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.”

Solving the Gender Puzzle

Christine Jorgensen. 

Many times, during my life, I have looked at my gender issues as having a big puzzle to solve.

From my earliest age of recollection, I can remember thinking that something about me was really wrong, but I could not put my finger on what the problem exactly was. Most likely, it was not until I began to have a fascination with my mom’s clothes did, I began to discover what the puzzle I had was really all about. At that point did I embark on a lifetime journey or path to figure it out. I had no idea of all the twists and turns my path would take me on until I could finally put the pieces of my gender puzzle together.

Perhaps the biggest part of the puzzle to me was the fact that I was born into a male world with no way out in sight. I lived in a rural area around the same kids growing up from kindergarten through ninth grade, so I figured no one else had the same puzzle to solve that I did. Plus, in the pre-internet days, when I was growing up, there was no easy way to access any outside information. Especially none as radical as having anything to do with gender issues. As close as I could come was sneaking a look at all the “National Enquirer” type trash rags at a friend of mine’s aunt’s small neighborhood convenience store. Every once in a while, they would run a sensationalized story about “Christine Jorgensen” or another G. I. who wanted to change his/her sex. I remember the first time I saw one of the stories, I was hooked and could not wait to go back and look for more stories.

In some ways, just looking at these stories made finding pieces to my puzzle even more difficult to do. There was just no way I could ever see myself ever arriving at the point where I could go through such drastic measures to be a woman. I would just have to rely on my dreams to give me hope of ever living my life the way I wanted. Which of course was that of a transfeminine person. Hell, the word did not even exist back then in the sixties and having any sort of gender dysphoria was still considered to be a form of mental illness. Any hope of piecing together my gender puzzle would somehow just have to wait. For a bigger problem called military duty.

As I entered my formative years of high school, the Vietnam War was still escalating and the government had to establish a military draft to fill the ranks of unwilling participants, which included me. With all the stress hanging over me, I went off to college to at least prolong the draft position I had for four more years. Surely, the war would be over by then, but it wasn’t and it was my time to serve in the Army. I had the dual problems of not wanting to experience a military career from what it might do to me along with the problems I would have expressed any of my gender issues which I was just starting to do when I was drafted. My one certainty was miniskirts on soldiers would be frowned upon in Army basic training. Any work on my gender puzzle would have to wait for three long years.

Three years later, I survived my military service much better than I ever thought possible. I got to travel the world on Uncle Sam’s dime and even was able to experience the beautiful, exotic “Lady Boys” of Thailand when I was stationed there for a year. Even though I was fascinated with their culture, I was never brave enough to approach. Much later on, when I was in Germany, I gathered my courage to go to a hospital Halloween party dressed head to toe as a woman which led me later to my first coming out piece to my puzzle. Over huge amounts of good German beer one night, I admitted to three of my closest friends that my Halloween “costume” was more than a one-time deal. I was a transvestite and was attracted to dressing like a woman. Luckily for me, no one else cared and my secret was safe for the remaining six months I had to serve in the Army.

After I had served my time in the military, piecing together my gender puzzle became a bigger priority. Initially, I needed to rely on Halloween parties every year to express my need for public exposure as a transgender woman as by that time, I was realizing I was much more than a cross-dressing part-time guy. One of the biggest “aha” moments of my life came the night I made the mental shift from cross dresser to transgender woman and went out into the world. Despite being scared to death, I made the evening a success and knew deep down there was no going back. I had found a giant piece to my puzzle and I began to wonder what took me so long.

From then on, the pieces to my giant puzzle began to come together quickly as I began to carve out a life for myself in a world of cisgender women. To this day, the path I took seemed like a blur and once I began rolling downhill towards living my dream I could not stop. I was going crazy looking for the final pieces of my puzzle until I discovered the magic of gender affirming hormones or HRT. The hormones evened out my testosterone poisoned personality and enabled me to feel emotions I never realized I had. For the first time ever, I was able to feel the feminine way I tried so hard to appear like.

I have never been good at puzzles my entire life and find them to be exceedingly boring and frustrating…except my gender puzzle. Even though I don’t think I will ever finish it in this lifetime, the amount of work I put into it turned out to be very satisfying and just what the therapist in me ordered. I was able to finish to the point where I could see myself in the puzzle and was satisfied with what I saw.

  

Making the New You...You

 

JJ Hart

Making the new you… you probably know is a lot more than putting on a dress, wig and makeup.

Most of the time, it takes time to grow into what you always had thought yourself to be all along. A fully feminine person. By that, I don’t mean you have to go out and have major gender surgeries to feel complete although many transgender women do. In my case and at my advanced age of seventy-six, I have long since given up on gender surgeries because they don’t define me. But that is like HRT or gender affirming hormones, just because you can’t take them does not make you any less of a transfeminine person.

Going back to my original point, I think it is important that we take the time and opportunity to grow into our new authentic selves which have been a part of us forever. I know forever is a big word which people like me have run from our entire lives. It is especially frustrating when you discover the truth has been right in front of you forever. Instead, I took the long route or path of slowly discovering I could indeed make it to my dream of living life as a transgender woman. I had to go back and back fill my entire personality and outlook on life to do it.

In the book I am writing through another format for my daughter and other family members who have questions about my life. This week’s topic is what I would do differently if I had a chance to go back and do it again. It was an easy question to answer; I would certainly go back and transitioned earlier in life than I did. The problem I have with thinking this way is I am selfish and I would want certain aspects of my male life to live themselves out before I made the big gender jump across the border for good. For instance, I would hate to give up my stake in having my daughter who is one of the greatest gifts of my life. Plus, you can’t forget the world and its reaction to transfeminine people was much different back then and if I transitioned then I would consider surgeries to advance my standing in an often-unforgiving world. Chances are, I would, simply because I had so much longer to live.

It would have been interesting because back then, I had such little understanding of what I was really facing if I continued along my gender path. I was still laboring under the impression that a pretty face would be all I needed to get by as a trans woman. There was still so much to do to enable the authentic me to emerge into the world. What would I do when and if I needed to have the pretty face actually communicate in the world with other humans. I had come to the point where I could make her move more convincingly as a woman, now I had the biggest jump to make. I did the best I could. Even to the point of taking vocal lessons on the small ways ciswomen communicate with the world. The entire process was intense but worth it.

The only way I made it through the rebuilding process was to make it a completely selfish pursuit which I spent every spare moment thinking about. My male time in life shrunk to a bare minimum, or just enough time to get by and keep him moving on the essentials of life such as a job.

On the feminine side, I found I had help from understanding ciswomen that accepted me. I write about them often. Emphasizing their warmth and humor when at the same time were the best gender teachers I could have ever asked for. Together, they all helped the new me be me and move on from there.

From there meant I could begin to attend “meet up” groups in the Cincinnati area with my wife to be Liz. We went to writers’ groups as well as artisan/crafts groups which helped me to come farther out of my gender shell and just be the new me. If you live in an area which has groups such as meet ups, I highly recommend them as vehicles to experience new vistas of your gender experience. I always looked at them as a way to expand who I was in the world as I shed my old male past. Which led one step farther into a spiritual group which Liz was already a part of. I was invited in with open arms which gave me yet another new outlet to experience.

Making the new you, you will never be an easy experience depending on how much gender baggage you had to shed along the way. The longer I waited, the more I had to figure out what to keep and what I needed to get rid of. Whichever way you decide to go, just try to make the best possible decisions and keep moving towards your dream. Just think, your whole journey could be a labor of love.

 

 

Practice, Practice, Practice

 

Image from Mor Shani
on UnSplash. 

Sometimes I wonder if some people don’t take the time to understand how much practice I needed to do as I became my authentic self. I guess I could say I went through nearly a half century of work to become who I dreamed of being. It was far from easy.

Starting at the beginning, I never had much to work with as far as being an effeminate boy. Not to mention, I was born into a very male dominated family. Very early I learned I was going to have to work hard to not look like a clown in drag when I tried my best to look like a pretty girl in front of the family mirror. I always equated putting on makeup with painting the plastic model cars I had. Which I was always very bad at doing.  

It did not help when I earned my own meager amount of money working around the house or delivering newspapers in the neighborhood. Then I used the money to try to shop for makeup. I still remember to this day, the first time I was confronted by the sheer number of various makeup brands and variations to try. I finally selected several products out of desperation and hoped for the best as I was trying not to use my mom’s makeup anymore. Now, I don’t remember how successful I was, but I kept on trying to practice on my face until I got it right. Or so I thought. It wasn’t until years later that I visited a true professional makeup artist that I discovered I was not working on the true potential of my makeup to its maximum effectiveness. I was merely making the same basic mistakes over and over again.

I was fortunate to have the makeup artist who was able to explain to me in terms of understanding what he was doing, so I could repeat the process later. Practice for once made perfect. I was able to paint my model cars in a way that my friends admired them. But this time, I was actively admired at the crossdresser-transgender social mixer I was at, and this time when I tried to hang out with the “A” listers (as I called the beautiful, more advanced crowd of attendees) I was accepted. The best part of the whole evening was I then had a basis of where I needed to be as far as being an accomplished cross dresser but on the other hand, I was presented with a deeper set of questions about what I was going to do about my male life as I knew it.

What I decided I had to do was take my transfeminine show on the road so to speak and see if it would play at all in the public’s eye. Away from all the safety of mixers and gay or lesbian mixers. That is when the real practice set in. I needed to stop all of the hard-earned male muscle memory I had learned and start to learn the best that I could the graceful, fluid moves of a cisgender woman. Naturally, the whole process was difficult to do. Especially when I was switching back and forth between the two main binary genders almost daily. Constantly, I needed to remind myself of who and where I was so I would not end up at the wrong place at the wrong time.

Through it all, when I thought I was being successful in going down my transgender path, roadblocks always emerged which sent me back to my drawing board and started setting up more practice. Those were the days of taking every spare moment I had to sneak out of the house and begin to carve out a new life for myself as a trans woman. Once I made it successfully out of the gay venues I was going to and into a few of the big sports bars I was used to going to as a guy, I started to relax and enjoy my new exciting life even more.

No matter how much I try to gloss over this part of my life, the fact still remained I was essentially cheating on my wife when I went out as myself. Deception was never my strong suit, and I was never proud when I needed to lie about what I was doing. By this time, I had reached the point of no return but still was afraid to face it. I hid it by staying in the so-called practice mode I was in. If I could have just one more experience being a transfeminine person, it would make it so much easier when I decided to permanently put my old unwanted male self behind me for good.

Finally, I quit kidding myself, and I was doing so much than practicing over and over again to live a transgender life. I had always dreamed of doing it, so it was time to do something about it and live it. Who knows, maybe all that practice at living a feminine life saved me in the end as I finally learned to move and communicate my way around in a ciswoman’s world.

 

As the Clock Strikes Midnight

 

JJ Hart

New Year’s Eve is upon us again.

With it comes a flood of memories, some good, some not so good from both sides of my transgender border. First, let’s remember one of the ugly male experiences I had. This came from years ago when I had completed my tour of military duty and we were celebrating that as well as the New Years.

Being the huge drinker that I was, I ordered a keg of beer and a bottle of mezcal for a smallish party my second wife (to be) and I were having. Too much booze it seemed to stay socialized at all. To make a long story short, after a hard night of trying to drink the mezcal and the barrel of beer, when the clock struck zero and the ball in Times Square dropped, I did not kiss my future wife first, I committed the ultimate sin of kissing her more attractive sister. Needless to say, there was no way to hide what I did, and I was in deep trouble no matter what I had to say about it.  The damage was done, and I would have to live with it for years. In fact, I don’t think I ever lived it down.

I could blame the entire unfortunate episode on toxic masculinity setting in, but in fact, I was trying desperately to bury any thoughts that I had of being a woman on yet another New Year’s Eve. From then on, the yearly debacle which was a party on New Years went on by me in a blur. At the least I proved I could outdrink anyone else and at its best I learned the problems of acting like a fool and being careful to kiss the right person at the right time.

Nothing really changed until I met my current wife Liz approximately seven years ago when we went out on the town in downtown Cincinnati for a New Year’s Eve celebration. We began with having an Uber ride to our first destination, which was the Cincinnati Music Hall for a performance of the symphony orchestra. Even though I thought I was dressed appropriately for the occasion in my black sequined gown, I was still very terrified about going at all. It turned out that once again all the worrying in the world did not help me at all because nothing happened. I went, I blended and I conquered all those around me who may have questioned having a transgender woman in their midst. And probably, the best part was that the night was just beginning.

From the music hall, we took a terrifying taxi ride in a cab company called Einstein Taxi (really). He drove us at breakneck speed to a venue where we had dinner reservations down by the riverfront. Once we safely arrived, we did not have to wait long to be seated and once again I was met with no resistance to being me at all. The venue was also a micro-brewery which featured German food, so we ate well as we waited for the ball to drop on a New Year. This time, I made sure I was kissing the right woman. Liz of course, before it was time to head back home and no, we did not drive.

This marked the first time I can remember I did not have the thoughts of failure hanging over my head. I was not going to spend another year as my hated male self again. What a relief!

This New Year’s we have a huge college football game to watch as The Ohio State Buckeyes play Miami of Florida. Since the game does not start until seven thirty, we will have plenty of time to open a bottle of wine and toast the incoming 2026. Without dwelling on all of the problems the transgender community had heaped on us in 2025, maybe the upcoming year will be the one when the rest of the world says enough is enough and the upcoming mid term elections will sweep the evilness and the liars out. It is the country’s two hundred fiftieth anniversary. It is time to reclaim some of our past which made us great.

That is my hope for the New Year, as well as I hope you have a better year too, no matter what your goals and dreams might be. I will be spending it in the comfort of my own home with my favorite person who did more for my male to female gender transition than anyone else. It does not get any better for me and I don’t have to worry about who I am going to kiss.

Happy New Year’s!

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.

 

 

 

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.

 

 

 

 

 

 

 

Fearing Change as a Gender Challenged Woman

Image from Joshua Gaunt 
on UnSplash. 

Gender change came so very slowly for me during my life.

First, I needed to free myself from the male bonds I was born into which I had no control over. Looking back, I think one of the main problems I had was fearing the changes I was looking to go through if I faced up to reality. From that point forward, life became a struggle as I feared changing it.

What I became was the best transgender procrastinator I knew. Any excuse I could come up with not to go through with living my dream, I clung to like a survivor on the Titanic. What I would do about spouses, family and employment were a few of the major questions I was asking. So, what did I do? I ran as hard and as fast as I could from the problem. I was running so hard, I even changed jobs very quickly so I would not be bored with my life as a transfeminine fugitive. Eventually, even though I grew tired of the pace, I found a stable good job and settled part of my life down. I say part of my life because during that time my gender issues were raging out of control.

Even though I was slowly becoming successful at blending my feminine self in with the world of cisgender women, I still had many fears to conquer. Just when I thought life was improving for me, I would hit another roadblock and send me running back to my cross-dressing drawing board. Which was crazily marked with clownish makeup until I got it right. The fear of applying skilled makeup kept me occupied for years it seemed. On the other hand, when I got my male ego out of the way and realized I needed to dress for other women and not men, did I begin to improve my overall look and the laughter I used to receive in public began to die away. When it did, I learned the most powerful force I had to combat gender change was having confidence in myself. Surely, I would never be the prettiest most beautiful woman in the room, but a lot of other cisgender women were not either and they were surviving and even thriving just fine. There were many layers to building womanhood and I just needed to find mine.

For some reason, the more success I felt as a transgender woman, the more fear I had. I guess it was because of my old male self-starting to panic because he was losing his dominance over my life. For years, what had seemed like the impossible gender dream was now looking as if it could become a reality. As he fought his new reality, the stakes towards living a successful life as a trans woman, increased dramatically. Every step I was taking towards my dream seemed to feel as if I was walking in quicksand since at any time, life as I knew it could be disrupted beyond repair in the little backwards town I lived in. I still lived in mortal fear that any day I could be discovered and the acquaintances I had built up over the years would realize I was living a gender lie. Which I was.

I finally made it to a point where I could not procrastinate my life any longer and I began to use every spare moment to explore the world as a transfeminine person. It all meant I accepted the challenge to finally go all in with making the final preparations for my new life. The bittersweet part of it all was part of my male to female final transition was built on tragedy. In the space of a couple short years, I lost my second wife as well as all of the friends I had built up over the years to death, and I had to start all over again. Sure, I was still afraid to do it but deep down I knew transition was the only way I could go. Suddenly it was up to only me to decide if I wanted to take the ultimate step and try to get a doctor’s permission to begin HRT or gender affirming hormones. I was approved and then the changes I was hoping for began to really happen for me. The changes were so dramatic, I sometimes take an entire blog post to relate them to you.

What frustrates me now are the haters who say that because I took so long to transition, I am not trans enough for them. Normally, they are younger LGBTQ individuals who have no idea of what the world was like way back when I was growing up. We all have our own gender crosses to bear, and we need to understand each other’s journey.

Sadly, there are all those transgender women and trans men who can’t take the burden of gender change fear any longer and tragically try to take the self-harm way out. The suicide rate in our community is completely too high and could come down with proper help and understanding.

In my case, my excuse is I had a heavy dose of ignorance combined with fear and procrastination as reasons it took me nearly a half a century to come out of my gender shell and live freely in the world as a transgender woman. These days, if you can steer clear of all the online trolls and haters, you can still get valuable information on the internet concerning ideas on how to build a new life as a woman from scratch. Plus, fear for me was a powerful motivator and when I was forced into a corner because of my gender, I came out fighting because I believed I was right.

It turned out I was.

 

 

 

  

Resolutions

 

Image from Nik on UnSplash.

I am a firm believer that most new year’s resolutions are made to be broken. Statistics say that nearly eighty percent of people never keep resolutions.

On the other hand, in my formative transgender years, I ended up making several resolutions that I intended on keeping. But by now you might be able to guess which ones I am talking about. The further I was going towards being able to live the feminine life I always dreamed of, the easier it was for me to set new resolutions to conquer in the upcoming year ahead.

Very early in my gender journey, it was easy to set easier goals such as getting out of my dark closet and into the world. I figured from there I could look around and see what was next. What was next proved to be terrifying, natural and exciting all at the same time. More and more I felt bored by the old idea that all I wanted was a chance to be a woman on my own terms. It got to the point where I did not have to make any resolutions which I would have to break. I was doing a good job at living out the ones I had already made. Ironically, I missed several resolutions I should have made but did not. Such as when I did not see my second big gender transition coming at all. It was when I shifted gears mentally and began to think of myself as being transgender and not a cross dresser at all. To this day, I have nothing against all cross dressers (since I was one for years) but my gender needs took me deeper.

Of course, going deeper into my transgender rabbit hole, brought out the need for new resolutions. The old shallow ones such as could I exist in a ciswoman dominated world no longer were making it. I was way past all of that and needed to find out once and for all if I could carve out a new life for myself that I had only dreamed of. You might say, reality of life began to outstrip my dreams as well as the need for more resolutions. At that point, I quit making them all together.

It was easier to go free form in my transfeminine pursuits and do the best I could. It turned out that for the most part I was successful and continued on feeling good about myself. Until the usual problems arose with my unapproving wife and a male self who continued to dominate a big portion of my everyday existence. As I thought more and more about them, I wondered what I would ever do about setting up more resolutions about changing my life for good and jumping the male to female femininization border.

I don’t think until you have walked a mile in our high heeled shoes as a transgender woman would you understand the relative importance of making new year’s resolutions. While others are thinking about losing weight or cutting back on their drinking, you (on the other hand) are wondering what in the world are you ever going to do about becoming a full-fledged transgender woman. It is especially difficult when someone you know asks you what your resolutions are and you don’t want to lie.

At that point, I just went back to my default position I used when anyone asked me about my future. When I was a kid, instead of saying one day I wanted to be a woman, to please my parents I just said I wanted to be a lawyer or doctor. Seemingly, nothing changed later in life when I was asked about my resolutions, I would just say to lose more weight or make more money. So, I lied and took the easy way out. There was one way I could tell the world the truth at that point in my life. Then I started to wonder how many other people who spoke of their resolutions on new year were fudging their answers too. All those people who rushed out to join a gym never really meaning to go like I did once. As I think about it, going to workout in any shape or form was yet another gender smokescreen I threw up to disrupt anyone who was sensing my transgender issues.

Overall, I wonder how many other trans women or trans men have had to try the same method and any sort of a public call for a resolution or two is just another way to hide while you are on your path. One of the statistics which I have read on resolutions said that only twenty percent of people making resolutions keep them anyway, so I don’t feel so bad about not making them anymore. And who knows how many of those making resolutions are closeted transgender people anyway?

Looking back, the only advice I could give to a trans person still in the closet thinking about the new years and making resolutions is to try to make yours doable and don’t try for too much. Failure only leads to disappointment and a deeper return to your closet.

Anyway, you cut it, a new year is on the way, and we have a chance to sweep away a very disappointing 2025 out the door. Just keep your head high and hope for the best in 2026. At the least we will have a chance to vote and change a very crooked regime in Washington. Something you can do from the privacy of your closet, and no one will have to know and if you do make resolutions and don’t keep them you will be in the majority of the population for a change. A real rarity.

 

 

 

 

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.

 

 

Acceptance...all that And More

 

JJ Hart.

Just a short post this morning since I was out and about with my wife Liz to medical appointments and more.

This morning, I got up early to go with my wife Liz to her doctor’s office appointment. Per norm, I did not expect much interaction with the public since we were going at such an early hour. So, I could keep my feminine prep to a minimum.

I kept my prep to a close shave and brushed my hair along with leggings and sweatshirt top and I was ready to go. With my rain boots along with the wrap my daughter got me for my birthday to keep the cold wet away. As Liz went to the receptionist at the hospital to be checked in, I grabbed a nearby seat to sit and wait, and the receptionist very much ignored me one way or another. I was off to a good start as all of the other people who followed us into the large waiting room were off in their own world and ignored me also.

As I was playing on my phone as I waited for Liz, I began to think about how far that I have come over the years when it comes to being accepted as me, as my true self. I used to obsess on my appearance when I went out and about at all, until I noticed I was the only woman doing it. Gender acceptance was as important to me then but was still somehow different. These days, my acceptance level seems to be at an all time high which is great for my continued confidence as a transgender woman.  I will certainly need all that I can get when Liz and I take off again for another extended vacation south from Ohio in the latter part of January. As always, my paranoia stems from using the women’s room in the states we travel through which frown on it.

Through it all, I keep telling myself this is the fourth or fifth tour we have been on, and I have never had any restroom problems, so why start now.

Other than that, we don’t have much going on except I have a mammogram in February.  It is hard to believe the winter will have moved on so quickly from me. Especially at my age, it is sad to see life moving by so fast. 

Back to the present, to reward Liz for getting her flu and pneumonia shots, we went through our favorite coffee shop, drive through for warm coffee drinks and a light breakfast sandwich and the girl at the drive through window said, “you girls have a nice day.”  With that comment, she made sure I did.

No matter how long I live my dream of being a transfeminine person, reinforcement from a stranger is always great acceptance and more.

 

 

 

The Hustle and Bustle of Christmas as a Transgender Woman

 

Image from Clarke Sanders
on UnSplash.

Doing the Christmas shopping shuffle as a transgender woman, often takes a lot of courage and confidence to do it.

Over the past couple of weeks, I have written about my holiday adventures leading up to the big day. From taking a short trip to Clifton Mill to view their extensive, festive lighting display all the way to letting two men load my heavy purchase for me at an Oak furniture store, I stretched the boundaries of what I was used to as a new cross dresser or trans woman in public. After it was all said and done, even though I was terrified most of the time, I was happy I tried it all. I came out of doing the Christmas shuffle with much more confidence in my girl self than I had going into the season.

In fact, as I have written before, Christmas quickly outpaced Halloween as my favorite holiday. Why? There were several factors, such as the length of the season and the creativity I could put into celebrating it. Plus, for once, I was doing good for others by buying gifts for them as I shopped. I positively loved it and wondered where the experience had been most of my life.

If you are a procrastinator and last-minute gift shopper like I was, doing the Christmas shuffle as a transgender woman is ideal for you. As you can get lost in the crowds quite easily and no one pays attention to a single woman out doing her late shopping. Custom made for you to do your shuffle and head back home.

I was fortunate when my second wife left her bookkeeping job and took a managerial position at a large bookstore chain. So, at Christmas, she was very busy and worked many hours. It was easy for me to schedule my hours around hers, so I had plenty of time to get out of the house and do gift shopping. I could obsess on wearing just the right outfit to blend in with a busy world and at the same time, search for just the right gift. Along the way also, I could stop in and grab a bite to eat at a restaurant and again stretch my ability to deal one on one with the world as a transfeminine person. Yet another reason, I came to prefer Christmas over Halloween because I hoped I was not perceived as a man wearing a costume, or worse yet some sort of drag queen.

As the big day approached, the sky was the limit for me. I did my shuffle as much as finances allowed and stockpiled my gifts for my special night where I stayed home with some high-powered eggnog and wrapped my treasures to go under the tree if they would fit. Of course, my wife was close to being a professional gift wrapper and I was just the opposite. But as the eggnog kicked in, I did not care, and besides it was the thought that counted. Right?

Finally, the big day arrived and I was shuffled out. Plus, we had family connections to visit all day on Christmas day. My thoughts for once were in other places than doing my precious shuffle which I had learned so much from. After the day wound down and my wife and I were alone, we opened the final gifts from each other. Which included a gift for my feminine self. I will forever remember a nice fancy fuzzy baby blue sweater she gifted me. It was snug fitting and I filled it out nicely with my new silicone breast forms I received from a cross-dresser acquaintance of mine who was purging. Naturally, that part of our gift giving day was the part of the day which was the most anticipated for me. I was like a little kid, brimming with anticipation.

Every year after the intense transgender Christmas shuffle was over, I had the chance to sit back and reflect on all my experiences and what they meant. Without hesitation, I think the confidence I built up from going out in the world as my trans self was the most important aspect of what happened to me. I learned what it meant to blend in with ciswomen around me and survive better than I ever could before. I also discovered the vast majority of the world did not and does not care about having a transgender person in their midst. The biggest difference is that back then, we did not have a Russian asset in the White House leading his blind, spineless party into demonizing a small portion of the population. Back then, I was merely a curiosity to many people, especially ciswomen.

When my second wife passed away, the need to do the major Christmas shuffle went with her too. The only blood family I had left was a brother and a daughter to worry about at all during the holidays. When I came out to them, I was roundly rejected by my brother and completely accepted by my daughter and her family. So, I broke even and even did better when I considered the relationship, I was able to build up with my daughter, son-in-law and three grandchildren. I won the family coming out shuffle in a big way.

Even still, sometimes I miss the hustle and bustle of doing the transgender Christmas shuffle as over the years, I have gone nearly the entire direction in the other way. It is hard to say what I miss most but it probably having the financial resources to buy basically as many gifts as I could afford might be it.  Maybe it all came from having a guilty conscience from sneaking out of our house to join the world as my authentic true self instead of my old boring male self and breaking the pledge, I gave my wife that I never would.

Whatever the case, I was extremely selfish and was a contradiction when I did it to buy gifts for others. I guess it fit in with the whole contradiction I felt from my deep-set gender dysphoria to begin with. I dealt with it all the best I could, did my Christmas gender shuffle and moved on with my life making the most of it.

 

 

Earning my Way into the Sandbox of Women

 

Image from Juli
Kosalapova on
UnSplash.

I call being accepted in the feminine world of ciswomen around me, as being able to play in their sandbox.

Getting a chance was similar to living a dream and very difficult for me to do. To begin with, I needed to lose whatever weight I could off of my very male dominate frame and take better care of my skin, so I could use less makeup. I desperately wanted to be pretty but accomplished it as naturally as I could. Motivation to do both came easily for me because I was obsessed with doing something very well in life that I cared so deeply about. Surprising even myself, I was able to shed nearly fifty pounds as well start moisturizing daily after I shaved. Obviously, the weight loss helped more dramatically when I could shop for a better selection of stylish women’s clothes in my new size and the decrease in makeup I needed spoke for itself when I presented better in the world.

Even with those positive results behind me, I was still very naïve and had very little knowledge of what I would have to do to be let in to play in the sandbox by the alpha female gatekeepers. As my second wife was always fond of telling me after major fights, we had that I made a terrible woman. Then she added she was not talking about appearance. Which was good since I had just had situations where I was mistaken for a ciswoman to back me up. Then I was confused, if it was not my feminine appearance holding me back, what was it? What would make me a better woman after all.

From that point on, I set out on a mission to understand what she was telling me but I had a major drawback…I was still living the vast majority of my life as a man and as such, ciswomen would not allow me back behind the gender curtain. For the most part, I was stuck in my part-time cross-dressing ways until I could find a better way out. The sandbox remained a faraway dream.

The main problem remained. My male ego would not easily let me pull down my male defenses to see and learn what really went on in a women’s world which operated quite nicely with or without male influence. For the longest time, he (me) refused to listen to women the best he could to learn what they were really saying when he was stuck playing the game behind the gender border. I felt as if I was in East-Germany behind the Berlin wall of gender. I knew I wanted to escape but did not have the willpower to do it. I was a victim to my newly discovered transgender hopes and dreams. At that point, I still had not realized how far behind my gender dreams being a victim made me and I still felt sorry for myself because of all my gender dysphoric issues.

As I always point out, it was not until I began to experience my version of womanhood in the public’s eye did anything begin to change for me. All the effort I put into my appearance came back to help me get my high heeled foot in the door with other women. Then the real work began when I needed to communicate and interact with them. What happened was many other ciswomen were encountering me on a regular basis in the venues where I always went, so I needed to develop a stable feminine persona to go with my appearance. What would I call myself and what wigs would I wear every time I went out are prime examples of what I am talking about. I was getting to the point where I was staring my forties in the eye and I knew I was not getting any younger and in the back of my mind, I had a sneaking suspicion that I had lived my life all wrong up to this point.

Rather than bemoan all of the mistakes or missed opportunities I had as a male, I needed to face the fact I was wasting my time as a male anyhow because I was always meant to be female. I went home and wrote in my secret diary that I was not a man cross dressing as a woman; I was a woman doing her best to cross dress as a man and build a life on a house of cards.

The realization of my true gender status enabled me to be my real self to the public and ciswomen responded well to my truthful gender identity. Even if they were curious what I was doing in their world and why I wanted to play in their sandbox and work my way into coveted woman only spaces. Finally, I was coming to the point where I could think I achieved my own womanhood, just in a different way than most ciswomen. I was still relevant to the world and should be allowed to play in the sandbox.

Another big lesson I learned was that once I was in the sandbox, I needed to work harder to stay. One slip up back to my old male self, and I would be labeled an impostor and barred from the box. Faced with the task of starting all over again. To the best of my ability, all of my feminine mannerisms, interactions and vocalizations had to be perfect. I was so afraid most of the time until I finally began to relax and have confidence in myself.

The best part about the entire process was I survived to write about it and hopefully to inspire others in this very trying, difficult time to be a transgender woman to make it also. We all have differing yet similar paths to make it to the women’s sandbox. Just don’t expect the process to be all positive and you can make it by hopefully finding ciswomen who knowingly or unknowingly help you along. Those minor claw marks you might receive like I did down my back were just learning marks and helped me along. More than the women scratching me ever knew.

They helped me to earn my way into playing in the women’s sandbox. The claw marks just equated out to the stripes I earned when I was in the Army.