was after a Halloween party I went to in the Army of all places. Weeks later, over way too much good German beer, the topic came up with friends about how realistic my “costume” was, all the way to my shaved legs. Since I was among a few very close friends, I took a big chance with risking the remainder of the time I had in the Army and told them I was a transvestite (the term used back then) and I liked to dress as a woman. I said nothing about being crazy, and I just liked to do it.

Of course, at that time in my life, I was busy running from the fact of how deep my gender issues went. I was hiding the fact from myself that no I was not crazy, I just wanted to be a transgender woman in the days when the term was first being used. “Running” for me back in those days meant changing jobs and locations frequently to keep my mind off what I was truly running from, my gender issues. Even with all the moves I was making, I could not outrun my life and occasionally the term “crazy” snuck into my thought pattern.

To compensate, I began to do “chores” which I considered feminine in nature such as doing part of the grocery shopping for my wife dressed as a ciswoman. When I succeeded with no problems, I started to feel so natural that I continually wanted to do more. So, I began to combine my grocery shopping adventures with new visits to big shopping stores to pick up small items I could afford such as a pair of panty hose, or new makeup. Amazingly, no one bothered me or shouted, “There is that crazy man in a dress.”

As the years went by, I learned that the ciswomen around me did not think I was crazy. They thought I was more curious than anything else as they wondered why I would leave the men’s club to play in their world. Ironically, as they were taking care of their curiosity, at the same time, I was learning from them. I had always envied girls (then women) so much as I followed them from afar, and now I had the chance to go back behind the gender curtain and learn first hand about the pluses and negatives of a ciswoman’s life and did I want to be a part of it or was I just following a crazy path off a cliff.

I learned quickly that I was following the right path, no matter how crazy it seemed at the time. The more I explored the world as a trans woman, I found the more exploration I needed to do but that was OK with me because again, my life for a change did not feel forced and so natural because I was not fighting to be something I was not…a man. All of a sudden, my life made sense and a was a special kind of crazy, a transfeminine person. At that point, I knew I would have to lose for good all the formidable white male privileges I had earned over the years. Even I was surprised to say “buh-bye” to all privilege I had built up.

Not all benefits I had living as a man were so easy to give up such as part of my intelligence and my personal security. I did not have many interactions with men one on one, but I learned the process of letting the man take the lead in most all situations. Especially when it came to sports, where I knew a lot about what was going on. The other privilege or benefit I needed to give up quickly was when it came to my personal security. I was not prepared for the world I was facing now in which I was fair game for any toxic man. I was fortunate to have escaped injury a couple of times when I broke the rules that ciswomen grow up with such as not finding your self in a compromising position on a dark city street all alone. I thought at the time, I was crazy to do it and never did it again.

Most recently, the craziest thing I have done is to let my precious Estradiol prescription run nearly all the way out. In fact, I am down to my last applications of patches this week as I am waiting for another refill which I have been notified is coming today. I have written in the past a couple of times about the paranoia I felt when I had a recent appointment with my endocrinologist who prescribes my HRT medications. It turned out that that all my crazy paranoia about the far reach of the orange felon in the White House rejecting any ideas of me receiving gender affirming care through the Veterans Administration would ever happen again. Instead, I received a prescription which will last me through another year until our next appointment.

Once again, it was proven that I am a special kind of crazy which I wish I had learned to embrace earlier in life. It would have made life so much richer just knowing I had the chance to experience life on both sides of the binary gender border.

Are We Having Fun Yet?

2026-05-19T10:26:51.105-04:00

Image from Katie Treadway
on UnSplash.

Having fun as a transgender woman or transgender man can be difficult to define. First, let’s define fun as something that provides mirth and amusement. Which comes from “Dictionary.com.”

In my case, I cannot remember finding much “mirth and amusement” when I was cross dressing as much as I could to present as an attractive girl. All I can remember was that I was experiencing deep satisfaction when I thought I had succeeded. As I began to search for a better term, I went back to the “Dictionary.Com” to look up the definition of happy. Because happy is how I felt when I thought I had succeeded into transforming myself into a pretty girl. I was right when the definition of happy was “delighted, pleased or glad” when something was accomplished. It fit me totally because it worked in all aspects of what I was trying to do. Actually, it was all three of the delighted, pleased or glad definitions which fit me exactly.

The problem I was having was getting to the point where I could be happy about trying to cross the gender border. I severely struggled to find the fine line where I could disguise my broad shoulders and narrow hips of my testosterone poisoned body. I certainly was not happy or having any fun when I was brutally laughed at by the way I was trying to present myself as a woman in the world. As I always point out, back then teenaged girls were the biggest test I faced when I went to the malls and they seemed to be attracted to me like magnets, for all the wrong reasons. It took me a while to realize I was trying to dress like teenagers, which brought me completely undo attention. There was no way I could be happy.

What I also did not understand was that fun or being happy was a fleeting thing for me. Sort of what had you have done for me recently, type of thinking which I was very used to from how I was raised. For the most part, I was never allowed to be happy, so I did not miss it at all. I also say for the most part because slowly I began to discover I could feel happy when I was cross-dressing as a man into my true feminine self. When I was able to find the proper clothes, shoes and wigs which helped me with my appearance with my makeup, I could relax and enjoy a new world I had only dreamed of. Fun became to me when I could escape the male world, I was forced to spend so much time in and explore all the new facets of being a confident transfeminine person. It made me happy to discover who I really was destined to be in life.

As I headed past the fun and happy part of discovering myself as a transgender woman, I needed to mention the satisfaction I felt when I had reached the point where my diet had kicked in and I could buy more stylish clothes in my own size for the first time ever in my life. I was ecstatic in my pre-hormonal HRT days when a cross-dresser friend of mine purged his feminine belongings and gifted me a set of silicone breast forms that I needed to run out and size just the right bra for.

Those were the early days of my explorations in Columbus, Ohio when I could attend very diverse by invitation only parties where I could see everyone from lesbians to transgender women considering gender realignment surgeries so I could have a idea of how I might want to live my life in the future. Almost every party I went to was to be a fun learning experience, and I could not wait for the next one. At the same time, I was thinking if I was having this much fun, how could it be wrong to have it.

The only negative I experienced was the night I was cornered in a narrow hallway by a huge admirer of crossdressers and almost learned the hard way about what ciswomen learn at an early age. To not put yourself in compromising positions with men which could possibly overpower you and get yourself into deep trouble. I was lucky that my wife came along to bail me out of the situation I unknowingly put myself into. It was no fun hearing her, I told you so’s all the way home. Mainly because she did not approve of what I was wearing.

As my life progressed towards the ultimate goal of leading a fulltime life as a transgender woman, unfortunately, my wife stood right in my way of progressing. Which meant I needed to cheat on her with another woman which was me. Every time I slipped out of the house in my heels, jeans or boots, I normally had a good time as I was finally having fun as a trans woman and did not want to ever give it up, I had gone too far to ever look back to an old male life I never had a choice on living to start with. Like it or not, my life had put me on a collision course of having to decide what I was going to do about my marriage. The course was disrupted when my wife unexpectedly passed away from a massive heart attack leaving me tragically alone after twenty-five years of marriage.

Most certainly, those days of my life were no fun, and not filled with happiness. On the other hand, they were filled with uncertainty and loneliness until I could find my way home again. Thanks in no small part to my inner feminine self who took over my life and others such as my daughter and future wife Liz. Who helped to pull me from my major pity party. When that happened, life became fun again as I was able to lead a life in the feminine world I always wanted to be part of.

There was Never a Maybe

2026-05-18T09:44:30.165-04:00

Image from Marija Zaric
on UnSplash.

In my life, there were never any maybe moments about having gender issues, only a resounding yes, because I had them.

Time fades the memory, but I think the first inkling of the issues I had was when I began to experience very vivid dreams that I was indeed a pretty girl. That is when I went the only route, I knew how to go and secretly began to raid my mom’s clothing drawers and closets for her clothes I could still squeeze in to at the time. Before I knew it, I had somehow acquired my own “collection” of feminine clothes and makeup I used to practice my new artform. While the boys around me were practicing putting together model cars, I was busy practicing being a girl. At the time, all the practice flustered me, but would come back to help me later in life when I would not have to work so hard on the basics of presenting as a ciswoman.

The more I accomplished in my cross-dressing pursuits, the more I wanted to do because I felt so natural. Which was a huge clue to me that I was on the right gender path, and this part of my life had always been a deep part of me. If I had followed the clues and not ignored them, I would have been much better off in the long run. By putting my deep instincts off, I ended building up a successful but deeply destructive male life. Every time I built something up as a man, I needed to somehow destroy it because I did not want it to interfere with my possible upcoming male to female femininization project. I guess I could say the possibilities intrigued me as much as they terrified me. How would I ever be able to live as a transgender woman dominated most of my everyday life as I envied the lives of the ciswomen around me.

At the time, all of this was happening, all I was trying to do was experiment if my gender dream could ever come true and I could give up all my male privileges I had built up to try it. If I could do it, I could live it became my goal. Which was easier said than done because I was still living most of my life as a transfeminine person only in front of the mirror and not the world where I belonged. At times, making my way from the mirror was a brutal experience for me because the world treated me in ways that I really deserved when I did not dress myself in the proper way to hide the best I could my testosterone poisoned body and attracted undue attention. Not dressing to blend in with the other ciswomen around me was hurting me badly until I finally learned my lesson.

Probably what I suffered from the most was not having the role models I needed to help me in my male to female transition. It was very lonely in the pre-internet days with no social media tutorials to help new struggling trans women or cross dressers along. It was just me and the public to provide feedback on my progress because I discovered the mirror was quite OK with lying to me about how I looked. It would tell me I was attractive, then I would get immediately laughed back home by a group of teen girls was a prime example of what I was going through. I remember vividly the days when I began to seek out the girl’s attention to measure how well I was doing in the world, rather than running from it. I figured if I could succeed in passing my toughest tests anything was possible.

As I began to pass more and more feminine tests, my confidence began to grow, and I started to face my deepest dreams and fears that I could conceivably leave my old male path behind and carve out a life as a transgender woman. On my own in the world. All of this had its good and bad points. The good was that I was finally realizing after all this time I could live my dream and the bad was, what would I do about the remainder of my male life. At that time, I still had a very good marriage to deal with, as well as a family and successful job to consider. It was as if I was painting myself simultaneously into two gender corners which would be hard to get out of. I found wanting the best of both binary gender worlds was impossible to do and coming up soon I would have to decide which way I was going to have to go.

The decision I made turned out to be the easiest one and one I should have made long ago. I certainly had the gender issues I worried about endlessly and would have them as long as I lived. I had always thought that tomorrow would be the day I could figure it all out, but all the tomorrows started to become years and decades and I still hadn’t done anything about it. Gender procrastination at its finest, or its worst. Bottom line was the procrastination I was doing ended up hurting me in ways that I never imagined such as with my mental health which really paid the price of living the pressure of life in two genders. I needed to finish painting the gender corners I had put myself into and do it fast.

On one of the nights, I went out to try to be by myself, I ended up really socializing as a trans woman and enjoying myself. Right then, I decided I had made my final decision to pursue HRT and finally put what was left of my old male self to a permanent rest. It occurred to me then that the decision had always been made for me from those earliest days in the mirror I went through.

All the maybes were in my past. I could succeed as a trans woman, and I had a bright future ahead.

Visiting Andy Warhol as a Trans Woman

2026-05-17T10:06:30.492-04:00

The late Candy Darling.

Years ago, The Ohio State University was hosting a huge exhibition of the work of artist “Andy Warhol”.

Since we knew how trans and LGBTQ friendly Warhol’s work was to the community, a small group of my transgender women friends hopped in my SUV and we headed to nearby Columbus, Ohio to check the exhibition out for ourselves.

The first thing I noticed from my friends was that they were all wearing their high heels which had a strong probability of becoming very uncomfortable if we had to walk long distances. Since I knew the campus a little bit, I knew we would, so I chose more comfortable flats for the walk. I was happy I ended up sacrificing fashion for comfort because we ended up having to park a distance away from where the exhibition was being held.

Of course, we expected no push back at all from us being there to see Warhol’s work and especially because of his connection with trans stars “Candy Darling” and “Holly Woodlawn” who was featured in “Lou Reed’s" famous song, “A Walk on the Wildside” which among other things mentioned shaving legs and he becoming a she. So, we felt no apprehension about going and mixing in with the surprisingly large number of families that were there. Of interest, here was what Warhol said about Darling: “Candy didn't want to be a perfect woman—that would be too simple, and besides it would give her away. What she wanted was to be a woman with all the little problems that a woman has to deal with—runs in her stocking, runny mascara, men that left her. She would even ask to borrow Tampaxes, explaining that she had a terrible emergency.”

For the most part, the group of girls I went with behaved themselves and blended in quite nicely with the crowd of people around us except for there is always one who tries to ruin it for the rest of us. I had the misfortune of being on an escalator immediately behind a trans woman I had barely met when all of a sudden, she grabs both sides of the escalator and spreads her legs up in the air and wide apart. I was in shock that she needed to pull off such a low class move with all the kids and families who were around. I guess she wanted to show off her recent genital realignment surgery to the world, but I let her have it. Saying I wanted no part of her exhibitionism.

Other than that, I enjoyed the exhibition immensely as I was able to learn more about Warhol than I ever would have had a chance to do on my own without the support of my transgender women friends.

All too soon, it was time for us to leave but way too early for us to go home. So, we decided to try out a well-known gay venue in Columbus that we had never been to. The place was packed, mainly with gay men, a group of lesbians, and a group of intoxicated cross dressers who I did not know it then would come back negatively to impact my visit with my friends. Since I was driving, I needed to only have a couple of beers and just in case, needed to use the women’s room before we left on the long trip home. As always, I tried to wait for the best opportunity to use “the room” until I got to the door and it said for use by “real women” only. Which I was later able to find out was because of one of the intoxicated cross dressers breaking all the sacred restroom rules in front of a lesbian when she was in there with him. I guess he did not even sit to pee and urinated all over the toilet seat before leaving without washing his hands. It was no surprise the sign was on the door as the drunk ruined the privilege of using the women’s rest room for all of us.

I was rather naïve that day and had never been around any transfeminine people in my life that could not conduct themselves properly in public. But, like any other group there are always a couple rotten apples that spoil it for the rest. I resent them because it makes it harder for the rest of us to live a so-called normal life.

The trip back home from Columbus to Dayton, Ohio was thankfully uneventful as we talked about everything, we saw at the Andy Warhol art exhibition at Ohio State. About how Warhol was so much more than just a soup can modern artist we had heard of and specifically his dealings and support of Candy Darling and other trans women such as Holly Woodlawn. In fact, there were so many exhibits of his writings and interactive learning also that it was almost too much to take in at one time.

As far as the “Flasher” went, I never saw her again as she lived in a rural area north of where I did and worked at a well-known big box store. I hope she was able to mature and put her exhibition days behind her, and I knew the restroom actions by someone or someone’s in the cross-dresser group were not representative of all CDs everywhere. But there are still repercussions when you cross the gender border into someone else’s sacred space. You must take care not to overextend your welcome.

If you ever have the chance to see and visit a Warhol exhibition, be sure to do it. Maybe you will be like me and come away with more of a respect for his work than I ever had before. He certainly represents another era of life which will probably never be seen again. In fact, there is a huge museum dedicated to the pop icon’s work to visit in Pittsburg Pennsylvania if you are close enough to visit it.

Chance versus Choice as a Trans Girl

2026-05-16T09:58:45.865-04:00

Image from Brooke
Ballentine on UnSplash.

Chance versus choice for a transgender woman or transgender man can cover a wide spectrum of activities.

Chance included all the times in my life when I risked the very future of my male existence to attempt to live in the world as a new cross-dresser or trans woman, before the term was even invented. Choice included all the times I threw caution to the wind and took on the new world I was experiencing anyway. Deep down, I took the chances because I knew sooner or later, it would be the right thing to do and I could live full time as a transfeminine person.

Even still, it was never easy for me to take all the opportunities I had gained from simply practicing the artform of making myself up to be a convincing enough woman that I could blend in with most of the world. I found a large percentage of the population were in their own universe and did not care about mine anyhow. Then there was the number of people who were curious about me and wanted to know more about why I was switching gender clubs from male to female. Finally, there were the hateful bigots I tried to stay away from who for some reason saw me as some sort of threat to them. The more chances I was taking, the easier it became for me to survive.

At this point, to make myself very clear, it literally took me decades to arrive at the point where I had a choice to be myself as I was very slow in deciding if I was making the right decisions in my life. As a parttime cross-dresser, I was basically providing myself with stop-gap measures to relieve myself of the pressures of living a male life I never should be living. I was stuck in the middle with me, and it was not a pleasant place to be. All that got me by were the brief moments of gender euphoria when I was able to navigate the world as a trans woman. But the biggest problem came when I began to experience my own form of impostor syndrome.

I was still enough of a man, operating successfully in a male world to not want to give it up, yet I was becoming enough of my own woman to keep moving forward. It put me in a bad place when I went to invites to girls’ nights out and in the middle of the evening suddenly felt as if I did not belong. In a relatively short period of time, I was able to work my way around the dreaded syndrome and relax and enjoy myself. I had as much of a right to accept the invitation as the next woman at the table as we enjoyed our combined femininity. The entire experience was so different than anything I had experienced at all the men’s parties I had ever been to that I could not wait for the next invitation to come in my direction.

When I was able to overcome my imposter syndrome, I was able to take advantage of having more choices while taking fewer chances. Most of the time, it came from knowing the venues I was going to and knowing ahead of time I would be accepted. Sure, I needed to take chances and choose new non-gay places to go but I desperately wanted to go to venues which reflected my tastes. My wants were simple, I wanted to drink draft beer, watch sports, use the women’s room when I needed to and be left alone. Which I found out that I could in several places, so I had a choice of where I wanted to go. I was living large as a trans woman with choices for the first time in my life.

As chance versus choice began to fade in my life, the choices began to take on extra meaning. I still had what was left of my male life to deal with and he was hanging on for dear life and fighting on to the end. He was tougher to give up because when he went, so did all my old white male privileges out the door with him. No job, no wife and possibly no family awaited my decision on which way I was going to live. Naturally, all the pressure wrecked what was left of my fragile mental health until destiny set in for me and overcame my chance versus choice idea altogether.

In a dark five-year period, I lost all but one of my closest friends to death including my wife who was the major drawback to my male to female gender transition. At the same time, I came out to my only child (daughter) who became my closest ally until my wife Liz came along. Add that to the Veteran’s Administration health care system announcing that they would start the process of administering gender affirming hormones or HRT to veterans who qualified and I did, so I was made an offer I could not refuse and began the process of closing out my male life completely. Destiny could not have made my path any clearer if it tried and I needed to seize the opportunity while I still could. Because I was near the age of sixty at the time. I needed to make my decision to live as a transfeminine person and not look back or forever try to live as the gender juggler I was. Which I could do no longer. I needed to take the right way out and choose the one I should have always chosen.

I think all humans, trans or not face the chance versus choice decisions in their life, but it seems we transgender women and transgender men face more deeper challenges than most others. We risk our jobs, our families, our marriages and even our lives to live our truths, and few emerge from the process unscathed. Best wishes on you making it up your gender path the best you can. There can be brighter days ahead out of your dark, lonely gender closet.

When Every day is Day One

2026-05-15T09:46:04.580-04:00

JJ Hart

We all know how difficult being a transgender woman or transgender man can be. For years, it seems as if you are starting on day one when you are trying to catch up with ciswomen who have lived a feminine existence their entire life.

For me, my journey started when on certain mornings when I did not know if I was going to be a boy (physically) or a girl (mentally) that day. My thoughts often came from vivid dreams I had from the night before that I was living a life as a pretty girl. I just couldn't shake the idea that something was wrong in my life, and I couldn't do much about it except occasionally cross dress in front of the mirror in mom’s clothes and makeup. When I did, early on I needed a lot of help with my makeup and everyday when I tried something new on my face, I was starting all over again. Plus, it did not help that most every time I cross-dressed, it was an adventure in not getting caught. Between my parents and my slightly younger brother, earning my private time to be on my own and be a girl was difficult.

It took me years to shake the idea that every day as a transwoman was still day one in my life. Mainly because, I was still learning so much from all the ciswomen I was around in my new world. I had plenty of stop signs on my gender path I needed to negotiate as I made my way towards my dream of living full-time as a transfeminine person. Some of the stop signs were busy four way stops when I really needed to stop, look both ways, and make the difficult decision to proceed. Looking back now, I don’t know how I managed not to have any major collisions with anyone but my second wife who unfortunately had a front row seat in my transition from just cross-dressing on a part-time basis all the way to considering HRT or gender affirming hormones as a transgender woman.

What kept me going was my deep-seated knowledge that what I was doing was right. All the cross-dressing I was doing was just practice towards a bigger, brighter future as a trans woman. Looking at it that way was certainly difficult, but it was all I could cling to if I was to keep my fragile mental health intact. As my wife told me when we were fighting about my gender that I made a terrible woman. So, I needed to find out what she meant because she added that she was not talking about appearance which I thought I was doing better with.

I set out at that time to re-dedicate myself to understanding a woman’s life. I was naïve at the time and thought I could learn more while I was still presenting as a man fulltime. Years later, when I had crossed the gender border publicly as a trans woman, I finally was invited back behind the gender curtain so I could learn a lot and not be a terrible woman. For most of you who do not know, my wife unexpectedly passed away from a massive heart attack after twenty-five years of marriage to me and she never was able to see the better woman I had become. Mainly because my time behind the curtain enabled me to start all over again and mold the new woman, I wanted to be. Including most of all the nuances and the layers a female must live through before she becomes a woman. My inner female was forced to stay back and be dormant for all those decades before she could claim her ultimate gender prize also. She just had to take a vastly different path to get there.

At that point in my life, everyday was day one again when I donated all my male clothes and vowed to never look back again at my male life. Which I ultimately found impossible to do. Male influences built me into the person I had become as a transgender woman and made me stronger in the process. I even brought experiences from the most male dominated part of my life to my gender table as I remembered the days I went through in Army basic training. There was no need to throw away valuable experience I could use in my new life.

It turned out to be the most exciting time of my life when I could finally live my truth in the world. And I was able to forget the dark days of my youth when I began to deeply question what gender I was. Having all the help I did to finally begin to fill out my gender workbook helped me too, even though I was rejected on occasion and needed to start all over again. I urge all of you who are considering a journey in life the way I did, is to be resilient and expect many ups and downs along the way. Most are just learning experiences anyway and can be valuable as you are allowed to play in the girls’ (or boys for you trans guys) sandbox. It takes time and experience for your confidence to grow as you navigate one of the most difficult paths a human being can take.

Slowly but surely, every day will not feel like day one as you get used to living a full-time life you have always dreamed of in a gender world you want to be a part of. For me, it was like taking a great deep breath of fresh air when I was finally checked out and was able to begin the long-awaited HRT which would transform my body outwardly and more intensely, inwardly. My entire being was telling me what took me so long when the male to female feminizing hormones hit my system. But I did not need the hormones to tell me who I was, they were like the icing on my transgender cake and made every day a better day.