Showing posts with label transfeminine. Show all posts
Showing posts with label transfeminine. Show all posts

Friday, September 12, 2025

'Cation

 

Headed for Maine!

I will be off-line for approximately the next ten days because my wife Liz and I are headed off from our native Ohio on a bus/train tour of Boston and New England.

Mixed in with all the planned activities are my usual paranoias with acceptance and restroom usage. It helps we travel this time through more liberal minded states, rather than the deep south where we went last trip we took. For the record, this is our fifth trip with this company, and I have had no issues with what bathroom I was using, so you would think I could quit worrying about it. But I can’t completely. I just want to relax the best I can and enjoy activities such as a lobster bake (lobsta!) as well as other fun things to do in Boston up to Maine.

Sadly too, I need to rely on having an accepting driver who will help me unload my collapsible rolling walker so I can get around easier. The last driver we had helped me totally and his tip reflected it.

I am also looking forward to having another “lobsta” roll with butter along with a Maine Whoopie Cake which I had when we went up there a couple of years ago.

Most of all, I will miss checking in with all of you every morning with my ideas with how my life as a transgender woman came about. I could take my laptop along but decided against it. Primarily because I think a break will help me clear my mind and do better when I get back. Plus, I know pictures of me are not my strong point, and we are trying to get better on this trip. Maybe I will have more to share with you.

See you in ten days!

Tuesday, September 9, 2025

Dressing for Success

 

Image from Mohammad Nadir
on Unsplash

During my earliest days when I was forced into being a boy, anytime something negative or even challenging happened to me, I would run home and seek solace in my soft and colorful feminine clothes.

Soon I called the cross dressing I was doing, dressing for success. Mainly because I felt better as I did it. The sad part was, very soon the feelings of gender euphoria went away, and I was back in my unwanted male world where I was expected to succeed. During that time in my life, I was able to barely keep my head above water and still slowly improve my feminine basics in such things as the makeup arts. I guess all those hours of watching my mom apply her “face” as she called it, came back to help me. This was the 1950’s when women took their appearance much more seriously than today. All women were expected to dress for success.

As I barely stayed afloat with my cross-dressing challenges, it soon became more evident to me that there was much more going on with me than met the eye in the mirror as I tried to appreciate myself. It was about that time, when the internet showed up, and I was able to research terms such as gender dysphoria and transgender. Suddenly, I discovered who I might be and certainly found I was not all alone. It all started to make sense why my urge to cross dress never really seemed to go away. It was always with me in the back of my mind.

Soon, as I joined the world as a novice transgender woman, dressing for success largely depended on if I could go out into the world and blend in. I began the easy way by trying my hand with shopping mall clerks who for the most part were only nice to me for the money I needed to spend so I could be more fashionable and feminine. From there, I branched out to challenge myself by stopping to eat lunch and face servers one on one to see how I did. I did well, and very rarely did I have to run home and wonder what I did wrong and go back to my gender drawing board. I did not realize it but what I was doing was replacing my mirror time with time in front of the public. A very valuable learning experience as I discovered venues such as coffee shops, bookstores and even antique malls where I could shop and relax.

Each experience helped me to learn more about myself as a transfeminine person and then dress for success from it. To quit being so flamboyant with my wardrobe and wigs became my new goal as I was settling into my new life. People began to know me quicker, so I needed to be better in my approach to dressing for success. I learned I did not have to lose any of the enjoyment I experienced as a trans woman; I just needed to follow the lead of the cisgender women around me. I did not necessarily have to dress down for the grocery store and up when I mixed with the professional women out for a drink, but it helped me to feel better and relax. Plus, heels and hose would have certainly not worked when my lesbian friends, and I got together.

At times I even took my dressing for success to the extremes to be able to judge what the public was thinking of me. I used to wear my best sunglasses so that strangers could not see my eyes and tell I was looking at them, but were they looking at me? And one of my favorite “props” to use when I went out to be alone was my cell phone which I always had handy when I turned out to be the only woman at the bar. That way, I was trying to show anyone else I had someone else on the way, and I was saving their seat.

To be sure, dressing for success as a transgender woman was always a more complex process than doing it as a man. From undergarments to accessories such as jewelry, wigs and purses, women naturally lead a more layered life which can be reflected in the way they dress. I certainly had many more compliments on my outfits as a woman than I ever did as a man. Primarily, it was because it was something men never do and often, many cisgender women used compliments as simple conversation starters when they were curious about me.

As with all cisgender women, dressing for success is something transgender women must learn. The problem being we come from such a vastly different background to do it. Almost none of trans women had the benefit of peer pressure and a mom to guide us through the initial makeup process. Our workbooks were blank when we started our gender journeys. Playing catchup was not a fun game to play for me as I found making up my face was different than painting model cars. Most certainly, dressing for success was a lifelong experience for me.

 

 

Monday, September 8, 2025

Gender Dreams

 

Image from Greg Pappas 
on UnSplash.

This morning when I woke up, I took a moment to remember the sadness I felt when I got up in the morning and I was not a girl. I had the same sad realization, I was still a boy and nothing had changed. Plus, it is important to point out that I had no other dreams when I was young such as being a professional athlete or a doctor. All I wanted was to be a girl. I figured I was the only boy in the world who felt that way.

It was on those mornings when I needed to realize I was still male, and I had a long trip to make if I ever was going to change it. As my life became more complex, so did my gender dreams. Sometimes, I could not wait until I went to sleep to see what sort of dreams, I would have that provided me a respite from the days activity of being a man.

It was not until I decided to come out of my closet and test the world as a transgender woman, did my nights began to change. Replacing dreams with action was often a very scary proposition. But it was one thing I had to do if I was ever going to see if I could make it to a new transfeminine world at all. Would the public ever come to a point where they would accept me as more than just a man in a dress. Out in the world to be laughed at. If I could never make it past that point of being a cross-dresser, did I want to go on any longer and forget all the dreams I had. I finally discovered there was much more to being a woman than appearance and it was just my male ego trying to influence me.

Still, as I struggled along in my novice cross-dressing years, my gender dreams began to change with it. Instead of just wanting to be a woman, I started to dream of how it would be to live as an attractive woman and not have to worry about my presentation so much. I think it was because I was becoming more confident in myself, and my subconscious self was adjusting to the new me. More or less, I was reacting to the kinder, gentler world I was in as a transgender woman, and I loved it.

My main problem then was, could I make it to my dream when it became a reality. I was frustrated when I thought I could see the finish line and it was taken from me due to unknown transitional experiences such as what would I do about supporting myself if and when I made the decision to go from a male world to a female world. And would I need to prepare to be lonely the rest of my life because the possibility of someone loving and accepting a trans woman were exceedingly rare at my age of sixty. I was fortunate and exceeded all my dreams when I was financially able to take an early retirement and support myself and found my wife Liz (or she found me) on an online dating site. At that point forward, I had painted myself into a corner and I had no real reason to not follow my dream of being a transgender woman full time. Because I had finally faced up to myself and realized I had always been trans parttime, even though I could not share it fulltime with the world. 

As I faced up to reality, my nighttime dreams began to change also. Slowly my old male is disappearing from my subconscious too, He is being replaced by new dreams with me living as my true, authentic self. Maybe it is because he was pushed out of his final hiding place in my mind. Whatever the case, I was not sad to see him go.

I wonder now, what my childhood boy would think if he could see me now. Doing much more than just hiding in a gender closet waiting for brief moments to escape and explore. I am sure he never thought he would have the ability or confidence to be who he always wanted to be. Not an athlete or a doctor, just myself…a woman. I certainly had to come a different direction to claim my prize but maybe by doing so, I appreciate it more because it was never just given to me.

The boy I was would have never known his dreams would have never turned out like this, and being happy would not have been so far away also when she was playing with the girls. Where she always belonged.

Sunday, September 7, 2025

Off or On the Transgender Highway

 

Image from David Valentine
on UnSplash. 


When I seriously pursued my male to female life as a transgender woman, along the way I was fooled into thinking I was on a smooth fast interstate highway.

What happened was I was stuck on slow-moving two-lane gender roads and going nowhere for years. Plus, I needed to keep an eye out for potholes bumps and sharp curves. Too many times, I led myself down dead-end streets when I transitioned. The entire process just slowed me down and I lost decades in the process. Then I discovered one of the main problems I had was my old male self was exercising too much influence on my life. My main example I always use were the ill-advised fashion choices I was making when I tried teen girl outfits in my thirty-year-old testosterone poisoned body. I was guilty of not looking around and noticing what other women my age were wearing or what I could wear to disguise the defects I inherited with my body. Even though I was always going to be a big woman, there were plenty of other women my size to blend in with in public. While I am not a huge proponent of age women’s fashion, I am a proponent of looking good and not shocking the world.

One way or another, as I was able to put most of the fashion mistakes behind me, I was able to speed up a little and enjoy the new small gender towns and cities I always wanted to visit as a woman when I was a man. There were to be no more miserable vacations when all I thought about was when I could cross-dress again in front of the mirror. I was far beyond that point. I had developed the confidence I needed as a transfeminine person to take the next two-lane highway ahead and see where the journey took me. More than anything else, the mini trips taught me I could not go to sleep on my gender journey as I was risking my life as I knew it at the time.

In many ways, I was used to the pressure of discovery all along since it had started when I was so young. I just ended up accepting the pressure as a way of life for me if I was ever going to achieve my dream of living as a transgender woman. It all started with the threat of a psychiatrist visit when I was quite young, all the way to losing my family and job if I was discovered later in life.

Perhaps the biggest mistake I made on my road was trying to internalize the entire process and going through the infamous ill-advised purges of everything feminine I owned. It turned out to be one of the dead-end roads I was facing when I found I could not purge my deepest feelings of wanting to be a woman. In no time at all, I was back on the road and ready to try to get on the gender interstate. Many times, I was guilty of taking the wrong exit and having to go back to start all over again when I made the wrong choice of a venue and tried out a red neck, rightwing venue when I should not have. One time, I even had the cops called on me when I visited one venue, I was not familiar with.

After being told to leave, I quietly did and regained my composure up the street at a place where I knew I would be accepted and got back on the road. Once my transgender life began to speed up, I was able to stay on the interstate gender highway thanks to a lot of help from my cisgender friends who taught me more than they ever knew about discovering myself as a trans woman. More than anything else, they propelled me forward towards my dreams. They validated me to a point where I did not have to hide myself anymore on a bunch of dark deserted two-lane roads and stay on the well-lit interstates. I mention them a lot because without them, I could still be hiding my true transgender self away in my dark closet.

It took me so long to transition, I wore out a couple of vehicles along the way, but I finally did it. Regardless of the naysayers who said I was not trans enough to make it, or I passed as a woman out of sheer willpower. I accepted my life for what is was finally at the age of sixty and did what I should have done years earlier. Stood up for myself and started gender affirming hormones (HRT) which was like getting a new sports car to drive on the gender interstate. Again, I was able to leave a lot of negative people behind and live the dream I always wanted to live, as a transgender woman.

 

 

 

Thursday, September 4, 2025

Why Would I do this to Myself?

 

JJ Hart, Club Diversity
Columbus, Ohio.

Even though it has been years since I have been asked the question which asks why I am transgender, I withheld all my sarcastic comments such as I found my gender dysphoria in the bottom of a cereal box and thought of a concise truthful answer.

The truth is I had always known but was afraid to accept it. In the meantime, I set out on a slow, often torturous process to reach my impossible dream. To all the naysayers I interacted with, I just wanted to say, if I was not serious about switching male to female lives, why would I do this to myself. I knew early on I brought a lot of the problems with the public I faced on myself because of my novice attempts at presenting myself to blend into society with other women. I was coming off like a clown in drag, rather than someone who was seriously trying to jump the gender border from male to female. I was not playing around.

As my old male ego suffered, my feminine ego persisted and finally I did better in the world. I think too, the world took me seriously for the first time and did not have to ask the “why” question. I discovered too, that most of the world was just doing their thing and could care less about me if I could just blend. As I did blend in and began to carve out a new life for myself, the “why” of what I was doing became more personal and pressure packed. I was risking a successful male life I had worked hard to achieve, in order to live a new life which was so scary and at the same time felt so natural. I was having fewer people ask me why I was doing this transgender trip to myself.

Which brings up the question why any of us would transition ourselves if we were not desperate to do it. As an example, my own personal example was all the self-destructive behavior I put myself through including suicide and alcohol abuse. I was a living example of why I would do all of this to myself to be a transfeminine person. I was serious about what I was doing and needed to continue up the gender path I was on.

What helped me too was when I began to see the same people more than once. Since I was easy to remember, strangers began to put a name to my face, and I began to become a regular in several of the straight venues I went to. I just followed my tried-and-true idea of if I was friendly, did not cause any trouble and tipped well, I would be welcomed repeatedly.

The farther I went along my gender path, I began to wonder what sort of a transphobic gender bigot or female TERF would even question why a transgender person does what they do. Such as making all the sacrifices we must make to live the life we desire such as risk losing family, spouses and employment. Slicing off a major part of our life and starting over is intimidating enough without the naysayers questioning it.

On the other hand, there were things I wanted to do to help my feminine transition along such as losing nearly fifty pounds and beginning to take better care of my skin. Suddenly, I had access to more fashionable clothes which fit better, and my makeup was easier to apply. All because I took the time to take care of my transfeminine self. When I did so, even the haters I still encountered needed to get over it because I was more secure in myself. Even though I was increasingly successful in the world as a transgender woman, humans are like sharks, and every now and then I needed to fend off any unwelcome attention I might have attracted.

Possibly, the most important answer to the “why” question came when I decided to seek a doctor’s help and begin gender affirming hormones. Naturally, the decision on HRT was a major one and not a decision to be taken lightly. At the time I started hormones, I was leading a healthy male life which would have to change. I knew all along, I had come too far on my gender path to turn back now and quickly learned I had made the right decision to start HRT. My life blossomed as never before, and I never missed my old male body and emotions again.

By this time, I had married Liz and settled into a transgender dream world I never thought I could achieve. I guess I was to the point of if I could dream it and could do it. Which is a topic for another blog post altogether.  Plus, I had answered the question once and for all of why I wanted to do this to myself. It was fulfilling my own personal destiny.

 

Wednesday, September 3, 2025

Fight or Flight?

 

Image from Anna Deli
on UnSplash.

As a man, fight or flight became very important to me. Primarily because I needed to become the protector of the loved ones around me and myself.

To be clear, I was never much of a physical fighter, but as I grew into manhood, I was not shy of confrontations either. I could use my size and or male knowledge to back off most potential opponents. For the most part, it was a straightforward proposition. Rule, or be ruled.

Of course, when I transitioned from my unwanted male life into a new exciting feminine world, my idea of fight or flight needed to dramatically change, before I got hurt.

Not too long ago, I had a question from one of my readers asking me what the most important male privilege that I lost was. I replied, the loss of my personal security. I found out quite quickly how dangerous men can be to women a couple times right after I transitioned and left myself in compromising situations around toxic men. I was fortunate my second wife was around to bail me out the first time and I was able to spend my last five-dollar bill to pay two guys off to leave me alone on the second. The best five dollars I had ever spent! (There probably should be something to the effect I was cheap but not easy brought up too!)

All kidding aside, escaping these situations taught me valuable fight or flight lessons. Gone were the days of out bluffing other men in potentially harmful situations, and in were the days of planning ahead to stay out of situations which could cause me trouble. Keep in mind also, I was spending most of my time out to be alone in those days, so I as completely alone as a transgender woman. If I passed as a cisgender woman, was I in better shape than if I was read as being a trans woman. There was no good alternative, and I always kept flight ideas in the back of my mind if I needed them. I think one of my biggest paranoias was having some bigot sneak up on me from behind and pull my wig off. Which never happened.

Through it all, I suffered from not having a girlhood to grow up in where I could learn the lessons all cisgender women know. Such as doing their best not to find themselves in dark unlit parking lots alone. Following my close call on a dark city street outside two gay venues, from then on, I had a trans man friend of mine walk me to my car to be safe. It was a different experience to be sure for me, but there was/is safety in numbers when it comes to leaving your male safety privilege behind.

When it comes right down to it, your fight or flight chapter of your gender workbook needs to be filled out quite quickly. I know several transgender women who carry weapons in their purses for protection. Even though I was infantry trained on weapons in the Army, I choose not to arm myself because of the fear of shooting myself. My wife Liz and I have talked about the possibility of buying pepper spray as a deterrent, but we just don’t really go anywhere where we could be in danger of using it. So, we have not acted on any moves to arm ourselves yet. Plus, Liz went through some intensive martial arts training several years ago which she could use. There is a plan for us to use if we have to fight in an increasingly toxic world in which I am just about totally worthless at the age of seventy-five and with mobility issues. Ironically, I have experienced yet another full circle moment in my life as I have gone from a fight-first mentality, all the way to a flight first priority. I guess it comes with the territory of being a senior citizen transgender woman.

Whatever the case is for you, please be careful in whatever path you choose to go as a transfeminine person. Just use your new feminine wiles to help you stay safe just knowing it is a possibly toxic world depending upon where you live. I have an on-line acquaintance who lives in rural Tennessee who has been slowly coming out in the recent months, and by sheer willpower, she has chosen to stay and fight for her existence. It takes a lot of courage to say to one of her neighbors who threatened her job by saying she was transgender, to get over it, but she finally did. And she still kept her job, so it is possible to fight instead of fleeing. As I said, just be careful if you do it.

I think the worse bigots to fight are the Bible thumpers who want to quote scripture to you. I am far from a biblical scholar and can never remember a rebuttal to use when and if it ever happens to me. It never has because I would have to fight not to flee the situation.

 

Monday, September 1, 2025

The Second Time Around

 

JJ Hart (middle) at my first
Girls' Night Out. 

If you are one of the rare human beings to experience a second time around in life, you owe it to yourself and others to live it the best you can.

Being transgender can give you that rare insight into two of the main binary genders which should give you an edge in dealing with the everyday world. Having an intimate knowledge of whatever the other gender maybe thinking of us as trans women or trans men brings out fear in the public's eye. Who are we to possess such a wonderful scope of knowledge anyhow? It is especially bad with the male gender who has such a poor grasp of their sexuality to begin with. I know when I transitioned from male to female, one of my main concerns was my own sexuality. Was I expected to suddenly change my sexual preferences which had always been with women and suddenly start liking men. I even went to the point when I first came out when a straight woman friend of mine told me to buy bananas and practice. I will let your imagination do the rest.

We all know though there is so much more to a gender transition than sex when you set yourself up for the second round in life. I found I was leaving a life as a man where I was mildly successful and entering a totally new world full of women who were able and willing to question my existence in their world at all. Away from men, the women were a complex tribe, and it was difficult for me to be given the access to play with them behind the obvious gender curtains. First and foremost, just looking like a woman just got me in the game and the difficult part was just beginning. I spent hours and hours in the world just learning how to be the new me.

Suddenly, before I knew it, the doors to a totally different world opened for me and I was invited to the girls’ night’s outs. The invites could never replace the learning experiences young girls have when they are in their formative years and they get to go to girls’ overnighters with friends, but they were all I had to attempt to catch up on my gender homework. No chance to experiment with makeup or gossip about boys or other girls.

The main problem was, I had another male life to deal with at the same time. Looking back, I don’t know how or why I put up with all the gender stress and tension I did to make it to my dream. I guess the reason was I did not have the confidence to know if I could make such a major life changing step at all. We all have a lot to lose when we undertake such a step, don’t we? Plus, as I slid towards the idea I could live fulltime as a transgender woman, I was being accused of being selfish. Which made me feel guilty until I finally came to the conclusion I was being selfish. Because I had to save my own life.

As I was accepted into the girls’ sandbox around me by the majority of the women around me, my confidence grew that I could indeed live a second time around life as a transfeminine person. My long hidden inner female took over and surprisingly became a rather social person as I formed bonds with my small group of lesbian friends which was the best of all worlds for me. As I always say, the first and main thing my friends taught me was I did not need a man for validation. Which included my sexuality. All I needed to do was still keep an eye out for the rare bigot who hated me for no real reason. It turned out the haters would have to go through my cisgender friends to get to me, if they wanted to.

At that point in time, I met my wife Liz, and my second time around became easier and easier for me to live up to. I say live up to because I found myself at a point where I always dreamed of being. But I never thought I could make it. Never say never became a reality for me when Liz told me she never saw anything male about me. I was in gender heaven and stayed there until I realized what a heavy burden I needed to face. Here I was with the rare chance for a do over in my life and to not repeat the same mistakes I made as a man.

So far so good I think as I head down the stretch run of my life and I can be thankful for the chance to live two lives regardless of what the gender haters say.

 

Sunday, August 31, 2025

Long Labor Day Weekend

 

Image from Anna Storsul
on UnSplash

Labor Day weekend is upon us in the United States which gives us an opportunity to take an extra day off and think about what got us here and how close we are coming to losing it.

Even though I have never been in a union myself, I am an amateur historian and know what unions did to transform this country. All you need to do is some basic research on how bad working conditions were in the steel industry as well as coal mining and elsewhere to see what unions brought about. So, on Labor Day, I salute them.

Elsewhere, the weekend this year features some beautiful weather with sunny blue skies and very low humidity for a change around here in the Ohio River Valley (Cincinnati.) Of course, the early fall like conditions won’t last forever and soon we will be back into summer’s last call. In a couple of weeks, my wife Liz and I will be headed for the East Coast, Boston, Maine and more so I am hoping for the reasonably good weather to hang around until then.

By now, you may be asking what does any of this have to do with being transgender? The answer is it has everything to do with being myself as a transfeminine person. Since this marks our fifth bus tour over the years of hanging out with other cisgender women waiting for my chance to use the bathroom, I still have lingering paranoia with using women’s rooms which goes back to my earliest days of cross dressing in public. Even though I have not had any problems in the past with anyone else, I still have the idea it only takes one bigot on the bus to ruin my trip. At least, this time we are traveling through more liberal blue states, so I won’t have that to worry about. As I said, my lingering fear is subsiding, so I can concentrate on having a good time and seeing the sights of New England. The last trip we were on a woman asked if Liz and I were sisters, so you cannot get more validation than that.

Closer to home before we leave, tonight we are going to dinner at our favorite restaurant with her son. It is another venue I have rarely ever been misgendered in and have never had any serious problems. It always feels good to just exist and enjoy myself since I worked so long and hard to get here as a transgender woman. The more I can fly under the gender radar in today’s world, the better I feel.

Before we go, I will have to shave closely, apply moisturizer, powder and lipstick before I change out of my The Ohio State sweatshirt and into a frilly feminine top and brush out my hair. All of which are still fun for me to do. Not just something I have to do to present better in the world.

Finishing out the day, it will be time to head home and watch the end of summer Cincinnati fireworks display. The display is always huge and attracts nearly a million people on both sides of the Ohio River. Back in the day, when I was younger and another person, I used to come down every year for the Booms. But age and mobility have caught up to me, taken their toll, and we just watch them on television now. Then let the out-of-control neighborhood idiots set their fireworks off and scare the animals and any near veterans with combat PTSD. Out of the two cats Liz and I have; one hates any sort of loud noise.

As with many other holidays, Labor Day presents yet another milestone in my transgender life. I can remember quite vividly when I used alcohol on holidays to dull the pain of not having the chance to spend them as my feminine self. I was fortunate to have escaped my closet and the control alcohol had on me before it was too late. It turned out it was all in front of me all along if and when I had the courage to reach out and seize my opportunity to transition and just be me.

I guess you could say, I needed to labor to do it, but it was worth the effort. When we toast ourselves tonight with our Margaritas, I will propose a toast to all the work we three have put into to where we are today. And, to all of you, no matter where you are today, have a chance to pause and celebrate the gender journey you are on, or have yet to do. Buckle up! It is one hell of a ride. 

Saturday, August 30, 2025

Out od Sight...Out of Mind?

 

My wife Liz on left and daughter on right.

Most if not all transgender women and trans men go through phases in their life when they think gender issues are out of sight and out of mind. It is not entirely different than the moves some state legislatures (Ohio) are going through to try to erase us in the public’s eye.

If you read my posts at all, you know how I feel about that. Trans people have always been around and always will be. Attempts to erase us will be futile. On a lesser but just as important level, we try to erase ourselves by purging our lives too. I know the guilt of being a cross dresser or transgender woman became too much for me to handle and I threw out most of my treasured feminine wardrobe and makeup. Out of sight, out of mind I thought.

In the long term and the short term, none of my purges worked because I refused to accept my true self. I had my life all backwards and I was not a man who cross dressed as a woman, but a woman who cross dressed as a man. Until I figured it out, I kept trying to hide the obvious. Of course, it did not help as I started with two gender strikes against me. I went through birth as a male and then had to go through male puberty and suffer from what I called testosterone poisoning. My body kept the bullies away and allowed me to play sports but caused me torment when I was in front of the mirror trying to be a pretty girl.

As life went on, I thought for the most part I had learned to live with my gender dysphoria the best I could. To this day, though, I wished I could be a “normal” male. How much better could my life be if I could socialize with the other males around me without feeling as if I was an outsider. I grew tired of being an actor inside my own skin. The only thing I could do was mentally try to get rid of my feminine self. Taking me full circle back to why I was keeping all those clothes, wigs and makeup anyway. It took me by throwing them away to understand exactly what the problem was. It was not a problem unless I it made one, which I was by purging again.

Deep down I knew I was wrong and very shortly I would be re-stocking my fashion and make up to try my best to present feminine again to myself and the world. However, I was very stubborn and my male self-hung on way too long refusing to give up on his hard-earned male privileges. Life could have been much easier by staying where I was in the gender world, but it was just wrong, and I couldn’t. The more I lived as a transgender woman, the more natural I felt, and I never wanted to go back into the male world I had made the best out of.

Increasingly, the male purge was looking to be the one I was going to attempt to make. I was sick of living a gender lie, and I wanted to reverse my idea of living. I wanted to feel “normal” again but this time around a group of cisgender women. Flipping the gender script on my life was the most difficult thing I had ever attempted to do, but somehow, I made it through the female gatekeepers and did it.

In my new transfeminine life, I was rarely out of sight and out of mind. I had a lot of help to do it who I will never forget. I had spent my whole life chasing a dream and had finally achieved it. As I symbolically and literally gave my male clothes to charity, I stopped to remember the entirety of what I was doing. I was giving up the male side who had dominated me for so long. To be sure, he had served me well, but it was time to go, and this final purge was a triumphant one for my transgender woman who had waited so long to live. After all, she had her life taken away several times when she was purged nearly out of existence.

She survived and so did I and everything in her power to make things better. When I worried how I would be perceived in a new world. She had my back when it mattered, and it did. Even in the days when she had to give me quite a bit of tough love. She had to watch me grow through my ill-advised teen cross-dressing years into a presentation I could be proud of or at least satisfied with.

Out of sight, out of mind never worked for me.

 

 


Thursday, August 28, 2025

Gender Immigration

 

L'eggs said it best.


With all the negative publicity being brought to the new immigrants to this country by the orange felon/pedo in Washington, I thought it might be time to connect the dots to my own immigration. A gender one.

My immigration plans began as a vacation. I was tired of the male world I was competing in and taking a break as a cross-dressed girl in makeup was a great way to escape my life. Little did I know, from these humble beginnings, I was starting a lifelong journey which in many ways, I am still on over a half a century later. Had I known, I would have ever attempted to undertake such a radical immigration.

Early on, I was just looking to grab the so-called low hanging fruit of cross dressing. I enjoyed the feel of the clothes, all the way to the thrill of hose on my freshly shaven legs. Then, I slowly began to realize so much else was happening. Increasingly I wanted to be more and more like a girl and started to wonder about pushing my male self out. It was difficult because I came from a highly male dominated family. As I pushed forward, my immigration into the feminine side of life became more intense. I tried my best to acquire new more fashionable clothes and even bought my own makeup and panty hose. Do you remember the “L'eggs” panty hose which came in plastic egg shaped containers which it seemed you could buy everywhere, and is still made today. I learned the hard way; how easy it was to destroy a pair when I unfortunately ran one of the legs. Ruining my outfit.

Progression was slowed by a late-teen collision with serving time in the military due to the Vietnam war. Obviously, I could not bring any of my “stash” of women’s clothes or makeup with me, so I was stuck. No more gender immigration for at least three years of my young life. There were several major positive things which happened for me while I was stuck being a man in the Army. A prime example was all the traveling I was able to do around the world in places such as Thailand and Europe (Germany). The whole process enabled me to keep my mind off my gender issues and set me up with the idea I could outrun my problems. Which, of course, turned out to be impossible. Which should be the topic for another blog post.

After the Army, my life changed again as I entered the world of parenthood. Being a parent of a daughter was an unexpected but pleasant surprise, and my gender immigration was put on hold briefly again. I say briefly, because I discovered my transgender issues ran deeper than I had thought. My presentation as a novice transfeminine person was coming along. My first wife did not care, and I was able to explore my potential future as a gender immigrant at events such as Halloween parties. Each party to me represented a chance to see how I was being accepted as a woman in society.

After a few years, I ended up divorcing my first wife and marrying my second. She also knew about and accepted my cross dressing from the beginning of our relationship but never accepted me being transgender as I immigrated towards being a woman. My male side was like being the Titanic, slowly sinking and then picking up speed with her fighting me all the way. It turned out, the issues I was facing were like the tip of the iceberg. With most of it being hidden from everyone. Including me. She tragically passed away before the final resolution in our relationship was ever decided.

When she moved on to the other side of existence, it was left up to me to decide the future of my immigration. I had certainly paid my dues by taking on all the menial and not so menial work of being a woman. I was on gender affirming hormones and was living as much as I was able as a transgender woman, so I was close to filling out my immigration papers and was ready to go into a world I had only dreamed of. My presentation had improved to the point where I was not the most attractive woman in the room, but I could handle myself to the point where most of the world just did not notice me. So, my immigration was more successful than I ever thought possible.

Perhaps the best part of immigrating was learning to accept and love myself for who I really was. Which meant all the hassles I had over the years as I tested out the world, made my immigration worth it.

 

 

Tuesday, August 26, 2025

More than Theatrics

 

Christine Jorgensen circa 
early 1950's. 

Deep down I knew being feminine for me was much more than a theatrical exercise dressed in front of the mirror as a girl. I wanted to do more than just look like a girl; I wanted to live like one. I wanted to be the one with the pretty clothes that all the boys admired.

It turned out I was ahead of myself as far as my gender dysphoria was concerned. Gender dysphoria, as well as the term transgender had not yet caught up with the public at large. It was still transvestite, transsexual or Christine Jorgensen or nothing for me as far as having any idea anyone else in the world was like me at all. Perhaps you may not know it, but Jorgensen was supposedly the first widely known transsexual to come out with the very public news of her gender realignment surgery in the early 1950’s.  No theatrics involved, just a lot of publicity, I guess.

I thought of Jorgensen and the gender loneliness I felt the other day when I got to watch “Some Like it Hot” on our local PBS station. I was approximately ten years old when the film was released in 1959 and I remember being mesmerized by the idea men could be women at all. Even still, I don’t think, or remember, if I connected the dots yet to how I was feeling about myself. I was still very much stuck in the everyday struggles of being a boy.

When the internet became popular, I began to discover a whole, wide wonderful world of gender possibilities. Including a term which I had never heard of before, transgender. As I understood the term, it took away all the possible theatrics of just looking like a girl and brought up the possibility of living as one. At that point, I began to wonder if I was a cross dresser at all, and not more. The only thing I thought I knew was I was still in some sort of middle ground as my gender dysphoria went. I felt much more that I was so much more than the average cross-dresser, but not quite there yet as far as I wanted all the surgeries Jorgensen and others were going through.

To maintain any sense of mental stability at all, I began to explore the world the best I could to see if I fit in with this new transgender term I was reading about. My best and exciting evenings came about when I was able to be invited to and attend small diverse parties at a transsexual’s house in nearby Columbus, Ohio. It was there I learned about the dangers of being trapped by a much bigger and powerful man, all the way to being picked up by a lesbian I had never met before. Most importantly though, I was there to observe and learn anything I could from the hostess, a transsexual retired fireperson from Columbus who was headed to surgery. Michelle was beautiful and I was dazzled. I discovered there were no theatrics from her, she was as real as could be and I wondered if I could ever achieve what she had.

The main thing I did learn was, my deep feelings about living as a transfeminine person may not go the same way as Michelle’s did, but it was possible for me to live my own successful life as a woman if I tried hard enough. That is when I learned to put my cross-dressing theatrics away which had served me well and I entered another phase of my life. Michelle was beautiful and exotic in her own way, but I could do it too, just in my own way.

I would be kidding myself and all of you if I said finding my new self was ever easy. I needed to make all the difficult decisions about risking everything in my life which was important to me. Such as a loyal, long-term spouse, family, friends and good employment. The same things we all go through as we struggle to transition as a transgender woman. When I finally decided I needed to go the distance and give all my male clothes to charity, the weight was off from my shoulders to not live a theatrical existence as a man anymore. I spent over fifty years fighting a gender battle I could not win as the cards were stacked against me.

I was able to put all the gender questions I suffered through in my past and build a new transfeminine life the best I could. I just had to quit the theatrics to do it.

 

 

 

 

 

Monday, August 25, 2025

Come Out Swinging

 

Image from Chase Li
on UnSplash.

Often, I write about running home to dress in my skirts and put makeup on to hide the failures I was feeling as a male.

My plan worked well until I discovered I was advancing so far and so quickly as a novice cross dresser or young transgender girl, I was unknowingly destroying my hiding place. Someone turned the light on in my closet and suddenly I had nowhere to go. I needed to come up with a plan to come out swinging or I was doomed. In addition, I still had to be very careful not to be caught and end up in a psychiatrist’s office declaring me mentally ill. Then I would really have nowhere to hide.

The better I became at the art of makeup and dressing myself, the more I needed to consider what I was doing and wondering if I should come out swinging at all. The problem continued to be, I was building more male privileges in the life I was living. My life was like shadow boxing myself as I sought out answers. Like most of you, I was risking a lot as I came closer to pushing all my life’s chips to the center of table and betting it all on the fact I was a transgender woman all along.

Then I went into my highly recommended experimentation years of my life. In order to have any sort of an idea if I wanted to live as a transgender woman, I needed to walk a mile in my new high heeled shoes. Those were the scary yet exciting nights when I escaped the gay venues I was going to and began to attempt to establish myself as a regular in lesbian and other straight venues I was used to going to as a man. When I did, I discovered I needed to make another transition from serious cross dresser to transgender woman exploring the world. To my amazement I was successful when I went to venues such as TGI Fridays and socialized with other professional women. Maybe I did not have to swing so hard after all to escape the dark confines of my gender closet.

To be sure, I still had setbacks when I came out into such a different world, but I had enough gender euphoria to realize I could live out my dream if I worked hard enough at it. At first, I suffered from the “what I thought a feminine life would be” syndrome. I was trying to put all those years of closely watching how women lived into actual practice without paying my dues in the world. While I resented the fact, no one would let me see behind the cisgender woman gender curtain, I was becoming a victim which did me no good in the short or long term. So what if I did not understand what I was doing wrong, I just had to figure it out and do better.

One of my major problems was solved when I finally came to the conclusion I was never going to be accepted as a cisgender woman, but I could find my own version of womanhood on my own path. That is when I started to wear only one wig, settled on one name and began to build a new serious life as a transfeminine person in the world. As I settled into a new life, I found that many people (especially women) appreciated my honesty in a world of fake people. I was surprised at all the female attention I received and was relieved I did not have to attempt to change my sexuality.

The more I changed, it seemed the more I stayed the same as my long hidden feminine soul took control finally. I was dealing with life on a one-to-one basis for a change without having to swing away all the time just to survive. As HRT hormones entered my life, it was just another example to me of what took me so long. My body took to the gender affirming hormones flawlessly and I was off to yet another transfeminine adventure. My age and hormonal status led me down a new road of dealing with confrontations, no more could I try to macho my way through trouble, I needed to take the feminine path and try not to get into a situation I could not get out of before it happened. Or no more swinging away for me. I needed to use my brain for a change.

As I have pointed out in previous posts, I was never a good athlete and could never hit a curveball when I tried to play baseball. I finally took it all to heart and quit trying to hit a curveball altogether and settled into watching the boys play baseball (and girls too) when I did not have to play. I was tired of banging my head against a hard gender wall and ended up where I always should have been as a transgender woman. I just wish I had not been so stubborn when I was doing it and had shed my male self-long before I did.

 

Friday, August 22, 2025

In Over my Head

Image from Alexander Mass
on UnSplash
In the beginning, it was all so simple. Pick something, I could squeeze into from my mom’s closet, try my best to wear her makeup and go from there. Very quickly though I found I was getting in over my head as I began to sink into my own personal gender quicksand.

My first problem was hiding my small but growing collection of feminine fashion. In addition to my parents, I had a slightly younger brother I needed to deal with. Somehow, I managed to keep the darkest and potentially most destructive secret I had away from him, I wanted to be a girl in the worst way. I had no way of knowing then how many times I would be in over my head as I chased my dream. Primarily because I had no way of knowing looking like a woman was just the first step of a lifetime of gender learning. As I like to say, my gender notebook was blank when I received my copy, and I needed to catch up the best I could.

I began by studying the women around me who were my age the best I could. It was all I could do at that time to keep myself from setting myself up for failure when I finally was able to escape my dark, lonely gender closet and explore the world for the first time. When I did, I was naïve and confident I would have no problems. After I was sent home crying after being laughed at, rudely I knew I was in over my head with a lot of work to do. For some reason, for the first time in my life I knew I could not give up and I refused to quit. I kept going back to the drawing board until my makeup art improved and I began to learn the benefits of dressing my self properly as a woman of my age and build. Suddenly, I began to pull myself out of my quicksand and began to move forward again towards my dream of living as a transgender woman.

Ironically, as I moved forward, I ran into many other obstacles in my way. Was I pushing myself into a world which was ready for me or not was one of the main questions I had. The more involved I became in the world as a trans woman, the more I needed to be accepted into women only spaces. The only way I would ever know was if I could conquer my fears and try. As I pressed on, somedays I was more successful than others, but overall, I found I was accepted by other women. The times I found myself in over my head as a novice transfeminine person were primarily when I was approached improperly by men. There were times I needed to run home and rework my gender notebook after close ugly calls with men. I learned quickly, those close calls did not validate my worth as a woman. They did provide me with an insight of what women go through in their lives and I learned fast.

As I was adjusting to the new life I was destined to live, It seemed as if the lessons I was receiving kept coming faster and faster. I learned from my lesbian friends how to validate myself as a woman and from men, what not to do. At no point in time was any of my life easy at this point, but it was scary and exciting at the same time. My dream became so close I could reach out and touch it. If I kept out of the quicksand and kept my head above water, I could make it. The hardest part was still yet to come as I was coming increasingly closer by the day to separating from the male life I resented for so long.

The final decision to change was brought on by my choice to seek out gender affirming hormones or HRT. As I urge everyone to do, I sought out medical approval before I went down the radical path I was on. I was approved, put on an initial minimal dosage and before I knew it, changes were happening which made me a highly androgynous person. One look in the mirror told me that I had made the right decision and I wanted to move past the minimal dosage of HRT I was on.

I can’t say I haven’t found my way in over my head in recent times because of the type of person I am. Did being transgender aid in it? Who knows. We all have our choices to make, and they are all tempered by the people around us. Some are fortunate and have discovered feminine gatekeepers such as spouses were there all along. While others are destined to go it alone. Whatever the case, try to not get in over your head and do the best you can.                                 

  


Thursday, August 21, 2025

The Blues

 


I have not been ashamed over the years to document my struggles with depression, which was finally diagnosed as being Bi-Polar by a gender therapist I was going to years ago. Fortunately, the therapist was the first of several who did not try to connect the dots between my mental health issues and my depression. Saying one caused the other.

What was happening was, when I got the blues, I was down for days, not wanting to even get out of bed. Having said that, I was able to break the depression on occasion by cross dressing and going out into the world as a novice transgender woman. Breaking the hold of the blues was often very brief when I needed to return to the very mundane male world I was stuck in.

In addition, I was doing very little to help myself. I drank heavily, not considering how much of a depressant alcohol was and my favorite music to listen to was the blues. Regardless of my gender issues. As you can tell, outside of the Bi-Polar medications I was taking, I was doing very little to help myself. With or without the help I received, I managed to make it and eventually thrive rather than just survive. Regardless of my second wife calling me the “pretty, pretty princess”, I still took a lot of pride in my feminine presentation. The better I looked, the fewer blues I needed to conquer in my life because for once, I was doing something positive for myself.

When I needed the Veteran’s Administration’s health care in the worst way, they really came through for me. I was going through hard times when my restaurant closed financially and could not afford my medications when one of my employees suggested turning to the VA for help. It was about this time too when the VA approved gender affirming hormones for veterans so I could help myself on two fronts by making an appointment. It turned out that what I needed was an appointment with a therapist for both of my issues. My depression and my gender issues. By the pure luck of the draw, I was assigned to a therapist who had knowledge of my depression and my gender dysphoria. I was going into my first visit thinking I would have a difficult time explaining how my Bi-Polar depression had nothing to do with my gender outlook.

I never had to connect those imaginary dots with my new therapist. She had a good understanding of the needs of the LGBTQ community and what it meant to me. Once again, all the paranoia I had built up was wasted and my depression meds as well as my HRT meds were approved. It was the help I needed when I needed it at the lowest part of my life.

Regardless of all the good news I discovered, I still had to translate all of it into my real life which was changing dramatically. I was going out more and more testing out my interactions with the public. Building a new life was as difficult as I had imagined and the struggles I went through sent me back into the blues when I thought I would never make it as a transgender woman. To be completely feminized by no one else but me turned out to be a daunting task because I was starting from near to point zero. Very quickly, I quit being a victim and turned the tables on my male self who was fighting for survival, but not before I tried various self-destructive things such as trying to kill myself. The blues were literally trying to kill me.

In my limited understanding of both issues, I fought for my entire life, both depression and gender dysphoria could be caused by chemical imbalances in my brain. So, I had no real chance to battle them. I was born to a high-risk birth rate mother in the days when the medication DES was routinely prescribed. DES supposedly flooded the uterus with estrogen hormones which could have affected my future gender issues. Of course, now I will never know if my lifetime of struggle to fit in with males was doomed to begin with and now depression is widely believed to be caused by a chemical imbalance in my brain which I think I inherited it from my mom. One way or another, I feel fortunate to live in an era when medications are available to treat my depression.

In many ways too, the blues are an outlet I miss in my interactions with today’s world. As the mid term elections rapidly approach, I am preparing myself for the barrage of anti-transgender propaganda from the Republican party here in Ohio. Knowing what to expect won’t make it easier for me to survive. As always, I will just have to. With or without the blues because every little thing is going to be alright.

 

 

'Cation

  Headed for Maine ! I will be off-line for approximately the next ten days because my wife Liz and I are headed off from our native Ohio on...