Showing posts with label makeup. Show all posts
Showing posts with label makeup. Show all posts

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.

 

 

Wednesday, August 27, 2025

All I Had was Time

 

Image from Natalia Rabinovych
on UnSplash.

When we are younger, time seems like it is less of a commodity. When we are in school for example, all we want to do is graduate into the world.  For transgender women and transgender men transitioning, we often take time for granted. At least I did.

As I was coming out of my gender closet, regardless of not having much guidance on where I wanted to go to achieve my dream of living as a woman, I took my time. For a while, when I had finished serving my time in the military, the only outlet I had to being out in the public’s eye were the yearly Halloween parties I went to. Finally, I could see the writing on my gender wall and knew I would somehow have to do something, so I did not have to wait another long year to go out again. Time was being wasted.

It turned out, I could not see the forest for the trees, because there was a huge world just waiting for me if I just had the courage to do something about it. I needed to hitch up my big girl panties, not be a victim because of the bigots, and do something about escaping my closet. The problem was, I was always making excuses about why I could not do something as a novice cross dresser or transgender woman. So, what if my ego was wounded when I was laughed at early on, I just needed to go back home and figure out what I was doing wrong and fix it. Time was going by, and I was not getting any younger. Little did I know then, as I was in my thirties, how much farther I would have to travel.

I had my own transgender biological clock I was dealing with. Like any woman, I knew I only had a finite number of years to look my best to try to socialize in the world. All of this happened before I learned appearance was just the stepping off point when I tried to interact with the feminine world. My wife tried to tell me, but I would not listen, and I lost years in my male to female transition to learn for myself what she was talking about. Again, I was spending too much time as a victim wanting my wife to explain what she was talking about and not explaining it better to me. The problem was, I would not have listened anyway, my old male ego was still too strong.

In the meantime, I was getting myself caught up in major gender contradictions. I was spending up to three days of my week trying to learn the basics of being a transfeminine person and then turn around and having to revert back to the old male life I increasingly wanted no part of. It was no way to live and often I felt as if I was one of those jugglers I saw on television when I was a kid, keeping several plates balanced at once in the air. Ultimately, the entire gender back and forth nearly killed me.

My suicide attempt, among other things, woke me up to the fact I did not have all the time in the world. Especially if my self-destructive actions were trying to take it away. If I ever was going to have a chance to achieve my dream of living as a transgender woman, I might have less time than I thought to do it. At that point, I shifted my transition plans into high gear and began to explore in earnest if I could do it at all. Maybe it was my impossible dream. One way or another, I was in my fifties and needed to decide what I was going to do.

As I began to carve out my new life as a transgender woman, I needed to quickly learn what worked for me and what did not. My biggest move was when I worked my way out of gay venues where all they did was perceive me as a drag queen and enter the real world where I needed to prove I was more than just a man in a dress, wearing makeup and a wig. With more than a little help from my inner female who had waited so long to live, I was able to establish myself as a viable person to the public. As my trans woman friend Racquel said, I passed out of sheer will power, which I did. I proved I was not trying to fool anyone into thinking I was someone who I was not. For better or for worse, my friends knew they were dealing with a unique woman who had used her lifetime to arrive at the same point as they did.

Maybe I had spent my time wisely. One way or another, I learned a lot about the binary genders as time flew by. 

 

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.                                 

  


Tuesday, August 19, 2025

In Over my Head

 

Image from Wilhelm Gunkle
on UnSplash.

As I thumbed through my new feminine workbook, I sadly discovered there were no chapters on what to do if I got in over my head. In my well-built male world, I had been able to figure out strategies on what to do in times of duress. I could choose to stand and fight, try to bluster my way through, or just run from the problem.  None of which was available to me anymore on the gender path I was on.

Even though I was blessed with a healthy male body which was slightly bigger than the norm, I had hated the changes testosterone made to it when I had no choice but to go through male puberty. Very quickly, I grew past the sizes of my mom’s clothes I was trying on and had to find other ways to build my wardrobe on the very limited budget I was on. My newspaper route money, along with the small allowance I got for helping around the house, just didn’t go far. Still, I was able to sneak out of our rural home under the pretense of visiting my grandma who lived downtown and do some shopping for makeup and hosiery. I just remember how incredibly overwhelming the makeup selection was and how much I was over my head with my selections.

After I was able to smuggle my purchases past grandma and my family, then I needed to work earnestly on how to apply the makeup I bought and not look like a clown. After looking in the family mirror and feeling like a clown in drag, I knew I was in over my head and just had to find a way out, or in as it turned out. I wanted out of the male world and into a feminine world. The mirror was wearing off, and I needed to improve my presentation, or I was doomed to forever occupy a male spot in the world where I knew I was not in over my head. The white male privileges I was building up were just too easy to not take advantage of. Ironically, all the good I was accomplishing in the world with my family, friends and job was frustrating me because, deep down, I did not want it.

What was happening was my frail mental health was being destroyed by all the gender ripping and tearing I was going through. One day I was a successful man and the next I was working to present my self as a woman was very destructive to my everyday existence because the whole process took me back to my gender fluid days when I was a kid. Back in those days, no one knew about the gender fluid term, or used it which put me in over my head before I even really started in life. Remember, I grew up in the pre-internet dark ages when anyone who cross dressed was considered mentally ill. At least I knew, even though I might be alone as a transvestite (another term from the dark ages), I was not mentally ill.

I barely survived the dark ages when I did learn there were actually individuals like me who wanted to dress as women. I would be remiss if I did not mention Virginia Prince and her Transvestia publication at this point. It was my lifeline to the cross-dressing world and opened my closet for the first time. When the light came flooding in, at first, I was blinded, and it was difficult to find my bearings. My first transvestite-crossdresser mixers I went to left me more confused than ever before. I knew I was in over my head when I saw and occasionally chatter with a few of the ultra-feminine women who I could see no masculine traits at all and on the other hand, I knew I was innately more feminine than many of the cross dressers I met. So, I left with more questions than answers.

I was caught in the same place for years as I explored the world looking for myself. Surely, along the way, I found myself in over my head as I transitioned but I kept going anyhow. Too stubborn to quit and waste the new feminine privileges I was working so hard to gain. To use another example, I threw myself into the deep end of the gender pond before I had learned how to swim. I gave myself no choice but to make it. Fortunately, all the mirror time working on my presentation as I wanted to be like the beautiful cross dressers I saw in Transvestia came back to help me. If I could present myself to blend in with the world, it gave me one step up to make it as a transfeminine person.

I certainly was in over my head enough to earn my right to play in the girl’s sandbox, and fill out my gender workbook.

 

Monday, August 18, 2025

Transgender-When Life Throws you a Curve.

 

Image from Chu CHU on UnSplash.

It’s baseball season as we head down to the “dogdays of summer” around here in Cincinnati. As I have mentioned many times, the gender gods allowed me to take my passion for sports with me when I transitioned from male to female. This year, I have been completely emotionally immersed in the Cincinnati Reds professional baseball team. So much so, sometimes I feel guilty about my involvement.

Overall, though, life threw me a real curveball when it came to sports. For several reasons, athletics helped me to keep the bullies away, since I was doing “boy” things. As I played, I found I could not hit well at all, primarily a curveball and resorted to running home to my dresses and makeup to feel better about my failures. And I did, which solidified my deepening idea I should have been a girl all along. Dressing in my pretty feminine clothes certainly felt better than crying in the shower after I committed a key error or struck out to end the game.

As time went on, I faced the reality of non-athletes everywhere, life had thrown me a curve ball I just couldn’t hit. Somehow, I just needed to adjust and become the fan I am today and quit being a victim. I think perhaps it was my Army duty which took any idea of self-pity away from me. So what if my draft number was twenty-three, I would just have to enlist for three years to make the best of it. Plus, the entire routine of basic infantry training took any idea of being a victim away from me. At least I was not one of the guys crying on the night bus to Ft. Knox in the middle of a Kentucky winter. Somehow, I would have to make the best of a situation I did not want to be in.

It turned out, that idea carried right over into my gender dysphoria. The older and more experienced I became as a transgender woman, ended up clashing with my increasingly successful male life. Life had thrown me a gender curveball, and it was not fair but the problem was mine to deal with.

Initially, I kept striking out on my path to transgender womanhood. I was woefully unprepared for the world I so desperately wanted to enter. The path was quite dark with many bumps and curves, so I needed to be careful with the high heeled steps I was taking. Perhaps the most important problem I faced was when I was completely outed as a man in a dress was quickly going home and attempting to figure out what I was doing wrong. Was it my fashion, or my makeup, or what?

This time I refused to be fooled by a gender curveball and hung in there until my life began to change for the better. Slowly, I was being accepted as my true transfeminine self in the public’s eye. I was not hitting any home runs yet, but I was making contact with the public and was successful.

Incredibly to me, the more contact I was making, the more I needed to make. In particular, women were curious what I was doing in their world and drew me into conversations which were uneasy for me in the beginning. Life was throwing me curveball after curveball, and I became halfway decent at making contact with the strangers I met. I think too that after the public met me, more than a few of them reacted to the fact that I was a person who was living with their truth. Then I needed to catch up and respect myself for living my truth. Which was difficult for me to do for years.

Ironically, at that point, I went to work for a company which would not accept any of their successful managers being victims. I carried their training over into my real life and was better prepared for any and all setbacks I encountered. I began to see my supposed setback in life just could be a positive if I made it one. Not so much different than when I went to Army basic training wondering how I was going to make it without my cross-dressing crutches.

After immersing myself in the world of cisgender women, I came out as a better person. Certainly, well rounded in how the two main binary genders interact with each other. I could not ever make it as any sort of an athlete, but it turned out I could as a transgender woman. A journey I came to respect many times along the way.

 

Thursday, August 14, 2025

You Make a Terrible Woman

 

JJ Hart on left. New wife Liz on right.

As I was initially coming out of my intensely lonely and dark gender shell, I dealt with quite a bit of guilt. Especially when my wife called me a terrible woman. I initially thought she was referring to my looks, which she told me she wasn’t.

My second wife was also fond of telling me coming out was all about me which as I look back on it, she was right. My transition was all about me, and I was completely immersed in it. Every time she even made the slightest move to interact with me, I shunned her as I was scared, she was just going to be negative. To be successful, I needed to do it alone it seemed.

I am sure the progress my wife saw in my overall presentation made her feel insecure about the future of our marriage. No matter how guilty I felt about the journey I was taking without her, deep down I knew I had to stay on my path if I was ever going to have a chance to achieve my dream of living as a transgender woman. Which my wife was dead set against.

As I progressed on and on the guilt grew, I was having. Here I was jeopardizing a good marriage, family and job just to wear women’s clothes and makeup. My problem was, I was still refusing to accept the truth about myself. In other words, my desire to be a woman in any sense of the word ran much deeper than just looking like one. When my wife told me I made a terrible woman because I hadn’t paid my dues past looking like one, I knew somehow, I needed to set out to learn what she was talking about, regardless of the guilt involved. To survive, my transition had to be just about me, and I stubbornly pushed forward.

The problem was, the more guilt I felt, the worse my mental health became. I did not know who to listen to, the world at large or the person I was closest to. The world at large was slowly coming to accept me as a transfeminine person while my wife was as standoffish as always about my progress. What she did not know was I was making the strides needed to prove I was not a terrible woman and in reality, a fairly likeable one. Or at least I was trying to.

Time marched on, and my guilt increased to the point where I committed suicide or tried to. When I failed, the entire self-harming episode left me with further problems with my guilt and mental health, so I sought out therapy. Fortunately, I found a good therapist who understood depression and the transgender community, and my life began to improve again. My therapist told me it was alright to feel guilt about the gender transition process and sometimes you must leave loved ones behind so you can live. Beyond all of that, she taught me extreme gender dysphoria was difficult to deal with and before long, our in-person meetings at the Veteran’s Administration were between her and my authentic self. What a relief!

My guilt subsided as my joy increased in my life. Sure, I still had rough spots to contend with, but with my overall knowledge of the world and what to expect, I knew I had finally overcome my fear of actually “making” a terrible woman. In reality what happened was I had the chance to live my way through what my wife told me and in addition. I was not making anything. I already was a transgender woman and had always been. I was just guilty of trying to hide it and internalize it too long. Surely, it was all my fault, and I never had the chance to apologize to her because of her untimely death from a massive heart attack at the age of fifty. I wanted to show her I had paid my dues in the world, and, at the least, I hoped we could be friends. Actions speak louder than words and I know she would never back off from saying I made a terrible woman and in turn at least like the new me.

In life, we rarely have a chance to make a second impression, and it has been nearly an impossible one for me since most of the people I knew as a man (that mattered) had passed away. I needed to concentrate on the new acquaintances I met as a trans woman who never knew my old male self who in his own way had passed on also. Since I did not have a difficult time making and keeping friends in my new life, I must not have been a terrible woman after all.

Monday, August 11, 2025

Buckle Up!

 

Alpha Gatekeeper Hope
Who Let Me In!

If you are a transgender woman or trans man and you have been transitioning along your gender path for any length of time, you know there are plenty of highs and lows to prepare for.

I know on my gender journey; I have had to buckle up for many rough roads ahead. I have many examples I write about often such as being told to leave one venue I started to go to when I decided to leave the gay bars behind and go to mainstream straight venues. I went home in tears like when I was laughed out of malls by groups of teenaged girls when I first attempted to go out in public. For a long time, I never thought I had a chance of living my transgender dreams at all.

Deep down, something told me to fasten my seat belt and keep trying to succeed. You see, the problem was all along in my life, if something went wrong, I ran to my skirts and put on makeup to make it go away. In these cases, I had nowhere to run, so I had to get it right. I was in a corner, and I couldn't get out without a lot of work. It turned out to me, the whole process was a labor of love, and I felt good going forward on my gender path. The problem was I was still quite naïve about what I was facing and thought success could be found if I just was able to present properly as a woman. To try the new world out I was in, I went to all sorts of different situations. Examples were when I went to a downtown festival and an outdoor concert just to see if I could. Following painstakingly applying my makeup and choosing just the right clothes, I managed to be successful at both, and my confidence soared.

When I did, my frail confidence was shattered again when I learned the world was curious about me as a transfeminine person. It meant I would have to really buckle up and do more than trying just to look like a woman, I needed to communicate like a woman. All of that turned out to be harder than it sounds (no pun intended). I found out quickly that women operate on a different wavelength than men. Men use a more simplified straight forward approach to communicating with each other and other women. On the other hand, I discovered I better refine my listening skills, plus be aware women communicate with each other on non-verbal wavelengths. Also, eye contact with other women became very important too, if I was ever going to be allowed to play in the girl’s sandbox by the alpha female gatekeepers.

As with anything else, I needed to allow practice to become perfect if I was ever going to succeed at reaching my goal of living as a transgender woman. To do it, I needed to forget my unreachable dream of being able to present so well as a woman that anyone would ever think I was cisgender. To begin with, testosterone poisoning had taken all of that idea away from me. I needed to re-buckle up my expectations and know the best I could do was follow my path as a woman from a different background. To succeed, I needed invitations from cis-gender women to their girls’ nights out so I could observe and learn how other women acted when men were not around. Naturally, I needed to put what was left of my male ego behind me when I had to buckle up and attend several of these meetups. My primary example came one night when I was invited along with a group of servers where I went to, to another upscale venue to party. They were all young and attractive and immediately were surrounded by attentive males, leaving me by myself and my drink. I learned a powerful lesson that night why certain attractive women tend to hang out together.

I was fortunate as I traveled my gender journey, I had key alpha females to help me with my seatbelt. As an example, I have added the picture of “Hope” who ironically gave me hope for my future dreams. She was the first bartender I ever met who went out of her way to be kind to me, all the way to introducing me to her lesbian mother who I stay in touch with to this day. Hope led the way for me to be accepted by others and thrive in the girls’ sandbox, and I will never forget her for it.

My main message is, no matter how many bumps and bruises you may suffer along your own gender journey, just try to securely fasten your seatbelt and make the trip as interesting as possible. Just remember, not many are able to make the same journey and achieve their dreams of living as a transgender woman.

 

 

 

Thursday, August 7, 2025

Jocks and Dresses

 

Image from Norbert Toth
on UnSplash. 


As a youth growing up, I found myself embracing the world of sports to cover up any lingering feelings of wanting to be a girl. Plus, being a jock of any kind helped keep the bullies away when I needed it the most. Why would they think a defensive end on the football team would ever want to be feminine in any way?

Little did they know, the time I spent longingly looking over to watch the cheerleaders practice was much more than admiring their short skirts and tight tops. My desire was in no way sexual; I did not desire any of the cheerleaders that way, I just wanted to be them. Happily, my cover worked and to the outside world I appeared to be a “normal” boy with normal hobbies such as sports and cars.  

It was my rendition of having my own gay beard as described here on “Wikipedia”: “Often, the term was used in the early to mid-20th century, used by homosexual individuals to conceal one's sexual orientation through the disguise of a heterosexual relationship.” I was not gay but needed sports to conceal the fact I was a cross dresser. My “beard” worked and got me through school very much unscathed. My gender closet was secured.

I was able to play football until I was hurt twice in my junior year and there was no place on the team for an injured slow defensive end and no matter how much dreaming I did, I could never make it as a cheerleader either.

Along the way, my love of sports became ingrained in me as much as the desire to be a transgender woman. If I can describe the love of sports I had, it was like a big set of luggage I was carrying from one gender to another when I needed to figure out what I could take with me.

It was about that time in my life when I was leaving my gender closet and looking around, that I began to see other women who shared my passion for sports. Just maybe, I could drop my beard and bring along what could be one of the most important pieces of baggage I had in life. If I was careful, and set myself up of success, it could quite conceivably be me as the woman at the bar watching her favorite team on one of the big screens. While I would not be a jock in a dress, I could be one in a football jersey.

Even better was when I was able to befriend a couple other cisgender women who were sports fanatics like me. We would get together often to watch games and harass each other when our team lost. It all led me to one of my proudest moments when I was invited to a NFL Monday Night football game in Cincinnati. I was still quite new to the world as a transfeminine person, so I was very scared, but I accepted her invitation to go. I had made the big time in my quest to have brought my passion for sports with me into my transgender world. Except for my team losing, I ended up having a great time and the whole experience really built my confidence in my new life.

While I never became exactly a jock in a dress, I did become one in makeup, leggings and boots. All along, I had my doubts about where my journey would take me and how I could get there. But I never missed most of the male baggage I needed to leave behind as I embraced the transgender future I was looking at. Maybe I was fortunate in that the world around me was catching up to an expanded role for women in the world as I was entering it. Whatever the case, it made my transition so much easier.

Also, I did not do it by myself, I had women friends to show me the way. They just happened to share many of the same interests I did. I mention them a lot, but I would feel bad if I didn’t give credit where credit is due.

Plus, from the comments I receive, I know I am not alone in utilizing sports to use as a “beard” in your life to cover up your gender issues. I remember one comment from a reader saying she used football shoulder pads to cover up the gynecomastia breast growth they went through early in life. Proving for many of us experiencing gender issues, hiding them can take many paths.

 

Tuesday, August 5, 2025

Is Purging Just a part of a Trans Journey we Need to Go Through?

 

Image from Shayan Rostami
on UnSplash. 

I received several wonderful comments to my “Purging” post yesterday including people such as Jeanie who has had gender issues for years such as me.

Here is the comment and we will go from there: “I just purged last Thursday. I wanted to see if there was a strong enough "desire to reacquire". I'd go months with the stash behind insulation in the basement under a bay window without dressing. It might be I was too chickenshit”.

Thanks for the comment! And it got me to thinking about all the ways we cross dressers or novice transgender women went to hide our small collection of feminine wardrobe and makeup from our family. As a kid, I even went as far as hiding my stash in plastic garbage bags in a hollowed-out tree in a neighboring woods. Where I hoped no one would ever discover it. In addition, I had two other small hiding places in the house I could go to if I was suddenly free to cross-dress in front of the mirror. The entire process added to hiding my gender issues in plain sight. Almost, as all along, I was desperately trying to escape being caught and being sent on an unpleasant trip to a psychiatrist who would have most assuredly pronounced me mentally ill. Which was the norm for mental health professionals back in those days.

Since I never completely purged my feminine stash ever, maybe I was too chickenshit to do it (as Jeanie said). Or, as I struggled throughout my life with gender issues, my own “desire to reacquire” would return to rule my life. As it turned out, I was never strong enough to purge totally. Which looking back should have given me a clue to who I really was, a woman cross dressing as a man. Deep down, I knew, every feminine item I had worked so hard to acquire could not so easily be thrown in the trash. It would ultimately come down to me wondering how much different I would look in the mirror if I had not thrown out my previous stash.

At first, it all got worse before it got better when I entered my strong going out in the world as a novice transgender woman with my second wife. Fortunately, when I was restoring the old house, we lived in, I was able to build in a closet we rarely used. So, I found a place to hide the many thrifts store finds I had made and purchased. Also, by this time I was in a place where I did not care what my gender foes thought. I was building my future public persona, so I needed to look my best. Essentially, I entered the “don’t ask, don’t tell” phase of our relationship when my wife never said a word about my increasingly large wardrobe. She knew, I knew I was never going to purge again. Which turned out to be not true.

Just before she passed away, I decided to throw away “most” of my wardrobe and makeup and even went to the extent of growing a beard. Which I considered the ultimate purge. Even as I did it, something told me to keep my favorite outfit, wig and shoes because I never could be sure when I would need my old friends again. Tragically, six months later I did when my wife passed away and I turned inwardly to my feminine soul for comfort. When I did, I was able to shave my beard and hit the ground running towards a new life. Or, should I say, heels on the ground.

One way or another, I was happy I was not strong enough to totally attempt to purge away my feminine life. It was time to open a new chapter, even if I was sixty, as a transfeminine person. It seems many of us, with gender issues are doomed to a life of denial. We try to sooth our transgender or cross dresser sides by trips to our mirrors until we are caught, or in a relationship which even makes it worse. We begin to feel guilty about many things such as forsaking our ingrained male habits, all the way to feeling selfish for wanting to do something as radical as changing our genders for ourselves.

A lifetime of purging falls right in line with all the other pitfalls we encounter on our gender journeys. We must be strong enough men to make it to transgender womanhood and purging is just another experience we have to go through.

As always, thanks for reading along with my writings and experiences! Your comments mean a lot to me also. They help me to know if I am headed in the right direction. Please keep them coming!

 

 

Sunday, August 3, 2025

Purging

 

JJ Hart from back in Ed's and Michelle's
time.

For many transgender or cross dresser women, rarely have we lived a life when we never wanted to go back to our male selves. A common term for the practice is called “purging.”

Like many of you, I have experienced my share of trying to purge away my gender issues. About the time I thought I was entering a high-profile stage of my feminine life, I began to feel guilty and wanted to throw it all away. Then, I learned there were different stages of purging. For example, when I was purging, I never could seem to throw out or give away all my hard earned, cherished feminine wardrobe and makeup away. Deep down I always left the door open to my closet for a return to cross dressing as I called it back in those days.

Then there was Ed, an acquaintance I had who really defined purging to me. Ed was a frustrated cross dresser who at the least was having problems with his family and at the same time dealing with several very serious health problems. Before he reached a crisis point with his health problems, he decided to give away all his cross-dressing items. With Ed, that meant a lot. He needed to empty out an entire storage unit he rented to hide his wigs, wardrobe and makeup from his family. I turned out to be on the receiving end of his gifts. He gave me a nice set of silicone breast forms he purchased as well as a plastic tackle box full of expensive makeup.

What ever happened to him I will never know, the last I heard from him was decades ago when he was increasingly becoming more and more negative concerning a transgender friend of ours. Michelle was very beautiful and was headed towards gender realignment surgery, and I think Ed had developed deeper feelings for her than just friendship. He never confided in me if that was the case which leaves me to yet another unclosed mystery in my life. Along with what my deceased wife would have thought of me if she ever knew me as a more complete transgender woman.

Even as I continued to progress along my transgender path, I found myself to be a contradiction of terms. I did not know for the longest time how I fit in on the gender spectrum. I had an idea I was more than a casual cross dresser such as Ed was but was I as serious about becoming a fulltime woman as Michelle was. Being in the middle as always tortured my frail mental health as I did not know which way I wanted my life to go.

Initially, I decided I could take the pressure no longer and purged my feminine fashion and makeup…almost. I compromised and did not throw out my favorite wig, sweater and Ed’s silicone breast forms. So, I had left the door wide open to return to a life I had always thought deep down, I could never leave behind. Slowly but surely, I rebuilt my wardrobe, added another wig and purchased new makeup to fill Ed’s tackle box I still owned.

That was the last time I tried to purge my physical belongings, helping to calm my transfeminine longings down. Following the many times in life I attempted to purge my life away from my deep-seated gender desires, I finally learned that I could not easily throw my real life in the trash. I also lost track of Ed and Michelle long ago and the last I heard from Michelle was she had gone ahead with her gender surgeries and was living with a lesbian in nearby Columbus, Ohio.

I just wish I had the foresight to understand how close purging was to my overall wellbeing than the obvious. All along, I thought I was trying to rid my feminine self of her external possessions when in reality, I was proving the futility of trying to deny the person I was always destined to be.

In a full circle moment, I was able to grow my own breasts thanks to gender affirming hormones or HRT and donate my silicone breast forms Ed gave me to a swap out at a transgender-cross dresser support group meeting I attended. As I mentioned, he had very serious health issues, and I doubt if he is still alive today. In a moment of clarity, I remembered his full name and searched for it on Facebook to no avail.

One way or another, I view purging yet another unique sideline of following a gender path. As far as I was concerned, I not so slyly resisted completely throwing away all of my wardrobe, shoes, wigs and makeup I acquired. I never knew when I would go back, I just knew I could.

Friday, August 1, 2025

Life is too Short

 

Image from Brian Wangenheim 
on UnSplash.

Time is a precious commodity and life is too short.

Days, weeks, months and years are especially precious for many transgender women and transgender men. Mainly, if you waited until later in life to break out of your gender box and transition. Which is what I did.

I could and did look at my cross-dressing years as practicing for the big event of coming out as a transgender woman. While I improved my overall skills in wardrobe and makeup basics, there always seemed to be something I was missing. Actually, there were two main things I was missing, not just one. The first one was the realization I had my idea of cross-dressing backwards. I was never a man cross-dressing as a woman, I was a woman cross-dressing as a man. The second major realization was I would have to go through several transitions to meet my goal. An example was, I needed to transition from being a cross dresser to being a transgender woman if I was ever going to make it to where I wanted to go as a transfeminine person.

To accomplish my dream, I needed to take my second wife’s advice and set out to learn what a real woman went through in life. There was so much more than just being the “Pretty, pretty princess” as she called me. The problem was, she was always my feminine gatekeeper when I tried to explore the new and exciting world I was seeking. She did not want me to make it. She was a strong person and made it tough on me to progress in any way on my gender path but still I persisted.

Time went on and the years passed me by as I went to transgender-crossdresser parties and mixers to see what I could learn. Even then, when I hit my forties, I had a sense of desperation as time went on with me, and nothing major was happening on my gender front. It was during this time of my life when I started to escape my closet and explore the world. Mainly, I was carving out a totally new life where people knew nothing of my old male self. I was free to be the new me I wanted so bad.

After I went through the darkest period of my life when I lost nearly everything and everybody who was near and dear to me, did my life come full circle, and I began to notice the light at the end of the tunnel was not the train. My guess is I had paid my dues, and destiny was opening its doors to me. Among other things, it was about this time that the Veteran’s Administration health care system approved providing gender affirming hormones for veterans such as me. I jumped at the idea of taking advantage of less expensive HRT medicines and free mental health care. Even though I had already set up my hormonal medications through a civilian doctor.

By this time, it was becoming increasingly evident to me which direction my life would have to take before it was too late. I was in the middle to late fifties of my life and if I ever was going to ever have the courage to jump off the gender cliff, I would have to do it. One thing I did not want to do was continue to live the part-time gender existence I was already living. Plus, I was rapidly nearing the point in my life when I could take early retirement. Which would preclude me from having to go through any ugly transition on the job scenarios. I worked in a very male dominated profession, so switching genders on the go could have been quite challenging.

Finally, one night when I was out to be alone, I decided I was enjoying myself so much, I needed to end my gender turmoil forever. I decided to forsake all my male privileges I had fought to earn for decades and seek out my dream life as a transgender woman. It was not a decision I took lightly as I sent all my male clothes except my Army uniform to the thrift stores which were so beneficial to me when I was first acquiring my transfeminine wardrobe and fashion.

By this time, I was sixty and I figured I would never have a better chance to transition again. I took advantage of all the feminine “practice” I had done over the years. I was able to hit the gender ground running and never looked back.

 

Thursday, July 31, 2025

Why Not Me?

 

Image from Buddha Elemental 3D
on UnSplash. 

My life has been a series of why not me moments.

As a boy growing up in Ohio, I always wanted to be a better athlete, which turned out to be an impossible quest because there always seemed to be a better athlete in my world to take my place. Then there was my attempt to be more social in the world, but I was incredibly shy, and it was so difficult to do. So, I ended up hiding at home, thinking someday I would grow out of my shyness.

My greatest why not me moments came as I struggled with my gender identity. It became so bad with me that when a stranger asked me what I was going to be when I grew up, the only truthful answer I never gave was a woman. I internalized my thoughts and somehow hoped they would go away. Which of course, they never did. They just got worse because the main problem I had was wondering if I could do it at all. Information was incredibly difficult to come by in my sheltered male privileged world and for the most part I was lost, and I continued the path I was on. Doing my best to live a male life successfully, and at the same time, steal away moments of privacy to cross dress in front of the mirror.

Often, much to my surprise, I was semi-successful at both. I kept my increasingly gender fluid life in balance by improving my mirror image away from drag clown to beginning girl, while at the same time, keeping the bullies away from me by having an interest in sports and cars. I even went as far as dating a few girls in high school where I ended up attending both my junior and senior proms. Little did anyone know I wanted to be the one wearing the pretty gown and getting the flowers. As with the rest of my life, I got over it and moved on, no matter how difficult it was. Why not me was not working, I was still stuck in my gender quicksand and there was no handsome cowboy coming to help me out. Or strong woman as it turned out.

When I finally had had enough of being a gender victim, I opened my closet door and looked around for the first time in my life. I knew I needed to move past the once-a-year Halloween parties I was attending as my novice transfeminine self and try more ways to get out into the world to see if I could be successful or would my dream of life as a woman always must be a dream. I was ever so cautious as I began by shopping in malls and bookstores which turned out to be low impact areas for novice cross dressers or transgender women. I went to places where my money was more important than my gender which gave me the confidence to do more. More meant testing the public with new and exciting ideas such as stopping at restaurants to eat to see if I had any push back at all. I did not and moved on. Maybe, my why not me was coming true after all.

Sadly, dreams being dreams are not so easy to achieve I found out. Especially in the world of gender change. There was no way I could gloss over all the nuances of being a true transgender woman would entail. Many times, I ended up getting my new high heels stuck in more quicksand than I could have imagined and was fortunate to have found my way out, which I have written about in several blog posts. It occurred when I suffered the loss of male security privilege. However, by this time, I was able to take the good with the bad which was beginning to lessen, and I could see my dream being reality.  Which I had never thought possible.

For the first time in my life, I was beginning to live my why not me moments. I was at the threshold of living the life I had always wanted. Free from the male shackles which had tied me down. Sure, at times, it was unbelievably confusing to do, but with the help of a few women friends I always mention, I made it and was able to get out of the quicksand all together and rebuild my life.

Today, I am a woman who happened to come from a different background than most. But it was my dream to make it, and I did. As I said, I never thought I could or would.

 

 

 

 

Monday, July 28, 2025

Dealing With Severe Escapism


Image from Ludovica Dri
on UnSplash.


Severe escapism has been part of my life for many years.

It all goes back to the humble beginnings of me exploring my mom’s clothes and makeup. The entire process helped me to escape from a male life I never wanted. What never occurred to me had how quickly I escaped would become reality as I kept going back to my cross-dressing beginnings to seek guidance from the mirror.

Problems began when I began to listen to the mirror completely. It was telling me I was an attractive woman but was I really and ready to prove it to the world. When I switched out the mirror for the world, I quickly learned I had a long way to go in my heels to do better in a feminine world. What turned out to be a short trip really kept on going into a major lifetime of escapism.

How did I know I was escaping? Primarily it started when I began to feel so good as my novice transgender self. I thought, how could I feel this good and natural if I was just escaping. It was at that point when I seriously started exploring the possibility of living out my dream of eventually living out my life as a transfeminine person.  

Increasingly, I discovered my dream was a reality if only I could sever my ties with my escapism I was suffering under. No more could I run home to hide behind my skirts if I was so completely exploring the feminine world. Whatever was going to happen just would. What happened was I did not have to escape nearly as much because I was increasingly enjoying my journey into transgender womanhood. Again, because I could not run and hide when someone tried to interact with me. I even was able to conquer my fear of the “mean girls club” as I not so fondly call the so-called gatekeepers of femininity. Perhaps conquering is too strong a term. Put up with maybe a better one. The mean girls may not have liked me but found I was going nowhere.

As I no longer had to resort to so much escapism, I began to look for better ways to live my new life. I started to see new colors in the world as the gender affirming hormones (HRT) in my life began to take control. My senses heightened to a point where I could sense the world as well as the cisgender women around me. I learned women were really cold all the time I thought they were making it up, is a prime example.

It was increasingly a very rare occasion when I needed to revert to my old male life to take advantage of a male privilege such as taking my car in to be repaired. Even though I have needed to conquer that fear, I still have nagging problems with doing anything auto related to this day. Outside of that, I have overcome most of the problems I faced which sent me home hiding behind my skirts. Even my mirror has become a noncombatant in my life. I see myself for whom I really am. No better, no worse and I work from there with my makeup.

To be sure, running away from my gender issues did not improve my life. I continued to switch jobs and locations as I tried to escape my true self. It was not until I landed a dream job in my hometown did, I had to stay put and quit running. For all intents and purposes my escape route was destroyed. For a while, channeling all my gender issues into my work proved to be a wise choice as I made it nearly to the top in my field. Hear I was, with a good marriage, family and job, while all along something was still missing. That something was I still had the nagging idea something was still missing from my gender identity. I was still living a lie and found it increasingly difficult to run anymore from the idea.

In many ways, tragically, escapism would work for me as I became the last person standing in my small group of friends. They all died including my wife of twenty-five years, so I needed to start all over again. As they say, when one door closes, another one opens. Which is all well and good if you can find the door. Destiny paved the way for me to make the final gender transition of my life away from the male road I was on. For every tragedy which I so poorly faced, I discovered a person to help me rebuild, and that person is my wife, Liz.

With the magic words, she had never seen any male in me at all, I threw all caution (and him) to the wind along with all my male clothes and closed out the portion of my male life I had fought so long to do away with. My only regret? I selfishly would like back all the time and energy I wasted on fighting the inevitable, it was always time to allow my transgender woman to live. She was tired of not being allowed to do anything. Escaping was over.

 

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 thi...