Showing posts with label transfeminine. Show all posts
Showing posts with label transfeminine. Show all posts

Monday, October 12, 2026

More Than Just a Passing Fantasy

 

Image from Alexsy Turenkov
on UnSplash.

As I made my way into the public’s eye as a novice transgender woman, I needed to prove to the average person I was much more than a man in a dress with a wig and makeup.

It meant I needed to change my entire thought pattern too about who I thought I was because for the longest time, I considered myself more or less a feminine “hobbyist” who dabbled in wearing feminine clothes and makeup. I considered myself as serious about my hobby as much as I did my brother being serious about his golf game.

Ironically, I can not put my finger on the exact moment I started to change my overall thoughts on myself, but it was a gradual process. Triggered by me being exposed to the transgender term for the first time in my life. It all came from the fact that I knew there just had to be more to what I was doing with my feminine self than just a casual process and the transgender terminology appealed to me. Being trans took me another step towards living my ultimate dream of living as a transfeminine person more than anything I had ever read before.

All my research into gender dysphoria and its effects on me led me to slide myself increasingly on the gender scale to the feminine side of the spectrum internally. Which was the easier part initially. Then, all I needed to do was internalize my feelings and keep on living my male life so no one would notice that I was different at all. The problem was, I did not know how much internalizing my gender dysphoria would hurt me in the short and long term.

As I always knew, but tried to hide, just cross-dressing was never going to be enough for me, as I wanted to do more with my life as a woman. Of course, once I realized it, I needed to plan a course to do something about it. Being stuck in a restrictive single occupant closet was not going to be enough. Somehow, I needed to gather the two C’s, courage and confidence to take on the world as my authentic feminine self if I was ever going to do more than jut survive in the male world I wanted nothing to do with. I needed to get out of it and convince others I was so much more than some sort of a drag queen playing a part of a woman.

Little did I know, the drag queen problem would take care of itself everywhere but in the gay venues I was going to often. After I was done hitting my head against the wall in the gay venues, I decided to go back into the world once again to see if I could be viewed than more than someone’s fantasy object. Accomplishing it became easier to me than I ever thought possible when all I had to do was to keep going back to the venues I had frequented as a man but this time as a trans woman. If I managed to wear the same wig and look the same, I was hard to miss and easy to remember if I followed my basics of always being pleasant, never causing problems and tipping well. By doing so, I became a regular before I knew it and I started to carve out a whole new feminine life away from my male past. Most importantly, there were no passing fantasies involved for me, no smoke and mirrors as I was actually doing it.

I continued to take my trans show on the road, so to speak, as I tried to live every spare moment as a woman to see if my dreams were more than just dreams and not turn out to be nightmares. I was trying to make sure I had all my life’s basics covered if I was ever going to give up everything I had earned as a man. Use what I could as a transgender woman and start all over again. That way, I would not totally be starting over, I could take what I learned as a so-called cisman and apply it all towards the scary but exciting new world I was living in.

Doing the same things over and over as a woman helped me to carve out the new life I had always wanted to live. Other ciswomen knew my name and wanted to know more about my life because they were curious why I wanted into their world. I was in heaven and continued to want more as my life changed for the better. It all did because I had the courage to put myself out in the public’s eye. While I never managed to be the most attractive woman in the room, I was the most consistent with my look. Which was all I could do with what I had to work with in my testosterone poisoned body. It took me a lot of time and effort, but I put away all my old misgivings about my life’s journey and kept my momentum up towards my extreme male to female femininization project.

By this time, most all the family and friends who meant anything to me had passed away leaving me all alone in the world to do what I wanted. After all those years of playing around with thinking I was a casual cross-dresser had completely left my mind and looking like a woman was much more than a mere fantasy, I was ready to move forward into the world I had always should have been a part of. It turned out to be a for better or for worse deal for me by this time. I had put so much effort into the struggle to femininize myself and get out of the male world that it all turned out for the better as I entered a win-win situation in the world.

In fact, during my life, there was no way I ever could have fantasized arriving in the place where I had arrived. I love it when a plan comes together. Even though it took me so long.

Thanks for reading along with all my hopes and desires during my life.

Thought are always appreciated!

 

 

Sunday, October 11, 2026

A Destination or a Retreat into Trans Womanhood


Image from Brian Wangenheim
on UnSplash. 

As a youth, all I did when I failed at a male task was to seek the reassuring feelings of my feminine clothes and makeup. I knew then I would not have the male world I hated for a while.

The pattern continued with me into adulthood and was even expanded to include a better sense of wardrobe and makeup as I ventured into the world. But then it started to slowly reverse as I started to blend in with the ciswomen around me. Increasingly, I was feeling better about the progress I was making as a serious cross-dresser and wanted to do more as I moved towards being a transgender woman in my mind. Even though I was still extremely lonely as my feminine self, I was starting to embrace the unique person that I was. Afterall, how many people get to experience both sides of the primary genders in their lives.

On occasion, I even reverted to appreciating all the male privileges I had learned after a particularly brutal day of exploring the world of cross-dressing. Early on there were many I needed to go through as I continued to pay my dues to get to my dream of possibly living my life as a transfeminine person. Not a man.

Even though mixing genders was beginning to have a bit of normalcy for me, I came to the point where I would not recommend the journey to just anyone who was not totally committed to it. My mental health, which was already frail at the time, did not take easily to the journey ahead and it suffered. Again, sending me back to the comparative safety of the only other life I had learned to live successfully when I was competing as a man in the world.  At that point, it was difficult to tell if I was on a trans destination or a male retreat. The only thing that kept me going down my path was the deep sense of satisfaction or gender euphoria I felt when everything was going better when I interacted with the world as my true authentic self. Free and out of the closet for a change.

It took me years of experimentation in public, as I set up my own personal bucket list of what I perceived to be the real-world ciswomen had to face in their lives. I figured out why I would want to go there if I could not make it. In other words, I kept challenging my feminine self to do more and more such as do more than just spend very little time in public just walking around or shopping in easy venues such as women’s clothing stores where your money overcomes any reaction to your possible gender when it came to testing myself. I certainly then was setting myself up for a possible transgender destination in my life as I worked my way through my bucket list.

As with anything else in life, all I had learned about being in the world was not all positive and I found myself deeper into my quest to cross the gender border and complete my male to female femininization project. I learned the hard way to try to not get myself into questionable safety situations that women know not to get into that do not bother men. It seemed the gender universe was testing me on certain nights such as the one I needed to fend off negative advances from a much bigger cross-dresser admirer at a party I was at with the help of my second wife. Something I never bargained for as I went around a blind corner on my gender path. It was easier to think about erasing all my male privileges such as safety but harder to learn what to replace them with.

I do not think I ever did replace my new lack of intelligence with the cismen I interacted with as I was mansplained more times than I cared to remember by men of questionable intellect. Such as the tow truck driver I was forced into a conversation with one night when he was towing my car home. I had to sit there, and act interested when he had to tell me all the workings of his truck. Like I cared when all I wanted was to get home safe and sound. Which I did. All the bucket lists in the world did not prepare me for the reality of living a feminine life, but even still, I was loving everything I learned behind the gender curtain. If I was ever a girl scout, I would earn merit badges like what to do if your car breaks down when you are by yourself and the first person who stops to help is a sheriff. Who would not listen to me when I was trying to explain to him and the tow driver the easiest way to my house. I finally just gave up.

It soon was becoming obvious to me that I was no longer retreating behind my dresses and makeup to cover any vestiges of a male life I wanted to cover up. Instead, my full-fledged female life was a complete destination. A destination I wanted to do more than anything I ever had done in my life. There would be no more retreating back to my male world. No matter how easy it would have been to do it because he had always kept a comfortable home for me if I ever wanted to return. Much to his disappointment, I continued my feminine destination into the world of HRT gender affirming hormones which separated me farther from ever hiding again in my old unwanted male world.

HRT was certainly the end for any thoughts of ever returning to my old male self because I felt to increasingly natural when I took them. It was as if my body was telling me what took so long as my external self-synced up with the woman, I always saw myself to be. It just took me years to get there. Which was the tragic result of me not listening to myself.

Thanks for reading along on a few of my trials and tribulations of my gender journey. I hope yours is much smoother. Any comments are always appreciated.

 

 

Monday, August 24, 2026

Help Me Out of this Box!

 

Image from Tamara Bellis
on UnSplash. 

Since I was born “AMAB” (Assigned male at Birth) I was automatically put into a box I could not easily get out of.

Plus, I had the extra disadvantage of being born into a very male dominated, competitive family, so my box was harder to get out of. Like many of you, I had to sneak around my family’s back to even cross-dress into mom’s clothes and makeup to feel better. The worst part about it was that I did not understand why I wanted to be feminine and felt so all alone when I thought about it. Society had done a good job of building a sturdy box around me with very high sides to see the world out of.

As life went on, I learned to be self-sufficient as I hid my gender truth from the world. Very early on I learned I wanted to do so much more than just look like a girl, I wanted a chance to live their life. But I needed to escape my box somehow to do it with absolutely no help from anyone at all. There were only the girls at school for me to envy and try to copy myself after I returned home and had a chance to cross-dress again in front of the mirror.

When I first tried to take myself out into the public’s eye for the first time, it was difficult leaving my box to do it. I was safe there, and I could be the pretty girl I always wanted to be without anyone questioning me. Even though I was not surviving the world well as a novice cross-dresser walking through the malls that I knew, I was determined to keep trying until I got it right. That is if I ever could as I was very insecure in thinking I ever could come close to my dream of living as a woman.

As life always does, it got directly in my way of ever getting out of my box. The only way I could try very early was by going to Halloween parties dressed as a person who I really wanted to be in life but could never tell anyone. At least at Halloween, I could show the world the transfeminine me and hope it did not wreck my life at the time before I could scurry back to my box and hide again. The problem with Halloween was it only happened once a year and I couldn't wait for the next one to show off my feminine spirit. It all led me to gaining a greater awareness to who I really was and how much I needed to expand my world as a new transgender woman in the world.

Another problem I had was having two strong influences around me, who wanted me to stay in my box and even make it stronger. The two were my male self and my second wife who had everything to lose each time I gained more confidence as myself. They did not understand the turmoil I was going through myself and could not help me, I was on some sort of a gender roller-coaster with all its ups and downs. One of my major ups or gender euphoria came when I was mistaken for a ciswoman at a cross-dresser, transgender mixer I went to one night without my wife. That was certainly the high point, but then the lows began to hit me when I was firmly stuck back in my box with no way to experience the next high. Sadly, I did not know where my life was going to take me then. Except for the small idea that I might have the appearance part of my gender puzzle solved.

More frustration sat in when my wife told me there was so much more to being a woman than just looking like one and I was stuck with no real way to understand what she meant. I was still operating as too much of a cisman to be allowed to be behind the gender curtain to understand all the complexities ciswomen go through in life. To make up for it, I tried to adopt female mentors to learn from. Immediately I chose my mom and my wife to learn from because they were both strong, independent women whom I wanted to be like. It was a true jump for me to go from being a shy trans woman hiding in my box at home to getting out and trying to find out if I could live my life-long dream. What I did was build up confidence slowly until I could shed my male self and his privileges and just do it.

Little did I know, when I did shed my male self, I would end up bringing a big part of him with me. I made him my beast of burden when he carried what was left of him into my scary, yet exciting new world. I learned again how complex ciswomen were and if I wanted to watch sports on a big screen television with a beer in front of me I could and not feel out of place as a transgender woman.

In many ways, I was dismantling my old box and using the pieces I needed to construct the new me who had always been there but had nowhere to live. It felt great for once to feel free of all the old male constraints I had to live with. I had many, so the path I embarked on became very complex as I sorted out exactly who I wanted to be. Plus, I needed to be careful to finally judge when the best jumping off point for me to put my old male self behind me and start a new one. A unique spot that most humans do not ever have the chance to do.

If you are considering what you will do with your gender box, just be careful when you deconstruct it because it can contain many hidden problems. On the other hand, you are embarking on an exciting journey if you can make the best out of it.

Thanks for reading along with all my lifetime adventures as I attempt to bring our gender struggles into focus. Taking the time to read, and comment too are always appreciated!

 

Monday, July 13, 2026

Gender Binges

 

Image from Andy Arjun
on UnSplash.  

Binge cross-dressing happened a lot to me when I was quite young.

Once I was able to scrape together my meager finances to put together a small wardrobe of feminine clothes that barely fit me, I could not stay away from wearing them more and more. In fact, I was able to come up with two main hiding places away from the prying eyes of my family and most importantly, my slightly younger brother. It was about that time that I really became involved with binging in my new clothes which I felt made me look like a pretty girl.

Very soon, regardless of the risk involved with me cross-dressing as a girl, I was doing it as much as I could get away with. I think now that my mom had to know something about my cross-dressing but was either afraid to say anything about such a complex subject or thought it was a phase that would go away. Obviously, the joke was on her. My wanting to be a woman never did go away; I just matured into it. Plus, back in the late 1950’s and early 1960's, there was very little good information about gender issues to deal with, so we were on our own as gender issues were called mental illnesses. Which even I knew at such a young age was not true. For all I knew at the time, I really liked experimenting with mom’s clothes and makeup and binge dressing was becoming routine.

As I said, once I began to mature into being a more accomplished cross-dresser (even before I considered myself transgender) I managed to dress more and more. I was even able to buy a beautiful long blond human hair wig that she hated and I loved. Finally, after I changed girlfriends, she went away and I kept the most important part of the relationship to me which of course was the wig. It brought me to a whole other level of cross-dressing away from Halloween wigs into the real deal. Back in the 1960’s when miniskirts were in, I could not wait until I could find a chance to slide on pantyhose and miniskirt and top it all off with my blond wig. Yes, I did binge any chance that I got!

Sadly, my binge dressing needed to come to a complete halt during my military years in the Army. Instead of worrying about how short I could wear my miniskirts, I had a more immediate and important problem of how to deal with weapons and drill sergeants in Army basic training. How I survived was that I put all my fond memories of cross-dressing in the back of my head and daydreamed about the future I knew I could have shaving my legs again and binge dressing as a woman.

After I served my time in the military, the only immediate release I had from all the tension I felt to be feminine at all was with all the many and varied Halloween parties I went to. During that time, I went from being a French woman with my blond hair, black outfit, tights and beret, all the way to professional woman one year when I was mistaken for a ciswoman just getting off work. The good news was I was learning a lot, and the bad news was Halloween only came about once a year. I needed desperately to find another way to binge with a purpose and express myself as a transgender woman. A term I was beginning to accept as my own.

Once I began to accept who I was, I needed to set out to prove it to myself and the world that I could live my truth. It was then that my binging took a whole different direction from where I was before. Thanks to the basic acceptance I gained from successful Halloween parties, I had the confidence to know I could look the part and blend in with society as another ciswoman. Little did I know then, the hardest part of my male to female femininization project was yet to come.

It took me finally getting out of the gay bars I regularly went to for some sort of validation I never received and into being accepted as a regular in many of the straight venues I went to and enjoyed as a man. My validation as a regular gave me the confidence to keep trying to improve myself as a transgender woman rounding out her life in the world. As I achieved goal after goal I set up on my trans bucket list, I really binged out every chance that I got which put me into a direct collision with my second wife who did not want to live with another woman and my male self who was dead against giving up his life all together.

By all out gender binging, I had set myself up for an internal war I was fortunate to survive. It took me all I could do to keep all my lives together as the years progressed. All I knew was I was able to carve out a dream existence as a transfeminine person. No one knew of my male past, and I loved experiencing every moment of my new life. Deep down, for once I felt I was fighting my self when I was binging as a trans woman and expressing my true self.

By turning back, the clock the best I could, I tried to take the best that I learned from my male life and apply it to building a solid base for my female life. I think it worked because I was able to decide which of my male baggage was important enough to bring along and I benefitted from being blessed with a long life, so I can see a number of important things come full circle (which is another blog post.)

The bottom line is I have always been an impulsive person which helped me all the times I just had to binge to satisfy my needs. Dealing with my gender issues was just an integral part of that.

 

 

 

 

 

 

Sunday, July 12, 2026

A Want...or a Need

JJ Hart Discovering her Needs
I am in the first row on the left.

When a want turns into a need, sometimes you can feel it. Other times, not so much as if it sneaks up on you from behind.

As I began to wear dresses and makeup as a young boy, for the most part, it was because I wanted to do it. Cross-dressing just relieved the pressure of my unwanted everyday male world. It did not take me long to figure out my want was much more than just a casual appreciation of women’s fashion and makeup.  I did not know it then (and the term had not yet been widely used) that I was transgender more than a cross-dresser. I could not feel the change because I did not have the gender knowledge to do it.

Life began to change for me when I started to cross-dress for the thrill of it and attend Halloween parties. The parties ended up teaching me the basics of being a woman in public around people I knew, and I wanted to take it a step further by not having to wait another year to try again to get out of my dark closet and into the world. That is when my story turned out to be dark as I was not met with many positives by the public as a novice trans woman, cross-dresser or whatever you would like to label me as. To too many people, I was simply a man in a dress and clown makeup. I learned the hard way to get back to my drawing board and work harder on my feminine craft to find out if I was ever going to be able to succeed at all at my dream.

I also learned that if I was ever going to find success on my gender path, I was never just going to make it by just thinking it was just a want. It had to become a deep-seated need. I went back and dieted, worked on my skin and did everything I could to improve my testosterone poisoned body. All it really taught me was how much deeper I needed to travel along my gender path to make it at all and I needed to do it very badly. As the pounds melted off, I was able to find more stylish feminine wardrobe items to fill out my fashion needs and dress for success to blend in with the rest of the ciswoman crowd. Who I learned the hard way, were the people who ran the world I was attempting to be a part of. Or I could go casual if I needed to and a more polished business look when I needed to upscale my appearance. Fashion-wise I was learning that looking the best I could and blending in with the public at the same time was a definite need not some sort of a frivolous want just to justify something I wanted.

The more I tested the world as a transfeminine person, the more I needed to do to help myself along in the learning process of just belonging in the world I always should have been a part of to begin with. It was a real chore just to put the mirror image I thought I had perfected into the public and into motion to see how it worked. For the most part, I was improving to the point where I needed to start trying to communicate with the world as a more complete trans woman. As I always point out, the communication challenge to me was immense because I had always been a lazy communicator in my life. By that I mean, I had never really had to listen closely to what another man was telling me. I knew instinctively how to respond to another man but was clueless when it came to woman to woman talk. Which I always had known was different but how different I did not know until I was made aware of it. For example, for the first time ever in my life I needed to really stop and listen to whomever was talking to me. Were they trying to point out danger to me or just being friendly as a ciswoman who was curious of me or a toxic man who just viewed me as some sort of a fetish object.

Quite possibly, the communication aspect of my male to female femininization need passed my desire to be as attractive as I could as a transgender woman in the world. Instead of just wishing and wanting to be accepted as an equal by the other ciswomen I met, I needed to make it a priority. I even swallowed my pride and took female vocal lessons to make the process easier. It was difficult, but I think I gained enough confidence to help with my overall presentation and life.

I was helped too when the pressure to succeed was relieved here and there by the new success I was having in the world carving out a new life which on one hand to be terrifying and on the other feeling so natural like I was coming home to the self I always should have been.

I found I did not discover all my true self until I could step away from me for a minute to look at how far my gender path had taken me. After years of experimenting and trying different things, I finally achieved my need to be allowed to play in the girls’ sandbox and I was not disappointed with what I found there. Even though I had to put up with the occasional hater or TERF who wanted me out, but the majority of women made me feel welcome in their world and that was all that mattered to me.

The sandbox provided me with firm lessons and reassurance in what I was trying to accomplish in life. The want I always felt was always a hidden need which took me years to realize was my true problem in life to solve.

I hope you can realize your true wants and needs on your gender path also and life becomes easier for you if you are searching like I always was.

 

 

 

  

Tuesday, May 19, 2026

Are We Having Fun Yet?

 

Image from Katie Treadway
on UnSplash.

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

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

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

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

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

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

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

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

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

 

 

                               

 

 

Wednesday, March 11, 2026

Nothing Easy but the Hard Times

 

Image from Anthony Tran
on UnSplash.

Finishing up yesterday’s post about having a medical appointment with one of my medicine providers Regina, my worst fears materialized. After years and years of seeing Regina, she is retiring and I am being shuttled to another provider at the Veterans’ Administration here in Cincinnati, Ohio. Now I have only one more time to see her before a significant part of my life begins to shift.

I think my shift will continue when I see my endocrinologist on May 7th. She is the only remaining tie to my old providers in Dayton, Ohio VA where I used to live and this visit is ultra important because I will have to ask to have my Estradiol patches prescription renewed. As I said yesterday, I am thinking about changing from the hormonal patches to self-injections which is not a big problem with me, but will it be with the “new” VA I am beginning to experience. If I am told I must get a new endo doc in Cincinnati, what will I have to go through to get my HRT, or will I have problems, is my paranoia. Time flies when you are worrying and before I know it, the time for the appointment will be here. I guess I was born to worry, and nothing is easy but the hard times.

I guess worrying fits right in with being transgender. Early in life, all I did was worry about getting caught when I cross-dressed in front of the mirror. I had plenty of hard times as I worried about my slightly younger brother discovering my feminine secret and telling my parents who would have promptly sent me off to a psychiatrist who knew absolutely nothing about gender dysphoria back in the late 1950’s or early 1960’s. At that time, I was mistaken that several of my main worries would take care of themselves as I became older. One of course was me wanting to be a woman, and the second one was what was I going to do about the military and the Vietnam War. To make matters worse, I was worried about them on several different levels. One of which being I could just relax and both the war and my urge to be feminine would just disappear.

Needless to say, both of them never went away. The war went on and on for years, and my desire to be a woman just intensified as I had more public experience when I gathered the courage to leave the mirror and go out into the world. Which I was starting to do before I entered the military, which in many ways just made matters worse. Certainly, I felt nothing was easy but the hard times as I tried alcohol for the first time to dull my pain. It was the beginning of a long one-sided love affair with alcohol I had which fortunately I won before it was too late. I took me much longer to realize my desire to be a full-time transgender woman was not ever going to go away and I would have to do something about the hard times I was experiencing by acting.

Acting meant I would have to put my male side behind me for good and plan for a radically different feminine future. That is when I truly found nothing ever would be easy in life but the hard times. So, for the first time in my life, if I ever wanted to achieve my dream, the path was clearly there to do it. Like a runway for jumbo jets lit up at night. All I had to do was learn how to land the jet.

At that point, I was rather confident that I could do it. Afterall, I had spent all those years cross-dressing and perfecting my feminine presentation, so what could go wrong. It turned out plenty. As I was completely lacking in rounding myself out as a transgender woman capable of holding her own in a world full of competitive ciswomen. I discovered I was completely not ready to communicate in a world where I needed to be better than the next woman to be accepted at all. Just presenting better as a trans woman was just the beginning I found, and I started to worry all over again.

This time, all my worries turned to action as my new life became a blur as I started to carve out a new, more complete path to my transfeminine dream. I could not believe it was me becoming a regular in venues I used to go to as a man and had wondered how it would be to visit them as a woman. I used to blame my second wife for holding me back, but learned it was all my fault, and I was just being a victim.

I think being transgender automatically brings a lot of worry with it. We are subject to violence, job and medical discrimination among many other negatives. When you add all of those to already problematic everyday lives, that everyone has, it is no wonder transgender suicide rates are so high. Which proves my point that nothing is easy but the hard times when you are trans. Reality comes when the attraction to all the pretty clothes begins to fade and the daily life of a woman sets in. A woman’s life is a many layered existence and one you have to accept when you transition.

By accepting the challenge, you made yourself, you have decided to set out and build your new life from scratch. There will be many times when you think you have bit more than you can choose, but after you have been successful, you can feel the pride and for once knowing that the hard times were ever easy but somehow you made it through to living your dream of living and thriving in a feminine world. You should be proud of your accomplishment.

 

 

 

Wednesday, February 25, 2026

Everything was OK Until it Wasn't

 

JJ Hart. Frozen in Florida

So many times, when I was caught between my genders, I learned everything was Ok, until it wasn’t.

A prime example would be when I was coming home from a night in the gay venues I was frequenting and my car decided not to start when I was twenty miles away from home. Then I needed to figure out how to get the car home before my wife came home and took off all my make-up acting like nothing had happened. What I did was call a towing company and get the car towed back home as I sat in the cab with the driver, trying my best to present as a blond woman just trying to get her car home. Somehow, I did make it that night and learned to never take that car again when I went out on such a pressure packed adventure.

Sadly, I needed to learn the hard way as I followed my gender path through many blind curves and major potholes. I would usually start out with a final look in the mirror thinking I made an attractive woman from the testosterone poisoned male I had to work from. Confidently, I moved ahead to whichever venues I decided to go to that night. And the stakes were raised significantly when I decided to leave the relative safety of the gay venues behind and attempt to see how I could do in the straight world of big sports bars. It turned out, if everything was going to be OK, I would find out quickly.

Normally I found everything was going to be OK, except on the nights I encountered problems using the women’s restroom and I ended up having the police called on me. That turned out to be more embarrassing than anything else because the cops had better things to do as I was just sent on my way. A more embarrassing night came along much later when a group of drunk guys decided it would be fun to play “Dude Looks Like a Lady” about five times in a row on the juke box. Which ended me getting asked to leave by the manager, even though I was a regular. Well, liked by the staff, who actually tracked me down at a close venue not long after and asked to come back. Telling me, the manager who told me to leave got fired. I was flattered and accepted my welcome back because everything I thought was OK, actually was.

Other times, I was not as fortunate as I began to learn the basics of being allowed to play in the girls’ sandbox. Learning the time-honored tradition of passive aggressive behavior which ciswomen practice so well, proved to be a challenge. I was used to taking another man at face value most of the time until he proved himself unworthy which did work with women. I learned a smile could be hiding something much more sinister. Resulting in claw marks down my back. Once I did, again everything really did turn out to be OK and stayed that way for the most part.

In no way, do I want anyone to think this gender male to female feminization project was a quick one. There were so many nights when I hurried home to return to my old unwanted male self that I wondered what I was doing. I was risking so much on what often seemed to be an empty dream of someday being able to live as a fulltime transgender woman. What kept me going was the deep feeling I had that when I was my feminine self, I felt so natural and I felt as if I somehow was home. And someday, all the setbacks I had would just disappear and everything would truly be OK.

Through the magic of gender affirming hormones (HRT), and strong ciswomen role models, I was able to weather the transition storm I was going through. I knew everything was going to really be OK when I found I could validate myself in the world as a trans woman without the validation of a man, or anyone else. The whole process was so much more complex rather than just looking like a woman. I needed to be my own woman, on my own terms so I could exist on the path I had always been on. Even though sometimes I did not realize it myself. Those were the days of feeling like a failure when a group of teenagers laughed at me for how I looked. Rather than staying and trying to do better, I had to run home crying and go back to my cross-dressing drawing board. Seeking the idea that everything was going to be OK, even though it was not at the time.

As I said, what kept me going was a small spark of feminine energy deep down inside me. Knowing for sure, being the woman I dreamed of being was going to be an incredibly complex gender journey to make. Just lacking the communication skills, I needed to survive in the world as I went one on one with other women made my life a scary one. Since I was shy to begin with, I needed to start from scratch in a new world and work hard to gain an equal footing as a novice trans woman trying to make it alone in the world until I was able to make new friends.

The new friends I made helped me to cushion when I got into situations when everything was OK until it wasn’t. During those times, I could fall back into the group and learn from what was going on. Every learning experience became so important because I could make sure to never try that again. Even what was left of my stubborn male self-learned the misconceptions he had about how women truly lived and did he really want to let go of his life for good.

When he did, I found that everything was going to be OK and it always was.

Tuesday, December 30, 2025

You're so Vain

 

Image from Ava Sol
on UnSplash

Expressing yourself to the world as a transgender woman carries with it a certain amount of vanity.

Until you begin to relax in your new feminine world, I think you need to obsess over every detail of your exterior appearance. Since we all have such a vast amount of catching up to do to compete with other ciswomen in the world, details matter. Perhaps one of the first lessons you learn is how competitive the world is when you are a trans woman. Ciswomen are every bit as competitive as men but in certain areas not readily visible to the male gender.

For example, the major question comes to mind that do women dress for men or for each other. Sadly, we never had the input of mothers, sisters or girlfriends saying, “are you wearing that?” I know if I had that sort of input, it would have saved me a lot of embarrassment when I first began to go out into the public’s eye. It was a resounding yes for me when I learned who women really dress for…themselves. My problem was, my male self-kept getting in the way and had me dressing like a trashy teen girl. All poorly concealed in a testosterone poisoned male body. It was no wonder I was creating negative attention and getting laughed at. When all I was doing was trying to present myself well the best way I knew how.

After I began to learn and change my thought patterns concerning fashion and makeup, I began to have success in the world. So much so, that on occasion (when I was so vain and did everything right) I received a compliment or two from a cisgender woman. One thing was for sure; it takes a woman to know the work it takes to perfect a public image with makeup and fashion. Plus, I needed to be better than the average woman because I was working at the whole image after I started as a man.

It turned out, having to be better in the world worked well with my increasing source of transfeminine vanity. All I thought of was how much better I could look if I tried just the right foundation and mascara, as I haunted the many thrift stores, I went to looking for just the right piece of clothing to add to my wardrobe of feminine clothes. My personal newfound male to female femininization vanity was in full force as I was having fun. In reality, I saw nothing wrong with being vain in how I appeared as my authentic self, until I clashed with my second wife.

She rarely wore makeup or dresses at all and did not like the way I presented myself at all. On the rare occasions we went out together as women, I tried to tone down the amount of makeup I was wearing along with putting on my most conservative clothes. All because I wanted her approval, which I never got. If I wore any less makeup, I might as well say to hell with it and go out with her as my old male self. I was stuck between the rock and the hard place as far as my feminine vanity was concerned.

As I progressed with my makeup and fashion experience, I understood how much work I would have to put out to achieve the transgender goals I wanted. I knew I would never be able to transform my old male self into the prettiest girl in the room but on the other hand I could present well enough to get by. Everything that I was doing at that point just became a blur of change. Especially when I was approved for gender affirming hormones or HRT. As my skin softened, hair and breasts grew, it all was a welcome addition to all the work I had done all those years to just survive in the world. As I wrote yesterday, just not having to wear a wig anymore was a huge deal for me since I had no male pattern baldness to contend with. All of a sudden, I needed to contend with a new form of vanity when I went to beauty parlors to have my hair done just a certain way.

During all the years it took me to fully come out into the world as a trans woman. I learned the true meaning of competing with ciswomen in the appearance arena. Once I did. I needed to move ahead to the larger context of being allowed to exist in women only spaces by the alpha-female gatekeepers. In many ways, my second wife was an alpha female who never let me in, so I wonder what would have happened if she had lived long enough to see/know the person I am today. One thing is for sure; I am no longer the “pretty, pretty princess” she used to call me because I have paid my dues as a transgender woman.

All I know is I did go through my periods of extreme selfishness and vanity to arrive where I am today and I don’t know if there is any other way to go down the path, I ended up taking. Changing a gender is such an intense way to live, especially when you started with so much success as a male that it took me a massive effort to change. Not to say, all of the effort was not enjoyable but at least, it was interesting and challenging to see behind the gender curtain.

For many of us stuck in our own form of gender dysphoria, vanity is just one aspect of our larger need to survive.

 

 

 

Friday, December 26, 2025

Alone in a Crowded Room

 

Image from Bruno Aquirre 
on UnSplash.

I often refer to the days when I was first going out and seeking clues to my true identity as going out to be alone. I called it that because I had not yet met any regular acquaintances that I would have called friends on a regular basis. So, I was surrounded by a group of strangers no matter where I went. Even so, it was better than sitting at home by myself staring wishfully into the mirror.

Following leaving my painfully shy days behind me and becoming a rather social person, I did miss the interaction with the public. Going out alone was the only recourse I had which brought up several other problems. One of which was if I did present as a successful woman sitting by herself at a busy bar, always invited trouble because I was so out of place. It was during those times that I used my cell phone as a prop. In essence signaling to people, I was waiting for someone to arrive and join me. Plus, in the cold winter months, I could place my coat or jacket on the seat next to me to act like it was occupied. Both of which helped keep away any unwanted advances from mainly intoxicated men. On the other hand, other intoxicated ciswomen did not count, and I welcomed any of their advances which completely outnumbered men. Mainly because the women were so curious about what I was doing in their world.

Another problem I had was a huge case of impostor syndrome I suffered from. No matter how nice the stranger approaching me was, somehow, I felt I did not quite belong in the new exciting world I was in. It took me a while to get adjusted to the fact I was succeeding in a life that I had previously only considered a dream. I also still considered myself a rank amateur because of how I was able to conduct myself as a new transgender woman. I knew very little about how ciswomen communicated in the world away from men and it showed. For the longest time, the little nuances women use to communicate escaped me. Forcing me into shutting down and just listening to others and sometimes coming off as a standoffish bitch. Which was the last thing on my mind to happen.

I began to move away from being a stranger in a crowded room when I began to have enough confidence in myself to move forward. I was no longer just an virtual impostor just observing the world to jump in and inserting how I felt about things and people around me. A word of warning though, it took me a while to get there. Too much trial and error before I gained the confidence in my own unique form of womanhood which differed from many other women around me but at the same time, was still as complete. Sort of.

It was not until I began to build up my own circle of friends who happened to be mainly lesbians did, I began to relax and truly enjoy myself. I was no longer an imposter but now a full-fledged participant in my resurgent social life. Probably the only mistake I made was when I did not realize how different two of my friends were who I kept inviting to our impromptu meetings at sports bars and lesbian mixers. I was still naïve to the lesbian culture and did not realize the differences between a so-called gold star lesbian and one that had been with a man. I had one gold star friend along with another who had been previously married with three kids, so on occasion sparks did fly. In the meantime, I was off in my own little world jumping at the chance to be a wing person for one of my friends and trying to set her up with another woman at the mixer. It never worked, but I had a fun time trying.

The best part was I was no longer a stranger in a crowded room. I was becoming a full-fledged participant and loved it. The only problem I was having then was my new feminine life was starting to seriously force my hard-earned male life into an early retirement. A retirement he was so not ready for. Often the gender conflict I endured was mental and brutal. I did the only thing I knew to do and that was to internalize my feelings and move on. Which was the last thing I should have tried to do. My male self-wanted to keep me being a stranger in a crowded room so he could have his way. What he did not count on was, the more I worked on my dream gender life, the bigger and more accepting the room became.

The more I think about it, the more I think my male self-wanted to keep my female self as a kept woman. Validated by him only. Eventually, my transfeminine soul won out and he needed to face the truth. He was always part of living a lie in my life. Since my impostor syndrome was for the most part gone, it was the last remaining significant part of my life for him to cling to.

It felt so good to no longer just to be going out to be alone and know I would have the chance to meet my friends or even make new ones. Because I had hid my true self away for all those years, my transgender dream self could not wait for a chance to live and express herself in a crowded room.

 

 

Monday, November 3, 2025

What Was I Walking Into

 

Image from the 
Paris Photographer
on UnSplash. 

Many times, in my life, I have wondered what I was walking into. Sometimes, it did not have anything to do with being transgender but many times it did. And sometimes I was wearing high heels which I was not used to which increased the risk of what I was doing.

The main time it did not was when I went into the Army during the Vietnam War. I had no idea what basic training would have in store for me except I would need to get in better physical condition. I did make a half-hearted effort at trying but failed miserably and gave up. On another negative side, I knew I would have to give up all my cherished cross-dressing activities for the next three years of my life.

It turned out, in the scheme of life, three years did not turn out to be that long as traveling the world to three continents kept me plenty busy and I grew used to the idea of not knowing what I was walking into. So much so that I adopted “Call me the Breeze” by “Lynard Skynyrd “as my official song when I was on the radio. Because I was always rolling down the road. Through it all, I learned that my affinity for women never changed. I wanted deeply to live in their world and all the running I was doing would never change that. It was a lesson in life I wished I would have listened to later.

When I served my three years in the military, my restless spirit continued to dominate me and caused me to try to outrun my gender issues. I constantly was trying different jobs in different places unsuccessfully trying to run away from being transgender. Sometimes I had secret agendas, sometimes I did not. Like the time we moved from Ohio to New York City. Somehow, I thought being closer to a more liberal populace would help me to be able to come out of my gender shell. It did not work out that way because of several different reasons which would take another blog post to explain.

Another idea I had which actually worked out better for me was the time we moved from a very rural area of Southern Ohio along the Ohio River to Columbus, Ohio which was a couple of hours away. This time, I knew for sure that I could get back in contact with the friends I had made in years previous at the gender diverse parties and mixers I was going to. I was successful and reestablished myself with the group and tried to make up for lost time and at the same time, settle down.

When I did settle down, I was able to start exploring the feminine world as a transgender woman which meant almost nightly, I was walking into new situations I had never seen before. From gay and lesbian venues to big sports bars, the world was new and sometimes scary. Again, “Call me the Breeze” should have been my theme song due to all the new situations I was facing. Anything I enjoyed doing as a man, I tried to do as a woman to see if I still enjoyed it. Spoiler alert…I did and kept on trying more and more new situations to see if I could handle what I was walking into.

On the flip side, I am hesitant to recommend this type of transgender lifestyle to anyone. Too many times, I boosted my confidence through alcohol abuse and was fortunate to have never caused any major problems all the time I drove when I shouldn’t have. These days I barely drink at all and never drive when I do. The other problem comes from the increasingly nasty anti-transgender reaction which will undoubtedly be stirred up again in the upcoming elections by the orange Russian asset’s minions across the country. We have a close senate race coming up here in Ohio and I am sure I will see the transgender lies about the Democratic candidate before too long. He has run before, and the television ads were nasty.

Regardless, I am fortunate that these days, I present mainly as old and don’t have many problems walking into new situations. I will have several coming up in the next six months or so to keep me on my transfeminine game. I have an eye appointment at the VA as well as a hematology visit coming up soon as well as another bus tour vacation south in January. Not to mention my mammogram which will be in February this coming year.

It has become part of life for me to wonder what I am walking to at my stage of life. Especially hematology where they are going to do a total blood work check up on how my body is working but I will jump off of that bridge when I come to it. Which is what I have done through most of my life. This time I had to do it without all the male privilege I had built up which as scary.

 

 

Thursday, October 23, 2025

Not a Fetish...A Lifestyle

 

Image from UnSplash. 

I am still always amazed when a bigot or uneducated person thinks a transgender woman dresses as a woman as some sort of a fetish.

In my case, I realized the feminine clothes and makeup I was wearing were secondary to the real reason I was doing it. I wanted to be a woman, or as close as I could come to being one because I knew there were certain things I could never do such as give birth. As I progressed through the years, however, I found I could find my own path to womanhood and follow it. I would have no part of thinking I was involved in a fetish at all. I was different. Little did I know how different I would turn out to be.

Initially, I judged a ciswoman’s life from what I observed, since I was not allowed into experience more. When all you have is a one-sided view, all you get is a shallow result. All I could see was the pretty clothes, shoes and hair that the women around me had. Why did I have to be stuck in my same old shirt and tie when my cousins at Christmas got to wear their new velvet dresses, shiny black shoes, and creamy tights. I was always so disappointed when we left for the trip home, and I dreamed of the day I could be a woman.

For many reasons, I took my time getting to my dream world. It was almost fifty years later when my wife Liz and I took in a Cincinnati Symphony Orchestra Christmas concert, and I was the one who needed to come up with the most beautiful semi-formal gown I could to blend in with the other ciswomen and enjoy the evening, I did as I thrift shopped diligently until I came up with an attractive, sparkly gown in my size. Happily, I brought it home and it worked well as I blended right in. Without a fetish in sight.

The only time I had to deal with being a fetish object was when I first came out into the public out of my closet and tried online dating. At first, all was pretty quiet on the dating front until I began to try the “man seeking man” sites. Since I never kept my transgender status a secret, I began to be flooded with men who wanted to wear my used panties or just meet up in a motel room some place. I even had a couple of men who wanted me to dress them up as a woman. Naturally, I turned down all those requests and was stood up often when I required meeting a man in a public location of my choice. Even though I was intensely lonely, I knew I was more than a fetish object and had to be safe in the new world I was in.

The longer I followed this route, the more I knew I was headed towards a complete gender lifestyle change. My dream was more than a dream and it could be a reality if I tried hard enough to reach it. But first I needed to change who I was trying to reach in the world. When I started out, I thought men would be my focus. All the way to having one woman friend tell me to get a banana and practice. (I will let your imagination do the rest.) As I progressed though, I discovered the opposite was true, in order to make it in life, I needed to first be accepted in the world of ciswomen. Who made it a practice of looking me over from head to toe when I went out in the world. They taught me how to be better, because I was certainly not a fetish object to them. I was locked into a scary, exciting new transfeminine lifestyle.

When I became a regular in certain venues, it helped me jump the gap I was experiencing when someone just saw me for the first time and thought I was a man in a dress. When they saw me for the second time or more, they began to realize I was a lifestyle, no matter what I used to be. The world opened for me, as well as the ciswomen around me who taught me I did not need validation from a man to feel good about myself.

As day-to-day transgender women, we do face the improbable battle with trans porn in the world. Men think we are all like women they see in videos, and magazines. When the men find out we are not the fetish objects of their desire, some react violently. Trans women have enough threats to face without the extra problems of trans porn.

As soon as the government leaves us alone and realizes we are just living our lives, not as fetish objects, the world will be a better place to live. Our transgender reality is what we are fighting for.

 

 

 

Sunday, October 19, 2025

Taking a Break from the Elephant?

 

No more Elephants! JJ Hart,


Taking a break from the elephant? I guess finally I am.

This morning, with groceries running low in the house, my wife Liz and I decided to run out in the rain to our nearby coffee shop to grab coffee and a breakfast snack. Since I was not anticipating meeting anyone else in the world, I just grabbed my purse and headed out the door with Liz. No makeup or anything since we were just going through the drive through. When we returned home and in a dry space, it occurred to me that I had retired the elephant in the closet of my life.

Excuse my language, but that damn elephant has always been a part of me for as long as I can remember. It was somehow a part of every decision I made. I could not take a break if I wanted to. If I was on a vacation with my second wife, I could not relax because I was thinking so much how I would feel if I could do it as a woman. Usually, after the vacation was over, I just wanted to get back to work to take my mind off the elephant in the room…my transgender issues.

I finally came to a point when I quit worrying about who I was gender-wise. I was just me and that had to be good enough. Surely though, I needed a lot of help to make it to that point in my life. I was deeply insecure about my transfeminine self and needed whatever public reassurance I could get. More than not, the reassurance came from having no feedback at all when I was out in the world. No laughing or staring to ruin my entire experience. I just could not take any sort of break until I became better at my public presentation all the time. I was still two people trying to come together.

All of this extended over to my writing which at this count is over seven thousand posts over ten years on one platform I write on. On occasion, I go back through my earlier posts to see what if there were any changes there were.  When I did, I was amazed at how centered in I was on my feminine appearance and not much else. I still had not learned what the elephant in the room was trying to tell me, there was so much more to being a woman than my appearance. I could not take a break until I learned that ciswomen lead a more difficult, layered life than men, and I needed to adjust and do better if I was ever going to really succeed.

I don’t think I truly conquered all of my fears of merging my worlds together until Liz and I began to take bus tour vacations to various parts of the country. Primarily, when I needed to stand in line for the first time in many years with other women waiting to use the restroom. The entire process tested my new outlook on the world in a space which was considered a women’s only environment. I remembered what I learned from all my past experiences, did what I had to do, washed up and left. With no adverse feedback from any potential haters or bigots. I was just me using the restroom.

With all of that behind me, I began to relax even farther and enjoy all the new scenery the trip had to offer, for the first time as me. I was on my own and to hell with the elephant which had taken up so much room in my closet. Another chapter in my life had been closed. The only break I took was from my daily writing routine, to allow myself a chance to recharge my batteries and hopefully do a better job which I had never been professionally trained at. I just started writing to hopefully help others with similar issues.

These days, since I have retired from my elephant and am still taking a break from all the problems and commotion he caused, sometimes I don’t know how to act. After all, I needed years to rebuild the damage he caused. Taking a break, now, means a lot more to me than just taking a vacation. I am sure before the next adventure we take; I will still feel the same residue from past gender world mishaps I needed to overcome and move forward, but at least I don’t have to ruin my days worrying about it.

It is much easier to pack for a trip for just one person. The only person which really mattered all along which makes taking a break much easier to do.

 

 

Seeing It All Clearly Now

  Image from Lola Rose on UnSplash.  As I journeyed for years along my decades old gender path, I discovered I could see life much more clea...