Showing posts with label lesbian. Show all posts
Showing posts with label lesbian. Show all posts

Thursday, November 12, 2026

Envy or Resentment?

 

Image from Obie Fernandez
on UnSplash. 

Recently, I wrote about a few of my very unpleasant encounters with teen girls before I began to blend in with the world as a novice transgender woman and received several comments from readers saying the same thing. 


This morning however, when I went with my wife Liz on her appointment to see the vampires to have blood work done, we had enough time to stop at our favorite coffee shop for a light breakfast and a coffee drink. 


It just so happens, the coffee shop is very close to a big high school and as luck would have it, groups of teen girls were heading into the venue for a dose of their morning caffeine, so I could see what most of them were wearing. Outside of a few girls wearing short pleated skirts, most of the others were just wearing leggings and sweatshirts, so there was not much to look at.


Even still, I felt some of the old envy or even resentment that my teen years did not allow me to be a girl and have the chance to grow up the way they did. Perhaps it is the reason my second wife and I clashed so much when it came to her telling me I did not have the knowledge or the background to be a woman and what could I say? She was right. I was always on the other side of the gender fence looking in. Not by choice but by destiny had put me in a male box I could not get out of and this morning I was stuck watching groups of teen girls living life like I always wanted to do,


I guess, when it comes right down to it, the difference between envy and resentment is just semantics and my second wife telling me I could never cross the gender border to go through what a woman does was true. There was no way I could reclaim my early years of life as a confused teen boy wanting into the feminine world I could only dream of, so I would have to build my own. Many of the negatives of growing up female I would certainly have not had to do such as the build up of female hormones which I would have easily traded for my unwanted effects of male puberty. I would have taken a girl's soft curves over the hard angles I received from male puberty. 


Of course, there are other negative aspects of being a woman such as periods and dealing with the drama of men I would never have to put up with. There are simply tradeoffs between both binary genders which we have to deal with. No one gets out alive. 


Getting back to today, at least this morning, I was not close enough to any of the girls to get into any potential abuse. Plus, they all seemed to be in their own world enough not to mention me. Of course, back in the day, that is when I thought none of the girls would notice me then and I was wrong. When one did, they all did it seemed. 


Even though I can never replace the years I lost by never having the chance to live an early life as a girl, I have tried to make up for it in my later years. To share any wisdom, I had learned as a male and use it towards building blocks for my future. Now it doesn’t matter how much resentment or envy I ever felt because today and tomorrow is all that matters. I just have to put my past male life behind me and move on because the scars from my past life as a novice trans woman have almost all healed. Even the resentment for what I never had. 


It is a short post today because I have been busy, but thanks for reading along anyhow!

Comments and claps are always appreciated!


Wednesday, November 11, 2026

A Hot Mess on Another Veterans Day

Image from Tim Mossholder
on UnSplash.

Before I get started on my main post, I would like to take a moment and salute all the members of the population of this country (US) who have served in the military forces. Thank you for your service. On top of the many gender conflicted men and women who served their country so well and later came out into the world, I have always suspected there are still far too many who are still in their closets waiting for their chance to join the world. With the positive election we had, all your chances to come out may just have improved. At least,  I hope so.


As far as my time in the military went, the hot mess part mainly came during the years I waited to see if I was going to see the Vietnam War up close and personal all the way to figuring out what I was going to do about the draft, if the long, drawn-out war was still going on through my high school and college years. During those confused years, my life was a hot mess as I thought about what I was going to do about my two main pleasures in life, my cross-dressing and my beginnings of having a solid commercial radio DJ career. Since I knew my love for cross-dressing would have to be put on hold in the Army, I hoped that somehow, I could maintain my career as a broadcaster in the service. 


I started my search by going around to all the military branch recruiters to learn if they had any job listings for what I was looking for at all and learned only one did and that was the Army and it was exceedingly difficult to get into.The only thing I had going for me at that time was that the radio station I worked at was owned by a powerful congressman, so I hoped that I could use him to my advantage. I wrote and sent off a letter to Washington saying I would serve my country and was there anyway they could help me salvage my career while I served. To my amazement, in a relatively short amount of time, I received a letter back saying they would put me in contact with an officer they dealt with in the Pentagon and for me to deal with him. The power of having a congressman behind worked for me again as the officer in the Pentagon said he would look into it as well as other jobs doing attache work in embassies around the world. Which was not what I wanted, but better than the alternative.


Then I needed to be on hold until I went to infantry Army basic training like everyone else. I was able to put off going as I went on a six-month delay program to let my sources work on my future, even though, I kept telling myself I was going to put myself on some sort of a physical training program before I left, I never made it and was just a hot mess of drinking and self-pity as I faced my military future. Before I knew it, my time had passed and I was headed to Ft.Knox, Kentucky for basic training in the middle of winter. On my way, I learned I was far from being the worst hot mess on the bus we were traveling on as one of the guys in front of me was openly crying out loud. As for me, I could not wait to get off the bus and get started on the next three years of my life. 


It was not until about three weeks into basic that the attitude by the drill sergeants started to change towards me. I was very naive at the time and did not put together the fact I was receiving mail from the House of Representatives and the Pentagon and all of the sudden I was made a squad leader. A position normally reserved for those troops who performed the best at physical training and marksmanship. Neither of which described me. I finally woke up to the fact that no one was reading my mail, but someone was certainly noticing it and my hot mess of a life in basic began to calm down because it was beginning to look like I would get the impossible job in the Army I had hoped for. In fact, there were only sixty plus openings in the entire Army available at any one time. 


The rest of my three years in the military turned out to be a blur as I worked on AFRTS military radio and television stations in Thailand and Germany. It was not until I was discharged did my life revert back to the old hot mess it had always been because of my gender dysphoria. I got out of the Army about six months ahead of my future first wife and I was so conflicted about who I was that I was seriously considering meeting her at the airport dressed as my authentic feminine self but I did not and life went on as I began to try to outrun my gender issues. In the next decade, I tried changing everything from wives to jobs to locales to try to outrun myself which did not work. I was doomed to be a hot mess until I faced the reality of who I was. I was not a woman trapped in a man' s body. I had always been a woman cross-dressed as a man. 


Finally, I faced reality and my hot mess of a life straightened right up. I learned to appreciate what life had given me over the years and I had no right to deny what it was showing me to live. More importantly, I was ready to share my wisdom with the world if anyone was in need of it because I certainly did not want anyone else to go through what I went through. That is why I write.


If you are facing a mess with the gender in your life, I hope everything becomes better for you and you are able to face your own reality better than I was. Once again, thanks to all you veterans for your service. Comments are always welcome!


 

Sunday, October 11, 2026

A Destination or a Retreat into Trans Womanhood


Image from Brian Wangenheim
on UnSplash. 

As a youth, all I did when I failed at a male task was to seek the reassuring feelings of my feminine clothes and makeup. I knew then I would not have the male world I hated for a while.

The pattern continued with me into adulthood and was even expanded to include a better sense of wardrobe and makeup as I ventured into the world. But then it started to slowly reverse as I started to blend in with the ciswomen around me. Increasingly, I was feeling better about the progress I was making as a serious cross-dresser and wanted to do more as I moved towards being a transgender woman in my mind. Even though I was still extremely lonely as my feminine self, I was starting to embrace the unique person that I was. Afterall, how many people get to experience both sides of the primary genders in their lives.

On occasion, I even reverted to appreciating all the male privileges I had learned after a particularly brutal day of exploring the world of cross-dressing. Early on there were many I needed to go through as I continued to pay my dues to get to my dream of possibly living my life as a transfeminine person. Not a man.

Even though mixing genders was beginning to have a bit of normalcy for me, I came to the point where I would not recommend the journey to just anyone who was not totally committed to it. My mental health, which was already frail at the time, did not take easily to the journey ahead and it suffered. Again, sending me back to the comparative safety of the only other life I had learned to live successfully when I was competing as a man in the world.  At that point, it was difficult to tell if I was on a trans destination or a male retreat. The only thing that kept me going down my path was the deep sense of satisfaction or gender euphoria I felt when everything was going better when I interacted with the world as my true authentic self. Free and out of the closet for a change.

It took me years of experimentation in public, as I set up my own personal bucket list of what I perceived to be the real-world ciswomen had to face in their lives. I figured out why I would want to go there if I could not make it. In other words, I kept challenging my feminine self to do more and more such as do more than just spend very little time in public just walking around or shopping in easy venues such as women’s clothing stores where your money overcomes any reaction to your possible gender when it came to testing myself. I certainly then was setting myself up for a possible transgender destination in my life as I worked my way through my bucket list.

As with anything else in life, all I had learned about being in the world was not all positive and I found myself deeper into my quest to cross the gender border and complete my male to female femininization project. I learned the hard way to try to not get myself into questionable safety situations that women know not to get into that do not bother men. It seemed the gender universe was testing me on certain nights such as the one I needed to fend off negative advances from a much bigger cross-dresser admirer at a party I was at with the help of my second wife. Something I never bargained for as I went around a blind corner on my gender path. It was easier to think about erasing all my male privileges such as safety but harder to learn what to replace them with.

I do not think I ever did replace my new lack of intelligence with the cismen I interacted with as I was mansplained more times than I cared to remember by men of questionable intellect. Such as the tow truck driver I was forced into a conversation with one night when he was towing my car home. I had to sit there, and act interested when he had to tell me all the workings of his truck. Like I cared when all I wanted was to get home safe and sound. Which I did. All the bucket lists in the world did not prepare me for the reality of living a feminine life, but even still, I was loving everything I learned behind the gender curtain. If I was ever a girl scout, I would earn merit badges like what to do if your car breaks down when you are by yourself and the first person who stops to help is a sheriff. Who would not listen to me when I was trying to explain to him and the tow driver the easiest way to my house. I finally just gave up.

It soon was becoming obvious to me that I was no longer retreating behind my dresses and makeup to cover any vestiges of a male life I wanted to cover up. Instead, my full-fledged female life was a complete destination. A destination I wanted to do more than anything I ever had done in my life. There would be no more retreating back to my male world. No matter how easy it would have been to do it because he had always kept a comfortable home for me if I ever wanted to return. Much to his disappointment, I continued my feminine destination into the world of HRT gender affirming hormones which separated me farther from ever hiding again in my old unwanted male world.

HRT was certainly the end for any thoughts of ever returning to my old male self because I felt to increasingly natural when I took them. It was as if my body was telling me what took so long as my external self-synced up with the woman, I always saw myself to be. It just took me years to get there. Which was the tragic result of me not listening to myself.

Thanks for reading along on a few of my trials and tribulations of my gender journey. I hope yours is much smoother. Any comments are always appreciated.

 

 

Tuesday, October 6, 2026

Not Just a Visitor

 

JJ Hart from my Parttime Life.

When I began cross-dressing at a very early age, I learned I was so much more than a casual visitor to my femininity.

I knew because the feelings of wanting to be a girl just did not go away when the clothes came off and I needed to quickly return to my old male world. I was very resentful that I needed to return to being male because I had no choice in the matter to do it. Nothing seemed to help the way I felt except planning for the next time I could be alone and be the feminine person I wanted to be.

As I grew up, I did not grow away from my feminine instincts and desires, I grew into them and decided to gather the courage and leave my closet to see if I could make it in a world of ciswomen where I always wanted to be. Sure, I was scared when I first faced the world, but it was a natural progression for me if I was ever going to make it to my dream of living a transfeminine life. Following the initial clownish attempts, I made to present myself to the world, I settled in and learned how to present myself properly in a world dominated by the very women that I had put up on a pedestal early in my life.

Ironically, the two women that I chose to be my primary role models were the two women who tried to stop my transition the most. The first was my mom who was a very dedicated and popular schoolteacher who ran a very successful male dominated family from behind the scenes. Long before she passed away when I got out of the Army, I sat down with her and told her of my desire to be a woman. She quickly rejected me and said she would pay for a trip to a psychiatrist. Which was exactly what I did not want to hear because recently I had come out to a very small group of friends in the Army that I was a transvestite and was accepted. There was no way I was going to let mom push me back in the closet, so we never mentioned the subject again.

My second wife presented me with an entirely different challenge to my identity. She knew from the start of our relationship I was a cross-dresser but soundly rejected any ideas of me going forward into the transgender world of women. I had to respect her promise that she did not sign up to live with another woman, and it was the cause of many fights over our twenty-five years of marriage before she suddenly passed away. Regardless of all the negative feedback I received from both of them, I learned close up what it meant to be a strong independent woman in the world. While at the same time maintaining a family relationship. If I could ever be half the woman, they were, I could be successful.

Now, let's get back to that darn pedestal I put women up on for as long as I did. It took me years of trying to cross the gender border and being allowed to experience what was going on in the girls’ sandbox to do it. But when I did, I was finally able to destroy what was left of the pedestal I had built so many years before. When I was out in the world as a transgender woman, I learned the separate paths that cismen and women take. Since I had already learned the hard way about the male path, my next big challenge was to adapt it to the strong feminine world I was trying to survive in. One of the main things I learned was once you were out of the men’s club you were totally out for being a traitor and not following the fragile rules that men had set up over the years. Especially the ones that included any reference to their sexuality.

Women, on the other hand, were much more sympathetic to my cause. All the way to guiding me into women only spaces. There were very few times when I was completely rejected by ciswomen as I tried to be in their world. Probably the biggest reasons were they were curious about what I wanted there, and I was not up to no good as I was just being my authentic self all the time. Much more than being a part-time visitor. I knew from my experience as a man that women were much more in tune for BS from the world than men and embraced me when I did not have any of that negative aura around me as I was just the true me. Which I had taken years to experience.

It is no surprise to me that some think I am not trans enough to write about my experiences because I have never gone through any of the major gender realignment surgeries. Long ago when I could not afford any of the major surgeries, I decided I could live without them because my gender was between the ears and not between the legs. So, I set out to discover the best I could do to still live a complete life in a world of ciswomen everywhere. I ended up putting years into my pursuit of learning a new life, but all the work was worth it because I was able to carve out a new feminine life from the remints of a successful male life. Proving I was so much more in the world than just a part-time visitor into the world of women was certainly a challenge but with help I was able to do it.

I had the fork in the path long ago, when I had to decide to end my part-time infatuation with being a girl into the fulltime version of living the dream that I always wanted. Then I put my two and two together and hit the jackpot. I ended up winning my own personal lottery by finally listening to myself and doing the right thing.

Thanks for reading along! Any comments are always welcome!

 

 

Thursday, October 1, 2026

Like the Bulb which Refused to Go Out

 

Image from Christian Dubovan
on UnSplash.
 

Years ago in another life, I bought a small corner tavern in an 1860’s era brick building in my hometown with a friend of mine.

My dad aptly called the bar the place flies did not have to stop when they flew through and I had to agree. But his criticism did not stop my friend and I from trying to make it the best tavern we could. When we were bored, we started to look around in all the saved junk that ancient bars accumulated and found a vintage, part wooden beer sign we could not wait to put up, even though that brand of beer did not exist anymore.

Amazingly, the sign had an ancient filament light bulb that still worked, so we used it and it kept on working for years. Later, I began to think of that bulb and how it could describe my gender conflicted life. No matter how hard I tried, my inner gender feminine light just would not go out. Not even a three-year stint away in the Army from the external expression of me being a cross-dresser could put it out. In addition, when I was honorably discharged, I found I needed to replace my inner gender bulbs with ones of a greater wattage to illuminate my dark, lonely closet.

Brighter bulbs helped to illuminate my feminine image in my closet mirror and helped me improve my makeup art as well as determine what clothes would be the right ones to wear. My new visions of myself helped me to speed up the cross-dressing experience and I just wanted to have more. That is when I began to take chances by going out into the malls and shopping centers close to my home. It did not make matters any easier as I learned how far I needed to go to successfully blend in with the ciswomen around me. Instead of displaying a small/dim bulb to succeed, to get to where I wanted to go, I needed a brighter bulb to display myself if I was ever going to make it as a successful transgender woman

At first, I was just using my light to interact with clerks and salespersons until I built up my confidence to do more. I was moving past my early days of Halloween exposure to the world as a trans woman and I was scared to death because for once I did not have the, “well I am wearing a costume” excuse to fall back on if I experienced any pushback for my cross-dressing in public. I was not up to no good, all I wanted was for my light to shine brightly in the new exciting world I was in. Unfortunately, in my early years, you might say I was a dimwit when my light bulb flickered and I thought it was going to go out. Those were the dark days of “purging” or getting rid of almost all of my feminine belongings and pledging to myself that I was going to turn the light off for good, put it all behind me and go back to where I was as a successful man.

As I said, those were the days of being a dimwit because deep down I knew I needed that feminine bulb to survive. No matter how dim it was at the time. Ironically, every time I “purged” I discovered very quickly I would need a much brighter bulb to sustain my life when I returned to my gender reality. Then I started to work hard to see what my new reflection in the world really was as a transfeminine person. I had to be constantly on my toes with my best behavior to do it as I was learning so much from every woman or the rare cisman I interacted with. It seemed as if I had to keep a constant supply of new bulbs handy every time I went out in the world. I always mention the stripping of all my male privileges as the main way which drastically dimmed my new light as a trans woman until I could replace the privileges with the whole new euphoria of being able to exist equally as myself in the girls ‘club I so desperately wanted admission into. It finally became evident to me; to be admitted, I had to find a bigger, better bulb to improve my overall presentation. So, I would never have to start all over again with my feminine life.

After years of experimentation and trying, I made it into the girls’ club where I always should have been in my life. And I put all those years of replacing bulbs behind me. Suddenly, my gender path became well lit like a large city street which I was able to navigate easily. With the help of powerful/magical HRT gender affirming hormones which helped me sync my external selves with my feminine inner self. I really became a whole person with all the gender benefits I had ever dreamed of. My emotions became clearer as I became more sensitive to the world. Among with the usual changes in hair on my head and breast size to my chest. Probably, most importantly, I was able to quit trying so hard with my makeup as my skin softened along my facial angles which made me more passable as a transgender woman. The world questioned me less, so I was able to change out fewer bulbs as I continued to play in the girls’ sandbox for the first time in my life.

The only regret I have is that it took me so long to follow my feminine destiny and live out my truth in life. I wasted too much time and money cross-dressing my life away changing gender bulbs until I got it right. I should have taken the time to write down somewhere the number of excuses I heard from my male self why I should ignore my truth and not try to live a life as a transgender woman. But I did not and the only thing I can fall back on is when my male life was good, it was very good and very bad when it was not. It is the only excuse I have to waste all those bulbs I did over the decades of gender experimentation I did to arrive at my destiny.

Hopefully, you can do the same. Thanks for reading and comments are always welcome!

 

 

 

 

Tuesday, September 29, 2026

How Difficult Could it Be?

 

JJ Hart

When I started my transgender journey, I was very naïve and I kept thinking how hard it could be to stay on my path.

All I saw was the good side of being feminine with all the girls around me in their pretty clothes and long hair when I was stuck in all the restrictive, boring male clothes and very short haircuts. To make matters even worse, I needed to make sure I kept all of my cross-dressing activities very hidden from the family and friends who would have ridiculed me and called me a sissy boy. The worst thing I could be called in my very male dominated family.

As I said, I was naïve and for years thought that all I wanted from being feminine was looking like a woman, so I obsessed about it night and day. Eventually, I did come closer to achieving my goal while all the ignoring harassing comments from my second wife who rarely wore any makeup at all. On the rare occasions she went out with me, she constantly thought I was going too far with my makeup and hair to the point of calling me the “Princess”. When all I was doing was trying to blend in with the ciswomen around me by overcoming my old male self.  Of course, I felt the criticism was not fair and the evening was ruined. Often before it even got started. From that point forward, the fights started because she did not like the trans woman I was becoming. And I did not understand why.

I think now that she thought I had not paid my dues as a woman yet to claim the socialization title and she was right. I was still stubborn and did not know how I ever was going to have the chance to play in the girls’ sandbox if I did not want it bad enough. I was stuck between two massive changes in my life which would either involve giving up the woman that I loved for one that I was learning to love. How hard life could be was becoming a reality for me like a boulder rolling down a cliff directly at me. It was quickly becoming unbearably hard when I discovered I could indeed see a path ahead of living my life as a transfeminine person.

What happened next was that I began to step away from my wife and essentially live the life she challenged me to live. That is to begin to socialize myself as a transgender woman in the world. I started to meet strangers as a trans woman who never knew me as a man and start all over in a new life. How hard could it be? It was and the whole process scared me to death. I was terrified of being stripped of all my old male privileges and having nowhere to turn if something negative happened to me. How would I be able to react to potentially negative situations in my new life. It turned out I did not have many potentially negative problems, and I was able to grow into my new feminine person with very few problems because most of the world did not care what gender I was. They were too wrapped up in their own worlds. Especially the cismen who were so afraid of their fragile sexuality that they left me alone. Which was fine by me, since I had always had a problem with making friends with other men when I was trying to be one anyhow.

Ciswomen, on the other hand, were much more willing to let me in their worlds and even show me around. Making it less hard to be one of them as I was learning daily how to fill out my life. I always had enjoyed being around women and found I even enjoyed it more when I was made a member in good standing of the girls’ club. Being in the club entitled me to use women’ only spaces such as restrooms which made my life so much easier also.

Most likely, I made some male to female transition issues more difficult than they should have been. Such as when I first came out into the world and thought everyone was looking at me, when they were not. I even went as far as to wear a favorite pair of sunglasses I had to see if anyone was staring at me without them knowing it. They were not, I was relieved and was able to go on with my new life. With new confidence I never had before. Maybe I could achieve my dream after all. It was a scary thought because then I had to start to think about what I was going do with all the excess male baggage I had built up over the years when I was trying my best to hide my true self by being a successful man.

The entire focus of my life changed as I began to consider the new and exciting reality of being able to live out my dream I had wanted since I was a child. I was sad when I could not tell the truth when an adult asked me what I wanted to be when I grew up and I could not say a woman and earn a quick trip to therapy by my parents. At the time, being a woman seemed as far away to me as being a lawyer or a doctor. But at the same time, a dream I really wanted to live.

Along the way, two things were evident to me. One of which was every time I achieved a goal on my path, another would appear for me to consider doing. And the second thing was, every time I began to doubt myself, I would start to feel natural about my journey and it would re-energize me, so I could move forward again. Forward was always good and made me feel better about my life which brings me back to my original point of how hard it could be to cross the gender border. Exceedingly difficult at times to be sure, but excitingly natural as I was doing it.

Wherever you are on your path to a better tomorrow, I hope you can discover your truth and make it in one piece. As always, thank you for reading and comments are always appreciated!

 

Sunday, September 27, 2026

Buckle Up....It's the Transgender Law

 

Image from Milada Vigerova
on UnSplash.


As any of you transgender women or transgender men already know, it’s time for you to buckle up for a rough and bumpy ride along the way. To coin a term used in Ohio commercials, “Buckle up, It’s the Law”. To which I added, it is the transgender law.

It all begins early in life when we learn we have gender issues to work out of. Then we must go through the cruel reality which fully sends us into masculine bodies we wanted nothing to do with. Or the opposite for trans men. In my case, I had no need for all the muscles, angles and hair my body was adding, but there they were and I had to buckle up for a lifetime of sometimes unpleasant experiences.

Adding to the problems, many of will not survive puberty as femininized boys or masculine girls but at least the “tomboy” label can get girls by. When they want to play with the boys, which is frowned upon if you are a boy wanting to play with the girls. In my case, I remember Christmas when I wanted a baby doll and received a BB Gun instead. Hear I was stuck in a life I never wanted. I had to buckle down to change it more than anything else I ever wanted to do.

Not being a feminine boy worked wonders for me as a boy around the bullies at school but was a difficult pill to swallow during my early days of trying to look like a pretty girl in the mirror at home. Back then, I could have never imagined all the work I would have to put in to shake my male external image. It would be so much more than just learning to apply cosmetics correctly or finding a feminine wardrobe which would fit me.

What I started to do was take better care of my skin by using good moisteners I could sneak past my wife and then started a crash diet in which I used to buy better fitting clothes in the thrift stores I was haunting, looking for bargains. It worked because I began to be able to present more effectively in the shopping malls I was going to. Which I never thought I could earlier when I was laughed out of them. By then, society was changing or I was because the teen girls who used to harass me began to leave me alone. But only when I was able to femininize myself to the point of almost blending in with the rest of the ciswomen I encountered. I considered it step one to achieve if I was ever able to make it to my goal of being a functional transfeminine person. Or, I had to at least look the part the best I could. It turned out that was going to be the easy part for me and I had better buckle up for what was coming up ahead for me.

Step two it turned out was going to be the longest step I would have to take, as I finally entered the world as a trans woman and started working for my future. Following several false starts and in-advised adventures. By ill-advised, I mean the nights I was asked to leave several redneck venues I went to just to see if I could. I did not make it and got asked to leave, which I did with no incident as I continued to settle into a life I respected, and it respected me as I began to carve out a new existence. The only way I did make it through this step was to consider every failure as a learning experience to never try again. I was fortunate that several of my experiences turned out to be potentially dangerous situations that a ciswoman would know from experience to try to stay away from. Such as dark city streets late at night and huge cross-dresser toxic admirers in small hallways at a party I was at.

During stage two, it would have been certainly better to learn from what ciswomen told me than trying to find out for myself. It was all part of my effort to see if I really wanted to step aside from all the male privileges I had learned and start all over across the gender border to find out if the grass was greener on the feminine side. Which is what stage three would teach me, as I had to buckle up for the first time in my life for circumstances beyond my control such as death and dying around me. For some reason, I had always thought I would be the first to die because of the destructive lifestyle I was leading but I was very wrong.

Death and dying meant that my wife of twenty-five years along with four close friends all would pass away ahead of me with a short two-to-three-year span. Knocking me into a deep depression, and a battle with loneliness. I had gone from being a very shy person in my early life to being a very social one and I did not want to go back. But the problem was, I had never had an easy time making friends with other men as a man, how would I ever do it as a woman. The answer was quite easy when I began to live it. I found I naturally interacted with women much easier once I was playing in their sandbox, and I became very social again. Which in turn brought out more of my feminine self but first, I had to summon the courage to buckle up and put myself out into the world.

It all worked for me and took me to stage four in my life. The stage where all my challenges seemed to disappear temporally. Many times, life still caught up with me, and I had to do my best to stifle my old male urges. But them again there were still many parts of my male life I needed to bring with me. I could not live for half a century without doing so. I guess you could compare my stage four to a giant-sized kitchen mixer when I needed desperately to turn out a quality product.

It was certainly never easy to buckle down and live a radical new life as a transgender woman for me. It was especially difficult to do since I was very much an easy-going person and learning about a new life was an interesting experience. If I was going to give any advice, I would say expect a dose of the worst and embrace the doses of the other. One way or another buckle up for your new life.

 

 

 

Saturday, September 26, 2026

A Gender Yo-Yo

 

Image from Eric Prusak
on UnSplash. 
I have felt most of my life like I was a gender yo-yo. One day I was a boy and the next day I was a girl was the way I was living, and it was no fun. The ups and downs were killing me as it did in the future as I tried many self-destructive attempts.  Luckily, they failed.

Of course, my male self-received all the benefits since he was given all the advantages as I was born male and could do nothing about it. He got all the accolades when he did something right at home while at the same time, my feminine self-needed to remain firmly hidden away. Which did nothing to relieve the yo-yo gender life I was living.

Then, there were the vivid dreams I was having where I was the pretty girl. Sadly, I had to wake up to no changes in my everyday male world of having to compete daily with the rest of the male world I was in. It never changed so I was stuck and I could not go live in the world of women where I always wanted to be.  The yo-yo never seemed to slow down as life went by me, but I can say I did l learn to adjust to its up and down rhythms. As I began to understand what gender euphoria meant to me and how long it would last once it was over. The answer was a maximum of four to five days before the depression of not being an active participant in my own transfeminine life would set in and I would have to get creative and do something before my gender yo-yo hit the floor.

To counteract my depression, I began to research the meager amount of information I could find on gender issues way back then. The only term I could find was gender dysphoria which was labeled as a mental illness. So, I rejected it. All I knew was I was confused still if I was totally a male or a female. If the term had been popular back, then I have used gender fluid for awhile to describe myself. At least it would have worked until I began to run out of male fluid altogether. Since I did not have the mental willpower to find my gender fluid leak, I concentrated on keeping track of my feminine side. As I became a regular at LGBTQ diverse parties close to where I lived. It was like going to one of those quick oil change places where I could rejuvenate my feminine self around like-minded others. From lesbians I learned shared an attraction with me to toxic cross-dresser admirers, I was able to experience and learn from them all.

On the negative side, like my yo-yo, what went up had to come down as far as my gender euphoria went. Not too long after going to the parties, I started to miss the experience and wanted to do it more. Which made me a spoiled brat when I lost my yo-yo completely and could not find it. I was learning how to live a new life where I fit in as a secure transgender woman, but I was not there yet. What all my research at the parties proved was I had just scraped the surface of where I wanted to go as a trans woman but still had not had the chance to research where I needed to go internally. The internal piece would be the hardest to do because I had learned so effectively to wall myself off from the outside world and ignore it. As I struggled to live a life as a man.

I finally had to listen to the world and discover my internal piece was the biggest part of my second wife saying I made a terrible woman. Because I did before I was in the unique position to remake myself. Maybe in many ways, I was a clueless person all together and that would have to change before I could ever move forward into a better world. I had the chance to take what I learned in a male world and build a solid female world was a chance I just had to take. I needed to take a new approach and put the imbedded emotions of my yo-yo aside. It helped me with all the ups and downs I was feeling specifically with my mental health. I finally had to face the truth about myself and freed me up to be me as I always say.

If the truth be known, I was never any good with my yo-yo anyhow. My male-equated hand-eye coordination stopped me from doing more. Maybe it was my fault because I was always so biased about being male at all. Through all the ups, downs and sideways, I knew I could not take it anymore. It was time to take a time out from him and learn what life would be like of I took the transgender plunge. Was I risking all that I had earned to live my dream or not. I thought I would be fine after all the research in the world I did but I needed to make sure. What I discovered was I did not care for good about the risks I was about to take. As I said, I had put that old yo-yo away for good.

Hopefully you have been able to put that yo-yo of yours away too. It is certainly no fun to do it. Thanks for reading and commenting.

 


Sunday, September 20, 2026

Where Do We Go From Here?

 

Image from Shifazz Shamoon
on UnSplash. 


Typically, as we follow our winding gender journeys as transgender women or transgender men, we reach points where we must decide what we are going to do next.

It is especially intimidating to see all the political anti-transgender ads on TV funded by far away billionaires such as Theil and Musk who are pouring millions into defeating Democratic candidates here in my native Ohio. Especially the ones stating that the Democrats are extremists who supported sex change surgeries for children in school. That is about as far as I want to go politically in this post, so I will move on to what really matters…each of us and how we feel.

If the so called “civilians” in our world knew what we have to go through to see results in our individual gender worlds, they may understand more what it is like to be in our shoes and being constantly bombarded with negativity. Following years of struggles (or decades) I was fortunate to have found my way into discovering who the true me really was and most of the years of turmoil went away. Even still, I needed to follow a journey of steps which led me to blind curves which I knew nothing about.

All I discovered was that I had an unique life worth living to the fullest and very few other human beings can live a life which enables them to experience both sides of the binary gender road. It meant being able to exist in a life I never really wanted to live as a man. Slowly stop it altogether and start all over to earn a place like the other gender. As frustrating as that life as a trans person can be, the rewards can still be there if you can answer all the what’s next. Since most of us begin our lives cross-dressing in front of a mirror, there is plenty of ground to cover. Because we are destined to have such a small knowledge of the gender we are seeking to become. Again, because we are stuck on the outside looking in.  

Gaining access to your new life can take many paths. Sadly, many involve marriage, family and friends we do not want to give up but have to. The ways to announce your true self to the world can be done in several ways. Some just pull the band aide off, cross-dress and say here I am to the world, while others write letters and others still try to soften the blow by providing positive feedback from the internet or social media. Sometimes, I think I chose the most painful way of all as I tried to maintain my marriage to a woman I loved deeply while I knew all along that my truth was going to slip sooner or later. To make matters worse, she knew I was a cross dresser from the beginning and accepted it but told me time and time again she would draw the line at any moves I would ever make to going the transgender route and taking HRT hormones. She did not want to live with another woman. An answer I could never debate.

I guess you could say, I wanted the best of both gender worlds as I tried to do better and better in the male world I learned to survive in, while at the same time work very hard on my makeup and wardrobe to appear more realistic as a woman. All I was doing was creating severe friction within the marriage and within my head. If I was not thinking about work, I was thinking about how I could improve myself as a novice trans woman. Which I was just understanding that is what I was.

Without fail, I would get moody and nasty when I did not get my way and be able to cross-dress when I wanted which led to more friction within the marriage and more fights. In the heat of battle, my wife told me a couple of things I should have reacted to sooner. One of which would have been difficult for me to do and the other I should have been doing all along. Being called a “Terrible woman” was one thing I did not understand until I had the chance to live my truth as a transfeminine person and the other time she told me, “Why didn’t I be a man and live like a woman.” She was right, I should have done it. No matter how painful it would have been for me to carve out a new life for myself during that portion of my life when I was in my thirties.

Another problem was the sizeable male ego I was still carrying around with me. He wanted me to look and act a certain way as a novice trans woman which my wife did not like. Which led to more fights. The only revenge I ever got on her was the night she was forced to ask me for help on her makeup when we were invited to an upscale business dinner. At least the “Terrible woman” was better at makeup, I guess.

The thing it took me years to understand was that it was never about looking terrible as a woman, it was all about being socialized as a ciswoman. Sadly, my wife passed away before she could ever get to know the new improved feminine me. It took me until I was in my fifties to begin to get admission into the Girls’ Club and fully understand more about what my wife was talking about all those years before. I was suddenly on the verge of knowing where I wanted to go from that point forward. As every part of my being was telling me I was making the right decision about my life and should go for it.

I would not recommend taking the amount of time I took on my gender path before I made the final decision to live a life I always thought was going to be a dream. I think now there would have to have been a better way or like my second wife said, “Be man enough to be a woman.”  At the same time, I had my reasons for not doing it when I did which I will discuss in-depth on another post.

In the meantime, I hope you have a clearer understanding of where you want to get to in the everchanging world of trans women and trans men.

Thanks so much as always for reading along and I hope somehow, I have helped you on your gender journey. Comments are always appreciated!

 

Saturday, September 19, 2026

Is It too Early for Halloween?

 

Early fall Image
JJ Hart

As I look around the neighborhood I live in, I see people putting up their Halloween decorations already.

Then I began to think of the supposed “good old days” when about this time in September that I was starting to seriously consider what “costume” I would wear and how could I maximize its use by going to as many parties as possible. It just did not seem fair to me that I had to wait for a once-a-year party to express my feminine side without the fear of retribution. The worse that could happen to me were the other women at the party asking me who helped me with my makeup and did I really shave my legs for one night.  I was learning a valuable lesson about how curious ciswomen could be when you cross the gender highway into their lane.

Basically, my biggest decisions came as I thought about which theme I would follow year to year if I was going to the same party. And how creative could I be with my “costume” Ironically, my first big attempt at dressing feminine at a Halloween party came when I was still in the Army in Germany, when I was invited by my future wife to go to a hospital’s party. I had a couple of other wild friends who had their costumes already picked out and were coming as various forms of the male and female anatomy. So, I thought it would be an ideal time to fall from my cross-dressing wagon that I had been forced to be on for two and half years and come as a trashy prostitute.

I do not remember now how I got the clothes I needed to complete my outfit, but I was able to put together a short mini dress, long blond wig, hose and heels for a very effective costume. Since I still had approximately six months to go in the Army at the time, I was happy that no one seemed to care that I was dressed as a woman at the party.

When I was discharged from my military duty, and Halloween rolled around, I had a different challenge to face with all the newfound freedom I had. One thing I did was get away from the prostitute look and try to find a way to find a “costume” like what a ciswoman would wear.  In other words, I wanted to go to the party and try to pass as another woman enjoying herself. During the first multi-party Halloween night I went to, I think I did well. I went as one of the French girls I had seen in Paris when I was in the Army and brought the look home with me. I paired a all-black outfit which featured black tights, mini skirt and leotard with my blond wig, red lipstick and topped it all off with black flats and a black beret.

I was having a very good time entertaining myself in one of the big local clubs I went to which was having a Halloween party when a guy in a full mask approached me and simply said “I know who you are.” At first, I needed to recover from his comment before he went on to say, “I know because you look just like your mom!” Then I knew who he was and did not know whether to be flattered or not before he did not say anything else and went on his way. I did know I looked like mom but not that much.

From then on, I began to build my Halloween “costumes” from scratch and only used my many trips to thrift stores to help me with items for what I was going to wear. All I really knew was that I enjoyed my self immensely in my new world as a transgender woman and wanted to see if I could take it past the party scene and into reality. There would be other significant parties I will write about later, for now I had to learn if the build up to Halloween was totally worth it. I learned it truly was because of all the early lessons I would need to learn if I was ever going to decide to try to cross the gender border and live full-time as a transfeminine person.

I also realized that Halloween would be just the briefest thrill in what would be a long life of gender discovery. Would the overall gender euphoria of making it through the parties successfully be worth it when I had to crash back to reality and my increasingly boring male life. Plus, I found it was unbearable for me to just wait a whole other year to experience my feminine side again without me going out in public. I took my gender life into my own hands and began to explore the world in malls and outside in different venues such as bookstores which helped me build my confidence as a novice trans woman.

I went further, quicker than I ever thought I could and forever put Halloweens behind me as a necessity in life and more of a fun pursuit. In its place, I would be trying to carve out a brand-new feminine life of my own. It was the beginning of the most terrifying yet exciting time of my life. Mainly because I was stripped of all my old male protections and had to start all over again in a world where I did not know who to trust. Including myself because everything I knew was changing when I left the good old boys’ club for good and applied for membership in the girls’ club that I had so long waited to join. I was just at a point where I needed to convince ciswomen around me that I was serious and brought different qualifications to the feminine table. I had to suggest I was a woman too but just had been socialized a different way than they had been.

In many ways, Halloween was the earliest part of my socialization process thanks to the early interactions with ciswomen (and men) that I experienced. Immediately, I found that men I had known for years ignored me as a potential cross-dresser or whatever they thought I was. It did not matter. I was out of the club.  While at the same time, women I had known for years were curious about me. Lessons that had carried with me well in the learning years to come.

That is why I will forever miss the early excitement I felt around my early Halloween parties and why I still feel the fun I felt when I see the neighbors putting up their decorations early. Who knows, there may be a person in the family with gender issues also.

 

 

 

 

 

Friday, September 11, 2026

The Age of Gender Innocence

 

Image from Nicola Dowie 
on UnSplash.

I used to think that my initial days of cross-dressing were the most innocent days of my life. I was very young and the feel of the feminine clothes on my body and the expectation of seeing myself in the full-length family mirror brought me to the height of anticipation. For the moment at least, I was putting aside all the worries I had of ever being able to live successfully in a male world.

Now, with the benefit of age on my side, I wonder if I was ever so innocent. Sure, I loved all the things about being a cross-dresser such as shaving my legs and wearing panty hose, all the way to feeling all the sensations of being able to wear the same pretty clothes I had seen the girls around me wear. The biggest problem remained was that just the wearing of the clothes was never enough. The thrill I felt of dressing up was guaranteed to only last a couple of days before I could not wait to do it again. Even my young mind knew there was still something wrong.

What was wrong was I was not a cross-dresser at all; I was a transgender woman waiting her turn to live in the world. In the meantime, I would have to depend on the temporary thrills of mirror worship to get me by in life. It all set me on a very long path of gender discovery. Complete with many ups and downs along the way to make the journey either very scary or at least very interesting. It took me years of mirror living before I could ever gather the confidence I needed to finally conquer my fears and go out into the world as a novice trans woman. Of course, there were the on-going challenges of learning makeup as well as shopping for my own clothes on an extreme budget. When I discovered the thrill of shopping at thrift stores, I was able to find clothes that fit me well by having the chance to try them on before I bought them. If I made a fashion mistake when I got it home, it was not such a big deal because it did not cost that much to start with.

Rapidly, my days of gender innocence were fading away as I became more involved in the world of ciswomen. I quickly discovered their world was much more than just the external world of fashion, hair and makeup. Their world was so much more complex than a cisman’s I was not prepared for it. I found I had a lot of work to do to be accepted at all. To prove I belonged there at all, the first step was to prove I was serious about doing it. I would first have to prove to other women, I was not trying to enter their world as some sort of a dare, or that I was not up to something no good. I desperately wanted to cross the gender border and join the girls’ club and leave the men’s club forever. When I was able to, entrance behind the gender curtain opened for me like never before.

It took many times behind the curtain for my innocence to really go away. I needed to battle my paranoia with being shy to start with and then having to communicate on a whole different level before I could relax at the girl’s night’s out I was suddenly being invited to comfortably. And that was not the only one thing I needed to deal with. Such as how I would ever dress to blend with the rest of the ciswomen in the group I was invited to. I certainly did not want to embarrass myself by dressing too much or not enough and finding that special point where I blended right in. My innocence was real, since I was dealing with a world I had never been in before, but the pressure was real because I wanted to make it a success so desperately. I can compare the experience to first dates I went on with women I did not know well as a man. How would I start the conversation and what would I say.

It turned out I did not have to worry that much because the group conversation was easy to follow without men around. It flowed around family basically and the relationships the women were having with their men. I just flip-flopped my past life as a man to one of a woman. Being purposely vague about key issues such as not having the birth of my daughter but I was there when it happened. My communication efforts seemed to work with all but one woman who just glared at me. I ignored her glare and stayed in the conversation and got invited back.

As I experienced more of the world as a trans woman, the more my innocence went away. Sure, I encountered the occasional toxic woman or TERF but with my confidence level soaring I was able to handle most all of them. If you are wondering why I have not mentioned any men, it is because there were so few of them. For the most part, they knew I had left the men’s club and wanted nothing to do with me, Plus, I cannot take all the credit for my success I had a very tight knit group of women friends around me to support me too.

Perhaps the most lesson I learned about gender innocence was the amount of difference there is between the two main primary genders. Basically, I learned that men operate on some sort of a power matrix. When they are challenged, they are less likely to give you a chance unless there is something in it for them. Women, on the other hand, are much more open to the world. Especially when it comes to their sexuality, which is not as frail as a man’s.

As I always say, if you are just starting up your gender path, be prepared for a change in your innocence as you enter the world of your preferred gender. And thank you for reading along as I described mine.

 

 

Tuesday, September 8, 2026

I Wish I Knew Why

 

 

Image from Jon Tyson
on UnSplash

It has been a while since anyone has asked me when I knew I was transgender. In fact, it was several years ago when one of my grandkids was coming out to my daughter as being trans.

My daughter then asked me if I had always known, true? I told her yes that was true except in the exceedingly early days of my life when I knew something was wrong with me but I just did not know what. As I grew older and I experienced that first magical visit to mom’s clothing drawer did I truly knew what the problem was. I really liked the feel of mom’s clothes and that was only the beginning as I wanted to be a girl full-time sometime in my life. Just the buzz of wearing feminine clothes was never going to be enough. So, I set out on a long journey to see if I could ever achieve my dream.

When I was able to begin to interact with others with gender issues, I found early on that it was not going to be the end to my questions that I thought it could be. For example, I was too much girl for many of the cross-dressers I met and not enough woman for the then called transsexuals I encountered in person at the social/mixers I traveled to. The closest ones initially were nearly a two-hour drive away before mixers were then set up in a nearby central location for me. It was then that I was able to meet others who identified as true transgender women and I fit in perfectly with them. Finally, I began to have answers to my identity as a person.

Of course, I needed to take all sorts of side journeys as I sought out the key to why this transgender world had chosen me. In my research I even came across the theory that the drug “D.E.S” which was given to women with a history of problem pregnancies around the time I was born, could conceivably be linked to a person having= gender issues later in life. Because to ensure the fetus went full term in the womb, the womb was flooded with estrogen to aid the birth process. I thought “D.E.S.” might fit me because my mom had suffered through three still births before I came along. Ultimately, “D.E.S” stayed just as it started with me. Another solution to an extraordinarily complex gender problem with no concrete answers.

Then there was the victim mode I wrote so much about when I went through a poor, poor pitiful me time of my life. I could not understand why I needed to be stuck with all the gender issues I had when no one I knew had them either. To this day, I envy men who have been able to go through their lives as men without the added distraction of wanting to be a ciswoman. Finally, I made the difficult turn considering my overwhelming desire to be feminine as a good thing. Because it set me off from society as a unique person with a look at both sides of the gender border. Removing my victim mentality made all the difference in the world to me as I began to look ahead for the possibilities which laid ahead. Rather than always looking over my shoulder and dwelling on the mistakes I had made.

The more success I experienced when I first was able to carve out a new life for myself as a transfeminine person, the more the wish I knew mentality I had lived with my whole life began to fade away. From that point, I went into my confidence mode because without it, I was powerless to do anything I wanted to do as a trans woman. I found that as long as I held my head high and did my best to be a quality person in the world, the more people left me alone since humans are like sharks. They sense blood in the water, and I was not adding any of mine. Confidence also allowed me to try different things. To judge if I really wanted to jump the gender border and give up living life as a man altogether. Even though it was the most difficult decision of my life, having even a sliver of hope that I could live my dream that propelled me forward to a gender tipping point that so many ask about.

This time, I could tell anyone who asked why I decided to leave a successful male life to take on a decided uncertain one as a transgender woman. The answer I always gave was deceptively easy. I had reached my own gender tipping point where I was living more as a woman (and feeling natural doing it) and less as a man as I was feeling increasingly uncomfortable doing it. By doing as much research as I had, I had given myself no choice as what I should do. When became now and that was the time, I decided to take the next step and pursue gender affirming hormones or HRT to sync my inner mind with my external body the public saw. I knew it was the point of no return for me as my body took to the new hormones magically.

I knew from there that all my explorations as a trans woman pus the addition of HRT allowed me the most powerful female privilege of all. The power to finally be myself. The wish I knew why I was different my whole life was answered with a resounding yes, I did know it all along and refused to face my own truth. I was living a counterproductive life as I was going overboard trying to be successful as a man when I was a woman forced into her shell all the time struggling to get out. The best part was when she said I told you so, as she destroyed what was left of my old male ego.

I finished strong when my why me became a why not as I had the chance to live my feminine truth among the ciswomen of the world.

Thanks for reading along and I hope you will discover your why me in life! Comments from you are always welcomed.

 

 

 

 

Passing Privilege and Cisgender Women

Image from Sara Dabaghian  on UnSplash.   Yesterday, I went with my wife Liz to her eye doctor appointment and assumed my position as a conf...