Showing posts with label fashion. Show all posts
Showing posts with label fashion. Show all posts

Friday, October 24, 2025

Growing Like a Weed

 

Image from Marya Volk 
on UnSplash.

I was devastated when I outgrew all my mom’s clothes and I had no sister’s closets to raid for clothes. Where would I ever be able to find the feminine accessories, I needed to cross dress in front of the mirror. So, I had to rely on a little luck and a whole lot of creativity to get by. For example, I found a discarded cute stretch mini skirt just outside of the girl’s locker room at school which fit me, and I had it for years. The rest of my “collection” came from being able to do work around the house, and a rural newspaper route I had delivering papers. My parents loved the fact that I was so industrious without ever knowing the real reason why.

As I continued my ascent towards unwanted puberty and testosterone poisoning, sadly I continued to grow like a weed, making it less probable I could find any clothes to fit me. Somehow, I did by being very creative with my meager funds and having the courage to sneak out of my grandma’s house to secretly go shopping for clothes and makeup. As I always point out, we lived out of town, and the only way I had to get around was by my bike, unless I spent the night at grandma’s. Who lived close to downtown where we lived. I survived the clerks in the stores I went to and slowly became better at what I bought.

Through it all, I thought I would outgrow this portion of my life when all I wanted was to be a girl. Like a weed, it kept on growing in me and refused to go away. I went through the usual phases of gender dysphoria many of us go through. The heights of euphoria when I crossed dressed, and the lows when I was not able to. The pressure on me continued to build up until I took chances and dressed in a locked room with my brother around. Certainly, if I was discovered, my parents would have treated me with enough weed killer at a psychiatrist appointment to do me in. My parents’ eldest son wanting to be a girl would not have been tolerated.

Either I was better in hiding my cross dressing from them, or they chose to ignore it, because nothing was ever said to me, and I dodged any trips to therapy where they knew nothing about gender dysphoria and would refer to me as being mentally ill.

The older I became, the more my weed sprouted and refused to go away. In fact, when the internet era began and we bought our first computer, it gave me the chance to research what sort of a weed I had. Very quickly I learned my early ideas were correct and I was much more than a weekend cross dresser who was more or less wanting to look like a ciswoman as some sort of a hobby. In fact, I was transgender which was a new term back in those days. For the first time in my life, I found a label which fit me. I was not a cross dresser at all, nor was I a fully-fledged transsexual who wanted to run off and have genital realignment surgery. Through the computer I was even able to meet others similar to me for the first time in my life.

At that point, I began to realize my weed was not a weed at all, it was turning out to be more of a late blooming flower which had to be explored and nurtured. As  I began to explore the new feminine world I was in, I discovered how complex ciswomen had it in their lives and what affected them. I can use my second wife as an example of how badly a woman could feel when her husband wants to run off and be a woman. Often without having the knowledge to do it. I felt sorry for my wife, and we fought often, but there was nothing I could do about my new flower in my life. It was not out of control as much as it was me and I refused to confront it. Long story short, she did not live long enough to experience the transfeminine person I had become and that was a shame because like it or not, she had a lot to do with the new feminine me.

Now I feel sorry for all those toxic men and ciswomen who can not seem to find their way out of their weed patch. Growing a beautiful new flower is the only way to go as you live your life as a transgender woman. Now I know why my old male self never liked flowers.

 

 

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.

 

 

 

Tuesday, October 21, 2025

Gender Lost and Found

 

Image from Patrick Hawlick
on UnSplash.  

Navigating the path of lost and found is often very difficult for a transgender woman or transgender man. Speaking for me only, my path was filled with many holes and dead ends before I ever saw any success.

Perhaps, even more frustrating was the fact that once I thought I had made a significant move forward, I would hit a brick wall and be rejected again, and desperation set in. Too many times, at the beginning of my feminine experience when I had no clue of what I was doing wrong when I had enough courage to leave my dark closet. It finally occurred to me that I had had enough of my frustrating existence as a man. Sadly, some days I was on my transfeminine game. Some days not so much as there was so much to learn. Such as, on the days when my makeup, hair and wardrobe looked presentable, I caught myself making the same old male scowl I had perfected to keep the world away. It got so bad, I even had a little girl point me out to her mom by saying “Look at the big MEAN woman” Not the image I wanted to portray but at least I passed the woman part. The gender cup was half full, and I had learned a valuable lesson.

My biggest challenge was putting together my feminine image once I succeeded in getting it out of the mirror. The mirror was always kind to me by telling me just what I wanted to hear. While the public was brutally honest with me and they were my mirror. Sometimes I found what I was looking for and was accepted as a trans woman, and some days I wasn’t. The classic lost and found. My goal always was to keep my gender finds much more frequent than my losses. What I never knew was how difficult that would be. I thought I had a good understanding of what a woman’s life would be all about, until I learned how wrong I was. It seemed my lessons were like peeling back the layers of an onion. Even to the point of shedding tears when I was not successful.

The more I followed the obscure gender signs on my path, the more of my male life I lost and of course, he hated it. With the hate came an alliance with my second wife to stop me from finding more of my transgender self. The two on one battle was never fair, but I knew I would have to fight it anyway for my self-survival. The ultimate lost and found was at stake for me. I had a life to lose when I transitioned as I faced the very real reality of losing my marriage, family, friends and employment. On the other hand, I faced the growing reality I could live out my lifetime dream of living as a woman on my terms.

Ultimately, I discovered I uncovered a life so rich and full, I wondered how I had ever lived without it before. Of course, I am referring to my new life as a transgender woman. I found my unique life between the two main binary genders gave me a perspective on life that many others just don’t have. I never lost my knowledge of what men think, while at the same time gaining an idea of what women were thinking too. In fact, several women I knew after I transitioned reached out to me for ideas about problems they were having with their men. I knew I had finally arrived and had gained more than I had ever lost.

As I could see the distant finish line on my gender path, I picked up speed and did things such as start gender affirming hormones or HRT. The hormones never made me transgender but helped me to sync up my internal gender issues. I was so fortunate when the doctor said I was healthy enough to start his hormonal program. Minimal dosage or not, I was on my way again.

Even though, I don’t think I would wish gender lost and found on anyone, for me, what I went through made life interesting. Just to understand in my own way what ciswomen go through in their lives as close as I could took me closer to my goal of jumping to what I saw as the side of the gender border, I wanted to be on. I even lived through the old “bait and switch” side of life when I thought I was being successful, but I wasn’t. Ultimately, learning more and more transgender lessons as I did.

 

 

 

Friday, October 10, 2025

No Addiction...Just Fact

 

Image from Yumu on
UnSplash.

Perhaps many of you went through the same misgivings about our male to female transitions as I did.

First, I felt it was a simple fetish with the new feminine clothes I was trying to wear. Then, when I outgrew the fetish idea along with mom’s clothes, I needed to try to determine exactly what was going on with me and my gender issues. With no help, and stuck in a very dark closet, I felt alone with no one to talk to. Thank goodness for the “Transvestia” publication by Virginia Prince coming into my life by pure accident which gave me hope for the future. There were others like me who wanted to look like women and have mixers with each other. If only I could make it to one, maybe some of my gender questions could be answered. While entertaining, the mixers I discovered which were close enough for me to attend, did not really answer many of my deep-seated questions. Such as why I was wearing women’s clothes as much as possible. Was I addicted to the clothes or was something else going on.

It did turn out that something much deeper with me was going on. It took me years to figure out the truth. Something much deeper was going on with me and my deeply held gender issues which should not have been problems at all, if I had faced up to them. I was not addicted to looking like a woman, the fact was, I wanted to find my own version of being a woman.

Then the real search for my identity began, as I finally had the courage to open my closet door and go out. In the beginning, ever so briefly until I built up my confidence as a novice transgender woman. Ironically, back then, the term transgender had not been widely used. There were only transvestites (or cross dressers) and transsexuals who wanted to have major surgeries called sex changes. Through this period of my life, I had the uneasy feeling I did not really fit into the transvestite or transsexual mold. I was different and still confused. All the diverse parties I attended were not helping me decide where I really fit.

Still, I kept trying to find my way, and I kept meeting more and more people on the gender spectrum at the parties I went to. From cross dresser admirers to impossibly feminine transsexuals, to the occasional lesbian, I was able to broaden my knowledge of the gender world as I knew it and further research where I belonged. By meeting all of them, I was able to determine where I wanted to be in the world as a transfeminine person and go from there. Plus, I did know, once and for all, the simple act of looking like a woman was not an addiction for me. It was a deep issue which sooner or later in my life I would have to face.

At that time, my progress was slow but steady as I made a far-ranging group of acquaintances in the gender community I was visiting. On one side, I was dealing with Ed, a part-time closeted cross dresser who had a crush on Michelle. A beautiful transsexual woman we both knew. I was stuck in the middle of that strange relationship. Trying my best to be understanding. All I knew was, the interactions I was having were not helping me with my issues which once again I was internalizing. The same thing I perfected in my male life which was so bad for me. I finally came to the point where I realized I needed to be my own person as a transfeminine person. I knew for sure; I had the dream of someday living fulltime as a woman. I just had no idea of how I was going to get there. I set out to discover answers to the many questions I had.

Such as, I knew I was not a cross dresser or transsexual. I was transgender looking for my path. Was I gay? What was my sexuality going to be under the gender affirming hormones I was seriously considering taking. It took me many years of searching before I finally received some long-awaited answers. And would I ever have the courage to face who I really was.

I was fortunate as I always mention that a small group of lesbians took me in and pushed me along my transition path. My sexuality did not have to change and that was one big question out of the way. My validation came from other women, not men and that was a fact.

Once I fully escaped my gender closet, I could look around with confidence and know my new transgender life was not built on addiction that I tried to solve, but on the facts, I refused to accept. I was never meant to be a man, and I was living a lie. The problem was I became good at the lie, and it was difficult to give up. Finally, I did learn through all my searching what the difference was between addiction and lie. Not a fact.

 

 

 

 

Saturday, October 4, 2025

Be Safe rather than Sorry

 

Toxic male from UnSplash

Before I begin this post, I have a disclaimer. I did not follow what I preached many times when I opened my dark gender closet door and ventured out into the public. I broke many unwritten rules I knew were true.

I will say, the times when I came out were much different than today. Not so much kinder and gentler to transgender women and trans men. Mainly, what I am referring to is the person at the top ruining the nation we have, and I don’t have to mention who he is. Basically, he is the top toxic male who empowers all the other toxic males who potentially can give us trouble. There is a real difference in just being laughed at all the way to being physically attacked.

In my case, as I always mention, my initial problem was drawing attention to myself rather than learning how to blend in with other women. I was fortunate I grew out of that phase quickly before I got into trouble other than just being laughed at.

Another of the main issues I encountered was how I was presenting myself once I was fairly confident, I could get by. What I mean was I was going out primarily as a single woman. Which is primarily something ciswomen just don’t do. They believe there is strength in numbers I just did not have. To make up for it, I tried to make sure I did not sit down next to a man if I could help it, and if there just happened to be a vacant seat, I tried to mark it is as mine. What I tried to do was use my cell phone as my major prop. Especially if it was during the warm weather months when I could not throw my jacket over the seat next to me and reserve it. Often, I would act like I was texting a potential friend on the phone who was going to join me. Anything to throw a toxic male off my path.

 I learned quickly when I discovered how much nonverbal communication went on between women that men knew nothing about. One night I had a prime example when a toxic man tried to strike up a conversation with me at one of the places, I was a regular at. When he did, I received a nonverbal warning from one of the bartenders I knew about him, so I rapidly left the venue before anything happened.

All of those methods I used helped me to survive in a new exciting world as I left the gay venues behind me and started to learn what the real world was all about. All very important points if I was ever going to make it to my dream of living as a transgender woman. My learning experiences turned out to be tremendous.

As I said, times have changed today and so much more is at stake for all of us. Whereas a couple years ago, a stranger would be less likely to say anything to you. These days, all of that has changed. There is more pressure on all of us to put our best foot forward as transfeminine people. I always mention the weight I lost when I first came out. Which helped me to buy more stylish clothes and obviously look better. At the same time, I began a very serious skin program which started every day after I shaved. I was doing as much as I could to improve my overall feminine self. All of it gave me confidence to move forward, which I needed badly.

Finally, I would be remiss if I did not mention the loss of your male personal security when you enter a new feminine world. Don’t take chances with your security by doing the things cisgender women already know. To the best of their ability, they try not to park in dark unmarked areas unless they have strength in numbers. As I read, in some areas, women even have to guard their drinks from toxic men trying to drug them. Can you imagine that? Well, you have to when you go through a male to female transition.

This entire post urges you to be on your game when you come out. Among other things, be careful how you carry your purse in crowded areas. It all adds a level of acceptance as a trans woman which goes far past your basic appearance which of course is important too.

In todays’ world, it is important to know your circumstances at all times, not unlike a cisgender woman who learned what to do around toxic males. Look at it this way, you will be a more complete woman ready to earn your place in today’s world.

 

 

Saturday, September 27, 2025

Transgender Dreams

 

Image from Maximus Beaumont
on UnSplash.

Over the years, I experienced slow progress towards achieving my transgender background which I refused to accept.

What I did to exist with my gender dysphoria was to cross dress when I could, all the way to attending Halloween parties completely dressed as a woman every year. When I did, I could judge the reactions of the public to me. Eventually though, the part-time cross-dressing and annual Halloween parties were not enough. Which led me to explore more and more the world as a novice transgender woman. Being a novice, I suffered too many bumps and bruises as my world changed from male to female. Primarily because my male ego was suffering at the abuse he was taking when he tried to give up control to my long hidden feminine self. He thought wearing ultra short mini skirts would be enough to gain acceptance into a female world.

When just the opposite happened, he needed to grudgingly give up more and more control in my life so I could progress and even briefly thrive as a transgender woman. When I started to look around at other women around me and began to blend in with them, I started to be successful in my life.  In fact, I was too successful at times when I started to be accepted in the world. I began to look for more places to go to see if I could progress my life as a transgender woman. Keep in mind, at that time, living a life as a transfeminine person was still a distant dream. Fortunately, I was receiving enough positive feedback to keep moving.

I discovered most of the world did not care about me, even though I felt all eyes were on me as a woman. Women were looking me up and down to see what made me tick while at the same time, for the most part, men were ignoring me because I was not that attractive. I started to progress in my new gender when I began to have confidence in myself knowing the world could get over it when and if I ran into any problems I could survive. At the same time, I was improving my wardrobe and makeup skills, which helped me to improve my life as a transgender woman. All of a sudden, I realized I could achieve my dream of living in a feminine world, but I still had a long way to go.

Progression began to happen much more quickly, even though I had roadblocks on my path in areas such as communication. Naturally I knew women had an entirely different way of communicating than men. Direct communication was out, and passive indirect communications were in. I needed to learn quickly how to look another woman in the eye and try to judge what she was thinking about me.

Through it all, I had a wife and very active male life to deal with. Neither wanted me to succeed in my dream life.  At certain points of time, the noise of life around me was deafening and neither would step up to help me as I was trying to adjust to a new scary existence. I was alone. I thought. But I wasn’t, I had my long hidden feminine self to step up and help me. She took over as if she had never been forced into the background her entire life. She led me to be the person I should have always been.

I was able to progress through the final steps I needed to make to succeed. The combination of women friends, experience and hormones (HRT) provided me with the final push to shove my male self into the closet for good. Even still, the final decision to give all my male clothes away took a lot of thought. Finally, one night, I could take the pressure no longer and needed to make the move to live my dream. When I did, the pressure was off, and I had a new lease on life. Once I lifted the weight I had carried for so long, I was a new person and had progressed towards my dream. I also wondered what took me so long to make the move. Fifty years of cross-dressing and testing the world was far too long and my mental health suffered because of it.

Finally, I made the choices which should have been obvious to me all the time and decided to reach out and grasp my transgender dreams.

 

 

Thursday, September 25, 2025

Restroom Adventures

 

Image from CDC on UnSplash

Since my wife Liz and I went away on a trip to New England for so long, I have several restroom adventures to share.

The main one I did not think of was what would happen when I needed to seek out an open handicapped stall to use because of my mobility issues. I needed all the help I could get to make my way around to get to the toilet.

The first big issue came in Boston, where I was not expecting any difficulties. The first problem came when the only elevator down to the restrooms was broken and I had to try to use a steep set of stairs to make it to the restrooms themselves. I guess I looked unsteady enough for a younger man to offer to help me down the steps. But I made it alone. Then I found the handicapped stall and it was empty. The only bad part was the lock on the door was very flimsy, but by that time, I had no choice but to try it anyhow. In the beginning, all was good, and I finished my business with no problems. Then I heard a mom and young daughter enter the room. At that point, I tried to pull up my leggings and get myself together before BOOM, the kid barged through my stall door before her mom could stop her. Fortunately, I had my leggings almost all the way up as the mom pulled the kid out of there and all was alright. I went ahead and washed my hands and swiftly exited the restroom with a slight smile on my face.

Another one of the positives which happened on the trip was I got a chance to work on my voice again. It turned out I needed a passable voice to get me by in the restroom which on occasion was really crowded. Several times I had to respond to someone inquiring if the stall was occupied. The last thing I wanted to do was respond to another woman asking if the stall was occupied with a man’s voice. I did well enough I guess because no one ever questioned me on it.  Which gave me extra confidence to carry on other conversations with other women on other topics.

No matter how many rest stops the bus made, there still were times when I had to use the toilet on the bus. It was times like these when I was happy, I could sit down to pee. If you ever tried to negotiate moving around on a motor coach, you know what I mean, At the least you have to be very careful and at the worst, you have to be really careful to check the seat before you sit down. Even though I have to give the Amtrak train we took from Boston to Maine passing marks for timeliness and comfort, the restrooms left a lot to be desired and in fact, one seemed to be flooded and out of use. Fortunately, I did not have to go and let another woman take my spot.

Similar to so many other bus trips we have taken, in a relatively short period of time I was accepted for myself and no indication of any pushback of any one on the tour except that one guy on the first day who made the point of pointing me out to his wife From then on, I ignored him and everything was OK. It seems there always needs to be at least on hater these days wherever you go sadly.

Traveling while transgender will always carry extra baggage and we did not even go on modes of transportation such as flying which brings with it a whole other set of potential problems. Once I conquered my rest room fears, I was able to bond with the other women on the trips, and all turned out to be a good move. I made it through mentally and physically, so we have another trip planned. The whole process keeps me challenged and aware of my transfeminine being alive and well. Which is what I need at my age of seventy-five.

The restroom adventures just turned out to be the icing on the cake, it even got to the point when other women were helping me to the restroom. I needed all the cisgender acceptance I could get to build confidence. In fact, I found myself in situations where I was in danger of outing myself. Which is a topic for another blog post. 

Wednesday, September 10, 2025

Change was Coming

 

JJ Hart

As I grew into myself, I learned the truth. Change was coming if I liked it or not.

Change was one of the reasons I loved the fall season so much. As the weather cooled off and football came on, I could go through my feminine wardrobe and see what I could keep and what had to be discarded. Plus, I can’t forget Halloween which of course is the cross dressers’ national holiday in October.

Sadly, as the leaves began to change and fall from the trees, the whole time was bittersweet for me. The worst fall I could remember was when I was on a six-month delay to join the Army and I was working at a small radio station in Bowling Green, Ohio. If you are not familiar with that part of northwest Ohio, it is very flat to the point that any hills are manmade. One night, I was just driving around feeling sorry for myself as I looked ahead to Army basic training and I was so sad as the leaves blew in front of me. If I could have cried, I would have, but tears were nearly impossible for me in my male pre-HRT days. Similar to everything else in those days, I internalized my feelings and tried to move on as deep down I knew change had to happen.

During that time, I almost outed myself to my roommates in the apartment I was staying in until I left for basic. On one trip home, I brought back one of my favorite outfits along with a wig and makeup to Bowling Green. One day when I left, I assumed I had hidden my belongings well enough to not be discovered but I was wrong, and one night when I was preparing to surprise a male visitor to the apartment, after I went to work of shaving my legs and face, I checked for my clothes, and they were gone. I certainly thought, for a while change was coming then it was not. No one said a word to me and very soon, I was off to play soldier anyway so nothing else mattered.

Back in those Vietnam War days, basic training was an intense team building experience when a few drill sergeants needed to try to get a bunch of raw recruits ready for possible combat. During this time, the only way I could keep my girl self-alive was to bury her deeply in my subconscious mind, So, when we were on long forced marches around Ft. Knox, I made sure I thought about the well-being of my girl and the changes we would go through after my military service was finished.

Looking back at the three years I served; the time now seems like a blur and when I was discharged, I came really close to making a big change then by picking my future wife up at the airport cross dressed as my transfeminine self. I even went as far as hinting as such when I wrote her a letter. (Remember those?) Again, my male self-won out and I decided not to, and my big change had to go back to coming again. I did not have the courage yet to face my gender truth and took the easy way out and went back to accepting all the male privileges I had earned.

It was not until I became a parent and had reached my thirties did change to me become a real priority. I will always remember my thirtieth birthday being my hardest because I still hadn’t decided what I was going to do with my life. Sure, I had employment and financial issues to be aware of but again the underlying big elephant in the room was what changes would have to happen with my gender. I knew it was never going to be easy to present well as a woman, and I needed to work extra hard to earn whatever passing grades I could achieve in the public’s eye. Once I made the mental changes to proceed, much of my work became cosmetic in nature.

I was able to move the elephant aside and set about learning what it would take me to really live life as a transgender woman and not just be the “Pretty, pretty princess” my second wife called me. As change set in, I learned very few trans women or women at all live the life of a princess and I had a lot of work to do to put my male life behind me.

The last major change I put myself through was the hormonal one when I started gender affirming hormones. The HRT allowed me to sync up my external and internal selves and live a more productive life as a transfeminine person.

Tuesday, September 9, 2025

Dressing for Success

 

Image from Mohammad Nadir
on Unsplash

During my earliest days when I was forced into being a boy, anytime something negative or even challenging happened to me, I would run home and seek solace in my soft and colorful feminine clothes.

Soon I called the cross dressing I was doing, dressing for success. Mainly because I felt better as I did it. The sad part was, very soon the feelings of gender euphoria went away, and I was back in my unwanted male world where I was expected to succeed. During that time in my life, I was able to barely keep my head above water and still slowly improve my feminine basics in such things as the makeup arts. I guess all those hours of watching my mom apply her “face” as she called it, came back to help me. This was the 1950’s when women took their appearance much more seriously than today. All women were expected to dress for success.

As I barely stayed afloat with my cross-dressing challenges, it soon became more evident to me that there was much more going on with me than met the eye in the mirror as I tried to appreciate myself. It was about that time, when the internet showed up, and I was able to research terms such as gender dysphoria and transgender. Suddenly, I discovered who I might be and certainly found I was not all alone. It all started to make sense why my urge to cross dress never really seemed to go away. It was always with me in the back of my mind.

Soon, as I joined the world as a novice transgender woman, dressing for success largely depended on if I could go out into the world and blend in. I began the easy way by trying my hand with shopping mall clerks who for the most part were only nice to me for the money I needed to spend so I could be more fashionable and feminine. From there, I branched out to challenge myself by stopping to eat lunch and face servers one on one to see how I did. I did well, and very rarely did I have to run home and wonder what I did wrong and go back to my gender drawing board. I did not realize it but what I was doing was replacing my mirror time with time in front of the public. A very valuable learning experience as I discovered venues such as coffee shops, bookstores and even antique malls where I could shop and relax.

Each experience helped me to learn more about myself as a transfeminine person and then dress for success from it. To quit being so flamboyant with my wardrobe and wigs became my new goal as I was settling into my new life. People began to know me quicker, so I needed to be better in my approach to dressing for success. I learned I did not have to lose any of the enjoyment I experienced as a trans woman; I just needed to follow the lead of the cisgender women around me. I did not necessarily have to dress down for the grocery store and up when I mixed with the professional women out for a drink, but it helped me to feel better and relax. Plus, heels and hose would have certainly not worked when my lesbian friends, and I got together.

At times I even took my dressing for success to the extremes to be able to judge what the public was thinking of me. I used to wear my best sunglasses so that strangers could not see my eyes and tell I was looking at them, but were they looking at me? And one of my favorite “props” to use when I went out to be alone was my cell phone which I always had handy when I turned out to be the only woman at the bar. That way, I was trying to show anyone else I had someone else on the way, and I was saving their seat.

To be sure, dressing for success as a transgender woman was always a more complex process than doing it as a man. From undergarments to accessories such as jewelry, wigs and purses, women naturally lead a more layered life which can be reflected in the way they dress. I certainly had many more compliments on my outfits as a woman than I ever did as a man. Primarily, it was because it was something men never do and often, many cisgender women used compliments as simple conversation starters when they were curious about me.

As with all cisgender women, dressing for success is something transgender women must learn. The problem being we come from such a vastly different background to do it. Almost none of trans women had the benefit of peer pressure and a mom to guide us through the initial makeup process. Our workbooks were blank when we started our gender journeys. Playing catchup was not a fun game to play for me as I found making up my face was different than painting model cars. Most certainly, dressing for success was a lifelong experience for me.

 

 

Thursday, September 4, 2025

Why Would I do this to Myself?

 

JJ Hart, Club Diversity
Columbus, Ohio.

Even though it has been years since I have been asked the question which asks why I am transgender, I withheld all my sarcastic comments such as I found my gender dysphoria in the bottom of a cereal box and thought of a concise truthful answer.

The truth is I had always known but was afraid to accept it. In the meantime, I set out on a slow, often torturous process to reach my impossible dream. To all the naysayers I interacted with, I just wanted to say, if I was not serious about switching male to female lives, why would I do this to myself. I knew early on I brought a lot of the problems with the public I faced on myself because of my novice attempts at presenting myself to blend into society with other women. I was coming off like a clown in drag, rather than someone who was seriously trying to jump the gender border from male to female. I was not playing around.

As my old male ego suffered, my feminine ego persisted and finally I did better in the world. I think too, the world took me seriously for the first time and did not have to ask the “why” question. I discovered too, that most of the world was just doing their thing and could care less about me if I could just blend. As I did blend in and began to carve out a new life for myself, the “why” of what I was doing became more personal and pressure packed. I was risking a successful male life I had worked hard to achieve, in order to live a new life which was so scary and at the same time felt so natural. I was having fewer people ask me why I was doing this transgender trip to myself.

Which brings up the question why any of us would transition ourselves if we were not desperate to do it. As an example, my own personal example was all the self-destructive behavior I put myself through including suicide and alcohol abuse. I was a living example of why I would do all of this to myself to be a transfeminine person. I was serious about what I was doing and needed to continue up the gender path I was on.

What helped me too was when I began to see the same people more than once. Since I was easy to remember, strangers began to put a name to my face, and I began to become a regular in several of the straight venues I went to. I just followed my tried-and-true idea of if I was friendly, did not cause any trouble and tipped well, I would be welcomed repeatedly.

The farther I went along my gender path, I began to wonder what sort of a transphobic gender bigot or female TERF would even question why a transgender person does what they do. Such as making all the sacrifices we must make to live the life we desire such as risk losing family, spouses and employment. Slicing off a major part of our life and starting over is intimidating enough without the naysayers questioning it.

On the other hand, there were things I wanted to do to help my feminine transition along such as losing nearly fifty pounds and beginning to take better care of my skin. Suddenly, I had access to more fashionable clothes which fit better, and my makeup was easier to apply. All because I took the time to take care of my transfeminine self. When I did so, even the haters I still encountered needed to get over it because I was more secure in myself. Even though I was increasingly successful in the world as a transgender woman, humans are like sharks, and every now and then I needed to fend off any unwelcome attention I might have attracted.

Possibly, the most important answer to the “why” question came when I decided to seek a doctor’s help and begin gender affirming hormones. Naturally, the decision on HRT was a major one and not a decision to be taken lightly. At the time I started hormones, I was leading a healthy male life which would have to change. I knew all along, I had come too far on my gender path to turn back now and quickly learned I had made the right decision to start HRT. My life blossomed as never before, and I never missed my old male body and emotions again.

By this time, I had married Liz and settled into a transgender dream world I never thought I could achieve. I guess I was to the point of if I could dream it and could do it. Which is a topic for another blog post altogether.  Plus, I had answered the question once and for all of why I wanted to do this to myself. It was fulfilling my own personal destiny.

 

Sunday, August 31, 2025

Long Labor Day Weekend

 

Image from Anna Storsul
on UnSplash

Labor Day weekend is upon us in the United States which gives us an opportunity to take an extra day off and think about what got us here and how close we are coming to losing it.

Even though I have never been in a union myself, I am an amateur historian and know what unions did to transform this country. All you need to do is some basic research on how bad working conditions were in the steel industry as well as coal mining and elsewhere to see what unions brought about. So, on Labor Day, I salute them.

Elsewhere, the weekend this year features some beautiful weather with sunny blue skies and very low humidity for a change around here in the Ohio River Valley (Cincinnati.) Of course, the early fall like conditions won’t last forever and soon we will be back into summer’s last call. In a couple of weeks, my wife Liz and I will be headed for the East Coast, Boston, Maine and more so I am hoping for the reasonably good weather to hang around until then.

By now, you may be asking what does any of this have to do with being transgender? The answer is it has everything to do with being myself as a transfeminine person. Since this marks our fifth bus tour over the years of hanging out with other cisgender women waiting for my chance to use the bathroom, I still have lingering paranoia with using women’s rooms which goes back to my earliest days of cross dressing in public. Even though I have not had any problems in the past with anyone else, I still have the idea it only takes one bigot on the bus to ruin my trip. At least, this time we are traveling through more liberal blue states, so I won’t have that to worry about. As I said, my lingering fear is subsiding, so I can concentrate on having a good time and seeing the sights of New England. The last trip we were on a woman asked if Liz and I were sisters, so you cannot get more validation than that.

Closer to home before we leave, tonight we are going to dinner at our favorite restaurant with her son. It is another venue I have rarely ever been misgendered in and have never had any serious problems. It always feels good to just exist and enjoy myself since I worked so long and hard to get here as a transgender woman. The more I can fly under the gender radar in today’s world, the better I feel.

Before we go, I will have to shave closely, apply moisturizer, powder and lipstick before I change out of my The Ohio State sweatshirt and into a frilly feminine top and brush out my hair. All of which are still fun for me to do. Not just something I have to do to present better in the world.

Finishing out the day, it will be time to head home and watch the end of summer Cincinnati fireworks display. The display is always huge and attracts nearly a million people on both sides of the Ohio River. Back in the day, when I was younger and another person, I used to come down every year for the Booms. But age and mobility have caught up to me, taken their toll, and we just watch them on television now. Then let the out-of-control neighborhood idiots set their fireworks off and scare the animals and any near veterans with combat PTSD. Out of the two cats Liz and I have; one hates any sort of loud noise.

As with many other holidays, Labor Day presents yet another milestone in my transgender life. I can remember quite vividly when I used alcohol on holidays to dull the pain of not having the chance to spend them as my feminine self. I was fortunate to have escaped my closet and the control alcohol had on me before it was too late. It turned out it was all in front of me all along if and when I had the courage to reach out and seize my opportunity to transition and just be me.

I guess you could say, I needed to labor to do it, but it was worth the effort. When we toast ourselves tonight with our Margaritas, I will propose a toast to all the work we three have put into to where we are today. And, to all of you, no matter where you are today, have a chance to pause and celebrate the gender journey you are on, or have yet to do. Buckle up! It is one hell of a ride. 

Saturday, August 30, 2025

Out od Sight...Out of Mind?

 

My wife Liz on left and daughter on right.

Most if not all transgender women and trans men go through phases in their life when they think gender issues are out of sight and out of mind. It is not entirely different than the moves some state legislatures (Ohio) are going through to try to erase us in the public’s eye.

If you read my posts at all, you know how I feel about that. Trans people have always been around and always will be. Attempts to erase us will be futile. On a lesser but just as important level, we try to erase ourselves by purging our lives too. I know the guilt of being a cross dresser or transgender woman became too much for me to handle and I threw out most of my treasured feminine wardrobe and makeup. Out of sight, out of mind I thought.

In the long term and the short term, none of my purges worked because I refused to accept my true self. I had my life all backwards and I was not a man who cross dressed as a woman, but a woman who cross dressed as a man. Until I figured it out, I kept trying to hide the obvious. Of course, it did not help as I started with two gender strikes against me. I went through birth as a male and then had to go through male puberty and suffer from what I called testosterone poisoning. My body kept the bullies away and allowed me to play sports but caused me torment when I was in front of the mirror trying to be a pretty girl.

As life went on, I thought for the most part I had learned to live with my gender dysphoria the best I could. To this day, though, I wished I could be a “normal” male. How much better could my life be if I could socialize with the other males around me without feeling as if I was an outsider. I grew tired of being an actor inside my own skin. The only thing I could do was mentally try to get rid of my feminine self. Taking me full circle back to why I was keeping all those clothes, wigs and makeup anyway. It took me by throwing them away to understand exactly what the problem was. It was not a problem unless I it made one, which I was by purging again.

Deep down I knew I was wrong and very shortly I would be re-stocking my fashion and make up to try my best to present feminine again to myself and the world. However, I was very stubborn and my male self-hung on way too long refusing to give up on his hard-earned male privileges. Life could have been much easier by staying where I was in the gender world, but it was just wrong, and I couldn’t. The more I lived as a transgender woman, the more natural I felt, and I never wanted to go back into the male world I had made the best out of.

Increasingly, the male purge was looking to be the one I was going to attempt to make. I was sick of living a gender lie, and I wanted to reverse my idea of living. I wanted to feel “normal” again but this time around a group of cisgender women. Flipping the gender script on my life was the most difficult thing I had ever attempted to do, but somehow, I made it through the female gatekeepers and did it.

In my new transfeminine life, I was rarely out of sight and out of mind. I had a lot of help to do it who I will never forget. I had spent my whole life chasing a dream and had finally achieved it. As I symbolically and literally gave my male clothes to charity, I stopped to remember the entirety of what I was doing. I was giving up the male side who had dominated me for so long. To be sure, he had served me well, but it was time to go, and this final purge was a triumphant one for my transgender woman who had waited so long to live. After all, she had her life taken away several times when she was purged nearly out of existence.

She survived and so did I and everything in her power to make things better. When I worried how I would be perceived in a new world. She had my back when it mattered, and it did. Even in the days when she had to give me quite a bit of tough love. She had to watch me grow through my ill-advised teen cross-dressing years into a presentation I could be proud of or at least satisfied with.

Out of sight, out of mind never worked for me.

 

 


Thursday, August 28, 2025

Gender Immigration

 

L'eggs said it best.


With all the negative publicity being brought to the new immigrants to this country by the orange felon/pedo in Washington, I thought it might be time to connect the dots to my own immigration. A gender one.

My immigration plans began as a vacation. I was tired of the male world I was competing in and taking a break as a cross-dressed girl in makeup was a great way to escape my life. Little did I know, from these humble beginnings, I was starting a lifelong journey which in many ways, I am still on over a half a century later. Had I known, I would have ever attempted to undertake such a radical immigration.

Early on, I was just looking to grab the so-called low hanging fruit of cross dressing. I enjoyed the feel of the clothes, all the way to the thrill of hose on my freshly shaven legs. Then, I slowly began to realize so much else was happening. Increasingly I wanted to be more and more like a girl and started to wonder about pushing my male self out. It was difficult because I came from a highly male dominated family. As I pushed forward, my immigration into the feminine side of life became more intense. I tried my best to acquire new more fashionable clothes and even bought my own makeup and panty hose. Do you remember the “L'eggs” panty hose which came in plastic egg shaped containers which it seemed you could buy everywhere, and is still made today. I learned the hard way; how easy it was to destroy a pair when I unfortunately ran one of the legs. Ruining my outfit.

Progression was slowed by a late-teen collision with serving time in the military due to the Vietnam war. Obviously, I could not bring any of my “stash” of women’s clothes or makeup with me, so I was stuck. No more gender immigration for at least three years of my young life. There were several major positive things which happened for me while I was stuck being a man in the Army. A prime example was all the traveling I was able to do around the world in places such as Thailand and Europe (Germany). The whole process enabled me to keep my mind off my gender issues and set me up with the idea I could outrun my problems. Which, of course, turned out to be impossible. Which should be the topic for another blog post.

After the Army, my life changed again as I entered the world of parenthood. Being a parent of a daughter was an unexpected but pleasant surprise, and my gender immigration was put on hold briefly again. I say briefly, because I discovered my transgender issues ran deeper than I had thought. My presentation as a novice transfeminine person was coming along. My first wife did not care, and I was able to explore my potential future as a gender immigrant at events such as Halloween parties. Each party to me represented a chance to see how I was being accepted as a woman in society.

After a few years, I ended up divorcing my first wife and marrying my second. She also knew about and accepted my cross dressing from the beginning of our relationship but never accepted me being transgender as I immigrated towards being a woman. My male side was like being the Titanic, slowly sinking and then picking up speed with her fighting me all the way. It turned out, the issues I was facing were like the tip of the iceberg. With most of it being hidden from everyone. Including me. She tragically passed away before the final resolution in our relationship was ever decided.

When she moved on to the other side of existence, it was left up to me to decide the future of my immigration. I had certainly paid my dues by taking on all the menial and not so menial work of being a woman. I was on gender affirming hormones and was living as much as I was able as a transgender woman, so I was close to filling out my immigration papers and was ready to go into a world I had only dreamed of. My presentation had improved to the point where I was not the most attractive woman in the room, but I could handle myself to the point where most of the world just did not notice me. So, my immigration was more successful than I ever thought possible.

Perhaps the best part of immigrating was learning to accept and love myself for who I really was. Which meant all the hassles I had over the years as I tested out the world, made my immigration worth it.

 

 

Saturday, August 23, 2025

Closing the Circle

 

JJ Hart at Club Diversity, Columbus, Ohio.


Very quickly when I opened my gender closet door and looked out, I noticed a whole different world I would have to conquer if I was to survive.

To begin with, I was slightly overconfident with my ideas because I had spent so much time studying the girls around me. I was jealous of their pretty clothes and how the boys chased them. I so badly wanted to run in their circle but as we all know, that was not going to be possible for years to come. To begin with, there were so many smaller circles to negotiate before I could advance. So many, I could barely keep track of them all. I had a LONG way to go.

To put it all into perspective, if you remember the Hula Hoop craze, with the round hoop you put on your hips, arms or even neck and spun it around. I was so uncoordinated, I had a difficult time playing with one as I grew up. If I could not even spin a simple hoop around my hips, how was I ever going to accomplish anything vastly different such as changing my gender identity. For the most part, I was naïve and did not understand all the complexities I was facing. While I was obsessed for years looking like a woman, I should have been obsessed with knowing what a woman was really all about. I remained too new to the gender game to be allowed to enter woman only spaces, or what I refer to as the girl’s sandbox.

Then in the middle years of my life when I began to explore the world more and more as a transgender woman, it seemed I had too many hoops or circles in the air. So many, in fact I kept making wrong choices such as the wigs I wore and how I misconstrued how I needed to look to blend in with the public. Instead of dealing from transfeminine strength, I was dealing with my old male ego hanging on and causing problems. I was stuck in my so-called teen cross-dressing years until I rapidly outgrew them in my thirties. Better choices of fashion and makeup helped me to overcome my testosterone body flaws and blend in with the other women who may have had traces of my problems with their body too. Even with all my newfound success, I was still having a difficult time closing my circles. My major problem was I did not completely realize how difficult it would be to stop a life and start over from a completely different point.

As I chased my Mini skirted tail, I had plenty of time to consider what I was doing with my life. In fact, too much as every spare moment I had, I was daydreaming of the next time I would spend as a transgender woman and what I would wear. I am surprised now I had kept my mind on my job enough to be promoted to an upper management position. I would love to have a portion of the time back I wasted. Perhaps, the sky would have been the limit for my male life, but it was not to be because I could not stop until my gender circle was closed.

It finally took a close circle of cisgender women around me to help me through my crisis. My current wife Liz in particular who told me she had never seen any masculine in me at all when I was still living part time as a man. It was the final shove I needed to reach out and close my transgender circle for good.

I don’t think I gained any physical coordination from transitioning, but I am sure I gained mental help when I long neglected woman side took over. I found part of feminine privilege came when I was allowed to participate in a softer side of life which did not revolve pushing and blustering my way through. My new circle involved more mental gymnastics with other women to see where they were coming from, as well as dealing with a passive aggressive side of life.

Not going in circles anymore was a wonderful experience. All my trial-and-error times in the world as a novice transgender woman came back to help me when I made the final transition to where I always wanted to be. No more spinning hoops to deal with which were destroying my mental health. To be sure, all of my bi-polar depression issues did not go away but the overlaying gender issues did. It sounds easy for me now, but all I needed to do all along was listen to my true self and close my gender circle.

 

 

Friday, August 22, 2025

In Over my Head

Image from Alexander Mass
on UnSplash
In the beginning, it was all so simple. Pick something, I could squeeze into from my mom’s closet, try my best to wear her makeup and go from there. Very quickly though I found I was getting in over my head as I began to sink into my own personal gender quicksand.

My first problem was hiding my small but growing collection of feminine fashion. In addition to my parents, I had a slightly younger brother I needed to deal with. Somehow, I managed to keep the darkest and potentially most destructive secret I had away from him, I wanted to be a girl in the worst way. I had no way of knowing then how many times I would be in over my head as I chased my dream. Primarily because I had no way of knowing looking like a woman was just the first step of a lifetime of gender learning. As I like to say, my gender notebook was blank when I received my copy, and I needed to catch up the best I could.

I began by studying the women around me who were my age the best I could. It was all I could do at that time to keep myself from setting myself up for failure when I finally was able to escape my dark, lonely gender closet and explore the world for the first time. When I did, I was naïve and confident I would have no problems. After I was sent home crying after being laughed at, rudely I knew I was in over my head with a lot of work to do. For some reason, for the first time in my life I knew I could not give up and I refused to quit. I kept going back to the drawing board until my makeup art improved and I began to learn the benefits of dressing my self properly as a woman of my age and build. Suddenly, I began to pull myself out of my quicksand and began to move forward again towards my dream of living as a transgender woman.

Ironically, as I moved forward, I ran into many other obstacles in my way. Was I pushing myself into a world which was ready for me or not was one of the main questions I had. The more involved I became in the world as a trans woman, the more I needed to be accepted into women only spaces. The only way I would ever know was if I could conquer my fears and try. As I pressed on, somedays I was more successful than others, but overall, I found I was accepted by other women. The times I found myself in over my head as a novice transfeminine person were primarily when I was approached improperly by men. There were times I needed to run home and rework my gender notebook after close ugly calls with men. I learned quickly, those close calls did not validate my worth as a woman. They did provide me with an insight of what women go through in their lives and I learned fast.

As I was adjusting to the new life I was destined to live, It seemed as if the lessons I was receiving kept coming faster and faster. I learned from my lesbian friends how to validate myself as a woman and from men, what not to do. At no point in time was any of my life easy at this point, but it was scary and exciting at the same time. My dream became so close I could reach out and touch it. If I kept out of the quicksand and kept my head above water, I could make it. The hardest part was still yet to come as I was coming increasingly closer by the day to separating from the male life I resented for so long.

The final decision to change was brought on by my choice to seek out gender affirming hormones or HRT. As I urge everyone to do, I sought out medical approval before I went down the radical path I was on. I was approved, put on an initial minimal dosage and before I knew it, changes were happening which made me a highly androgynous person. One look in the mirror told me that I had made the right decision and I wanted to move past the minimal dosage of HRT I was on.

I can’t say I haven’t found my way in over my head in recent times because of the type of person I am. Did being transgender aid in it? Who knows. We all have our choices to make, and they are all tempered by the people around us. Some are fortunate and have discovered feminine gatekeepers such as spouses were there all along. While others are destined to go it alone. Whatever the case, try to not get in over your head and do the best you can.                                 

  


Growing Like a Weed

  Image from Marya Volk  on UnSplash. I was devastated when I outgrew all my mom’s clothes and I had no sister’s closets to raid for clothes...