Showing posts with label cross dresser. Show all posts
Showing posts with label cross dresser. Show all posts

Saturday, May 16, 2026

Chance versus Choice as a Trans Girl

 

Image from Brooke
Ballentine on UnSplash.

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

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

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

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

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

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

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

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

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

 

 

 

 

 

Friday, May 15, 2026

When Every day is Day One

 

JJ Hart

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

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

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

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

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

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

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

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

 

 

Thursday, May 14, 2026

A Trans Girls' WOW is Real

 

Image from Raamin Ka
on Unsplash.

One of the many reasons I kept moving towards my dream of living as a fulltime transfeminine person were the “WOW” experiences I was having.

Of course, I was a fan of the gender euphoria I experienced when I cross dressed in front of the mirror as myself for the first time. The downside was the buzz from the euphoria did not last that long and then I was stuck back in the life of my unwanted male self. Deep down I knew there was much more to what I was doing except putting on pantyhose, makeup and a dress. I just was not ready yet to face my truth in life.

As I got older and more experienced in being a cross-dresser, I began to separate the gender euphoria episodes with the WOW times I had on very rare occasions. I suppose the reason was that I felt the euphoria so much deeper in my soul that I was doing the right thing with my life. It was then, that I began to seek out a term which described my life to me and it just happened to co-inside with the new use of the transgender word. When I first read about it on our new computer, I thought WOW that is me and I finally made a discovery I could really use to feel like I was not alone.

This new thought pattern led me into the belief that I was no longer a man dressed as a woman when I left the house, I was a trans woman of my own experiences capped off by the TGIF Friday’s experience when I gathered the courage to go out one night and mingle with a group of ciswomen just getting off of work at a nearby mall. It turned out to be a first of a kind WOW experience as I was treated fairly and even managed to put my fear aside and stay for a second drink when I pondered the fact that my life would never be quite the same again.

As I followed up on my Friday’s experience, my emphasis began to be on increasing my visibility out of the gay venues and into the straight ones. I WOW ed myself when I was able to be accepted as fast as I was in most of the liberal places I chose to try. Such as sports bars where I could enjoy a large beer and follow my favorite teams. No longer as a man but as a transgender woman when everybody of any worth left me alone. The WOW was real when I followed my basics of never causing any problems, being friendly to the staff and tipping well. It worked for me nearly every time except when I slipped up and tried to go to a couple redneck venues just to see if I could.

I think then, my WOW’s slowed down as I needed to slow down my advance into the world of ciswomen because of negative pushbacks from my male self and my wife. Both of whom did not want to see me as a woman of any type. My male self because he did not want to lose any of the male privilege, he worked so hard to build up, and my wife because she did not want to lose her husband. Both were quality opponents and put up very big fights. At the time, my inner female simply retreated and waited for her chance to live as part of my overall dream. She had temporarily lost the battle but eventually would win the war.

In order to win the war, my feminine self-had to continue to have the courage to carve out a totally new life as a trans woman in the straight venues I mentioned. I had WOW moments when I was even able to communicate effectively with men who were not intimidated by a woman who had left the men’s club. The whole process just helped me to be a better, more rounded person. I figured if I was starting from scratch again in life, I better do my best to do it the right way.

I must have been successful, because I was able (with a little help from destiny) to start a new complete life as a transfeminine person. My biggest WOW I always mention was the small group of diverse women friends I was able to fit into. Most were lesbians but some were not and even one was transgender. The best part was that I was beginning to enjoy my new life immensely and was starting to fit right in as I build in layers of living between the new feminine me and my old male self no one ever knew. Mostly from going to artists’ and writers’ meetups in Cincinnati as a total stranger and sharing my ideas of writing a blog. It all helped me to establish myself as me and help do away with the remaining shyness I had from meeting strangers.

The only real negative I had was a chance meeting with a drunk lesbian bigot who wanted to know my “real” name. The more I attempted to ignore her, the more she would not leave me alone until my future wife Liz came back and ran her off. The whole negative experience happened years ago at a lesbian Valentine’s dance in Cincinnati, but I remember her obvious dislike for me to this day. Certainly, a negative WOW since my relationship with the lesbian community had always been so positive.

As you can tell, my WOW experiences always came from me stepping out of my male gender box and trying new things. Some successful, some not but if I did not try, I would have never known how bright my future could be. My lesson to all of you is to be careful as you follow your own gender journeys, the world is a changing place for all of us and finding our niche is becoming harder. Hopefully, you can stay the course and be successful.

 

 

 

 

 

Tuesday, May 12, 2026

Success is no Accident in the Trans World

 

Image from Priscilla du Preeze
on UnSplash. 

Success is definitely no accident in the world of transgender women and transgender men. Very few of us survive our puberty by having no natural characteristics of our authentic selves that we want to be.  I know I wanted nothing to do with the size and angles my male body was willing me to have without my permission.

It was not until I became very serious about my male to female femininization project did, I take the necessary steps I needed to take to begin to ensure my future successes were no accident. The first step I took was to try to make myself smaller for I could fit into more stylish feminine clothes. Naturally, all I could do to make me smaller was to go on a diet. I was successful in a short period of time because I had a very active job and my high male metabolism was still working well. I ended up losing nearly fifty pounds quickly and had the fun job of going back to the thrift stores and searching for new clothes in my size and trying them on.

The next step I took to improve my work to become more feminine to the public was to take better care of my skin. Every day I was careful to moisturize my face after I shaved to make it easier for me to use less makeup because I knew less was more when it came to using makeup. It was a start but was all I could do without the public and my wife beginning to notice a major change in me. Even so, I was proud of the beginning steps I was taking towards my overall femininization.

It proved to me that over the long haul, none of this path I was on would be easy to navigate as I sought to cross the gender border. Also, what I did not know was how much more difficult my life would be because just looking like a ciswoman would not be the end result of the process. It would just be the beginning when I left the mirror and challenged the world as a novice cross-dresser or transgender woman. I never realized the depth and scope of the world women use to run their lives. With or without the help of men.

By accepting the challenge of femineity I was seeking, I was also challenged to move like a woman and more importantly communicate as a woman because I discovered quickly how many other women wondered what I was doing in their world. From the ease of dealing with clothing stores clerks to having conversations with women at restaurant/bars I was at, I found I was dealing with much more interaction than I ever had as a man. My new success was no accident, but I needed to work hard to keep it and always stay aware of my new surroundings. One slip up and the setback could be tremendous and discouraging to my dream goal of being able to live full-time as a transfeminine person.

Many times, my frustration grew over the decades that I struggled with my gender issues. Was I going too fast by going out into the world, or not enough to keep learning what I needed to know to progress along my gender path which kept showing me infuriating stop signs along the way. Particularly from my male self who was becoming very successful in his business world. He was making it difficult to choose between his growing male privileges and living the life I had always dreamed of. Ironically, it was lessons he learned at work which were carried over to my female life that proved that success was no accident. If I wanted my goal bad enough, I could achieve it.

As I progressed with carving out my new feminine life as a trans woman, I found that my successes were painting me into corners which were difficult to get out of. I had nights when butch lesbians were flirting with me and buying me drinks until I ran out of time and had to be back home before my wife was take my makeup off then calmly try to wind down by watching television. I was on the gender rollercoaster going from one high to another and eventually it was too much to take.

Before I broke for the final time and had to make a decision between staying with my wife as a man and deciding to live my life as a woman, she took my decision away and suddenly passed away. Leaving me all alone with my other woman who happened to be me. It took a while for the shock to wear off, but when it did, my internal female took right over and claimed her territory in my life. She thought success was no accident and she had claimed hers by paying for those dues all those decades when she was hidden for the most part. In the light of day, she flourished and never looked back. Especially when HRT or gender affirming hormones were introduced into her old male system.

The ultimate measure of success is coming around and transitioning ourselves from transgender into just being ourselves. Many of us have to go through extensive gender realignment surgeries to do it, and some not but that is OK. Whatever makes you whole as a person is the final key to the lock or piece to the puzzle. I am sure that whatever the case, everyone who succeeded in finding themselves would agree that success was no accident. They had to work hard to achieve it.

If you are on your path, just keep up the hard work you are doing, and you can find success also. Pursuing such a complex journey will never be easy but as the saying goes, if it was easy, would it be worth it.

Thanks to all of you who read along with my posts! All your thoughts, comments, claps and subscriptions are always welcomed.

 

 

 

 

Sunday, May 10, 2026

Mother's Day and the Battle for Gender Supremacy

 

Image from Daiga Elaby
on UnSplash.

Before I get started on today’s post, I would like to mention Mother’s Day, and all it means to me. First of all, it gives me the chance to remember all the problems my mom went through to have me. Such as, going through three still born babies before my parents kept trying and had me. Without their determination, I would not be here today. Which is the main reason why I adopted my mom’s first name as my legal name when I changed it years ago.

Plus, even though my mom and I were much alike and fought quite a bit through my youth, I managed to use her as a roll model as I slowly grew into the daughter, she never accepted having. I view her now as a one of kind woman who presented herself to me as an unknowing roll model. Happy Mother’s Day to all of you reading today who may be ciswomen and birthed your own children! We all know how important you are to the world. If your mom is still around, do your best to try to bridge the gender gap. Although I was never able to do it with mine before she passed away years ago.

Now, on to the post for today which has to do with my remaining male gender and how he got in the way of my transfeminine progress in life. I already mentioned the fights I had with my mom as she taught me to fight like she did. Bring anything you could think of to make sure you have at least a decent chance of winning the battle you were in. I think she indirectly taught me valuable lessons about fighting as a girl because I had to resort to being mental and not physical with my fighting.

As it turned out, just the aspect of having fights with other males never materialized much with me as I was growing up. I tried to hide behind liking sports and cars to hide my true love of fashion and makeup to keep the bullies away and for the most part it worked. It also worked when I failed at trying something such as sports, getting beat, and having the chance to run home and soothe my feelings behind one of my favorite dresses and makeup.

This plan was all well and good when I was just dealing with just minor athletic events and became much more serious when it came to activities such as work and life in general. I quickly learned that if I was to be successful, I could not just take my feelings home and cross-dress, I needed to stay there and fight. I needed to push hard to keep my transgender issues at bay and take care of myself. Even though in the background, my feminine self was always waiting to get out and thrive in the world. Sort of like that app on your computer which is always running in the background. Because every situation I faced, I secretly wondered how I would face it as a trans woman. At that point, I needed to face the real possibility that I would just have to experiment with new situations in life from the view that ciswomen do.

That was when I got out of the gay venues I was going to and back into the straight venues I had grown used to going to as a man. Of course, I found the entire process to be extremely terrifying yet natural as I settled down into my new world. A world where I did not have to worry about what my feminine instincts were telling me as I was actively acting upon them. I was free and gender for once was not getting in my way. All I had to worry about was my fear of discovery disrupting my new life.

To my surprise, most of the world around me did not seem to care there was a novice trans woman around them. No one screamed “Hey! That’s a man” when I entered the room and at the worse all I received in response was a few stares. Mostly from women. When I did, I always made sure to stand up straight and try to make eye contact if a could as if to say what is wrong with you? There is nothing wrong with me. As we all know, humans are like sharks in the water who are attracted to blood. When I showed the hard-earned confidence, I gained to project my authentic feminine self, the sharks left me alone. I can’t emphasize enough though the bumps and bruises I took to my ego to find the much-needed confidence to get by.

I did get by and stopped most all my gender battles which helped me to end all the self-destructive behavior I had carried around with me for decades. It certainly took a while for all the emotional scarring to go away and for me to clean up my act. As I always say, it was like a huge weight was lifted off my shoulders when I finally gave in to the transfeminine person I always was meant to be. And I was allowed to continue to fill out my gender workbook as I was socialized in the world of ciswomen by the small group of women friends, I had built around me. I was able to learn a little or a lot from all of them except for one. Which was my biggest issue…

In other words, the biggest boulder on my path to move was getting my male gender out of the way. He was stubborn and hung on to his male privileges as long as he could. All to no avail. I finally had to give up on trying to use all my old male strength to help me and resorted to a more feminine approach of slowly chipping away at portions of the rock. Success led to more success and before I knew it, I had a new exciting path to my future open for me ahead. It was bright, exciting and I never wanted to even think about going back.

 

 

 

 

Saturday, May 9, 2026

Graduation Season

 

Image from Logan Isbell
on UnSplash.


It is graduation season around me, and it brought up all sorts of memories of my own graduations. Many far from the usual school graduations everyone thinks about when we think about moving on with life. Plus, it goes much further than just thinking about the pretty new fashions women get to wear on their celebration days. If they choose to do it.

When I look all the way back to my high school graduation days, I always tie it with the prom season which was very close to it. My senior year was actually my second prom, but nothing really changed. I was still very envious of my date’s beautiful prom dress and corsage (which I had to buy her) to add insult to injury. No matter how hard I tried, I wanted the high heeled shoe to be on my foot and not hers and I would be taken out for the evening. Graduation was not as bad as prom because every graduate had to wear the same black gowns, hiding their new fashions until they went to an after-graduation party. But, even so, I still had misgivings about what I was facing following my graduation. As I faced hurdles such as surviving college and the military service which sometime made my gender issues pale in comparison.

Even though I realized a college graduation was in my future too, I did not think of all the other times I would have to graduate in life to survive. Examples included the times in the Army when I needed to graduate basic training all the way to making my way through the “Defense Information School” in Indianapolis. Time was flying by as I transitioned from the college world to the Army and back again three years later when I pursued my second college degree. Aside from brief moments of regression and purging, my desire to be a transfeminine person never went away and was in fact getting stronger. Little did I know I was facing more graduations confined only to how I viewed myself as a person.

Backtracking a bit and going back to my very first time I saw myself in girl’s clothes and makeup in front of a mirror. I realized I had graduated from being a so called “normal” boy forever. Plus, there would be several future gender graduations when I transitioned from being a cross-dresser to a transgender woman and when I began to take HRT or gender affirming hormones under a doctor’s care and took another major step towards my dream of being a fulltime trans woman.

By the time I had gone through all these graduations, even I would have thought I would have grown tired of the process. But I did not. I started to crave the next step in my occupation and my life as a transgender woman. Which put me on a collision course for my future. It came down to which one I would save after the major gender collision in my life. Following years and years of success, one would just have to go. Just trying to look ahead up my winding gender path became a major problem as increasingly carving out a life as a novice transfeminine person on my own terms became a priority over every thing else, I loved in my life.

At this point, my graduations began to slow down and became smaller in nature. Every time I was successful at trying to be the person I always wanted to be, I celebrated my own mini gender victory and resolved to do better on my path. No longer did I have to be envious of the ciswomen around me, since I was allowed to be behind the gender curtain. Which was another graduation for me, as I loved it. It was a major reward for all the work I put into filling out my gender workbook. As a matter of fact, it was the best graduation I had ever had in my life.  If I wanted to, I could wear the pretty dress all the other women around me were wearing.

Until then, I think I was taking all the graduations and transitions I was taking for granted. I was not raised to think anything I did was good enough, so being pleased with my progress towards my dream and being happy about it was a first for me. Ironically, I even was able to use the same restroom in the dinner club I took my second prom date to years later when it became a gay venue. It was as close as I could ever come to reliving the inadequacies I felt so long ago as I looked at myself in the women’s restroom mirror.

Humans are blessed to be able to graduate to many different levels as they transition through life. It is sad because of whatever reason, some people (men and women) are never socialized to make it to a point when they can claim the status of being a man or a woman. They are doomed to never making it past the stage of being male or female and never took the opportunity to graduate to the next level of life. They are the ones who are jealous of and hate transgender women and transgender men for reasons they do not even understand. Often, they are stuck in the past and never have the chance to escape.

If you are busy trying to figure out your next stop on your gender journey, I hope you can take the next careful step and graduate to the level you want to be. In the end, graduation is much more than having a framed certificate for your wall and who would consider having a framed certificate saying you made it to your own form of womanhood above your desk anyhow. Wouldn’t that be something?

Your destination should be your own sense of satisfaction or even happiness because you undertook one of the most difficult journeys a human can take. Congratulations!

 

 

 

 

 

 

                                       

 

Friday, May 8, 2026

Working Smarter not Harder as a Trans Girl

 

Image from Erik Mclean 
on UnSplash.



Before we get started on today’s post, here is a little background on my annual visit to the endocrinologist yesterday at the Veteran’s Administration in Dayton, Ohio.

It turns out, I was just wasting a lot of mental time and effort as I was worried about this appointment. I was worried that she would not renew my Estradiol prescription for the next year. But she did with no questions asked. The only other real problem I asked was why my Estradiol blood levels dropped as much as they did on my last visit to the vampires to have them checked. She did not know and thought I should have them checked again and see where they checked out. So, that is where we left it.

In the same vein, I had a great question from reader “Morgan” asking me if I could sense any differences in my moods when my levels went down since we both are older and on the hormonal patches. I told her no, I did not see any difference except in a new infuriating amount of hair I needed to get rid of on my arms. Since that time, the hair seems to be retreating, so hopefully that signals my levels returned to where they usually were. And, as far as moods go, normally I do feel an overall sense of wellness on the days I change my patches as well as a welcome swelling of my breasts.  I hope that covers the question Morgan, and thanks for asking.

As far as the deeper problem of feeling so much paranoia that I felt before the appointment, I think it goes back to my entire progression on the gender path I took to my transfeminine womanhood. It always seemed I was working harder not smarter as I attempted to fill out my feminine gender workbook as fast as I could. It was because I did not have the benefit all the other girls had growing up in a world of ciswomen where I was excluded. Every gender stop sign that I faced deepened my paranoia that I could ever have a chance of making it to my dream goal of crossing the male to female gender border and settling in as a successful transgender woman.

The first part I faced was just working to blend in with the ciswomen public I was around. I wanted to live the old saying that if it walked like a duck and looked like a duck, then it was a duck. My problem was even when I thought my clothes and makeup were on point and looked good, here I was walking like a circus clown in drag in my high heels. Putting my transfeminine persona into motion presented a real problem for me. It seemed like it was not so long ago that I was having the problem learning how to walk like a man out of puberty so I would not be called a sissy by the bullies and here I was trying to reverse the process. It took me a while to try to perfect my version of a woman’s unique style of movement but with a lot of practice I calmed my paranoia when I entered a room full of strangers and did the best I could. Then, I needed to work smarter, not harder trying to remember which gender I was on which day I was presenting. I worked in a pressure packed male dominated industry and it was as if the clock had been turned back and I was worried about being called a sissy again.

Another problem I was having was keeping my mind on whatever gender I was. An example would be all the time I wasted at work wondering what it would be like to live the life the ciswomen around me were living. Or better yet, daydreaming of the next time I could try when I could flip the switch and sneak out of the house again as a convincing transgender woman. If I could reclaim just a portion of the time I wasted, I worked harder not smarter as a person caught between two genders, what a relaxing, extra successful life I could have led. I was stubborn though and persisted through the decades just getting by thinking I could juggle being a parttime woman and a parttime man. Finally, it all became too much for me to handle mentally, so I needed to make a choice. But even then, I had to make certain that I was making the right decision, so I set out to change my path into a more challenging direction.

What I did was to throw caution to the wind and try to experience situations I always wondered what it would be like if I was an actual ciswoman. To do so, I had to finally earn my way behind the gender curtain and really attempt what my own unique path to trans womanhood really required of me. Essentially, the whole process required total commitment from me, and I needed to start making future decisions which would dramatically change the rest of my life. I was nearing sixty and my transgender biological clock was ticking loudly in my mind. If I was ever going to make my move to live fulltime as a woman, I better do it and it was time.

Better yet, I had a circle of women friends to help me socialize into the feminine community and I set out to secure a doctor’s approval to start HRT or gender affirming hormones. The timing was all right for my big move, and I no longer had to work harder more than smarter to do it. Most importantly, my paranoia about doing it all was at an all time low as for a change, destiny was on my side. Against all odds, I was able to meet a stable loving woman online as well as my daughter came on to accept me when I told her my deepest secret about wanting to be a woman my entire life.

Karma was coming around to pay me back for all the paranoia I experienced when I was working harder more than smarter. For the first time in my life, I allowed myself to be happy.

 

 

 

 

Wednesday, May 6, 2026

Life is Too Short to be Ordinary.

 

Image from Frolicsome Fairy
on UnSplash.



I saw this quote on a television show I watch regularly and it resonated as a transgender woman with me. Here is the quote: “Life is too short to be ordinary.”  I immediately thought that a trans woman’s or trans man’s life is anything but ordinary in the world we live in today.

I also thought of a few of the final battles I had with myself before I finally gave in to my feminine desires at the age of sixty and decided to try to enter the transfeminine world permanently. It was never a move I took lightly, which was probably one of the reasons it took me so long to make my final choice to join the girls’ club and leave the good old boys’ club behind.

What I attempted to do was weigh all the good and bad I had accomplished in my long life and use it to make my decision. To be fair, I did have many male experiences which I felt I needed to take into consideration as positives I would have to leave behind if I proceeded with my male to female feminization efforts. The end result was I found that I did not live an ordinary life for several reasons, and one of them was because I spent so much time on the gender path I obsessed about. The others involved just the ordinary life’s challenges that everyone goes through such as maintaining a family, a marriage and trying to be successful in a profession you can tolerate. I kept coming back to my gender issues which set me apart from the great majority of the world, in a good way.

Along the way, I had come to appreciate the difference between the two main binary genders by actually having the chance to live them. It occurred to me that I was having a chance very few humans have the chance to do and I should make the best of it and keep going. At the time, I was spending approximately half of my time in the world as a transgender woman anyhow, so the jump to going fulltime was becoming less and less intimidating to me.

One of the main final factors I needed to consider was how natural I felt living in each gender I was trying to maintain. After hours of thought and contemplation, I came to the realization I had never felt natural as a man. I had to struggle to make any long-lasting friends and it seemed all my accomplishments were for my public persona only. As I always say, I was never a man cross-dressing as a woman. I was a woman cross dressing as a man. From that, I realized I had always felt more comfortable as a feminine person and time was running short for me to grasp the opportunity to change for good. I was sixty at the time and it did not take a genius to realize I had lived more years than I still had to go on this earth.

Finally, it struck my stubborn head that I had been blessed to live everything but an ordinary life and I should follow my natural inclination to stay in a feminine mode. When I did, it was as if I was allowed to take a ton of rocks from my shoulders. As I assumed the life I always should have lived, I began the finishing touches of my new existence by being approved for HRT or gender affirming hormones by a doctor I read about in a local LGBTQ newspaper I saw. My body’s reaction was simple and to the point and I could hear it saying what took you so long as the changes from the hormones were so natural and immediate. In fact, the changes came so fast that I needed to move up my timeline for when I would transition completely away from my old male self.

It does not seem possible that all those gender changes were over fifteen years ago now and my world changed as positively as I ever hoped that it would. The path I took was completely personal and had its share of stop signs and blind curves but somehow, I made it. Probably because my inner self felt it was the only way to go. If working from a male background to being a transfeminine person was the way my path took me, I would gladly go along for the ride. The ride turned out to be uniquely interesting along with being extremely scary when I gave up and lost all my male privilege before I learned the essence of having female privileges.

I was fortunate that I was blessed with a healthy long life. Long enough to see the circle come around from gender darkness to light. So, you could say, my life was long enough to make it interesting and look around all those steep walls and blind curves to see what was on the other side waiting for me.

If the world would let it be, gender is just a human need on a spectrum like so many others and trans people are just trying to live their lives like so many others. And I know gender is much more than a black and white reality to all of us. You can view yourself anywhere from a weekend cross-dresser all the way to a post-op woman and all should be accepted under our complex umbrella of people. It’s just another way we are far from ordinary and difficult for the average person to understand. It is also difficult to explain to a loved one when we do not fully understand what is going on ourselves, which often takes a long time to happen.

Rest assured that even if your life may be different and/or difficult at times, I will be far from ordinary.

Thank you all for your comments, claps and new subscriptions! Without all of you, none of what I try to pass along would be worth it.

 

 

 

Monday, May 4, 2026

Pressure Tested as a Trans Woman

 

Image from Jayson Hendrickson
on UnSplash. 

As I moved along in life, I became pressure tested on both sides of the gender border.

On the male side, I became embroiled with restaurant jobs which involved immense amounts of pressure to succeed and on my female side, I felt the same pressure to succeed when I was finally able to leave my mirror and enter the world. For the most part succeeding as a male meant more financial rewards, while the success as a transfeminine person meant more inner freedom to express myself.

Ironically, my success as a novice cross-dresser or transgender woman often came at the expense of my male self when he failed at a project in life and came running back to dresses and makeup for comfort. Even that became old though when my trans woman kept increasing the stakes in the basic battle to just be seen in public. She wanted more than the easy trips to women’s clothing stores where money was more important than gender. As she began to interact more completely in the world, the pressure to be tested time and time again increased dramatically. Especially when she had to do more than try to communicate with more than a simple “Hello” or “Thank You.” For the longest time, I was panicked and very insecure about holding any sort of a conversation with another person, woman or man.

The way I relieved the pressure of communication was simply tied to doing it over and over again until it became as natural to me as possible. I learned from my feminine vocal lessons, it was not as much about what you were saying as how you were saying it. And how I could interject little feminine vocal patterns into my speech, even though I still had a deeper voice than most women. I say most women because I immediately began to notice a few ciswomen who had lower voices but still managed to communicate in the world with no problems. All because they had the benefit of growing up around other women. As I said, the only way around my communication potential problem was to hitch up my big girl panties and begin to communicate with the world. Which in some cases was one of the last frontiers I needed to face as I climbed out of my mirror and into the world as a trans woman.

I discovered I did not really know any pressure on my initial excursions as a feminine person until the time came to use the restroom. Initially, I was very intimidated and made sure I waited until “the room” was empty before I snuck in to use it until I began to build some confidence in myself. When I did, I began to learn restroom basics such as making sure I took the time to smile and interact with any other women I may encounter. The exact opposite than what I was used to in any men’s room I used. Since I was not using the women’s room as any sort of a fun test just to prove I could, I needed to learn as much as I could about other women because of a natural need to do so. I did things such as trying to mimic the sound of “flow” when I went to the woman close in the stall next to me and of course, I needed to remember to look for toilet paper, hang my purse up and always, always stop to wash my hands as I examined my hair and makeup in the mirror. No matter how much of a hurry I was to get out of there.

Surviving the restroom wars gave me the confidence to lose some of the pressure I felt as I entered the world for the first time as a transgender woman. From there I could move on to bigger and better things such as being recognized as a regular in the selected venues I wanted to go to. When I did, I knew I would have the backing of the staff if and when I was approached by a gender bigot or TERF (ciswoman bigot) about what I was doing there at all. In fact, I think I became the token trans woman at several venues who were proud of their diversity and safely for the LGBTQ community.

If I was a more intelligent person in math, maybe I could come up with a quotient relating to how pressure relates to confidence, but I cannot. I am stuck just trying to explain what it meant to me and what it might mean to you if you are considering a gender journey such as mine. The easiest way to describe it is that it is an intensely personal journey that is often lonely and full of self-sacrifice. Which could also describe why the path or journey is so full of pressure to succeed in so many different ways. I say that because I learned on my path that there were so many different ways to achieve my dream of living the way I wanted to as a fully functional transfeminine person. Primarily I learned I did not have to be the most attractive woman in the room to be accepted. Maybe I could make it on my personality. Which is exactly what many ciswomen do.

When the pressure was off, the pleasure set in for me and I could begin to refine who I wanted to be as I pursued a rare second chance in life to rebuild myself in the image I had always dreamed of. I was fortunate when I found the right people, cis women, to help me along in ways they never knew as I filled out the little nuances of my gender workbook. As I always say, I had no idea of how many layers women have to go through other than men just to live their life.

I don’t think I had a choice in my life to not live the pressurized existence that I lived. It was all built into the path I chose to take, and I grew used to it. As a transgender woman, often it seemed I had more than my fair share of pressure to deal with. That is why as a tribe, trans women and trans men have proved to be very resilient over the time we have populated the world. Regardless of what haters and bigots think.

 

 

Sunday, May 3, 2026

My Last Date as a Man

 

JJ Hart in the long black wig
I wore to the concert. 

My last date as a man
was very eventful as destiny was sending me a powerful message.

It all began a couple of years after my second wife passed away and I decided to again seek out feminine companionship from a ciswoman. Then I made a mistake and became enamored with the mom of one of my servers at the restaurant I owned. Mom was about my age and extremely attractive and I gathered up the courage to ask her out when I learned she was single. From there we went on several dates including one in her native Cincinnati. I was quite naïve and thought things were going fairly well until my daughter got me two tickets to a “Joe Cocker” concert at an outside summer festival near to where she lived in Dayton, Ohio.

I guess the idea of perhaps meeting my daughter scared her off, because after initially saying yes, a week before the concert she abruptly said no and I wasn’t to call her anymore. By this time in my life, I don’t think anything could surprise or hurt me more than what I was already going through, so I picked up the pieces of this brief ill-fated relationship and prepared myself to move on. But I had one problem, what was I going to do with the other ticket I had for the concert. Then my mind came up with a plan, why not invite my feminine self? It would be yet another test to see how successful my transition was coming along as well as soothing the ego wounds from being turned down by what turned out to be the last date I would ever have as a man with a ciswoman in my life.

At that point, I was very much still in the closet to my daughter, so I planned to pick up the tickets as my male self then go home later and get ready. Getting ready proved to be an adventure as I knew I could put together an upscale/casual outfit for the evening. I ended up choosing a black outfit with a three-quarter sleeve mesh top and wide legged silky black pants with black sandals. Topping it all off, I chose my long black straight-haired wig and sunglasses on my head as an accessory. After carefully applying my makeup, I was ready to take on the world as a transgender woman out to her first concert. I felt good and confident for a change as I left the house for the half hour drive to the concert venue.

Once I arrived, I gathered myself, checked my makeup and took off walking to the concert which was filling up with people fast. Since it was still light outside, I could wear my sunglasses to check out anyone who was staring at me without them knowing. I was relieved when no one noticed the tall, long-haired woman in black making her way through the crowded sidewalk to her seat. I even had enough time to walk up to the concession stand and order me a refreshing drink before the late “Joe Cocker” started his show. By this time in his career, he played his hits and I was happy.

I ended up immensely enjoying the concert. Even more so since I was spending unique public time with my transfeminine self. I walked away from the experience with a new-found confidence in myself to live my life the way I had always dreamed of. In a world where ciswomen ruled. And maybe most importantly, I don’t think I embarrassed myself by the way I looked.

Maybe I was a little too over dramatic when I mentioned destiny setting in that night, but it did because never again did I set out to date a ciswoman as my male self and go through all the dating contortions I hated so much. I don’t know why but I always had felt so much more at ease when I was dealing with women as a trans woman and I never looked back.

My last date as a man was uneventful because it never happened it seemed for a reason. In the future I was able to have much better times going to places such as roller derbies with my lesbian friends where I could relax and have fun. Something I rarely did when I was trying to date as a man.

 

 

Saturday, May 2, 2026

The Last Line of Defense

 

Image from Gayatri Malthroa 
on UnSplash.

Throughout nearly half of a century, my male self-fought the complete transition I made into a feminine lifestyle.

During that extended period of time, I think I tried everything possible to convince myself that I was wrong to want to play in the girls’ sandbox at all. As I mentioned in yesterday’s post, I “purged” many times of my feminine belongings. Leaving me with nothing but my most cherished pieces of girl’s/woman’s clothing and makeup. The makeup was easy because I knew I could always buy more. Perhaps the most precious items I never threw away were the nice wigs I was able to buy and the silicone breast forms which ironically were given to me by a fellow cross dresser who was purging also. Deep down inside, I knew I would need the wigs and breast forms again when my urge to cross-dress returned. As my own personal history told me it would.

It turned out that purging was not my last defense, no matter how hard I tried. In fact, the more I tried not to be feminine in any way shape or form, it seemed I slipped closer and closer to it. Especially when I learned I could dress to blend with most of the ciswomen around me. It was then I learned how natural I felt when I began to get it right and could feel all the gender euphoria I could feel.

What I did continually feel was my masculinity slipping away and I only used it on occasions with my wife in mixed company and when I was working in a high-pressure environment. For years, when I was out in the world experimenting living a new life, I felt as if I was sliding down a steep hill towards a transgender cliff which I had no idea of how I would be able to land.

In all fairness to my second wife, she never opposed me cross-dressing and knew about it when we got married. But on the other hand, completely opposed any idea of me becoming a transfeminine person. Between her and my male self, they made formidable opponents in my life when I thought about living as a trans woman. What made it all worse was when my wife kept saying she did not want to live with another woman and did not agree to that when we got married and I had to agree with her. Putting me in a very difficult situation in my life. I escaped the best I could by sneaking out of the house behind her back at any given time I found to test the world time and again to see if I would be allowed to go back behind the gender curtain. Which in many ways, represented escaping the last defense to staying in the male world I had.

Of course, my wife found out on numerous occasions what I was doing as a trans woman and resisted all my progress. When she did, we had giant battles which she normally won and I tried the therapy route to help me with my gender issues. Therapy helped me in many ways in my life but not so much with my deep-seated gender issues. I was expecting too much when one therapist told me if I thought our sessions would ever relieve my tensions, I would be wrong until I was able to make the final decision on if I was able to be a woman or not. At that point, I had two of the most far-reaching quotes that I ignored which were told to me. One of which was the time I was told I was the only one who could decide my gender future and the second was when my wife told me to go ahead and be man enough to be a woman. I was so sure I could do it my way and it cost me dearly. Especially, in terms of my overall mental health when juggling two genders and two lives at once became too much to handle. I did not know if I was coming or going on which day it was on how I was expected to act.

As many of you know, my second wife tragically died of a massive heart attack, leaving me with only my male self to do gender battle with. His last defenses deteriorated quickly as I became deeply unhappy and lonely and took solace in my inner female self for comfort. She stepped up big time, and very soon when I was not working nights, I was in one of my regular drinking venues seeking company. That was when I discovered I had more in common with the lesbians I met than with any man. Since most of them rejected me anyhow for leaving the good old boys club. I was able to say good riddance and go forward in my life into a world I never thought possible could ever be a part of. I had never really got along well with men in my life, and it turned out nothing had really changed. Except the way I was exploring the world. Finally, as my true self. As I was finding me after all those years of searching.

The last defense my male self-had was when my third wife Liz and only daughter came to my rescue with unwavering support for my final dive off the steep gender cliff. They made the landing very soft, and even easy. More precisely, Liz made me a believer in myself again and my daughter gave me support I needed from what blood family I had left since my brother rejected me, and my parents had long since passed away. Add in the couple of lesbians I always socialized with and I had all the support I needed to succeed in where I had dreamed of going and being accepted behind the gender curtain.

By far, I would be remiss if I did not mention the power of HRT or gender affirming hormones in removing any of the final defenses my male self-had going for him. I could not believe how fast the hormones acted as my body began to change, inside and out. It would take a whole post to describe all the impacts the hormones made to me. In fact, I have my annual appointment with my endocrinologist coming up this week, and with it, the chance to get refills on my hormonal patches.

Maybe I can thank her then for helping me to win my battle with my male self. Since I receive my HRT meds through the Veterans Administration, I always hope nothing changes from the top down with my ability to keep receiving a huge part of what makes me whole. I worked too long to get here.

Thanks again for joining me on my journey and I hope my experiences help you too.

Any comments, claps or subscriptions are welcome and make my work so worthwhile!

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Friday, May 1, 2026

No Laughing Matter

 

Image from Priscilla Du Preeze
on UnSplash. 

I am always amused when someone thinks I had a choice to follow my transgender path. Obviously, they were not there for all the trials and tribulations I had and the extreme harassment I received as I came out into the world. All the times I hurried home crying when I was stared at or glared at by the public before I was able to improve my feminine presentation to the point where I could blend in.

I did all I could to improve my testosterone damaged body by going on a crash diet and did my best to improve my skin by using moisturizers everyday after I shaved before I went to work. Why would I attempt all of that if I thought crossing the gender border was just a choice I could make. The farther I went, the more I had to do to improve. Mainly because it felt like it was the right thing to do.

Perhaps the most important sacrifice I needed to be prepared to make was losing my white male entitlements or male privileges. Even though I did not respect the growing rights that I had obtained through hard work as a male, I needed to keep in mind continually I did not really want them anyhow and there were better days ahead if I ever had achieved my dream of living as a transgender woman fulltime.

Through it all though, I wondered why all this gender turmoil was happening to me. Often when the poor, poor pitiful me aspect of my life was at it’s worse, I would “man-up” and purge myself of most of my feminine belongings. As most of us know, purging does not work for any length of time. All it did for me was make me go out and buy more makeup, clothes and shoes to express my femininity again. A total waste of money, but at least I always tried to build back better following every purge I tried. Finally, I looked back at purging as just another rite of passage I needed to through as I followed along my gender path to success, and I was able to put my transgender victim mentality behind me.

As I grew older and set in my cross-dressing ways, I knew increasingly I had no choice in how I lived my life. I was rapidly going through yet another gender transition from just having a so-called hobby into being a transgender woman. I was doing more than just shopping for more and more clothes and was trying out new ways to experience the world the way ciswomen do. I started doing a portion of the grocery shopping successfully as the new transfeminine me all the way to starting to do all my Christmas shopping in unique situations also. Just to see if I could.

At that point, the things I needed to go through to survive in life became increasingly evident to me. I would need to express myself as a woman and I had no choice but to do it. I also knew the risk I was taking when I thought about losing the male life, I had worked so hard and long to be successful at. What would my daughter think of her new dad was one of the few variables as I knew I would lose my long-term marriage and great job that I had. I needed to know beyond a shadow of a doubt I was doing the right thing, and I truly had no choice but to stay on the course I was on. This is where my transgender humor comes in. Why would anyone ever put themselves through such a life full of turmoil if they ever had a choice. Or, when just putting on a dress becomes so much more than a fun experience, where do you go then?

It is no secret where I went and I had the chance to experience so much more in my life because it is exceedingly rare when a human gets the chance to experience both sides of the binary gender spectrum. The problem is we transgender women and transgender men don’t have a chance to enjoy the trip because of the pressure we put on ourselves to perform behind the gender curtain we chose. If we are not doing it to ourselves, the pressure is certainly on from the public to do it too. Especially these days with the charged anti-transgender political attitude we are seeing from the orange menace in Washington DC, and in many states such as my own native Ohio.

If we can ever get the public at large to understand we trans people never had a choice on the life’s direction we ultimately took, we would come out so much further ahead. Sadly, the path to get there does not seem to be getting any closer for many of us as the things we have to go through just keep on coming. I know for those of you who are still on your transition path or even consider it, it is a major step to take. Hopefully on the way, you can take the time to stop for a moment and enjoy how far you have come. I always thought if it does not kill me, it will just make me stronger would help me along. And on a lesser scale, the old sticks and stones may break my bones, but words can never hurt me saying really applied to me also.

When you are on your path long enough to realize there is no turning back, you will also know you had no choice but to keep going towards your goal. It was never easy, but so worthwhile as you navigated the final blind curves, potholes and stop signs. At the least, you will know you lived a life where you had a choice and made the most of it.

Plus, certainly it was no laughing matter. 

As always, thank you for reading along with my experiences. Any comments, extra claps or subscriptions are welcome!

 

 

 

 

Chance versus Choice as a Trans Girl

  Image from Brooke Ballentine on UnSplash . Chance versus choice for a transgender woman or transgender man can cover a wide spectrum of ...