Friday, December 19, 2025

More Gender Dreams

 

Image from Robin Edqvist
on UnSplash.

Last night I had one of those dreams I always had hoped I would have when I was young. I dreamed I was dressing myself into a pretty woman and actually going out into the world. The experience was different because of some reason I still dream that I am male in the vast majority of dreams that I have.

Even better, the usual suspects in my world at the time were all present and encountered for in my dream. To the point I was even sneaking around my second wife’s back to cross dress. Another interesting point was my hair. As many of you know, through the power of genetics and HRT, I have been able to grow an amazing head of thick long hair at the age of seventy-six. Going without wigs and having my own hair styled was always an impossible dream for me, until it magically happened. Which is an experience for another blog post.

In the dream, I remember trying to choose between wearing a wig and brushing out my own hair, which I chose. For some reason, I was trying to throw caution to the wind and go out for something to eat with just women’s clothes, my hair and no makeup. Also, I was calling my wife at work to make sure she was still there, which was something I always did back then to not get caught. My second wife was the one I lost to a heart attack at the age of fifty and when and if I dream of her, she always is a blur. So, I was surprised when she appeared in this dream. My guess is it is because my habit of sneaking around her back and cross dressing was so prevalent in my life at that time that it stuck in my subconscious. And it just decided to make an unscheduled surprise appearance.

In the past, I have corresponded with other transgender women on how many of their dreams were with which gender. Interestingly, many of them responded that they dream mostly as women. I do too, sometimes, but mainly I am stuck with being a man in my dreamworld. Perhaps it is because I needed to battle so hard to maintain and even advance in a male world, I wanted no part of. I just needed to survive. That portion of my life still equals roughly two thirds of my time on this planet. So, the more time I spend as a transfeminine person should equal out to the more dream time I have as a woman.

Exactly like when I was young and could not wait to go to sleep and dream of waking up as a pretty girl, this morning I did not want to wake up and rejoin reality. It made no sense to me why I felt that way because I have been so fortunate to have been living a transgender dream in a real world for over a decade now. I guess change comes slow in my subconscious, and I should take advantage of still living part time on the other side of the gender border (male).

I suppose I should be lucky I don’t have gender dreams which turn into nightmares. I do hope I have the chance to meet my second wife in another world after I die and finally learn that she accepts me and not just in a dream. Afterall, she was right when she told me to man up and be a woman. I finally did and became happy.

 

 

 

Thursday, December 18, 2025

Letting Things Happen versus Making things Happen as a Trans Woman

Image from Mahdi Chaghari
on UnSplash.

Perhaps you have heard a football coach talk about slowing the game down and simplifying it for his players. Of course, I had to equate it with being a transgender woman or trans man when I heard it.

I began to think of all the stressful days I spent in front of the mirror as my perception of a pretty girl, then taking my image public and into the world. For years it never occurred to me that I was trying too hard. I was attempting to micro-manage myself to ensure every little aspect of my feminine image was correct. Here is an example of what I was doing wrong. On any given day, my makeup and fashion were on point, and I was confident about my presentation. Then as I was out trying it all in the public’s eye, I would either catch myself walking hunched over like a linebacker or worse yet, trip over my own heels and almost fall. It took me quite a while to realize what I was doing wrong and try to change it.

For me, relaxation and confidence were the key to real gender change. I was letting it happen rather than making it happen. I discovered it was so much more pleasurable for me when it happened that way. After that I could take my game to a different level such as communicating one on one with the world for once as my authentic feminine self. A key point I had to do if I was ever going to make it to my dream of a male to female femininization project.

I also established bucket lists of things I wanted to do as a transgender woman and was able to accomplish most of them except a couple of ill-thought-out visits to women’s rooms when I had the police called on me. Letting it happen surely did not work for me then, but I recovered and gained my restroom privileges in other venues I went to. Fortunately, the police had better things to do than mess with me and I went on my way without further problems. That was years ago and I haven't had any problems since. That was a good thing because the restroom privilege was something that I needed more than wanted.

I cannot stress enough about how much I had to learn during this period of my life when I was making a serious push towards transitioning from a serious cross dresser all the way to a transgender woman. When in reality, it was mostly a mental transition, it was still a very important one to make. I have a difficult time explaining it but all of a sudden, something clicked in my mind, and I knew another change was needed. I was so more than a man wanting to look like a woman.  I wanted to be a woman and feel like one as close as I could. That was when I successfully set out to socialize with cisgender women just to see if I could. I conquered my fear and found out I could add another layer of just letting it happen versus making it happen.

By this time, my muscle memory had improved so much as a trans woman that it became natural to me. So much so in fact that I had to be careful I was not too effeminate when it came to me working my male job and living with my wife. It finally became too much for me to juggle, and I needed to put it down before it was too late and I became more self-destructive than I already was. What I did was, attempt to do more things as a transfeminine person and do as less as humanly possible as my male self. It is one of the reasons I took so long to transition, because of the need to work around a disapproving wife and male self which was desperately hanging on.

You regulars know this part of my story when my wife tragically passed away. Which left only my weakened male self to resist any efforts at total domination from my inner female who had waited so long for her chance to live and write her own gender workbook. Little did I know she kept her own workbook up to date and was ready to go. If and when she had a chance to use it. Perhaps, your inner female is keeping a gender workbook also and you will not have as far to go to catch up when you get the chance to live your life.

I discovered too that letting it happen versus making it happen was mostly common sense. Even though the two main binary genders do things differently, they often operate in parallel universes which are the same and seem to be doing more so in the younger generations. I first learned up close and personal during my first girl’s nights out I went to. I was worried about what I needed to do to be able to interact with the group but then found they had just flipped the script from jobs and sports to family and friends with the women. Quickly I relaxed and started to let my inner girl flow, and I was fine with most of all the other participants except for one who I perceived as being a miserable person anyway. Who was unlikeable to me, and I left her alone.

I chuckle to myself when I think of how my football coach’s words would come back to help me in such a different way later in life. I guess it proves that you just cannot count on anything staying the same when it comes to gender. Perhaps that is a clue why the population at large knows nothing about us and we live parallel lives from both of them. Whatever it is, if you are in your path of gender discovery, you will certainly feel the change from making it happen to letting it happen.

 

                                                                                                                                          . 


Wednesday, December 17, 2025

Gender is a Basic Human Instinct

 

JJ Hart, Birthday Dinner.

One of the most basics of human instincts is gender. It comes with us at birth and is then (right or wrong) reinforced by our families. External factors kick in to put us in a tight gender box and keep us there. How we are treated as boys and girls, goes a long way in how our future is shaped. In my mind boys were always told to get out there and conquer the world while girls were coddled in a pretty world. It took me decades of interactions with ciswomen to learn that was not true. In their own ways, women face the same competitive challenges as men, just coming from different angles or perspectives. I told one of the experiences I had yesterday when I waded into the ciswomen’s world for the first time and discovered how brutal passive aggressive behavior could be.  

Examples include boys competing more physically with each other while girls learn to compete just as hard but in a more passive nature. One way or another, gender as an instinct is ingrained into us quite early in life and is difficult to change. One of the reasons transgender women and trans men are so misunderstood in the world today. Not to mention the fact that we are very rare, and very few people have ever met a transgender person. I know my parents from the “greatest generation” were not great enough with me to understand how their first-born son wanted to be their daughter. Taking a page from the great Christmas movie “A Christmas Story”, I never wanted the BB Gun that “Ralphie” wanted in the movie, but I got one anyhow. Instead of the baby doll I really wanted. All my gender instincts were kicking in although I was not sure I knew exactly what was going on, I knew something was definitely wrong.

It was not until I began exploring the public as a novice cross dresser or transgender woman, did I start to understand what was going on with my own gender instincts. Facing up to the fact I never belonged in the male world as an active participant at all never came easy for me. Mainly because I had worked so hard to survive in a gender I did not want to be. To make matters worse, I was becoming more of a success in the male world. Even though I was so self-destructive I kept tearing down all the successes I kept building up as soon as I achieved them.

In my case, I think the war I waged with my internal gender instincts was much worse than the battles I faced for acceptance as a transfeminine person in the public’s eye. Even though they were major hurdles, obstacles such as confidence and impostor syndrome were holding me back. It seemed no matter how successful I was in my new world, I still felt like an impostor or outsider looking in. It took me quite a while to overcome my doubts and feel like I had as much right as the next woman to be in the space I was in. Over and over, I felt I was growing up into the woman I was always destined to be. It was just taking me longer to do it because of many external factors such as a whole train load of male baggage I had managed to accumulate in my life.

Along the way too, I was becoming a keen observer of the public’s gender instincts. Primarily ciswomen who for some reason had no problem with me as men nearly completely left me alone. By doing so, I was able to read other women like I had never been able to do before. Slowly but surely, my life began to turn full circle. Instead of going out to be alone, I was going out to socialize with other women who were mainly lesbians. They taught me a whole different set of gender instincts, mainly revolving on where I stood with the other half of the population, men. While other transgender women I knew were struggling to be validated by a man, I was flourishing when I was validated by women. It obviously is not a world which worked for everyone, but it worked for me.

With all the help I was receiving, I made it to a point where I did not consider myself trans when I was out in the world. I was just me, and I had all the confidence to go with it. It took me over a half a century to completely figure out my gender instincts, but I did it with some powerful help such as HRT or gender affirming hormones. The meds I was approved for helped me to understand what ciswomen go through in their lives such as hot flashes and other effects of female puberty. When I tried to talk about it to my women friends all they did was laugh and say welcome to their world. What I could not say was how happy I was to be there.

Cracking the code of human gender instincts is very difficult to do because it is so deeply ingrained in all of us and in many ways, it is a selfish thing to do. It takes a special person to understand when you have to immerse yourself in the other binary gender to just survive in life. If you are blessed to have found such a person, be sure to cherish and hang on to them because they are so rare.

In the meantime, keep your head on a swivel and be on the outlook for ways to improve your gender instincts. It is a difficult process and never one to be taken lightly. For me, at least it was a lifetime journey to finally discover something I already knew I refused to accept. I had my gender identity totally backwards and ended up paying the price for years. Just because I was afraid to face myself.

 

 

Tuesday, December 16, 2025

Staying in your Own Gender Lane

Image from Earnest Tarasov
on UnSplash.
Staying in my own gender lane may have been more difficult than I had ever imagined. Of course, it all started when I was externally born male. Then when I started to understand something was dreadfully wrong with my male existence, I needed to figure it out.

My first indication of what the problem might really be came when I discovered the thrills of wearing my mom’s clothes, since I did not have any sisters to beg for clothing off of. Sadly, even though I was thrilled to see my version of a pretty girl in the mirror, deep down I knew it was just not enough for me to stay in my cross-dressing lane.  I wanted to pull out and find myself in a more comfortable gender lane where I more than ever before to being feminine.

Before I could do that, I needed to define what being feminine meant to me. I knew just acting effeminate would get me nowhere except bullied to the point of beaten up and on the home front (which was very male dominated) I would probably earn a trip to a psychiatrist if my small stash of girl’s clothes and makeup was ever discovered. I was trapped in a male world I wanted nothing to do with, and worse yet, I was pressured to perform well in that world. I needed to be in a passing lane around as many other males as I could.

The problem was, I wanted nothing to do with that world and could not show it. And in the pre-internet era I was growing up in, I felt so all alone with no one to talk to about what I was feeling. I just knew I did not feel the so-called mental illness that gender issues were being referred to back then. All I knew was, I was having a very difficult time staying in the gender lane which was assigned to me when it felt so natural. Plus, when I woke up in tears after having such a realistic dream that I was a girl impacted my life terribly until I could get centered again where I was “supposed” to be.

Somehow, I made it through those very confusing gender days and finally made it out into the world to discover if I had any future at all in a world ruled by cisgender women. When here I was, a novice in their world trying to survive. I equated it with driving on the Autobahn in Germany. I quickly discovered when you were driving a VW Beetle (like mine) and ventured into the outside lane then you saw a car in your rearview mirror flashing its lights, you better get out of the way. My life in those days often felt that way. I was learning lessons about where I wanted my transfeminine womanhood to go but I always seemed to see lights warning me in my rearview mirror.

Through tons of trial and error, I learned I could change my gender lane to the one I dreamed of. From as young as I could remember all I really wanted to do with my life was live it as close as I could to being a woman. Of course, that meant putting all my safe male privileges behind me and set out to build new ones in my gender lane with new life experiences. Like the Autobahn I found there were no speed limits on what I could learn or experience in the new gender lane I was in. More importantly, I had no one except my old male self to tell me to slow down before it was too late and I wrecked. Here is where I make the excuse of why it took me so long to transition because I was overly cautious that I did not wreck.

As I was in the gender lane I wanted to be in for a change, it w as nice to finally wake up in the morning knowing I was coming closer to my dream of living life on my terms as a woman and not having to keep falling back on my male self for last minute support. I was one and she was me for good.

But just when I thought I had it all in my new gender lane, I discovered many small nuances the ciswomen around me use that I needed to learn and put into practice. Such as the powerful use of nonverbal communication and passive aggressive behavior. For the first time in my life, I needed to look intently at other women when I talk to them and search their eyes for what they were really telling me. Which extended into the passive aggressive areas of behavior I encountered. There were many times I fell for a smiling face or non-threatening comment which turned out to be a knife in the back when I let my guard down. They were all lessons I learned the hard way as I earned my ability to stay in my gender lane permanently.

The best part was that the more I learned, the more I wanted to learn about the lane I was in. Even my biggest naysayer, my male self, had to finally give up and get out of my way. I was in my lane for good and there was nothing he could do about it. I had served my feminine apprenticeship I was walking the path I always was destined to walk and in the short and long term I got out of the way until I could salvage was left of myself and move forward. 


Monday, December 15, 2025

More Downs than Ups on the Gender Roller Coaster

 

Image from Pietra K. 
from UnSplash.

The gender rollercoaster of life was very real to me.

That is the reason I attempt to mention all of the ups and downs I have experienced over the years as I battled gender dysphoria. For me, the trip up the coaster was not often worth the trip down as my depression set in. Until I received the proper care for my depression, I would often not want to even get out of bed for days at a time. Of course, I could not do that, and life would have to go on. That life included an increasing interest in cross-dressing. When I was on an upswing, life was better and I thought I was even making strides towards possibly living my future dream of living in and competing with a world of cisgender women. All of which had a very large headstart on me towards possibly achieving their womanhood before I could.

All this turmoil sent me down the rollercoaster of life and right back to where I started from…deeply frustrated. It was not until I began to leave my closet or shell and explore the world, did I begin to experience any relief. In the world, I discovered that not everyone noticed me and it was true what my second wife told me that it was not all about me. I was relieved when I learned that most of the world was just living life on their own terms and outside of few haters, I could live my life too. It was when I discovered that I was able to ride the level part of my dysphoric roller coaster, for a while.  

It never failed that when I started to come off the flat spot of my coaster, I needed to fight my depression again. Nothing I was doing was good enough as a man or a woman. I was so involved in wanting a transfeminine future, I could not maintain a good solid relationship with my long term (25 years) wife. The only things I was doing was keeping my head above water at work as I carved out the beginnings of a new transgender life. While I did all of this, I managed to make myself miserable as well as those around me. If I could not live with myself, how could anyone else, was my main thought pattern as I rode the roller coaster of life. All I knew was, I needed to hang on tightly for the ride ahead.

Of course, you all know I did manage to hang on, or I would not be here writing this today. Many times, it was because deep down inside I had this unmistakable idea of what I was doing was right. I had waited a long time in line to ride this gender rollercoaster, and I was not ever going to give up my spot. Once I came to this conclusion, I was able to stand in line with other ciswomen and not be so intimidated. And they were less intimidated by me and the rollercoaster hit another exhilarating turn as it headed into a tunnel. This time though, coming out of the dark did not mean I was heading into so much depression. Still, I knew I had a lot of work to do before I could reach my goal or dreams of living a fulltime transgender life.

Every time I thought I had finished a ride on the roller coaster, I found I needed to turn right around and get right on. A ciswoman’s life was so much more complicated than I had ever planned for, there were more challenges ahead. I still had key decisions to make concerning how I was going to live my new life. Such as how I was going to support myself and what was I going to do about telling my remaining family and friends that all along I had been living a lie. Last but not least, I would take the major step of seeking out approval to begin HRT or gender affirming hormones.

Amazingly, each time I jumped on the roller coaster, my rides became shorter and less eventful. I had taken the time and effort to set myself up as a regular in certain venues I went to all the time, so I did not have to go out just to be alone. I was always a social animal as a man and now I was too in my new exciting feminine world. Most importantly, I was able to develop a small circle of ciswomen friends who unknowingly boarded the coaster with me. They showed me the final steps I would have to take to get off my lifetime ride permanently. Maybe the best part was they never knew what they did for me. Eventually, what came out of it all was my marriage to my third wife Liz. A lesbian ciswoman who was instrumental in kicking me off my roller coaster permanently.

Even though I was ultimately successful in reaching my transgender dreams, I am not so sure I would recommend how I did it to anyone. I took too many chances and consumed too much alcohol along the way. Often, I used alcohol to give me a false sense of security when I was riding a scary coaster. Those were the days when I had to internalize my emotions and fear and “be a man.”

Finally, and thankfully, the world around me changed and I stepped down off my roller coasters all the way to less intimidating merry go rounds. Even they didn’t last as I decided to leave the gender amusement park altogether. Truthfully, I never got much of anything which was amusing anyway, and on some occasions, bigots and haters even put me into the freak category. Sadly, I never won any prizes for the most rides on a roller coaster or had a chance to reach for the ring on the merry go round. I was at least a survivor. I did not have to be a man at all.

Sunday, December 14, 2025

Wintertime in Ohio

 

Hair by JJ Hart, Beadwork by
LizTDesigns.

My wife Liz sells a fairly wide range of her artistic/crafting skills on a platform called Etsy.

Yesterday, she ran into a shipping snag with an item that she sold, and we had to venture out into a very busy scene as everyone was out before a winter storm hit. We did not have far to go to get to the shipping store and then the post office, so I did not have to do any prep work for the brief trip. In fact, I did not even have to shave closely since we had gone out to eat the night before with her son at our favorite restaurant.

The bottom line was when I finished writing yesterday’s post, and Liz abruptly said was I ready to go, I was. I was in a what you see is what you get mode. I was not a transgender woman, I was me, and I am always interested to see how that attitude plays out. Because no matter how long I have been out in a transfeminine world, I still have a little voice in the back of my head wondering will I be discovered as some sort of a gender impostor.

As it turned out, the only person I encountered closely with Liz paid no attention whatsoever. I was just another face in the crowd while she worked her way through the problem Liz had and then we were off to the post office. As I said earlier, everything was crazy busy which meant the post office was going to be also. This time I took the easy way out and stayed in the car. I was in jeans, an Ohio State sweatshirt, fleece and snow boots so I was quite comfortable in the car while I waited.

For once, the weather people were dead on, on their forecast and we got between six to eight inches of snow before the temperature plummeted to below zero (F) temperatures. We have a fairly new furnace and plenty of supplies so we should make it with no problems until the temps rise back up in the middle of the week. In true Cincinnati style, the high temperature will be near fifty degrees.

In January Liz and I have another vacation planned to go south to warmer climates, and sometime I am going to venture out to our local pharmacy to get another Covid booster. Hopefully, this shot will keep me out of the hospital which is what happened last year when I caught Covid and ended up in the hospital for three days in Georgia in the Atlanta area. It’s not until the 24th of January but time flies when you are having fun and will be here before I know it.

In the meantime, I know the brutal winter weather is affecting large portions of the country, along with flooding in the Pacific Northwest so I hope you are surviving the best you can.

Saturday, December 13, 2025

Survival as a Trans Girl

 

Image from David Gavi on UnSplash.

If you are a transgender woman or transgender man, you are a member of the survivor tribe. You have earned your spot through too much trial and error that a “normal” human simply would not go through.

I know there are many of you who are early on your gender transition paths that really need a survival pep talk. My pep talk would be…to try to stay on the bumpy path you are on because it will be full of sharp curves, stop signs and steep walls in your way. What is that old saying? If it doesn’t kill you, it will only make you stronger sadly happens in record numbers to the trans population. In fact, I tried to kill myself several times due to the amount od stress and depression I was feeling through my gender dysphoria. Fortunately, I was unsuccessful at my self-help attempts and lived to talk about it.

Even to this day, I still have to keep a close eye on how I am feeling mentally, and I still take meds for depression and anxiety which have very little to do with my gender issues. I suppose we all have our own weight to carry through our lives, and that one is mine. I am also fortunate in that I have mental health and LGBTQ support groups to attend virtually every Friday at the Dayton, Ohio Veterans Administration. In the group, we have a diverse set of survivors with different experiences to share, and the moderator always starts the session with what good things have happened to each of us every week. It is so successful that anytime now I think the henchmen from the orange crook in Washington DC to catch wind of it and have it cancelled. So far though, it seems to be OK. All I can say is, I have been in many support groups over the years with little to no positive results, so I hope this one lasts.

If you are feeling lonely and need like minded individuals in the LGBTQ community, seek out local groups in your areas. I know it is difficult for those of you in isolated areas but maybe you can do it virtually online. And, if you are jaded like me, don’t expect too much too soon from the groups you are in. Often, these are highly insecure individuals in the group who are reluctant to share until they know you better.

Then there are the ultimate survival tests such as spouses, family members and jobs. Each one of you will have to face your own challenges in these areas and the only thing I can say is, you have to be patient and try to use common sense when telling the world about your seismic gender changes. In my case, my second wife knew I was a cross dresser from day one of our marriage and never stood in my way but totally refused to have anything to do with me going on HRT and being transgender. She told me there was no way she would live another woman, and I understood what she was telling me. My second strike came with my employment. I had a very successful high energy job I worked hard to get and knew there would be no way I could transition on the job. At that point in time, I did not know what I was going to do to survive and continue my dream of living as a transfeminine person.

Perhaps you are blessed with a more understanding wife, and I would suggest a sit-down talk with her before appearing cross-dressed in your best feminine clothes. That way, you can tell what she is going to do and will she ever come to accept you. Then you can make plans for your survival.

Remember too, there are various stages of development as a transgender woman. First of all, you have to accept you are much more than a cross-dresser who can survive on fewer days a month dressed. Even though I had free reign to dress a couple days a week from my second wife, it was never enough to satisfy my need to go behind the feminine gender curtain and learn more. Even though it doesn’t sound like I took a slow and cautious path to my own form of womanhood, I certainly did. I wanted to make sure I could survive when I came out for good.

The amount of introspection alone makes you a better person and more of a survivor than the normal person. To have the chance to experience intimately both sides of the main gender binaries is the reason why some shallow people will never trust you. At some point to survive, you have to learn to accept the fact that you have reached a point where you are better than them. Plus, if you happen to be a person who thinks change is good, you are in for the most change a human can attempt.

When you are a survivor, you will join an elite tribe of humans who have walked an incredible path and lived to talk about it. If you are considering taking the path, just try to reach inside your inner soul to determine if the path is right for you. In my case, when I did, I came up with the answer that it was the only direction I could take and if I did not my life would not be worth living after all. My life then went full circle and a ciswoman who accepted me picked me up and made me the person I am today. I made it through all the self-harm and destruction I tried on myself just in time to transition into a transfeminine world in which I could survive. Hopefully, you can too.

 

 

Friday, December 12, 2025

When a Trans Girl is Serious

 

Image from Bruce Mars
on UnSplash. 

When I first came out of the closet, I wondered how I was ever going to convince the world I was serious about jumping the gender border into my transfeminine world.

Probably, before I started to convince any strangers of who I was, I needed to totally convince myself. Was I a cross dresser, accomplished drag queen or what. The last thing I wanted to come off as was some sort of a clown putting on a dress and makeup for laughs. I think, all the time I spent practicing in front of the mirror attempting to learn the art of appearing as a woman paid off. Because in a fairly short time, I was presenting as a convincing transfeminine person in the public’s eyes. I was far from being the most attractive woman in the room but at least I was making do with what I had to work with and getting by and the public perceived me as being serious also.

At that point, I was not getting the negative feedback I used to get when I left my male self and traveled to the feminine side of life. The worst that was happening to me was when other ciswomen gave me a knowing smile. Showing that they knew I was attempting to play in their sandbox or world. Even better was when I began to see the same people over and over again and they knew I was serious about where I wanted to be in their world.

As I gained more experience and began to understand all the layers which existed in a ciswoman’s life, I knew I had a long way to go if I was ever to be successful in pursuing my gender dreams. Then I purposely set out to try to experience new situations as a transgender woman because my feminine workbook was given to me blank. I did not have the same benefit other women had by growing up out of a female birth into a woman. I was doing it exactly opposite as I was trying to leave my male birth rite behind. Something that I had never asked for. Each time I successfully conquered something new in life I tried to experience, I looked for other things to do that I had never done. An example would be, once I conquered just going to bookstores and searching for books on gender, then I gathered the courage to stop at their coffee shop for a cup o joe. After that, I took it a step further and used the women’s room to wash up and check my makeup.

By now, you probably are getting the point of how I was branching out and expanding my life as a new trans woman. The world was becoming so new, exciting and scary that I was like a kid in a candy store and could not stay away. Even if I wanted to, which on certain days I did when I felt all my gender issues were out of control and my male self along with my second wife were aligned against me pursuing a transgender life any farther. The problem was that my inner woman was telling me the path I was on felt so natural and deep down I knew it was the right way to go.

Still, I tried to stick it out and try to maintain a presence in both my old male world and my new transfeminine one. By doing so, I certainly did myself and those around me more harm than good. Very simply, the stress was too much for my already frail mental health, and I took it out on myself and those around me. I needed to figure it all out and get very serious about how I was going to run my life before it was too late. Internally, I was out of control while externally I was just trying to hold on to my wife, job and family as I knew it. I would have not wished what I was going through on my worst enemy.

Thankfully, destiny stepped in and showed me the way.  My wife of twenty-five years tragically passed away leaving no major hurdles for me to move ahead with my plan to start gender affirming hormones or HRT. Amazingly, at the same time the Veterans Health Care System which I was/am part of approved a program of affirming hormone therapy along with a therapist to go along with it. Which I took advantage of immediately. Under her care, I became ultimately serious about the direction my gender transition should take, and I even went to my therapy visits as my authentic self. Even better, my therapist helped me change my legal gender markers within the VA and provided me with the documents I would need to change my other legal markers such as my driver’s license.

Changing my legal name and gender markers finally proved to myself as well ss my inner female how serious I could be about my future. Even still, with all I was doing with my life, a little voice kept telling me I should not have taken the easy way out and tried to get serious earlier in life about who my true self really was. Of all people, my second wife told me to do it on several occasions during the fights we had about what I was doing along the way on my gender path. It turns out I was going to travel it with or without her and it was my duty to make the call that I had to do it alone.

Sadly, I think most transgender women and trans men have a lonely path to follow before they are fortunate enough to find someone to share their path with. It is surely difficult to negotiate alone, and you certainly have to be serious enough to do it.

 

                                                                                                                                                       

Thursday, December 11, 2025

Trans Girl and the Christmas Season

 

Image from Roberto Nickson
on UnSplash.

Little did I know that Christmas would pass Halloween as my favorite season when I transitioned genders to the one I wanted. There were several factors which contributed to the change I was going through.

The first one was the ease I found I could get lost in the Christmas shopping crowds when I shopped as a trans woman. As long as I followed my fashion instincts. I learned I could follow several different shopping paths. For example, one day I could dress up and go to an upscale mall, and on the second, I could dress down and go shopping at a nearby local antique mall. I enjoyed the feminine freedom of choice immensely.

The second main reason I came to love Christmas so much more was I could really get into the spirit of giving. For some reason, being my transfeminine self-slowed me down and encouraged me to choose more thoughtful gifts for the people I cared about.

The third man reason was I could get lost as a woman in the hustle and bustle of the season. I forgot all about the buy something quickly and move on person I was as a man. My second wife was a huge gardener which made garden themed gifts popular with her, so I could shop at both style of malls for her garden gifts…new or vintage. In particular, I remember finding her a vintage seed merchandising box which she ended up cherishing in her collection. Right or wrong, she never found out my male self-did not buy it at all, my transgender side did.

Reason four was shopping as a woman took all the guilt of sneaking out of the house dressed as myself to buy gifts. I told myself I was not cheating on her when I did it if I was buying her a gift. Probably not the best reason in the world, but at that time it was the best one I had.

Reason five was that Christmas was such a longer season for me than Halloween. Halloween was an intense build up just for one day, and then the let down set in. Christmas of course lasted much longer, and I had the satisfaction of knowing my feminine self-bought all the gifts under the tree.

The final reason I can think of is since my wife always had a special gift giving night for my transfeminine self, I always felt guilty when I came up short for gifts for her. She was not much into makeup and fragrances and such, so the traditional ciswoman gifts were out. She never found out all her gifts could have been given out that night because of who they really came from. Instead, I ended up letting her open a few gifts at a time before Christmas itself.

Christmas at my house and my restaurant became a major holiday from the point of decoration. My wife had quite the collection of animated holiday figures, some new and some vintage which I was expected to find a way to display. As I did, I was put in a festive Christmas mood and made me more impatient to join the masses and do more shopping. Or at least all my finances could stand. Through it all, I was gaining the all-important confidence I would need to consider if my transgender dreams could become a reality after all. I could only discover if I was on the right gender path by the trial-and-error method. By attempting to stay out of the mirror and let the public tell me if I was right or wrong. I don’t know if the public was kinder at Christmas or not, but for some reason I was getting by and enjoying myself as a transfeminine person even more.

All these Christmas holiday positives did not leave me like the Halloween ones did. They became ingrained as I built my new life. A trans girl at Christmas soon became a trans girl period. All my learning gave me a new foundation to stand on when my life hit the skids, and I nearly lost everything. I lost my wife, what close friends I had, and my restaurant within a two-year period to death and recession. As it all crumbled before me, my feminine self-stood strong and ready to help. All I needed to do was let her with no strings attached. To ensure I could make a living until I could retire, I sold all the vintage items I had accounted for and was able to make enough to pay my back taxes and then retire from a job I hated. It worked because then, I would not have to worry about transitioning to a new job.

Now, since my second wife and her love for Christmas has long since departed, my daughter has converted to the Jewish faith and my wife Liz is wiccan, my overall interest in Christmas has waned. However, I will forever remember the festive seasons I went through in my past which helped me along so much in my male to female transition. I developed the instincts I needed to survive in a scary, exciting new feminine world. Being a trans girl at Christmas really worked out for the best for me.

 

Wednesday, December 10, 2025

Did I Take the Easy Way Out?

Image from Nicloe Geri
on UnSplash. 

 Yesterday I wrote about the seismic gender changes I went through or could have gone through in my life.

After I did, I began to think about where I took short cuts or took the easy way out of my new life as a transfeminine person. Maybe when you read yesterday’s post, you noticed it was primarily about the men who briefly entered and influenced my life as I questioned my own sexuality.

The fact of the matter was, I was afraid of having sex with a man. Mainly because I had never considered it as I was always connected to women. I wondered as I transitioned farther would my sexuality eventually change. Especially when I started HRT or gender affirming hormones. I knew when I did that, I was sacrificing any way of having so called “normal” sex with ciswomen would be gone as long as I was on the hormones. To be honest, I had always looked at sex as a way to please a partner rather than myself, so losing my sex act would not be that big of a deal. Plus, in my mind, I always made love to a woman as another woman anyhow.

As I write about often, as I transitioned, men for the most part left me alone for any number of reasons. I always felt the primary one was they knew I was transgender and had left the men’s club for good and they did not trust me with their own frail male sexuality. Or maybe I should say, trust themselves. One way or another, I immediately felt as if ciswomen accepted me quicker and I had never had so much female attention in my life. I loved it, as I was able to learn about their world while they were curious about mine. I even went as far as Amy telling me to buy bananas to start practicing what I would do with a man. I never did go that far except for the one big burly, biker of a man I met coming off of his wedding debacle rebound in a regular venue I went to.

I also knew his wife who was a beautiful exotic dancer and I could not figure out the attraction except for looks. It turns out that I was right and the marriage only lasted one week and I felt so sorry for him while at the same time, the people around him were making fun of him. Instead of taking the easy way out this time, I was the only one to lend a sympathetic ear to his problems. In a short while, he began to look for me (and vice versa) when we were at the venue because I was normally alone. Looking back, I wonder what would have happened if I had shown more curiosity about his Harley and would it have led to taking a ride with him. All I know is that I never did and he ended up taking a new job out of town and any possibility of me going any farther with a man sexually with him. From then on, it was back to women.

By women, I meant back to my new inroad into the lesbian culture and community which started when I began to frequent several small lesbian venues in the Dayton, Ohio area. Initially, I was just looking for a friendly place for companionship with other women. Out of the three venues I went to, I discovered they were all different in how I was treated. One of them hated me and did everything they could to keep me out of there, one was neutral and did not seem to care at all, and one was very friendly and welcomed my business. I even learned the bartender I saw several times was a customer in my restaurant with her friend. Her acceptance paved my way for several eye-opening experiences for me in the venue with other lesbians. Before I did, I needed to learn the social levels that other lesbians operated at. Everybody from super butch masculine women to more feminine lipstick lesbians who I more closely identified with. Along the way, I was hit on several times including the time I was forced to sing karaoke with a cowboy hat wearing super butch who wondered why my voice was lower than hers and another night when another butch told me she should take me home with her. Both were eye opening experiences.

What my dealings with the lesbian culture really taught me was that I did not need a man to validate my existence as a woman and there were many lesbians who might walk that fine line sexually to be with a man who was quite different than anyone they had ever known. It was my wife of over a decade now who decided to cross her lesbian leanings and attempt to build a relationship with a transgender woman. After a long courtship, I decided to throw caution to the wind and sell my house and move to Cincinnati to live with Liz. The deciding factor was she had briefly known my old male self and had completely rejected him. Telling me she had never seen any male in me at all.

With that major decision behind me, I was encouraged to proceed with HRT and give all my male belongings to thrift stores and live fulltime with Liz as a transgender woman. It was the biggest seismic change in life I could have ever made. Maybe I was taking the easy way out by never learning if I could live with a man because they were exceedingly hard to find. Ciswomen were not, I was enjoying myself and learning at the same time how I could reach my dream of living as a transfeminine person, so I never looked back. My world settled down, and I learned to live without all the seismic gender changes I went through.

 My path was never easy, but I ended up with a wonderful knowledge of the two basic binary genders.   

Tuesday, December 9, 2025

Transgender Game Changers

 

Image from Andre Fonseca
on UnSplash.


One of the positives to being able to live a long life is to be able to look back on all the key moments in my life when a decision one way or another could have made a huge difference in my life.

Perhaps the biggest moment was when I discovered the enchantment of looking at the pretty girl in the mirror where my boy self was just standing. Sadly, the moments were fleeting as my life was calling me.

As I grew up and my life became more complex, so did my dealings with my transgender issues. One of the most important lessons I learned came early when my second wife and I encountered a handsome Harley motorcycle rider at a tavern we were at one day in Cleveland, Ohio waiting for a transvestite mixer we were going to, to start. I was very new  to being out in the world as a cross dresser and was completely surprised at my reactions when this guy came into the bar and started flirting with my wife. Then, I was even more concerned about my wife when she started to flirt back, completely ignoring me. What was I going to do since I was stripped of all my male reflexes of what to do when another man was flirting with my wife. I had to just sit there and be quiet and hope she did not go for a ride on the Harley with the man. Of course, my wife sensed my concern but let the situation play itself out to teach me a lesson in feminine competition. One I never forgot.

Another evening, I never forgot and could have been a bigger game changer than it was, was the night I had my makeup done by a professional makeup artist in Columbus, Ohio at another transvestite-transgender mixer I was attending. After the makeover, I was stunned at all the positive changes the artist made for me. I was flattered with all the compliments I was receiving and decided I did not want the evening to end early. I wanted to join the so called “A” listers who always went out on the town and show off my new look. Plus, for some reason, my wife decided not to go to this mixer, so I was free and on my own. We ended the evening at another tavern which I could not tell was LGBTQ friendly or not but one way or another I bought a beer and headed for one of the unoccupied pinball machines. When I did, amazingly I was approached by a younger good-looking man who wanted me to stay and play pinball with him. By this time, the rest of the “A” girls were ready to leave, and I needed to make a split-second decision on if to stay or go. Since I had no idea if the man knew my true gender or not, and I was in a strange city, I decided to go with the “A”’s who were jealous of me because I was approached by a man and they were not.

I never knew what would have happened if I had stayed and would the evening change my life forever, which also happened the night I went on a date with Bob. By this time, my wife had passed away, and I had not met Liz yet (my future wife) so I was free to explore my own boundaries. Bob was not from my area of the country and on occasion passed through the Dayton, Ohio area on business where I lived. On one of those nights, I knew he wanted to meet me in person at one of the venues I was a regular at. I had never partied with a man at a sports bar before, so I did not know what to expect. What I did not expect was the great time I had. It was the first time in my life that I had been treated completely as a woman, and I loved it. It was even a karaoke night, and he sang for me. And yes, Bob did know I was transgender. We shared a rather passionate kiss together and the night was over. Never to be repeated again.

There were other trans game changers such as girl’s nights outs and the conversations I shared with a man who I thought I could have gone farther with if he had stayed around. The “what if’s” remain big questions for me as I grow older, and I know you can’t have it all. In many ways I crammed a lot of life into my years which I am grateful for.

I should not be selfish though because I have been blessed during my life with people who have loved me, and I did my best to love back in return. Sadly, my gender issues were in my way through most of them and if I had faced reality, I could have been a better transfeminine person. Which is a topic for another blog post altogether.

 

 

Monday, December 8, 2025

Tiny Ripples of Gender Hope

Image from Rosie Kerr on UnSplash.

During the overwhelming sense of darkness I felt when I began to come out of my gender shell, were moments of gender hope and euphoria. More than anything else, they kept me moving slowly towards living my ultimate dream. All I could think of was the possibility of living as a woman later in life.

Having to run and hide my small “collection” of feminine clothes and makeup every time I tried to get in front of the mirror and cross dress did not help. I resented the fact I could not be free to do what I wanted, no matter how radical it was…like being a girl. I could not imagine the pain and suffering I would have if I was caught. What saved me was the vision of a pretty young girl which came peeking on through when I was able to be alone and try on my precious clothes. Even though I was depressed I had to go back to being a boy, the brief moment of femininity carried me through the dark days and gave me a ripple of hope.

Fast forward through the difficult days of puberty and adolescence everyone goes through, I needed to deal with my gender dysphoria also. There were so many dark days when I just went through the motions of life that I did not know what was going to become of me. When I did, I desperately needed to find refuge behind my dresses and makeup to give me hope. Perhaps the only good thing which was happening was that I was slowly perfecting my use of makeup. When all my friends were showing off their painted model cars, I was stuck not being able to show off my new eye makeup. I had to internalize my feelings of hope and euphoria when I saw my new pretty eyes. Sadly, I needed to become good at removing all traces of the makeup so my brother and parents would not notice.

I guess you could say I was in the dark through my college years and beyond until I began to be able to enter the world for the first time as a novice cross dresser or transgender woman. These were the days of attending transvestite mixers and small parties in nearby Columbus, Ohio. Being around like minded people who were searching for their gender answers almost made my search seem normal for the first time in my life. I was so protected from the world in the pre-internet days that I thought I was the only one like me stuck in their own personal hell. I was experiencing ripples of hope for the first time in my life on a scale I could appreciate. I even upped my appearance game when I went to Columbus from trashy woman to hopefully a passable ciswoman. One of my favorite outfits to wear was what I called my knit black out. I paired a loose fitting black wide knit top with a black leotard, shorts, tights with a pair of black flats and my red wig and was ready to go. After makeup of course.

For me, the whole outfit helped me to tone down and refine my look and it worked so well that I had my first ever encounter with a lesbian from the party when we left and went to a big lesbian venue for a break. I learned many valuable lessons that night which provided me with ripples of hope for the future. Mainly, if I could not be as feminine or beautiful as the transsexuals who were there, I still could be attractive myself to have a good time and most importantly, learn to be just me. Developing the future, me gave me real hope for the future as I learned it would be possible to achieve my transgender dreams if I worked hard enough. I had to learn the new transfeminine me meant so much more than the ripples of hope I had gained in the past went way past how I looked and into how I acted.

Suddenly, acceptance became my main goal, as my interior feminine self-stepped forward in my life. I knew who I wanted to be but still was not quite sure how to get there. For example, I knew for sure I did not want to be like the “Trans Nazi’s” as we called them or the bitchy trans women who thought they were better than anyone else simply because of their appearance or the number of gender surgeries they had undertaken. I suppose I should owe them a debt of gratitude for showing me what not to do to be a gracious, friendly transgender woman.

All of this came together for me when I began HRT or gender affirming hormones when I was sixty. I had spent enough life in the dark to appreciate the light and grasp a ripple of hope when I saw it. The hormonal medications proved to be a natural success when I began taking them. My body seemed to be saying again what took you so long. But on many levels I don’t think even I understood the basic limits I went through back in those days to salvage my life through the brief ripple of hope I received way back in the days when I lived for the mirror.

More importantly, I found myself in a situation where I could pay forward my experiences to helpfully help others. Especially those of you who are struggling to find answers on how to escape your dark gender closets and find your own ripple of hope. 

Sunday, December 7, 2025

The Rise of Transfeminine Privilege

 

JJ Hart (Middle) wife Liz (Left)
daughter (Right)

When I began to seriously leave my closet and mirror and attempt to join the world as my true self, I quickly lost all my male privileges and gained very few feminine ones. In fact, early on, the only privilege I felt was having doors opened for me by the men around me.

On the other hand, the most extensive male privileges I lost were my intelligence and my personal security. When I was around men, I learned to keep my mouth shut until I was spoken to, which was not very often because I think most all men knew I was transgender and wanted no part of me. And as far as personal security went, I needed to learn what ciswomen know from an early age to keep themselves out of possible bodily danger by being in the wrong place at the wrong time.

All along, during this time, I was wondering when and if the gender teeter-totter I was on would balance itself out and I would see the positives of what I was doing. It took a combination of things happening before I ever did. One was seasonal around Christmas, and the other one was when I decided to give up on men all-together and concentrate on knowing other women. A preferred topic in my mind, since I did not have to consider changing the focus of my sexuality, which had always leaned exclusively towards women. But I digress, the meaning of Christmas and what it meant to me as a transgender woman, is the real reason for this post.

To begin with, Christmas was always a major holiday for me and my second wife especially. Finding an exceptional, unexpected, rare gift was always the priority for me and even my brother’s family. The difference became to me was when I decided the Christmas shopping, I had been doing as a man would be much better accomplished as a woman. If I was able to pull it off, I could accomplish so much more during the Christmas rush I was in the middle of.

First of all, I needed to up my crossdressing game to give me the best possible chance to succeed in my shopping conquests. I went through my closet and pulled out my fancy, sleek, black pants’ suit for trips to upscale malls and my leggings, boots and sweaters when I combed through the huge local antique malls for just the right gift for my wife. I knew if I was to succeed, I had to be better than the average Ciswoman so I would not be potentially embarrassed. Also, the right makeup and hair was a priority because of all the up close and personal time I would be spending in the public’s eye. Through it all, I wondered where the magical feminine privilege would kick in for me.

The first major time it did was when I was shopping for a matching oak bookcase for my wife’s roll-top desk. One night, I found one which worked beautifully in an oak furniture store in nearby Columbus, Ohio. It just so happened I was returning from a shopping trip to a local Columbus upscale mall when I stopped into the store on the way home. After I found the bookcase I wanted, my old male self-wondered how in the world would I get it in my truck/SUV. Would anyone come to the aid of a tall blond in a black pants suit and heels? After I paid, I found out they would because for the first time in my life I was able to sit back and watch two young men load the bookcase carefully into my vehicle and finished their job off with a nice thank you mam. Because I had finally discovered a dose of feminine privilege, the half hour trip home went quickly, and I wanted to do more shopping, but I was out of time and money.

Sadly, once I returned home and had safely unloaded my prize gift, it was time to return to the place I did not want to be…my old male self. On the plus side though, the whole experience taught me (and provided the confidence) to move forward to my dream life of being a fulltime transgender woman and would not have to return home every night in a hurry to switch back into a gender I wanted nothing to do with. My feminine privilege was being established in the newfound senses I was feeling. Especially when I was doing something for others, such as buying gifts.

The experience made all the learning and trial and error experiences I went through during my male to female femininization process deeply worthwhile. There were other Christmas stories to share as I will do later. Such as when my wife decided we would have a special gift giving time for my feminine self.

 

 

 

 

More Gender Dreams

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