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

Tuesday, April 7, 2026

Everything Was Fine Until It Wasn't

 

Image from Danny
Messina on UnSplash

Many times, when I was sailing along thoroughly enjoying my feminine self out in the world, I would come to a rude awakening that something was not right. As I experimented as a novice cross-dresser fresh out of the mirror at home, I learned any number of things could be wrong. Including the cruel imposter syndrome which haunted me. A great topic for another blog post.

Or maybe my makeup was not on point, and I looked like a clown in drag, or I had that old male scowl on my face instead of a pleasant little smile which gave away the fact I was not enjoying myself the way I should. But something was wrong as I was doing what I wanted to do for a change, and I needed to show it. Not revert to my old male ways of trying to scare people off before they even started to interact with me. It is something I work on to this day as it is easy for me to fall back into old gender habits. I needed to work hard to put my entire new feminine image into play when I was out or no matter how good my makeup and fashion looked, I was not going anywhere in my development as a transgender woman.

A quick example of the problems I was facing with my face happened one day when I was out shopping in a woman’s clothing store. When I came around a rack of clothes, I was startled by a young girl staring up at me. Worse yet, I was prepared for the worst when she took off looking for her mother. I was semi-relieved when I heard her say, look at the BIG woman, and I thought she had that part right. Until she said, the BIG MEAN woman, and I immediately felt bad that she thought I was mean. From that point forward, I put a slight feminine smile on my face as my final touch of makeup. Everything was right with the world that day (including the little girl who thought I was a woman) until it wasn’t.  Lesson learned.

Changing the way, I looked at the world with my face was just the beginning of improving my overall presentation in the world of ciswomen, young and old. Early on, I paid quite a few brutal dues when it came to encountering groups of teen girls in the malls I went to. We all were in the process of discovering our femininity, and the girls took their humor out on me vocally and it hurt but the process helped me to develop myself to a point where I could better blend in with the new world I was trying to conquer. I just had to learn to conquer in a different way than I had ever had to before. I could not just hope to bluster my way through life as a man which I had gotten used to, I needed to finesse my way through until I began to feel the benefits of female privilege past the occasional man who opened a door for me.

Everything was fine, until I learned I was just getting started on my dream to live a transfeminine future. I had no idea how complex a woman’s life could be with a passive aggressive future in store for me. Plus, a future where for a change, to survive with other women I needed to completely listen to what they were saying and make sure I looked them straight into the eye, so I did not miss any nonverbal communication which was coming my way. Several times, I was helped out of potentially dangerous situations with toxic men by paying close attention to the nonverbal cues being given to me by concerned women with much more experience than me.

For the most part, this time of my life, in my thirties and forties , everything was fine with the gender juggling act I was attempting until I pushed myself too hard, challenged my mental health and continually got in trouble with my second wife who caught me trying to sneak back into the house after a night of living as my newly thriving feminine self. At that point, massive fights occurred which ended with me trying to promise I would never go out again. Which I knew would never happen. Once I had seen the world from my vantage point of a trans woman, deep down I knew I could never go back to a completely male life. I think my wife knew that too and that is why the fights we had became so vicious. Particularly when she told me I made a terrible woman because (in my words) my gender workbook was not filled out, and I had not paid my dues. Which was exactly what I was doing when I went out to live. I was sad I couldn't share my new knowledge with her but it was just not meant to be before she suddenly passed away.

After she died, nothing was fine as I was intensely lonely and needed a shoulder to grieve on. I found that shoulder in a predictable place and she was there all the time, my transgender self. When failure was not an option in my life, all the lonely nights I spent exploring the world around me with other women proved to be an invaluable experience when I learned I did not “make” a terrible woman after all. It turned out, I did not “make” anything at all, I just found my way to a place I always should have been, and everything turned out of be fine and I could take the wasn’t away from it.

I was even happy for the first time in my life as the heavy expectations of a male life I wanted no part of were removed for good. Being free to be the true me was the best move I ever made and my only problem was I did not do it sooner. Everything was fine, it was just hidden from me by myself. When revealed, I was free to never look back.

 

 

Monday, April 6, 2026

What is THAT Sound?

 

Image from Jason Rosewell
on UnSplash. 

What’s that faint noise I hear far in the distance? It took me awhile to figure it out, but it was the sound of my feminine self-yearning to be set free to live. Very early on, I thought she would go away as I aged but the opposite turned out to be true. She grew stronger as the years of my life progressed.

That is when I started to realize just looking at my cross-dressed self in the mirror was just not going to be enough. I wanted more of the feminine life I had experienced. What I was experiencing was the idea of I had much more than a casual interest in women’s clothes and makeup. I was more into how they lived. The term transgender had not even been invented yet, so I had nothing to compare my feelings with. I did not think I was transsexual like Christine Jorgensen, but I was certainly different from other cross dressers I was seeing in my well-worn copies of “Tapestry” and “Transvestia” magazines. When all of that happened, the sound kept getting louder and something larger was wrong with me and it took me years to realize what was wrong with me was not what the sound was telling me.

I went on fighting myself searching for the truth I was looking for when it was right in front of me if I chose to see it. I ignored the advice of my handpicked gender therapist (one of the few I could find back in those days) who told me she could do nothing about me wanting to be a woman but could do something about my manic depression. Which I always had thought was something to do with my gender dysphoria. She told me it wasn’t and helped me by prescribing medications to help me in everyday life. At the time, it turned out, I was ready for help with my depression but not ready to face the facts about my gender future. I was used to loud sound from my days as a radio DJ and I was stubborn enough to want to hang on to a dual gendered life.

At the same time all of this was happening, I was beginning to explore the world as a novice transgender woman and learning every time I went out what the sound I was hearing really meant. I had life all backwards with my struggles to live a male life and the sound was telling me increasingly I was destined to be a woman all along. Not in the mold of having extensive major gender operations but doing it on my own schedule as I marched to my own drummer. Yet another sound which was growing in volume. Before I did though, I needed to undertake an extensive program of more exploration. I desperately did not want to make the move across the gender border at some point and find out I had made the biggest mistake of my life. My spouse, family and job meant so much to me, giving them up for no real reason scared me beyond belief.

Every time I began to have doubts about my upcoming gender decisions, my drumming sound grew louder as I felt more alive and natural when I was allowed behind the gender curtain with cisgender women. The work I was doing to prove myself to the world finally was paying off, for the most part. When I suffered a setback, I had the confidence and experience as a trans woman to do the right thing and move forward in my new life as I followed the sound of gender success. During this time, even though it is a blur to me now, I still remember that it all was not pleasant as I went through the turmoil of deciding which way I was going to turn next.

I know what you are thinking, what was she doing even thinking about turning her back on the gender future she had worked so hard to build. But I did as my male self stubbornly tried to drown out the sound my feminine life was making. Perhaps desperately would be a better term because of all the male privilege he had built up. He was desperate to hold off any more change.

Finally, the sound of change became deafening to the point where it could not be ignored anymore. I was not getting any younger and my transgender transition clock was ticking, loudly. As I had a huge heart to heart talk to myself, I came up with the decision to seek a doctor’s approval for HRT or gender affirming hormones as a natural progression of my feminine progress. In addition, I decided the hormones (if my body responded positively to them) would be the point of no return. I would have to come up with a different way to support myself financially, plus gather the courage to tell what was left of my family the truth about myself. As it turned out, the hormones began to feminize me faster than I ever thought possible and soon it became increasingly difficult to hide my protruding breasts, longer hair and softer skin than ever before. Long story short, my daughter accepted me and my brother rejected me as I revealed my life to them so I had the best of all worlds with the support of my daughter.

Ironically, one of the changes I went through was I had a greater, deeper appreciation of sound and music as a transfeminine person. I had gone full circle in my life understanding what that sound was and better, yet what it meant to me.

I always loved being right when it mattered most, and it did when I relaxed and listened to the sound of my gender spirit. I should give all the credit where credit is due…to the little sound inside of me who said keep trying when the going gets rough. Through the good times and the bad times, she was always there to help me survive.

 

Sunday, April 5, 2026

Facing my Deepest Fears

 

Image from Tonik on Unsplash. 

Over the decades I have found that my gender desires have produced the biggest fears and anxiety I have ever felt.

Prime examples came from the times I was first testing the world as a transgender woman. The number of occasions I needed to sit in my car making endless tries at adjusting my hair and makeup until I felt everything was right to attempt going into whatever venue I was going to. You would think from the number of times I had to face my fears; I would have at least become used to it. But I never did. In fact, I developed my own form of trans PTSD from the number of times I was rudely rejected by the public. I could not get it out of my mind that if I was laughed at once, I could be laughed at again. Which I discovered just was not true after I learned to dress for the public of ciswomen around me.

Finally, a little confidence began to creep in, and I did better for the most part, but it seemed the fear of being myself just would not go away. Maybe I can blame my old male self who in his own way was as strong willed as my feminine self and did not want to give up all the male privilege he worked so hard to earn. His reluctance to give up pointed to a deeper problem I had. The fear of facing myself. At the same time, my dreams of even trying to become a fulltime transgender woman in the world seemed to be a far-off dream.

What I decided to do then, even though I still was experiencing deep fears about my future, was experiment by going out into the world a little at a time. I started in what I perceived as safer spaces such as shopping malls and gay venues. If and when I was successful (or grew tired of) in those places, I would try more challenging places. Lessons I learned included money overcame gender problems in the malls and I was just considered another drag queen in the gay bars and made to feel completely out of place. I discovered to enjoy myself more I would need to try to frequent the same sports bar venues I went to as a man. Where I could drink draft beer and watch my favorite team on the big screen televisions. Sure, I was scared to do it as I knew how single women were viewed in sports bars, but I had to try.

Desire overcame fear and I was successful as long as I followed my three basics of smiling, never causing problems, and tipping well. Before I knew it, I was a regular and gained the backing of the bartenders who even saw to it that I had restroom privileges. Before  I knew it, I had built a small circle of lesbian friends who shared my love of sports, as well as another transwoman. Loneliness became a thing of the past for me, and my fear of being seen as a woman was going away too.

Just when my trans confidence was at an all time high, obstacles such as drunk guys would come along and ruin my evening. The night I remember the most was when a bunch of drunks noticed my trans friend and I at the bar and started playing “Dude Looks Like a Lady” time and time again until the manager asked us to leave. We did, temporarily, because a month later when I was in a nearby competing venue, I was surprised to see one of the bartenders who was there when I was asked to leave approaching me. I was astounded to learn the manager who had kicked me out had been fired for drug use and I was invited to come back. So much for the drunks who had played that song over and over and I had put my fears to rest. To this day though, when I hear that song, I cringe.

Sadly, even though I have been in the public’s eye as a transgender woman, I still look over my shoulder when I do things like use the restroom. Fortunately, I have Liz to help me out when I have to go and mainly these days, I don’t present as trans as much as I do as old and partially immobile. I am happy these days when I can find a restroom with a handicapped stall to take my fears away.

My deepest fears now revolve around the number of ridiculous restrictive anti-transgender bills currently in the Ohio legislature. One bill would make it illegal for anyone to wear makeup different than their birth gender. Which I guess would mean the orange felon or his sidekick Vance would be arrested if they come to Ohio. I am lucky that age and years of HRT have softened my facial lines to a point of where I don’t wear much makeup at all but what about the younger transgender population. Hopefully, none of this will actually happen or the courts will strike it down.

These days, I have managed at least to calm down my fears of what will happen to me if I have to go into assisted living or if I develop dementia like my dad had. I finally came to the conclusion not to worry about something I have no control over.

I don’t know why I waited so long to be paranoid over what has made my life worth living over the years and decades. I used to be a go with the flow type of person and if I got myself into some sort of a mess, I could get myself out of it. Probably now it is because I have to depend on my wife Liz for so much. Fortunately, most of my deepest fears came from pursuing my gender truth and when I came out to myself, I proved that I was the most important person of all to be truthful with. It was not until then did my life began to change for the better and I could live without all the fear I was experiencing.

 

 

 

 

Wednesday, April 1, 2026

Transgender Day of Visibility

 

JJ Hart doing trans outreach work. 

Transgender Day of Visibility was yesterday, and I did not post because I was out most of the day being visible.  Which was a change for me.

In the morning, I had several low impact visits to venues I feel secure in, so I did not feel any undo stress in going.  My first visit was to my local Veteran’s Administration Clinic to have my annual hearing check.  Even if my wife Liz perhaps may disagree, my hearing stayed the same and my next appointment was set for two years from now. From the VA, my next stop was at our bank where I needed to pick up a certified check. I was surprised when the bank was relatively busy and I needed to wait. Which is a problem with my mobility issues. Two very nice women helped me out by directing me to a chair saying they would guard my place in line if anyone else came in and tried to cut ahead of me. From there, it was clear sailing because the teller I went to was young and did her job very well and I was out the door before I knew it and there was no reason for anyone to question my gender. I was just a woman running errands as me. The best possible response I could have to my day of Transgender Visibility.

I knew my next stop would be easy because I was going to our favorite coffee shop to pick up a late breakfast and coffee of course. Over the space of time I have been going there, I have never had any problems with any of the staff concerning who I really was. The staff is always immersed in what they are doing to be concerned about me and even had a LGBTQ flag on their wall for a while when they had a decidedly non-binary manager in charge which was good to see.

My third and final interaction for the day came with a young woman who was a bath consultant at a company we were considering putting in a new walk-in shower to replace a dangerous (for me) old bathtub we had enough of. While we were in the small talk get acquainted part of the process, she asked what I did with my time since I was retired. I said, mainly I write a blog, and I am writing a book for my family to read after I am gone on my life. She was interested in what I blogged about. Then I broke my own rule, outed myself and said I write mainly about what goes on in a transgender person’s life. Of course, I needed to say I was transgender and today happened to be the Trans Day of Visibility, so here I was. Since the consultant was young and wanted to sell us something she did not react negatively to the idea I was transgender and married to Liz.

I came away from my own limited day of visibility hopefully thinking I had done my own small part to further the cause of transgender women everywhere to contradict all the negative publicity we get from the politicians. It is important to show the world we are just people like they are attempting to live our lives with no problems. Sadly, with my mobility problems, I cannot be as active as I once was in the community and go to public events like I used to.

Plus, more and more at the age of seventy-six, I am actively becoming me finally in life. It was like going through another major transition. I went from me being a cross dresser to accepting myself as a transgender woman, and now I am completing the circle and going back to me again. Only this time, with a big difference. I am the feminine being I was always meant to be. I was just fortunate to live long enough to live my circle. And celebrate another Transgender Day of Visibility.  And, if you are in the process of thinking of escaping your closet and having your own day. Celebrate those who are leading the way for you! Plus, on a positive note, the younger generations seem to be blinder to gender bias than the older ones, so all is not lost for the future you. Then, you can be involved with your own day of visibility and feel good about yourself.

 

 

Monday, March 30, 2026

Was I being Selfish?

 

Image from UnSplash and
Brooke Balentine.

When I was a maturing cross-dresser, one of my wives made it a prime point of her argument against my cross-dressing at the time saying that I was just being selfish. The problem I had with her saying that was deep down, I knew it was true. Mainly because I was spending all my spare time thinking about or doing my cross-dressing activities. I felt guilty, but there was little I could do about it as I wanted to be feminine so bad. So, I went on with my daily activities ignoring the best I could what she said.

Sadly, my selfish problem only became worse the farther along I traveled up my gender path. I simply wanted more from my life than what I was getting and I was pursuing it. I thought to hell with the risk I was doing to my male world and life as I knew it if my secret was discovered as it almost was several times. Like when I almost ran head on into my wife’s boss going to a big box store in a small Ohio town we lived in at the time. I did not think he recognized me, but he did bring up seeing a a particularly “big” woman the other day when he left work to pick up supplies at a party we were attending at his house one weekend. Of course, I could not let on it was me he was talking about, but my wife knew and questioned me about it later. I don’t think she ever believed my denials, but life went on until I made it to the next level of being selfish.

When I was out in the world as a successful transfeminine person, just doing it a little bit was just not enough. Success bred success, and if I could not for some reason make it out into the world again, I grew angry and bitter with life and tried to take it out on the world around me. By doing so, I even almost lost jobs because of my attitude. Having a sullen selfish attitude got to be so bad, I even sought out gender therapy to help me from one of the few therapists in Ohio at the time who dealt with it. It turned out to be that she could not work miracles with my gender issues, but she did with my attitude which was influenced by being diagnosed with a Bi-Polar depression disorder. Following a few experiments with medication, I found one that worked and my life became better. Except for I did not magically quit my feminine ideas and remained on my selfish path to see if I could ever live my dream of going full-time in life.

What made matters even more frustrating was, even with all the mental energy which was going into my transgender issues my male self was still able to advance in his life too. Making it harder for me to think about moving along with my plans and even being selfish about them at all. Through it all, my guilt was building about why I was even cursed with being transgender at all. This was before I finally began to understand my gender problems were not a curse at all.

In the meantime, my wife and I were clashing every time she caught me being selfish and leaving the house as my feminine trans woman self. One time she was even mad enough to tell me why I wasn’t man enough to be a woman. If I was smart at the time, I would have listened to her advice. I should have faced my true self and started making plans for my ultimate male to female femininization project. I just was not ready for several reasons such I loved my wife very much and the life we had built together.

By now, you have probably noticed a theme here. I kept shooting myself in the foot by being supremely selfish when I set out to build a new life when I already had a perfectly good one with a loyal wife, good job and loving family. All of which helped to describe why I felt so much stress and tension during this portion of my life. All the therapy and medications in the world could not help me until I had the courage to face up to my true self as she looked at me in the mirror. She had been there all along, and I thought I needed to apply makeup to bring her out (which I did for the public) but one on one, she was very real to me. She appreciated all the outwardly things any ciswoman needs to survive but inwardly, she just needed to be recognized for the person she had the potential to become.

Ultimately, I outlived my second wife (and many family members and friends) which freed me up to not feel any selfishness at all about what I was doing with my femininization. I was just busy preparing my world for the truth I had so deeply known. I should have never been a male at all and was just a woman cross dressing as a man. Needless to say, it was an enlightening experience coming out of my gender shell and having the opportunity to live my feminine truth. Just having the chance to compete in a world of ciswomen on their level was an intimidating yet exciting experience which my true self was up to. After living life hidden away all so many years against her will. As with most all transgender women and transgender men, it is a major project to bring ourselves into the world and unfortunately, we must be selfish to do it. The good thing is, once we go through the selfish part of our lives, we have the potential to be good, loving partners. If we are destined to find that special someone to love.

Life dictates it is nothing but a circle, and we have to take the good with the bad. Selfish or not.

 

 

 

 

 

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.

 

 

 

Everything Was Fine Until It Wasn't

  Image from Danny Messina on UnSplash Many times, when I was sailing along thoroughly enjoying my feminine self out in the world, I would c...