Showing posts with label queer. Show all posts
Showing posts with label queer. Show all posts

Saturday, August 1, 2026

Living the Dream

 

Image from Randy Tarampi
on UnSplash.

I discovered before I could live a dream of living as my own unique sense of womanhood, I needed to discover exactly what that meant.

I knew very early on it was much more than just applying makeup and parading around in one of mom’s dresses. It went much deeper than that. I wanted to be a girl as badly as anything I had ever wanted in my life.

The problem was that I was stuck in an information “never-never” land with no internet or social media of any sort to provide key information on what it really meant to have issues with your gender and not just throw you aside with some sort of a mental illness diagnosis. I did know enough about myself to know I was not mentally ill for wanting to be everything feminine. So, I did the only thing I knew how, day dream my life away envying the ciswomen around me.

As I grew into myself, I learned more about my dream and the overall demands it would make upon my life. Even though I tried not too, I still added extra male baggage such as a child, marriage and a better career to my life. I always thought I would be better off lonely with just having myself to depend on if I ever had to get rid of it all in my male world and start all over again as a transgender woman. Another problem was that I was tantalizing close to encountering other gender conflicted people who were actively following their dreams, so I knew it was possible.

For example, I just missed crossing paths in my broadcasting career with other trans women who were actively following their dream. One at a small radio station I worked at in my hometown and another I ran into at a AFTN Thailand radio/tv reunion in New Orleans. Sadly, the trans woman was so shy and backwards, I could not even get her attention to say hello.

Everything changed when I came home to nearby Columbus, Ohio and was invited to very diverse small parties on a regular basis. Everyone was there, including several trans women who were headed for gender realignment surgeries that I was able to interact with and learn from. How much exactly did my dream entail? Going all the way like they did, or not was my major point of wanting to know about them. The one thing I did find out was that they had taken the time and effort to set themselves up for success in the new lives they were undertaking. One trans woman was a firefighter getting ready to retire and had a good pension and insurance coming to cover her surgery and another was a very successful electrical engineer who was extraordinarily beautiful and knew she would not have any problems continuing to work after the surgeries.

I was in neither of their classes in appearance, insurance coverage or job security to even compare myself to them, but still my dream of ever living as a transfeminine person would not go away.

Somehow, I needed to carve out my own individual gender path to success if I was ever going to make it. Finally, I learned the powerful message to just be myself and most of the rest of my problems in my male to female femininization would fade into the background. No, I was not extra attractive such as thedestiny transitioning transgender women that I knew but I realized that many of the ciswomen that I knew weren’t either. It was very shallow of me to think that all that went into to being a quality person as a woman was just appearance, so I grew past it. My focus shifted into having more confidence in myself as a good person that a stranger would like and away from just how I looked. When I did, my dream began to become a better focus. Maybe I could do it after all.

Of course, my major focus was what was I going to do with all the unwanted male baggage (and some of the wanted too) that I was planning on taking along on to my new life. At that point in time, my second wife was still alive, and she had made it a point to tell me she would never want to live with another woman, so I had to figure out what I was going to do about that major problem. Then I also had the usual conflicts we all face such as what we are going to do about employment and would any of our friends accept us.

For me, destiny came along and in one fall swoop showed me the way to living my dream. My wife passed away. Leaving me alone to consider my future about the time what was left of my close male friends died too. It turned out destiny was giving me a clean life slate to work from when I began to start all over. In addition, I was old enough to retire and work a little on the side to make ends meet and the Veterans Administration health care system which I was already a part of decided to approve gender related care or HRT for qualified veterans which I was. Destiny could not have shown me a better path to my dream than if I had planned it that way. I needed to pay my dues and work through many dark, lonely days to get to the light, but it was worth it when I did.

Finally, my dream became a focus for me when I met my future wife Liz and other ciswomen who let me into their world. I was able again to focus my dream on reality and make sure it was not a nightmare. Perhaps the best part of the entire trip up my gender path was the likelihood that I would ever make it. To say the least, my going forward was a shaky proposition to start with and all too often, my mental gender darkness threatened to catch up to me and my dream.

Thank goodness it never did, and my transgender dream became a reality.

Reality for me is also to have you join in with my thoughts. Thanks so much for doing so!

 

 

 

 

Thursday, July 30, 2026

How Much Courage did it Take You?

 

Image from Jon Tyson
on UnSplash.

Often, I hear the words courage or bravery kicked around when it came to mentioning someone coming out of their closet into the real world.

In my case, I would have to replace either of the words with just being afraid of what would happen if I did not pursue my gender dreams of living as a transgender woman. Mainly because I was so self-destructive when it came to causing self-harm to my unwanted male self. I drove too fast and recklessly, drank way too much and even tried to actively kill myself once because of my gender dysphoria.

Especially after I had the rare chance to talk to my friends who survived brutal combat in the Vietnam War, I reserved the terms brave and courage for them. Because in many ways, I was just doing what came naturally when I cross-dressed in front of the mirror at home. It turned out staying in my own little feminine world was very easy until I began to want to see if I could stretch my luck and actually leave the house looking as close as I thought I could to a pretty girl. The only reality I did know was I was scared to death.

Little by little, my fear began to subside, and I wanted to expand my explorations to bigger and better venues such as the malls which were just beginning to come into their own back in those days. Still. I didn’t think I was brave enough to do it. Or was I just being stupid by risking losing everything that I worked so hard to build up in my male life. My ego dictated that I did not dwell on the stupid aspect of trying to femininize my testosterone poisoned body. I just wanted to blend in with the rest of the ciswomen I envied so much. As much as I was being abused by certain segments of the public, I began to use another term to describe myself and that was stubborn. In fact, I think that would be a great title to a new PBS show (Public Broadcasting System) called the “Stubborn Cross-dresser.”

As I continued on my gender path towards finally being allowed to join the girls’ club, my stubbornness in trying new things was both a blessing and a curse. A prime example was when I was trying to hang on to my teen fashion sense way too long. It was a curse, and my blessing came along when I became stubborn enough to keep going back to my cross-dressing drawing board until I fixed the problem and became able to blend in better with the women, I wanted to notice me. After the death of my second wife of twenty-five years, I was desperately lonely and did not want to attempt to build another life as a man when the possibility of building one as a trans woman was right in front of me. If I was brave enough to take advantage of a life I had only dreamed of. Was I going to take the easy way out and try to be a man again or build upon what I had learned as a novice transgender woman became my major question to answer.

Finally, I needed to “man-up” and be a woman as my second wife used to tell me and when I had the courage to do it, I felt a deep happiness in life I never had before. In fact the feminine privilege I found to be the most pleasant was the fact that I was allowed the opportunity to be happy. For the first time in my life, I was able to align my sun, moon, and stars so I did not have to fight a gender battle on two fronts which kept me unhappy and on edge. I positively loved my new life along with my first chance ever to just be happy with what I had.

If you are one of the many gender conflicted individuals trying to decide if and when you will make the ultimate choice to go for the gender border as a trans woman or trans man, my only advice must be, look deeply inside yourself for your answer. Your answer is there If you are stubborn enough to find it. Life is like an old merry-go-round and often it is difficult to slow it down to see the real world spinning in front of you. And if destiny puts you on the right path to do it, you can discover a group of well-meaning friends (ciswomen or men for you trans men) who can help you along. Making you a better person than you ever thought you could be. I would never have thought that the gender dysphoria that I felt would end up causing me so many problems in my life.

Before your life ends and you move on to whatever other place of existence you believe in, you have the basic right to be happy. You can deal in semantics and call your gender journey as being brave or having courage all you want but the end result is you being the natural person who you always should have been.

Somehow, we have been chosen to lead a different life’s journey than most of the others in the human race. Call us brave or courageous if you want but as a tribe, we are doing what we were always been destined to do. It is just too bad we are met with such resistance by haters in the world. As well as the gatekeepers who want to keep us away from our chosen genders. When I speak about gatekeepers, immediately radical feminist TERFs come to mind who have no business in ours.

Best wishes on your successful gender journey and summoning enough courage (if you want to call it that) to get out into the world and live your best life.

Thanks again to all of you who join me in my experiences, and I hope we can all learn from them. I apologize to all of you who have commented. I am a little behind getting back to you because of technical problems.

 

 

 

 

 

Wednesday, July 29, 2026

Why Me???

Image from Barbara Burgess
on UnSplash. 


I have often thought during my life as I was becoming aware of who I really was as a transgender woman, why me?

Those were the days of thinking I was the only male in the world who wanted to be female, and if I was, what was I ever going to do about it. Very early on before I had the necessities to start exploring the world on my own, I needed to rely on just the occasional cross-dressing experience in front of the family’s hallway mirror. It was very difficult to do because I needed to work around a very curious brother and family.

Most certainly, for years, I played the victim as I felt sorry for myself and my gender issues. It wasn’t until I began to leave my dark, restrictive gender closet did I begin to see that I was not so much of a victim after all. Overcoming my gender dysphoria would make me a unique human being with my insight into both genders. But only if I first paid my extensive dues to get there.

As most of you know, the dues transgender women and transgender men pay to challenge and win the battle to change genders is extensive and often dearly expensive as we have to give up spouses, family, friends and jobs. Just for what some see as a selfish pursuit of personal pleasure. If they ever knew the truth, most certainly they would not feel that way as they never had to feel the anguish, we feel about hurting others. During the depth of my struggle, I was down mentally and lonely as I felt why was this all happening to me. It led me to feel selfish and there was nothing I could do about it. I was even jealous of the other cismen around me who could follow their so-called “normal” lives without worrying about something as major as wanting to be a woman.

As I continued to learn what it would take to lead a transfeminine life, the more I respected what I had discovered and wanted to learn more. That was the time I began to see the light of my victim tunnel was not the train but was sunlight which would lead me into a new day. Away from many of the old fears and paranoias about going along my continuing male to female femininization path I was traveling. Slowly I discovered there could be much more to my gender journey than just doing my best to blend in with the ciswomen in the world around me. I still did not know why me, but at least I was not a victim any longer and I just might be on to something much bigger if I could escape all my self-destructive behavior I was engaging in.

I learned the hard way from pure social experimentations that I was on the right path and to keep going. Maybe by doing so, I could climb the gender ladder up to the level of where some of my transgender mentors were. If they could make it, why couldn’t I. It wasn’t why me anymore, it was becoming why not.

I was more certain in my gender choices when questions surrounding things like my sexuality came about. Because I was immediately embraced by so many ciswomen so quickly, I never had to worry about the occasional man that came along and mainly viewed me as a fetish object The last thing I needed was having to deal with the drama of a toxic cisman. So, I never did as I was able to discover my validation as a transgender woman through other strong women. Why me became suddenly very real as I kept going out night after night with the group of mainly lesbian women who accepted me. They taught me more than they ever knew about what it was like to survive in a world where men were basically an afterthought.

In their own way, my lesbian friends helped me to be prouder of the trans person I had become. My why me became why not as I grew increasingly confident in my own skin as a transgender woman. To coin a classic song, I could see the world from both sides now and be part of a special group of humans that could. Which is why I think so many transphobes and TERF feminist gatekeepers fear us and try to keep us out of women only spaces. Like them we gained our womanhood, just from a different and unique vantage point and we are not men trying to slip in. Especially since we work so hard to get away from the male culture.

Long ago, I was able to put my why me victim mentality about being transgender behind me and get on with my life. It marked the turning point when I could be accepted into the only club I ever dreamed of being in…the girls ‘club and I never have regretted doing it. Following several not so good decisions in my life, I finally made the right one and put the necessary work in to earn the title of proud transgender woman.

Today I will put my public gender persona to the test again as I go with my wife Liz to two of her doctor’s appointments. It is usually the easiest test of all because all the people I run into are mostly concerned about themselves. Plus, these days, I normally mentally have gone back to thinking my newer transgender self has been me all along. No more victim mentality. I always point out I did not have much to work with when I started my journey except a deep will to do it. I also wonder, if I knew all the bumps and bruises, I would have along the way, would I ever attempt the trip across the gender border. It took me taking the chances to get out into the public to make it at all, and if I did not, I probably would have been in my closet crying, why me.

For the first time in my life, all I knew was I needed to get out of my closet and fight for the life I really wanted.

 

 

Monday, July 27, 2026

Staying in the Present as a Trans Woman

JJ Hart at Trans Ohio.
Staying in the present has always been a difficult task for me. Perhaps it all started when I was a very young gender distracted person and could not seem to stop daydreaming about being a pretty girl. The daydreams were nearly always a great escape from my everyday boring male world where I was always competing for the same rights to be recognized at all.

Overtime, I was rarely successful as a boy and just put in the amount of effort to get by. The only thing I was moderately successful on was hustling on my newspaper route and doing extra chores around the house to make extra money. Which in turn, I used to buy my own feminine articles such as makeup, and pantyhose for when I was able to shave my legs. Overall, my plan worked and eventually I was able to build up my own collection of cross-dressing essentials. As I discovered I could get away with shopping at a couple of small local department stores for everything I needed to shatter my dream of doing it and stepping into my own form of reality.

The older I got, the more I did not grow out of my cross-dressing gender desires. In fact, I grew into them when the world became more and more accessible to me. I was building an increasing sense of confidence in my new self and going out briefly into the world as a novice when the Vietnam War and the persistent military draft caught up with me. For the first time in my life, I could not daydream of something as major as a war going away. It was as real as my draft card. Which I resented having because none of the ciswomen around me needed one. Why should I be forced into an unfair war when they were not was what fueled my resentment. A resentment which just made me feel worse as I wasted my time worrying about the war which was staring at me in the face.

To make matters even worse was the fact my fiancé who knew I was a cross-dresser told me we would break up unless I told the draft board I was gay. Which, there was no way that was going to happen, so we did end our relationship just before I headed out to Ft. Knox, Kentucky for Army basic infantry training. Even though I fought military service as long as I could, in many ways it did me good because I needed to stay in the present most of the time when I was going through basic. If I was not, I would feel the wrath of the drill sergeants which was not a place I wanted to be. I guess you could say, I was going through a whole different basic training by teaching me to stay in the present.

After I had served my time, I tried my best to pick up where I left off by trying to join the world as a transgender woman. A new life was just starting to come to me with the realization I was much more than a part-time cross-dresser and needed to experience more of a woman’s life to satisfy me. Change was upon me with the birth of my daughter and a new wonderful world of mall shopping experiences to explore. After a rough start, I was able to present well enough to enjoy being out in the world. In other words, the teenaged girls who made me a target suddenly left me alone. The rest of the mall time was easy because I discovered that my money was green and that was more important to the store clerks who waited on me than my potential gender.

Eventually, more reality than daydreaming set in with my life. I was becoming so successful in carving out a new transfeminine life I knew that I had gone too far to ever turn around on my gender path to ever go back. Sure, I was scared but a voice in the back of my head kept telling me this was so natural that my new world deserved to be the reality I always sought and I needed to stay in the present to do it.

I discovered as a transgender woman, the present was a very great place to be. For once, I had access to the gender I wanted to be with which were all the ciswomen who showed interest in what I was trying to do in their world. I had always had a difficult time making friends with other men when I was acting like one and I finally figured out why…I should not have been in the boys’ club to begin with. Living a lie was a total mistake which should never have happened. I was not interested in a club where I never belonged, and that was OK.

Old habits are hard to break, and maybe even more so for transgender women and transgender men. Primarily because we have to decide what baggage we are taking with us or leaving behind as we journey along our gender journey paths. Bring too much, and you can’t carry it all or don’t bring enough and end up losing all of your building blocks you need for a new life are all things to consider. And most of all, it is important you stay in the present, so you don’t forget where and who you are and slide back into your old self. It is frustrating when something as small as the look on your face can destroy all that you have worked so hard to perfect. That old male “stay away” scowl may have worked in your old world but in your present one, it certainly doesn’t.

It was difficult for me to find my present. Determine if it was the right choice and then stick with it. As I went through my male to female feminization efforts, I needed to finally decide on a wig to wear on a regular basis and quit looking for the miracle wig which would instantly make me attractive. Why? Because people were starting to recognize me as a person, and I needed to build on that. Instead of just carving a new person, I was blasting one and having the time of my life doing it.

I just wish I could have stayed in the present earlier in my life, which I know would have given a better understanding of who I was at the time. I almost did more after I served my time in the Army, but it was in the mid 1970’s and the world was different, and I did not have the courage to do it. Instead, I played my status-quo cards and thought I could help my life along by just cross-dressing. By doing so, I just ended up losing so much of my life when I ignored living in the present. One way or another, it is much too late to cry over time that was wasted and remember the good time when I discovered my present and lived it.

Thanks for reading along with me. Hopefully my insights can help you with yours and comments are appreciated.

 

 

 

 

  


Sunday, July 26, 2026

Gender Affirmation Day

 

Image from Ava Sol
on UnSplash.

Recently, I had a rare opportunity to meet and enjoy the company of a small group of family for breakfast which I like to call a gender affirmation day.

Precisely, there were four of us including my daughter, son-in-law, my wife Liz and myself. For the morning, I chose a breakfast only small chain venue which we had never been able to go to before. Since it has been a while since I have seen daughter and son-in-law, I was very happy to see them. In addition, I have three grandchildren who did not come since they are adults now and have their own lives to attend too. Plus, the oldest, is a nuclear engineer and lives in Maine and the next two in age (both boys) are traveling in Japan. The youngest is some sort of a bio-engineering student at “The Ohio State University.”

Getting back to my experience, I was dressed very casual in my favorite jeans, new OSU T-shirt and comfortable tennis shoes to face the world at large in a place I had never been to at all. Plus, I did put on some light makeup and partially tied back my increasingly long hair. We were lucky enough to beat the Saturday morning breakfast rush and got a seat as the place was filling up. As I always do, I try to find out if anyone is paying any extra attention to me as Liz and I made our way to our seats. Nobody did except this pesky kid (boy) who would not stop staring at me after we sat down close to where he was sitting. Through it all, I managed to ignore him until his family finished eating and left before we did. Leaving me to completely concentrate on my food and the pleasant conversation that was going on.

As I always point out, being transgender in my daughter’s extended family is not much of an anomaly after all. The nuclear engineer in Maine is trans and my first wife (who is my daughter’s mother) has a transgender man cousin. Diversity runs in the family, whether the naysayers, which are a few, like it or not. My first wife’s in-laws are very redneck conservatives, the same as my ex-communicated brother’s. So, I have not talked to him in over a decade.

My daughter was and is one of my strongest allies and used me as an example to all three of her kids on diversity in the family. She has always been by myside during my male to female feminization journey and I love her deeply for that and how she turned my out-of-control life around when she was born. As a point of reference, she will be fifty years this year and I am trying desperately to come up with something special to do for her but she I like most all of the other ciswomen in my life, they do not have a grasp on what they did for me.

Since now, I spend so much of my time isolated from the real world and because I have mobility issues, I don’t have a chance to match wits with the public anymore and face people such as the pesky kid who would not quit staring at me. It is a good thing he was not sitting at an angle where Liz or my daughter could see him or there could have been some sort of an altercation about having manners. That would have been bad because I am used to fighting my own rare battles. As most kids do, he got bored and turned his attention back to his breakfast. Per norm, is mom was too busy on her phone to be paying any attention to her kids and at least they were not screaming.

Since my daughter’s world is so busy with work and acting as a home care person for her mom, it is difficult for us to put together the time to get together, and I can take advantage of a powerful shot of gender affirmation. Because I can still benefit from it so much and I have always been just me to her and the rest of her extended family no matter what gender I was living as. As a matter of fact, it took me longer to adjust to them accepting the authentic me than them to me. One of the reasons was because the pressure of living an unwanted life was over and I was free to be happy. They knew me better than I knew myself.

More than likely, I won’t have to wait as long as I did this time for another shot of gender affirmation from person who went through my transition with me because my daughter has access to many old pictures of my family I need for my book I am writing for them about my life. She lives in Dayton, Ohio about an hour away from where I live in Cincinnati so it’s not like we live right around the corner from each other. Plus, her big birthday is coming up on Labor Day, so perhaps we can pick up the photos then and if her mother-in-law throws a big party, there will be more gender affirmation for me to selfishly enjoy. Maybe my second wife was right, my gender struggles were all about me.

In many ways, gender affirmation is just another term for having an extended period of gender euphoria. It is just another way of saying that I need to be relieved of my transgender insecurities because they run so deep. Maybe it is because I was forced into that male box, I wanted no part of for so long yet eventually learned to master in so many ways. Or me just wanting to be a transfeminine person was so difficult for me to accomplish, I could never forget the struggle and still bear the scars from him fighting me for control.

Regardless of my insecurities, I still try to keep them hidden around my supporters and do my best to show my appreciation for the gender affirmation they have given me.

 

 

 

Wednesday, July 15, 2026

Existing in a Male World from the Perspective of a Trans Man

Image from Nicola Dowie
on UnSplash. 
 


In response to yesterday's post praising transgender men, I received a comment from “Gio”, a trans man who follows my writings and thoughts.

Here is his comment word for word on what he has gone through during his transition from female to male:

Thank you JJ for this nod. You know, they are a tough bunch, on the exterior. They are also exhausting. Try to teach them how to be a real gentleman and right out of the gate they label you a sissy. I always counter with being raised to respect and honor women. In the Italian Culture in which I was raised the women were savvy. The women in my family ran the show and they somehow left the men feeling like they were in charge. I witnessed this with my parents (first generation born in America) and my grandparents (immigrants - who escaped Mussolini; everything old becomes new again but that's another story). The Cis men I encounter, many of whom are wealthy Trump supporters, posit they own their women. She is to do what they say. A woman, if raped, deserved it because of how they acted or what they wore. It boggles my mind. So, I remind them that women are to be revered, they remain underpaid yet they have more talent than their male counterparts. I remind them that if married they took a vow to cherish and protect their wives. I could go on and on here. Suffice to say, it’s usually a bipartisan type of conversation and they often end pleasantly. Luckily, I've not been fired yet because mostly these are the people who keep me employed. I'm also amused by how they request me as their chauffeur to drive their wives and daughters. It's these little things that cause a ripple effect”. First of all, “Gio” thanks for the comment!

I really liked your insight into how exhausting men are because on the few times I went out with a man, I could not relax and be myself when I was catering to his ego. In my family growing up, we were a heavily male influenced crew but like you, mom ran the show from behind the scenes, so I learned a lot from her on how to be a woman, She is rolling over in her grave as we speak to hear of such a thing but it is true.

Fortunately, since I am retired, I don’t have to worry about working with any tRumpters and their backward gender ideas. But when I was employed, I always did my best to protect and advance the careers of the ciswomen around me. To the point of even hiring a transgender server at one of the restaurants I worked at. Sadly, I was transferred and she was fired by the next manager, but I tried to do my part.

Looking back, it was my love of sports and military service which kept me from wearing the “Sissy” tag early in my life and when I advanced as far as I did up the business ladder I was in, I understood that males form teams and I was able to benefit from that even though I detested everything I was doing most of the time when I needed to play the gender game I was in. Maybe the whole time, I was exhausted too about playing the male game and just wanted out to go to my transfeminine world. I took what my mom taught (more than dad) and was able to beat the system which was stacked against me.

When we are transgender, it is certainly a complicated world we live in when we need to go outside the confines of a so-called normal world. The old world is on its way out and hopefully a younger more progressive gender-neutral generation will power a better world. Especially for transgender men such as “Gio” who was kind enough to share his thoughts with us on his world.

 

Saturday, July 11, 2026

It's a Lonely World

 

Image from Jarle Johnasen
on UnSplash.

It is a lonely world for many transgender women and transgender men as we journey along our dark gender paths.

As I always point out, like so many of you, I got a late start on filling out my gender workbook on how I was even going to begin a transfeminine life. Before the word was even invented. I was not invited to any overnight stays with the girls I admired so much to take advantage of early make-up tips and even feminine peer pressure on the clothes I was wearing to do a better job of looking the best I could in front of the mirror. Ironically, I was probably ahead of most girls age-wise when I started wearing makeup and shaving my legs, but I did not know that because I was not allowed behind the gender curtain to play in the girls’ sandbox.  

Looking back, I thought for a while there was always a chance I was going through some sort of a phase and I just could not be the only boy in the world with a strong desire to be a woman someday.

To make matters worse, I was always exceedingly shy back in those days which made me an introvert, and I had a tendency to not trust others. That would manifest itself much later in life when I had a very difficult time making close friends. Especially with other men. Who I thought would never understand my deepest darkest secret which by then I knew was no innocent phase in life I was going through. Not surprisingly after a while, I lost most of my shyness around ciswomen and enjoyed my time with them even more. Even though my true motives were never revealed that I just wanted to be like them in the worst way possible and I was just trying to see what it took to live their lives.

Even though I was still married to a couple of very different women through this portion of my life who knew of my cross-dressing desires and did the best I could to surround myself with other women, deep down inside I was still lonely. It never occurred to me why and what I could do about it for years. I just never realized for the longest time that I was living much of my life completely backwards. I was never meant to be a man and was forced into it by a cruel twist of fate I could do nothing about. Being a woman trying to live as a man put a terrific strain on me and caused me to constantly dwell on what I was doing wrong to feel so lonely.

When I finally made it out of my gender closet and into the world, my loneliness amazingly began to go away when I started to interact with other women. While men shunned me, ciswomen were curious why I was in their world. When they found out I was not some sort of fraud and a honest human being, it was OK to talk on a shallow level. Which was fine with me because I was so lonely after my second wife unexpectedly passed away. Her death taught me to never take anything for granted again and I set out to live more deeply as the transgender woman I was becoming. Just breaking down the gender barriers I was doing was never enough to get behind the gender curtain. I needed to do more.

Primarily, I needed to learn all over again how to talk to people. Mainly women but also men. Women I found came at me from all different directions and practiced a lot of nonverbal communication. I needed to practice the art of passive aggressiveness also when I found a smiling woman was not necessarily a friendly one. Until I proved to be up to the gender communication challenge, life became very interesting. Perhaps you have noticed that for the most part I left men out because for the most part, they left me alone. Which was fine by me, because with most of the men I did encounter, all I did was soothe their ego. Payback I guess from all the time I spent in the male world.

By this time in my life, I was looking at being sixty directly in the eye and could see very few avenues available to me to combat the extreme loneliness I felt at the time and had just figured I would have to spend the rest of my life by myself. As someone once said, the darkest hour is always right before the dawn and that is what happened to me. I already had my casual lesbian friends who met with me several times a week to watch sports and drink beer until my current wife came along online of all places and we cemented a wonderful relationship. Firat of all, Liz made me a believer in myself again. A confidence I had always had as a man but never as a trans woman.

Unbelievably, destiny had worked its magic, and I found someone to love in the world again and we lived close enough to make a romance work. As long as we are together (over twelve years now), we will not have to experience any lonely days in a cold world ever again.

For those of you who want to know more about how I did it was the only way I made it out was putting myself out there in that same cold world. I had to battle my fears by going out in big straight sports bars and becoming a regular. And, beat all the long odds to find a romantic partner on an online dating site. My big break came in the sports bars when a bartender I knew as a regular set me up with her single lesbian mother who I am friends with to this day. My moral to the story was I needed to put myself out there before I could reap the benefits, but I know the world has changed and you have to be careful.

One way or another, we transgender women and trans men live in a potentially very lonely world which is a shame because we have so much more to offer than the average human because we have seen so much in our lives.

Thanks for reading along and contributing with claps and comments! Hopefully I can come up with something meaningful to you.

 

Friday, July 10, 2026

It's Your World to Live In

 

Image from Gabriel Silverio
on UnSplash. 

When it comes down to it, it is your life to live and no one else’s. But life comes in the way.

The problem is often for transgender women and transgender men, it is easier said than done to live our own lives. Especially for those of us who had to wait until later in life to go after our dreams of transitioning into a feminine world. Perhaps, you were like I was and called selfish for my one-sided obsession about even seeing if my male to female dreams could ever become a reality. My second wife was fond of telling me my cross dressing should not be all about me.

The longer I pursued life on my new transfeminine gender path, I realized she was right. In order for me to move ahead in a world which felt so natural to me, I had to be selfish. It was the only way I could make the difficult decision to take a leap of faith and try to jump the gender border.

Back in those days, the only thing I could hang my pantyhose on were the annual Halloween parties I was going to dressed in my feminine finest. During these early parties, I learned a few of the basics I would need to survive as a trans woman later in life. Such as how visibly trained the human animal is to the genders, and if I was to go to the feminine side, everyone (male and female) would be noticing me. My new visible role in the world took some time and effort to get used to, but I did finally do it when I learned to dress to blend with the other ciswomen around me. It was my life to live, and I was coming closer and closer to deciding how I wanted to live it.

Before I did, I discovered I still had a whole lot of living to do before I made my decision. The problem was my male life on occasion was not that bad. Which gave me false hope that I could save it. All it did, as I juggled two genders at once, was to make my life a mental health hell as I struggled to maintain any sort of life I wanted. On one side, I had the increasingly financially successful male self-making it harder to give up all that he had earned and the male privileges which came with it. Struggling with my feminine side which felt she was in a more natural position to thrive. The end result was whatever decision I made just had to be the right one. With so much at stake in my life, I needed to go back to being very selfish with myself to make it.

In the meantime, I went into a heavy experimentation period of my life as a novice transgender woman. My goal was to try to live every moment that I could discover what a ciswoman has to go through in her life. So, I could tell if I wanted to do the same thing. I wanted to be more than the “pretty, pretty princess” that my second wife always called me when she was trying to make fun of my femininity to learn what she was really talking about. It was a struggle, but eventually I did by setting up my own version of a transgender bucket list of things to do. What did a ciswoman know that I did not became my main goal in life when I shed my male clothes and went out in the world as a trans woman. Overall, my plan worked well for me except the times I tried too hard and ended up in redneck bars where a single woman should have not been to begin with.

I did so much, I wore out my bucket list of obvious things to do and began to examine the difference between male and female privilege in society. Losing my male privilege brought about no real surprises such as having my intelligence challenged and learning to be more careful with my personal safety. While the main feminine privilege I felt was the freedom to be myself in the world and went way past just having doors opened for me by men. Needless to say, I was in love with the whole path I was on as a transfeminine person and could not wait to get back to it anytime I had to leave and go back to my increasingly unwanted male life.  I was stubborn but then again, I slowly realized I could never go back to the life I had lived before. No matter how successful it was.

As I reached the age of sixty, I could put it off no longer no matter how stubborn my male self-had become. When my second wife passed away from a massive heart attack, he was left with no allies in my life to fight with and was done. I had paid my cross-dressing dues by doing the best I could with what I had to work with appearance wise and had gone out of my way to experiment with how ciswomen live by putting myself in actual situations in life which I could expect to happen. After all of that, I just needed the final push off my gender cliff, and land in a world of my own choosing. Without a perpetual balancing act.

In other words, I guess you could say I went too far in paying my own dues during the approximately fifty years it took me to lead a life to discover who I always was. I decided long ago tt was too late to cry over what I did or did not do and to look forward to the time I have left in the world. At the least, I found living a life on both sides of the binary gender border was as scary as it was interesting. How many other humans get to experience what a transgender women or transgender man gets to see in one lifetime.

Sure, we experience our ups and downs but so does everyone else and we can have such an interesting path to claim a life which was always meant to be ours.

HEY YOU! Thanks for joining me in my journey and commenting or clapping for my posts. You make it all so worthwhile.

 

Thursday, June 18, 2026

My Biggest "AHA" Moments

 

Image from Valentia Conde
on UnSplash.

During the long gender path which I have been fortunate to live, I have had many “aha” moments to look back on.

The problem I had was realizing that the times in my life were something I would forever remember, forget immediately, or just refuse to understand what they meant after my own ignorance set in. For my first example, I have to go way back to the first times I was exploring my mom’s clothes and makeup. I knew something was up, but I did not know exactly what and how deep it would run with me. All I knew was my desire to be feminine in any way was deeply forbidden in my family and most of society which called it being mentally ill at the time. Through it all, even though I did not fully understand what was going on with me, I did think I was mentally ill for thinking it.

That was the good news. The bad news was I was decades away from understanding the “aha” moment that I was living the wrong life as a man all along. Even if I was warned by a therapist that I respected very much that she could essentially do nothing about me wanting to be a woman and I was on my own to save a marriage that I really wanted to save. If I would have listened to her and started my male to female femininization earlier, I would have saved myself so much inner turmoil that it would have been amazing. But I did not and stubbornly hold on to the idea I could live as a man while at the same time cross-dress when ever I wanted as a woman.

Another problem was, I had moments when my feminine world was opening to me and I thought, “wow is that what being a woman was all about.” Like the day at the grocery store when I positively melted a young bagger who was stuttering as he shyly asked if he could take my groceries to the car. Right then I knew why I had such a difficult time talking to pretty girls in school when all my perceived smooth vocal abilities just disappeared. It was a giant “aha” moment when I had the chance to reverse course and cross that gender border so long ago.  

As I held on for dear life that I was just following my hobby as a cross-dresser, slowly but surely the idea of going through another male to female transition gained on me. I went back to the times when I was thinking that just putting on makeup and a dress was good enough. I always wanted to do more like the pretty girls around me did at school. I wanted to be the one being chased for a date in my new pretty clothes any time that I could. Which turned out to be never back then. Years flew by before they ever did as I began to test the world of ciswoman as a novice cross-dresser. Then, one night out of nowhere, the thought came to me that I was done just looking like a woman again, I wanted to inter-mix with them and see if I could be accepted. If I was, from that point forward I would change my self-gender perception from just being some sort of a harmless hobby to thinking about myself as a thriving transgender woman. A super scary, but exciting thought because once I went there and was successful, I could never go back to ever just thinking that I was just a man again. A real, enduring “aha” moment in my life.

The problem I had was once that I was becoming successful as a new transfeminine person, how could I stay there. Initially, I made up a new feminine persona to go with my new look. I wore the same wig and used my same new name every time I went out and before I knew it, I was being treated as a regular in all the venues I was testing out in the straight world I knew before as a man. Another big “aha” came when I was able to break the influence of all the gay venues I was going to which I really disliked and was accepted as me in a new world. Then I learned I could have fun doing it as I enjoyed my new feminine self so much that increasingly I did not want to go back at all to my old male world.

As I did, I began the all-important job of getting rid of all the male baggage I did not want or need anymore. At all costs, I hoped I could maintain a relationship with my daughter which I did, and if my brother did not accept me, so what. Which he didn’t and we went our separate ways as those two were the only two blood family that I had left. With all of that turmoil behind me, I was free to concentrate on my transgender future which did not include any surgeries at my age of sixty, but hopefully a chance to test out my body on HRT or gender affirming hormones. I was approved first by a doctor and then by the Veteran’s Administration to begin the hormonal treatment and positively loved it. It was as if my body was saying the hormones were an “aha” moment and were the missing ingredient to leading a fuller transfeminine life.

I am sure there were other “aha” moments which turned out to be bright light posts on my often dark and lonely gender path. Such as when my current wife Liz came into my life to love me and make me whole again by saying that she had never seen any male in me. I never realized that I had built up that much good karma to help my life along.

Thanks for reading my lifetime of gender experiences as a transgender woman. Hopefully, you can gain some insight to help you along.

 

Wednesday, June 17, 2026

Living the Dream before it Consumed Me

 

JJ Hart

As I crossed the six-decades portion of my life and spent at least five decades of it trying to stay under control by cross-dressing, I was trapped and had nowhere else to go.

It happened because I had embarked on such a complete path of looking like and moving like a ciswoman and my gender bucket list was shrinking due to too much use. All the trips to malls, antique stores, and thrift stores just became boring when I was passing through them with no problems. Even though I was bored, the idea of being successful as a transfeminine person still consumed me. And, to make matters worse, I was finding less challenges to undertake as I increasingly painted myself into a gender corner I had always dreamed about but never thought I could reach.

I always made excuses such as I was never going to be good looking enough to present well in the new world I was seeking when truthfully my overall confidence as a trans woman had more to do with my approval than my appearance ever did once I had went beyond the basic point I needed to be to blend in with the ciswomen around me. Life changed when I realized there were plenty of women in the world who dealt with being bigger in stature and even had broad shoulders such as I had. My realizations helped to give me the boost I needed to continue to let my so called “hobby” consume me.

The reason was that I was ignoring the fact that cross-dressing was much more than a hobby, it was becoming a lifestyle. The biggest problem was that nothing I did as a novice trans woman was ever good enough. Even my second wife did not like the person I was becoming when I took the time and effort to show off to her as I thought were my best feminine efforts. Even though I desperately was seeking her approval, it was becoming obvious to me that my inner feminine self and my wife were lining up to fight it out. I was left behind to pick up the pieces as I was realizing how consumed I was when I had one of my rare, sanctioned (by my wife) outings at Halloween in NYC when my wife decided she did not want to go with me. The night turned out to be a dream evening as I ended up going out with four other women dressed to thrill as I was and they all happened to be as tall as I was in our heels. The night even ended on a high note when I was asked to dance by a guy in the venue we went to. I turned him down because he had no idea that I had one basic difference from the other woman I came with.

Anytime I experienced such a wonderful evening such as that Halloween party, I wondered if the gender euphoria I felt was worth it when I came crashing down. I was consumed with the moment and wanted to re-live it time and time again, but I was tucked away in my male work world and could not get out. Looking back, I don’t see now how I survived the balancing act I was putting myself through. I needed to physically show up as the man I never wanted to be. While at the same time spend all my mental energy remembering the transgender woman, I was. If I could have cried during that time in my life, I am sure I would have cried myself to sleep many nights worrying about my gender dysphoria and how it always threatened to wreck my life. Even to the point of almost destroying my marriage to the woman I loved deeply when my frustrations would boil over into yet another fight about me. Some of the fights were so severe that my second wife told me I was not man enough to be a woman, or why didn’t I just go away and fix the problem and make both of us happier.

Perhaps, by this time, you are wondering too why I did not take her advice and do it. The main reason was, at that time, I was not ready to give up totally on the life we had together when I was a man and even though I was increasingly being consumed by the idea I could be the trans woman I always dreamed of, I was not ready to pull the cord and jump out of the plane just yet. Because I was still afraid of the new gender heights I was reaching and selfish enough to think my wife may still come around to accept me. For those of you who don’t know, she never did and died tragically of a massive heart attack at the age of fifty.

The whole experience sent me into a major negative tailspin which I had a difficult time emerging from. I think the only reason that I did was because I had let my feminine self-consume me, and she could not wait for the opportunity to take over and live. My life had come full circle, and all the time and effort I put into my male to female femininization came back to help me. I had already put the work into how I wanted to look with my make-up and fashion basics and was already out into the world actually discovering how it would be to carve out a new transfeminine life for my very own. I had gotten what I needed as I moved ahead towards beginning HRT or gender affirming hormones. Which were something I always wanted to try as part of my overall commitment to being as close as possible to being who I always was destined to be.

When life consumed me, I was always somehow able to accept it and even thrive with it. Even though it took me decades to do it with all the ups and downs of what I had to go through. At the least, it made life interesting.

 

Tuesday, June 16, 2026

So Many Ways to Come Out

 

Image from Nicola Dowie
on UnSplash.

Recently, I had a response from a young transgender man on how he should attempt to come out to the world.

First of all, thanks for the comment and yes there are many ways to leave your closet and enter the world of the gender you are trying to live among. I know too that I have many trans men who stop by and read my comments which flatters me because as we flip the gender script, often the worlds we must conquer are not that different. Gaining the female or male privileges when you feminize or masculinize yourself often are the biggest issues. After you come out to spouses and family.

Over the years, I have read about coming outs that have ranged from just showing up cross-dressed as your authentic self, all the way to writing letters trying to explain the way you feel. As far as I am concerned, just all of a sudden showing up as a woman (or a man) has too much of a shock value and is counterproductive when you are trying to explain how you want to live to the person sitting across from you. Writing a letter may be more preferable if you feel more comfortable expressing yourself with written words rather than speaking one on one with someone. In my case, even though I did not feel comfortable talking to family about my upcoming changes, I hitched up my new big girl panties (under my male clothes) and asked to speak privately with those family members closest to me.  My first attempt at coming out was with my only child, a daughter and as I always write about, she took it extremely well. Just to show me life could never be that easy, my coming out to my only brother went off the rails quickly and we have not spoken since about 2014.

Having said that, I do caution trans women and trans men who are just coming out to family and loved ones that you are in a marathon not a race and sooner more than later, your family might come around. Plus, there is an increasing amount of information available now to explain your desire to live as yourself. If you have the chance, you maybe able to direct them towards the positive aspect of what you are doing and away from all the negative news they may see from politicians on the media ads. In my case, the split between my brother and I ran so deep when he refused to stand up for me and invite me to our family’s traditional Thanksgiving Dinner, I just can’t forgive him for that.

On the positive side, the relatively few people who knew the former me notice almost immediately that I am happier now. And if you give someone the chance to calm down and see the real you, they will respect that and the real you.

Of course, as we flip back to the negative side, there are always those family members that will try to throw religion in your face. Unless you are more of a biblical scholar than I am, I usually just give up on them.

Overall, I find the different sides of transitioning between transgender women and transgender men to be interesting. Since I was raised around the male dominated world of trying to force my way through difficult situations, I never gave much thought to trans men having to adjust to not being passive aggressive so much. Then there is always the idea of using the restroom which hangs over both of us. Even though trans men are in a new world in a men’s room where no one wants to make eye contact or speak, there is always the idea of having to still find a stall to use. Which conceivably could attract unwanted attention depending upon how well you present and how long you have been on testosterone. I know I have oversimplified the men’s room process and if you are a trans man, I am always up for ideas on restroom survival.

Flipping the script again, using the women’s room as a trans woman is something I know quite a bit about. The first thing I quickly learned was I needed to make contact and speak when someone else was in “the room.” From there, much of what I learned was either common sense such as never placing my purse on the floor and making sure my stall still had toilet paper all the way to trying to pee in the bowl a certain way to mimic the ciswoman in the stall next to me. Then, no matter how much I was in a hurry to leave, I had to always stop at a sink, check my face and always wash my hands.

Anyway, you cut it, when you have desire to cross the gender border either way from male to female or female to male, you must learn so many nuances of the moves you are making. Even though there are strict rules you need to follow, often times you will find yourself making up your own rules as you go along. It is just the nature of the ultra-serious game we play. What has worked for me in the past may not work for you and often I hear from readers who have supporters and non-supporters in the same family. The only advice I can offer is to embrace your new gender allies and hope your detractors come around.

The end result always must be it is your life to live and you need to live it to be happy. Sometimes your path will lead you the wrong way, just like your GPS does on occasion but it is not time to panic until you can get readjusted. Be patient, and it will happen.

As always, thank you for the comments I receive, often they are difficult to answer seeing as how we dealt with such a complex issue such as gender. I just hope, in my small way I can help.

 

 

Monday, June 15, 2026

Feminine Power Moves

 

Image from Gayatri Mohotra
on UnSplash.

When I first began to seriously explore the world as a transgender woman, I was stripped of all my male privileges and wondered what I could do to survive if I found myself in questionable situations.

The big answer I learned was to try my best not to get myself into questionable situations to begin with. Lessons learned at an early age by ciswomen everywhere such as trying their best not to jeopardize their own personal security from toxic men. When I first came out, I was used to going where I wanted to go, when I wanted to do it which led me into several tense situations. One from a much bigger cross-dresser admirer who had me in his sights in a narrow hallway where I could not escape and another time when I was approached alone on a dark city sidewalk by two men in front of a gay venue. Neither place I should have been to by myself, and I was lucky to escape without any real problems.

By this time, I was used to the only feminine power I had was having doors opened for me by men and I knew I was missing much more in life if I wanted to pay my dues and transition into a transfeminine world basically the hard way. Since I couldn’t afford to go through any of the expensive gender surgeries of the time and did not have any insurance coverage that would cover any facial surgeries, I needed to find ways to accomplish what I wanted to face on my own. I learned the hard way that I could do anything I wanted to if I set my mind to it. Or I passed out of sheer willpower according to my transgender girlfriend Racquel. All it really meant was I was able to work my way into living the life I wanted to live through more effort on my physical appearance through better makeup skills and wardrobe basics. The same things I noticed other ciswomen doing in the world who themselves did not really have “passing privileges.” I just came into my privileges as a woman from a different way.

Another difficult phase of my male to female feminization project was the impact of woman-to-woman communication which continually goes on in the world that men are not subject to. Or the world of non-verbal communication women often use between themselves. I even went to the extent of taking feminine vocal lessons which focused more on what I said rather than how I said it. The keys I was taught were mainly built around the passive aggressive tone’s ciswomen take such as “are you sure you want to do that” rather than the traditional male “don’t do that.” I got quite a bit of valuable gender information from the course to use on my path which was always full of male stop signs. To repeat what I just said in essence instead of giving me a stop sign, my inner feminine soul was saying do you really want to do this.

Of course, the answer always came back to me one way or another that I was on the right path, and I felt so natural doing it that I just had to keep exploring what was ahead around the next blind curve. It was at this point that I began to discover what I had suspected all along those ciswomen had more going for them than having doors opened by men. With the help of HRT or gender affirming hormones, I opened my world to a whole new universe of emotions and senses I never knew (or allowed) myself to have. I was the one who could reach for her coat without shame when she was cold when my thermostat went crazy with hot flashes at the same time. And I became the one who could cry a happy tear at the drop of a dime. If I needed to or not. It was all part of who I was as I began to explore my feminine power base I was developing.

As I always do, I cannot give myself much of the credit for doing more than just surviving in the new women’s world I was as I began to thrive and enjoy my new power base. As my new friends kept telling me, welcome to their world. I needed to be careful how I responded because I did not want to give up much about myself and shield my male past.

Thankfully, by this time I had given up all my male privileges and was excited to be settling into my new life as a transgender woman preparing to go fulltime into the world. By doing so, I needed to prove to myself that I was no longer afraid of being rejected as a trans woman. Primarily by men who resented that I had left the boys club behind to slip behind the gender curtain to play in the girls’ sandbox. Thanks, in no small way to my lesbian friends who showed me how to validate myself.

Somehow, I managed to give myself extra time to drain the remnants of my old male life drain away before I went all the way and gave up all my male clothes. Which was the symbolic way of me finally severing my male past altogether. As difficult as it was to give up all those decades of struggling in a life I did not like, the relief of doing it was amazing.

Before I knew it, I was enjoying everything I could in the new transfeminine life I had only ever dreamed of. I was fortunate that I was able to live through several severe gender-based self-destructive incidents that I paid my dues on and was able to move on to find a whole new set of powers.

It turned out that I was simply giving too much trust to male powers I was born into and never had a chance to do anything about it. When I did, I seized control of my true powers and never looked back.

 

 

 

 

 

Violating Gender Boundaries

  JJ Hart. Pushing my gender\ boundaries.  Very early in life I learned that violating gender boundaries could result in severe trouble. I...