Thursday, February 29, 2024

Being a Gender Victim


Image from UnSplash

Many years ago during my years of searching for my true gender self, I spent many hours and days being a victim of my circumstances.  In other words, I felt sorry for myself wanting to follow a feminine path in life. 

Primarily, thanks to input I received from my second wife, I began to pull myself out of the victim category and accept the way I felt. My wife kept telling me I didn't know anything about being a woman (which I didn't) so I needed to find out what she meant because she was not offering any help. Sadly it wasn't until many years later following her passing away, did I learn what she meant. Obviously, since she can not speak for herself, I think she was expanding on the times when she called me "The pretty pretty princess." Those were the days when I obsessed on how I looked as a cross dresser and not how I felt as a novice transgender woman. Had I not been so narrow minded in my quest for femininity, I think now I would have spent way less time feeling sorry for myself. Why couldn't I have hobbies such as golf rather than dressing as a woman.

My life turned out to be a double edged sword about that time. Not only was I facing pressure on the home front to learn more about the basics of being a woman, at work through promotion after promotion, I was feeling increased pressure to perform there also. To help me along, the many managerial training sessions I attended gave direction on how not to be a victim.

Finally, I slowly learned to attack my problems head on and not run from them. Often by putting on a dress and feeling sorry for myself. Slowly but surely, thanks to no small part to the women I worked with, I began to look beyond how they looked into how they acted and reacted with life. The whole process made me a better person and prepared me for a future living life as a transgender woman. I was becoming so much more than "The pretty pretty princess." At the same time, not being a victim was making life so much more complex. On one hand I was making strides with my makeup and fashion and on the other I was becoming very successful in my work. In fact, it was not becoming unusual for my wife to ask for my help with her makeup when we were going out to an upscale event.  Usually, after I did help her, she felt better and I was jealous I wasn't the one in the pretty dress. 

Throughout the entire process, I found I had more courage than I had ever thought possible. Perhaps the time I spent in the military prepared me with the confidence I needed to move forward and not be a victim to my gender issues. Every time I conquered a goal I thought was unachievable, I felt more natural with my life and my mental health improved. 

I put being a victim behind me and set out to be an out and proud transgender woman.

Wednesday, February 28, 2024

Changes and Trans Life

David Bowie and Changes

One of the only constants of life is change. From the day we are born until the day we die, changes are part of our life.

I am biased but I think all transgender women and/or trans men receive more than our fair share of change. Depending where your age may be in the spectrum of life and how long you are able to live, you may have to bring more baggage with you when and if you decide to take the huge step and decide to complete a transgender transition. 

In addition to the "Three F's" or family, friends and finances, there are other baggage items to consider. Such as how did you fill your time when you weren't working for instance. In my case, I was a huge sports fanatic and wasn't sure if my passion would survive as a trans woman. I was left in even more doubt when I began to not appreciate my time going to so called safe gay venues. For the most part, I didn't like the people, the music or being treated like I was an out of place drag queen. What ended up happening was, I went where I was comfortable as my male self. Venues where I could watch sports on huge televisions with beer to match. I figured if I was going to be made uncomfortable, I might as well use the change to try for better.

Most importantly, I found other women (Cis, not trans) who shared my passions for sports and gave us a reason to socialize. The whole process opened up the rest of my world to more changes. By this time, I felt as if I was right in the middle of the David Bowie song "Changes." When I looked around at all my middle aged friends stuck in ruts of life, I felt so liberated to be where I was although at times I was petrified of exactly what the future may hold when I transitioned into a fulltime womanhood. 

Little did I know, the biggest life changes were still ahead when I decided to throw caution to the wind and pursue beginning gender affirming hormones. In addition to the obvious bodily changes such as breasts, skin and hair growth, I also found myself reacting to yet another puberty experience in life. The first time I experienced a major hot flash still is a vivid memory when I think back to wondering if I was internally combusting. In addition, hot flashes and the hormones led to me all of a sudden being more emotional. As the world around me softened, I became more in tune with temperature changes and smells. It was my own special world and I loved it.

Looking back at the whole process of gender changes I went through, even though I knew deep down I never really had a choice, I cherish most of my life as it turned out. At the least, I was never bored and was always challenged to do better. First as a cross dresser and later as a transgender woman. I found the path was less traveled but when I discovered a fellow traveler, the meeting was normally positive. 

I also had privilege of living through the birth of the internet era, which in turn started the explosion of social media. Which brought the LGBTQ+ community together. All of a sudden it was easier to bring a little light into previously dark gender closets. 

Change is similar to a roller coaster ride. You can only hope the ride up is worth the ride down.

Tuesday, February 27, 2024

How Did I Know


Image from Shane 
on UnSplash

Every now and then I get asked how or when I knew I was transgender or at the least had issues with my gender.

In fact the last time I remember anyone asking was when my daughter and I were discussing her own child's gender issues and the extreme possibility the child was preparing to come out as trans to the world. To start with, my daughter has always been one of my strongest allies, supporting my gender journeys in everyway she could. So she knew more than a little about the process of joining the world as your authentic self. 

Regardless of all of that, I answered her question the only way I knew how. Even though I may not been able to vocalize my gender feelings in a way anyone would understand (including myself), I knew deep down something was wrong in my world. Perhaps my strongest indication was when I woke up in the morning saddened because I had just dreamed I was a girl. Somehow I thought most if not all the other boys I knew did not have their basic gender to worry about on a daily basis. 

The honest answer to the question became, I had always known I was born with a feminine soul and wanted to express her as much as I could. And I also learned the hard way to try to purge all vestiges of her existence was a waste of time and money. All it really did was depress me and destroyed my mental health even further than it already was. Since I had already been diagnosed with a bi-polar disorder, I had a couple of therapists try to connect the dots between my gender issues and me being bi-polar. I knew, one was separate from another and resisted their theories until I found a therapist who took the time and effort to understand where I was coming from. 

In many ways, the real question became not how did I know, to how did I cope with the change. Even though my grandchild was blessed with an understanding set of parents, they still faced the normal who, what and why questions any transgender person has to live with. When you pile on the normal challenge of life, the entire process we live with seems so unfair. But then again,(you undoubtedly have heard this before), who said life had to be fair? 

Another hurdle I faced when I was deciding to finally give up my male life and come out to the world was understanding myself. For nearly a half a century I fought my male self for dominance and when I finally decided to give it up, it was such a relief. The whole process felt as if I was taking a huge load of bricks off of my shoulders. At the time, I was very much out in the world as as serious cross dresser anyhow, so the jump I needed to make was not as far as it would have been earlier in life. So why not come out before I became any older. Since I was in my early sixties by then. I knew it was past time to live my truth.

One thing which makes me recoil in anger is when someone makes the statement I am less trans because I waited so long to come out. When in fact we all deserve the respect to come out as we please because every life is different.  The end result is all that matters. 

If you think you know you are transgender or are slowly coming along in your exploration process, all power to you. The bottom line is it your life, live it the best you can.    

Monday, February 26, 2024

Warhol Revisited

Actress Candy Darling 

Years ago, I joined several transgender friends for a short drive to The Ohio State University for an exhibit they were hosting on the works of  Andy Warhol. 

To begin with I made the decision to not wear heels like most of the other friends I went with.  Since I had some sort of an idea of where the exhibit would be on the spacious Ohio State campus the decision saved me quite a bit of pain. While my friends were crippled, I was comfortable in my flats. Probably, most importantly, I was able to enjoy most all of Warhol's varied works I saw, not just his transgender followers.  

Such as, at the time, we knew of the connections between transgender women and Warhol. Specifically the beautiful trans actress "Candy Darling" who tragically died at the age of thirty from lymphoma in New York City. Not being totally into the Warhol at the time, I really had no idea of everything the artist was into. The exhibit was massive and quickly a few of my friends seemed to be getting bored. So much, to my chagrin one of the trans women flashed the world on an escalator between floors when I was immediately behind her. Fortunately, no one seemed to notice her obscene act and no harm was done. From then on, I kept my distance since the exhibit's audience included many kids. As far as the public was concerned, they were not paying us any attention and I wanted to keep it that way.

From then on my bored trans friends decided upon leaving Warhol behind and going to a nearby gay venue. Following my experience with one of the women at the exhibit, I wondered how she would act following a couple of drinks so I did my best to again distance myself from her at the bar. Plus, I knew from my experiences in male gay venues, most of the other clientele would not be interested in her and her new genitals anyhow. 

From then on, since we had nearly a forty five minute drive home from Ohio State, we didn't stay too long and headed for home.

Far from being any sort of an art critic at all, I was surprised how interested I was in the entire collection of Warhol's work. As far as the rest of the transgender women I went with, I never saw a couple of them again and just stayed in contact with Racquel who I mention here fairly often. I always respected her for her trans journey to living an authentic life. 

If I had the chance, I would revisit Warhol again and I am sure my wife Liz would also. She is much more an appreciator of the arts than I am. Sadly today, with my mobility issues, I would struggle to enjoy his work again.    


Sunday, February 25, 2024

Impostor Syndrome?


Halloween Girls Night Out
Jessie Hart Archives 

In many ways, this post is an extension of yesterdays work. 

Impostor syndrome to me means not feeling at home in a space where you worked hard to find yourself. It is especially true when it comes to transgender women and trans men. Specifically I know a couple of trans men who suffer from impostor syndrome even though they are undetectable in their adopted authentic gender presentations. I am fond of telling one of them, they have transitioned into better men than I have ever known. 

Even still, imposter syndrome is difficult to shake. My earliest problems with I.S. came when I was invited to girls nights out. First of all, I was petrified and when my fears quieted down, I could finally grasp where I was and I was living my dream. Most importantly, I did not want to turn my dream into a nightmare and did I really belong there. After all, my path to womanhood was so different than all the other cis-gender women I was with. As I said in yesterdays' post, most all of the women in the group accepted me without questioning my past. I say most, because there was one woman one night who made no secret of her dislike for me. I did my best to ignore her or on the other hand, return the favor. My largest goal was not to let her ruin my experience. Which was so so fragile to begin with.

To this day I still suffer from gender impostor syndrome on occasion. I don't know why after all these years of living as a transgender woman fulltime why I would but I do. Perhaps it is because all the years I lived through to get to this point at times seemed as if I would never make it. All the years of going home with tears in my eyes from public scorn took their toll on me. All the years of trying to know myself when the answer was right in front of me all the time. Including the days when restroom privilege's were difficult to come by also. I had the police called on me all the way to being screamed at by a transphobic woman one night in a venue where I thought I was safe in. 

It has always been my theory that genetic women (or men for that matter) are just born female or male and need to grow into being women or men. As humans we need the time and experience to grow into our mature gender selves and sadly, many never make it.

I suppose this is the main reason I still fall for the occasional bout of gender impostor syndrome. I just haven't had the chance to pay all my dues I need to pay on the bumpy journey out of my closet and entering the world as a novice transgender woman. Even though I have spent over a half century of work to arrive here.

Happily, my battle with imposter syndrome seems to be almost at an end. I now have the confidence to realize I belong in a space as much as the next woman. I just have to continue to adjust to the way women are approached in the world. It was my own personal journey to my own unique trans-womanhood and I own it totally.    

Saturday, February 24, 2024

Making the Difficult Easier

Image from the
Jessie Hart archives.
I spent years and years admiring every aspect of how women and the girls around me conducted their lives. I was dazzled by how they moved and interacted with the world. 

On so many levels, I wished I could be just like them but for so many reasons I could not. No matter how hard I tried, I couldn't shake the shackles of my pre-ordained male existence In order to survive in a male world, I needed to copy and succeed at being a guy. All of made the dramatic gender transition I was about to make later in life that much more difficult. 

As I moved from a cross dressing mirror into the real world, I discovered the feminine gender had so many other layers to their life's than I ever imagined. So much more than merely looking like a woman which turned out to be the way I could slightly open my closet door to the world. When I worked my way past the first layer of cis-gender women I faced in clothing stores and malls, then the hard work started. 

All of a sudden, I found myself in a position where I needed to communicate with the public as a novice transgender woman. In the past, my second wife had told me repeatedly in no uncertain terms I did not know anything about truly being a woman even though I was becoming fairly competent on looking like one. She was right and I didn't understand it. 

One vicious argument comes to mind from when we lived in the New York  City metro area and happened the day after I went to a transvestite mixer. What happened was, I needed to show my identification card showing I was really a male to even get in. For the next couple of days, I was on a massive ego trip which led to a big fight with my wife. It led to her comment I still vividly remember when she said I made a "terrible" woman. I could not believe she could say it after I had almost been refused admission to a cross dresser party for looking too much like a woman. When I told her my problem with what she said, she promptly told me, she wasn't referring to my appearance. From then on, I was determined to find out what she meant. It was difficult to do because my wife did not particularly care for my feminine side, so I was on my own.

It was only easier when years later I was able to break out of my old male bonds and be able to finally play in the girls sandbox. Along the way, I had learned the power of non-verbal communication between women as well as surviving the effects of passive aggression when I had to guard my back from smiling faces. When I did, my mental health improved along with my self confidence as a transgender woman. I came to realize (with help from my friends) while I could never be a cis-gender woman, I could be a proud transgender person. I achieved my womanhood through a different path but I made it. My presence in the group just made it more diverse and nobody questioned me about my past.  

In order to do it, I needed to reverse years and years of male life. Moving like a woman needed to become my primary goal since I was never going back. Also very difficult was how I was speaking to the world. I did my best to mimic the women around me and even took vocal lessons for awhile. Eventually all the work came together and I became confident in my abilities to survive in the feminine life I had always dreamed of. 

Friday, February 23, 2024

Mom Approved

Image from Kelly Sikkema
on UnSplash
Very few transgender women or trans men have the benefit of an approving Mother. I can't imagine my Mom ever providing me the fashion or the help to become the girl I strongly wanted to become. 

My parents were members of the "greatest generation" who went through the great depression and WWII. Both of those major events certainly shaped them into individuals who were strong on providing for a family and weak on emotional support. Which was exactly what I needed. My Dad's family was very male dominated and my brother and I were expected to follow in his footsteps. Wanting to be feminine at all did not fit in to the advance family plans my parents had for their eldest son. I was expected to grow up, go to college and marry into my social class or higher. Quickly I was discovering, I had different ideas.

Even though I was busy playing sports and working on other male activities. I can't say I excelled at any of them but I tried my best. One thing is for sure, I was on my own because there was no way I could ever bring up my true gender feelings to my parents. Especially my Mom, who often took the lead in raising my brother and I. So, I was solidly hidden away in my dark lonely closet until I could break out much later in life. 

Through it all, I still sought out my parents approval. My Dad was very difficult to out due because he was very much the stereotypical self made man. He built his own house and rose to a bank VP position with a high school diploma. He served in the Army Air Corps in WWII, so at least my military duty in many ways corresponded to his. My brother on the other hand thanks to a high draft number, never had to serve at all. It took until I was out of the Army for me to try to come out to my Mom. One night after drinking with my friends, she was waiting up for me (before I could move out into my own place) and I blurted out I was a transvestite. I don't know what kind of a reaction I thought I would get but it was anything but the negative one I received. She recoiled and immediately volunteered to pay for therapy which in those days was the approved method for dealing with gender dysphoria. I basically said go to hell and that was the last time it was it ever brought up to her. And I never came out to my Dad either before his death at the age of 86. 

It took my daughter to break the chain of family disapproval of transgender issues and help with our over all family mental health. Growing up, my oldest grandchild (a girl) kept showing signs to my daughter she was having issues with her gender. When she was mad at Mom, she would say things such as what if I liked girls instead of boys. Since all three of my grandkids knew I was transgender, threatening my daughter with gender issues was pointless. Now my eldest grandchild goes by the "they" pronouns, has a partner and goes to The Ohio State University. Needless to say, I am so proud of my daughter and her family. It shows how much can change in a generation or two in a family. 

Even though my Mom never approved of my feminine soul and I never had her input on my cross dressing desires, I understand now she was just a product of her generation. During her later years, she was a little difficult to deal with, so as I said, we never discussed my gender issues again. I wish now I would have given her the opportunity. 

To make up for it, I adopted her first name as my new legal middle name when I changed my gender markers years ago. It was the best I could do to bury any lingering resentment I may feel. Maybe somewhere now, I am Mom approved as the daughter she never had.   

Thursday, February 22, 2024

Tearing Life Apart


Image from Darius Bashar 
on UnSplash

Sadly, before many things have a chance to change, you have to tear them apart and then reassemble the parts. 

In order for me to pursue a life as a transgender woman, it was necessary for me to essentially tear down my past male life and start all over again. This was painful for several reasons. The main one was I was giving up all the hard work I put into to surviving in a male world. Secondly, I needed to fight the male in me completely because he was totally fighting any gender change which was happening. 

It all started when I left the mirror as a novice cross dresser and went into the world. I learned the mirror was an easy challenge until I faced the public. Primarily because the mirror didn't move and neither did I so when I may have stumbled on the perfect look with my makeup and fashion, it all had to change when I needed to put it all into motion. Was I walking and talking like a woman? The whole process caused me extreme gender confusion when I was trying to separate the days when I was a trans woman with the days I was in my everyday working life as a guy. Perhaps the biggest problem I faced was dismantling one life and beginning another in the middle of the entire transitioning process. I felt everytime I was successful in public as my novice transgender self, I had to stop and return to a male world I increasingly didn't want anything to do with. 

Even though, I was risking all I had worked for in life including a loving wife and family and a good job, the fact still remained I thought I was living a lie. I just couldn't keep living a lie and continued to tear down my old life and prepare myself for a possible dream scenario where I could possibly live as a fulltime transgender woman. The entire process was cruel and unusual punishment to me and destroyed my mental health until I could get it restored much later in my life. In the meantime, I needed to find ways such as diverse gender mixers I was going to, to try to feel better. It seemed everytime I attended a party made up of everything from cross dressers to transsexuals, I learned more about myself and where I fit in to a new expanding LGBTQ community. Primarily the new term (transgender) which seemed to fit me the best. 

As I was busily considering tearing down one life, I had other serious others issues to contend with. Such as my sexuality and how was I going to be able to communicate in a new world as a trans woman. It turned out, I was overthinking the whole process and destiny would come along to answer my most pressing questions. You regulars know the story of how I found and was adopted by a small group of cis-gender women who taught me the basics of communication and how to conduct myself in my new world. And then there was my wife Liz who rescued me from very dark times, took me in as my authentic feminine self and eventually married me.

It has been such a long trip from standing cross dressed in front of the hallway mirror growing up and the ups and downs of tearing one life apart to start another has been scary. But eventually I made it.  

Wednesday, February 21, 2024

Writing Euphoria

Image from the Jessie Hart

Every now and then I receive a comment which brings all the effort I put into writing a daily transgender blog into focus. 

When I started writing this blog over ten years ago, I set out to hopefully help anyone else with gender issues similar to mine. Back in those days, when I revisited my old blog posts, I mainly see an over riding interest with my feminine appearance and not much else. Of course when I transitioned into a fulltime life as a transgender woman, I discovered all the other challenges I was going to face. It was all much different than my life as a casual cross dresser. 

This is where the writer's euphoria comes in. I recently received this comment from Jennifer " Thank you for publishing your thoughts and experiences. I am an older, but not that wiser, transgender woman just starting out on the road to femininity. Your blog helps me much to understand the hurtles I am about to encounter. Thank you for sharing your thoughts and opening up to your experiences.

Thank you, Jennifer" You are welcome Jennifer and thanks for sharing such a wonderful comment. 

Somehow, along the way, the blog made it's own transition into looking at my life as a senior transgender woman. I found, being "more mature" in many ways had it's advantages. Primarily when it came to beginning gender affirming hormones. Because at my age, my testosterone level was already in a decline, the rush of new estrogen in my system seemed to be more natural. On the other hand of course, I needed to go through the medical screening process to determine if I was healthy enough to proceed on the program I was prescribed

As far as being "older but not wiser", I think I faced that aspect of my life also more than I could ever write about. For better or for worse, I had already went past and missed my formative feminine years and needed to master the mysteries of makeup and fashion on my own. There were no teen girls to critique my look and for me to return the favor. Plus, I spent way to much time alone with no girlfriends to shop at the mall with. 

I discovered too, there was a small niche of older transgender women who had lived through the dark and lonely pre-internet years. I am amazed how many readers still remember fondly the "Transvestia" publication along with Virginia Prince. But then again, it was all we had to provide any sort of light in our gender closets. 

These days, I am still committed to attempting to provide any guidance I can to anyone like Jennifer who needs it. After all, our gender journeys through life on one hand are so similar but on the other not so much. Each of us needs to navigate how we are going to shed a life of living male and begin all over again. And just when we think we have it made, we need to face the reality of being trans in retirement communities and/or assisted living. Regardless of all the negative publicity we receive from politicians, I still believe more people such as the "Alzheimer's Association" are researching ways to be more inclusive to the LGBTQ community. So, there is hope. 

Thanks again Jennifer, Jen (another reader) and all the others of you who join in with me here on the blog. You give me writers euphoria and improve my mental health.

Tuesday, February 20, 2024

Gender Euphoria

My wife Liz on the left
From the Jessie Hart archives.

Sadly, gender euphoria is too rare for most transgender women and trans men.

For too many of us (including me) gender dysphoria rules the life.  Throughout my life when I get up in the morning to begin my day, a quick look in the mirror tells me I am living my external gender as yet another day as a guy and my gender dysphoria sets in. I describe my gender dysphoria as being a deep seated issue caused by my desire to live as my authentic feminine self. From then on my day is set on how it will go.

However, every now and then something comes along to reassure me I am doing the right thing with my life. It could be as little as my wife Liz referring to me as "she" all the way to a server calling Liz and I "ladies" at dinner when we eat out. Whatever the case, gender euphoria is brief and dysphoria is always lurking in the background. 

I think part of the problem is all the difficulty I experienced as I followed the path to living my transgender dream. In the days when I just considered appearance as my number one feminine dream, of course there were always plenty of other women (trans or cis) to compete with because they were far more attractive than me. My impossible dream was to do the best I could to survive in a sometimes brutal world as a novice cross dresser or transgender woman. Initially, I made the mistake of attempting to dress sexily to validate myself in the world. All too often, my attempts came off as trashy or even clownish. Plus, one night my wife had to rescue me from a huge man at a party who had pinned me against a wall in a narrow hallway. In no way was there any gender euphoria or feminine validation involved that night. Just my wife reprimanding me for not taking better care of myself ahead of time. Not to mention, she hated what I wore. In my mind, I was trying to keep up with the beautiful transsexual women who were there also.

Through it all, I managed to have enough moments of pure gender euphoria to keep my gender dreams alive. Very early on all the visits to mall and women's clothing stores provided me with positive one and one feedbacks with the clerks to think I was doing everything right as a novice feminine cross dresser. It took me many years to realize, the clerks were mostly nice to me because of my money. Years later, after I came out to my daughter, she told me of her days working at Victoria's Secret when the occasional man would come in shopping for lingerie in his size. Other clerks would refuse to wait on him but my daughter did and pocketed the commission. I could have been green and most of the clerks would have still liked me.

My mall days continued my gender euphoria to an extent I never thought possible. I used to go to the up-scale malls in the area in my very best business professional fashions. Including a very stylish black jumpsuit I loved with my black heels and blond wig. It seemed I never had any problems and my euphoria soared along with my confidence. Sadly, I normally found a way to push the so called envelope too far and get rejected in the world and my gender dysphoria would set in again.

It wasn't until I began gender affirming hormones did I reach the point of no return in my male to female gender transition. Regardless of what happened to me, negative or positive, I needed to attempt to move forward towards my dream. Happily, the feminine hormones improved my exterior image. My skin softened, my hair grew and my facial angles softened which made my whole presentation easier to do, since I needed to do it every day. 

Even with all the help. I still have the dysphoria/euphoria battle with the mirror every morning. Sometimes I win the battle, sometimes I lose but most importantly, I have learned neither aspect of my appearance should rule my day. Nothing is as good or bad as it seems.

Thanks to all of you who join me for my experiences! I appreciate you taking the time to stop by and even comment. It all means the world to me.

Monday, February 19, 2024

It Was Never Easy

Image from Alexander Grey
on UnSplash

 Two things amaze me when people bring up to me when they learn I am transgender. The first is when someone thinks I had a choice and the second is the entire process was at all easy. 

Since I was never a so-called natural feminine person to begin with, I needed to struggle completely to reach my goals of surviving in the public's eye at all as a woman...trans or not. The best description of my passing struggles came when my transgender friend Racquel told me I passed out of sheer will power. I knew what she was trying to say. I wasn't the best looking woman in the room but I was going to force the issue anyhow. 

Early on, I had only the mirror to do my gender battles with. I finally learned too late the mirror often lied to me. Night after night, I would think I looked great only to be immediately stared at or even laughed at in public. It was difficult learning how to try to dress myself so my feminine fashion helped me to live a life I had only dreamed of, not hurt it. At the same time, I tried to lose as much weight as I could and take care of my skin so I could wear less foundation. None of it was easy. But it was worth it.

In order to accomplish all I wanted to do on my difficult gender journey, I needed to learn something new and different. I had to learn to be my own best friend. I never liked my old male self and was just learning all the new possibilities of my feminine inner soul. She had many problems to face as she fought for acceptance from my male self who fought completely for all of his rights. At times, it was an ugly, bloody battle I never want to go through again. It was anything but easy and never a choice to go through as I was to find out later. 

I ended up suffering so much, I almost ended my life several times from various reckless self harm attempts all the way to an attempted death by pills which failed before I decided enough was enough. In order to survive I had to make a choice, so yes I guess I did have a choice and it was a very desperate one. Self survival meant I needed to pursue what measures I could and change my life forever. The final determination was deep down I felt more natural as a transgender woman and needed to find out where I would need to end up in the new pack of women in society. It was then I learned how deeply layered a woman's life could be and perhaps even more so as a trans woman. I had all the extra baggage of my previous life as a man which I carried with me to the other gender side. I knew the male gender expectations men had of women which made me extra shy of the entire gender dance between men and women. Primarily I learned why both genders often have a difficult time communicating in their relationships and wished often I could go back and do my life different. Maybe then, my second wife would have never said I made a terrible woman. Which I did and thought it only had to do with how I looked.

The final example for this post I will use was the amount of time it took me to finally face reality and come out fully as a transgender woman. Adding up the years, I struggled with my ultimate gender issues for nearly a half century. It was certainly difficult to break out of my old male chains and live the life of my dreams. I realized I never had a choice.

Sunday, February 18, 2024

You Can't Buy Love

Image from the 
Jessie Hart Archives

 One of the first lessons I learned when I was first brave enough to date girls was spending more money equaled to more dates with certain girls. Sadly, the plainer the girl, the less potential spending was going to happen. When I flipped my gender, I found out how evil it was.

As a transgender woman, I was or am not the prettiest woman in the room. As such, I never managed to have many dating interactions with men who most of which just saw me as some fetish object. They wanted the first date to be a motel room. I drew the line at any sketchy first dates and demanded a meeting in a public place of my choice. What happened then was a predictable amount of being stood up on possible dates. While I did have a couple meaningful dates with men, often they were unscripted moments in the regular venues I went to often. One night in particular happened with a man called Bob who treated me completely as a woman and I loved it. He lived far away and was married so there was no chance at any further involvement. 

Through that period of my life I was questioning my sexuality also so any dates with men added to my possible knowledge. The farthest I ever went was very brief episodes of heavy petting or making out. From it all, I learned I still preferred the attention and company of women. With the help of a few female friends I learned the meaning of what it meant to be to be a transgender lesbian. In order to do it, I found I didn't have to have a lot of money spent on me to be happy. I was more into spending more money on my feminine self to attempt to improve my public's appearance. I ended up saving every extra penny I had to buy that next extra wig I didn't really need to be more attractive than ever before. At least in my mind. As I acquired more fashion and makeup, slowly but surely was acquiring more acquaintances to try my new fashion out on.   

Which leads me to another woman I don't mention much anymore who is Amy. Amy is the woman who recommended me practice with a banana to get ready for my intimate moments with men. So as you can tell she wasn't shy. One day in particular  with her comes to mind when she invited me over to her house for a spaghetti dinner with friends. I didn't really ask who else was coming, I jumped at the chance to enjoy a home made dinner. Fashion wise, Amy had only seen me in my short denim skirt days, so I decided to wear one over to her house again not thinking who else would be there. It turned out she also invited two men so the group included a cis woman, a transgender woman and two men who were seemingly ill at ease with me. I made the decision to join Amy in the kitchen and serve the men their delicious Italian dinner. I decided if the men were going to be ill at ease with me, I wasn't . I enjoyed the meal, helped clean up the mess, stopped to socialize with Amy and left the men behind. Just another learning experience.

I finally was able to slow down on expenditures on fashion and makeup and spend more on my personal interactions. My experience with dealing with both sides of the binary gender spectrum helped me to truly understand what buying love really meant. I understood both genders often expect intimacy in return for how much money you spend. The last woman I ever dated me as a man suggested to me we go to an expensive steakhouse for food before our first date. I politely saw through what she was up to and declined and we went to a more reasonably priced venue of my choice. Probably dooming our relationship from the beginning. She was quite attractive and a diva to begin with so I figured she thought she could do better than me and our brief fling ended after three or four dates.

Since we live in a money driven society, buying love is hard to do and even more difficult to resist as a transgender woman.  

Saturday, February 17, 2024

Following the Path


Image from the 
Jessie Hart

The path I followed as I chased my gender truth at times turned out to be very difficult. 

It all started with having a very unaccepting family environment and continued from there. Similar to so many of you, I needed to wait for just the right time to pull out my small stash of girls clothes and cross dress. Because of that my available times to dress up and do my best to follow my new path were few and far between. Plus, the signs I desperately were looking for were distant and difficult to read. When I came to gender cross roads, I was having a hard time figuring out which one to follow. 

This was all happening during my pre teen years so I was confused enough about my life to start with. On top of the usual questions kids had growing up, I had added problems wondering what gender I was, all the way to my sexuality. I felt as if I was attracted to girls during puberty but the how I was attracted became the problem. I was facing the sexuality issue of desiring women because I wanted to have sex with them when all I really wanted was to be them. To make matters worse, I was extremely shy around people I didn't know. Especially girls. None of it was making my path any easer to follow.

To make matters worse, when I was in high school, the political powers to be decided to dramatically expand the United States presence in Southeast Asia or the Vietnam War in particular. On top of all my other worries I needed to add possibly being drafted to serve in the military. Not a good feeling to carry with me all those years. How could I possibly serve if I didn't want to be a man at all. It turned out, I didn't have the choice after I stayed in college for four years, I was drafted anyhow and my path became very clouded. 

The best I could, I went down my path adding three years in the Army to my life experiences. At the least, I had more knowledge of the world to base my gender decisions off of. Or, at least I thought so. Not long after I was discharged from the military, I went through the life altering experience of having witnessed the birth of my first and only child, a daughter who turned out to be my biggest supporter to this day.

As I was building a rather successful life as a man, I also began to explore other cross roads on my gender path. Possibly the biggest one was when I started to think of myself as more than just a casual cross dresser and more of the newly minted transgender individual. Most certainly just thinking I was trans rather than a guy in a dress petrified me. To make up for all my gender fears, I did my best to hide my true authentic self from the world. When I did, I kept hitting more and more dead ends on my path. 

Years later, as I was stumbling along attempting to find my way, I sustained so many bumps and bruises I could take it no longer. I made the effort to see a doctor and be approved for HRT and all of a sudden my path became more of a highway to my future. I guess it was more like an interstate as I was able to easily pass more and more milestones on my journey. 

It certainly took me long enough to get to my destination but once I did, it was all worth it.

Friday, February 16, 2024

Gender Migration


Image from Stephan 
Stephancik on UnSplash

From the early days cross dressing in front of the hallway mirror to finally coming out in the world as a transgender woman, I found my gender migrating away from my masculine side. 

The migration was slow at first because my old male self was resisting any and all changes to his existence. It seemed the more I tried to cross dress as a girl, the more he hated the process. The problem quickly became more apparent after I appeared in the mirror as a girl, which would involve or invoke a fast reaction as he responded negatively to anyone else in the world. Family and friends became targets of his gender frustration. Why? Because even though he did not know it, he was fighting an impossible battle. Even though it was possible for him to win the occasional battle, there was no way he could win the entire gender war. My feminine inner soul was just too strong.  Every time she was successful in coming out to the world, she wanted more and more.

Through my life's middle years, advancing in my job and raising my daughter, my migration slowed but never went away. In fact, it showed up in the most inopportune times when I had company business meetings to go to, or a family vacation to act as if I was having a great time when all I wanted to do was go on the vacation as a transgender woman. Of course my wife always sensed I was having a problem and tried her best to pry my thoughts away from me. I became very good at hiding my emotions as any true man would. 

In my case, I found if I waited long enough and tried my best to express my true feminine gender the best I could away from my wife and friends, I could get by. Those were the frustrating migration days of sneaking out behind my wife's back and beginning to establish myself as a woman in the world. At the time, I viewed the entire process of slipping down a very steep and slippery slope which would change my life forever. As much as the process scared me, at the same time I desperately wanted it to succeed. At times, too much when I couldn't keep my mind on which gender I was day to day. I knew I had gone too far when a stranger in my restaurant would refer to me as a woman instead of the macho man I was playing that day. 

Finally, I gave up, started gender affirming hormones and started a totally serious pursuit of a gender migration. From that point onward, I let go of my old unwanted male self and re-entered the world as a transgender woman. As I always point out, friends and family were there for me to enable my final migration to be a successful one. I am not sure I could have done it without them. 

Thursday, February 15, 2024

Another Holiday?

My Favorite Valentines. Liz on left, daughter 
on right.
From the Jessie Hart Archives.

 Following the Christmas holiday season which presents so many problems for transgender women and men, here comes yet another rather traumatic holiday. 

Both of the holidays revolve around personal relationships, to which trans folk often have lost close friends or family because they set out to live as their authentic selves. When I read all the social media posts from transgender folk who are lonely, my heart goes out to them. The entire process just goes to show how much a person can lose following a gender transition. Once again it shows how much of a choice we don't have when we set out on our gender journeys. 

I am fairly sure I didn't think of losing family the first time I looked at myself cross dressed as a girl in the hallway mirror but then again maybe I did because I was so frightened about getting caught. Maybe my fears were justified so many years later, when I did lose all contact with the brother I was afraid of exposing my secret to so many years ago.

Overall, I know how fortunate I am when certain holidays such as Christmas and Valentines Day come around each year. Through a mix of work, destiny an sheer luck, I was able to find another person in the world who accepted the authentic me. My wife Liz basically picked me up off the trash heap and made me a believer in myself again. Something which I thought was impossible at my age of sixty two. In fact, I had given up on the idea of another serious relationship in my life and felt I was doomed to live alone as a transgender woman trying to make her way in the world. 

Perhaps, more importantly, I was able to rebuild family connections which were lost. Through my daughter's in laws and Liz's family, having a Christmas with family and friends became a reality again. And, even though I had never been a big believer in Valentine's Day, it is still very nice to tell Liz happy Valentines Day and I love her and for her to return the favor. Plus, I can't forget all my bonus checks which were added to because of Valentines promotions in the restaurant business I was in.

At the least, Valentines Day only lasts for one day and hopefully you can mend the hurt you may feel from having no one to celebrate with. Anyway you cut it being transgender should not deny you a chance to be happy with another person...but it does. 

It is just another holiday designed to stimulate certain areas of the economy not hurt the ones who happen to be single when it comes around. If you are one of those people, Liz gives out the best hugs and I am sending a big one to each of you.

Wednesday, February 14, 2024

Beautiful...Inisde and Out


Image from the Jessie Hart 

As I obsessed with looking the best I could as a novice transgender woman or cross dresser, all I could think of was how I looked. Little did I know there was so much more coming up in my journey to living fulltime as a trans woman. I needed to live my looks as well as just admiring myself in a mirror. 

This morning turned out to be a prime example. Today I tagged along with my wife Liz to her mammogram appointment. Before I went, I applied my usual minimal amount of makeup, brushed out my hair and was essentially ready to go. While I was doing it, I felt it was time for a change. I thought I have been in a rut I have been in too long. I have essentially stopped working on my appearance and then being shocked when I am mis-gendered. 

Of course, nothing negative happened morning when it came to the doctors appointment because there were very few people waiting to begin with plus no one was paying any attention to anyone else. Since I had a spare moment, I went shopping on my phone for a foundation specifically tailored for older women. A group I naturally fit into. I found their on-line site and decided to give it a try. 

Currently, I am relying on the skin effects of gender affirming hormones, so I don't have to use a foundation at all. Or so I thought. It's occurring to me now the hormones have been a crutch for me to quit trying as much as I did. I ordered the new foundation and I will let you know my feelings. 

The end result is I need to work harder to make my inside and outside match up again. I learned long ago, similar to many cis-women, I will never be the prettiest woman in the room. I needed to find other ways to survive in the world as a new transgender woman. Little did I know, my biggest positive as a new person was already within me. My discovery was my inner feminine soul was actually good people. Opening up to others turned out to be one of my biggest pluses. The world turned out to like me. 

Doing my best to be beautiful to others, inside and out, turned out to be one of the most beneficial things I have ever done. Now, I feel it's time to get out of my rut, have some fun and get back in the game. Maybe to the point of treating Liz out to get our nails done and then have some dinner out at our favorite restaurant

I need to get us both out of the house.  

Tuesday, February 13, 2024

Dreams versus Priorities

Image from Marcos Paulo Prado 
on UnSplash

 Seemingly forever, I had the dream of leading a feminine life. 

As I progressed along my bumpy gender journey, slowly but surely I learned perhaps I could achieve my number one dream.  Other guys I knew dreamed of having a great job or a beautiful wife while, all along, all I wanted was to change my gender. It all seemed simple enough except it wasn't. In fact, it proved to be extremely difficult. 

As I lived a reasonably successful male life, it became more and more difficult to just give it up and just walk away. To do it, my dream needed to become a priority. Around this time, was when I entered what I refer to as my second major transition. It was when I went from being a very serious cross dresser to being a transgender woman or going from just wanting to look like a woman, I wanted to be a woman. The entire process seems like semantics it probably is but I was serious and I was led into gender areas I never dreamed of. Primarily when I needed to step up my game from just concentrating on my appearance to needing to learn a whole new form of communication in the world.

I was in shock when I learned how quickly my white male privileges could be swept away leaving me with very little to fall back on. My previous "hit and run" approach to facing the public needed to change if I was going to survive and keep my dream alive. 

For the longest time, I was by myself in the world as a man and a woman. My male self had lost almost all of his friends and family to death leaving him mostly all alone. Plus my trans woman self had not had the chance to establish herself as a person in the world. I was stuck in a gender limbo, until my life started to change for the better as I began to set priorities for myself. Since I really had nothing to lose, I went all out on on-line dating sites which predictably I had very little success with. Partially I think because in those days there were no sites which catered to transgender women who were not fetish items. It was complicated but I went on regular sites under different listings such as everything from woman seeking woman to woman seeking man. After sorting through tons of being being rejected, my wife Liz responded to an ad I ran asking for a woman seeking woman and we have been together ever since.

Destiny at that point intervened more completely in my dreams when my regular trips to straight venues ended up with me meeting two different lesbian women on separate occasions and quickly we became a tight knit small group. My dreams quickly became my priorities at this time of my life because I needed to step my gender game up to learn and understand what the other cis-women in my life were showing me. If they knew it or not. 

When I started gender affirming hormones (HRT) around this time, there was no turning back. I faced an all out priority to live a life I had only dreamed of. For the first time, it was so close I could reach out and touch it. Even though my life turned out to be different than I ever imagined it would be, I still couldn't conceive of living it any other way. My dreams had turned into the priority of allowing my inner feminine soul a chance to live. 

Monday, February 12, 2024


Image from the 
Jessie Hart Archives

I would suppose, similar to anyone who has reached the stage of life I have reached, may have a few regrets.

As far as I am concerned, I don't have many. Along the way, I have been fortunate to have loved and be loved by several different women. Three of which married me. In each of my marriages had their own special ups and downs. One of the regrets I do have was when I needed desperately to be the one who cheated on my first wife so I could marry my second wife. I wasn't proud of being the cheater in the relationship but I see my first wife (and mother of my only child) approximately twice a year and we get along well. We both moved on to other long term relationships which proved out to be for the best. 

I was with my second wife for over twenty five years before she tragically passed away from a massive heart attack. My regrets with her primarily revolved around me not knowing the full reach of my transgender feelings and I ended up dragging (no pun intended) both of us through the gender mess I created as I transitioned. It would have been easier if I had just pulled the band-aid off and just let the dust settle where it may. But I was selfish and still liked part of what I had accomplished as a guy. So much so, I didn't want to let it all go which was a major mistake. One which almost killed me. I would not wish attempting to live convincingly between the two main primary genders on anyone. From day to day, just to get by, I needed to concentrate which gender I was that day. I found myself in some sort of a gender twilight zone trying to figure out daily was I a man or a woman.

I did know I loved being a woman, I loved the clothes and the challenge of facing society daily as my increasingly feminine side. Sadly, as with anything else you love, many problems come with the process. Life at once became exciting and terrifying. I didn't know what I was doing as a novice transgender woman but I learned fast. At the least, I gave myself the latitude to make mistakes and keep discovering a new world. Regrets? Sure, I made many mistakes along the way as I presented myself to the world. Plus I was lucky too when I got away with more than I should ever been able to. The main ones occurred when I went behind my second wife's back to cheat on her. With another woman who happened to be me. I had always thought I was a honest person, so the whole deal proved to be excruciating to me. The more success I felt on one hand felt so natural but at the same time I was cheating on the person I loved.

I suppose everyone has regrets but destiny has softened my challenges I have experienced from the challenging idea I wanted to change my gender. Ironically, it was my third wife (and current one)who came along and saved me from myself in my darkest days. She made me a believer in myself as a person and convinced me I should have live fulltime as a trans woman. She sealed my belief in her when she told me she had only seen the feminine in me. That was over a decade ago and we have never looked back and our relationship remains strong.

It doesn't do much good to have any regrets anyhow. Life moves fast and if you didn't take the opportunity to seize it when you had the chance, it may never come around again. I am just fortunate in I have been blessed with a long life to try not to repeat my mistakes and have regrets. 

Sunday, February 11, 2024

Fear of Gender

New Alzheimer's Pride Shirt

I have always thought those who protest too strenuously over the LGBTQ community as a whole or the transgender community in particular are very afraid of their own gender feelings or sexuality.

The whole reality of gender bigots coming out of their shells in public has happened because they have been emboldened by a certain former president and his party supporters. While, at the same time wealthy MAGA financers have made it possible for them to pursue their bigoted goals at the state political levels. My native state of Ohio is a prime example. A fundamentalist Baptist preacher has been leading the charge to erase all transgender care in the state. In response, the state legislature has already passed bills restricting any care for transgender youth under the age of eighteen. To make matters worse, they have plans to try again to expand the bill to all transgender women and men in the state in the future. So far they have failed and the ACLU has promised to take the state to court over it's bills. 

As I put my anger aside for a moment, I paused and wondered what skeletons the Baptist turned politician had against me. Similar to all of the other transgender people I know, we are just trying to lead a quiet life. The better we are at staying out of the public eye, the better. Plus, don't get me started on what I feel about churches who do more than dabble in partisan politics. 

I shouldn't be surprised with a Baptist preacher leading the anti-trans charge here in Ohio since my brother's in laws are all fundamentalist Baptists and he chose them over me when I came out to him. As much as it hurt, I got over it and we have not communicated in over a decade.

All ranting aside, I am a firm believer in the power of gender to transcend and take over any other paranoia a human may have. From birth we largely have our gender chosen for us. Like it or not, using me as an example, I was obviously born a boy or male but I grew up to be a transgender woman. Not completing the gender journey I was assigned would have led me to an early death. It is my opinion, the most oppressive of the gender bigots have a fear of their true selves. They protest too much as many are clutching their crosses while they are doing it. It is tragic when people hate so much. I don't expect the public to understand me  but I don't expect hate either.

I am lucky to live in a fairly liberal part of Ohio, far away from the area where the ultra anti transgender preacher lives. So my activism comes primarily from my writings, my out-reach attempts with groups such as the Alzheimer's Association and participating in Veterans LGBTQ groups. It is essential for me to let them know how urgent the anti-transgender situation is in Ohio. Sadly I can only do a very little to financially support candidates I knew will help our cause. 

I don't suppose I will ever understand why anyone who wants to harm a person in the LGBTQ community because if you are gay and or lesbian you can't think eventually the gender bigots won't come for your rights also. They are using the weaker transgender community as a starting point. Even if you are a cross dresser deep into your closet, you need to consider your gender future and vote accordingly. 

We all need you!

Saturday, February 10, 2024

Sizing Up the Crowd


Image from Roberto 
Nickson on 

Recently, when I met friends at a local brew pub for brunch, I needed to walk the distance of what was called the "great hall" to meet the group.

Once again I needed to make sure I was standing up as straight as I could, while throwing my shoulders back and faced the reality all transgender women face, was I going to be spotted as some sort of a gender impostor and even laughed at. I didn't and even though the brief walk felt as if it went on forever, I made it to our table without incident. At that point I thought I had it made, until the young server called me "sir". Which is another sad experience I have previously written about. 

For some reason, when I transitioned into a feminine transgender world, I didn't think the public would share the same fascination with studying other women as I did. I can't tell you how many times my old guy self aggravated my second wife (and others) by trying to sneak a peek at an attractive woman. For whatever reason, I couldn't explain to them I wasn't looking because I desired the woman, it was because I wanted to be the woman. At the time, I was having a difficult time wondering if I could ever achieve my dream of cross dressing out of my old unwanted male self. There were so many working parts of a woman to duplicate, the whole process seemed impossible. I needed to fashion my own hips, breasts and hair just to arrive at a point where I could put the entire feminine package into motion. 

It wasn't until I began to leave my dark and lonely gender closet behind and attend transvestite mixers did I begin to think I could succeed. Through the help of the mixers, I was able to judge how other cross dressers were successful with their presentations...or won't. I saw everything from men in beards and dresses, all the way to beautiful transgender women who were completely undetectable as former boys or men. As I sized up the crowd, I knew which direction I was headed. Most certainly I did not want to be with the bearded crowd and wondered to myself if the transsexual group was where I needed to be. Keep in mind, this was back before the transgender label was widely understood or used. What amazed me too was how intense the pressure was to size up the crowd and fit in to where you belonged. 

Little did I know, I was just beginning my trip out of the closet and into the world and I would need to obsess on my appearance until I gained the confidence to go forward as the person I was. Deep down I knew I would never be the prettiest woman in the room, I just wanted to be the trans woman at peace with herself. So when the crowd sized me up, they recognized who I truly was and it was good enough. I learned also, the greatest majority of the world didn't care about me anyhow and they were involved in their own little worlds. My second wife was always fond of telling me it always wasn't all about me when it came to my cross dressing and she was right. It was just the ones who did care who became the problem. As I made my way along my gender path, I was fortunate to dodge most of the haters and live my life without severe incidents.

I am a firm believer in the younger generation doesn't see gender as a threat and in the future sizing up a younger crowd will be less of a threat to transgender women and men everywhere. I, on the other hand, when I chose to live a life as the high maintenance gender chose to always be on the stage of life. 

Friday, February 9, 2024

You are Such a Girl

Boho Woman from Brooke
Cagle on UnSplash

Jen recently responded to my comment about walking in heels on stairs while being slightly intoxicated. 

Jen, who I have known for years happens to be a cis-gender woman and said she has never mastered the art of walking in heels. I have always appreciated knowing Jen because of her acceptance of me as my authentic transgender self from the first time we met. As far as me judging her for not wearing heels, it never happened. 

Perhaps, I quit judging women from their footwear came primarily because all of the women I socialized with were not the girly-girly types and never wore heels. At that time, I still could wear heels but decided not to because of adding to my height as a trans woman. All my friends were shorter than me and I did not want to tower over them. 

Being such a girl, did not reach all the way to wearing makeup and the feminine clothes I wore. In order to stand any sort of a chance to present well as a novice transgender woman or cross dresser, I needed to take advantage of all the benefits which makeup gave me. In fact, when my second wife was alive, she used to call me the "pretty, pretty princess" in response to all the time I took to apply my makeup. When she wore little to none. Obviously she didn't have to worry about the benefits of fashion to just exist in the world as a feminine person. 

As my life progressed and changed, my knowledge and application of makeup needed to also. While it was obvious I still needed to take advantage of cosmetics, the new pressure was on to look natural while I did it. In other words, to appear as if I wasn't trying too hard. I desperately needed to blend in with my group of cis-women friends who again did not wear any makeup at all. It was during this time in my life when I really began to step up my skin care routine. I made sure I was able to apply a good moisturizer after everytime I exfoliated or shaved. The entire process enabled me to use less foundation and achieve a more natural look. I was also given a positive head start on when I started gender affirming hormones (HRT) which naturally allowed my skin to soften and smooth out. 

Of course, my basic fashion sense came into play and I was given a head start by my feminine preferences in clothes. Growing up, I had always admired all girls, tomboys and all. They were the women who were able to show off their so called masculine side without anyone questioning their basic gender or sexuality. While I had to play the same old male game of never showing a softer side. I took it in stride the best I could and later on became a big fan of women in "Boho" fashion and bell bottom jeans, In fact, I loved them so much, I was harassed at several transvestite mixers I went to when I wore my pants. Comments were why don't you wear a dress because you can wear pants anytime were common. I politely told the other attendees to mind their own business and went on about my own. 

Wearing pants before my HRT hormonal days involved extra attention given to how my hips and rear appeared in woman's clothes. Similar to so many others, I resorted to using foam rubber inserts in my panty hose to give me the illusion of hips. Depending on the top I was wearing, I pulled off the illusion fairly well without having to resort to wearing restrictive undergarments such as girdles which to me took away much of the sensory pleasure I was feeling at the time. 

I guess you can say, compared to many of the other cross dressers or transgender women I knew at the time, I went rogue in my approach to being feminine. For whatever reason, I always admired the women who could take a tomboy look and work it into a fabulous fashion statement. 

I hope I provided Jen with a little feedback on the way I feel about her never wearing heels and how much I appreciate her (along with all you others) for reading and commenting on the blog. Thank you! 


Thursday, February 8, 2024

Gender Expectations


Image from the 
Jessie  Hart

Early in my transition to a fulltime transgender woman, I thought my expectations would be relatively simple. 

My simplistic approach led me to believe achieving perfection in my knowledge of makeup and acquiring the feminine clothes would be all I would need to survive. Little did I know, when I went public with my cross dressing, I would encounter so many other issues to solve. 

Another problem I had was my cross dressing theory all  was wrong and directly backwards.  All along, I was a woman cross dressing my life away as a man, plus I had no idea how my new time as a transgender woman would put me so completely on a public stage with men and women. The time I spent trying to cross dress for my male self proved to be totally wasted for the most part. Those were the days of trying to dress sexy and failing miserably. 

As with any female who grows into womanhood (all don't), I needed to learn to play in the girls sandbox. As I came closer to perfecting my appearance the best I could, each time I thought I reached a milestone, I found there were many more to come to achieve my goals of living my own version of womanhood. Even though I may not be the prettiest girl in the room, I still could rely on other aspects of my personality to succeed. Similar to any other woman I had met in my life. Like my transgender friend Racquel told me I passed the public out of sheer willpower. I was just being the authentic me.

One part of the entire coming out process which really intimidated me was how I needed to present differently to each binary gender. As I always mention, men had the tendency to steer clear of me and women had a tendency in their own ways to challenge me. Communication in the world to survive became key to me. As far as men went, I think there were very few who were secure enough in their own masculinity to approach me. Plus, since early on I was usually alone, I would try my best to give the impression someone else was coming to join me. One of my favorite "props" was my cell phone. I used it to act as if a friend was on the way and I was saving a seat where ever I was. Then, when I did develop a small group of women friends, I did my best to blend in and not stand out of the crowd so to speak. 

Through it all, I can't write enough on how insecure I felt for years in public when I first came out into the world. When I couldn't wear my sunglasses to judge the public's reaction to me, I tried to perfect my peripheral vision to see the best I could if I was creating an impact by just being my authentic gender self. The whole process turned out to be a multi-layered experience. Similar to what my second wife told me about absorbing the life skills women need to survive. For years I was na├»ve and didn't understand what she meant since I had literally obsessed studying the world of women around me I so admired. I never considered all the ramifications of coming out as a transgender woman would mean. 

Once I did discover my truth, I did have others around me to assist in my journey. Together they all helped to make my expectations more realistic and achievable.      

Wednesday, February 7, 2024

Catching the Trolley


The Trolley Stop, Dayton, Ohio

Since one of my college degrees is in History, I always have been a fan of historical restoration.

When I was considering my male to female gender transition, a portion of the baggage I was looking at bringing along was my love of history. All the way to the point of where I lived, an 1860's brick building I restored myself in my home town. To do it, I taught myself many of the basics of plumbing and electricity. 

One of my inspirations in my restoration was in close by Dayton, Ohio in a area known as the "Oregon District". Home to many beautiful Victorian homes. Included in the many residences was a commercial strip of businesses along a brick street which had been there for years and years. Plus, it just so happened, many of them were old taverns. 

I know I write often about my fondness for going to the large sports bars when I transitioned since they provided me with a more pleasurable experience than the local gay bars did. While it's true I did go to the sports venues quite a bit, there was another place I went to also. It was called the "Trolley Stop" located on the strip I was telling you about in the Oregon District. The "Stop's" building was constructed in 1839 and is believed to be the oldest continually operating tavern in Dayton. As well as being known for it's drinks, the kitchen features cooking made from scratch. 

Since I was a customer before I transitioned, I knew what to expect and thought with a little work I could be accepted at the "Trolley" without much problem. I was right and in no time at all, I became a regular with one of the fulltime bartenders. With that accomplished, I was awarded with restroom privileges and others in the tavern being nice to me. I rarely had any problems. I could enjoy two of my passions, history and living a life as a transgender woman. 

My fondness for the venue grew except for the fact the restrooms were upstairs and when I consumed a few cocktails, navigating the steps became quite the challenge for me in my heels. Until I quit wearing them when I knew I was going to the "Trolley." 

Along the way, I ended up meeting my small group of friends there. Including my transgender friend Racquel. To the casual observer, I am sure we seemed to be quite the group. On occasion also, the venue hosted lesbian mixers which were always quite fun for me. In fact on several occasions I was able to steal a kiss from an admiring lesbian woman. 

Now, since I moved fairly far away to Cincinnati from the Dayton area where I lived, I have not been back to the "Trolley Stop" for years. Hopefully the venue and all it's fond memories will out live me. 

Tuesday, February 6, 2024

Never Give Up

Image from Amin Rk 
on Unsplash

 Similar to so many transgender women or men, I live a fragile existence. Or I should say for the most part I lived a fragile life as a cross dresser.

These were the times I was fighting totally any feelings of being feminine. Naturally, my ingrained male self fought the entire idea completely. Several times when I was caught cross dressing in front of the mirror, I gave up and decided to "purge" (or throw out)  almost all of my feminine belongings. I say almost because every time I stopped purging, I stopped just short of throwing out my favorite wigs or dresses. I guess deep down inside I knew I would need the clothes or wigs again. And I did because I never gave up on my dream to live as a fulltime transgender woman. 

By never giving up, I had several obstacles to overcome along my gender path. Everyone goes through tough times in their lives and looking ahead, I could see many more on my horizon. Mainly because, I was far from a natural when I looked at myself in the mirror. How could I ever turn a rather gruff bearded overweight man into a presentable trans woman. 

First things first. As soon as I could the beard had to go along with the weight. The first part was easy but the weight wasn't. Fortunately, I was able to cut back on a few fattening items and let my still robust male metabolism do the rest. In no time at all, I was able to lose nearly fifty pounds which helped completely in finding women's fashion in my size. At the same time, I started to concentrate on my skin. After shaving, I made sure I used a good moisturizer to aid in the process. I learned how much better my foundation looked on my face when I cared for my skin, plus by shaving daily, I was exfoliating my skin very effectively. In my case, along with practicing "extreme" shopping methods for fashion, I was able to do better in presenting my feminine self to the world. I suppose you could say, the whole process was a labor of love.

On occasion, I am amused when someone thinks my gender journey into trans womanhood was an overnight success. They never saw or understood the "error and trial" methods I went through when I first began to explore the public as a novice cross dresser or transgender woman. The most important moral to the story is I never gave up. No matter how difficult and bumpy the path became. Why? 

The easy answer is no matter how hard life became, deep down I knew what I was doing made me feel so natural. I felt if I lived long enough, I could leave my old male self behind and finally live in the world as a trans woman. 

Destiny proved me right and I was able to fit into a life in the world, I had always only dreamed of. I learned the hard way to achieve any goal in life, you never can give up.

The Gender Waltz

Image from Clarisse Meyer on UnSplash Since the beginning of time, the two binary genders have done a special dance with each other.  Being ...