Sunday, August 2, 2026

Violating Gender Boundaries

 

JJ Hart. Pushing my gender\
boundaries. 

Very early in life I learned that violating gender boundaries could result in severe trouble.

It was obvious to me that the male dominated family I was born into would ever accept a son who wanted to be a daughter. So, I had no choice but to turn inward with my developing feminine senses in the male world I was trying to be a part of. I was born way too early to take advantage of the forthcoming online information world with the advent of computers and social media. Again, I was trapped into trying to cross-dress my feelings away anytime I had the chance.

The other main problem I had was that the gender boundaries were so rigid and demanding I could not see any way out of my dark, lonely gender closet. I lived in a rural area with mostly boys and no girls to have a point of reference from. I only remember one occasion when the only girl in the neighborhood was persuaded by a couple of the boys to show her naked genitals to the group, and I was not excited but embarrassed for her at the time. Just another example of how my sexuality was developing away from the “normal” male’s. I had no need to see her private parts and wondered why I was so different. Little did I know, it was just the beginning of challenging my gender boundaries during my life.

As far as the rest of my life went, I wasn’t much of a challenger of anything. It wasn’t until I reached my college years and was drafted into the military during the Vietnam War, did I begin to challenge the system. At the same time, I was starting to challenge the war and the politics around it, I was pushing my cross-dressing boundaries by starting to leave my house more dressed as the person I wanted to see if I could become. I even made what turned out to be a huge mistake by coming out to my fiancĂ© as a transvestite or cross-dresser back in those days. I say huge mistake because she wanted me to tell the draft board I was gay to stay out of the military service. Even then, I knew a lot about myself and did not have to push my gender boundaries so far to lie and tell someone I was gay. As a side note, then and now I did not have anything against the gay community, but I just knew there was a real difference between them and me.

Of course, the military stopped any gender challenging I was thinking of doing dead in its tracks for nearly three years of my young life. The only challenge I could do was mental in nature as I imagined how life could be better for me as a transfeminine person when I was discharged from the Army. Even then, I was restricted in my gender thinking to the reality in life. What I almost did was send a letter (remember them?) to my future first wife explaining it maybe a transwoman picking her up at the airport when she arrived for the first time. She was in the Army too and was discharged about nine months after I was.

Little did I know, if I had decided to test my gender boundaries then it may have been one of the better times to do it because I did not have the chance to build up all the troublesome male baggage I would acquire later in life. On the plus side, I had a very new car that I had shipped home from Germany, my stereo equipment and a sizeable bank account to start a new life with. On the negative side, I thought I had a good chance of losing my family, friends and job if I started all over as a woman.

Long story short, I did not have the courage to push my gender boundaries any further than they were at the time. Except for a few Halloween adventures, and the occasional night out, my life as a trans woman was mundane. It was not until I could not take it any longer the annual yearly adventures at Halloween, did I start to really push my luck by going out more often. My early explorations were rough to say the least until I settled down and learn how to blend in with the ciswomen who I found really ran the world I wanted to be a part of.

As the world let me in as a transgender woman and/or I finally learned the truth of who I was, I kicked and pushed until my gender boundaries came down. It was like the steep slope I write about as I slid down trying my best to hold on to what was left of my old male life but failing miserably. As I continued to gain my new feminine ground behind the gender curtain, which was hidden from me for so long, I had pushed by gender boundary so far, I was too far gone. I was no longer afraid of the fall and knew I was too far gone to ever go back to being my old male self.

From then on, gender boundaries did not mean much to me except from my former history as a man, I could see both sides of the border from where I lived as a trans woman. Leaving the man’s club scared almost all of the cismen away but attracted as many of the ciswomen that I needed to set up a new boundary. The new boundary was one which validated myself as a woman for the first time in my life and it seemed I was learning daily how to adjust to my new situation.

From that point forward, I changed my legal name and became extra serious about my physical and mental well being by being approved for HRT or gender affirming hormones. It just seemed by that time, I was just doing what came natural in solidifying my new gender boundaries. Sure, they were all big moves in my life, but good ones that I had always dreamed of making.

As always. Thanks to all of you who read along with my lifetime worth of experiences. Your responses and comments make it so worthwhile for me!

 

 

 

 

Saturday, August 1, 2026

Living the Dream

 

Image from Randy Tarampi
on UnSplash.

I discovered before I could live a dream of living as my own unique sense of womanhood, I needed to discover exactly what that meant.

I knew very early on it was much more than just applying makeup and parading around in one of mom’s dresses. It went much deeper than that. I wanted to be a girl as badly as anything I had ever wanted in my life.

The problem was that I was stuck in an information “never-never” land with no internet or social media of any sort to provide key information on what it really meant to have issues with your gender and not just throw you aside with some sort of a mental illness diagnosis. I did know enough about myself to know I was not mentally ill for wanting to be everything feminine. So, I did the only thing I knew how, day dream my life away envying the ciswomen around me.

As I grew into myself, I learned more about my dream and the overall demands it would make upon my life. Even though I tried not too, I still added extra male baggage such as a child, marriage and a better career to my life. I always thought I would be better off lonely with just having myself to depend on if I ever had to get rid of it all in my male world and start all over again as a transgender woman. Another problem was that I was tantalizing close to encountering other gender conflicted people who were actively following their dreams, so I knew it was possible.

For example, I just missed crossing paths in my broadcasting career with other trans women who were actively following their dream. One at a small radio station I worked at in my hometown and another I ran into at a AFTN Thailand radio/tv reunion in New Orleans. Sadly, the trans woman was so shy and backwards, I could not even get her attention to say hello.

Everything changed when I came home to nearby Columbus, Ohio and was invited to very diverse small parties on a regular basis. Everyone was there, including several trans women who were headed for gender realignment surgeries that I was able to interact with and learn from. How much exactly did my dream entail? Going all the way like they did, or not was my major point of wanting to know about them. The one thing I did find out was that they had taken the time and effort to set themselves up for success in the new lives they were undertaking. One trans woman was a firefighter getting ready to retire and had a good pension and insurance coming to cover her surgery and another was a very successful electrical engineer who was extraordinarily beautiful and knew she would not have any problems continuing to work after the surgeries.

I was in neither of their classes in appearance, insurance coverage or job security to even compare myself to them, but still my dream of ever living as a transfeminine person would not go away.

Somehow, I needed to carve out my own individual gender path to success if I was ever going to make it. Finally, I learned the powerful message to just be myself and most of the rest of my problems in my male to female femininization would fade into the background. No, I was not extra attractive such as thedestiny transitioning transgender women that I knew but I realized that many of the ciswomen that I knew weren’t either. It was very shallow of me to think that all that went into to being a quality person as a woman was just appearance, so I grew past it. My focus shifted into having more confidence in myself as a good person that a stranger would like and away from just how I looked. When I did, my dream began to become a better focus. Maybe I could do it after all.

Of course, my major focus was what was I going to do with all the unwanted male baggage (and some of the wanted too) that I was planning on taking along on to my new life. At that point in time, my second wife was still alive, and she had made it a point to tell me she would never want to live with another woman, so I had to figure out what I was going to do about that major problem. Then I also had the usual conflicts we all face such as what we are going to do about employment and would any of our friends accept us.

For me, destiny came along and in one fall swoop showed me the way to living my dream. My wife passed away. Leaving me alone to consider my future about the time what was left of my close male friends died too. It turned out destiny was giving me a clean life slate to work from when I began to start all over. In addition, I was old enough to retire and work a little on the side to make ends meet and the Veterans Administration health care system which I was already a part of decided to approve gender related care or HRT for qualified veterans which I was. Destiny could not have shown me a better path to my dream than if I had planned it that way. I needed to pay my dues and work through many dark, lonely days to get to the light, but it was worth it when I did.

Finally, my dream became a focus for me when I met my future wife Liz and other ciswomen who let me into their world. I was able again to focus my dream on reality and make sure it was not a nightmare. Perhaps the best part of the entire trip up my gender path was the likelihood that I would ever make it. To say the least, my going forward was a shaky proposition to start with and all too often, my mental gender darkness threatened to catch up to me and my dream.

Thank goodness it never did, and my transgender dream became a reality.

Reality for me is also to have you join in with my thoughts. Thanks so much for doing so!

 

 

 

 

Friday, July 31, 2026

When There is No One to Believe in You

 

JJ Hart

Sadly, transgender women and transgender men spend much of their lives being lonely with no one left to believe in them.

When it happens, the dark lonely closet you have been dealing with becomes even more restrictive and uncertain. With me, the only thing that kept me focused on my gender path was a little voice which kept telling me that against all odds, I was doing the right thing.

Maybe, like some of you, I had the same misgivings of what I was doing as I cross-dressed as a girl. Was I going through a phase, a fetish or was something wrong with me mentally all entered my mind one time or another. I did know, I had very few male friends and for some reason felt uncertain around the ones I did meet. Which only added to my loneliness and made me withdraw further within myself. It was very difficult for me to believe anything about myself during this portion of my life. But I thought I had no choice but to struggle on.

It was not until much later that I found that I did not have to struggle as much as I was doing as ironically, both sides of my dual gendered personality were coming out of their shells slowly at the same time. After military service in the Army, I learned to not be afraid of other competition from men, while at the same time I was learning how to exist in a ciswoman’s world I had always dreamed of. Life as I knew it was becoming unbelievably complex as I tried to balance two genders mentally and physically.  Every day, I needed to concentrate on who I was going to be when I faced the public. Ironically, I needed more room in my closet to make room for marriages, kids and employment.

Even when all of this was going on, I still felt lonely and wondered what I was doing wrong with my life. The problem was I was living backwards, which I would not understand until much later in my life sadly. The basics did not come to me that I was not a man trying to be a woman but was a woman trying not to be a man. It all comes under the old saying “If I had known then, what I know now, what a better life I would have had.” But the fact remained I was still living a very shallow life as a novice transgender woman and had so much to learn before I could claim my own version of womanhood.

For the longest time, I just took for granted I would just be lonely as a part of life I would have to get used to. Especially after my second wife of twenty-five years unexpectedly passed away from a massive heart attack. Even though she did not accept me as a trans woman, somehow, we still did stay together until the end. At least, I loved her deeply and was never lonely with her, or so I thought.

I found you do not miss what you had until it is gone, and death is the ultimate version of being gone and starting all over for me at the age of fifty-five was not going to be easy. Even though the relationships I had built up as a man were very few, what I had were all starting to die also. Any relationships with ciswomen as a man that I had were few and far between because I was not sure which direction I would go with my gender. I did not want to start another relationship with a woman just to end it by telling her she was actually living with another woman. As the gays would say, I was keeping my true self on the “downlow” the best that I could.

What happened next was that I was increasingly having a difficult time staying on the “downlow” because of all the explorations I was doing in the straight world I was trying to re-enter. This time as a transfeminine person. I was slowly building social relationships in the world with ciswomen who suddenly showed an interest in me. The problem I had was I was still not on HRT yet and was still in my mind too fake to pursue a relationship with a woman when after I stripped down to my basics, I was still a man without my fake hair, breasts and hips. Even with all the social stimulus I was receiving in my new world, I was still frustrated and feeling alone in my life.

I finally realized that I was the only one holding myself back from learning if I could be approved for gender affirming hormones or HRT.  I made the medical appointment from a doctor’s ad I had seen in a local LGBTQ publication and before I knew it, I was deemed healthy enough to be approved. It was a major step in my life and one I did not take lightly. The first night I took the minimum dosage of estradiol and spiro pills I was prescribed, I saved the special occasion for when my future wife Liz could join me in a venue in Dayton, Ohio.

Very soon, my HRT dosage was increased, and I ended up calling them my “magic pills” before I was switched to patches which would be easier on my system. Thanks to Liz and a few other ciswomen friends, I was able to think about forming deeper relationships with women again. My body had morphed into a curious gender blend of breasts, hips, soft skin with a non-performing male piece of equipment which did not seem to matter to the ciswomen around me who were not as insecure with their sexuality as most of the cismen that I knew.

Most importantly, I gained the confidence to believe in myself, which led me to not suffer the extreme loneliness I had felt during many parts of my life. It was like I was on a wheel, and my life had had the time and good fortune to come around again.

Hey all!!!! Thanks for reading.  Your input makes it all worthwhile to me.

 

 

 

Thursday, July 30, 2026

How Much Courage did it Take You?

 

Image from Jon Tyson
on UnSplash.

Often, I hear the words courage or bravery kicked around when it came to mentioning someone coming out of their closet into the real world.

In my case, I would have to replace either of the words with just being afraid of what would happen if I did not pursue my gender dreams of living as a transgender woman. Mainly because I was so self-destructive when it came to causing self-harm to my unwanted male self. I drove too fast and recklessly, drank way too much and even tried to actively kill myself once because of my gender dysphoria.

Especially after I had the rare chance to talk to my friends who survived brutal combat in the Vietnam War, I reserved the terms brave and courage for them. Because in many ways, I was just doing what came naturally when I cross-dressed in front of the mirror at home. It turned out staying in my own little feminine world was very easy until I began to want to see if I could stretch my luck and actually leave the house looking as close as I thought I could to a pretty girl. The only reality I did know was I was scared to death.

Little by little, my fear began to subside, and I wanted to expand my explorations to bigger and better venues such as the malls which were just beginning to come into their own back in those days. Still. I didn’t think I was brave enough to do it. Or was I just being stupid by risking losing everything that I worked so hard to build up in my male life. My ego dictated that I did not dwell on the stupid aspect of trying to femininize my testosterone poisoned body. I just wanted to blend in with the rest of the ciswomen I envied so much. As much as I was being abused by certain segments of the public, I began to use another term to describe myself and that was stubborn. In fact, I think that would be a great title to a new PBS show (Public Broadcasting System) called the “Stubborn Cross-dresser.”

As I continued on my gender path towards finally being allowed to join the girls’ club, my stubbornness in trying new things was both a blessing and a curse. A prime example was when I was trying to hang on to my teen fashion sense way too long. It was a curse, and my blessing came along when I became stubborn enough to keep going back to my cross-dressing drawing board until I fixed the problem and became able to blend in better with the women, I wanted to notice me. After the death of my second wife of twenty-five years, I was desperately lonely and did not want to attempt to build another life as a man when the possibility of building one as a trans woman was right in front of me. If I was brave enough to take advantage of a life I had only dreamed of. Was I going to take the easy way out and try to be a man again or build upon what I had learned as a novice transgender woman became my major question to answer.

Finally, I needed to “man-up” and be a woman as my second wife used to tell me and when I had the courage to do it, I felt a deep happiness in life I never had before. In fact the feminine privilege I found to be the most pleasant was the fact that I was allowed the opportunity to be happy. For the first time in my life, I was able to align my sun, moon, and stars so I did not have to fight a gender battle on two fronts which kept me unhappy and on edge. I positively loved my new life along with my first chance ever to just be happy with what I had.

If you are one of the many gender conflicted individuals trying to decide if and when you will make the ultimate choice to go for the gender border as a trans woman or trans man, my only advice must be, look deeply inside yourself for your answer. Your answer is there If you are stubborn enough to find it. Life is like an old merry-go-round and often it is difficult to slow it down to see the real world spinning in front of you. And if destiny puts you on the right path to do it, you can discover a group of well-meaning friends (ciswomen or men for you trans men) who can help you along. Making you a better person than you ever thought you could be. I would never have thought that the gender dysphoria that I felt would end up causing me so many problems in my life.

Before your life ends and you move on to whatever other place of existence you believe in, you have the basic right to be happy. You can deal in semantics and call your gender journey as being brave or having courage all you want but the end result is you being the natural person who you always should have been.

Somehow, we have been chosen to lead a different life’s journey than most of the others in the human race. Call us brave or courageous if you want but as a tribe, we are doing what we were always been destined to do. It is just too bad we are met with such resistance by haters in the world. As well as the gatekeepers who want to keep us away from our chosen genders. When I speak about gatekeepers, immediately radical feminist TERFs come to mind who have no business in ours.

Best wishes on your successful gender journey and summoning enough courage (if you want to call it that) to get out into the world and live your best life.

Thanks again to all of you who join me in my experiences, and I hope we can all learn from them. I apologize to all of you who have commented. I am a little behind getting back to you because of technical problems.

 

 

 

 

 

Wednesday, July 29, 2026

Why Me???

Image from Barbara Burgess
on UnSplash. 


I have often thought during my life as I was becoming aware of who I really was as a transgender woman, why me?

Those were the days of thinking I was the only male in the world who wanted to be female, and if I was, what was I ever going to do about it. Very early on before I had the necessities to start exploring the world on my own, I needed to rely on just the occasional cross-dressing experience in front of the family’s hallway mirror. It was very difficult to do because I needed to work around a very curious brother and family.

Most certainly, for years, I played the victim as I felt sorry for myself and my gender issues. It wasn’t until I began to leave my dark, restrictive gender closet did I begin to see that I was not so much of a victim after all. Overcoming my gender dysphoria would make me a unique human being with my insight into both genders. But only if I first paid my extensive dues to get there.

As most of you know, the dues transgender women and transgender men pay to challenge and win the battle to change genders is extensive and often dearly expensive as we have to give up spouses, family, friends and jobs. Just for what some see as a selfish pursuit of personal pleasure. If they ever knew the truth, most certainly they would not feel that way as they never had to feel the anguish, we feel about hurting others. During the depth of my struggle, I was down mentally and lonely as I felt why was this all happening to me. It led me to feel selfish and there was nothing I could do about it. I was even jealous of the other cismen around me who could follow their so-called “normal” lives without worrying about something as major as wanting to be a woman.

As I continued to learn what it would take to lead a transfeminine life, the more I respected what I had discovered and wanted to learn more. That was the time I began to see the light of my victim tunnel was not the train but was sunlight which would lead me into a new day. Away from many of the old fears and paranoias about going along my continuing male to female femininization path I was traveling. Slowly I discovered there could be much more to my gender journey than just doing my best to blend in with the ciswomen in the world around me. I still did not know why me, but at least I was not a victim any longer and I just might be on to something much bigger if I could escape all my self-destructive behavior I was engaging in.

I learned the hard way from pure social experimentations that I was on the right path and to keep going. Maybe by doing so, I could climb the gender ladder up to the level of where some of my transgender mentors were. If they could make it, why couldn’t I. It wasn’t why me anymore, it was becoming why not.

I was more certain in my gender choices when questions surrounding things like my sexuality came about. Because I was immediately embraced by so many ciswomen so quickly, I never had to worry about the occasional man that came along and mainly viewed me as a fetish object The last thing I needed was having to deal with the drama of a toxic cisman. So, I never did as I was able to discover my validation as a transgender woman through other strong women. Why me became suddenly very real as I kept going out night after night with the group of mainly lesbian women who accepted me. They taught me more than they ever knew about what it was like to survive in a world where men were basically an afterthought.

In their own way, my lesbian friends helped me to be prouder of the trans person I had become. My why me became why not as I grew increasingly confident in my own skin as a transgender woman. To coin a classic song, I could see the world from both sides now and be part of a special group of humans that could. Which is why I think so many transphobes and TERF feminist gatekeepers fear us and try to keep us out of women only spaces. Like them we gained our womanhood, just from a different and unique vantage point and we are not men trying to slip in. Especially since we work so hard to get away from the male culture.

Long ago, I was able to put my why me victim mentality about being transgender behind me and get on with my life. It marked the turning point when I could be accepted into the only club I ever dreamed of being in…the girls ‘club and I never have regretted doing it. Following several not so good decisions in my life, I finally made the right one and put the necessary work in to earn the title of proud transgender woman.

Today I will put my public gender persona to the test again as I go with my wife Liz to two of her doctor’s appointments. It is usually the easiest test of all because all the people I run into are mostly concerned about themselves. Plus, these days, I normally mentally have gone back to thinking my newer transgender self has been me all along. No more victim mentality. I always point out I did not have much to work with when I started my journey except a deep will to do it. I also wonder, if I knew all the bumps and bruises, I would have along the way, would I ever attempt the trip across the gender border. It took me taking the chances to get out into the public to make it at all, and if I did not, I probably would have been in my closet crying, why me.

For the first time in my life, all I knew was I needed to get out of my closet and fight for the life I really wanted.

 

 

Tuesday, July 28, 2026

Who Got in Your Way

 

Image from UnSplash. 

Perhaps there was that special person or persons who stood in the way of you going along your formative gender path. In my case, I always tried to blame my second wife for being in my way of perfecting my male to female feminization project. My first wife was not a factor because I thought she was just along for the ride, no matter how bumpy it became and I always thought I could suddenly tell her I would be gone for several months because I was going to Thailand not to visit but for gender realignment surgery and she would say be safe.

That was all well and good until I met my second wife who I immediately fell in love with. I ended up divorcing my first wife and marrying my second in a fairly short time. Like my first wife, even though she knew I was a parttime cross-dresser when we married it was fine with her but unlike wife number one, she always resisted me going any further towards maturing into a transgender woman. Being as strong-willed as she was, I wonder how we made it through twenty-five years of marriage until she passed away.

Throughout the years, we somehow stayed committed to each other following many bitter battles over how I was wanting to live my life. She was much wiser than me over the years as she told me things such as I made a terrible woman (true at the time) and why didn’t I just go ahead and move away and live like a woman and save both of us the hassle. As I always point out, I did not know how to “make” a better woman because I had never been behind the feminine gender curtain to discover all the complexities of what I was taking on. As far as just going away and starting all over on my own, I was selfish or self-centered and wanted to maintain as much as I could of my male life which among other things paid most of the bills.

Through it all, faint glimpses of my transgender dream kept filtering into my life, and I did things like transvestite-transgender mixers and Halloween parties to experiment if I could make it at all. Once I received positive feedback from doing it, I was pushed forward to expand the boundaries of my marriage. Just to be met with an equal amount of pushback from my wife. The worst part about it was I understood where she was coming from as her marriage was unraveling right in front of her eyes at the hands of another woman. Who was me. I ended up resenting her in a couple of ways. First, because she was what I always wanted to be. Soft curvy body and all. And second because she stood directly in my path of achieving the same things that she took for granted, along with the rest of her ciswomen friends. Great makeup, hair and clothes could not hide the envy I felt for missing out on a feminine life I always wanted.

It took me awhile after she passed on at the age of fifty to realize who the real culprit was who was standing in my way of my male to female transition. All along it was all me who never responded the right way when my wife said be man enough to be a woman. As I said, I was too selfish to not want to give up all the male privileges I had earned over the years and wanted to live my life on dual gender impossible terms as long as I could.

I also tried therapy on the side to help the way I felt and even rejected their advice when essentially, they told me the same thing my wife told me. There was nothing they could do about me wanting to be a woman. She was a part of my inner self and only I could deal with her. When it came right down to it, I was scared of my inner woman and how she could ever carve out her own life in the world. It turned out, I just never gave her enough credit as over the years with help from strong feminine role models like my mom and wife, she was able to mold her own personality. Even though she had to keep it hidden for decades. Those same strong ciswomen showed her where there was a will, there was a way. Especially when you had to take the time and effort to get there.

Once I found myself firmly placed behind the gender curtain, the real work began to make sure I never “made” a terrible woman. I wanted to as much as possible, bring all the good feminine characteristics with me so I could do more than survive. I wanted to thrive as I made my way to my dream of living a transgender life. As I did, the major realization came to me that it was me and only me who was standing in my own way all those years when I was wondering what gender I was at all. Shame on me for not having the courage to face my true self in the mirror and not let my gender dysphoria get in the way. Worse yet, everything was screaming within me that I was doing the right thing when I approached my transgender womanhood. Freeing myself up to live was as if I was taking a ton of weight off of my shoulders.

Ironically, once I was approved to play in the girls’ club, the difference I had from the different upbringing I had made me a special sort of woman to the ciswomen who accepted me around me. Even though they knew I came with different baggage, the most radical advice I ever got was welcome to our world when I was complaining about hot flashes. As my body started to respond to the HRT or gender affirming hormones I was on that I had waited so long for. I don’t think the women ever realized how badly I wanted to be in their world.

If it was not for me being in my own way, I would have been in their world sooner. My proper place to be.

 

Monday, July 27, 2026

Staying in the Present as a Trans Woman

JJ Hart at Trans Ohio.
Staying in the present has always been a difficult task for me. Perhaps it all started when I was a very young gender distracted person and could not seem to stop daydreaming about being a pretty girl. The daydreams were nearly always a great escape from my everyday boring male world where I was always competing for the same rights to be recognized at all.

Overtime, I was rarely successful as a boy and just put in the amount of effort to get by. The only thing I was moderately successful on was hustling on my newspaper route and doing extra chores around the house to make extra money. Which in turn, I used to buy my own feminine articles such as makeup, and pantyhose for when I was able to shave my legs. Overall, my plan worked and eventually I was able to build up my own collection of cross-dressing essentials. As I discovered I could get away with shopping at a couple of small local department stores for everything I needed to shatter my dream of doing it and stepping into my own form of reality.

The older I got, the more I did not grow out of my cross-dressing gender desires. In fact, I grew into them when the world became more and more accessible to me. I was building an increasing sense of confidence in my new self and going out briefly into the world as a novice when the Vietnam War and the persistent military draft caught up with me. For the first time in my life, I could not daydream of something as major as a war going away. It was as real as my draft card. Which I resented having because none of the ciswomen around me needed one. Why should I be forced into an unfair war when they were not was what fueled my resentment. A resentment which just made me feel worse as I wasted my time worrying about the war which was staring at me in the face.

To make matters even worse was the fact my fiancé who knew I was a cross-dresser told me we would break up unless I told the draft board I was gay. Which, there was no way that was going to happen, so we did end our relationship just before I headed out to Ft. Knox, Kentucky for Army basic infantry training. Even though I fought military service as long as I could, in many ways it did me good because I needed to stay in the present most of the time when I was going through basic. If I was not, I would feel the wrath of the drill sergeants which was not a place I wanted to be. I guess you could say, I was going through a whole different basic training by teaching me to stay in the present.

After I had served my time, I tried my best to pick up where I left off by trying to join the world as a transgender woman. A new life was just starting to come to me with the realization I was much more than a part-time cross-dresser and needed to experience more of a woman’s life to satisfy me. Change was upon me with the birth of my daughter and a new wonderful world of mall shopping experiences to explore. After a rough start, I was able to present well enough to enjoy being out in the world. In other words, the teenaged girls who made me a target suddenly left me alone. The rest of the mall time was easy because I discovered that my money was green and that was more important to the store clerks who waited on me than my potential gender.

Eventually, more reality than daydreaming set in with my life. I was becoming so successful in carving out a new transfeminine life I knew that I had gone too far to ever turn around on my gender path to ever go back. Sure, I was scared but a voice in the back of my head kept telling me this was so natural that my new world deserved to be the reality I always sought and I needed to stay in the present to do it.

I discovered as a transgender woman, the present was a very great place to be. For once, I had access to the gender I wanted to be with which were all the ciswomen who showed interest in what I was trying to do in their world. I had always had a difficult time making friends with other men when I was acting like one and I finally figured out why…I should not have been in the boys’ club to begin with. Living a lie was a total mistake which should never have happened. I was not interested in a club where I never belonged, and that was OK.

Old habits are hard to break, and maybe even more so for transgender women and transgender men. Primarily because we have to decide what baggage we are taking with us or leaving behind as we journey along our gender journey paths. Bring too much, and you can’t carry it all or don’t bring enough and end up losing all of your building blocks you need for a new life are all things to consider. And most of all, it is important you stay in the present, so you don’t forget where and who you are and slide back into your old self. It is frustrating when something as small as the look on your face can destroy all that you have worked so hard to perfect. That old male “stay away” scowl may have worked in your old world but in your present one, it certainly doesn’t.

It was difficult for me to find my present. Determine if it was the right choice and then stick with it. As I went through my male to female feminization efforts, I needed to finally decide on a wig to wear on a regular basis and quit looking for the miracle wig which would instantly make me attractive. Why? Because people were starting to recognize me as a person, and I needed to build on that. Instead of just carving a new person, I was blasting one and having the time of my life doing it.

I just wish I could have stayed in the present earlier in my life, which I know would have given a better understanding of who I was at the time. I almost did more after I served my time in the Army, but it was in the mid 1970’s and the world was different, and I did not have the courage to do it. Instead, I played my status-quo cards and thought I could help my life along by just cross-dressing. By doing so, I just ended up losing so much of my life when I ignored living in the present. One way or another, it is much too late to cry over time that was wasted and remember the good time when I discovered my present and lived it.

Thanks for reading along with me. Hopefully my insights can help you with yours and comments are appreciated.

 

 

 

 

  


Sunday, July 26, 2026

Gender Affirmation Day

 

Image from Ava Sol
on UnSplash.

Recently, I had a rare opportunity to meet and enjoy the company of a small group of family for breakfast which I like to call a gender affirmation day.

Precisely, there were four of us including my daughter, son-in-law, my wife Liz and myself. For the morning, I chose a breakfast only small chain venue which we had never been able to go to before. Since it has been a while since I have seen daughter and son-in-law, I was very happy to see them. In addition, I have three grandchildren who did not come since they are adults now and have their own lives to attend too. Plus, the oldest, is a nuclear engineer and lives in Maine and the next two in age (both boys) are traveling in Japan. The youngest is some sort of a bio-engineering student at “The Ohio State University.”

Getting back to my experience, I was dressed very casual in my favorite jeans, new OSU T-shirt and comfortable tennis shoes to face the world at large in a place I had never been to at all. Plus, I did put on some light makeup and partially tied back my increasingly long hair. We were lucky enough to beat the Saturday morning breakfast rush and got a seat as the place was filling up. As I always do, I try to find out if anyone is paying any extra attention to me as Liz and I made our way to our seats. Nobody did except this pesky kid (boy) who would not stop staring at me after we sat down close to where he was sitting. Through it all, I managed to ignore him until his family finished eating and left before we did. Leaving me to completely concentrate on my food and the pleasant conversation that was going on.

As I always point out, being transgender in my daughter’s extended family is not much of an anomaly after all. The nuclear engineer in Maine is trans and my first wife (who is my daughter’s mother) has a transgender man cousin. Diversity runs in the family, whether the naysayers, which are a few, like it or not. My first wife’s in-laws are very redneck conservatives, the same as my ex-communicated brother’s. So, I have not talked to him in over a decade.

My daughter was and is one of my strongest allies and used me as an example to all three of her kids on diversity in the family. She has always been by myside during my male to female feminization journey and I love her deeply for that and how she turned my out-of-control life around when she was born. As a point of reference, she will be fifty years this year and I am trying desperately to come up with something special to do for her but she I like most all of the other ciswomen in my life, they do not have a grasp on what they did for me.

Since now, I spend so much of my time isolated from the real world and because I have mobility issues, I don’t have a chance to match wits with the public anymore and face people such as the pesky kid who would not quit staring at me. It is a good thing he was not sitting at an angle where Liz or my daughter could see him or there could have been some sort of an altercation about having manners. That would have been bad because I am used to fighting my own rare battles. As most kids do, he got bored and turned his attention back to his breakfast. Per norm, is mom was too busy on her phone to be paying any attention to her kids and at least they were not screaming.

Since my daughter’s world is so busy with work and acting as a home care person for her mom, it is difficult for us to put together the time to get together, and I can take advantage of a powerful shot of gender affirmation. Because I can still benefit from it so much and I have always been just me to her and the rest of her extended family no matter what gender I was living as. As a matter of fact, it took me longer to adjust to them accepting the authentic me than them to me. One of the reasons was because the pressure of living an unwanted life was over and I was free to be happy. They knew me better than I knew myself.

More than likely, I won’t have to wait as long as I did this time for another shot of gender affirmation from person who went through my transition with me because my daughter has access to many old pictures of my family I need for my book I am writing for them about my life. She lives in Dayton, Ohio about an hour away from where I live in Cincinnati so it’s not like we live right around the corner from each other. Plus, her big birthday is coming up on Labor Day, so perhaps we can pick up the photos then and if her mother-in-law throws a big party, there will be more gender affirmation for me to selfishly enjoy. Maybe my second wife was right, my gender struggles were all about me.

In many ways, gender affirmation is just another term for having an extended period of gender euphoria. It is just another way of saying that I need to be relieved of my transgender insecurities because they run so deep. Maybe it is because I was forced into that male box, I wanted no part of for so long yet eventually learned to master in so many ways. Or me just wanting to be a transfeminine person was so difficult for me to accomplish, I could never forget the struggle and still bear the scars from him fighting me for control.

Regardless of my insecurities, I still try to keep them hidden around my supporters and do my best to show my appreciation for the gender affirmation they have given me.

 

 

 

Friday, July 24, 2026

It's All in the Details of Gender

 

Image from Liam Nguyen 
on UnSplash.



Quite early in life, I learned to pay attention to the details when I followed my instincts and started to cross-dress into mom’s clothes and try to put on her makeup. I thought all was good after I had snuck around and managed to shave my legs again without anyone noticing.

That was until I snagged mom’s hose on an unkept fingernail and ran yet another pair of good stockings or pantyhose. I learned the hard way to take better care of my nails as well as the rest of my body on my path to femininity. Little did I know, paying attention to just the smallest of details would rule my world as I climbed my gender path towards my dream of living fulltime as a transfeminine person.

My major problem was that I was restricted to viewing what a woman’s life was like from the outside in a male dominated family. Through it all, my mom became my mentor and role model more than she ever knew and it went way past just using her makeup and wearing her clothes. I could see how she worked behind the scenes to make sure that the family ran as smoothly as possible. Way past all the traditional female duties such as cleaning and buying groceries. She taught me all that a ciswoman could be at a young age. All the time not realizing what she was doing because she actually had a daughter, not a son.

It was not until I began to get out on my own as a novice cross-dressing transgender woman did; I really have to develop my sense of detail. It was very difficult for me because I was never a detail orientated person. When I went out initially as a trans woman, there just seemed to be so much to concentrate on and remember to do to succeed. Even if I thought I had perfected my fashion, hair and makeup for the evening, there was the problem of putting it all together outside of the mirror and getting all my movements down, so I did not look like a linebacker in drag. The details weighed on me heavily and they were all I thought about in every spare moment I had. So much so that I needed to think ahead to which gender I was at key moments in my life.

It all carried over into life events such as weddings and dances when I had to step back and wonder what I would be wearing if I ever had the opportunity to attend as a trans woman. Sadly, I did get to experience attending a funeral when my wife Liz’s dad passed away after I had transitioned. I wore my best black outfit and did the best I could to blend in properly with all the other ciswomen who attended.

The funeral was just another reality check for me as I needed to face how far I had come in my male to female femininization journey. At my age, I always knew attending a funeral as me was a possibility, but I never knew how real it was until it happened. At that time too, reality and details were becoming increasingly important as I expanded my life in the world to new and exciting groups of strangers such as in spiritual circles and Meetups of writers in Cincinnati. They were the first groups of strangers that I had ever met outside of LGBTQIA+ support groups I attended locally and at the Veterans Administration in Dayton, Ohio. Meeting new people as I said was exciting and kept me active at an exciting time of discovery in my life.

By this time, repetition replaced my need for detail as my makeup habits, along with clothing needs became ingrained as I finally knew who I was in my life. No more searching in a dark lonely closet for an answer. I had it with the help of the world of new and exciting discoveries I was in. I had brief moments of releasing my gender euphoria before but nothing like this before as all the possibilities of the world were opened to me. When I sought out and was approved for HRT or gender affirming hormones. Which I write about a lot. New emotions outweighed the need for details as I moved ever closer to being the person I always wanted to be.

One thing I never forgot as I male to female transitioned was how I was treated early on and how I needed to respond by going back to my cross-dressing drawing board time and time again until I got my details correct. There was so much more to what I was trying to do than my home mirror had told me as I tried to exit my gender closet for good. All I knew was, once I was released from my loneliness, I never wanted to go back. I spent as much time as I could out in the world working on my feminine presentation so I could overcome my testosterone poisoned body and make it.

I cannot stress enough how much of my journey has been filled with fear and or panic when I lost key male privileges such as intelligence and personal security. Details just weren’t enough to help me through all the anxiety I felt meeting strangers in my new exciting world. In fact, just yesterday, I felt the same old twinges of panic sneak in when Liz’s son and I had to take our old lawn mower into the shop for a tuneup. After all these years in the public eye and I still have the same problem is ridiculous I know, but I still do when I am entering predominantly male spaces for any reason. Again, all went well as the young person at the mower place was only interested in taking care of us. Not my gender.

All in all, the extreme work I put into crossing the gender border was worth it as I achieved my goal of living the life I wanted to live. Even though there were times when I did not think I was going to make it.

Thanks so much for joining me with my life experiences. Hopefully you can gain some insight into your life from them. Comments are always welcome!

 

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