Thursday, July 2, 2026

The Best Advice I Never Got

 

Image from Frame Harriak
on UnSplash. 

The best advice I never got came from no one.

There was no one there to tell me anything about what I was doing when I was doing my best just to be feminine. No one to tell me my skirts were way too short and tight and my makeup looked like I just left a circus clown drag show. And better yet, no one to tell me I was heading along a gender path which would ultimately ruin my life if I kept it up.

The only person who was screaming in my ear initially as I cross dressed in front of the mirror was my male self-telling me to hurry up and get done before I risked discovery and the end to the world as I knew it. This was the time too when my feminine side was lying to me by telling me I was a pretty girl. Maybe I could see some of my femininity in my pre-male puberty years but quickly faded with my bodily changes.

As life progressed as it always does, I witnessed the battle of my voices as once again my male side was telling me to stop cross-dressing and never do it again and my feminine side saying keep on trying and things will get better. Even though it was difficult to listen to the best advice I never got I kept deciding to pursue my feminine side and see what would happen,

At that time, I was stuck in a series of Halloween parties where I could dress as myself and not fear reprisal. Plus, I could judge how I was doing with what I wanted to wear and with how far I had come with my makeup skills or lack of them. I was aware that I was at risk for stirring up potential risks of being discovered when someone would ask who shaved my legs and applied my makeup. I just said I shaved my own legs and did not mention who did my makeup because my second wife did not wear any. I was normally Ok because it would take another ciswoman to question my makeup because if a man did, I would figure he may be part of my femininization club. I learned so much from the Halloween parties I went to that not going to them dressed as myself was the best advice I never got.

I think it is ironic that that almost everyone has advice for everyone else except when it comes to transgender women and transgender men. It seems, our situation is so unique that the only advice someone can come up with is just not do it. They have no understanding of what we are going through, and it is so much deeper than just wearing clothes of the opposite gender. Maybe that is why I never got any advice from anyone except one of my self-proclaimed gender therapists who told me there was nothing she could do about me wanting to be a woman. Like a dummy, I ignored the only good advice I could have received at the time.

It wasn’t until I started reading certain on-line computer sites did, I really encounter advice as transgender “Nazi’s” as we called them. Who continually did battle with many cross dressers, who received little or no respect from the transsexuals as they were called then. Being the cynic that I am, I enjoyed quite a few of the comments as the gender battles raged on. Seemingly, respect from some on the site was only gained by how many gender surgeries you had gone through. Why I needed to wait to receive advice I did not want from an internet site which should have been welcoming to all but wasn’t.

By the time I hit my experimental stage to judge where I should be in the world as a man or a trans woman. I was not in much of a mood for much advice, and it was the best advice I could ever get. I was very much on my own in the world as a new transfeminine person and loving it. If someone had told me to stop what I was doing, I would have said hell no as I was having the time of my life.

I think other ciswomen sensed my confidence in who I was and mostly just interacted with me out of curiosity and at the same time, without knowing it showed me the way behind the gender curtain. I needed their help to achieve my dream, and not much advice. As the curtain parted and I learned what I needed to exist in a world I had only dreamed of, the best advice I got was none because I did not seek it out.

I cannot say I did not need advice when it came to making my final gender decisions. Primarily the day when my future wife Liz saw me mentally struggling again with my gender issues and flat out told me she had never seen any male in me. Go ahead and transition into a feminine world. In all fairness, I heard the same thing from my second wife years before but could not figure out how to do it. This time I could do it and received a doctor’s approval for HRT gender affirming hormones and major changes to by external and internal body was underway.

It turned out to be the best advice I ever got. Especially when my stubborn self-listened and decided to change my life for good. To the place it should have always been. Making my way in a world of ciswomen. Now I want the time back that I lost, but it is too late. I will just have to take my own advice and make the best life I can with the time I have left.

Thanks to you all who read along with all my experiences. Hopefully they will help you with yours and of course I will offer my own advice from all that I learned when you comment. Without all of you, none of what I do would be meaningful to me.

 

 

 

Wednesday, July 1, 2026

The Consequences of Giving Up

 

Image from fast glass fx 
on UnSplash.


When I considered “purging” (getting rid of all my feminine makeup and clothing) the consequences felt like a double-edged sword.

For a few days, the pressure around gender lifted, and I had one less major worry. But before long, the familiar desire to live as a girl returned to my everyday life. I realized that cross-dressing—and perhaps something beyond it—would not be easy for me to give up. Even in that short time, I had learned a great deal and understood how far I still had to go before reaching my dream of living full time as a transgender woman. I was not even sure whether I could make it happen.

Then there were the brief moments of gender euphoria. The time I spent hiding from my brother and family was enough to keep me going until male puberty—and what felt like testosterone poisoning set in. I was unhappy that my body was becoming more angular while the girls around me were developing curves, but there was nothing I could do to stop it.

Even as those changes continued, I could not face the consequences of giving up. I learned to take what I could get until I was old enough to leave the mirror and closet behind and explore the world. What happened next was brutal. I discovered that the mirror had been lying to me when it suggested I looked like an attractive woman. If that were true, why was I laughed at so often when I tried to go to ordinary places, such as nearby shopping malls? Eventually, my frustration pushed me to look around and notice how most of the cisgender women I saw were dressed. Even if it meant adopting the casual styles I dreaded, I knew I needed to do it to blend in and be accepted.

The more acceptance I gained, the harder it became to return to my old life and face the thought of giving up on my dream. For the first time, I even felt excited about where my future might lead. I just had the glimmer of hope that I might be able to make it to the transfeminine life I always wanted to lead.

At that point, my male life began to creep in with a vengeance. He was becoming very successful with a small family and good job and the risk of giving it all up loomed large over everything I did. Not a day went by when I didn’t consider the consequences of what I was doing. I always say, I wish I could get back just a fraction of the time I wasted worrying about how I would be living my life if I was a woman. What would become of me if I jumped off my gender cliff for good.

What I decided to do was experiment in the world as a trans woman. My second wife called me a “terrible woman” because I had never paid any dues that ciswomen pay, and all I was concerned about was my appearance. I knew deep down she was right but I still at that point did not know how to fix the problem by paying my dues as a novice feminine person in the world. It was like if you are applying for a job, the employer says you don’t have enough experience but will not give you the job so you can get it.  I am sure my wife was right about my feminine knowledge, but I was having an impossible time getting behind the gender curtain to learn more.

As I slowly got behind the gender curtain, the consequences of giving up almost completely went away. Why would I abandon all the effort I put into being a complex transgender woman and throw it all away during a time when I was finally being successful. For a change, I was the one making sense in a gender situation which very few understood.  No longer could I be accused of being a terrible woman as I matured into my new self when I was allowed into women’s only spaces. Sure, I was still making mistakes, but they were getting smaller and smaller as time went on.

The mistakes I usually made came from when I miscalculated how complex a ciswoman’s life really was and how far I needed to go to be allowed to fit in. To eliminate all my mistakes, I needed to give up all the negative consequences of a male to female gender transition and just make the plunge. Fortunately for me, the water was not that cold, and I jumped into the deep end of the gender pool. Plus, I can never forget the soft feminine gender hands which helped me to survive the impact into the water.

I know many of are thinking seriously of making your own gender plunge and what would be the consequences of possibly losing everything you hold dear in the world. I know advice is easy to give, but the turning point for me always was how natural I felt as a transfeminine person. Something kept telling me I was born the way I ended up. And with some effort, I made it to where I always needed (not wanted) to be. Hopefully, that is a starting point for you too and the consequences of giving up become too much to consider.

If you are further along, I am sure you recognize the consequences of never giving up and somedays even being perceived as being selfish. As I was when I was headed all out to fully transition into a transgender woman, all I could think of how fast I could make it to my goal. So, I am guilty as charged. It is probably the reason my second wife called me a terrible woman. In all fairness to me, I did mature out of it and found my way into a better world.

All the purges in the world did not work for me and I put up with all the consequences I lived through. I am not a gambler, but in this instance, I played the odds and won.

 

 

 

 

 

 

Tuesday, June 30, 2026

I Was Afraid of the Truth

 

Image from Brett Jordan
on UnSplash, 

It took me a while to understand that facing the major truth in my life was not possible early on for me.

As I cross-dressed in front of the mirror in my early years, I could not believe it would be a part of my permanent existence. Even though, it was screaming at me that it was. I learned quite early, just looking like a pretty girl (or so I thought) for just a quick moment in time never held up and very soon I would be wondering what it would be like to live among the girls around me as one of them. In other words, I did not know I was much more than a casual cross-dresser attracted to feminine makeup and clothes, I was so much more. Later I would learn I was a transgender woman when the term began to be popularized.

Even when I realized, for the first time in my life, I had found a term which described me, I did not totally accept it. My truth still evaded my consciousness.  I was afraid to face it and lose all the male privilege I had built up.  All along, I resisted building up those benefits, but then again took them when they were offered. Which deep down made me feel like some sort of a gender hypocrite. Regardless of my guilt, I needed to work my way through my gender issues all alone and I had no gender workbook to follow. No all-nighters with girls my age to learn what it meant to play with the essentials of makeup and clothes all the way to learning the foundation of what it would take to build me into a mature transfeminine woman someday. If I worked hard enough on my goal.  

I was frustrated even more when I got the tiniest bit of gender euphoria when I was able to go out in the world for the first time as a trans woman and do my own clothes shopping in women’s clothing stores. Even to the point of being emboldened enough to use the changing rooms to make sure my selections fit me as well as could be expected before my weight-loss program. Increasing my shopping confidence was the fact that the clerks did not really care about my gender as much as they did about my money. Another truth I needed to learn the hard way and not be so naïve.

The deeper I got into the world of cisgender women, the more I wanted to stay. As my time behind the gender curtain was beginning to feel so much more natural every time I did it. Sometimes, the whole process felt so good, I almost panicked because I did not know if I was ready yet to give up all my male existence. I had too much vested in him to just give him away, so I continued to explore my new world as a transgender woman.  

My bottom line at that time was again what was I going to do about an unapproving spouse who was still my best friend and major problems about what I was going to do about finding work as a new trans woman. I was intimidated and forced to deny my gender truth for many more years. I tried all sorts of ways to do it. I tried everything from therapy, to trying to drink it away, to trying to outrun my truths by changing jobs and moving my family many times. Of course, none of it worked and still I refused to face the facts that were staring me down in the mirror every morning that I was not meant to be a man at all. It was like life was playing a cruel prank on me because on occasion I could still be a success in a male life without really wanting to. It seemed that every time I did enjoy myself as a man, my woman self would come along and do him one better.

Finally, I had reached the point of no return and just had to begin the series of moves I would have to make to put my male behind me forever. Tragically, my wife passed away leaving me alone to do whatever I wanted, and I was old enough to retire early and sell collectibles online to scrape up enough money to survive, so destiny all of a sudden was opening doors for me to live my inner gender truth. And to make matters even better, I even gained approval from a doctor to start on HRT, or gender affirming hormones that I had always dreamed of taking. The changes I went through under the new hormones proved to be miraculous for me. As all the external and internal emotional changes took effect were worth the wait. Even though I waited until I was sixty to start them.

Perhaps the HRT hormonal shift was the final straw in me having to face the biggest truth of my life. I was a woman pretending to be a man all along.

Truth was always hard to face for me as I did my best to run from it or just ignore it…it never went away proving my transgender womanhood was the only way could go if I wanted to respect myself in the end. Plus, the end of my life was not getting further away at my age. If I was going to act, it was a now or never situation.

One night when I was out to be hopefully left alone in one of my favorite venues to watch sports and drink beer, the blinding realization that my male life was over came to me. The only future for me could be feminine if I was going to be able to live my truth. It was when all the disastrous gender wars I had lived with over the years came to an end and I all sudden, was on the right path.

Most importantly, I had worked hard to know it was the right one.

 

 

Monday, June 29, 2026

Dealing with Stress as a Transgender Woman

 

Image from Ksenia Berjoz 
on UnSplash.

In the male world I did not want to be in, I had a difficult time responding to pressure except where I worked where oddly enough, I thrived.

I suppose the gender pressure I was under started very early in life when I needed to struggle mightily to even find the private time to even try to be the pretty girl I wanted to be in front of the mirror. From my early cross-dressing years, instead of growing away from feeling the pressure I was feeling, I grew into it. On one side, I had the fond thoughts of gender euphoria dominating every spare moment that I had and on the other side I had the reality of having to compete in a world I never wanted to be in. Football was a prime example of me trying to overachieve and ended up breaking two bones doing it before I just quit.

Moving forward to the time when I left my closet and started to discover the world as a novice cross-dresser or transgender woman, the pressure was on more than ever before to succeed as neither of my egos were taking getting laughed at by the public well. My feelings hurt, and the pressure as I said was building to do something about it.

The first thing I knew I could do was go on a diet which quickly slimmed my body so I could find and wear more fashionable clothing and started to take care of my skin better everyday after I shaved. All of this helped me to feel better about myself, and I kept on trying to perfect my makeup techniques to improve my public presentation. With all of this, it still took me quite a while to build my fragile confidence to a point where I could go out in public again.

Then I found myself in a spot where pressure was coming at me from different angles. On the days I thought my makeup and clothes were at their peak of success, the pressure would set in about how I was moving as a transfeminine person in the world. I needed to concentrate on two things, not moving like a linebacker in drag and making sure I put a pleasant look on my face. Replacing the male scowl I had perfected for so long. If I was enjoying my new life, I would have to make sure I showed it to the world.

As I did all of that, my inner pressure began to change once again as I began to free myself from the drag atmosphere of the gay venues I was going to (where I was considered as just another queen) and into the straight world I was used to where I could at least have a fighting chance of being treated as another woman in the world where the ciswomen ruled the scene I wanted to be accepted into. For the most part, I discovered that most ciswomen did not notice me, or if they were, they were just curious why I was trying to play with the girls’ club and leaving the universe of men.

At that point, I nearly panicked from all the pressure I was under as I desperately tried to maintain what was left of my male life which included my wife and job and at the same time try to allow my feminine transgender side to flourish also. My main reason to panic came when I needed to learn immediately how to communicate one on one with other women. To relieve the pressure, I went all out and even took feminine vocal lessons and I had to focus for the first time in my life on really listening to what someone else was telling me because I found that ciswomen were the masters at non-verbal or passive aggressive communication and used both methods to by pass the men around them. Which was the main reason men said they could not understand women. The women had set it up that way.

I did maintain that life as long as I could before the pressure increased again until the forms of relieving it, I was using, just did not work any longer. On top of that, I was becoming more and more self-destructive, and I kept putting my life in danger. Fortunately, before anything severely happened to me because of the pressure I was feeling nothing severe happened to me and I began to build a new exciting life out of the ashes of the male life I used to live. I took what I could from him and added it to my new transfeminine life I was beginning to carve out for myself.

Magically then, much of the pressure I was feeling about my male to female femininization started to drain off me. I can’t take all of the credit because I fell into the open arms of so many ciswomen who had problems of their own and took the time and effort to help me with mine. All their efforts reinforced why I wanted to be allowed behind the gender curtain to start with.

After the pressure was released, it was like the sun came out to me on a cloudy day, I can’t say how much weight was lifted from my shoulders when I finally saw the sunlight and decided to put my male self in my past and begin HRT or gender affirming hormones under a doctor’s supervision.

I can’t say before then I had any knowledge at all how to live a life without experiencing gender pressure. As I matured into a confident transgender woman, I finally realized I did not have to live that way, and I had the built the confidence to change it.

Certainly, living under pressure is no fun, and I would not wish it on anyone. Also, I know everyday humans have stress in their life, but I am biased, but I think transgender women and transgender men have more than their fair share to deal with. How we are able to handle it can define our lives.

 

 

 

Sunday, June 28, 2026

Swimming Upstream as a Trans Woman

 

JJ Hart. Pride image.
Ohio River in background.

I was very stubborn as I hung on to my male persona as long as I could. In the meantime, the struggle between my two genders was monumental.

Since I started life as a biological male, he sprinted off to an unfair advantage over my feminine self. Mainly because, like it or not, being male brought with it a series of benefits I would come to call male privilege. Even though it was hard to do, each time I was moderately successful as a boy I was rewarded. Even though, deep down, I did not want to be because I knew someday, I might have to give up all that hard earned male baggage to lead the life I always dreamed of, as a  transgender woman. Full time without any restrictions.

Along with being stubborn concerning my chances of ever living my transfeminine dreams, I was also very naïve when it came to having a grand plan on how it would ever happen. When I looked at the stream that crossed my gender path, at times it would become a river that was hard to cross to get to the feminine side I wanted to be on. There were times too, when I miscalculated the depth of the water upstream, I would have to face to get to the other side.

As the water subsided, and I could try to get out of my home mirror and into the world, I ran into new situations which would define parts of my life, and I would not know it yet. Such as the Halloween parties I went to as a woman and were immediately shunned by my male friends who were there also. Little did I know that later in life when I began to explore the world as a transgender woman, men shunning me would be a common theme. Ironically, at the same time, I was learning the opposite would happen with women. Particularly lesbian women. For the first time, the stream was busy pushing me in a way I never thought possible. It happened one of the nights I was a guest at the LGBTQIA+ diverse Columbus, Ohio parties I always went to.  That night a lesbian I had never seen before showed up with a friend and the attraction between us was real. We ended leaving and going to a big lesbian venue to see what was going on and we spent the rest of the evening getting to know each other, but I was still married at the time, and nothing ever came of seeing the first lesbian who was interested in me.

All I knew at the time was I was treading water as fast as I could just to stay afloat in the dual gender world, I was trying to live in. One big life jacket which was thrown at me was the attention I was receiving from gay and straight ciswomen. It meant I would never have to approach the potentially unpleasant situation of exploring my sexuality and I never had to go past the point of kissing men at all since most of them did not want to approach me. At any rate, I always thought I was never attractive enough for them, but when I reached an island as I was swimming upstream, I had the chance to pause and realize I did not need a man’s validation to make me a complete transgender person anyhow. There were plenty of fish in my sea and I needed destiny to lead me to one. Which it did with Liz who I later married and have been with well over a dozen years now.

Another thing my stream taught me was to never feel totally comfortable and rest much at all because something would come along and knock me back into the deep water. The problem was I was still catching up on the life that ciswomen grew up living, and it was very complex. I knew it would be, but sometimes I was just caught off guard and think did that really happen.

On the other hand, when I finally was able to relax with all that I had accomplished in my gender workbook, I was so much happier in life. I finally began to realize that I was never a man at all, just a woman trying to live her life from a totally different perspective than most anyone else. Then, it made sense to me why my life was always such a struggle because I had two powerful influences battling each other. The most powerful one had to finally win out, and my inner femininity won out.

If I had it all to do over again, I would have to tell myself to follow my instincts and stay out of the water before swimming upstream became exhausting and I almost went under for good.

I know I have many readers on different parts of their gender journeys looking for any guidance possible. All I can say is that at some point you need to be honest with yourself and decide to take the most natural path you can take. Maybe you can cross-dress enough to keep one foot in the stream and one foot out and that is OK too. I just could not do it that way, but that does not make it right or wrong for you.

For the most part, I still think society is still set up for men to succeed but that is changing. And, when you are a trans person continuing up your gender path, just consider the world is still in flux and the future is feminine no matter long the old white male dinosaurs hang on. Regardless, either way you must make your own way in your own gender stream, and you will have to expect at some point to swim against the current. It is just the nature of the beast we transgender women and transgender men must face in life.

Just be very careful and follow your true gender core and you can make it.

 

 

 

 

 

Saturday, June 27, 2026

Exorcising my Demons

 

Peaches Grille, Yellow Springs, Ohio.


Yesterday I went back to my hometown to pick up copies of court paperwork I needed on my name change so long ago.

By so long ago, I mean I finally had to sit in front of a judge who I knew to be very conservative to get my final name change signature. It was one super Christmas present as it all happened December 23, 2015. Even “Mr. Conservative Judge” himself said Merry Christmas when he signed my long overdue paperwork. As I remember now, I had many hoops to jump through such as posting a notice in the local newspaper and waiting for thirty days to see if anyone would object to the change. Then I needed to petition the court for the actual name change. My future wife Liz was with me when all of this happened, and we were on cloud nine when we received the final documents.

The only mistake I made was not getting enough court copies of my change due to poor planning and I ran out. So, the only thing I could do was make the hour and a half trip back to the court clerk for more certified copies that I needed to change one of my insurance policies names over from my old name to my new name. My only advice to those of you who are going through the legal name change process is to plan ahead and get plenty of copies and then get more.

By now you may be asking which of my demons did I exorcise. The first major demon was not having to see mail from my insurance company showing up with my previous male name on it and knowing it was not their fault but mine because I did not do anything about it. The second demon was even going back to my hometown (where I was born and raised) at all. It is an old industrial town which has had its heart ripped out a couple times by companies downsizing or even moving overseas. Setting all of that aside, I remember the rejection I received there from certain friends and family members when they discovered my deep, dark “gender secret”. It seems each rejection was burned into my soul.

So much so that I could not sleep the night before Liz and I went back to the city that I think never forgot about me. Even though that is a self-centered idea because it has in almost every way possible. My ex-brother still lives there who I am separated from and is another good reason to dread going back. To take the pressure off a little bit, I tried to meet up with my daughter and son-in-law in nearby Yellow Springs, Ohio which has always been a real treat to go to and has been referred to as the gayest town in Ohio.

My daughter could not be there because they were going to Maine to see my oldest grandchild who works up there as a nuclear engineer. Liz and I’s disappointment in not seeing daughter and son-in-law was short-lived because Yellow Springs was all decked out in its Pride finest as it was all going to happen the next day. We ended up stopping for lunch at a place called “Peaches Grill” for a great light lunch before we resumed our trip. “Peaches” was promoting their after-Pride party and was all decorated out in preparation. It was also the venue where I ended setting next to a “Debra Winger” look-a-like complete with the black “Urban Cowboy” movie cowgirl hat. It was a fun evening and no, she did not ask for my autograph (ha-ha). All in all, Yellow Springs is the direct opposite of my hometown which is only ten miles away.

Now, since I think I have all the papers I will need for any future demands put on me to vote by the Republicans, I am not envisioning any need to go back to my hometown since years ago now, I even sold the two properties I had left there. I don’t know why I have such a deep-seated fear of reliving all the bad moments that I had, I suppose it is just the vestiges of the life I had coming out into the world coming back to haunt me. And it speaks to the amount of suffering a transgender woman or transgender man can go through just to live their lives the way they need to.

I know too that I am one of the fortunate trans people who can get around freely in public since I present as just old now and can get by with my wife’s Liz help. I just have my age-old demons to harass me like I just went through. I dislike my old hometown so much, I even don’t want to mention it by name, but it is the one that the orange Russian in the White House keeps mentioning again when it comes to deporting the Haitians. I will let you fill in the blanks from there.

All in all, my demons are tough critters and the only survivors which still exist from my old male days. They play into my anxiety issues of always worrying ahead for seemingly any occasion. But as always, my feminine side has stood the test of time and has been successful in exorcising my demons. I guess you can say she has always had my back when the times were the darkest in the days when I was visiting Yellow Springs as a short-haired Army soldier when I desperately wanted to be one of the long-haired hippie girls I saw in their bell-bottom pants. It took me awhile, but I exorcised that demon who kept telling me I would never make it.

Most importantly we made the trip safely, even with a police detour set up on a rural highway for what looked like a potential swat situation as well as heavily pouring rain which hit us on and off. We made it past the demons and that is the important part.

 

 

 

Thursday, June 25, 2026

Luck or Destiny makes a Trans Girl Tick

Image from Maia I 
on UnSplash

Along with my regular blog postings, I am writing I book about my life through a company called “StoryWorth.”  My daughter purchased it for me, and it only goes to selected members of the family, so it is intensely personal and made to read in my opinion, after I have passed away. This week’s question was based on what I have done in my life, which was the most difficult to accomplish and what were the lessons learned and did they happen due to luck or destiny.

My answer was an easy one the two biggest accomplishments I had in life which surprised even me were when I was able to be accepted into the American Forces Radio and Television Service as a broadcaster during the Vietnam War. And the other was when I finally kicked my old male self to the curb and started to follow my dream of living my life as a transgender woman. For the longest time, neither seemed to have any chance at all in coming true, but the slimmest of hopes kept my dreams alive.

Along the way, I learned to not believe in luck during my life, however I became a firm believer in destiny. I need to make the point that destiny only found me because I made the effort to put myself out there in the world and try. I would never have made it to AFRTS without all the time and effort I took to write letters to my congressman, and I would have never made it to a transfeminine existence without leaving my closet and experimenting in the world. It was like I needed to scream destiny here I am, now find me. None of it was ever easy as I was swimming upstream against what society said I should or should not do. I should have quietly went about my way and let the Army recruiters have their way without question or had done the same when I rebelled against being in the restrictive gender box I was born into. I just couldn’t do it.

By far, the greatest act of rebellion happened when I went about seriously crossing the gender border. Presenting as a convincing ciswoman never was easy for me as I had very few natural characteristics. Like many of you, I have the prototypical male body with the thick torso and broad shoulders which I needed somehow to cover up if I was ever going to make it in the world as a trans woman. In fact, the shape of my body always threatened to derail all the work I was doing with my makeup, hair and clothes before I ever got started. I don’t think I ever would have made it without me finally taking the time to look at all the different shapes and sizes of the ciswomen that were around me. Like many of them, I would never be thin and attractive but just maybe with the right padding and wardrobe, I could be a presentable thick woman. By “padding” I meant I needed the right size of breast enhancements as well as hip padding until much later in life, I could add my own “padding” through the help of gender affirming hormones or HRT.

Then I started to realize that maybe I could do this and become a fully functional transgender woman, if I worked hard enough at it. That meant I needed to overcome the bumps and bruises I encountered along the way when I refused to stop at stop signs along my gender path. To do it, I needed to build up much deserved confidence in what I was attempting to do. Which was stop my life and start it all over again. It was as if I was packing for a trip and only had so much space to take things along. I had to decide what could stay (if anything) from my male past. Again, I needed to look around at the ciswomen I was close to and notice what their interests were. A major example was when I began to think I would have to lose my passion for sports, I began to notice many women with their favorite team jerseys watching games and drinking beer on the big screen televisions in the venues I was going to as a man. It didn’t take a genius to figure out if they could do it, so could I.

Destiny, in all its glory began to show me I wasn’t building anything new when I crossed to going behind the female gender curtain. I was just going to where I always should have been. I started to see that I could be accepted in lesbian circles as a sports loving femme (or lipstick) lesbian and I was relieved I did not have to institute some sort of a forced sexuality change I never wanted to do. Even though I kissed several men to see if there was any real attraction, there wasn’t so I happily moved on to where I was comfortable.

Believing in myself was certainly difficult to come by and took a lot of learning to do as I switched my life from a fairly successful man to a new transgender woman. Because at times, I thought I was in over my head until my confidence stepped back in and I started to move forwards towards my dream goal once again. I just had to remember how far that I had come from that scared, excited boy in a dress and make-up in the family mirror.

If I had it all to do all over again, I am sure I was given a bad deck of cards when it came to dealing with my gender and for the longest time, I played the victim card to delay the obvious. I was a male only because my genitals told the world I was. It took a while for me to mature into the trans woman I am today. But with the help of destiny, I put myself out into the world and made it. There was no luck to it.

 

 

 


Wednesday, June 24, 2026

What is a New Trans Girl to Do?

 

Image from UnSplash. 

I recently received a comment from “Mira” concerning writing more about what happens when you are a new transgender woman out in the world.

Thanks for the comment, “Mira”, on such a complex subject. The first thing I can think of being so different for me was that everyone was looking at me. As a man, I was used to admiring well dressed and attractive women but got used to the fact that I was nearly invisible to the world as a guy. In essence, other women and men all notice other ciswomen who go out of their way to at least look nice. Which was what I was doing when I went out in the public’s eye to see how well I could present myself as a transfeminine person.

Maybe the most important hurdle I faced at this time on my gender path was looking like I was trying too hard to look like a woman. The initial attempts I tried to make such as wearing too tight and short skirts, produced laughable results when I was laughed at in reality.  On the other hand, you need to take an accurate assessment of your basic strengths and weaknesses and go from there. I know you may think you may have very few strengths when you are trying to dress your testosterone poisoned body, but you may be surprised. Many men are blessed with passable looking feminine legs, which is a place to start building your presentation from. I learned my legs were good from the Halloween parties I went to in my mini dresses. So at least, I had a positive place to start from when I began to go out. Until I began to overdo it and feature my legs over my biggest fashion problem…my broad torso and shoulders. I still wore my denim miniskirts but with large flowing tops which were able to hide my shoulders as I got by.

The difficult part for me was getting any realistic feedback from anyone. The only feedback I received on a regular basis was from my mirror which I found had a habit of lying to me and from my wife who would dismiss me as only being the “pretty, pretty princess.” I did not want to be a princess; I just wanted to present as well as I could in the world as a transgender woman. I understand now what my wife was trying to tell me about being feminine would take more effort than just looking like a ciswoman and I would have a long way to go.

The next big step I took as a novice transgender woman was to not be afraid when someone wanted to know more about me and I don’t mean in a close, personal sense. As most of the many ciswomen I encountered just wanted to sell me something (clothing store clerks) or were just curious about what I was doing in their world. Once they were satisfied, I was not up to no good and I just wanted to be part of the girls’ club, they were happy and went on their way. Except for a few who stuck around and I was able to make friends with. Which came much later in my trans life when I grew more comfortable in my new skin. And speaking of skin, if you are overweight, consider going on a serious diet like I did to slim down and look better in more stylish clothes.

When you are new to all of this, it is easy to feel selfish when you are obsessed with how you look and act as you try to determine if you truly belong in the new world you are exploring. All of that is a natural reaction to letting go of the male world (or female world for you trans men) that you had to work so hard to survive in. Often against your will. Plus, learning all the nuances of a new gender is not and never will be easy. Especially if you transition later in life such as I did. The reality of the situation is that you have accumulated much more gender baggage to deal with over the years, and you must start deciding early on what you are going to do with it.

Backtracking a bit, what I remember the most about my early years as a transfeminine person was the panic I felt when I entered the world for the first time. Mainly because I had lost all the defense mechanisms I learned as a man. I could no longer rely on my size in a potential problem situation or my intelligence to win a discussion. My best offense in the new world I wanted to be in was to plan ahead and do what ciswomen do, not get into the situation to begin with. As far as intelligence goes, just plan on losing yours if and when you encounter a serious discussion with a man.

As you walk up your gender path as a new trans woman, validation as a person becomes a valued piece of your new personality. In my case, I was never attractive or interested in men enough for them to be in my world, so my validation had to come where it had always come from in my life, from other women. When I see many of the transgender women bemoaning the fact they don’t have a man, I always say, don’t overlook having a woman love and validate you. Always leave your future options open because anything can change in your life when you are trying to cross the gender border.

Finally, “Mira”, try to develop a thick skin and learn from your possible presentation mistakes when you begin to go out. Especially today with many areas of society being so volatile when it comes to trans women and trans men. When you are a quick gender learner, your life can come together faster than you ever thought. Be prepared, it could be an interesting one. Stay safe and thanks again for the comment and I hope that I have answered most of your question.

 

 

 

 

Tuesday, June 23, 2026

I Wish I Knew Why

 

Image from Anderson Rian
on UnSplash.

It is not like I am new to being out in the world as my authentic feminine self, so I don’t know why I feel certain ways.

One of them happened this morning when I needed to take our car to the shop to get the oil changed before we take a rather lengthy trip to my old hometown later this week. As I have written before, I am still fearful of going by myself to any male dominated businesses.

I think it goes all the way back to when I was a kid when I used to go with my dad to an auto parts business a friend of his owned. There were never any women, and I felt totally out of place. At the time, I felt it was because I was young at the time and I would grow out of feeling self-conscious there. But now I think, it could have been my inner female rebelling at the ideas of being around all that intense masculinity.

Back to this morning, even though I did get an early start, I wanted to be there when they opened at 7:30 AM to get my paranoia over with. I was worried since we are headed into a holiday weekend, they would be busier than they were. Which was a moot point, since I had to figure out what I was going to wear, shave, put on my light makeup and head out the door. After doing all of that, I was still out the door by eight and still was able to get right into the oil change location.

Since I would not be getting out of the car for either of the places I could go ultra casual and wear my jeans along with my “Libra” themed burgundy tank top which I wear with my long hair pulled back so it softly falls over my shoulders which is my revenge for having to cut my hair extremely short when I was young and even later when I was in the Army. I am very fortunate in that I have never had any male pattern baldness, so I have always had a great head of hair.

It turns out all my paranoia was unfounded as none of the male workers did anything out of their way to make fun of me and were professional in every way. Before I knew it, I was on my way and breathing normally again. On my way to my nest stop at my wife’s Liz and I’s favorite coffee shop to pick up coffee and a light breakfast. Other than having coffee and food we like, the coffee shop also has a LGBTQA+ flag proudly on one of their walls. Again, the person who served me was very nice and put me at ease.

On the way home, during my short trip trying out the world again as an independent transgender woman, I was wondering if changing my estrogen HRT patches out today had anything to do with my moodiness about going out in the world alone. Friday, when I make a much longer trip back to my old hometown, Liz will be going with me as I must pick up more copies of my name change documents from all the way back to 2015.

Sadly, I have more negative memories of my hometown than good ones, but I need the legal copy with the judge’s signature on it for a life insurance policy I forgot so long ago. I can procrastinate with the best of them!

To make a small joke about my visit to have the oil changed this morning is that all my fluid levels turned out to be OK. Maybe the true win was to realize what the basic reason I still fear going into male dominated spaces so badly. It is a deep-seated problem which goes back to my youth which makes it very difficult to get rid of.

 

 

 

The Best Advice I Never Got

  Image from Frame Harriak on UnSplash.  The best advice I never got came from no one. There was no one there to tell me anything about wh...