Showing posts with label transgender women. Show all posts
Showing posts with label transgender women. Show all posts

Saturday, May 2, 2026

The Last Line of Defense

 

Image from Gayatri Malthroa 
on UnSplash.

Throughout nearly half of a century, my male self-fought the complete transition I made into a feminine lifestyle.

During that extended period of time, I think I tried everything possible to convince myself that I was wrong to want to play in the girls’ sandbox at all. As I mentioned in yesterday’s post, I “purged” many times of my feminine belongings. Leaving me with nothing but my most cherished pieces of girl’s/woman’s clothing and makeup. The makeup was easy because I knew I could always buy more. Perhaps the most precious items I never threw away were the nice wigs I was able to buy and the silicone breast forms which ironically were given to me by a fellow cross dresser who was purging also. Deep down inside, I knew I would need the wigs and breast forms again when my urge to cross-dress returned. As my own personal history told me it would.

It turned out that purging was not my last defense, no matter how hard I tried. In fact, the more I tried not to be feminine in any way shape or form, it seemed I slipped closer and closer to it. Especially when I learned I could dress to blend with most of the ciswomen around me. It was then I learned how natural I felt when I began to get it right and could feel all the gender euphoria I could feel.

What I did continually feel was my masculinity slipping away and I only used it on occasions with my wife in mixed company and when I was working in a high-pressure environment. For years, when I was out in the world experimenting living a new life, I felt as if I was sliding down a steep hill towards a transgender cliff which I had no idea of how I would be able to land.

In all fairness to my second wife, she never opposed me cross-dressing and knew about it when we got married. But on the other hand, completely opposed any idea of me becoming a transfeminine person. Between her and my male self, they made formidable opponents in my life when I thought about living as a trans woman. What made it all worse was when my wife kept saying she did not want to live with another woman and did not agree to that when we got married and I had to agree with her. Putting me in a very difficult situation in my life. I escaped the best I could by sneaking out of the house behind her back at any given time I found to test the world time and again to see if I would be allowed to go back behind the gender curtain. Which in many ways, represented escaping the last defense to staying in the male world I had.

Of course, my wife found out on numerous occasions what I was doing as a trans woman and resisted all my progress. When she did, we had giant battles which she normally won and I tried the therapy route to help me with my gender issues. Therapy helped me in many ways in my life but not so much with my deep-seated gender issues. I was expecting too much when one therapist told me if I thought our sessions would ever relieve my tensions, I would be wrong until I was able to make the final decision on if I was able to be a woman or not. At that point, I had two of the most far-reaching quotes that I ignored which were told to me. One of which was the time I was told I was the only one who could decide my gender future and the second was when my wife told me to go ahead and be man enough to be a woman. I was so sure I could do it my way and it cost me dearly. Especially, in terms of my overall mental health when juggling two genders and two lives at once became too much to handle. I did not know if I was coming or going on which day it was on how I was expected to act.

As many of you know, my second wife tragically died of a massive heart attack, leaving me with only my male self to do gender battle with. His last defenses deteriorated quickly as I became deeply unhappy and lonely and took solace in my inner female self for comfort. She stepped up big time, and very soon when I was not working nights, I was in one of my regular drinking venues seeking company. That was when I discovered I had more in common with the lesbians I met than with any man. Since most of them rejected me anyhow for leaving the good old boys club. I was able to say good riddance and go forward in my life into a world I never thought possible could ever be a part of. I had never really got along well with men in my life, and it turned out nothing had really changed. Except the way I was exploring the world. Finally, as my true self. As I was finding me after all those years of searching.

The last defense my male self-had was when my third wife Liz and only daughter came to my rescue with unwavering support for my final dive off the steep gender cliff. They made the landing very soft, and even easy. More precisely, Liz made me a believer in myself again and my daughter gave me support I needed from what blood family I had left since my brother rejected me, and my parents had long since passed away. Add in the couple of lesbians I always socialized with and I had all the support I needed to succeed in where I had dreamed of going and being accepted behind the gender curtain.

By far, I would be remiss if I did not mention the power of HRT or gender affirming hormones in removing any of the final defenses my male self-had going for him. I could not believe how fast the hormones acted as my body began to change, inside and out. It would take a whole post to describe all the impacts the hormones made to me. In fact, I have my annual appointment with my endocrinologist coming up this week, and with it, the chance to get refills on my hormonal patches.

Maybe I can thank her then for helping me to win my battle with my male self. Since I receive my HRT meds through the Veterans Administration, I always hope nothing changes from the top down with my ability to keep receiving a huge part of what makes me whole. I worked too long to get here.

Thanks again for joining me on my journey and I hope my experiences help you too.

Any comments, claps or subscriptions are welcome and make my work so worthwhile!

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Wednesday, April 29, 2026

Connecting the Gender Dots

 

Image from Beya Yurtzkuran'
on UnSplash. 

Connecting all the dots in a life when you have gender issues is never easy.

Especially so when your life’s workbook is completely blank and you have nowhere to go but to struggle. The great majority of transgender women and transgender men grew up with unapproving parents and/or no peer group pressure to shape our gender youth and help us along. At the best, the closest dots we were trying to connect were fuzzy and far away.

On the other hand, with me, my male dots were always crystal clear and easy to at least try to connect. If I was successful on a sports team, I would connect an easy dot is a great example. But if I was cross-dressing as a girl in front of the mirror, I was always confused on how I should act or feel. The only certainty I had was I knew I wanted to feel pretty.

As I progressed through life’s lessons, I learned the impact of achieving the connecting of my feminine dots while at the same time, leaving my male ones behind. Sacrifice became the ultimate name of the game. Especially when my second (out of three wives) kept calling me selfish for my complete pursuit to begin to leave my male past behind and live as a complete transfeminine person. What made matters worse was the fact that my gender dots on both sides of the spectrum were becoming clearer. I was becoming more successful as a father and as a provider as I advanced in my chosen profession, but at the same time, I became better and better at presenting myself as a convincing woman. For the longest time, my dots formed a parallel path. Heading ultimately for a collision.

I was stubborn and tried to separate the dots I was connecting until it affected my mental health so badly I could do it no longer. I was like a juggler trying to balance the two main binary genders as fast as I could and it nearly cost me my life. I was finding it harder than ever to separate my old unwanted male self from my new exciting yet terrifying new feminine self when one side began to bleed into the other. For example, when I was in a company meeting full of men, I would daydream how it would be if I was there as the only woman. Before reality would slap me down and back into the present.

Finally, I could take it no longer, and I began to give up on connecting any more of my male dots at all. I figured if I connected any more dots, it would just create more baggage I would have to deal with when I male to female transitioned. Mentally, I began to make contingency plans on what to do when I could ever connect my female dots and live out my dream. It is when I began to kick my experimentation portion of my life into high gear. I wanted to make certain as little as possible would be standing in my way as I moved forward in life. I needed to deal with the possibility I would lose contact with my wife and family then figure out what I would do to support myself financially. I was fortunate when my daughter stuck around to support me when my only remaining blood relative (brother) did not and I was old enough to support myself on an early social security retirement I earned and selling collectables my second wife who tragically passed away, and I collected over the years. So, I had connected all my obvious dots fairly well.

From there, the most challenging aspect of life I needed to face was the actual one on one daily living a trans woman has to take on. Learning the lessons a ciswoman is raised to know as she transitions from a female to a woman. Such as the shifting from white male privileges to the female privileges that I had only had the chance to dream about and not know because I had never been allowed behind the gender curtain. Once I was allowed behind the curtain, many aspects I never fully realized ciswomen actually go through became a reality to me. I was connecting my dots and maturing into the transgender woman I always dreamed of becoming. All my misconceptions about just achieving the appearance aspect of femininization faded away as I learned there was so much more to me than just trying my best to have an attractive face. It was quite the shallow existence for me as I needed to develop myself into a quality new human being that the world reacted to on a everyday basis.

As it turned out, HRT or gender affirming hormones took final care of the attractive part of my being as I went from being attractive to being the real me. Because the hormones softened my skin and facial lines and helped me to grow breasts, hips and hair. Like I said, all of which were the real me just waiting all this time for the changes to happen.

All the dots I connected were in a big circle. I went from a young boy for the first time being amazed at what he saw in the mirror (and wondering what was next), all the way to being able years later to being able to find the real me and live out my goal of crossing the gender border into a transfeminine world. I could not wait to give away all my male clothes; enjoy the new hormones I was on and live a new life. I was even able to take vacations with my third wife Liz to places I had never been before. All as my new self.

I can’t say connecting all my dots was ever fun and at times very scary, but they were always with me as I lived my life. At my advanced age of seventy-six, I am fortunate that I had the chance to find the real me before it was time for me to connect the final dot and step into the next dimension.

 

 

 

 

 

 

 

Sunday, April 26, 2026

My Life's Passion

JJ Hart on vacation
last winter. 
Without a doubt, the one passion which has consumed my life the most has been my desire to be a woman.

I continually write about my youth as a confused boy wondering if I was the only boy in the world who wanted to be a girl. My desires extended all the way to what I wanted for Christmas (the doll baby I never got) all the way to when I lied about what I wanted to be when I grew up. Rather than rock the boat I always said some sort of a male profession such as a doctor or a lawyer rather than what I really wanted to be, a woman.

All I could do was take refuge in my mirror which told me I made a pretty girl out of the boy I was at the time. It became a passion for me to use as much of my free time as possible to cross-dress. At the same time, I became really good at acting like a boy by playing sports and having an interest in cars. I was so good, it kept the bullies away until male puberty invaded my body. Outside of hating the changes puberty was making to my body, I remember being intensely aware of my new masculinity and what to do with it. Even walking like a man was a chore for me to learn to do. I was so afraid of walking like a “sissy” and be made fun of by the bullies that I feared what to do. Little did I know that later in life my passion would be to unlearn all that I needed to learn at the time about being masculine.

As much as I tried and as tormented, I because of my gender passions, I could not seem to lose my desire to be feminine over my hated male image. At the time, I was in the midst of what I call the information “dark ages” before the internet and any social media input. Even the word transvestite was new to me as I struggled to find my footing in life. In other words, my gender closet was very dark and lonely, with little opportunity to have any future at all in my passion to understand and be feminine.

I stayed that way until I grew older and my passion included receiving my cherished issues of “Transvestia” magazine and I could read the “wisdom” of “Virginia Prince” whenever I could get my hands on another issue. For a while I thought it was working until I began to read about the social mixers certain chapters had to meet and greet other cross-dressers or transsexuals as they were known back in those days. Amazingly, one of the chapters in my native Ohio held mixers on a fairly regular basis that I could attend. I thought for sure, meeting others with similar gender issues could help me but I was wrong. Their passions exposed the many layers of where I could fit in (or not) with the remainder of the cross-dressing community and at the least, I hoped I could come away from the social by making a friend or two.

The only thing that really came out of the mixers was the knowledge that another chapter was coming close to establishing their own socials in Columbus, Ohio which was vastly closer for me to attend. Maybe I was too standoffish or even shy to make what I would call friends, but I continued to keep going any way and even was rewarded with invitations to smaller more diverse parties in Columbus which did not have to supposedly adhere to all of “Virginia Prince’s” archaic rules such as admitting heterosexual members only. As I said, the parties I went to were very diverse from lesbians to cross dresser admirers all the way to transgender women getting ready for gender realignment surgeries. The learning process I went through every time I went fueled my passion to learn more about my place in this new exciting world, I was becoming a part of. I could not wait to be invited to the next party.

I felt so secure from my party experiences, that I decided to do more exploring in my own in public. That is when I began to seek out the straight venues I used to go to as a man when I always wondered what it would be like to experience them as a woman. My passion for my new life exploded when I discovered I could be accepted which kept me out of the gay venues which I did not feel comfortable in at all. I was able to go out to be alone and mostly socialize by myself for the most part as I worked hard on my passion to fill out my gender workbook which was seriously lagging behind my fast-paced life as a novice transgender woman.

By this time, I had decided I had made the right decision to follow my feminine passion and try to survive in a world run by ciswomen. My path felt natural and I was rapidly coming close to the time when I was going to push all my male privileges I had earned to the middle of the table and bet my life on the transfeminine path I was on. I could not believe that my entire life’s dream/goal was suddenly within my grasp. If only I had the courage to finally follow through on my passion.

I did follow through and with the help of my future wife Liz, I went on HRT, threw out or gave away all my male clothes and never looked back on my male life except to decide which baggage to bring with me. I even went as far as taking female vocal lessons to try to teach me all important feminine communication skills which I desperately needed. It all turned out to be a labor of love as I listened and learned from the world around me.

The boy so long ago in the mirror finally had his deep-seated passions rewarded.

 

 

 

  


Saturday, April 25, 2026

Burning my Gender Bridges

 

Image from Kellen Riggin 
on UnSplash. 

Sadly, following  my gender path included burning many bridges behind me which connected me to my old male past.

I think the problem stemmed from the self-destructive behavior I always exhibited when I did anything remotely successful as a man. I still had not yet faced the fact that I wanted nothing to do with being a guy, and everything that came with it. Including the potential of living with the white male privilege that was an automatic addition to my life.

Then, there was always the part of relief if I was ever caught cross-dressing early in life. Finally, I would be exposed as the deeply feminine person I really was. Life was much simpler back in those days, and I wondered how bad it would be to go to a psychiatrist and try to explain to him or her how I was not mentally ill; I just wanted to be a girl and my ultimate goal in life was to grow into a woman someday. The only way to get there was to risk everything and not get caught, but I never did and did not have to burn any bridges to find my way into early forms of conversion therapy.

It was not until much later in life did, I really began to torch my bridges behind me. The problem was, I needed to build my bridges longer and stronger to carry all the increased male baggage I had accumulated. Most of which was against my will. This was when my male life was outpacing my female life and I was building a small family and a very good job while at the same time managing to hang on to a long-term marriage where my wife was learning about and fighting against any thoughts of me sliding towards leading a transgender lifestyle. I desperately did not want her to be on any bridge that I burnt, and the pressure built on me not to light the match on my life if I took the huge step and decided to keep femininizing myself.

As I reached deeper and deeper into myself looking for an answer, I felt increasingly natural when I was attempting to put together my feminine self. No matter how risky burning my previous gender bridges behind was, I could not shake the idea I was doing something right by transitioning my old male life away.

The next big problem I faced was letting the world I was in know I was switching from my male club membership to the girls’ club. As I was being increasingly successful in carving out a new secret life as a trans woman, I did not want it to be secret any longer. So, I did the natural thing for me, I tried to make it impossible for me to turn back on my gender path. I started to go into my own restaurant dressed as me to see if I was recognized which I quickly was. I could have lost my executive general manager’s job immediately if I was but I was prepared to burn that bridge when I came to it. Looking back, it was not the smartest decision I ever made in my life but one I was desperate to make as my female self was crying out for attention.

When I progressed to a certain point in my male to female transition plan, burning bridges became just an automatic part of the plan because I did not need the male part of my life anymore, I was getting rid of. The prime example as I always point to is the night that something had changed in my thinking that I was not cross-dressing to go out and socialize, I was finally trying to formally join the world as a full-fledged transfeminine participant. The evening was a resounding success, and I knew from that point forward that I could never go back to being a man again. I could see my bridge burning over a not-so-distant horizon and it actually was scary and good at the same time.

I probably would have burnt more bridges earlier in my life if it was not for my second wife and my male self who was hanging on for dear life but still refusing to give up his hold on me. They put up a formidable fight to the point of putting out the fires I started on purpose. It lasted until my wife passed away, leaving only my weakened male self to fight me.

The final bridge to burn was when I was approved for HRT or gender affirming hormones. It was an all hands-on deck torching when my external and even internal body began to change. My sudden change in skin tone, slightly protruding breasts and longer hair which I refused to cut gave my external transition away and the part no one saw, but I felt, such as my emotional growth made itself known to me.

Following years of gender turmoil and change, having nothing in my way felt very good and I loved the hormonal changes I was going through with my new wife Liz. Which was well over a decade now. As I said, burning bridges in my life was always a scary idea but one I needed to do to get to where I wanted to go as a transgender woman surviving in the world of ciswomen everywhere.

I was fortunate in that I did not get burned as much as I did along the way in the process. I must have been quicker than I thought as my trans destiny showed me the way during the darkest nights. Who knows? Being caught on one of my bridges may have been for the best when I needed to work my way out of danger, but it never came to that with me. I became quite good at burning my bridges…or lucky.

Thanks to all of you who have taken the time to comment, clap or subscribe and just read along with me.

Without you, it means nothing!

 

 

 

 

Saturday, April 18, 2026

The First Time

 

Image from Jon Tyson 
on UnSplash.


Like most of you, as I look back at an increasingly long life, I tend to remember many firsts I accomplished.

Of course, my gender dealings are among the top things I remember along with the first time I had sex with a girl, all the way to the first time I drove a car. I also vividly remember the first prom date I went on and how amazed I was when on the first night of basic training in the Army how many of the men around me were crying. I may have felt like crying too because the military was taking away my makeup, dresses, and wigs but I would be damned if I would cry in public about it.

Through it all, I learned the hard way to wait out the hard times and try to look ahead and not behind me for a better future. The first time I remember it happened was when we were on a long-forced march during the wintertime at Ft. Knox, Kentucky. I was feeling sorry for myself until I looked back and looked at how far I had come. From it I learned a lifetime lesson I could fall back on when I was feeling down. Which was often when I could not have any way to express myself as a feminine person by cross-dressing.

I had no idea when I resumed my civilian life after the Army how much I would have changed when I had the freedom to explore who I was. Even to the point of trying to come out to my mom. I was naïve and thought that even though I was accepted when I came out to anyone for the first time about being a transvestite (as we were called back then) while I was still in the Army, my mom would accept me also. I was wrong and all she offered was a trip to a psychiatrist rather than any understanding. So, my first time coming out to any of my family was a complete failure and the subject was never brought up again. I went back into my gender closet and slammed the door shut again. The only redeeming value I had was my closet was big enough to have a mirror to lie to me about my cross-dressing future when I needed it.

The first time I made a major step into the world as a future transgender woman was when I started to go to Halloween parties where I could express my true self. After a rocky beginning, I settled into a professional woman’s “costume” which brought me acceptance and gave me hope that possibly I could make it to make dream of living fulltime as a transfeminine person if I looked ahead and learned from my experiences.

From those humble Halloween beginnings, I began to explore a number of other firsts on my gender path. I figured if strangers were mistaking me for a woman at the parties I was going to, I would not have to wait another year to do it again and started to visit venues such as clothing stores in big malls as well as safe places such as coffee shops and bookstores. When that worked for me, I expanded my gender outreach into more challenging venues such as restaurants where I needed to interact with more people.

As I began to enjoy my time as a novice trans woman more and more, the problems of how much male baggage I still had began to cause a strain with my mental health which was already fragile. All my male life, I had tried to fight a losing battle to get rid of any possible positive male belongings that I had by moving all around to different jobs and being very self-destructive. Like runaway trains on the same track, the successes I could not wish away were coming at me from the male and female side. I could not shake the fact I had a very successful marriage, a good daughter and great job I had worked hard for so easily as I had imagined. It was the first time in my life I felt bad about being successful.

At the same time all of this was happening, I realized I was transitioning again as my transwoman self. It happened when I grew tired (again) of thinking of myself as a man who was just cross-dressing as a woman into more of a woman myself. It seemed I was facing firsts every week when I snuck out of the house to be myself. I was terrified and excited at the same time with the way my life was unfolding. I had never planned on how my life was turning out, even though I hoped that it would. I never dreamed I could carve out a new life as a transgender woman as quickly as I did.

Now I could look back on all the other first times I could remember as being important and add my series of transitions as a male to female feminized person with them. My first stable communications with other women one on one immediately come to mind as firsts. It was because I was allowed behind the gender curtain in a way I never was when I was acting to be a man. Plus, I can never leave out the impact HRT or gender affirming hormones had on my life. All of a sudden, my inside feelings and external images began to sync up, and my world softened on the hormones. Making many of my previous firsts in life seem minor in comparison. Who cares about marching at Ft. Knox when I could feel so good about myself. Truthfully though, one first led to another and made my life much fuller as I look back on it.

I never realized all the firsts were just a sign of where destiny was leading me in my life and I should have paid more attention when all I wanted to do as a kid was to be a woman when I grew up. I was always a go with the flow as a person, and the flow took me eventually exactly where I wanted to go as a transgender woman…with a lot of help from my friends.

 

 

 

Thursday, April 16, 2026

We Must Be Better

 

Image from Ecaterina 
on UnSplash


Yesterday I wrote a very short post about going to the doctor with my wife Liz. During the post, I put quite a bit of emphasis on what I was wearing, just to look casual. Following the post, I received a comment from “Dana” exploring her own feelings about presenting in the world convincingly as an older transgender woman. She said (and I paraphrase) we older trans women must be better than the average ciswoman to survive in the world.

Of course, I agreed and took it a step further. Young and old, in no matter what we do, transgender women and transgender men must be better than their cis counterparts in everything they do.

It all started with me when I began to seriously get out of the mirror as a novice crossdresser and into the world. One of the first things I needed to do was upgrade my very limited fashion wardrobe. I found out the hard way; I was too heavy to attempt to find fashionable clothes for larger women like me. Immediately, I went on a diet which melted off nearly fifty pounds of weight. Which made all the difference in the world for my shopping confidence when I haunted the thrift stores for the best clothing bargains I could afford on my still limited budget.

At the same time, I concentrated on taking care of my skin by using cleansers and moisturizers every morning after I shaved. My skin did improve and I could use less makeup for a better overall effect. Through it all, I considered it a labor of love if I was ever going to present better in the world as a trans woman and not be mocked.

Finally, I did make it to a point where I could blend in with the ciswomen around me after learning many brutal lessons which sent me quickly home in tears. I found out the hard way I had to be better, just to be average and blend in with the world which was seemingly out to get me. Probably the main thing I had going for me was how dedicated I was to be staying on the gender path I was following. I always knew it was going to be rough but not as tough as it was turning out. I had a lot of dues yet to pay if I was ever going to make it to my dream of living as a transfeminine person. I thought I knew a significant amount of how women live but I had no idea of the complexity of life I was facing. Which was exactly what my second wife was trying to tell me every time she sensed me drifting away from being a cross-dresser towards starting HRT and living as a transgender woman.

What she did not tell me was, in order for me to make it, not only would I have to be average as the new person I was exploring being, I needed to be better. I was fortunate and stuck to my ideas of exploring the world around me as a trans woman mainly because I little voice in my head kept telling me I was doing the right thing because I felt so natural when I was living it. I emerged from this time in my life with a few scars from the experiences I was going through which healed quickly as I moved on to better things.

In essence, I found I could be better and carve out a new feminine life from scratch. A place where no one knew anything about my old male life and my present seemed to be more positive than my past ever was. In my way though I still had the usual male baggage problems such as an unapproving spouse (whom I did not blame), a family, and a very good job I knew I was going to lose if I did what I knew deep down I would have to do. Jump the male to female gender borders and finally live where I wanted to live from the beginning.

At the same time, I found the more complex my life became as a trans woman, the better I needed to become to protect it. On the girl’s nights out, I was invited to for example, it was key that I never went into my past very far and outed my deeply rooted male past. The example included the time I spent with my lesbian friends who would have not enjoyed any stories I had of my male past if I ever let my guard down and just blurred relevant details of my past. My willpower kept me going until I never thought about my past at all, except that it was a bad dream.

If you are on the fence considering coming out into the world as yourself, just remember to build yourself up to the point where you are the better person as a transgender woman. Perhaps then, you will have reached a place you were never able to find in your old unwanted male life. And key to the whole process is when you are feeling natural as your feminine self. By then, you will know that you have made it to a good place on your gender path. But if you decide not to go any farther, that is OK too. It is your life to live to its fullest, and your journeys into the feminine gender will have taught you so much about the need to be better.

I get asked all the time how I knew about my gender issues, and the simple answer is I always knew and refused to do anything significant about it. I was stuck in my male box from birth, and he was a powerful influence on me until I knew once and for all the only future for me was as a trans woman. Somehow, I just knew the truth about myself and quit fighting it. It was all for the better.

 

 

Saturday, April 11, 2026

Your Gender Path maybe Different Than Mine

Image from Erik Mclean
on UnSplash. 
 

Even though many of us share similar paths to our dreams of becoming successful transgender women or transgender men, often our paths diverge and we end up going different directions.

Most of us start out on our own without the help
of an understanding sister or mother and must fill out our gender workbooks as we go along. There is no one to tell us what to wear or how to act in our younger years as a cross-dresser. We just know we have conflicting ideas on what we are doing. On one hand, we cannot wait to put on the pretty dresses we found that still fit us, but on the other hand, we felt guilty doing it. It was somehow taking away what was left of our fragile masculinity.

At that point, most of us were willing to sacrifice that masculinity for the intensely intoxicating appeal of looking at ourselves as pretty girls, especially before puberty got ahold of us and testosterone poisoning set in. We all know what happened then, our bodies grew angles instead of the curves we admired on the girls around us and life would never be the same again. From that point forward, many of our paths seem to diverge. Over the years, I have heard from several readers who put down their urges to be feminine with no problems until much later in life. While others followed a more focused stairstep path which meant meeting and learning from other cross-dressers or transgender women searching for their true meaning to life. I know when I first discovered there were others like me who shared gender issues and I could go meet them; there were many layers of people who attended the socials. Anyone from cigar smoking men in dresses still going overboard to preserve their masculinity to completely femininized transsexual women whose next stop was gender surgeries.

It was then that I began to see and appreciate the different layers of the gender community I was seeing in person for the first time. I could almost compare it to the amazing number of cosmetics I saw the first time I went shopping with my own money to buy my own. The entire idea of going to a mixer of my peers did not work for me at all. I became more confused about where I fit in on the gender spectrum than when I started. I knew I was much more than a part-time cross-dresser but was not committed enough to consider complicated and expensive gender realignment surgeries which were still fairly rare back in those days. The direction I decided to take was one of experimentation which I found set me apart from many of the other gender conflicted individuals I had met.

I certainly would not recommend the direction I took because it involved a certain amount of risk and way too much alcohol in the mostly gay venues I initially was going to. What happened was, I used the fake courage of the alcohol to allow me to take ill advised chances in places I should not have been as a single woman. Especially a transgender one. I was fortunate when I escaped unharmed in a couple of situations I should have never found myself in as I was dressed way to provocatively for where I was going and one time in particular found myself having to be bailed out by my second wife who had warned me ahead of time about my mini-dress being way to short. I attracted the unwanted attention of a cross-dresser admirer who was huge and had me trapped in a small hallway with nowhere to go when my wife grew curious and came in time to rescue me. Believe me, it took me a long time to live that incident down with her.

Even when I became a regular in the big public straight sports bars I was going to, I would not recommend my methods of establishing a path to gender freedom as a trans woman. Being a single woman in a public place can sometimes be dangerous to the point where you don’t see many ciswomen do it. They always bring a friend or two for safety which it took me awhile to finally come to the point where I could do it too. My only recommendation is to act like you have a friend coming to join you by acting as if you are talking to them on a cell phone, or “save” a seat next to you with your coat if it is wintertime. Better yet, you can solve the problem completely by sitting at a dining room table, but what fun is that?

Another way to attempt to find companionship is through the use of social media. I tried that too and had to sort through a tremendous amount of trash before I hit the jackpot with the person who turned out to be my third wife Liz. Unbelievably, she contacted me on a social media site which I was listing under woman seeking woman. Better yet, it turned out we were within driving distance of each other and began to correspond until I became brave enough to talk to her on the phone. I was so ashamed of my voice to do it. I finally jumped off the deep end and had success as we started to date. That was over twelve years ago and we married and are going strong I am happy to say.

I see and hear from so many transgender curious people who are on the gender edge in their life with no evident way out. My only recommendation is that at some point you need to take chances if you ever want answers in your life. The only certainty is if you do nothing, nothing will happen. I’m sure I don’t have to tell you that you do have to be careful though with all the scammers out there these days and all the negative people you may encounter if you decide to go public. With the political arena and anti-transgender laws which are being passed in many states such as my native Ohio.

No path is right and who is to say, your path is not right for you even if you decide to stay in your closet which is safe and not risk giving up things such as spouse, family, friends and employment. Maybe you can experiment too as you discover which path is right for you. As I said, be careful of the stop signs and bumps ahead.

 

 

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.

 

Saturday, April 4, 2026

Easter Envy

 

Image from Annie Spratt
on UnSplash. 

Once again, it is Easter and time for some ciswomen to model their new colorful, feminine dresses and accessories to the world.

Like most of you, I remember the envy I felt when once again I needed to be forced into a restrictive suit and tie for one of the rare occasions we went to church. Why couldn’t I be one of the girls in their Easter finery. All the envy in the world I felt did me no good as off to church we went. My parents thought I just did not want to go to church (which I didn’t) but did not realize the real reason. I was just jealous of the girls.

Back in those days, I had very little inkling of how my desire to look like the other girls ran much deeper than I ever thought it would. I was scratching the surface of where I would end up in life as a fulltime transgender woman. I thought it was an innocent hobby that perhaps some day I would grow out of when the opposite happened. I grew into it. If I had any idea of all the growing pains I would feel over the years as I grew into my true self, I don’t know if I would ever undertake the gender path I did.

The truth of the matter is that I did not think I had any choice. I was born into an unforgiving male world that I was expected to excel at. I knew too that if my cross-dressing or gender secret was uncovered, I would be sent to a psychiatrist and told I was mentally ill. I did not know exactly what was going on with me, but I knew I was not mentally ill for just wanting to be feminine. On the other hand, I knew my WWII/Depression era parents would have any idea of what was going on with their eldest son to take any creative measures to help. The first measure would be acceptance. In my wildest dreams, did I ever think they would buy me a pretty new dress for Easter and do away with my suit and tie forever. My parents were simply not built that way so that they could step out of their rigid parenting box to help me. I was stuck in a male world until I could figure a way out on my own.

Over the years, regardless of setbacks such as military service, I was fairly successful in my male life. Which ironically made it harder for me to give it all up and cross the gender border when the time came. One thing I never lost was the envy I felt for all ciswomen who inherited from birth what I wanted so bad. I kept remembering the girls and women in their Easter dresses, even though I rarely wore a dress as I attempted to blend into the world as a woman. It seemed fashion had gone away from the frilly feminine basics once I arrived at the point where I could take advantage of the new world I was in. For years what I did take advantage of was the fashion trend where I could wear oversized sweaters with miniskirts, flats and opaque tights. Sadly, fashion moved on, and I needed to also if I was still going to blend in with the world as a transgender woman. Not only did I have to try to equal the cis women I was around, I needed to be better. So, I went with denim mini’s with long flowing tops to attempt to hide my oversized male torso.

Even with all the effort I was putting in, it never seemed to be enough to compensate myself for not being the pretty girl in her new dress at Easter. Ironically, then I found out from my wife Liz how she was a tomboy and did not like all the frilly Easter fashion she had to wear and was always under inspection from her mom on getting her new white tights dirty. I learned the view of the other gender side was not always the better one. It left the door open for a greater understanding of what females go through to be socialized into women and why some never make it.

This Easter, if you are religious, I hope you have the opportunity to celebrate the true message of the day and you don’t get hung up on what the ciswomen and girls around you are wearing. Although, I don’t see many women getting all dressed up for any reason anymore. Maybe if I attended any sort of church services at all, I would.

At any rate, celebrate Easter in your world the best you can!

 

 

 

 

 

Thursday, April 2, 2026

Gender Lost and Found

 

Image from Ewoud Van Der
Brandon on UnSplash. 

On occasion, I think you must hit rock bottom in your male life before you can begin to build a new feminine one. I equate it to my own transgender lost and found in my life. Before I get into what I found when I started my path to my dreams, I decided I had to have a basic knowledge of where I wanted to go.

Seeing as how I was born into the pre-internet times when information came in magazines arriving in the mail, I was stuck in the “Transvestia” world of Virginia Prince if I wanted any information at all about transvestites or cross dressers, as Virginia called us and oh yes, we had to be heterosexual to join. Through it all, I was intrigued by the pictures of attractive men dressed as women, as well as the entire world of mixers you could go to. If you happened to live close enough to one to go which I did. Ironically, the mixers I attended did not do me much good because the only mixing which happened involved my brain when it was all over. Often, I left more confused about where I wanted to be with my gender struggles than when I started.

None of my searching was helping much and my attitude about myself was sinking to an all-time low. I felt lost and forsaken in my life and felt sorry for myself because I was the one who wanted to do away with being male and assume a feminine existence. It took me a while, but I finally backed off from being a victim and my ideas of whom I really was started to improve. I had hit rock bottom and was beginning to improve, which helped primarily my fragile mental health. My goal was to close my transgender lost and found department for good.

Sadly, I was a little ahead of my time to closing my department because I still had so much more to learn about existing and competing in a world run by ciswomen. With or without men. I labored under the impression if I could present well enough as a woman with my makeup and fashion, that would be all I needed to do to enter the world as a trans woman. I totally ignored all the layers of life a female needs to go through to be socialized into a full-fledged woman and I was painfully aware not all females make the transition. And even more aware of the path I would have to take to make my own transition because I had even farther to go to make it to my goal. I needed to be even better than the average ciswoman to be able to be accepted in the world and be allowed behind the “sacred” gender curtain which women used to provide a layer of protection from men.

On my path to going behind the gender curtain, I had at least one big stop sign I needed to work my way around. It was proving how badly I wanted to give up all my male privileges and start all over again. I just did not magically appear in the ciswoman’s world asking for admittance without paying my dues. My transgender lost department was closed as a man, and I found I had done the right thing by pursuing a feminine life. My only problem was that I was impatient about the road I was going down and constantly I wanted more. Before I knew it, I was even getting ahead of myself in the plan I had set up for my grand gender transition. Here I was busily carving out a new feminine life where no one knew me as a man while at the same time I still had a loving wife, family and good job to deal with because I knew I could lose them all when I found my transgender self completely.

My problem also was, I was filling out my gender workbook faster than I ever imagined I could and my plans were coming into focus. No longer did I have just dreams of the possibility of transition into a feminine world, I had the reality of doing it. My lost and found was gone from my male side and he had finally begun to see the reality of his situation and gave in to the feminine side of life which was taking over for better or for worse.

It was at that point in my life when I pursued my ultimate dream of pursuing HRT or gender affirming hormones as the next step in my transition to being a transfeminine person. I went to a doctor for a physical and was approved to start a minimum dosage of the precious new hormones I was taking. Almost immediately, my body began to feel the changes as if it had always been meant for them to happen. The changes always take a whole blog post to describe, but to put it simply, my internal changes such as my new emotions would fill a book. The external changes became quickly obvious too, as my hair grew along with my breasts and my skin began to soften along with the angles of my face. I can only describe the changes as amazing and magical as they made living as a man impossible to me anymore. I had to close my male life and never look back.

I can not oversimplify it enough about all the stress and work I put into to close my transgender lost and found for good. To be sure, it was a labor of love to do it, and I would have never had it any other way. If Indeed I had another choice anyhow. Once I determined I never really did, I could relax and get rid of my guilt about doing away with all the male privilege I had worked so hard to earn. In the end though, it was worth the struggle.

 

 

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.

 

 

 

Thursday, March 12, 2026

In the Snake Pit

 

Image from Jeff Turnale
on UnSplash.

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

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

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

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

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

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

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

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

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

 

 

 

Pressure Tested as a Trans Woman

  Image from Jayson Hendrickson on UnSplash.  As I moved along in life, I became pressure tested on both sides of the gender border. On th...