Showing posts with label drag. Show all posts
Showing posts with label drag. Show all posts

Tuesday, April 7, 2026

Everything Was Fine Until It Wasn't

 

Image from Danny
Messina on UnSplash

Many times, when I was sailing along thoroughly enjoying my feminine self out in the world, I would come to a rude awakening that something was not right. As I experimented as a novice cross-dresser fresh out of the mirror at home, I learned any number of things could be wrong. Including the cruel imposter syndrome which haunted me. A great topic for another blog post.

Or maybe my makeup was not on point, and I looked like a clown in drag, or I had that old male scowl on my face instead of a pleasant little smile which gave away the fact I was not enjoying myself the way I should. But something was wrong as I was doing what I wanted to do for a change, and I needed to show it. Not revert to my old male ways of trying to scare people off before they even started to interact with me. It is something I work on to this day as it is easy for me to fall back into old gender habits. I needed to work hard to put my entire new feminine image into play when I was out or no matter how good my makeup and fashion looked, I was not going anywhere in my development as a transgender woman.

A quick example of the problems I was facing with my face happened one day when I was out shopping in a woman’s clothing store. When I came around a rack of clothes, I was startled by a young girl staring up at me. Worse yet, I was prepared for the worst when she took off looking for her mother. I was semi-relieved when I heard her say, look at the BIG woman, and I thought she had that part right. Until she said, the BIG MEAN woman, and I immediately felt bad that she thought I was mean. From that point forward, I put a slight feminine smile on my face as my final touch of makeup. Everything was right with the world that day (including the little girl who thought I was a woman) until it wasn’t.  Lesson learned.

Changing the way, I looked at the world with my face was just the beginning of improving my overall presentation in the world of ciswomen, young and old. Early on, I paid quite a few brutal dues when it came to encountering groups of teen girls in the malls I went to. We all were in the process of discovering our femininity, and the girls took their humor out on me vocally and it hurt but the process helped me to develop myself to a point where I could better blend in with the new world I was trying to conquer. I just had to learn to conquer in a different way than I had ever had to before. I could not just hope to bluster my way through life as a man which I had gotten used to, I needed to finesse my way through until I began to feel the benefits of female privilege past the occasional man who opened a door for me.

Everything was fine, until I learned I was just getting started on my dream to live a transfeminine future. I had no idea how complex a woman’s life could be with a passive aggressive future in store for me. Plus, a future where for a change, to survive with other women I needed to completely listen to what they were saying and make sure I looked them straight into the eye, so I did not miss any nonverbal communication which was coming my way. Several times, I was helped out of potentially dangerous situations with toxic men by paying close attention to the nonverbal cues being given to me by concerned women with much more experience than me.

For the most part, this time of my life, in my thirties and forties , everything was fine with the gender juggling act I was attempting until I pushed myself too hard, challenged my mental health and continually got in trouble with my second wife who caught me trying to sneak back into the house after a night of living as my newly thriving feminine self. At that point, massive fights occurred which ended with me trying to promise I would never go out again. Which I knew would never happen. Once I had seen the world from my vantage point of a trans woman, deep down I knew I could never go back to a completely male life. I think my wife knew that too and that is why the fights we had became so vicious. Particularly when she told me I made a terrible woman because (in my words) my gender workbook was not filled out, and I had not paid my dues. Which was exactly what I was doing when I went out to live. I was sad I couldn't share my new knowledge with her but it was just not meant to be before she suddenly passed away.

After she died, nothing was fine as I was intensely lonely and needed a shoulder to grieve on. I found that shoulder in a predictable place and she was there all the time, my transgender self. When failure was not an option in my life, all the lonely nights I spent exploring the world around me with other women proved to be an invaluable experience when I learned I did not “make” a terrible woman after all. It turned out, I did not “make” anything at all, I just found my way to a place I always should have been, and everything turned out of be fine and I could take the wasn’t away from it.

I was even happy for the first time in my life as the heavy expectations of a male life I wanted no part of were removed for good. Being free to be the true me was the best move I ever made and my only problem was I did not do it sooner. Everything was fine, it was just hidden from me by myself. When revealed, I was free to never look back.

 

 

Sunday, March 29, 2026

The Winds of Gender Change

 

Image from Taylor Flowe
on UnSplash. 


Per normal, we have had a very windy spring here in southwestern Ohio USA. For some reason, I have never associated spring with my gender changes like I have during the fall season. I remember vividly the fall evenings I spent driving around feeling melancholy about the fact that I was stuck in my old unwanted male life. Seemingly, forever. Maybe it was because of the trees losing their leaves which set the fall off from the spring. I just knew it was happening.

Fall was especially bad when I was on a six-month delay to go to the Army basic training at FT. Knox, Kentucky. It marked the time for me that I knew I would have three years away from my gender cross-dressing activities which kept me sane at the time. I was afraid of going to basic infantry training as well as losing my ties to my feminine self for the next three years. The only reality to me was that I had no choice but let the winds of change take me away to a new uncertain future.

When I was in the service, my theme song began to be “Call Me the Breeze” by Lynard Skynyrd because of all the moving I was doing from the US to Thailand, to Germany, I was truly able to feel the wind thanks to the efforts of Uncle Sam and his military. I did it so well that I was even offered a promotion if I stayed in an extra year, which I turned down. Instead, I got out and resumed my civilian life at a small radio station I worked at before the winds of gender change got the best of me, and I started to follow my instincts and began to explore the world as a transgender woman. Which was becoming increasingly evident to me was where I fit in in the gender spectrum.

In the beginning, all I had was Halloween parties to express my femininity and even there, I was not doing a good job of doing it. I was stuck trying to do a trashy look when in fact, my inner woman was pushing for a more realistic approach such as being a professional ciswoman. What did happen was, I got the basics of what it would take if I ever threw caution to the wind and went across the gender border from male to female. It was at those parties that I found that all of a sudden, the other women wanted to talk to me while the men left me alone which would be a theme for my life as I transitioned.

Once I left all the Halloween parties behind me, I started to attend small diverse LGBTQ mixers in nearby Columbus, Ohio. When I did, it was as if there was one of those huge Hollywood movie fans at my back pushing me forward. From lesbians to transsexuals, all were there so I could judge where I would be if I moved forward in the world. Due to the fact that I was still solidly married and had a very good job, I needed to shut the fan off, or at least put it on a slow speed so I could catch my breath and figure it all out because of the gender complexity it all presented. Did I want to give up my life of male privilege to be a trans woman, at that point in time I was undecided.

It turned out, indecision was my worst enemy as I entered the world to explore it as a transfeminine person. Most of my ventures were ill-advised attempts to be accepted in gay venues in Dayton, Ohio where I was barely welcomed and when I was, it was because they thought I was another drag queen. Which was far from the truth. It was not until the winds of change blew me through the doors of the same sports venues I enjoyed as a man did my world began to turn around for the best. To my amazement, I earned my acceptance in those places easier than the gay bars I was going to, or the lesbian bars which were closing due to lack of business. Before I knew it, I was treated like a regular. Even with the restroom privileges I needed so badly.

I was flying high until the winds of change dictated a change and I crashed to earth when everyone dear to me began to pass away in a two year period. Including my wife of twenty-five years. I was in shock and so lonely I drank too much and took unnecessary chances with my life as the winds of change continued to blow strongly. Every time I thought the winds were receding, they would pick up again threatening to blow me off my high heeled shoes.

I was fortunate when I saw the name of a doctor who would check me out and then prescribe HRT or gender affirming hormones and I took immediate advantage to do something I had wanted to do for a very long time. Sync up my inner person with an exterior which was feminized. Even with the minimum dosage I had to begin with, I could feel and immediate change in several areas such as with my emotions and breast growth. When I began to see myself as a different femininized person in the morning mirror, I was becoming more and more excited over the winds of change which were pushing me ahead into a new exciting world.  

The only part of my being who was not surprised by all the changes was my feminine self who had been hidden away all those years with no way to express herself as when she was in the Army. If patience is a virtue; she had it all as my male self-put on a tremendous fight to maintain what he had earned as far as privileges went. Fortunately, the winds were blowing in the right direction, and she won the ultimate battle for my life. I discovered that without her, I would not have had a life worth living.

 

 

Tuesday, March 24, 2026

Imagination or Knowledge

 


JJ Hart. 

In the very beginning of my transgender journey, I often wondered if it was all just part of my very active imagination. Perhaps it was all part of me secretly hoping all of my gender issues would magically go away.

Of course, my gender dysphoria never went away until much later in life when I faced up to it and all I was doing as I viewed myself in the mirror cross-dressed as a girl, was slowly instill the knowledge my trans desires were not going anywhere. In fact, back in those days, the transgender term had not even been invented to use at all. I was living in the pre-internet “dark ages” of information. All I had was the well-worn issue of “Transvestia” from Virginia Prince to connect me at all to the world of people who had the same gender issues as I did. Closets were impossibly dark and lonely back then.

It took the knowledge of my situation to finally break into the light and see the world as a small part of who I really was. I finally used my issue of “Transvestia” to locate nearby mixers which were headlined for heterosexual transvestites only. If that was true or not, I found a diverse mixture of people attending which ranged from beginning cross-dressers all the way to impossibly feminine transsexual women heading for gender surgeries. The frustrating part for me was that even with the choice of individuals I felt close to, I could not find a group to hang out with. I was frustrated that I had come this far to still feel this completely different. The light was there, but it was very dim due to my complete misunderstanding of who I really was.

The one fact I was waking up to was that none of what I was feeling was my imagination. My gender issues ran very deep and would be very difficult to solve. As I always point out, since I was so busy being an active man at the time, the conflict was real. Once I realized what I was really battling. On the plus side, about this time, the internet became part of my life, and I was able to see and even reach out to others like me. It was all well and good until my second wife, who was more computer savvy than me, caught on to what I was doing and tried to stop me. After I used my imagination to find ways around her, I was still able to build knowledge of what it would look like if I was actually able to enter the world as a transgender woman.

Once I began to really explore the world as a novice transfeminine person, I really had to use my imagination to succeed in getting out every spare moment I had from work. I would purposely schedule myself off from my work on the days I knew my wife was going to be working late just so I had free time for exploration, is a prime example. In that case, imagination became knowledge as I actually began to explore what I needed to explore behind the gender curtain. Even to the point of making new friends who had no knowledge at all of my previous male life which I was trying hard to do away with.

More importantly, as I sat myself up for success in venues I really wanted to be in as a woman, imagination further faded as knowledge sat in as I was able to fill out my gender notebook. No more gay venues for me where I was treated as a drag queen and even ignored when I tried to order a drink, all the way to be treated as a regular where I wanted to be was the knowledge that I needed to succeed further.

During this time also, I spent a lot of time soul searching about if I was doing the right thing about attempting to femininize myself even more with my new lifestyle and going even further my seeing it I could be approved for HRT. Mainly because I felt so natural as my feminine self among ciswomen, I thought I would take the path of least resistance and continue building knowledge of taking the gender leap I was considering. In essence, I was taking all the imagination that the young girl in front of the mirror away and replacing it with the knowledge of what I could expect living as a fulltime transgender woman. I needed all the knowledge I could get because the risks in jumping the gender border were so great. It all meant saying goodbye to all the male privileges I had worked so hard to build up. Not to mention the extra pressure of the possibility of giving up spouse, family, friends and employment as I knew it. I needed to be prepared to burn it all and start over.

What I ended up doing was, hedging my bets a little by making new friends in a new feminine life which I hoped would soften the fall if I decided to jump off the cliff and never go back to my male self. At this point, I always mention all the women who helped me along but somehow, I miss the most important one, my inner female who came through in a big way when she was allowed to run my life for a change. Once I gave her the platform to flourish, there was no imagination of the path she was going to take.  She took the highroad without all the evilness you see in some fulltime transgender women. She just wanted to enjoy her life and be an active part of the world and the LGBTQ community. And she wanted to help others by writing about her experiences.

Which brings me full circle to where I am today. No imagination, just the knowledge of experience to get me by in the world.

 

 

 

Thursday, March 19, 2026

How Much Discipline do you Need

 

Image from Brett Jordan
on UnSplash.



One thing I learned the hard way in my transgender travels from male to female was that it took an intense level of discipline to do it. In fact, cross-dressing as a girl was the first thing I ever did in my life which took a large amount of discipline. School was easy enough and sports were something I always tried at but never excelled at.

Growing up, I was always under pressure from my parents to finish any projects that I started and do them right. That is when the struggle began. I have written fairly extensively about how I struggled with the makeup arts when I first discovered all the makeup samples my mom had stashed in a drawer beside her sink in the bathroom. Using the samples meant I would have less chance of discovery when and if she discovered someone was in her makeup.

The only parallel I always use was how I tried miserably to paint all the plastic model cars I put together. My cars never seemed to come out as well as my friends and I really did not want my makeup to be the same failure as my attempt at modeling cars was. For the first time in my life, I developed the discipline to do something about wearing makeup and I set out to become better at it. Which included being able to purchase the right supplies with the meager amount of money I had to work with. I was under a lot of pressure when I did my own shopping for feminine accessories, so I needed to make sure I did not make a mistake and buy something which made me look like a clown in drag going to the circus.

Little did I know, developing discipline in my feminine pursuits was just the beginning of a lifetime search for a transgender future. Every time I turned around, I faced a new challenge, it seemed like I first went out in the world of ciswomen. Where I needed to be better to just survive. A prime example was early in my life as a novice transgender woman, I had a difficult time of getting out of the mirror and putting a complete feminine image together for the world to see. It seemed as if every time I thought my makeup and fashion looked good, my movements and voice were totally off, and I would ruin the whole image. I just had to develop the discipline to do it all and complete myself as a transfeminine person.

Experience was the only way it happened. The more I went out into the world, the more I learned about if I could ever achieve my trans woman dreams. It was very important to me to explore all my options before I made such a huge and important decision in my life. Before long, I was sneaking out of the house every spare moment I had to live the new life I was carving out as a transgender woman. The problem was, the whole experience was terrifying while at the same time, it felt so natural. Further confusing me on which way I should go with my gender issues.

One way or another, I was developing the discipline to conduct myself in the world of women with my own set of standards. I learned to dress and makeup myself to blend in where I was going and more importantly how to communicate with others around me when I got there. It took tons of discipline to do it. Especially when I was making the mistake of trying to live in both binary genders at once. I needed to force myself to make sure I was projecting the right gender at the right time mainly when I was at my job as a successful man. I can’t tell you how many times customers tripped up and called me “mam” when I was going about my male business. Secretly I was pleased but could not show it. The bigger problem I always mentioned was that the gender ping-pong I was playing took a tremendous toll on my mental health. Switching back and forth was terrible.

The only positive was that I developed more discipline than I had ever had before. When I was a man, I knew I was temporarily holding on to a lifestyle I no longer cared about and when I was a woman, I totally had bought into where I wanted to go with the rest of my life. The only thing left to do was to seal the deal and do it. And learn the fine little nuances ciswomen know how to exist in their world. Like figuring out who the alpha female is and going after her approval. Through it all, I was building layer upon layer of confidence in myself. Which I would need later when the dark period of being extremely lonely set in. The intimidating thought of finding anyone remotely able to partner with again looked very dim until all of a sudden it was not. That is when I found my current wife Liz over a decade ago and she made a believer out of my self again and I could drop all my personal defenses to ever loving someone again.

It turned out that all the work I put into disciplining myself into being a totally different person worked out for the best. I emerged from my work with a newfound lease on life as the transgender woman I had always dreamed of becoming. I proved my parents wrong. I could take on a project and see it through successfully. Just not the one they had chosen for me. I tried once to come out to my mom and was rejected and never to my dad, so I doubt they would have ever approved of what I did. Even though what I did was save my own life by shattering my gender shell.

It took a lifetime worth of work to improve my feminine discipline. Mainly because I was blindly entering a world of ciswomen I knew nothing about as my gender workbook was blank when I started. After making up for lost time, I fairly quickly caught up and entered the world as myself.

 

Tuesday, March 17, 2026

The Power of Allies

 

Image from Peyton Sickles
on UnSplash. 

I don’t know if I could have ever made it to my dream of living as a full-time transgender woman, without the help of strong allies.

There were many times when I had hit a stopping point on my gender path and was clueless on which way to go. Mainly because I was attempting to find myself as a woman so I could continue to live after a failed suicide attempt.

I have several examples. The first of which came when I first started to go out and secretly wanted to find a social life as a trans woman because I was so lonely after my wife of twenty-five years unexpectedly passed away from a massive heart attack at the age of fifty. In the past I had considered myself a social person, and it hurt deeply to be lonely. At first, I went online and tried the usual methods of establishing a contact or two to date but I ran into the usual problems of inviting all sorts of trash into my life, which included many no shows when I had arranged to meet someone in public. Which was the only way I would do it for personal safety reasons.

In the meantime, I was fortunate to escape the gay venues I was going to (where they thought I was just another drag queen) and establish myself in a couple of the big sports bars I used to go to when I was a man. Places where I could drink pints of beer and watch sports on big screen televisions. Ironically, being alone in one of these venues led me directly to my first two powerful allies.

The first happened to be the mother of one of the bartenders who set up a casual date between us one night where she worked. It turned out we got along really well, shared the same interests and set up future dates, so my end to the extreme loneliness I was feeling was looking like it might me coming to an end. I was further encouraged not long after that when one night a woman came in to pick up her to go food order and suddenly slid her phone number down the bar to me, to my amazement. Not long after that, I kept the number and had the courage to call it.

From that point forward, the three of us made an inseparable trio as we watched sports and drank beer in the venues we met in. Plus, as it turned out, the two women turned out to be lesbians which put a unique perspective to my life as I was regularly attending lesbian mixers and learning any thing I could about the culture which was so new to me. As we socialized together, I was learning as much as I could about being a woman. The first major lesson I learned was that I did not need validation from a man to be a woman which was a relief because of two reasons. The first being that I had very little interactions with men at all primarily I think because I was not attractive enough. The second of which was I really did not want to deal with all the drama I knew men can bring from all the time I spent as a man. I knew how to deal with ciswomen all my life and felt more comfortable with the drama women bring. I always had more women friends than close male friends.

The two most profound allies were yet to enter my life at that point.

As part of my online searches, I did have one response from a Wiccan/lesbian woman in nearby Cincinnati, Ohio. She told me I had sad eyes from my online picture, and we slowly began to correspond by text messages before I felt comfortable enough to talk to her in person. Finally, I got over my shyness and after talking to each other I decided to ask her out on a date. She accepted, and we decided to meet halfway between our homes with friends and go to a drag show at a well-known gay bar. We ended up having a great time and decided to set up another date. This time with my other friends at a women’s roller derby event. I was in gender heaven to be able to go with three other women to one place and enjoy myself for once. My help from allies was coming through for me.

At the same time, I needed to come out to what was left of my blood family. My parents and most of the rest of the family had passed away, leaving only my daughter (only child) and my only brother to come out too. I thought at the time I would have problems with my brother and hopefully not my daughter and I was right. My daughter’s only real reaction was why she was the last to know and my brother totally rejected me by not inviting me to the annual Thanksgiving Day dinner. He sold me out to his rightwing religious in-laws, and I have not spoken to him since which has been over a decade now. I was fortunate when my allies (daughter) and Liz stepped up to help me in my time of need. Not only was I invited to one Thanksgiving family dinner, but I was also invited to two. Even though I was happy to have someplace to go for the holidays, it was quite stressful for me to meet people at my daughter’s in-laws who had known me for years as a man but also meet Liz’s dad and brother for the first time.

The best part of having all of these strong allies on my side was they expected me to be myself. In fact, I was still on the fence of living as both binary genders as I met Liz. It was not too far into our long relationship that she told me the final words to kickstart my final plunge to a feminine life. One day Liz told me what I was waiting for, she had seen both sides of me and had only seen the female side, nothing of the old unwanted masculine me. That was it, I agreed and went about giving away what was left of my male wardrobe and never looked back as I started HRT or gender affirming hormones to further femininize my exterior self.

Along the way, I tried to explain to all my ciswomen allies how much they had done for me, but they would not take any credit. They never understood how much they did to help me become the happy transgender woman I am today. And, by the way, Liz and I finally got married after eight years and now have been together for over a decade.

 

 

Monday, March 16, 2026

It's Complicated

 

Image from Fa Barboza
on UnSplash.

About a month ago, when I was being admitted into a hospital with what turned out to be pneumonia, I had to go through a very complicated conversation about my gender with the emergency room nurse.

Complicating matters is the hospital I have been to before has my gender listed correctly as female, but the nurse had heard the emergency squad driver refer to me as “he” several times after he talked to me about my living situation. When I told him I was married to a woman, somehow, he automatically assumed I was a man. Which I did not care about at the time, as all I wanted to do was recover from whatever was wrong with me. Plus, chances are, I will never see him again (I hope.)

Anyhow, the admissions nurse waded right in with the complicated gender questions. She did ask how I would like to be referred to in the pronoun department which was nice after I needed to tell her I was born as and still was a biological male. Actually, none of the conversation bothered me as I told her I lived fulltime as a transgender woman and was even married to a woman. Where some of the confusion was coming in. She accepted all of that, and we moved on to more important matters such as my medical care. Since I had been admitted to that hospital in the past, I had all the confidence in the world we could move past the complicated part of my transgender self and get on to the real work.

Since I have now been out in the world as my authentic self for over a decade now, normally questions about me don’t bother me. Except in the case of a mammogram nurse, I had several years ago who enquired if I had any “surgeries down there.” Like it was any of her business. I was upset at the question and showed it because then she went ahead and did her job of completing the mammogram. I also consider myself to be an educational curiosity to many people who have never seen or dealt with a transgender person. They have been radicalized by the recent wave of anti-trans political ads and have no way of knowing we often lead similar lives to them and are not the flamboyant style drag queens again on the ads.

Seeing as how I chose a complicated life to live, I need to live it the best I can, and I must say, I have encountered very few haters of gender bigots in the world. Which surprises me. I judge my public gender success on the amount of “he’s” or “she’s” I get when I am out in public. Going back to the hospital, the overwhelming number of nurses and aides did not gender me at all. They did their job and just kept going. All except one day nurse I had for two of my five days who kept infuriating me by calling me “buddy.” As I was stuck with her, I saw no point in explaining how I was not her buddy, for several different reasons.

I have a lot of compassion for those people who don’t understand me if they are not evil about it or want to further take away my rights. Mainly because I try to remember how long it took for me to understand myself and even longer to do anything meaningful about it. If I don’t set my expectations of people too high, then I am pleasantly surprised when they reach my expectations of a good person who of course tries to understand complicated me.

I think too, that growing up with gender dysphoria automatically qualifies you to be more complicated than the average non-transgender person. I know for me, the daily conflict of trying to decide if I was a boy or a girl growing up was a pressure I would not wish on my worst enemy. Learning to live with it was a constant problem I needed to deal with for what turned out to be nearly fifty years before I came to my final decision on how I was going to live. What a relief it was to get the gender burden off of my shoulders and on with life. Knowing completely, I would be facing difficult, complicated life choices ahead on my path to my dream.

It turned out, my recent hospital visit was just a reminder of the life I was trying to lead. I spend too much time in my cocoon away from the public. When I do get out, I am fortunate to have my best ally Liz to lead the way. If anyone is on the fence concerning my gender, when she continues to call me she, it really helps to set the tone and pave the way for public acceptance, A prime example was the recent bus tour to Florida we took. All the interaction Liz had with the other travelers set me up for success.

If you are contemplating going down a similar path as I did, just be aware that it will be complicated but on the other hand (as Emma said to me in a recent comment, very interesting.) For whatever reason we choose this path to our dreams of living as a transfeminine person, when we keep in mind what the difficulty factor in doing it is, we are better off and well adjusted to the new world we are in. There are few human efforts as inherently difficult than crossing the male to female gender frontier. The gender euphoria is worth it though when the public reaffirms who you are and you can finally come full circle back to the person you were always meant to be. They will never understand how difficult and complicated your journey was.

When you make it interesting too, you really have been able to make your life a success. It is for you and only you to understand.

 

 

 

 

Saturday, March 7, 2026

Buckle Up for the Ride

Image from Inis Piazzi on
UnSplash.
I am biased I know but I think negotiating a full-fledged trip through the gender frontier from one side to the other side is one of the most difficult things a human can do.

Unless you are blessed with an overabundance of feminine qualities and characteristics, you very much start out from point zero with your femininization project and it shows. I am an example as I thought I looked good with my tight clothes and makeup which would have looked good on a clown in drag in the circus. In all fairness, it took me awhile to catch up because my gender workbook was blank and I had no one to help me fill it out. No overly concerned mom to tell me what not to do with makeup and no peer group of girls to coach me along. It was all me, and it showed. Except in the mirror which kept on lying to me by telling me I was a pretty girl.

It wasn’t until I began going out into the world did, I find out how wrong the mirror was. Numerous times, just after the mirror told me I looked great, I was bounced by an unforgiving public back to the safety of my closet. Through it all, some people were so cruel with their comments, they sent me home in tears. It was during those dark days when I really had to buckle up and decide what I was doing was right. Somehow, deep down inside, I knew I was right and I needed to figure out what exactly I was doing wrong when I cross -dressed and went out.

What happened was, I had the where with all to look around at all the ciswomen around me and notice what they were doing. By doing so, I noticed a few of the women were as big as I was, so size was not the issue which was dooming me to being laughed at. It was how I moved and how I interacted with the world which mattered. Plus, it helped that my makeup skills had begun to dramatically improve. I quit feeling sorry for myself and started to fill out my own gender workbook without being a victim. Because I was stuck with a testosterone poisoned body and somehow, I needed to work my way around it.

I started by going on a diet which I lost fifty pounds on and started to take better care of my skin after I shaved, so I used less makeup and found less was actually more. At the same time, I began to haunt the local thrift stores for just the right piece of clothing which I could buy which flattered my new slimmer figure. I still had my male torso with the broad shoulders, and I had to dress my way around them. I discovered new favorite outfits with loose flowing tops combined with denim skirts that worked really well for me.

Little did I know, all this progress I was making was placing me on a one-way track towards an on-coming train. And that train was how I was going to communicate with the world which suddenly accepted me? I was extremely shy and had a difficult time communicating with the world anyhow and now I had to add on a new totally foreign language to deal with, the language of ciswomen. Initially, I was too petrified to say anything but then slowly gained the confidence to shyly join in conversations. It was so new and difficult that I needed to really buckle up to do it. I found if I did not, I would destroy everything I sat out to do by appearing mean or worse yet, bitchy. The last thing I wanted.

Once I buckled down and put my fear of communication behind me, my world opened wide with new vistas of gender enjoyment. It turned out that what I said was more important than how I said it and with that knowledge, life became easier as a transgender woman in the world for the first time.

No matter where you are in your gender journey, look ahead and not behind you. Sure, you can learn from the past, but it should not dominate you and stop you from proceeding along your way. Keep in mind, you are on a very difficult journey with major life risks at hand such as spouses, family, friends and jobs. Also beware of the trap I fell into when my second wife accepted me as a cross dresser but then completely rejected me as a transgender woman. She was correct in thinking there were vast differences between the two. Just putting on a dress and makeup just did not solve any of my gender problems anymore. I increasingly wanted more of life in the feminine world and was buckling up to get it by wanting to be approved for gender affirming hormones or HRT. I was eventually approved for the dramatic changes the hormones made but sadly my wife passed away before she could experience any of the changes with me.

In my long life, it has been a rarity for me to experience firsthand any trans woman or trans man who has had a smooth, uneventful journey.  So, if you are just considering starting, or just beginning your gender path, it is best to prepare for a bumpy ride, so buckle up tight for the trip. Undoubtedly, it will provide you with setbacks and surprises you never expected. Like I always say, the gender trip is like a rollercoaster at a big amusement park, it is worth the price of admission if you let it be. As I said, just be sure to buckle up for the ride of your life. It is one most humans never get to take.

Think of it this way, make your buckle part of your fashion accessory and everyone can admire it.

 

 



Saturday, February 28, 2026

Innocent until Proven Guilty

 

JJ Hart


In many ways, this post is an extension of yesterday’s article. It involves the constant gender dance my second wife of twenty-five years and I had through in our marriage until she passed away.

Most of the problems occurred when I could not face the truth about myself. I was much more than a casual cross-dresser and just having the occasional chance to dress in front of the mirror in my feminine clothes was just not enough to satisfy my dreams of becoming a full-fledged transgender woman someday.  That was when I entered the most shameful time of my life when I like to say, I started to cheat on my wife with another woman who happened to be me.

As with most cheating episodes, mine became very complex. First, I started innocently enough with me taking short trips out of the house by walking around our neighborhood. When I got away with that, I started driving around as a trans woman to nearby cities where no one would know me. It was when I began to gather the courage to get out of my car and start exploring clothing stores, malls and book store to name a few. Before I knew it, I was hooked and I was having lunch on my own, just to see how successful I would be as a novice trans woman. Amazingly, I found the world was mostly nice to me and I kept experimenting. Which put me directly in the crosshairs of what I pledged to my wife. That I would never go out in public as a woman. She even went as far as letting me have the money to rent a motel room where I could dress and go out.

I even abused that privilege and still left the house on a regular basis. The problem that I had was removing all the traces of makeup that I was wearing when my wife was gone and I had to pass her strict inspection when she got home. Before long, regardless of how hard I tried to remove all my makeup, I was guilty until proven innocent. My wife knew I had been out, no matter how much I lied and tried to talk my way out of it.

Once I started seriously down my gender path to trans womanhood, I can confess I was never quite innocent. I would look for any opportunity to get out and about and improve my worth in the world as a woman. To be sure, I was not proud of what I was doing, but the whole process felt so natural that I just had to keep going and challenge myself to see what was around the next corner of my life. Even though the whole lifestyle change I was going through was so scary, it was also exciting and natural. As if something deep down inside of me knew I was on the right path.

As I always say, all of the lying and sneaking around took a tremendous toll on my mental health. All of my insecurities came to light when my normally honest life was torn apart by lying so much to my wife. I guess you could say too, for a while I was lying to the world about who I was too when I first started to go out in the world. I was guilty with strangers who did not know they were interacting with who I really was, not some sort of drag act. In fact, it took me several meetings with the same people to overcome that major obstacle in my life. The last thing I wanted back in those days was to be connected with any of the negative talk show press the cross-dresser transgender community was getting. Or even worse when we were being compared to someone who was up to no good by disguising themselves as a woman to commit a crime.  As a group back then, we were guilty until proven innocent.

I was fortunate in that I managed to purge my feminine self about six months before my wife died, so at least, I could do the right thing and honor my promise to her for a short time. For a number of reasons, it was the longest six months of my life.  It turned out when she passed, I would never have to consider purging again. Except when I made the major decision to finally give away all my male clothes for the last time. The best and most complete purge I ever made.

As I reached that point in my life, I vowed that honesty would always be the best policy and I would always be innocent until proven guilty. It turned out my inner hidden female had always thought the same thing and when she had the chance to see the light of day, she made a honest attempt to do the best she could to take the ball and run with it. When that corner had been turned, it was like I had been freed from a giant weight on my shoulders. I could breathe again and be fully proud of who I had become, a whole transfeminine person.

I can’t say it enough, the days and years of lying and deception on my part was totally my doing because I did not have the courage to face who I really was. I have no excuse for my cowardice except for my male self just did not want to give up what he worked so hard to obtain.

Certainly, I would not wish any of the gender turmoil I went through on my worst enemy and if the politicians who keep passing the anti-transgender bills across the country had to walk a mile in our shoes, they may have a whole different understanding of what we transgender women and trans men face on a daily basis. Then we would be judged to be innocent until proven guilty, which we rarely are.

 

 

Saturday, February 21, 2026

A Little Success Goes a long Way

 

Hair by JJ Hart. Bead Work
by Liz T Designs

In the life of a novice transgender woman or man, a little success can go a long way. Mainly because very few of us are blessed with the natural gender characteristics of the gender we feel is truly us to get us started.

At that point, we must feel our way along. Sometimes submitting ourselves to abuse from the public as we go forth in the world for the first time. In my case, I make no secret of the many times I headed back home in tears after being laughed at to my face in public. Somehow, through it all, I was able to catch and enjoy brief moments of gender euphoria to keep me going to a distant dream of possibly living a life as a full-time transgender woman. Of course, I did not have any idea that I actually could do it.

I was fortunate that practice made perfect (or close to it) as I was able to improve my makeup and clothing skills to where I could survive in public when I left my mirror. Which I discovered was one of my biggest problems because it had the tendency to lie to me when it came to my overall appearance as a woman. Too many times, I went out thinking I looked great and then had the world slap me down in laughter because of the mirror. Plus, my male ego was giving me the wrong impression of how to look as I attempted the sexy look when I was in my thirties not in my teens. There could be no shortcuts in being able to present myself well as a trans woman, I would have to concentrate harder on my makeup and wardrobe than anything I ever tried before. Just because I was trying to dress sexy and show too much skin would not work in the real world if I was to blend in with the other ciswomen around me.

Finally, success did come to me as I haunted the thrift stores in my area for just the right fashion to attempt to flatter my testosterone poisoned body. It turned out I could not attempt to test my success until I left the gay venues I was going to and tried to go straight with my public excursions. The gays did not care how I looked and just viewed me as a drag queen any how so I was wasting my time until I discovered how I could make it or not in the big sports bars I was used to going to as a man. When I followed my three-step method of acceptance, I had no problems being accepted. My three steps were to put my fear behind me and smile, never cause any trouble and tip well earned me the right that every regular had. Especially the one I cherished more than anything else, the right to use the women’s restroom.

With my success came responsibility. I needed to be on the alert for other strangers who wanted to talk to me. Especially ciswomen who were curious about why I wanted in their world. Success in my communication skills led me to learn more about living behind the scenes as a ciswoman than I ever though I could. My primary example I always use is how women use the power of nonverbal and passive aggressive communication to get by in the world. Especially when it comes with dealing with men. It was very difficult for me to learn the basics women use to live but as I did, a whole exciting new world opened to me. Perhaps the best part of it all was that it felt so natural, so I knew I was on the right gender path in my life for the first time.

My success then began to go a long way when I discovered a small circle of women friends I could socialize with on a regular basis. I was always a social person anyway, so the fit seemed fun and natural to me as I gained the confidence I never had before when I was a solitary, lonely cross-dresser. And the best part was, I was having the opportunity to learn from the other women around me about knowing how it really was to interact with the world as a transgender woman rather than how I always dreamed it would be. Needless to say, I learned a lot.

I looked at my whole experience as paying dues as I went from being laughed at in public all the way to having my own set of ciswomen friends to socialize with and even marrying one later in life. Ironically, it was my wife Liz who convinced me once and for all to put my male self behind me, give away all my male clothes and start gender affirming hormones. Which I had always considered the next logical step in my male to female gender transition. It turned out, hormones would be the great “aha” moment in my life as the femininization process took hold. It was as if I should have always been on the hormones because the process felt so natural. The changes went way past the external softening of the skin, breast and hair changes all the way to all the internal changes such as emotions and more.

For me, success took a long time coming, and early failures at passing in public made me very timid. Once I made it through all of that, success came more naturally to me. All the way from just leaving the house cross dressed to HRT, my life became a blur of changes. Sure, the battles I needed to fight came at me fast and furious because I was so embedded in the male culture but I was able to fight my way through them and be successful as I discovered a little success went a long way and kept me going along my gender path towards a life I had only dreamed of.

Friday, February 6, 2026

Invisibility as a Trans Girl

 

Image from Lindsey Feanzke
on UnSplash, 

Another major realization I had during my wife Liz and I’s vacation journey was how invisible I had become as a transgender woman.

It was not an easy realization to come by since I have been out in the public eye full time for over a decade now. During that time, I went through all the stages of going from sheer panic all the way to suffering from impostor syndrome when I found myself in a feminine world for the first time. Along the way, I had heard the term stealth applied to the impossibly feminine transgender women I had seen who had passed the public perception of beauty easily. A standard I never thought I could reach with the testosterone poisoned body I had to work with.

In many ways, I found I never could but then I began to look around me at all the other ciswomen in the world who did not achieve a high standard of classic beauty either. And they found a way to lead successful fulfilling lives as women. When I realized they had a path, I knew I had one too. I could be secure in my own womanhood even though my path was different than most of the world. The only real problem I had was dealing with the late start I had dealing with my realization that I was a transfeminine person all along. I was blessed with having the advice or criticism from moms or peer groups to help me out of my gender shell. I only had a mirror which was highly capable of lying to me on my feminine presentation. Even though I looked like a clown in drag because of my poor makeup skills, my mirror friend kept telling me I was pretty.

It was not until It began to have the courage to use the world as my mirror did life begin to change for me. I needed to pay closer attention to what the ciswomen around me were wearing so I could blend in with them and not create unwanted attention to myself as a transgender woman. In other words, I did not know it yet, but I had my first lessons in being invisible in the world as the person I had always dreamed of becoming.

Little dd I know, the more I was out in the world, the more lessons I would have to learn to just survive carving out a new niche in my life. It was one thing to talk to myself in the mirror and a whole other to communicate one on one with another woman n the world. Early on, before I gathered much courage in what I was doing, I would lay back and let the other person (normally a woman) take the lead in any communication efforts she wanted to do. I found it was the best way to go as I learned what the gender I so desperately needed to be a part of operated behind the gender curtain which men could only guess at. I became comfortable in women only spaces such as restrooms and parties where men were not invited. In doing so, I was making myself more invisible as a trans woman and more visible as a well-rounded person.

All of this brings me back to what “stealth” as a transgender person means to me. For the longest time, as I said, I thought the word applied to only the upper echelon of transsexual beauties I saw online back before anyone could use filters to make themselves look better. Back in those days, feminine facial surgery was the way to go to re-arrange what you were born with in the appearance department. Seeing how I could not afford any surgery and was still working as a man, I was stuck with trying my best to improve my looks through the miracle of makeup.

By this time in my life, I was approaching my sixties and had managed to carve out a nice little life with affirming women friends, I decided to take to heart again what my trans friend Racquel had told me years ago. She profoundly said I passed out of sheer will power and I took it as it was intended. That I would never be the most attractive woman in the room but I could survive anyhow as I found my path as a transgender woman beyond the point of ever living a male life at all and I was now invisible to the world as my former self. After all the decades of attempting to live as a mix of the two main genders, I had made it to the point of just being me. More importantly, I was able to show the public around me who I was too. Now, it could be when one ciswoman on the trip came up to me to tell me how much she respected me coming along on the tour, it could have been she was referring to me making my way with my walker on wheels, or the she sensed I was transgender. One way or another, I respected what she said.

It turned out she was not alone. To my surprise, I had several other couples tell me the same thing and they were the ones I least expected to do it. Which teaches me once again not to prejudge people ahead of time. Shame on me, because I hate it when people prejudge me.

I guess becoming invisible for me came the same time I learned to just be me and I my life’s journey just happened to include being transgender. Now I need to keep trying to adjust to my new realizations. Since it took long enough for me to do it.

 

 

Friday, January 2, 2026

Practice, Practice, Practice

 

Image from Mor Shani
on UnSplash. 

Sometimes I wonder if some people don’t take the time to understand how much practice I needed to do as I became my authentic self. I guess I could say I went through nearly a half century of work to become who I dreamed of being. It was far from easy.

Starting at the beginning, I never had much to work with as far as being an effeminate boy. Not to mention, I was born into a very male dominated family. Very early I learned I was going to have to work hard to not look like a clown in drag when I tried my best to look like a pretty girl in front of the family mirror. I always equated putting on makeup with painting the plastic model cars I had. Which I was always very bad at doing.  

It did not help when I earned my own meager amount of money working around the house or delivering newspapers in the neighborhood. Then I used the money to try to shop for makeup. I still remember to this day, the first time I was confronted by the sheer number of various makeup brands and variations to try. I finally selected several products out of desperation and hoped for the best as I was trying not to use my mom’s makeup anymore. Now, I don’t remember how successful I was, but I kept on trying to practice on my face until I got it right. Or so I thought. It wasn’t until years later that I visited a true professional makeup artist that I discovered I was not working on the true potential of my makeup to its maximum effectiveness. I was merely making the same basic mistakes over and over again.

I was fortunate to have the makeup artist who was able to explain to me in terms of understanding what he was doing, so I could repeat the process later. Practice for once made perfect. I was able to paint my model cars in a way that my friends admired them. But this time, I was actively admired at the crossdresser-transgender social mixer I was at, and this time when I tried to hang out with the “A” listers (as I called the beautiful, more advanced crowd of attendees) I was accepted. The best part of the whole evening was I then had a basis of where I needed to be as far as being an accomplished cross dresser but on the other hand, I was presented with a deeper set of questions about what I was going to do about my male life as I knew it.

What I decided I had to do was take my transfeminine show on the road so to speak and see if it would play at all in the public’s eye. Away from all the safety of mixers and gay or lesbian mixers. That is when the real practice set in. I needed to stop all of the hard-earned male muscle memory I had learned and start to learn the best that I could the graceful, fluid moves of a cisgender woman. Naturally, the whole process was difficult to do. Especially when I was switching back and forth between the two main binary genders almost daily. Constantly, I needed to remind myself of who and where I was so I would not end up at the wrong place at the wrong time.

Through it all, when I thought I was being successful in going down my transgender path, roadblocks always emerged which sent me back to my drawing board and started setting up more practice. Those were the days of taking every spare moment I had to sneak out of the house and begin to carve out a new life for myself as a trans woman. Once I made it successfully out of the gay venues I was going to and into a few of the big sports bars I was used to going to as a guy, I started to relax and enjoy my new exciting life even more.

No matter how much I try to gloss over this part of my life, the fact still remained I was essentially cheating on my wife when I went out as myself. Deception was never my strong suit, and I was never proud when I needed to lie about what I was doing. By this time, I had reached the point of no return but still was afraid to face it. I hid it by staying in the so-called practice mode I was in. If I could have just one more experience being a transfeminine person, it would make it so much easier when I decided to permanently put my old unwanted male self behind me for good.

Finally, I quit kidding myself, and I was doing so much than practicing over and over again to live a transgender life. I had always dreamed of doing it, so it was time to do something about it and live it. Who knows, maybe all that practice at living a feminine life saved me in the end as I finally learned to move and communicate my way around in a ciswoman’s world.

 

Monday, November 24, 2025

Transgender Dreams

 

Image from Felipe Delgado
on UnSplash

Obviously, we transgender women and transgender men do a lot of dreaming when it comes to the ultimate results of our lives. For example, when I was very young, I could never speak truthfully when an adult asked me what I wanted to be when I grew up. Saying I wanted to be a woman would have never been acceptable and would have rewarded me with a visit to a psychiatrist. So, I said something more acceptable such as a lawyer or a veterinarian.

I had to save my ultimate desires to be feminine for my dream world and often went to sleep thinking of how it would be if I could wake up as a pretty girl. Of course, I was never able to take advantage of such a thing happening to me and I needed to make the best of what I had to work with. Which was about ready to radically change for the worse when I went through male puberty. As I started my growth spurt, I rapidly outgrew all my mom’s clothes I had tried to squeeze into and had to rely on my meager allowance added to my newspaper route delivery money to try to sneak out to stores and buy my own clothes and makeup.

Through this portion of my life, my mirror was my friend and helped me to bring dreams of being a pretty girl to life, no matter how I really looked. It wasn’t until I began to experience the public’s reaction to me did, I finally get a fair and accurate reaction to how I really looked. I desperately dreamed of being more than a clown in drag. After tons of work and trial and error experiences, I finally made it to where the public at least knew I was being serious about achieving my dream of being a woman. Little did I know, the real work I would need to do to achieve my dream was about to begin.

The more I explored the world as a novice transgender woman, the more I found I had to do to survive in the new exciting feminine world I had dreamed of being a part of. When I was in the public’s eye, I found I attracted the attention of ciswomen as never before and as I did, I needed to get radical and do things such as talk to them. Initially, I was very shy and completely unprepared to take such a big step, but I was way past the point of ever turning back. For the first time in my life, my dream appeared to be within reach, if I kept learning what my new world meant.

I found I was stuck in some sort of a gender never-never land. Ciswomen instinctively knew I was not Cis but on the other hand, wanted to be in their world. Fortunately, I found most of them let me into their worlds and showed me a path to being successful, if they knew it or not. I did not care how I received the help and guidance; I was just trying to achieve my dream of living as a successful transgender woman. As I tried to point out in yesterday’s post, I went past the point of trying to be trans all the way to just being me. Which I think the women around me accepted because of my honesty. By now, you may be thinking what about the men around me? For the most part, they left me alone. Which was fine by me. I wanted out of their club and wanted nothing to do with going back if I had anything to do with it. I was successful and never did. My dream increasingly appeared to be reachable, and destiny opened her doors for more success for me. Primarily when it came for time to consider going down the path of gender affirming hormones or HRT.

I knew first, I needed to find a doctor to approve taking the hormones and I found one in one of the Dayton, Ohio LGBTQ publications. He had openings and I was able to get in for a checkup and then receive my precious prescriptions for initial minimum dosages for estradiol and spiro to get started on a new path towards achieving my dream as never before. After I began the minimum dosages, I had no adverse reactions and in fact the opposite was true. I felt as if I should have been on the meds for my entire life. They made me feel so good.

By this time, I felt as if I was living proof that transgender dreams come true if you pay your dues such as I did. The dues I paid were certainly the best investment I ever made.   

 

Thursday, November 13, 2025

Staying in the Present

 

ss
Image from Ekka Wessman
on UnSplash. 


As I progressed in my cross-dressing life to a novice transgender woman, it proved to be difficult for me in several different areas.

Just one of those areas was the amount of time I needed to stay in the present for the first time in my life. My problem was compounded by the fact I had trained myself to daydream my life away as I wanted nothing more than to be a girl. Then, when I took my feminine image out of the mirror and put it into motion, I needed to constantly stay in the present to remind myself where I was and what I was doing. If I did not, I would be in danger of slipping back to my old ingrained male self. The problem was particularly intense when I was trying my best to mimic the magical way ciswomen moved.

Sadly, I found if I relaxed at all, no matter how attractive I thought I looked as a trans woman, all would be lost if I looked like a linebacker in drag as I walked. And to make matters worse, I needed to quickly learn to change the old stay away masculine scowl I had perfected and replace it with a more welcoming feminine look. As I shopped and interacted with ciswomen in public, they wanted to smile at me, so I needed to be pleasant and smile back. Especially if they suspected all was not as it seemed gender wise with me. I did not want to appear as any sort of a threat.

Staying in the present brought about other pleasant rewards also, such as when I communicated with other women, I needed to look them in the eye and listen to what they were saying, not jumping ahead and anticipating what I thought they were going to say. My communication game with women had really changed.

After a lifetime of hiding in the future, the present started to be a very pleasant place for me to be. I could take the time to feel the different clothes and talk to different people from a whole new viewpoint. I could take and give compliments from others regardless of their hidden motives. I found just the most innocent mention of my earrings from another woman was not about my choice of jewelry at all, she was gently starting a conversation to find out more about me. It all carried into the learning curve I experienced when I began to take lessons in passive aggressive aggression, from other women. I never had needed much knowledge of passive anything with the alpha macho men I hung out with. They were upfront with me for the most part. Ciswomen, on the other hand, could smile at you while they clawed your back for whatever reason they had. For a while, I thought I was going to have to carry band aids in my purse for any surprise attacks such as one night when a woman was coming back from the restroom and caught me talking to her man and took a dim view of the situation.

The more time I spent in the present, the better my life had become, and I got to the point where I missed out on all the time, I spent daydreaming of my life away. As I wondered how it would be if I could shed all my male existence and redo it as a transfeminine person which made me unapproachable to family and friends as well as making me totally miserable. Also, all the jealousy I felt towards ciswomen would have been swept away if I had had the chance to live and compete with them in their own world. To be sure, it was a different world but a life I discovered I enjoyed immensely as I found my new life to be all I thought it would be and more.

To arrive at the point I wanted to be, I first had to be confident in how I arrived at my own womanhood and if someone did not like me, it was their problem not mine. Then and only then could I fully live in the present and most importantly, try to forget most of my past. The future is still a problem for me as I wonder what will become of me if I have to encounter an assisted living situation where my gender issues are not addressed. The difference now is that I don’t spend the time dwelling on it as I used to. The present is just more important for me, which was a hard lesson to learn.

 

 

I Got Scammed

  Image from Markus Winkler on UnSplash. Years ago, I discovered I was scammed when I attempted to climb my gender path towards my dream goa...