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

Sunday, March 29, 2026

The Winds of Gender Change

 

Image from Taylor Flowe
on UnSplash. 


Per normal, we have had a very windy spring here in southwestern Ohio USA. For some reason, I have never associated spring with my gender changes like I have during the fall season. I remember vividly the fall evenings I spent driving around feeling melancholy about the fact that I was stuck in my old unwanted male life. Seemingly, forever. Maybe it was because of the trees losing their leaves which set the fall off from the spring. I just knew it was happening.

Fall was especially bad when I was on a six-month delay to go to the Army basic training at FT. Knox, Kentucky. It marked the time for me that I knew I would have three years away from my gender cross-dressing activities which kept me sane at the time. I was afraid of going to basic infantry training as well as losing my ties to my feminine self for the next three years. The only reality to me was that I had no choice but let the winds of change take me away to a new uncertain future.

When I was in the service, my theme song began to be “Call Me the Breeze” by Lynard Skynyrd because of all the moving I was doing from the US to Thailand, to Germany, I was truly able to feel the wind thanks to the efforts of Uncle Sam and his military. I did it so well that I was even offered a promotion if I stayed in an extra year, which I turned down. Instead, I got out and resumed my civilian life at a small radio station I worked at before the winds of gender change got the best of me, and I started to follow my instincts and began to explore the world as a transgender woman. Which was becoming increasingly evident to me was where I fit in in the gender spectrum.

In the beginning, all I had was Halloween parties to express my femininity and even there, I was not doing a good job of doing it. I was stuck trying to do a trashy look when in fact, my inner woman was pushing for a more realistic approach such as being a professional ciswoman. What did happen was, I got the basics of what it would take if I ever threw caution to the wind and went across the gender border from male to female. It was at those parties that I found that all of a sudden, the other women wanted to talk to me while the men left me alone which would be a theme for my life as I transitioned.

Once I left all the Halloween parties behind me, I started to attend small diverse LGBTQ mixers in nearby Columbus, Ohio. When I did, it was as if there was one of those huge Hollywood movie fans at my back pushing me forward. From lesbians to transsexuals, all were there so I could judge where I would be if I moved forward in the world. Due to the fact that I was still solidly married and had a very good job, I needed to shut the fan off, or at least put it on a slow speed so I could catch my breath and figure it all out because of the gender complexity it all presented. Did I want to give up my life of male privilege to be a trans woman, at that point in time I was undecided.

It turned out, indecision was my worst enemy as I entered the world to explore it as a transfeminine person. Most of my ventures were ill-advised attempts to be accepted in gay venues in Dayton, Ohio where I was barely welcomed and when I was, it was because they thought I was another drag queen. Which was far from the truth. It was not until the winds of change blew me through the doors of the same sports venues I enjoyed as a man did my world began to turn around for the best. To my amazement, I earned my acceptance in those places easier than the gay bars I was going to, or the lesbian bars which were closing due to lack of business. Before I knew it, I was treated like a regular. Even with the restroom privileges I needed so badly.

I was flying high until the winds of change dictated a change and I crashed to earth when everyone dear to me began to pass away in a two year period. Including my wife of twenty-five years. I was in shock and so lonely I drank too much and took unnecessary chances with my life as the winds of change continued to blow strongly. Every time I thought the winds were receding, they would pick up again threatening to blow me off my high heeled shoes.

I was fortunate when I saw the name of a doctor who would check me out and then prescribe HRT or gender affirming hormones and I took immediate advantage to do something I had wanted to do for a very long time. Sync up my inner person with an exterior which was feminized. Even with the minimum dosage I had to begin with, I could feel and immediate change in several areas such as with my emotions and breast growth. When I began to see myself as a different femininized person in the morning mirror, I was becoming more and more excited over the winds of change which were pushing me ahead into a new exciting world.  

The only part of my being who was not surprised by all the changes was my feminine self who had been hidden away all those years with no way to express herself as when she was in the Army. If patience is a virtue; she had it all as my male self-put on a tremendous fight to maintain what he had earned as far as privileges went. Fortunately, the winds were blowing in the right direction, and she won the ultimate battle for my life. I discovered that without her, I would not have had a life worth living.

 

 

Saturday, March 28, 2026

Wishing and Hoping never Made it For Me.

 

Image from Abbot
on UnSplash.



Sadly, just wishing and hoping that we can make it to our feminine dreams just won’t get us there.

Since most of us started our gender journeys with very little natural external characteristics of the gender we want to become, it makes our struggle even more difficult. Even more so when you consider how far trans women like me had to go to hide my true self so I would not be bullied by the men around me. I played sports such as football and worked on cars to hide the fact I did not really want to follow a male path.

In the deep, dark recesses of my closet I spent my time wishing and hoping time would come along to magically change me. We all know how that worked. It did not and I grew more frustrated as I spent my meager leisure time wistfully cross-dressing in front of the mirror at home in the long hallway we had. After the initial success I felt from looking at my imagined self as a pretty girl, I knew it was just not enough. Looking back, I was going through the early stages of being transgender without having any of the terminology to go with it. In the meantime, I needed to keep my public charade alive of making the world think I was male.

Then, along came the shock of puberty with all its unwanted physical changes such as size of body and bone structure. I was helpless as all the changes took place and I was depressed that I was moving farther away from the feminine person I always wanted to be. All I could do was wish and dream for change which never worked. I finally had to do something about it, the pressure on me was intense. The little trips to the mailbox when I was dressed as a girl just were not enough anymore, I could no longer just exist on that little interaction with the world as I introduced my true self.

Early on, once I grew older and found a place of my own, I did venture out into shopping malls and often the experience was brutal. No matter how good the mirror at home was telling me I looked, the public quickly told me something else. Too many times I had to come home early crying because of being laughed at by groups of teenagers I attempted to dodge but couldn't. Fortunately, something deep down inside me kept telling me to keep trying to get better with my make-up and fashion and maybe then I could present well enough to get by in front of the mirror and the public both. The brief moments of gender euphoria I experienced were the indication I needed to know there was indeed more and I was on the right path after all.

Once I did discover I was on the right path, then I needed to stay on it and try to navigate all the blind curves, potholes, and stop signs I encountered. Initially, I was naïve and was not prepared for everything I was about to face. I thought I had a fairly good idea of what was behind the gender curtain with the ciswomen I would have to coexist with, but I did not. All of what I was seeing was the pretty clothes and passive aggressive nature without seeing all of what went into it later as I actually made my way into the world. I really misjudged how complex and layered a woman’s life could be if I decided to follow along.

At first, I thought I needed some woman to show me the way but again was so wrong when I tried. By the time I did, I actually had a better knowledge of makeup than she did, so basically, the whole experience was wasted, and I knew I would have to go up my path on my own if I was going to be successful as a transgender woman. Then, I had to figure out what being a trans woman meant to me. As in my earliest days in front of the cross-dressing mirror, I knew I wanted so much more, and I knew it would involve my evolution into a unique woman of my own. As with any other human born female, I knew they needed to be socialized into being a woman and so did I. It just was because my path to womanhood came from a different way than most women but that should not exclude me. Once I felt secure with feeling this way, I freed myself to more completely live my truth in the world with people who accepted me

Surprisingly, I had fewer problems than I anticipated when my trans friend Raquel told me I passed out of sheer will power, that became the story of my life. I was not trying to “fool” anyone into thinking I was the most attractive woman in the room. I was simply announcing my truth to the world, and they could take it or leave it. No more wishing and hoping for me, if someone did not like or approve of me, that was their problem not mine as I paid my dues to be where I was.

As I look back at all the wishes and dreams I had when I hoped to somehow live my dream as a transfeminine person, I know I wasted a lot of my time which I could never get back. Once I did get my late start and began to make up for lost time, I did begin to learn what I needed to survive in the girls’ sandbox once I was allowed in it to play. Once I did, I resolved to never look back and enjoy what I helped to create. A woman with an unique background allowing her to arrive at where she wanted to be.

Before I wrap this post up, I would like to thank Sara E for writing in and commenting. She is in a similar position as most of us went through. A married man, working through her feminine side.

Thanks to all of you who take the time to read my writings and comment!

 

 

Thursday, March 26, 2026

Trans Girl on the High Gender Board

 

Image from Navy Medicine
on UnSplash.


I remember completely when I was a kid, intensely afraid of heights, and my mom made me jump off the high diving board at the swimming pool we were at. It was the last thing I wanted to do, and I still don’t know till this day how she convinced me to do it. But she did. I am sure she thought that once I did it, I could do it again, which I never did.

Perhaps, by this time, you are thinking what does this have to do with being transgender but of course I can connect the lines as always. Fast forward to the days when I was first gathering all the courage, I could muster to leave the house and attempt to explore the world as a woman. To do it, I needed to jump off that high diving board again and again. Plus, I would have to raise the diving board even higher every time I tried it.

As I did, I discovered little pockets of cross-dressing acceptance I could exist in. Such as the women’s clothing stores where almost everyone was nice to me. It took me awhile to realize the clerks who waited on me were not being nice just because I was another woman, they were being nice because I had money to spend. To them, my gender was not trans, it was green. Even though I took acceptance and built on it to other potentially mellow venues in malls such as bookstores and coffee shops. I was successful in them and was able to build my confidence from there and move up to a higher diving board and jump off. No matter how scared I was, I needed to force myself to climb and jump.

The next comfort zone I forced my way out of was by forcing myself to stop for lunch to see if I would be accepted. For the most part I was, because again, my money was green and I smiled and tipped well. The magic ingredients it turned out to be accepted into a challenging new feminine world. Or so I thought until I kept on climbing. It turned out the climbing part was the easiest. Once I arrived where I thought I wanted to be. I added “thought” in because once I made it to a higher board, the jumping part really scared me. Mainly because I was leaving so much behind me, along with all the male privileges I had worked so hard to gain. Such as fighting back when someone made fun of me for the way I looked. When it happened, the only recourse I had was to go back to my cross-dressing drawing board and try to determine what I was doing wrong.

Before long, my drawing board became quite littered with fashion mistakes I had made. Going through my cross-dressing adolescence was quite painful because I was a thirty-year-old male trying to do it before I learned otherwise. I was exhausting myself climbing up the high dive and then down when I discovered there was no water in the pool. Finally, I learned the hard way to cross-dress to blend with the other ciswomen around me because they ran the pool I wanted admission to.

It turned out that the pool was much farther down than I thought it was, and I had too much time to think about what I was trying to do before I hit the water. I had not made the time to build up the feminine muscle memory I would need to allow me admission to the world as a transgender woman. It did me no good at all if I vaguely looked like a woman if I could not move or communicate like a transfeminine person.

At that point, jumping off the high board became very real to me. I was rapidly coming to the point of decision about what I would do with my life. By this time, I was in my fifties and was beginning to carve out a respectable life as a trans woman. My new world knew what I was and did not care. About my present, or more importantly, my past as a man. I was able to bring what baggage I wanted from my male life without any interference. It made all the difference in the world to me when I needed support from wherever I could get it in the worst way.

As I lost my fear of the high dive, I began to consider other transgender alternatives such as taking advantage of therapy and HRT through the Veteran’s Administration health care system which I was already a part of. I wondered then what my mom would have thought (she had long since passed away), about teaching me to take the long and difficult path to the high board would come back to help me so much later in life. Especially when she was the one who was dead set about me coming out to her after the Army when I tried. Karma came back to help me when I needed it the most. I could jump off the highest diving board I could just to prove I could.

Of course, the final high board I jumped off was the one which saw me do away with all my male clothes and live life as a fulltime transgender woman. In reality, I was never a stylish swimmer or diver, but at least I made it to the point where I could make it in a woman’s world. A world which would prove to be much more complex and difficult for me to succeed in than I ever thought possible. Probably, because, for the most part (except for a few friends) I was filling out my gender workbook as I went along. Preparing myself for when I could achieve the ultimate goal, my lifetime dreams of living as a woman to the best of my ability.

At the least, I was happy I gathered enough courage to go ever higher on my gender diving board and more importantly jump.

 

 

 

Saturday, March 21, 2026

In the Circle

 

In celebration of Ostara.

Today will be a beautiful day to get together with spiritual friends and celebrate “Ostara” which is the Pagan/Wiccan celebration of the Spring Equinox. The circle part comes in when the group is called together to start the ritual. It is supposed to be dry and near seventy-one degrees (F) today in the park we go to for the ritual, so you could not ask for a better day.

Meeting the group carries a deep meaning for me which goes past the ritual. Joining my wife Liz as she went first to the rituals and being accepted was just one aspect.  It was like I was adding a whole new barrier between my new feminine self and my old male one. I felt as if I was climbing a set of stairs to just becoming a complete me because in addition to attending the rituals, Liz and I were also going to Cincinnati area meetups for writers and craft people. I was meeting strangers for the first time when I was just me then surviving. I was proud as well as being happy about it. 

It was like I transitioned for the third time in my life as I went in a big circle. I started out as a cross dresser, moved to a transgender woman and then back to me. I cannot say enough about the confidence I was able to build up as I traveled my path from one stopping point to another.

In addition, I was curious about how going to the rituals would affect how I viewed the world spiritually. I knew I had always been a somewhat spiritual person without being a part of any specific religion. If I was made to have a choice, I would always say I was Buddhist because of my days in Thailand and how much I respected the gentle ways of the people. Anything but Christianity which rejected the very basis of being transgender in not all but several cases I had encountered. One way or another, religion is not a subject I want to get into here. It is a point of no return and easy to get stuck in stereotyping religions if I attempt to explain myself. So, I will leave it at that.

As I said, I am really looking forward to seeing old friends at the ritual again except for one who asks me what the transgender community thinks about what is going on today. Finally, I quieted him down by asking what he thought about what was happening to us. Fortunately for both of us, he said he hated it. If he did not the circle may have been broken.

 

 

 

Friday, March 20, 2026

All Along, I was just Becoming Me

 

Image from Pea on UnSplash. 

As I always point out, becoming me was a very difficult concept to adjust to.

First of all, I needed to understand who the true me really was and work my way to the light out of my dark closet. Sadly, it took me decades to face the truth about who I really was. I was never the male I was seemingly born to be. I was born to be a feminine person, no matter what it took to get there. Which turned out to be the key term over the years, as I risked everything to discover who I truly was. As my male self was busy building a wall to his world by becoming successful in his job, my novice transgender self-needed to take a back seat and watch the clown show.

The problem was that often the clowns were not funny and just needed to stop before they caused complete damage to my life as I knew it. I was living the male dream in many ways with a good job, small family and a close knit group of friends and it was difficult to even thinking about giving it all up, but I did. Male privilege was very real to me and preparing to give it up was intimidating to say the least. Somehow, I needed to find the true me and quit being so self-destructive when my gender dysphoria hit me. In most cases, my morning mirror was to blame when I looked in it for the first time everyday and saw a woman lurking behind my male self-shaving.

I did not really begin to understand who I truly was, until I put my cross-dressing world behind me and started to explore the world as a transgender woman. Before I did though, I needed to draw an invisible line in the sand when I went out and see if I could cross it. When I did, I felt a deep sense of gender euphoria and wellness. When I did not I had to force myself to go back home, return to my cross-dresser drawing board and try again. Which I needed to do many times before I started to get it right. The important part is that no matter how down I felt on the days I was abused in public, there always seemed to be the slightest spark of hope which came from feeling good and natural as my feminine self. Suddenly, finding my true self did not seem to be so far away, if I could find the time out of my busy life to do it.

That is when I started to use every moment of my spare time in my transfeminine explorations of a terrifying yet exciting new world of cis women. Plus, if I was not exploring, I was busy thinking about it when I was working as a man. I wish I had back all the excess time I wasted in those days when I could have put the energy into my family, spouse or work. It would have made such a difference in my life. As it was, my life consisted of slowly sliding down a gender cliff. Not knowing what awaited me when I finally let go of my male self and headed towards a feminine world for once and for all. At that time, I did not realize I would have a team of gentle womanly hands to soften my fall. I still had a lot to learn about going behind the gender curtain.

Even though I was becoming accomplished as my authentic me, I found I still had many years ahead of me to continue my journey. I still had to round myself out as a new person very much from scratch. It was difficult to not automatically out my male self when I was talking to a new woman who turned out did not care about him anyhow. It was time to put him in the background and pick and choose the highlights of what benefitted me as a trans woman creating a new life. It was a different way to live and took a lot of getting adjusted to. Far beyond just worrying about my appearance and if I could use the right rest room. I needed to be on my toes all the time because just the wrong response about my past could give my whole male life away.

Once I separated the forest for the trees, I was allowed behind the gender curtain or rather followed my woman friends back there. For once, I was on the gender ride of my life. The same one I had paid so many dues over the years to be on, and once I got there, there was no way I wanted to give it up. So, as you can tell, I had a lot of help finding the real me. Women like Liz, Kim and Nikki showed me the way with their knowledge of playing in the girl’s sandbox. They all helped to bring out the true me in ways they never knew as my male past faded into my rearview mirror for good. It was the only time in my life that a mirror made the right call for me.

Needless to say, finding my true self after all those decades really opened the world up for me and made life so much more pleasant. Since I was not suffering from all the gender in-fighting I was going through, my mental health improved along with everything else. It did not hurt that the HRT gender affirming hormones I was on were making serious in-roads on how I felt internally as a trans woman and how I was viewed by the public. I felt better all around.

The only problem that I see now is how long it took me to come up with my own gender truth. If I had faced the facts long ago, I could have saved myself and the people I loved around me all the emotional stress I caused. Finding the true me cost me the most precious commodity I had. My time.

 

Tuesday, March 17, 2026

The Power of Allies

 

Image from Peyton Sickles
on UnSplash. 

I don’t know if I could have ever made it to my dream of living as a full-time transgender woman, without the help of strong allies.

There were many times when I had hit a stopping point on my gender path and was clueless on which way to go. Mainly because I was attempting to find myself as a woman so I could continue to live after a failed suicide attempt.

I have several examples. The first of which came when I first started to go out and secretly wanted to find a social life as a trans woman because I was so lonely after my wife of twenty-five years unexpectedly passed away from a massive heart attack at the age of fifty. In the past I had considered myself a social person, and it hurt deeply to be lonely. At first, I went online and tried the usual methods of establishing a contact or two to date but I ran into the usual problems of inviting all sorts of trash into my life, which included many no shows when I had arranged to meet someone in public. Which was the only way I would do it for personal safety reasons.

In the meantime, I was fortunate to escape the gay venues I was going to (where they thought I was just another drag queen) and establish myself in a couple of the big sports bars I used to go to when I was a man. Places where I could drink pints of beer and watch sports on big screen televisions. Ironically, being alone in one of these venues led me directly to my first two powerful allies.

The first happened to be the mother of one of the bartenders who set up a casual date between us one night where she worked. It turned out we got along really well, shared the same interests and set up future dates, so my end to the extreme loneliness I was feeling was looking like it might me coming to an end. I was further encouraged not long after that when one night a woman came in to pick up her to go food order and suddenly slid her phone number down the bar to me, to my amazement. Not long after that, I kept the number and had the courage to call it.

From that point forward, the three of us made an inseparable trio as we watched sports and drank beer in the venues we met in. Plus, as it turned out, the two women turned out to be lesbians which put a unique perspective to my life as I was regularly attending lesbian mixers and learning any thing I could about the culture which was so new to me. As we socialized together, I was learning as much as I could about being a woman. The first major lesson I learned was that I did not need validation from a man to be a woman which was a relief because of two reasons. The first being that I had very little interactions with men at all primarily I think because I was not attractive enough. The second of which was I really did not want to deal with all the drama I knew men can bring from all the time I spent as a man. I knew how to deal with ciswomen all my life and felt more comfortable with the drama women bring. I always had more women friends than close male friends.

The two most profound allies were yet to enter my life at that point.

As part of my online searches, I did have one response from a Wiccan/lesbian woman in nearby Cincinnati, Ohio. She told me I had sad eyes from my online picture, and we slowly began to correspond by text messages before I felt comfortable enough to talk to her in person. Finally, I got over my shyness and after talking to each other I decided to ask her out on a date. She accepted, and we decided to meet halfway between our homes with friends and go to a drag show at a well-known gay bar. We ended up having a great time and decided to set up another date. This time with my other friends at a women’s roller derby event. I was in gender heaven to be able to go with three other women to one place and enjoy myself for once. My help from allies was coming through for me.

At the same time, I needed to come out to what was left of my blood family. My parents and most of the rest of the family had passed away, leaving only my daughter (only child) and my only brother to come out too. I thought at the time I would have problems with my brother and hopefully not my daughter and I was right. My daughter’s only real reaction was why she was the last to know and my brother totally rejected me by not inviting me to the annual Thanksgiving Day dinner. He sold me out to his rightwing religious in-laws, and I have not spoken to him since which has been over a decade now. I was fortunate when my allies (daughter) and Liz stepped up to help me in my time of need. Not only was I invited to one Thanksgiving family dinner, but I was also invited to two. Even though I was happy to have someplace to go for the holidays, it was quite stressful for me to meet people at my daughter’s in-laws who had known me for years as a man but also meet Liz’s dad and brother for the first time.

The best part of having all of these strong allies on my side was they expected me to be myself. In fact, I was still on the fence of living as both binary genders as I met Liz. It was not too far into our long relationship that she told me the final words to kickstart my final plunge to a feminine life. One day Liz told me what I was waiting for, she had seen both sides of me and had only seen the female side, nothing of the old unwanted masculine me. That was it, I agreed and went about giving away what was left of my male wardrobe and never looked back as I started HRT or gender affirming hormones to further femininize my exterior self.

Along the way, I tried to explain to all my ciswomen allies how much they had done for me, but they would not take any credit. They never understood how much they did to help me become the happy transgender woman I am today. And, by the way, Liz and I finally got married after eight years and now have been together for over a decade.

 

 

Monday, March 16, 2026

It's Complicated

 

Image from Fa Barboza
on UnSplash.

About a month ago, when I was being admitted into a hospital with what turned out to be pneumonia, I had to go through a very complicated conversation about my gender with the emergency room nurse.

Complicating matters is the hospital I have been to before has my gender listed correctly as female, but the nurse had heard the emergency squad driver refer to me as “he” several times after he talked to me about my living situation. When I told him I was married to a woman, somehow, he automatically assumed I was a man. Which I did not care about at the time, as all I wanted to do was recover from whatever was wrong with me. Plus, chances are, I will never see him again (I hope.)

Anyhow, the admissions nurse waded right in with the complicated gender questions. She did ask how I would like to be referred to in the pronoun department which was nice after I needed to tell her I was born as and still was a biological male. Actually, none of the conversation bothered me as I told her I lived fulltime as a transgender woman and was even married to a woman. Where some of the confusion was coming in. She accepted all of that, and we moved on to more important matters such as my medical care. Since I had been admitted to that hospital in the past, I had all the confidence in the world we could move past the complicated part of my transgender self and get on to the real work.

Since I have now been out in the world as my authentic self for over a decade now, normally questions about me don’t bother me. Except in the case of a mammogram nurse, I had several years ago who enquired if I had any “surgeries down there.” Like it was any of her business. I was upset at the question and showed it because then she went ahead and did her job of completing the mammogram. I also consider myself to be an educational curiosity to many people who have never seen or dealt with a transgender person. They have been radicalized by the recent wave of anti-trans political ads and have no way of knowing we often lead similar lives to them and are not the flamboyant style drag queens again on the ads.

Seeing as how I chose a complicated life to live, I need to live it the best I can, and I must say, I have encountered very few haters of gender bigots in the world. Which surprises me. I judge my public gender success on the amount of “he’s” or “she’s” I get when I am out in public. Going back to the hospital, the overwhelming number of nurses and aides did not gender me at all. They did their job and just kept going. All except one day nurse I had for two of my five days who kept infuriating me by calling me “buddy.” As I was stuck with her, I saw no point in explaining how I was not her buddy, for several different reasons.

I have a lot of compassion for those people who don’t understand me if they are not evil about it or want to further take away my rights. Mainly because I try to remember how long it took for me to understand myself and even longer to do anything meaningful about it. If I don’t set my expectations of people too high, then I am pleasantly surprised when they reach my expectations of a good person who of course tries to understand complicated me.

I think too, that growing up with gender dysphoria automatically qualifies you to be more complicated than the average non-transgender person. I know for me, the daily conflict of trying to decide if I was a boy or a girl growing up was a pressure I would not wish on my worst enemy. Learning to live with it was a constant problem I needed to deal with for what turned out to be nearly fifty years before I came to my final decision on how I was going to live. What a relief it was to get the gender burden off of my shoulders and on with life. Knowing completely, I would be facing difficult, complicated life choices ahead on my path to my dream.

It turned out, my recent hospital visit was just a reminder of the life I was trying to lead. I spend too much time in my cocoon away from the public. When I do get out, I am fortunate to have my best ally Liz to lead the way. If anyone is on the fence concerning my gender, when she continues to call me she, it really helps to set the tone and pave the way for public acceptance, A prime example was the recent bus tour to Florida we took. All the interaction Liz had with the other travelers set me up for success.

If you are contemplating going down a similar path as I did, just be aware that it will be complicated but on the other hand (as Emma said to me in a recent comment, very interesting.) For whatever reason we choose this path to our dreams of living as a transfeminine person, when we keep in mind what the difficulty factor in doing it is, we are better off and well adjusted to the new world we are in. There are few human efforts as inherently difficult than crossing the male to female gender frontier. The gender euphoria is worth it though when the public reaffirms who you are and you can finally come full circle back to the person you were always meant to be. They will never understand how difficult and complicated your journey was.

When you make it interesting too, you really have been able to make your life a success. It is for you and only you to understand.

 

 

 

 

Sunday, March 15, 2026

Living in the Real World

 

Image from Jacqueline Mungala
on UnSplash.

Living in the real world became a challenge to me as I transitioned from a male existence to a feminine world. The main problem I had was figuring out what was right and what was wrong as I followed my path through many blind curves and stop signs.

One thing I never thought of completely was how different my life would be if I had ever had the chance to live as a fulltime transgender woman. Sure, I was not totally naïve and thought my world would basically involve pretty clothes and being chased by boys. When I finally was allowed behind the gender curtain, I discovered how complex and layered lives ciswomen really live. Very quickly, trying to live in the real world as a novice struggling trans woman got me in over my head. I would be remiss if I did not bring up how I tried to present myself. I thought trying to look like a sexy teen girl was the way to go, and fortunately my time in that cross-dressing phase of my life went away quickly. Often with brutal consequences of being laughed out of any venue I was trying to visit.

In other words, I put what my male self was telling me about presenting as a woman in the real world behind me and started to look around to what I needed to do to blend in with the other ciswomen around me. The challenge was not only did I have to be as good as the next woman, I needed to be better to survive in the real world I found myself in. With success, I brought confidence I could do more.

The next problem I faced was what was I going to do about my deteriorating (already fragile) mental health. As luck would have it, I was assigned a qualified therapist within the Veterans Administration who knew what she was doing and was able to separate my Bi-polar disorder from my gender dysphoria issues. She provided me with permission to begin HRT which is something I had always wanted and made the real world more livable for a transfeminine person like me.

At the same time, I was trying to take every spare moment away from work to explore different venues as a trans woman. I was attempting to accomplish trying out (as much as possible) everything I would have to go through if I ever followed my dream into womanhood. What was a ciswoman’s life really like and how was it different than what I had already lived as a man. I was entering the scariest yet most exciting time of my life as for the most part I was successful when I went out. The biggest issue which eluded me, was being able to communicate effectively with the world of women I encountered. Learning all the nuances of non-verbal communication women use was the biggest challenge for me. For the first time in my life, I needed to really listen to what was being said to me and watch the other woman’s eyes at the same time to see if I could catch a clue of what she really meant.

Through this portion of my life, I had a powerful motivation to succeed as a woman in the real world. My second wife of twenty-five years had unexpectedly passed away to leave me completely alone with my gender issues. I had no spouse to worry about how to tell my truth about wanting to be a woman. Yet another terrifying yet exciting time of my life. What was I going to do about my newfound freedom. Since you are reading this post, you know what I decided to do. I started making plans to finally make the leap off the gender cliff I had thought of for some time and throw caution to the wind for the remainder of my life. I figured why not because my confidence was at an all-time high with my small circle of friends I had built up. Along with factoring in all the time and effort I put in exploring the real-world ciswomen live in because for once, I had earned my way (or forced my way) behind the so called “sacred” gender curtain.

Once I had made it to this point, after another stop sign on my transgender path, I found I still had more learning to do to really be ready to live in the real world. That is where my ciswomen (lesbian) friends came in which is a subject of another blog post. I will say, they taught me how to be validated as myself in the real world. It was another main transition to go from thinking I was a transgender woman to knowing I was just me. Which took me from cross-dresser to trans woman, back to a secure me during my lifetime. A long, often brutal journey which had a happy ending. I learned the person I had been running from much of my life was not such a bad person after all.

Maybe, most importantly, I discovered the one aspect of my life I never thought I could experience and that was having the ability to be happy. I never had a chance to learn it from my family, and I spent so much time trying to deny myself any satisfaction I could have had from a successful career as a man, there was no time to ever be happy. It turned out that when I turned the corner back to just being the true me, I allowed happiness to be part of my existence.

I had survived all the lessons I had learned as I followed my path to a brighter, more authentic gender future. Living in the real world was not such a bad thing after all. My only regret is that it took me so long (all the way till sixty) to have the courage to face my truth so I could live as I truly was.

 

 

 

Friday, March 13, 2026

The Power of Fear

 

Image from UnSplash.


The power of fear has always been a major factor to be dealt with as I made it through life.

At the beginning, I always used to run from fear by heading home to my makeup and skirts. Then, when that did not work as well, I needed to find another way to deal with the stress my fear brought on. All of a sudden, the extra feelings I brought to the whole cross-dressing experience began to be intertwined with the fear I felt about having my deep dark secret discovered. Every time I was not discovered, the relief I felt was intense.

As I grew older, the stakes I felt grew bolder when I took my image in the mirror public and into the world. The more I attempted to do it in public, the more my fear of discovery grew right with it. I guess it was because at the same time, my male life was flourishing and it was becoming riskier to give it all up, no matter how self-destructive I continued to be. I operated with the idea that if I had nothing to lose in life, it would be easier if I was discovered and life as I knew it came to crushing down on me.

My prime example of turning abject fear into success came from the night I decided to try going into one of the big venues I had visited as a man but this time as a woman. Something clicked in my mind, saying I was no longer a cross-dresser, I wanted more, like a ciswoman in the world doing the same things I had done as a man. Before I did though, I needed to see if I could even cross the threshold in the TGIF Fridays I was going to, to try to find a seat at the bar. Sure, I could have chosen a table instead, but I wanted to go all out and try to look for more interaction at the bar instead.

As I sat in the car, before I went in, I was literally so scared I could hardly breathe. I don’t remember how many times I checked my hair and makeup in my car mirror. Finally, I had enough, hitched up my big girl panties, took a deep breath and headed for the venue’s entrance. Deep down I knew if I was successful, I was facing yet another major transition point in my life and I knew I could never go back. Spoiler alert, I worked my way through all the fear I was feeling and managed to have an enjoyable time with the rest of the women just getting off work at a nearby mall. Even to the point of ordering another drink. Plus, I was right, I found my life could never go back to the male existence I was forcing myself to live. I had discovered new transitions as a transgender woman in the world.

More importantly, I discovered fear of what I was about to do in my new exciting world just came with the territory. It became as much a part of me as a well-worn set of panty hose when I went out into the world. Eventually, I just learned to live with my misgivings about giving up all my male privileges I had earned in life. Another example came much later after I had completed my male to female femininization, even to the point of starting HRT, or gender affirming hormones.

It happened one hot summer day when my future wife Liz suggested we go to one of those auto junk yards where you pick your own parts. We needed a side mirror for one of our cars and it would be much cheaper if we could find one there. All of a sudden, my old fears materialized about going back into a male-dominated environment. Again, I remembered the old days when I battled fear all the time and I had to keep reassuring myself I was not back in the not so good old days, and I would be fine. It turned out, all the fear and trepidation I felt about going was wasted because the men at the junk yard barely noticed me as they went about their business and we found a mirror for our car.

These days, since I have been out in the world for over a decade now, almost all my lifetime fears and anxieties about being a woman have passed like I do most of the time now. Mainly, I pass now as old which there is nothing I can do about. There are times when I do miss the adrenaline flow of being afraid propelled me into the world as a novice transgender woman. I do think, however, that conquering my gender fears came from my days in Army basic training when everyday we needed to fight to make it through. Then somehow, I used it all to help me be a better woman. Before I became a better man at the very end before I transitioned because I was allowed behind the gender curtain to get a look at how ciswomen live.

The end result was that fear helped me battle through the conflicts I felt because of gender dysphoria. It sounds different I know, but that is the way it worked for me.

 

 

 

Thursday, March 12, 2026

In the Snake Pit

 

Image from Jeff Turnale
on UnSplash.

Before I made my male to female transition, I always assumed men were the fiercer competitors, mainly because of work and sports.

Once I made it behind the gender curtain to play fulltime in the girl’s sandbox, I found that my idea of gender competition was not true at all Ciswomen compete every bit as hard as men just in different ways and about different things. A well-worn example could be that women compete in the visibility arena all the time, and that may be true to an extent as ciswomen lay down certain fashion perimeters women have to live by to not cause undue attention. Such as wearing skirts and dresses too short or having non-age-appropriate hair (which I have) for my advanced age. At my age, I have decided to keep my hair the way it is because number one, I like it, and number two, I don’t really care what other ciswomen think of me.

Over the years, I have discovered that ciswomen compete as much as men for the chance to be attractive and attract male attention. In fact, I have a couple of examples where I was caught on the wrong side of female wrath. One of which occurred one night when my wife Liz and I were out in a LGBTQ friendly venue in downtown Cincinnati. During our visit, I needed to use the women’s room which happened to be downstairs in the ancient building the venue was located in. When I made it to the room, I found it to be a crowded two stall affair with several other women already there. As I went in one woman in particular glared at me as I made my way to the only open stall which was left. I excused myself as I went around her and took care of business, feeling better about myself.

As I came out of the stall and headed for the sink to wash up, I needed to almost move the woman who glared at me. She took her time moving and I noticed she ended up slouching below the electric hand blower/dryer on the wall, and I saw my chance for revenge. After washing up and checking my makeup and hair, I took my time moving to the hand dryer and casually turned it on which ruined the woman’s hair completely. After my payback, I gave her a little smile and left to tell Liz what had happened.

The next example I have of an irate ciswoman, took me totally by surprise in a venue in Dayton, Ohio where I was a regular. That night, my friends were not with me, so I was by myself when a couple sat down beside me. Before long, the woman started up a conversation the usual way, complementing me on something I was wearing. We struck up a little conversation about life without much input from the man she was with. I could not tell if they were married or not. Anyway, before long she excused herself to go to the woman’s room leaving just the man and I together and he started a conversation with me by the time she returned. For some reason, she must have been extremely jealous and thought I was competing for her man because the smile went away and the claws came out. To make a long story short both the man and I had claw marks up and down our backs before they quickly finished their drinks and left. I learned the hard way to make sure I never got between a ciswoman and her man.

The most profound level women compete on is with their passive aggressive behavior. They can be competing just as hard as men, just with a smile on their face. It is a learned attitude most ciswomen learn from their youth because of not being able to physically compete with men. Although I think some of that attitude is changing in some cultures where I see many girls fighting among themselves these days. But for the purpose of most all transgender women, our view of the feminine world does not change as we do when we go from aggressive male worlds to passive aggressive female worlds.

Outside of confronting two women in a rest stop woman’s room a couple years ago in Alabama, I don’t think I have ever found myself in a feminine snake pit ever. The two women I encountered were studying me way too closely and talking aggressively between themselves after they saw me, so I washed up and quickly headed for the exit before I had any other problems.

My best advice is to look ahead at your surroundings to not get caught in a feminine snake pit. My worst-case scenario happened when I had to go one on one with a woman in a bathroom in a venue where I had never been questioned before. She was screaming at me that I was a pervert. When I finally could get a word in, I asked her by chance what she did for a living and I saw my chance for revenge creep in. She said she was a hairdresser, so I asked her for a card so I could report her to the very powerful local LGBTQ establishment in Dayton. With that she stormed out and left me alone.

Even though being in the snake pit with other women was no fun, I looked at the entire experience as a rite of passage into the girl’s sandbox. If I could not survive the pit, how could I ever survive my chance to play behind the gender curtain. All my years as a man had taught me to beware of where the frontal attacks were coming from, and if I was ever going to make it as a transgender woman, I had to expect not everyone would accept me and be ready for it. I just never realized how close together the snake pit and the sandbox were going to be.

 

 

 

Tuesday, March 10, 2026

Off...to see the Doc.

 

JJ Hart, back row on left. Girl's night out. 

This is going to be a short post this morning because I have a virtual Veterans’ Administration appointment this morning with the person who checks in and monitors my depression and anxiety medications every three months.

Every time I need to check in, my anxiety goes up because I think this could be the last visit I have with my long-time host Regina. I am afraid of VA cuts by the orange menace in Washington who is trying to get our country into WWIII just because of his involvement in the Epstein files.

Getting back to Regina, she has been with me for years and understands the fact that I am transgender, and more importunately, it has nothing to do with my depression issues, or anxiety for that matter.  She is very careful not to misgender me.

Perhaps, more importantly to me, is my endocrinologist visit which is coming up in approximately a month. The problem is that I am running low on my Estradiol and will need another set of refills. When I talk to her, I am considering asking about switching from the patches I have been on for years to injections because the last time I had my blood work done, my estrogen level was so low. I will have to see what she thinks. Then, there is the fact that the VA keeps making noise about doing away with all HRT therapy in the future, which compounds my problem.

Past that my rescheduled mammogram is in the latter part of April and of course that is in person. I would never say that having a mammogram is enjoyable, but I will say that it is a rite of passage into womanhood for me and always has been.

I guess, multiple medical appointments are part of getting old and I should just accept them for what they are, a chance to stay healthy. Plus, I am fortunate that the VA is going to more and more virtual visits which saves me the time and money to drive to appointments. I must take the good with the bad and not risk being misgendered in the waiting room every time I go. Or at least not being glared at, which sometimes is just as bad.

Now I must get ready for my appointment with Regina, I just hope she is still there.

 

Monday, March 9, 2026

Set in Stone?

 

JJ Hart

When we are born, we are assigned a gender which is arbitrarily based on our genitals the doctor sees. Often, at that point, gender reveal parties are set up by new proud parents. Of course, the problem is what if the child does not agree with how the reveal was going but had no say in the process. That was exactly where I found myself.

I was born as a first son into a male dominated family, so as I grew, I learned what was expected of me. Be a success, compete for it and earn my male privilege was my only path. I was caught with no way out, seemingly, I was stuck in stone. My only path to sanity was the very limited time I had to cross-dress in front of the mirror and try to transform myself into the pretty girl I always wanted to be.

The first time I saw a glimmer of hope in my future as a transgender woman was when I started to go to Halloween parties dressed as a woman, just to see how I was perceived. Overall, I felt as if I got a fair reception and could not wait for Halloween to roll around again. I found I could not wait and began to come up with other ways to test my feminine presentation in the public’s eye by simply going out to malls and women’s clothing stores. Looking back, some of my adventures were just OK and others were brutally bad as I learned what I was doing. One of the main things I learned was presenting as a woman was not set in stone. Often, I could take advantage of the seasonal variations in women’s fashion to change up my own look, which made the fashion process so much more challenging and fun. I needed to up my diet game to fit into more stylish clothes I hunted down at the thrift stores I shopped at. I liked many of them because I could try on my potential treasures in the women’s dressing rooms with no problems.

All of this led me to believe that maybe my gender situation was not set in stone, perhaps I could find my way out of the life I was given. I just needed to be sure that escaping the stone I was in did not put me in quicksand. Or was the transgender frying pan worse than the fire. With my newfound confidence, I set out to discover the answer to as many of my gender questions as I could. I knew I felt an energy in life I had never felt before and it felt so natural that I wanted to experience more. But even with all of that, it wasn’t enough to keep me satisfied with my slow transition. The basic question remained that could I ever gain the courage and where with all to live my dream of existing as a full-time transgender woman on my own terms. Sadly. I was not going to learn that answer for years because my male life kept getting in the way.

By in the way, I mean he kept setting up major roadblocks of my proposed path such as what to do about my wife of twenty-five years and the very successful job I had worked so hard to get. I cherished both of them and did not want to let them go. I am sure, this sounds familiar to many of you in the same situation. Especially when you think your male situation is set in stone and you can’t get out.

I thought the same thing for years as my mental health deteriorated as I drank way to much trying to self-medicate my problems. The part I never understood was how I could think what was true today would be true tomorrow. Destiny for me completely turned me around during the dark days when my wife and almost all of my close friends passed away, leaving me almost completely by myself. Except for my daughter and my brother. On top of all of that, the Veterans’ Administration healthcare system, which I was a part of suddenly approved the use of HRT or gender affirming hormones for qualified veterans who were approved through a therapist to receive them. I was approved and prepared myself for my second puberty and the greatest most profound changes of my life.

Suddenly, everything I thought was set in stone, was not. I was free to live the way I had prepared for all my life had come true. I could even dare to be happy for the first time in my life. It was always set in stone that happiness could not be part of my life. Thankfully I was wrong about that. It was just a matter of learning where I truly belonged and then getting rid of that giant roadblock I was born with. My so-called gender because it turned out to be true, I was never supposed to live a male life after all. All the years of struggle and emotional pain were wasted on a fight that I was never destined to win.

As I always say, I was not a man cross dressing as a woman, I was a woman cross dressing as a man to just get by in life. I was fortunate in that my gender destiny was not set in stone no matter how determined my family around me was to keep me male, I always found a way to sneak around their backs and keep that feminine flicker of hope alive. Now it is able to burn brightly due to no small help from mainly new friends and family. Roadblocks were moved and now the path is straight and smooth as I am able to live the dream I always wanted.

As I said, remember that today does not dictate what tomorrow may bring. I always say, life can change on a dime. If you can find the dime.

 

 

 

Sunday, March 8, 2026

When Gender Calls

 

Image from Brooke Cagel on UnSplash. 

When I was very young, when I listened closely, I could hear the faint sound of my true gender calling me.

Please keep in mind that very early on I could not quite understand what the voice was trying to tell me. I just knew something was not right. As I grew older and started experimenting with Mom’s clothes (even to the point of shaving my legs), did I have a basic understanding of what the voice was trying to tell me. From the first view of myself in our full-length hallway mirror, I had an idea that I had arrived in the right place as I stared at the pretty girl that I had a hand in creating.

It was then that the real gender work began. The first problem I had was trying to find the private time I had to cross-dress. And once I did, when would I have the time to do it again as the gender pressure built on me every time. What I did not understand and wouldn’t for many years was that I was much more than someone who just wanted to wear pretty feminine clothing. My true gender was calling and would never be satisfied until it was properly expressed. Even though I did not fully understand the path I was on and would have to accept it over the years to come. Especially all the blind curves and stop signs I ran into. I was not prepared for all the trials and tribulations I would have to go through to even try to pursue my gender dreams which always had to do with living a transfeminine life. At that time, the phrase had not yet been invented or used, so all I knew was I wanted to be a woman with all the perceived benefits which came with it.

Jumping ahead, the benefits of living as a full-time trans woman were there but just vastly different that I thought they would be. I still had the joy of selecting and wearing pretty clothes which changed with the seasons. It turned out, some of the enjoyment was taken away when I needed to pick out an outfit every day when I gave away all my male clothes and the reality of my existence set in. I guess you could say the novelty of dressing like a woman became a necessity when my gender called.

Speaking of my gender calling, I needed to learn how to accept it when it was trying to get through in my busy life as a man. I knew who was calling all of the time, I was just afraid of facing the reality of me answering it. I ran from it until I could run no more and I had myself painted into a feminine corner of reality I could not get out of.

What I am referring to is all the nights I went out as a trans woman to be alone and ended up socializing and carving out a new life faster than I ever thought possible. Suddenly, my gender phone was ringing off the hook and demanding more and more attention. The conversations became deeper and deeper as discussions about spouses, family and jobs took center stage. At a crucial point, I needed to lose all my fears of debating the pros and cons of gender change and consider the future which increasingly looked feminine to me. I respected the world of ciswomen from all angles, and I wanted to explore my desire to fit in more and more.

Finally, my gender voice became mildly abusive and challenged me to think deeply about the life situation I was in. What was I doing by constantly fighting a situation where I felt natural and good at. For once, I put my stubborn male self behind me and listened. Sure, there were bound to be bigots and haters still on my path, but I would have to ignore them and stand up for myself. The availability of gender affirming hormones or HRT helped me a lot because the hormones softened my skin and harsh male facial angles and made it easier to present a feminine face to the public. Which in turn, gave me more confidence. For the first time in my life, my external and internal features came close to matching.

At least now, my gender voice could quit screaming and calling me stupid for the way I was trying to run my life. Then perhaps, I could answer my gender phone and think about more pressing issues such as how I was going to run my life as a successful, happy transgender woman since happiness was something which eluded me for most of my life.

During a classic “if I had known then what I know now” moment, if I had known way back in my past how deep my gender issues ran, I was so much more than someone who enjoyed wearing feminine clothes. I wanted to be a woman as my ultimate goal in life. It would have been nice too, to have other guidance to help me along in my gender dysphoria struggles. In those days, not only were there not any qualified therapists to help, but there also wasn’t even internet to refer to for information so our closets were very lonely and dark.

Certainly, the one thing missing in my closet was a phone so I could talk when gender called. Maybe it would have saved me a great amount of stress and turmoil. I say maybe because of who knows, I would have had the maturity and courage to lick up the phone and have a honest and far-reaching discussion with myself about who I really was.

Maybe, when your gender calls, there will be a real person such as a supporting spouse to talk to about your life. So many transgender women and transgender men don’t have that luxury. One way or another, pick up the phone and talk. It could be the best therapy for you.

 

 

 

The Winds of Gender Change

  Image from Taylor Flowe on UnSplash.  Per normal, we have had a very windy spring here in southwestern Ohio USA. For some reason, I have n...