Showing posts with label transgender woman. Show all posts
Showing posts with label transgender woman. Show all posts

Sunday, August 16, 2026

Being Better as a Trans Woman

 

Image from Donald Gianetti
on UnSplash.


Often you must be better than the world to prove yourself as a transgender woman or transgender man.

An easy example would be we have to be better with our appearance. Because of the current lack of concern over appearance with many ciswomen and cismen, it’s an anything goes fashion world when women are wearing their pajamas and slippers to shop at a big box store, I won’t mention. Because we trans persons have so far to come in the appearance department, we cannot set our appearance bar that low or even want to.

Another problem with appearance is that we have had so few natural advantages to help us along when we first take the tentative steps out of our gender closets. In the case of transgender women, very few have the advantage of escaping the ravages of puberty which gives us angles, broad shoulders and deep voices. So, unlike the curves and softness we see in the women around us and envy so much. To get by in the world as a cross-dresser, we must strive to cover our natural flaws and act like we are not doing it.

The good thing is that ciswomen provide us with a big range of fashion to work from. Some wear dresses, some wear pants, some go without makeup and others don’t as life goes by. All you have to do is grab a spot you feel comfortable in and try to maintain it in a world of curious ciswomen who want to know more about you. You notice I said try to maintain it because early on, finding the best fashion and learning hair and makeup are major challenges we face. As our old bodies do not want to cooperate with the new path you have set them on.

Since I have always felt more comfortable in pants, leggings or well fitted jeans as a trans woman, I often took in criticism from other novice cross-dressers when I went to mixers in pants. Per norm, I did not care what they said about wearing pants as a man all the time so why I would do it as a woman because I was noticing how stylish some women look in their pants. I even had a glamorous silky black low-cut pants suit I wore to prove them wrong. Plus. most importantly what I wore was none of their business if I was aiming to be as good as the world of ciswomen in public at large who were increasingly wearing pants in their wardrobes. Not a bunch of cross-dressers at a social/mixer.

The more I was out in the world and interacting with the public, I discovered that appearance was just a small part of being better than the next person. Following some rough early experiments with my presentation as a transfeminine person, I settled into noticing who was noticing me. I learned men rejected me almost completely (which was fine by me) and women on the other hand wholeheartedly accepted the new me who wanted so badly to be in their world. The percentage of gender acceptance I received totally surprised me and I had to up my game to get better when I faced the public with so much more at stake.

Suddenly, women wanted to talk to me, and I was initially surprised and had to talk back. Then as now, I am very self-conscious about my voice, and it took me what seemed like an eternity to understand my communication skills centered more around what I was saying more than how I was saying it. In fact, I needed feminine vocal lessons to learn more about how women speak to each other. Primarily when men were not around. I also leaned the power of passive aggressive speech behavior in cis women and how it could apply to me when a potentially smiling face did not equal a supportive woman who could just as easy stab you in the back. After I tended to more than a few claw marks down my back, I adjusted to the new world I was in and survived by being better than them.

All these steps led me to pursuing an expanded transgender bucket list of potential things I wanted to do as a trans woman. To learn if I would want to do them on a permanent basis. As my checklist grew, my confidence did too and I discovered how natural I felt in the new exciting yet scary world I was in stripped of all my old male privilege such as dealing with my own personal security. With the menacing male scowl being gone, I had to rely of my new feminine senses to get me by and to stay out of potentially dangerous situations. It was all a major lesson of being better in the world out of a sense of pure survival as a new transgender woman.

At that point, destiny set in for me and set my life upside down as nearly all the loved ones I new and respected passed away. Leaving me all alone. To survive, I had to quickly quit being a victim and decide which direction my life would take. I took the feminine path, was approved for HRT or gender affirming hormones and prepared myself for a bumpy path ahead. At the age of sixty, I needed all the wisdom I had learned from a predominately male life and apply it all to a new female existence and exceed my own expectations.

By taking chances in the world, I had lucked into finding supportive ciswomen friends into my new life and I give them all the credit for the ease that it happened. And it made all the prep work I had done in my life worthwhile. Even still, I found I had to be better than the average woman to find my way and stick to it so I would not slide back to my old male ways.

Before I go, I would like to thank “Grace” for inviting me to write for her group “Empowered Trans Woman” on Medium. I really appreciate it

 

 

 

Friday, August 14, 2026

There Was Never a Plan B

 

JJ Hart, Back row far left
Girls Night Out.

Very early in my cross-dressing days, I always tried to have a plan b in the back of my head if danger approached in the form of my brother discovering me or my parents coming home early from work.

Seeing as how I had no effective plan to get out of what I was doing in mom’s dresses and makeup, I thought that somehow, I would have to just try to lie my way out of it and say I would never attempt it again. Knowing that was a deal with the devil I could never make and expect to keep. As I continued to cross-dress in the family mirrors, I finally had to throw caution to the wind and just go ahead and do it.

Years went by as well as the complexity of what I was doing as I tried my best to express my feminine self. At the least, I thought of better ways to hide away my resources from prying eyes and was successful all but once when I got careless on a weekend, I was away when I was waiting to go into the Army and start basic training. What happened was, I had just mixed my feminine clothes and wig in with a bunch of my male clothes thinking that one would disturb them until I returned. I was wrong and when I got back, everyone else in my apartment had not returned home for a college break leaving me all alone except for one other guy who had come over to visit.

As we sat around drinking a few beers, I decided to gather my courage and somehow asked would he like to see me dressed as a woman. Effectively, throwing all ideas of a plan b if he got up and bolted out of the apartment. To my surprise, he did not and was receptive to the idea, so I left to start the prep work needed to finally come out to another person. After I had taken the time to shower and shave my legs and face, I went into my bedroom looking for my feminine clothes, wig and makeup. Only to be shocked to learn they were all gone. Someone had stolen them when I was gone. All the plans for the evening I had were shattered as we sat around and then finished all the beer and nothing was ever said about him coming so close to meeting the true me. As far as confronting anyone about where my clothes, wig and makeup had gone, I decided to keep my mouth shut because I was so close to having to report to Ft. Knox in Kentucky for Army basic training anyhow. A final solution for a plan b during the next three years of my life. I knew I could not entertain any ideas of cross-dressing at all.

When I was discharged and Halloween parties with my friends became the only external form of feminine expression that I had, I needed to ignore any of the warning signs that I was giving away any idea I was not as masculine as I acted. I was so into going to Halloween dressed as a woman that I decided to take matters into my own hands and ignore all the plan b’s that I had thought up. Even to the point if some other person commented on my “costume” and the effort which went into it, I would just try to laugh it off. Mostly what happened was compliments from other ciswomen on my shaved legs and I even gained the nickname of “legs” with several of them which I had to act like I did not care. When deep down inside I was overjoyed and wanted more input. It took me years to understand what they were really saying was I looked good for a man dressing as a woman.

As more years went by and I became very serious about being a transgender woman and was attempting to hide it from my second wife, plan b’s became very important to me. In many ways, I had regressed to my childhood in the ways as I had to hide my femininity away from her. In addition to being very tuned in to when she got off of work, I needed to get better and better at makeup and eye makeup removal, so hopefully she couldn’t tell what I was doing when she was at work. The problem was that practice was making my femininized presentation more effective.  Success just made me want more and having a plan b at all was disappearing totally.

For the longest time, the only recourse I had was to attempt to lie my way out of whatever transgender activities I even had to resort to trying therapy to save our relationship. The gender therapist was wiser than I was and told me there was nothing she could do about my deep-seated gender issues. I was trying to buy time with my wife and save our relationship as long as I could, but the therapist was not a miracle worker and I quit going. Leaving me to wonder what I would do about finding the next plan b I desperately needed to hold my marriage together. Because I knew it would be just inevitable my wife would discover what I was doing as a transgender woman exploring the world and we would have a gigantic fight because I had promised I was going to stay home.

The problem was that I knew I was wrong and was just buying time until the next adventure I had in the world with the ciswomen that ran it.

Finally, what happened was I ran out of all needs to have a plan b when it came to me being a transfeminine person. I had learned to live freely behind the gender curtain which I had waited so long and worked so hard to do. In fact, it was the only big dream I had in my life. I then resorted to a new plan to live out my life the way I wanted.

 

 

 

 

Wednesday, August 12, 2026

All Along I was Just Me

 e

Inage from Gayatri Malhotra
on UnSplash. 

It took me decades of living to realize the simplest of all realizations…just discovering who the true me was all about.

It turned out I was so much more complex than the friends I had around me in how I felt about life. Which often help me back because I could not express how badly I wanted to be a woman. What I did was, I took the natural male response I inherited and internalized all my feelings. Naturally, the male response did not work and all it did was wreck even further my already frail mental health. If I could not cross-dress my anxiety increased and when I did my paranoia kicked in when I thought, I was getting caught.

As I added years to my life, the complexity of being a gender dysphoric person grew with the years. What did I do? I tried to outrun my problems. It wasn’t until the Vietnam War years and beyond did I learn that I would have to stop being a victim and stand up to living a life outside of the shadows of being a man. The idea of moving my family around and changing jobs all the time until I finally landed a job I wanted in a location, I wanted to be. That meant I climbed out of fast food and landed in a full service, casual dining chain which served alcohol which was exactly where I wanted to be.

With my dream job in place, I could concentrate on my feminine side by beginning to go to the small diverse LGBTQ parties I used to go to in nearby Columbus, Ohio. At those mixers, I was able to meet transgender mentors who would define my future. From them, I learned a path to my dream may actually be possible. The me I had always dreamed of was finally beginning to emerge. Much to the chagrin of my long-time second wife who actually went with me to a few of the parties. Probably, just to keep track of me. One thing was for sure; my wife never liked the trans woman I was becoming. Back in those days, I was still trying too hard to dress to impress and my wife was right, my dresses were too short, and my makeup was too heavy for her liking.

As she normally was, my wife was right about my appearance, and I tried my best to tone it down when she was around. Most of the time to no avail. I was stubborn and had to live out my so-called adolescence years of cross-dressing before I learned how to dress to blend in with my wife and the ciswomen around her. As I always say, sadly she passed away before she ever got the chance to meet the mature transgender me. I know we could have not stayed married but maybe at least be friends.

The question became, what was I doing with my time when I was discovering who I really was. What I was doing was exploring as close as I could what it would be like to live a whole new life behind the gender curtain. For the most part, I was successful as I made my way from the relative safety of the gay venues I was frequenting and jumping into the more challenging straight sports bars I was used to going to as a man. By never causing any trouble, always smiling and most importantly by tipping well, I was able to establish myself as a regular in several venues which seemed unreachable to me just a short time before. Most importantly, I was able to bring my love of sports from my male life into my female life with no problems. Which was a surprise to me.

As I did, I discovered the true me was not that far removed from the old me. Basically. I had just changed my appearance and gave up basic male privileges such as perceived intelligence and personal safety, and the best was yet to come as I was able to begin to move around freely as the new me in a world run by ciswomen. Quoting my second wife, I didn’t “make” a terrible woman after all. Primarily because I was not “making” anything. I was becoming me. Sure, I knew on occasions I could have done a better job, but I never allowed myself to be a victim and moved on back to my gender path. Which was beginning to change dramatically because I was beginning yet another  major gender related transition in my life.

First, there were the two obvious mental transitions I went through including the initial once when I realized I was so much more than a weekend parttime cross-dresser which went all the way to that fateful night at a local TGIF Fridays when I had had enough of that thought pattern and went out to be with the other ciswomen just getting off of work at a nearby mall.

From that moment on, I knew I could never go back to my old unwanted male self. But still, I felt as if something was missing in my life. It was because I was still missing the obvious transition of all as I finally realized I was never a cross-dresser or a transgender woman; I was just me.

I wish I could take credit for being persistent and intelligent that I kept on pushing to find me but I can’t. That credit goes to all the ciswomen who I became close to over the many years of struggle I endured. And yes, my second wife is included because she was the first to say be man enough to be a woman and make life easier on both of us. As we all know, many women are good at reading small lights inside of a person (unless you are fighting an unsupportive spouse) which is a point for another blog post.

I can’t say enough positive about all the women in my life who helped kick me out of my male nest and into the world of women. They knew me better than I knew me.

 

 

 

Tuesday, August 11, 2026

Understanding is the First Step to Overcoming Fear

 

JJ Hart (Center) on a 
girls' night out. 


Before you can overcome fear, you need to understand exactly what you are afraid of.

I know I was petrified of leaving my closet behind and heading out into a world where I knew little or nothing as a novice cross-dresser. It took me years to overcome most of my fears except the ones I never did. Such as going into male dominated spaces by myself as a transgender woman. For some unknown reason, that one thing has always been a problem for me and my anxiety issues about coming out in the world.

When I was younger, I always thought either I would grow out of my need to feel feminine in all ways or somehow, I would lose my fear of doing it. Of course, I learned quickly that anytime soon I would not be outgrowing my urges to cross the gender border into a feminine world. In fact, my urges were getting stronger which led to more fear and anxiety about the future of my life. Out of sheer survival, I had to find out why I was so scared.

The easy way out for me was just by thinking that making the gender jump into what I perceived as greener pastures, was the reason I was so scared. I was using the dresses and makeup I had acquired to hide behind and feel better in times of duress. I was too new at the gender game to consider ideas such as gender privileges which I was accumulating as a young man with out even knowing it. Privileges such as never having my intelligence questioned or having an innate sense of personal security were never questioned. I found I would not have to until much later in life when I began to present well enough as a transfeminine person to get by. All of a sudden, passing as a woman meant more than just having a man open a door for me. I had to take the good with the bad if I was ever going to be successful in making it to my dream of living as a woman on my own terms.

The more involved I became in my male to female femininization, the more I discovered there was no easy way out. Which frightened me more. I always equate it as me busily painting myself into new life corners as a trans woman which there was no easy escape from. Finally, I did see a brief escape from my unreasoning fear was when the transgender term was being popularized to gender conflicted people like me. There was a term which described people such as me who did not fit into the cross dresser-transvestite mold or the more extreme transsexual person. From the moment I saw the trans term, I immediately knew it described me. It certainly took long enough for a term to come along, which helped me, but it finally did.

Being able to read about other more accomplished transgender women and trans men helped me to understand my fears and why I was feeling them and the new less rigid gender spectrum terms helped me immensely. For the first time in my life, I could pinpoint why I was feeling a certain way and at the same time calm most of my anxieties. Gender diversity became my motto in life as I really began to explore the world of ciswomen for the first time. I had left the men’s club (and they knew it) and wanted to join the women’s club if they would have me. Yes, the world of ciswomen would have me which lessened my fears and anxieties immensely. Mainly because I had a better understanding of where I wanted to go.

Looking back, I do not know why I took so long to try to have a better understanding of who I really was. I could blame the usual suspects such as my old male self or my second wife who put up such a battle against me transitioning when in reality it was all on me. In the would of-should of department, I always should have faced up to the fact I was more female than male and should have not made life miserable for my wife when I did not “man-up” in her terms and become a woman. I guess I was never one to take the easy way out.

If I had taken any of the excess time I was wasting, I would have taken the time to calm my fears by understanding who I was as a person and try to build a better feminine person I learned I could be from all the male building blocks I had left behind. As I looked around at the new world of ciswomen, I was seeking admittance into, I realized they were more diverse than even I had given them credit for. And I would not be shunned for wanting to do something like wearing my favorite team’s jersey on game day in one of the sports bars I was a regular in because other women were beating me to it by wearing their jerseys It made my fears evaporate as my life became more fun again and certainly more fulfilling as I had always wondered what it would be like to cheer my favorite teams on in the venues I was used to going to as a woman and not a man.

Once I finally started to have a basic understanding of where my fears were coming from, I was able to better keep them under control. Which, in turn led me to being more relaxed with a chance to let my long hidden trans woman personality shine through.

I know it is difficult for all of you who are just getting started along your gender path to not be afraid because of what is at stake but if you are able to slow your life down to take a closer look at it…you will stand a better chance of understanding your fears and anxiety and living a better life.

Thanks for reading along and I hope my experiences can help you anyway I can!

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Monday, August 10, 2026

Stepping Out as Yourself


Image from Max Anderson
on UnSplash. 

Stepping out into the real world and leaving my closet and mirror for the first time was difficult for me. For lack of a better term, I was leaving everything I worked for in my male life behind.

As much as I hated my dark, lonely gender closet, I found it to be a safe place to be when I needed it the most. My ability to put on a dress and makeup soothed my soul, if only on a temporary basis helped until I needed to take another high heeled step into the real world where I so desperately wanted to be. To put it mildly I was scared to death when all my male privileges I had worked so hard to learn were stripped away and I was starting all over again. It was different when I could not rely on a menacing facial expression or an occasional bluster to get me by.

Stepping out into a new feminine world for me meant I needed to immediately begin to work on building a new personality which would grow with me as I worked my way towards my dream goal of living fulltime as a transgender woman. This was the same period of time that I was obsessed by my feminine appearance, so I had a lot on my mind. As I struggled day to day about what gender I was going to be. All too soon, life meant so much more to me than buying a new dress or skirt all the way to how I needed to change my old male movements when I wore them.

As I was forced by being in the public’s eye, I needed to understand exactly what I was getting myself into. So much more than the pretty clothes that I saw the girls around me wearing. If I needed to be more like them, I had miles to go on my gender path to get there. All I knew was at that time, most of the ciswomen I encountered were nice to me. Every little bit helped me learn what my future could be like if I kept stepping out and away from my old male past. Plus, problems kept occurring with my second wife and my male self who saw the changes in me as a threat to their future lives. My second wife saw her husband slipping away and my male self-saw his whole future gone if what I was doing continued.

Through it all, I was able to establish myself as some-sort of a successful cross-dresser before I transitioned into a transgender woman one fateful night when I thought enough was enough and I had to do more to continue up my gender path. Before I became lost entirely and had to reassess where I was. What I learned was that I was actually further along towards my transfeminine goal than I thought I was. I learned the hard way when I was able to be successful when I went out for the first time to enjoy a drink with a group of ciswomen from a nearby mall who just would go out and socialize after work. It was something I always had wanted to do as a transwoman, and I was amazingly accepted into their circle. I guess you could say that night I really stepped away from my old male self and loved it.

Before I knew it, my new shiny shoes (flats this time) were stuck in gender quicksand as I had stepped into a place that I never wanted to get out of. One thing was for sure, if anyone came along with a rope trying to rescue me, I would have turned them down. I was having too much fun challenging the world as my new transgender self to ever turn around and go back to a boring life as a man that I had stepped away from.

Sure, there were still many times that either I was scared to death of where I was going or was out and out rejected by the world, but those times were getting fewer and fewer apart. I was headed towards my dream goal which was slowly coming into focus as a doable project. I say project because I had never attempted such a thing as jumping the gender border to slide behind the gender curtain in my life. When I finally accomplished my goal of being allowed to exist in so-called women only spaces, I certainly was not going to give up all that I had earned.

By this time my second wife had passed away, and my old male self was seeing the writing on the wall, and his days were numbered too. Which left me all alone to make my key life choices. Still after much thought and consideration, I finally gave in totally to my feminine side, and I set out to build a different yet better life with my new ciswomen lesbian friends. All of them helped me round out and refine the woman I always wanted to be. Most of the work I had already put in, so I did not have that far to go. Mainly the only place I needed to go was with my dealings with men. Even that turned out to be relatively easy because most men left me alone because I was not attractive enough or just wanted me as some sort of a fetish object. All my problems went away when my lesbian friends taught me I did not need a man to be validated anyhow.

As stepping out as a transgender woman in the world became natural to me, a whole new universe of life came alive for me. Especially when I was approved for my long-term dream of starting HRT or gender affirming hormones. Something that my second wife always recoiled at the idea of, but on the other hand, my current wife Liz loved. The essence of being on my hormones just carried over into me stepping out into a new world with confidence I had never known before.

 

 

 

Sunday, August 9, 2026

Your Lines in the Sand as Gender Markers

 

Image from Sonnie Hiles
on UnSplash. 

For the longest time, I set new lines in the sand as I progressed along my path as a novice transgender woman.

Sometimes, the lines were very faint, and I had a difficult time seeing them. All the way to deep trenches I needed to leap across. It all depended on what I was doing at the time. For example, when I was just dressing in mom’s dresses and putting on her makeup, the lines were very faint and easy to cross. In my mind, I was a boy one moment and a girl the next. A very black and white way to view myself, or so I thought until I grew older.

Instead of growing away from my cross-dressing years, I ended up growing into them by finally coming to a better mastery of the feminine clothes I wanted to wear and maybe more importantly, the artform of applying makeup which was a very deep line to cross for me. If I had worked as hard on my studies and sports than I did on my femininization projects, I would have certainly made the dean’s list every year and starred on the school’s football team. I was mentally built differently because of my gender dysphoria and could not decide for the longest time which gender path I wanted to follow because the feminine path was primarily there for an escape. When my male life became too stressful, I could shave my legs, slide carefully into my pantyhose which I had purchased myself from jobs I had worked and put on a dress and feel better instantly.

Even though I did not want it to happen, I began to build male privileges from doing a good job raising my daughter as a father and working jobs I was promoted at. When I did, I knew I would have a lesser chance of having just a small line in the sand to jump across if I ever needed to. Little did I know, how much both of my efforts would come back to help me in my later years when I encountered severe gender obstacles as I went behind the gender curtain as a transgender woman. I should say finally went behind the curtain since it took me decades to do it.

The problem arose with drawing more and more lines in the sand that my life as a transfeminine person became more complex quicker than I ever imagined. Often, I have described what I went through as sliding down a deep slope grabbing onto whatever I could to maintain the male life that I had. Just to watch it slip away. It led me to falling off the deepest cliff I could have ever imagined when I put away all my male clothes for the last time, went on HRT or gender affirming hormones and put my male life behind me for the last time.

By this time, even my stubborn old male self was admitting he had made a mistake by holding on as long as he did. All the covering lines in the sand I was about to cross with his own ideas did not work, as I was able to negotiate all the challenges thrown at me by ciswomen in the new world I was in. In many ways, I had come full circle when I learned how valuable all the building blocks, he had given me, just gave me more resolve to be a better trans woman. The daughter I mentioned earlier came around to be my earliest and strongest supporter so all the time I put into being with her when she was young came back to help me. Then there was my employment in the restaurant industry which turned out to be very lucrative for me in several ways. The first was with money and the second was with the opportunity to work closely with groups of varied ciswomen. In many ways, I learned what they faced in their lives gave me insight into what I was going to face when I joined their world.

For example, I learned what alpha females meant to the group of women as a whole, and if I could gain their support after I transitioned and joined their world, it would be very valuable to me. In many ways I found that good strong alpha ciswomen from super butch lesbians on down could do to help me erase my lines in the sand. I can’t begin to say how much they helped me. Even my second wife who was an unapproving alpha woman to me was a role model and taught me more about her life than she ever knew. Before she passed away tragically at the age of fifty from a massive heart attack. So, she never got the chance to meet the mature transgender me after I had crossed all the lines in the sand I needed to cross to just survive.

From all sorts of ciswomen, I learned that women come in all shapes and sizes with various levels of support of the transgender community. Many support us from afar and it would be different if it was their husband seeking to make his own line in the sand and become a transgender woman. On the positive side, there is now more information available to spouses of trans women to understand what seemingly a glaringly selfish path is to go down for their husbands. Especially with the husbands who have gone to great lengths to hide their gender passions from their wives for many years. When I step back and look at all the relationships which have ended over the years because of gender dysphoria, I try to wonder what would have happened if my wife was the one who wanted to draw his line in the sand and said enough is enough. I can’t take it any longer.

Of course, now I am biased and think I would have accepted my former wife bringing home another woman to get to know. How would my old male ego react? I am ashamed to say it now, but my old male self would have had to force the issue and solve it once and for all in his favor. Drawing his own line in the sand.

If you are at the point of drawing a new line in the sand for yourself, make it an achievable goal so you do not get discouraged. Finally, stay flexible with your lines as you know some will be deeper than others. If you do, you will stand a better chance of success.

 

 

Wednesday, August 5, 2026

The Vampires Approved Me

 

Image from Mike Lloyd 
on Unsplash. 

Yesterday I needed to visit the Veterans Administration vampires to have my blood labs done. Fortunately, I could just go to my local branch office to get them done and not have to go to the congested mess which is the downtown Cincinnati VA Hospital.

I chose yesterday to go because it was a beautiful early August day here in Ohio with coolish temperatures and bright sunshine for the relatively short drive I needed to make to get there. For the occasion, I decided to wear my new Libra themed tank top with leggings and my new tennis shoes. After a close shave, a lite coating of makeup, and lipstick, I brushed out my long hair and was ready to go. Actually, compared to the few other ciswomen I encounter at the VA, I was nicely dressed and ready to face the world as a transgender woman.

When I arrived at the VA, it was a very uneventful visit as no one seemed to notice me for anything other than who I was, an elderly woman who did not have to wait long to be seen and have my blood drawn. Since I was emboldened by the experience, I decided to stop by my wife’s Liz and I’s favorite coffee shop to pick up some breakfast sandwiches and coffee. My morning continued to go good as their drive-through was nearly empty and I was greeted cheerfully. Before I knew it, I had my order and was headed home. It is the coffee shop we go to which has the big LGBTQ flag on the wall, so we always try to support it.

The best part was that only a couple of hours later, the doctor who wanted the bloodwork done received the results and everything came back OK. Which means I am clear with the vampires until I have my Hematologist visit downtown this fall. It is important mainly because it is when I have my Estradiol levels checked. It is certainly no fun going downtown and having to find a parking place and walking but there is nothing I can do about it.

In the meantime, I took my brief moment of gender euphoria and enjoyed it for what it was…a brief moment to be the person I always wanted to be. I was just being me basically for the first time in my life. Now all I need to do is string together more of these moments to make them my reality.

Just a short post today to let you know where I have been and I will be back with you with a longer post tomorrow.

Monday, August 3, 2026

Letting Tomorrow take care Of Itself as a Transgender Woman

 

Image from Valentina Conde
on UnSplash.

Since I was always a person who had a difficult time living in the present, tomorrow always loomed large in my mind.

I think it all started when I began to rebel against the masculine world I was being forced to live in and always thought tomorrow could be better. It turned out that all the wishing and hoping I did for a better tomorrow turned out to be wasted time and energy, I finally needed to take matters into my own hands, stay in the present and do something about me being stuck in my dark, restrictive, gender closet with only a mirror to help me.

It took a quantum shift of thinking on my part to even thinking about how I could change my life. First of all, it was nearly impossible for me to quit daydreaming about the next time I could cross-dress in my mom’s clothes and try on her makeup. Any time I was not actively being engaged in male activities, I was hoping that soon I would be glimpsing a view of me in a favorite miniskirt I had found by accident at school outside of the girl’s locker room. If the girl who left it behind did not want it, I certainly did before a janitor found it and threw it in the trash. I was overjoyed to add it to my small but growing feminine wardrobe at home. Hopefully away from any prying eyes who may find it.

Somehow, I managed to hide my “treasures” away and add to them with my own meager funds I had earned from my rural newspaper route and from chores I was doing around the house. I will never forget the excitement I felt when I found a pair of women’s shoes that fit me in the department store where I was sneaking in to buy my makeup and panty hose. The whole process made me feel good because for once I was not relying on anyone else to help my cross-dressing along. It all was just me, and I was in the present doing it.

As I moved along in years and experience, I increasingly wanted to break out of my dark closet to see if I could exist in the world, in the present for once as the person I was coming to believe could be my true self. I learned the hard way that the public would not be as forgiving as much as my mirror was as I was treated quite rudely the first several times I went out. Even in places I should have had no problems in such as the big shopping malls back when they were popular. I couldn’t seem to dodge the giggles and stares I got from the teen girls before I learned to stay in the present, be who I was and begin to blend in with the group of other ciswomen in the mall. I learned the hard way to dress for them and not rely on some sort of trashy look that appealed to men. Which was getting me clocked as a man in drag every time.

All this new reality was teaching me I could indeed enjoy the present when I was out in the world. But not enough to keep me there when I was back in my unwanted male world. I have always wished I could get back just a portion of the time I wasted daydreaming of how it would be if I was the only ciswoman in a business meeting I was in. I know I could have been more effective…if I could have been accepted. Which I would not discover how difficult that would be until I got out further in the world as a transgender woman. I will always remember how I was shunned by a small group of men I somehow became involved in a discussion with when I first came out of my shell. Quickly I discovered, as a woman among cismen, I would have to fight for my right to be heard on an equal basis.

The more I was out in the world, the more I was forced to stay in the present. If I did not, I could find myself slipping back into old male habits which would give my past away much sooner. Such as not employing my old “stay away” male scowl and replacing it with a much more pleasant feminine look which said I was happy to be here. Which got me by. Other areas of just being a woman I needed to concentrate on was how I moved around in the world when I was still trying to juggle being in both worlds of male and female. One day I needed to be feminine, and the next masculine ended up taking a real toll on my mental health as I did not know somedays what present I was supposed to be in.

Plus, the one aspect of being in the now as a transgender woman was the one I always mention, communication. As I was blissfully (sometimes) going along my gender path, suddenly more and more ciswomen wanted to know about me and were curious why I would be in their world. I was totally blindsided when I needed to start and participate in entire conversations with other women who appeared in my world. I discovered communication went way past just how my voice sounded into exactly what I was saying and how fast I could pick up two uniquely feminine communication aspects. Non-verbal communication and passive aggressive behavior. The normal ciswomen who interacted with me ended up using all their skills to size me up and often it turned into quite the contest that I needed to stay on my toes to get through.

Eventually, surviving all the gender wars I went through, made me a better, more well-rounded trans woman who could hold her own in the world. Primarily because I had built up the confidence to do it, and it became my number one accessory. So, what if my makeup or walk wasn’t exactly correct, I knew who I was and it showed. There was no blood in my water for the human sharks around me to come after.

All those years of trying to get into my present and stay there finally paid off for me, but only after I had paid all my dues.

 

 

 

 

 

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!

 

 

 

 

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.

 

 

 

 

 

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.

 

 

 

 

  


Being Better as a Trans Woman

  Image from Donald Gianetti on UnSplash. Often you must be better than the world to prove yourself as a transgender woman or transgender m...