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

Tuesday, January 20, 2026

Her Way or the Highway

 

Image from Joshua Rondeau
on UnSplash. 

Very early on, it became evident to me that my feminine self was very demanding. Who knows, maybe she took after my mom who had to be strong in a very male dominated family.

Wherever it came from, I always felt a strong push from her to be let out into the world to live. Even so she would have to wait years and go through constant trials and tribulations to do it. The gender journey I was on proved to be much longer and challenging than either of her competing souls thought possible. Nearly a half a century of trying before I got it right.

To make matters worse, my male self never was one to give up easily and he fought every move intensely along the way. Making everything even worse was that he was fairly successful in carving out a life he never really wanted as a man. The more baggage he accumulated, the more difficult it became leaving it all behind in a male to female transition situation.

Even more stressful was the fear of the unknown which followed me everywhere. It started with the feelings of not knowing if I was a boy or a girl when I was growing up and continued onward from there. Seeking gender answers always took a lot of energy out of my life that I wished I could get back. Of course, that was impossible and I needed to learn to live with the way I was with my gender dysphoria until I hoped I could do something about it. What I did do was get out of my closet/mirror and began to see what the world would be like for a transgender woman like me. Would it be her way or the highway after all. Following a rough start with my public presentation, I lost nearly fifty pounds of weight and began to perfect my art of makeup. I put a tremendous amount of work into my feminine presentation, more than anything else I had ever done in my life.

As it turned out, all my effort was rewarded and my transfeminine self-began to emerge and live her life. The days of just going out to be alone in the world subsided as I was able to make new social contacts for the first time as a trans woman. For the first time in my life, the gender teeter-totter I was on began to favor my feminine side which proved to be a real problem for my male side who still was working fulltime in the world and bringing home a good income. I was actually ahead of my timetable in how I wanted to work out the gender issues in my life and increasingly it was becoming her way or the highway when it came to my life.

The pressure to change became enormous and wrecked my mental health leading me to alcohol abuse along with self-harm (suicide) attempts. I drove too fast and took too many chances hoping something would come along and put me out of my misery. Nothing ever did until I realized the answer was screaming at me all along. I should have never been born into the male world that I was and now would have to overcome the testosterone poisoned past I had lived to do something about it.

Her way became a real reality to me when my second wife passed away unexpectedly from a massive heart attack at the age of fifty. I was so disappointed that she never did anything about her health until it was too late that I never properly grieved the loss of someone I had been married to for twenty-five years. Instead, I turned to the waiting arms of my feminine self for comfort in my times of severe despair and loneliness. She was all I had as I sleepwalked through my life, and her highway began to look better and better. My new timetable of a possible jump across the gender border dramatically increased when suddenly the greatest barrier to stopping my leap had been taken away.

Before I knew it, the new highway I had dreamed about living on was upon me and it was fast and smooth since I had worked through most all of the bumps and potholes earlier than I had experimented. For once, I was not frustrated with all the time it took me to make my final gender transition decision. I always compared the road I was on to the Autobahns I drove when I was in Germany which were always well maintained and built for high speed. I even had to be careful that I was not going too fast as I had to figure out who was left to talk about my authentic self. My daughter came first, which went exceedingly well and then my brother which went exceedingly bad. Then I moved on to what was left of the very few friends I had left or just began to not see them anymore as I built my new life.

I am very glad now that it was her way or the highway in my life. She kept telling me it was the way life should have always been and the brief moments of life I saw which were so fluid and natural were only the beginning. Maybe I had been too cautious for my own good when I tried to take the back roads towards becoming a full-fledged transgender woman, but it was the only way I knew. Hiding who I was started so early in life, I never saw my way out of it for so many years until it was too late. I was stuck in a habit I could not get out of. Until I woke up to the fact that her way or the highway was a realistic path my life should take. I have enjoyed the highway ever since.

I was more like my mom than she ever knew.

 

Saturday, January 17, 2026

No One Way is Correct

 

Image from Gabor Kaputi
on UnSplash. 

Even though we transgender women and trans men often follow similar gender paths to get to our goals or dreams, it is still true that one path (the one you are on) is the only correct one. Plus, don’t forget there are so many side trips to take such as surgeries and hormones to help us along.

For example, I read about and hear from other transgender women who have elected to undergo major and costly gender surgeries (like Amber) which they deeply feel they need to feel whole, while me, on the other hand have decided to steer clear of any surgeries. Mainly because they don’t define me as a trans woman. I know what my brain is telling me gender-wise and just don’t need the corresponding equipment between my legs to improve my overall being. Although let me say I understand why somebody else would and if I was younger, I might have considered the surgical route. It just took me too long to figure out who the true me was.

Other than surgeries, I took the same path as many of you. I experimented with my mom’s clothes and makeup since I did not have any sisters, all the way to service in the military from those of you who are approximately the same age as I am such as Bobbie W. who even served on her version of the American Forces Radio and Television service as I did, although she was in the Navy. It amazes me how small the world has become because of the internet that many of us did not have in our formative cross-dressing years. Besides Bobbie, over the years, it has amazed me how similar some of our paths have been and it would not have surprised me if we had not met along the way. Except if you were like me, you were desperately attempting to hide your true self from everyone else in the world.

Then there were the evenings when I did see another transgender woman in one of the venues, I was a regular in, other than Racquel who was a trans friend of mine. One in particular was at a TGIF Fridays I went to quite a bit. I watched this well-dressed large woman step up to the bar and order a red wine, then before I could even attempt to introduce myself, she was gone and I never saw her again. So, on that occasion, I did have my path crossed by another transfeminine person since I could not attach a label to her such as a very accomplished cross dresser. Outside of a few “women” I saw shopping in the grocery store over the years, I learned how rare our tribe really is.

One of the reasons we are so rare is that all of those still in the closet due to their gender issues have not had the chance to be out and be counted. Mainly because of all the male baggage they have fears of losing. It is terrifying to think of losing baggage such as spouses, family, friends and jobs to name a few of the bigger ones. At least it was for me as I went through life frustrated with the amount of male baggage I was accumulating.

Even though, when I started blogging years ago to pay forward and help others similar to me in the closet, it occurred to me my plan had backfired to an extent, and I became a role model to some of my readers. Some even wrote in and called me some sort of a hero to them which humbled me because I never set out to do anything like that as I was just trying to live my life the best I could. Writing about my life was Now adays I keep trying to say I am no hero but merely someone who was terrified to leave her closet and live in the world as I knew it. Certainly not a hero by any sense of the word.

Recently, another point that I have been trying to make is there is no right way to achieve leaving your closet and living an authentic feminine life. Sure, it takes a lot of work and effort to achieve doing something the greatest majority of humans have never considered trying. Especially when we live in a negative atmosphere where a certain melon felon and his political party are trying to demonize us. Hopefully, that all will stop happening when the population finally tires of us and seizes the opportunity to vote on the real issues. Which makes it so important that even if you are in your closet, you vote your true conscience this coming midterm. So much for my political rant which is urging you all to get on the right gender path and stay there through the elections and beyond.

In the meantime, always hope for the best when you are out as your authentic transgender self. Your confidence will keep many of the middle of the road haters and bigots away because humans are like sharks, they sense blood in the water. How you get there is determined by many factors, but the main one is you can only gain confidence by going out into the world in your heels and doing it. Other than that, a disarming smile will take you a long way too. Keep in mind that most people don’t care about you, they are only concerned about themselves, and you will be ok.

As you do it, don’t worry about making the big mistake and you will be much freer to be you. You are on the right gender path because you are on it. Sure, it will have many curves and roadblocks but sometimes all of them make the journey much more worth it.

 

 

Friday, January 16, 2026

You being You or Playing up Being Different as a Transgender Woman

JJ Hart
At first glance, the statement of what makes you, you, seems like an easy one to answer. Especially if you are not transgender. Because you are in the majority and not perceived as being different.

For cisgender women or men, lives are set up to be lived in a certain pattern from birth till death. Using a baseball reference, life throws you a real curve ball when you are trans. Because you are different and often pay the price. The sad part is, for the longest time, we have such a hard time explaining to others our gender issues when we don’t understand them ourselves. In my case, it took me years to come to the conclusion I was not a man cross dressing as a woman, I was a woman cross dressing as a man, and I was not stuck with some sort of a weak excuse such as I was a woman stuck in a man’s body.

I grew up in a semi-dysfunctional family which valued being different. Until it infringed on what mom and dad thought was right. So having their oldest son want to be their daughter would never have been accepted. Or that was way too different for them to understand. I basically went on with my life knowing I was different and not knowing the information I needed to know if anyone else felt the same way.

Before I knew it, I was on the path to male privilege if I just did my best to earn it. The only problem was, I did not want to be on it. It was as if some invisible force was keeping me there against my will. Sometimes, it was easier not to expend my energy fighting my gender issues than to actually begin to leave my mirror and seek out attention in the world. It was only then did I begin to learn if my transgender dreams could ever become a reality or would forever remain a dream until I die. I just knew, both of my parents had lived relatively long lives so I should have time enough to do what I wanted.

In the meantime, I did what was expected of me. Such as reproducing an offspring daughter, earning two college degrees and serving my country in the military. I was not different than many of the other men around me, and life was a blur during this time. The worst part was, I was still not coming any closer to learning if I had any possibility of living my transgender dreams other than the occasional Halloween party. I was still paranoid that others around me would learn of my gender difference and often I would wake up in the morning wondering if I was a man or a woman. Which certainly set my day off on the wrong foot and I am not even adding in the vivid dreams I was having when I was a pretty woman. It would often take me hours to fully return to the disappointing relationship I had with my life as a man.

All the relationship did was continue to cement my unwanted claim of being a semi-successful man. I often wonder what I could have accomplished if I could have given my male self the full attention he sometimes deserved. Not the partial attention he received when I was inwardly thinking of what my life would be like if I could live it as a transfeminine person. It was as if something was telling me to put the brakes on acquiring any extra baggage as a man that I would have to get rid of when and if I was able to transition from male to female. It turned out, the learning curve I went through as a male helped me anyhow as a transwoman, because I was a stronger person. Which really came in handy on those lonely nights when I was out trying to be myself and not the self that made me different.

It was not until I made my gender differences an accepted part of me did I begin to experience success with finding new friends in the world. Since I could not deny what I was, why not utilize me to make me more attractive and I don’t mean in the physical sense. I was like other cisgender women who may not be the most attractive woman in the room but there was something about them which set them apart with their inner glow. I knew if I could harness my inner glow, I could go much farther in life and dispel for good that there was any dreaming left for me to do.

Literally without thinking about it I had crossed the line and transitioned again. I had went from being a serious cross dresser all the way to being a transgender woman and then to being just me. I had spent all the time around the cisgender women that I knew for them to accept me as an equal behind the gender curtain and I did not have to feel any different any longer. I did not have to seek out a mirror to reinforce in my mind who I was. I had sorted my male baggage and kept what I wanted and discarded the rest, so I was ready for my next big challenge which was being approved for gender affirming hormones or HRT. When my body took to them so naturally, I was able to take another big step towards doing away with what made me different from other ciswomen around me. In fact, I wondered what hormones some of the mean women I knew were on. They must have had an overdose of testosterone somehow in their diet.

While it is often difficult to emphasize the differences which make you different as a transgender woman or trans man in today's world, your differences can still be a positive influence when someone gets to know the real you.

 

  


Tuesday, January 13, 2026

Following your North Star

 

Image from Heidi Fin 
on UnSplash. 

I define my own personal “North Star” as the basic direction I had to go to be truthful to myself. Many times, I found how valuable my star was when I was lost in my own transgender woods and couldn’t see the forest for the trees.

Along my path, there were many times I lost sight of my North Star and needed to regain it before I could continue. As I did, I spent many a very dark night searching for my life’s truth of wanting to shed my male existence for a feminine one. I would not recommend what I went through to anyone because it was a long, lonely journey. Even still, I was fortunate in that I seemed to always have just the right amount of gender euphoria to propel me forward. It did not matter if I was just gazing at my image in the mirror and thinking I was a pretty girl, or shopping for groceries in our local market, something possibly positive came along for me to see my star and wondered if it was still within reach.

Sometimes, life was cruel and dealt me roadblocks which kept me from following my dreams such as the unplanned birth of my daughter. Which turned out to be the best thing that ever happened to me in my life. At the time of her birth in 1976 I was very much out of control and needed something to ground me. Much more than the excessive amount of alcohol I was drinking at the time. All the beer did was help me to lose sight of my North Star until I could regroup and find it. I did not learn until much later how alcohol was a depressant and did not mix well with my already depressed personality. Even though I was dazzled by the miracle of birth and the rapid growth into a little person by my daughter, life was still not good as I was sliding by in a haze most of the time and losing track once again of my North Star.

Somehow, I was able to emerge from this part of my life on my feet and ready to search for my truth again. But not enough to accept what I was finding. Even though that bright light of a transfeminine existence seemed close enough for me to reach out and grab it, I just kept denying its existence and taking the route of least resistance and was existing the best I could as a part-time cross-dresser.

When I changed professions and entered the professional restaurant business, I developed a love/hate relationship with what I was doing. I loved the extra money and advancement it brought me but hated the hours and extra pressure the job brought with it. I guess the good part also was that the new profession cleared the way for me to reset my existence and locate my North Star again.

Once I located my star, I had to finally face the reality of where it was leading me. Gone were the evenings or days of going out into the world thinking I was nothing more than an innocent man trying to look like a cisgender woman. In, was a new reality that I wanted much more than to look like a woman. I was a woman and needed to see if I could live my truth, I knew all along but refused to face. Even though I was terrified of doing it, I was advancing down my gender path, and the skies were clear so I could see my star and have an idea of where I wanted to go. Better yet, once I was passing my gender mileposts of very much socializing with cisgender women as an equal in my mind, there was no going back.

As I did it, I made certain I was trying to cover all my basics such as what I would do to live in a new transgender world I dreamed of and in reality, had never seen. Such as how I would support myself because I knew my current male job would never support a mid-gender stream male to female transition. At that time, I was still several years away from an early Social Security retirement, so I needed to be careful of what I decided to do. What I decided on was a low impact non pressure job I could work just to get by for the time I needed until I retired. I found that was impossible and I had to backtrack into fast food again and work a job I hated until I could quit and pursue my star.

By this time, I had paid a lot of dues playing in the girls’ sandbox and I had a very good idea of what I was facing if I went full time into a transgender world. I don’t think it is possible to ever capture your North Star, but I do think you can come close to living it. There are many paths to get there, and no one is right. Some transition on their own while others have help like I did. I was always a social critter, and my process happened to work for me but yours could be different. Plus, destiny can often alter your path to following your personal star. Do not panic until you find it again and revive your journey.

Remember, you are in uncharted gender territory, often without a compass. When it happens to you, you need to just hitch up your big girl panties and do it.

 

 

 

Monday, January 12, 2026

Who Won the War

 

I call this a fake image of me.
Pre Hormonal padding and hair.

Relax, this post is not another of my political rants!

As my life enters its senior stages, I have the luxury of looking back and wondering what the hell happened. Or, who won the gender battles and who ultimately won the war.

Even though the cards were stacked against her to start (and continued for years), my feminine side managed to hold her own enough to survive. Which was amazing when I looked at the beginnings of our life and what she had to put up with. To start with, I was born into a very male dominated family with a highly competitive nature to contend with, so I always had to be ready for a battle of some sort. For the longest time, I would have to accept defeat at the hands of my brother who was always the better athlete and I would quickly run and hide behind my dresses and makeup. When I did, my feelings were soothed and I was ready to try to compete and win.

One way or another, I found the only winning I was doing was when I was a girl in front of the mirror. The mirror kept telling me I was pretty, and that kept me going. I was far from winning any gender war within myself, but I was managing to tread water and stay afloat…barely because I had no where else to turn. My desire to be a girl was shutting me off from the world. What happened then was, I grew tired of just presenting in front of the mirror and wanted to test how well I did in front of the world. The whole scenario forced me into major battles once again.

This time, I found amazingly I could compete in the world as a transgender woman and I did not have to accept defeat every time I went out in public. Maybe I was finding my home gender after all. I think at this time too, I was battle hardened from all the defeats I had sustained in my male life, and it was easier for me to continue to move forward.

As life started to change, I wanted to explore the consequences of what I was doing more and more. Then my battles became more serious and far reaching which led my male self and my second wife to panic. They suddenly realized I was becoming a more accomplished trans woman and could possibly make it after all to my dream of living a full-time life as a transfeminine person. For her part, my wife kept telling me I made a terrible woman, which I learned later was true. Simply because I had not spent enough time behind the gender curtain to claim my womanhood, yet, but I was coming alarmingly close enough to find out what she was talking about to set her alarms off. And my male self, not to be outdone was doing his part too by relaying all the new jobs and moves he was making into a personal success story.

Between the two of them, they made formidable gender foes, and I needed to become better at exploring who I really was. Whenever I could get off work, I attended cross dresser-transgender mixers, both large and small to determine if I could do what I saw other successful people living on the gender frontier. By doing so I could see my major battle lines being drawn up ahead, and I was like a runaway train headed for them. Major decisions were coming up in my life if I like them or not because I had spent too much time and effort in my explorations to turn tail and run again. I had nowhere to go this time because I had blocked all my exits. All my skirts, dresses, heels and makeup were ready for action.

By this time, my male self was in pure panic mode knowing that his ace card of military service had backfired on him. He thought somehow an ultra-macho experience that Army infantry basic training would make me more of a man when in fact, the whole experience made me a stronger person and believer in myself. When push came to shove and the times were darkest, I could make a decision and live with it. Even if was the decision that would effectively be his final battle and win the war for his feminine counterpart.

Also, I was coming up with a clearer idea of why I had struggled with who I truly was for all those years. I had blindly followed the idea that I was a man cross dressing as a parttime woman when, in fact, I was a woman cross dressing as a parttime man who happened to be married to a strong ciswoman. Plus, he was the primary wage earner in the family. Covering all those gender tracks was exceedingly difficult and put a tremendous strain on his mental health but he kept on fighting the gender battles against all odds. Out of some misguided idea that he had to. It was such a relief when he surrendered and gave up the remainder of his clothes to a local thrift store. The only thing he saved was his Army uniform which had taught me so much about life and winning,

When he realized he had lost, there was no time for wild celebrations. Only time for serious contemplation of what was next and how my victorious trans woman would react. It turned out, she took her win quietly and set out to build a life she always knew was possible. A life which was enhanced even further when she was approved for therapy and HRT through the Veterans Administration. Finally, she had the help she needed to match her internal needs with her external appearance. Which is the subject for another blog post altogether.

Regardless, victory was sweet as my old male self-faded into the past. She lost many battles, but ultimately won the war.

 


Monday, January 5, 2026

What was Meant to be, Will Be

 

JJ Hart doing Trans Outreach program.

The longer I lived and experienced a feminine based experience, the more I realized my life was turning into what I always expected it to be.

Yesterday, I spoke about the “aha” moment I had when I transitioned from being a serious cross dresser to living as a novice transgender woman. Even though I was scared to death to do it, after the experience was over, I felt so extremely natural I knew my life would never be the same again. In other words, my new life as a trans woman was always meant to be and felt like it. Over the years of thinking about my new life and seeking answers, the only excuse I could find was that my mom had several still births before me and resorted to the new (at the time) DES drug which was prescribed to help problem pregnancies. DES was known to flood the uterus with estrogen to help the birth mother and was “rumored” to be a cause of gender dysphoria in children later in life. But all of that was just a theory.

I was left to be on my own forever wondering why I felt so natural when I tried to cross that gender border into womanhood. As my mind wandered into all the different scenarios I could have been confronted with, nothing was ever placed in concrete. As much as I disliked competing in the male culture, still I was relatively successful in doing it and had managed to carve out a life in a gender I wanted nothing to do with. So, it was not that.

The older I became, and the more experience I forced my way into, the more I felt living in a cisgender women’s world was the place for me. If I could make it happen. First, I needed to get past my appearance paranoia/obsession and open my eyes to what was really going on around me in the world when I was exploring it as a transfeminine person. I was naïve in my gender thinking about women as a whole and tended to put them all up on a pedestal. Which I found out was completely wrong.  Quickly I learned that although women operate on different wave lengths as men, almost all the basics were still there for me to learn. At that point, I had plenty of other “aha” moments when I realized the intricacies of how the two main binary genders operated on a daily basis.

I learned too that there were simply some things I could not do by simply observing the ciswomen around me, I needed to interact with them before they would let their guard down and let me see their true selves. The more immersed I became in their culture, the more I wanted to be and again for the first time in my life I began to feel natural in my own skin and felt like my life was meant to be.

I found I was a quick learner when it came to being a quality trans woman and not a standoffish bitchy one. I learned I could make friends easily with most all other women and the rest did not matter anyhow.  Most of them were evil in their own ways, and I did not need their problems if I was ever going to get where I was trying to be. I had bigger issues to face such as how I could learn to communicate effectively as my new, out, authentic self who I learned could not wait for her chance in the real world. She knew exactly who she wanted to be if she ever got the chance. All of a sudden, I was having fun in my life again and the male to female transition problems I was experiencing began to fade into my past. Even though I carried an immense amount of baggage with me from my male life, I was still able to pick and choose what I always wanted to remember from the male world I came from.

If I paid attention to the knowledge, I had gained from having experience on both sides of the gender border, it gave me a real head start on how to conduct myself around men and women. I even was asked questions from women about how to deal with their man and how he may be feeling and I was very flattered to have tried to help.

As I always bring up, my biggest problem with all of my gender transition was how long it took me to do it. Waiting until the coast was clear and when I was nearly sixty years old took away valuable years of my feminine life which I could have experienced more of the world. If I had it all to do over again, I would have been braver and known the huge gender move I was about to make was always meant to be, so just do it. Pull the bandage off my old male life and get on to the future.

Maybe, if I ever have a tombstone, I can have it engraved with the simple words, “She was always meant to be.”

Monday, December 29, 2025

Dark Side of the Gender Moon

 

Image from Maria Kovalets
on UnSplash.

Exploring the dark side of the gender moon for me meant a lot of work.

I equate it to the first times I could experience wearing my own hair in public without the help of a wig of any sort. The satisfying part was that I did not have to worry about the style and color of the wig I selected and how hot it was going to be on my head during the warm summer months when my makeup threatened to melt off of me as soon as I put it on. On the other hand, I needed to master the art of looking at the back of my head in a mirror to see how my new hair looked. I began to think of it as the dark side of the moon. No longer would I have the ease of styling a wig on a wig stand in the back so I knew it would look good on my head.  

Also, not wearing wigs anymore opened up a new wonderful world for me of visiting women’s beauty salons. I will forever remember the first time my daughter gifted me a visit to her upscale salon/spa. I was just coming out of my gender shell and the whole prospect of having my hair done terrified me, but I hitched up my big girl panties and said yes. Little did I know what was instore for me. Thanks to my daughter, first of all I needed to walk through seemingly an endless gauntlet of women in chairs in various stages of having their hair done. I gathered up all of my courage and tried to walk as femininely as I could until I met my new stylist.

The first of many decisions I needed to make was what color I wanted my new hair to be. As my daughter and stylist hovered over me with what seemed like an endless set of examples to choose from, I chose a red/blond streaked shade and then had to pick how long or short I wanted my new hairstyle to be. I had no idea choosing the dark side of my gender moon would be this difficult. Quickly though, I chose an off the shoulder look which maintained most of the hair I had grown. All too soon, my appointment was over and I was spun around in the chair to see the new me and I loved her! All the years of frustration of not being able to afford quality wigs or take care of them faded away and the best part was I had been blessed with visits to women’s spaces such as beauty salons and I walked away from the experience knowing why so many ciswomen value their beauty visits to the hair salon the way they do. The day following my first visit to a serious upscale salon, I thought I had been exposed to so much estrogen, I could skip my daily dosage.

I guess you could say, having my hair done was just the first of dark side of the moon gender moments in my transfeminine life. When you add in all my other journeys into women only spaces, there were plenty of other experiences to mention. Like the one I rarely recall when I was invited to go out and party with a few of the servers, I met at one of the regular sports bars I hung out at. Like the experiences of having my hair done, I had been out several times on girls’ nights out invitations in my past, but never like this one. These women were all much younger and prettier than I was so I wondered how I would fit in. The answer was that even though they were all nice to me, I did not really fit in at all. The other women were too busy getting hit on by guys so there was little time for other socializing. I quietly sipped my drinks and pleasantly left with the group when most of them did. More lessons learned.

As far as any major male to female feminization process goes, there are inherent risks to be taken when you go through the process of losing your male privileges and discovering your new feminine ones. I know in my case, I was starting to know I was successful as a transgender woman when I began to be treated in certain ways. Such as when men in particular began to question my intelligence as I talked to them. I thought to myself, did I treat women this way?  I was definitely on the dark side of my gender moon as I explored a new world.

As you begin to explore your new world, there is plenty to do such as gathering the courage to use the women’s rest room. Which is a natural need when you are out and about for any length of time as your new trans woman self. Not any of the rightwing paranoia being spewed by the bigots saying we are men using the women’s room.

Actually, exploring the dark side of your gender moon can be an exciting experience and one you have waited your whole life to take. Take it far past just styling your own hair and/or wig and expand it all the way to discovering a new world you wanted to live in so badly. Just try to enjoy the discoveries you make and any aha moments you live through. There is so much to be learned when you jump the binary gender border to live on the other side. All the work I put in was certainly worth it.

 

 

 

 

 

 

 

Monday, December 15, 2025

More Downs than Ups on the Gender Roller Coaster

 

Image from Pietra K. 
from UnSplash.

The gender rollercoaster of life was very real to me.

That is the reason I attempt to mention all of the ups and downs I have experienced over the years as I battled gender dysphoria. For me, the trip up the coaster was not often worth the trip down as my depression set in. Until I received the proper care for my depression, I would often not want to even get out of bed for days at a time. Of course, I could not do that, and life would have to go on. That life included an increasing interest in cross-dressing. When I was on an upswing, life was better and I thought I was even making strides towards possibly living my future dream of living in and competing with a world of cisgender women. All of which had a very large headstart on me towards possibly achieving their womanhood before I could.

All this turmoil sent me down the rollercoaster of life and right back to where I started from…deeply frustrated. It was not until I began to leave my closet or shell and explore the world, did I begin to experience any relief. In the world, I discovered that not everyone noticed me and it was true what my second wife told me that it was not all about me. I was relieved when I learned that most of the world was just living life on their own terms and outside of few haters, I could live my life too. It was when I discovered that I was able to ride the level part of my dysphoric roller coaster, for a while.  

It never failed that when I started to come off the flat spot of my coaster, I needed to fight my depression again. Nothing I was doing was good enough as a man or a woman. I was so involved in wanting a transfeminine future, I could not maintain a good solid relationship with my long term (25 years) wife. The only things I was doing was keeping my head above water at work as I carved out the beginnings of a new transgender life. While I did all of this, I managed to make myself miserable as well as those around me. If I could not live with myself, how could anyone else, was my main thought pattern as I rode the roller coaster of life. All I knew was, I needed to hang on tightly for the ride ahead.

Of course, you all know I did manage to hang on, or I would not be here writing this today. Many times, it was because deep down inside I had this unmistakable idea of what I was doing was right. I had waited a long time in line to ride this gender rollercoaster, and I was not ever going to give up my spot. Once I came to this conclusion, I was able to stand in line with other ciswomen and not be so intimidated. And they were less intimidated by me and the rollercoaster hit another exhilarating turn as it headed into a tunnel. This time though, coming out of the dark did not mean I was heading into so much depression. Still, I knew I had a lot of work to do before I could reach my goal or dreams of living a fulltime transgender life.

Every time I thought I had finished a ride on the roller coaster, I found I needed to turn right around and get right on. A ciswoman’s life was so much more complicated than I had ever planned for, there were more challenges ahead. I still had key decisions to make concerning how I was going to live my new life. Such as how I was going to support myself and what was I going to do about telling my remaining family and friends that all along I had been living a lie. Last but not least, I would take the major step of seeking out approval to begin HRT or gender affirming hormones.

Amazingly, each time I jumped on the roller coaster, my rides became shorter and less eventful. I had taken the time and effort to set myself up as a regular in certain venues I went to all the time, so I did not have to go out just to be alone. I was always a social animal as a man and now I was too in my new exciting feminine world. Most importantly, I was able to develop a small circle of ciswomen friends who unknowingly boarded the coaster with me. They showed me the final steps I would have to take to get off my lifetime ride permanently. Maybe the best part was they never knew what they did for me. Eventually, what came out of it all was my marriage to my third wife Liz. A lesbian ciswoman who was instrumental in kicking me off my roller coaster permanently.

Even though I was ultimately successful in reaching my transgender dreams, I am not so sure I would recommend how I did it to anyone. I took too many chances and consumed too much alcohol along the way. Often, I used alcohol to give me a false sense of security when I was riding a scary coaster. Those were the days when I had to internalize my emotions and fear and “be a man.”

Finally, and thankfully, the world around me changed and I stepped down off my roller coasters all the way to less intimidating merry go rounds. Even they didn’t last as I decided to leave the gender amusement park altogether. Truthfully, I never got much of anything which was amusing anyway, and on some occasions, bigots and haters even put me into the freak category. Sadly, I never won any prizes for the most rides on a roller coaster or had a chance to reach for the ring on the merry go round. I was at least a survivor. I did not have to be a man at all.

Sunday, December 14, 2025

Wintertime in Ohio

 

Hair by JJ Hart, Beadwork by
LizTDesigns.

My wife Liz sells a fairly wide range of her artistic/crafting skills on a platform called Etsy.

Yesterday, she ran into a shipping snag with an item that she sold, and we had to venture out into a very busy scene as everyone was out before a winter storm hit. We did not have far to go to get to the shipping store and then the post office, so I did not have to do any prep work for the brief trip. In fact, I did not even have to shave closely since we had gone out to eat the night before with her son at our favorite restaurant.

The bottom line was when I finished writing yesterday’s post, and Liz abruptly said was I ready to go, I was. I was in a what you see is what you get mode. I was not a transgender woman, I was me, and I am always interested to see how that attitude plays out. Because no matter how long I have been out in a transfeminine world, I still have a little voice in the back of my head wondering will I be discovered as some sort of a gender impostor.

As it turned out, the only person I encountered closely with Liz paid no attention whatsoever. I was just another face in the crowd while she worked her way through the problem Liz had and then we were off to the post office. As I said earlier, everything was crazy busy which meant the post office was going to be also. This time I took the easy way out and stayed in the car. I was in jeans, an Ohio State sweatshirt, fleece and snow boots so I was quite comfortable in the car while I waited.

For once, the weather people were dead on, on their forecast and we got between six to eight inches of snow before the temperature plummeted to below zero (F) temperatures. We have a fairly new furnace and plenty of supplies so we should make it with no problems until the temps rise back up in the middle of the week. In true Cincinnati style, the high temperature will be near fifty degrees.

In January Liz and I have another vacation planned to go south to warmer climates, and sometime I am going to venture out to our local pharmacy to get another Covid booster. Hopefully, this shot will keep me out of the hospital which is what happened last year when I caught Covid and ended up in the hospital for three days in Georgia in the Atlanta area. It’s not until the 24th of January but time flies when you are having fun and will be here before I know it.

In the meantime, I know the brutal winter weather is affecting large portions of the country, along with flooding in the Pacific Northwest so I hope you are surviving the best you can.

Thursday, December 11, 2025

Trans Girl and the Christmas Season

 

Image from Roberto Nickson
on UnSplash.

Little did I know that Christmas would pass Halloween as my favorite season when I transitioned genders to the one I wanted. There were several factors which contributed to the change I was going through.

The first one was the ease I found I could get lost in the Christmas shopping crowds when I shopped as a trans woman. As long as I followed my fashion instincts. I learned I could follow several different shopping paths. For example, one day I could dress up and go to an upscale mall, and on the second, I could dress down and go shopping at a nearby local antique mall. I enjoyed the feminine freedom of choice immensely.

The second main reason I came to love Christmas so much more was I could really get into the spirit of giving. For some reason, being my transfeminine self-slowed me down and encouraged me to choose more thoughtful gifts for the people I cared about.

The third man reason was I could get lost as a woman in the hustle and bustle of the season. I forgot all about the buy something quickly and move on person I was as a man. My second wife was a huge gardener which made garden themed gifts popular with her, so I could shop at both style of malls for her garden gifts…new or vintage. In particular, I remember finding her a vintage seed merchandising box which she ended up cherishing in her collection. Right or wrong, she never found out my male self-did not buy it at all, my transgender side did.

Reason four was shopping as a woman took all the guilt of sneaking out of the house dressed as myself to buy gifts. I told myself I was not cheating on her when I did it if I was buying her a gift. Probably not the best reason in the world, but at that time it was the best one I had.

Reason five was that Christmas was such a longer season for me than Halloween. Halloween was an intense build up just for one day, and then the let down set in. Christmas of course lasted much longer, and I had the satisfaction of knowing my feminine self-bought all the gifts under the tree.

The final reason I can think of is since my wife always had a special gift giving night for my transfeminine self, I always felt guilty when I came up short for gifts for her. She was not much into makeup and fragrances and such, so the traditional ciswoman gifts were out. She never found out all her gifts could have been given out that night because of who they really came from. Instead, I ended up letting her open a few gifts at a time before Christmas itself.

Christmas at my house and my restaurant became a major holiday from the point of decoration. My wife had quite the collection of animated holiday figures, some new and some vintage which I was expected to find a way to display. As I did, I was put in a festive Christmas mood and made me more impatient to join the masses and do more shopping. Or at least all my finances could stand. Through it all, I was gaining the all-important confidence I would need to consider if my transgender dreams could become a reality after all. I could only discover if I was on the right gender path by the trial-and-error method. By attempting to stay out of the mirror and let the public tell me if I was right or wrong. I don’t know if the public was kinder at Christmas or not, but for some reason I was getting by and enjoying myself as a transfeminine person even more.

All these Christmas holiday positives did not leave me like the Halloween ones did. They became ingrained as I built my new life. A trans girl at Christmas soon became a trans girl period. All my learning gave me a new foundation to stand on when my life hit the skids, and I nearly lost everything. I lost my wife, what close friends I had, and my restaurant within a two-year period to death and recession. As it all crumbled before me, my feminine self-stood strong and ready to help. All I needed to do was let her with no strings attached. To ensure I could make a living until I could retire, I sold all the vintage items I had accounted for and was able to make enough to pay my back taxes and then retire from a job I hated. It worked because then, I would not have to worry about transitioning to a new job.

Now, since my second wife and her love for Christmas has long since departed, my daughter has converted to the Jewish faith and my wife Liz is wiccan, my overall interest in Christmas has waned. However, I will forever remember the festive seasons I went through in my past which helped me along so much in my male to female transition. I developed the instincts I needed to survive in a scary, exciting new feminine world. Being a trans girl at Christmas really worked out for the best for me.

 

Tuesday, December 2, 2025

For Better or for Worse

 

JJ Hart. 

In this case, for better or for worse should not be totally applied to the state of a transgender person’s marriage. Although, it often is.

In this case, I am talking about what happens when we attempt to break out of our dark, lonely gender closets and enter the world. I write long and often concerning the struggles I had when I first tried to come out of my mirror and appear in front of the public as my authentic feminine self. By doing so, I quickly learned I was in over my head as a novice transgender woman or even a cross-dresser. Even worse, I had my second wife telling me I had no idea of what it was like to really be a woman. Even though I was stubborn and did not totally believe her, I set out to discover what she was trying to tell me. The worse part when I tried to find out more about cisgender women was, I was not prepared to go behind the gender curtain to find out what was going on. In reality, I was years away from having the experiences of knowing what my wife was talking about.

At that time, I was still obsessed with how I made my male to female transition appearance wise. All I need to do is go back through all my old blog posts to see how vain I was about how I looked like a cross-dresser and how it dominated my life. As I focused on every little aspect of my appearance. At first, it was all great fun before I began to focus on a higher goal. Something kept telling me I was going to have to do more than just look like a woman to ever satisfy my gender dysphoria which would not leave me alone. As I wiped the makeup off, I sadly knew my male life awaited me again. I so badly wanted off the gender merry-go-round I was on then get on with my life.

It helped a little bit when I finally came to the conclusion, I was more than a weekend cross-dresser and fit the definition of a transgender woman perfectly. All of a sudden, my life had some sort of a meaning it had been lacking. I began gaining access to cisgender woman spaces I had been denied in the past and I was able to see what my wife was talking about. Or I was paying my dues to achieving womanhood on my terms. The better of for worse began to sneak in when I found all the negatives I would have to learn as a transfeminine person. Primarily when my male privileges were taken away and I lost all my personal security I had taken for granted my entire life. And the easy access I had to just going to the rest room as a man. Going as a woman, was such a different experience I could (and have) written complete blog posts about my experiences.

The better part of all of this was, I did not have to put up with the male drama that most ciswomen go through in their lives. I was a prime example of a terrible male partner for my wives to live with. Time and time again, I tried to not be selfish with my desire to be a woman and have it destroyed our entire relationship. The worse of the better or worse was when I became completely jealous that my wives could live as women and I could not. I just could not help myself. Plus, when I came out fully and transitioned I did it in the company of ciswomen who I was used to and did not ever have to adjust to male drama again. I am now married to a ciswoman lesbian who I have been with happily for over a decade now.

I was fortunate when my best transition plans worked out as well as they did. I love it when a plan comes together and even though it was a blind plan, somehow it still came together. It helped when my feminine inner soul was able to take over and run my life. She had been waiting for years, not so patiently wanting her turn to live. She provided the backbone and comfort I needed to move forward in the latter stages of my male to female gender transition.

What I considered a burden, and the worse part of my life, turned into the best part of my life when I was able to experience my impossible dream of living as a transgender woman.

 

 

 

 

 

 

 

Friday, October 17, 2025

Here Comes Tomorrow

 

My wife Liz, anniversary image.

Liz and I’s wedding anniversary was yesterday, and of course we had to go out and celebrate the event. It is actually our third anniversary after being together well over a decade.

Over the time I have written this blog, I hope I have not been short on trying to relay what my wife Liz has done for me. So much, as a matter of fact, she kicked me totally out of my closet, and showed me tomorrow was here. I could live a life as a transgender woman, finally free from my old male self. She was the direct opposite from my second wife who kept telling me there was no way she wanted to live with another woman. Liz told me she saw no male in me at all, and the rush was on to complete my male to female transition.

By the time all of this happened, and my second wife passed away, I was well into my sixties and had given up any hope of ever finding another serious relationship. Preferably with another woman who would accept me. As I always point out, to combat my severe loneliness, I was working the bar scene and even tried online dating which turned out to be a joke…until I met Liz. Or she met me. She responded to a “woman seeking woman” ad I put on a dating site and as luck would have it, she lived relatively close to me in Cincinnati. At the time she commented on the picture I used, saying I had sad eyes. Which I did, seeing as how I was going through the toughest time of my life. I had just lost my wife of twenty-five years as well as nearly all of the close friends I had to death as well as losing my business. I was grasping at any straw I could to stay afloat, sad eyes or not.

The only main straw I had was my sudden dependence on my strong inner feminine self. In a time of darkness, when my male self-had deserted me, she stepped up to provide the comfort and strength to move on. It was up to her to carve out a new life with new friends who had no previous contact at all with my old male self. Against all odds, in a sometimes-hostile world, she managed to do it, and my life slowly began to improve. With all the help and attention, I was receiving from my new ciswomen friends, I did not have to even give much of a second thought to the men who were afraid to approach me or just wanted to treat me as some sort of a fetish object. With my base sexuality settled again, it made it easier to feel secure in myself and move on with my male to female transition. Often it seemed my life was coming full circle and Liz was a major part of it.

During our anniversary dinner last night, we were fortunate that the venue was very empty without even the usual screaming kids so we could reminisce about our past and dream about the future. And of course, Liz took all the credit (as she always does) for reaching out to me first as a “woman seeking woman” post was an exceedingly rare response coming from any other women in those days. Plus, I was not shy in pointing out I was a transgender woman made my odds even more remote. If I received any responses at all, I felt like I had won the lottery of dating as a trans woman.

Because of Liz, I won the lottery for all the reasons I went into and more importantly, my gender transition which was always tomorrow became today. It was time to give away my remaining male clothes and follow Liz’s instructions on following my heart. A heart, it turned out, was feminine to start with and needed little to no encouragement to live. Regardless, when tomorrow finally came, it hit me hard and I needed time to adjust I really did not have. I needed to fall back on the decades of cross-dressing practice I had to feel more comfortable in the world. When I did, the joy of life I experienced was wonderful and even more so because I had someone special to share it with.

To be able to live the way I do still feels like a dream to me and Liz has helped me to realize my transfeminine dream more than anybody else ever did in my previous life.

Happy anniversary Liz and may we be able to celebrate many more together. And, thanks to all of you who have joined me in my journey. If you have not reached your tomorrow yet, keep trying. I am living proof it can still happen.

 

Wednesday, October 1, 2025

Just a Man in a Dress?

 

JJ Hart (left) with wife Liz.


Just a man in a dress has been used to describe me in my past.

I suppose it was true to an extent when I was a part-time cross-dresser. But it all changed when I finally grasped the idea, I was so much more than a cross dresser, I was transgender. Ironically, the idea came to me out of the blue one night when I was going out to be alone. As I was applying my makeup and getting dressed, it occurred to me that my life was different. Instead of just wanting to look like a woman, I wanted to interact with the world as a woman. The whole idea terrified me, but I knew if I was successful, my life would never be the same again.

To be successful, I knew I needed to be very careful to blend in with the professional women I had seen previously in the venue I chose for my grand experiment. To scout it out, I went there as a man to get my potential timing down. Once I did, it was time to try to increase my confidence and calm the major fear that I had that I would be called out as a man in a dress. Looking back, I think I sat in my car for a half hour adjusting my makeup, before I gathered the courage to go in. Making a long story short, I was successful and managed to even stay for an extra drink before I left and I was right, I knew my life would never be the same again. I had crashed through my cross-dressing barrier and landed comfortably in the transgender phase of my life.

As I changed, I had the baggage of two worlds to bring with me. One was my past as a man and the second was my experience as a crossdresser. Of the two, my male past was the most difficult to shake, mainly because I had worked so hard to maintain it. I desperately did not want anyone to see I was feminine at all. It turned out I was so successful portraying a man, that everyone I knew was surprised when I transitioned. It was difficult to explain to them I was so much more than a man in a dress, I was a transfeminine person. Then I needed to explain what I meant about that. At that point, I found actions spoke louder than words and they had to see me repeatedly as my dominant feminine self to understand where my life really was.

These days I am so fortunate to be surrounded by people who accept me for who I really am, so much more than just a man in a dress. They shield me from all of the evil stupidity coming down from the orange felon and his minions in the white house. I feel so sorry for the transgender troops who were loyal, qualified members of the miliary who lost their jobs out of ignorance. You all know how I feel about what is going on in Washington, so I don’t have to repeat myself, and ruin this post.

As far as the day-to-day world went for me, I discovered I was remembered easily, so it was not too difficult to begin to build a new feminine person from scratch. I needed to decide on basics such as wearing the same wig and using the same name to get me by. What I was doing was changing wigs and names thinking the process would help me pass magically as the woman I so desperately wanted to me. What I learned was, there were no shortcuts on my male to female transition path. If I was going to make it to my goal of living fulltime as a woman. I also quickly realized, once someone saw me a couple times as my authentic self, they knew I was much more than a man in a dress.

My disclaimer in all of this is, I am not in any way putting myself up on a pedestal and saying I am better than a cross dresser. On the other hand, the opposite is true. I appreciate the time I spent crossdressing. The whole experience taught me so much. Perhaps the biggest lesson was I could make it to my dream of transgender womanhood if I worked hard enough. I most certainly did not think at any point my journey would be as complex as it was. I found to be successful; I needed to be better in life than the average cisgender woman who had huge benefits on me from growing up female. Catching up proved to be difficult to do as my gender workbook was blank. As I always say, I am not taking all of the credit for my success and putting myself up on some crowded pedestal. I found cisgender women to help me.

They realized early I was so much more than a man in a dress and stepped up to help me into their world.

Vacation Time

Crosswell Tour Bus from Cincinnati .  It’s vacation time again, so I will be missing in action for the next ten days or so, with no posts. ...