Saturday, September 19, 2026

Is It too Early for Halloween?

 

Early fall Image
JJ Hart

As I look around the neighborhood I live in, I see people putting up their Halloween decorations already.

Then I began to think of the supposed “good old days” when about this time in September that I was starting to seriously consider what “costume” I would wear and how could I maximize its use by going to as many parties as possible. It just did not seem fair to me that I had to wait for a once-a-year party to express my feminine side without the fear of retribution. The worse that could happen to me were the other women at the party asking me who helped me with my makeup and did I really shave my legs for one night.  I was learning a valuable lesson about how curious ciswomen could be when you cross the gender highway into their lane.

Basically, my biggest decisions came as I thought about which theme I would follow year to year if I was going to the same party. And how creative could I be with my “costume” Ironically, my first big attempt at dressing feminine at a Halloween party came when I was still in the Army in Germany, when I was invited by my future wife to go to a hospital’s party. I had a couple of other wild friends who had their costumes already picked out and were coming as various forms of the male and female anatomy. So, I thought it would be an ideal time to fall from my cross-dressing wagon that I had been forced to be on for two and half years and come as a trashy prostitute.

I do not remember now how I got the clothes I needed to complete my outfit, but I was able to put together a short mini dress, long blond wig, hose and heels for a very effective costume. Since I still had approximately six months to go in the Army at the time, I was happy that no one seemed to care that I was dressed as a woman at the party.

When I was discharged from my military duty, and Halloween rolled around, I had a different challenge to face with all the newfound freedom I had. One thing I did was get away from the prostitute look and try to find a way to find a “costume” like what a ciswoman would wear.  In other words, I wanted to go to the party and try to pass as another woman enjoying herself. During the first multi-party Halloween night I went to, I think I did well. I went as one of the French girls I had seen in Paris when I was in the Army and brought the look home with me. I paired a all-black outfit which featured black tights, mini skirt and leotard with my blond wig, red lipstick and topped it all off with black flats and a black beret.

I was having a very good time entertaining myself in one of the big local clubs I went to which was having a Halloween party when a guy in a full mask approached me and simply said “I know who you are.” At first, I needed to recover from his comment before he went on to say, “I know because you look just like your mom!” Then I knew who he was and did not know whether to be flattered or not before he did not say anything else and went on his way. I did know I looked like mom but not that much.

From then on, I began to build my Halloween “costumes” from scratch and only used my many trips to thrift stores to help me with items for what I was going to wear. All I really knew was that I enjoyed my self immensely in my new world as a transgender woman and wanted to see if I could take it past the party scene and into reality. There would be other significant parties I will write about later, for now I had to learn if the build up to Halloween was totally worth it. I learned it truly was because of all the early lessons I would need to learn if I was ever going to decide to try to cross the gender border and live full-time as a transfeminine person.

I also realized that Halloween would be just the briefest thrill in what would be a long life of gender discovery. Would the overall gender euphoria of making it through the parties successfully be worth it when I had to crash back to reality and my increasingly boring male life. Plus, I found it was unbearable for me to just wait a whole other year to experience my feminine side again without me going out in public. I took my gender life into my own hands and began to explore the world in malls and outside in different venues such as bookstores which helped me build my confidence as a novice trans woman.

I went further, quicker than I ever thought I could and forever put Halloweens behind me as a necessity in life and more of a fun pursuit. In its place, I would be trying to carve out a brand-new feminine life of my own. It was the beginning of the most terrifying yet exciting time of my life. Mainly because I was stripped of all my old male protections and had to start all over again in a world where I did not know who to trust. Including myself because everything I knew was changing when I left the good old boys’ club for good and applied for membership in the girls’ club that I had so long waited to join. I was just at a point where I needed to convince ciswomen around me that I was serious and brought different qualifications to the feminine table. I had to suggest I was a woman too but just had been socialized a different way than they had been.

In many ways, Halloween was the earliest part of my socialization process thanks to the early interactions with ciswomen (and men) that I experienced. Immediately, I found that men I had known for years ignored me as a potential cross-dresser or whatever they thought I was. It did not matter. I was out of the club.  While at the same time, women I had known for years were curious about me. Lessons that had carried with me well in the learning years to come.

That is why I will forever miss the early excitement I felt around my early Halloween parties and why I still feel the fun I felt when I see the neighbors putting up their decorations early. Who knows, there may be a person in the family with gender issues also.

 

 

 

 

 

Thursday, September 17, 2026

Torn Between Two Lovers

 

Image from Hanna Lazar
on UnSplash. 

There is nothing romantic when you are being torn between two lovers if you are a transgender woman or a transgender man.

For me at least, I would never have wished for the ripping and tearing I suffered from the gender dysphoria I suffered from on my worst enemy. Waking up each morning wondering which gender I would be today was certainly no walk in the park. if I did take a walk in the park, it would be a mental one, and I would be chased by my demons.

As I write about extensively, I was stuck in my dark lonely gender closet as I felt as if I was the only one in the world who felt the same way I did. It was back before the internet and social media days and any information on gender issues was difficult to come by or out and out false. For the longest time, I just did not know where I fit in the world as a man who wanted to be a woman.

The tearing became even worse when one of my identities started to surge ahead of the other. It happened when my daughter was born and I had to get much more serious about how I was going to build a career as a man. Only to be ripped back when I viewed myself as a trans woman in front of the mirror. I only had the annual Halloween parties to get out of my closet and see what the world would be all about if I had the chance to live my dream of going full-time.

The thing about dreams is that they are a long way from reality. Reality meant I needed to go a very long way to learn about what I was trying to achieve. Back in those days, the term transgender woman was brand new and barely used, so I was surprised when I discovered it and it fit me so well. Keep in mind that I could only refer to myself as a transvestite because I knew I was not ready to use the transsexual label then or ever. If I had the will power to go through the major gender realignment surgeries of the time, I certainly did not have the insurance coverage or the financial resources to do it myself. Again, I was just stuck between two genders, but at the least I had a label now for who I was.

The ripping and tearing managed to become even worse when I began to improve my feminine presentation to the point where I could blend in with the world of ciswomen around me. Every time it happened, my male self would become upset because he was losing his hold on my life. As it was becoming increasingly evident that someday, I would have to choose between my two very serious gender lovers.

At the same time, I was trying everything to maintain my already fragile mental health by going to therapists. By doing so, I was able to learn what being bi-polar depressed meant and why I was suffering from it. All along, I was blaming my severe depression on my gender issues when I had other often more pressing issues. At the same time, I was ignoring facts from my therapist that she could do nothing about me wanting to be a woman. It turned out to be my truth that I refused to follow. Instead, I tried to move on. Going the wrong way on a one-way gender street. Dodging the sometimes-toxic public became too much of me until I began to give up totally on my male side and concentrate on living my dream of being a transfeminine person.

I never labored under the idea that my life in the world as a trans woman would be easy but I never bargained for the complexity of the new life I was facing. It seemed that every time I was able to overcome one obstacle on my path, something new would appear to take its place. Like never before, I had to really listen to what people were telling me, so I would miss nothing in the conversation. I found that trying to live in a world of ciswomen meant more than just looking the part. I needed to be the part too. Always before as a man, it was easy for me as a man to zone out in conversations and then catch up when I wanted to, but impossible when I began communicating one on one with other women.

Of course, my male side always hated losing, and every time my female side showed any victories, he hated it and fought back harder. As he was trying everything, he knew how to maintain what was left of his life. To placate him, I would try to do as many male things I could such as drinking with the few true male friends he had left. The problem was even he was beginning to feel alienated from his old friends as they started to pass away from cancer. At the same time, my feminine self was very successful in carving out a new life she could sustain as well as feeling so natural doing it. It was becoming obvious as the ripping and tearing (and even a large part of my depression) began to go away that I had chosen the right path to take on my gender journey.

At the same time, I began to consider attempting to get approved for gender affirming hormones or HRT. First through an independent doctor and then through the Veterans Administration healthcare system which had just approved it. It was as if the long-closed doors which were preventing me from living my transgender dream were suddenly swinging wide open. From then on, the only ripping going on was over what male baggage I could not take with me into my new life. My male clothes were given to charity as I built up my wardrobe for a new everyday experience as a transgender woman. It was a terrific weight off my shoulders.

My hope for you I that you can overcome your inner turmoil faster than I did by facing your truth. Thanks for reading and commenting!

 

 

Wednesday, September 16, 2026

Discovery in a Trans Life

 

Image from Spencer Davis
on UnSplash. 

Without knowing it, my life has turned into a path of gender discovery. When I woke up this morning and looked in the mirror, I discovered yet again what the magic of HRT hormones had done for me and how fortunate I was to be in the situation I was in. But it was not always that way.

Like many of you, my discovery began when I was spending too much of my time as a youth exploring my mom’s clothing and makeup. From that point forward I was hooked as I tried my best not to destroy any of mom’s clothes as I outgrew them. Possibly, I was successful because she never said anything to me about her wardrobe which was fairly extensive for a high school teacher back in those days. In the 1960’s.

Very early on, as I was making gender discoveries left and right, I ended up refusing to accept the most important one. That my life was much deeper than just wearing girls’ clothes in front of the mirror, I really wanted to be a girl. If I had the information tools to know it, instead of just liking the clothes and the look, I was in fact, transgender. The problem was, this was way before the internet and social media years, so I had no access to the world of cross-dressers than my occasional delivery of “Virginia Prince’s” “Transvestia” magazine. Once I received my newest edition, I could compare how I looked with all the other cover girls in the issue. To be sure, a real discovery came from every issue.

Perhaps, most importantly, were the back of the issue pages which I discovered advertised “Tri-Esssocial mixers for so called straight transvestites all over the country. Including ones in my native Ohio which I discovered were within driving distance of me. From that point forward, I wanted to personally attend a social and see where I fit into a gender system which I felt so alone in. When I gathered the resources and courage to do it, I signed up for a social/mixer which was a couple hours away from me. That sparked my first big discovery of my transgender life. By being around like-minded people for the first time in my life, I hoped my loneliness would go away. Sadly, it did not because I still felt alone in the middle of a crowded room. I am sure part of it had to do with my inherent shyness, and the rest from going through for the first time how it felt to be without my learned male self-protection privileges. Starting all over as myself was an initial shock.

In the protected world I was from, I had no idea of how many layers of people I would meet on the gender spectrum. My eyes were opened from meeting cigar smoking cross dressers who seemed to be denying the fact that they were there at all. All the way to the impossibly feminine transsexuals who had been on HRT and were headed to gender realignment surgeries. The problem was that I did not know where I fit in the new system I was seeing.

I just knew I needed to figure it out which meant a deep exploration into my inner self, no matter how painful it might be. Discovery then took on a new meaning to me as I explored the world as a transgender woman trying to carve out a life for herself. At the time, I was only going to gay venues to see if I could meet a like minded individual there but quickly learned I could not and took the next best step to try to test myself out by discovering if the straight world would accept me. By doing so, I found myself in all kinds of different situations in everything from small lesbian bars to big straight casual dining venues such as TGIF. After some scary beginnings, I discovered I could fit in on my own terms. Which surprised me beyond my greatest expectations. I was also learning that my goal of living an everyday life as a trans woman just maybe could be within reach. If I wanted it bad enough.

I did discover I did want a transfeminine life enough to sort out my male baggage I would not need on a male to female gender transition. It seemed my path for the first time was lit up like a new highway to my future if I wanted it. The best part was I was still discovering what it meant to be myself as I made a new world for my long-awaited transgender woman to emerge and live in. It is not often that a human has a chance to re-invent themselves and enjoy the challenge of doing it but I got there. I discovered by putting myself out there in the world I could build a new feminine life from the ashes of my old male life, I even went online and my wife Liz found me on a dating site, and we have been together for nearly fourteen years now. I was prepared at that time to spend the rest of my life alone and discovered I did not have to. It was a real surprise.

Over what has turned out to be a long life, I have been able to make many discoveries which have aided my progress in the world. Including more than a few which I never thought would happen such as my relatively easy time in the Army all the way to me being able to make my way to living a life as a fulltime transgender woman. While, at the same time retaining some of my most important male building blocks along the way.

I hope you have the chance to make your own discoveries in your life that you deserve. Enjoying your discoveries should be a part of your pleasure.

Thanks for reading along and comments are always appreciated.

 

 

Tuesday, September 15, 2026

Just Me

JJ Hart
Years ago, when I started to write a “blog”, I barely even knew what one was. I was urged on by a close online acquaintance that I had met on another site that I cannot recall now or even know if it is still in existence. My friend has long since faded away and I hope she is still with us at all as she had health problems when I met her.

What I remember the most is the number of entitled transgender women who were “post op” (had gone through some sort of gender surgery) and felt that they were better than the “pre opt” trans women who had no surgeries at all. They were for the most part very nasty and we referred to them as “Trans-Nazi’s”. At that time, I had several very in-depth experiences I shared, and my friend told me I had enough to share with the world. So, I did and to this day, I am still writing.

Years ago, I made a pledge to myself to try to help others with my writing because for the most part, we share very similar yet difficult lives. Over the years, I have been able to share all sorts of experiences such a the “Blue Coat” I cherished so much in a store but was never able to buy because the finances could not handle it. I so loved that coat, that I was overjoyed every time I went back to that store and it was still there. Actually, it was pale blue, full length, wool, and I thought it fit perfectly with my long blond wig and black silky pants suit. I was there so much that I thought the staff would notice the tall blond trying on the same coat time after time without ever buying it. Because she was just wasting mirror time admiring herself, but they never did and finally I just had to give up on having the coat of my dreams.

Maybe I should have felt guilty about my one-sided obsession to be an attractive trans woman without the help of any surgeries. Plus, at the same time keep my long term marriage alive by going against all the transgender theories of the day which said you had to go away, have gender realignment surgery and start all over again in a totally new life. I was too stubborn for that and wanted to do it my way with one foot firmly planted in two gender worlds, male when I worked or was with my wife and female when I was not and was going to the diverse social parties I was attending in nearby Columbus, Ohio. I loved them because I never knew who I was going to meet there and they could be anywhere on the gender spectrum from lesbians to feminine transsexual women headed for their surgery.

Even with the wide range of gender diversity I ran into, I still could not get over the fact that I still did not fit in yet with any of the groups I interacted with. Ironically, I did learn how well I interacted with the lesbians who attended the parties which set the stage for my future belief that I firmly was not into men but still enjoyed my time with ciswomen and we got along.

From Columbus, so to speak, I took my going out show on the road and begin exploring more frequently venues that I had always wanted to go to as a transgender woman. As I was busy kicking open my closet door, I was learning more and more about the resilient new me. I started to write about my good and bad experiences in the straight world I wanted to be in as I left the safety of the gay venues behind me. The safety I am referring to was sacrificing always being known as just another queen to trying my best to be accepted on a bigger stage in straight venues I enjoyed going to as a man. Then, I started to write about which male baggage (such as sports) I could possibly bring with me. At the time, as well as now, I added how important it was to judge your surroundings to determine what other ciswomen were doing. I have always tried to emphasize how important it is to not bring any negative attention to yourself as I used to do by trying to cross-dress provocatively when I first entered the world.

Speaking of the world. It began to open for me when I began to blend in with my target audience which were women. At that point I started to write about being allowed to play in the girls’ sandbox and being allowed behind the magic gender curtain that I cherished so much that I was willing to risk all the male privileges I had worked so hard for to get there. The more experienced I became in my new feminine world I became, the more important it became for me to write about when I knew it was time to pull the plug on my male life. The key for me was that my transition always felt so natural for me, and my only regret was that it took me so long to do it.

I also went through the who I am to give advice on part of my writing experience. From comments I received all the way to just realizing my thoughts were as relevant as anyone else’s, I forged ahead through years of writing. Making sure that my writings were grounded by the realities I had such as the days I spent with my friends at the monthly lesbian mixers I always went to with them. Or the “Andy Warhol” exhibit I went to with transgender friends back in Columbus at Ohio State University and how I needed to be careful not to come off sounding like a trans-nazi myself after I wrote about a group of drunken cross-dressers trashing a women’s restroom in a gay bar we went to after the exhibit. Rightfully so, after the restroom incident, lesbians in the bar got the rest of us banned from using the women’s room. I was trying to hide my disdain for what the cross-dressers did because I was not far removed from being a very serious cross-dresser myself. The last thing I ever wanted to do was put myself up on any sort of pedestal.

Since now, I have followed my life’s curves and transitions, at the age of seventy-seven I have transitioned into my true transfeminine self-fulltime and thanks to my wife Liz having been living my dream life since I was sixty. Transitioning with Liz made me feel like the real me which had always been missing was the final piece of the puzzle.

Hopefully, I still have many healthy years to write about my experiences in my quest to help others with similar gender issues.

 

 

 

 

 

 

 

 

  


Monday, September 14, 2026

Transgender Journey...Down but Not Out

 

Image from Alexander Grey
on UnSplash.

As transgender women and transgender men, it is easy to feel down and out as we try to navigate our new gender paths.

As I sometimes look back on my journey, it is easy to remember the good times and forget the bad. The most important thing about reliving the bad is having the appreciation for the world I am able to live in today as a fulltime trans woman. Every time I make simple trips in the world to the doctor’s, the Veterans Administration or the pharmacy, I always have to look back at remembering the not so good old days when I was struggling for acceptance. Either one of a couple things has happened. Either I have become better at my overall feminine presentation (wrong) or my confidence has taken me to a point where I don’t particularly care what the world thinks about me.

Either way, I look back to when I considered myself a very serious cross-dresser as I still was researching which fork in my gender path would I take. Back in those days, I took hours to prepare for an outing in the world, and I often wondered what I would do if I had to go out in the world everyday and compete with ciswomen everywhere. It was easy at that time to put those thoughts behind me as I was so obsessed with my feminine looks that my second wife kept calling me the “Pretty, pretty, princess.”  Naturally I loved the “pretty” part but rejected the “princess” part of her very pointed critique of me. One day, she even went as far as separating appearance from being a true woman for me when we were fighting about me wanting to go out. It was one of my all-time down moments when she told me I made a terrible woman. It hurt because I was not trying to make anything, I was just trying to express my true self, but I could not properly put my thoughts in a form she would understand.

I guess you could say, back then, I was definitely in my mental transgender formative years when my mind was trying to catch up with all the cross-dressing I was doing. Sadly, before I could formulate what a better version of my transgender self would be, all I experienced was an extreme amount of frustration. I could not understand what I was doing wrong when I was being successful in situations such as transgender-cross dresser mixers I was going to. The problem was the extreme gender euphoria I experienced at the mixers when I was mistaken for a ciswoman was not worth the resultant crash and depression, I felt when my life went back to its same old boring male self.

It all resulted in me being boxed into rarely getting out of my gender closet to explore the world and I was moody, resentful and not the easiest person to live with as I tried to internalize my gender feelings from my wife. A prime example was one year when we took a vacation from our native Ohio to the Upper Peninsula of Michigan. On the trip up there, I progressively grew more depressed and mean until my wife asked me what was going on since I was supposed to be having a good time on vacation. Predictably, I lied my way out of it and did not tell her the truth that I rather be spending my vacation time as a woman rather than a man.

Somehow, I pulled myself back together and the vacation continued without incident, but I remember it as another low point. Little did I know at that time, destiny would finally come back to me on my gender path, and I would get my wish to go on extensive vacations as a transfeminine person.

Along the way, I have had many other low points which I write about often. Such as when a woman called me a pervert for simply using the women’s room in a venue, I had been a regular patron of for a long time and had no one say anything negative to me at all. Then much earlier than that when I was struggling to blend in with the world at all, there were all the stares and even laughter I needed to put up with on my journey to present. I was reduced to tears more times than I care to remember mainly by groups of teen girls struggling to find their own femininity. I was certainly at a low point when all of this was happening to me, and I did not have the tools yet to know which way to turn. All I had was this little voice in the back of my head telling me to keep going and my low points would disappear.

All of it did go away for a while until I hit my dark age when nearly everyone I cared about decided to die within a two-year period. The group included my second wife and three of my closest male friends. Who were the only ones I had. To add to my low point, I was desperately lonely and ended up relying on that little voice who at this time was growing louder and more insistent that she had all the answers for me. This time, I had very few other alternatives to fall back on. As one person told me after I had lost my restaurant along to everything else, you will land on your feet. Not knowing my feet would be in high heels when I did it.

I am sure that everyone’s lives have its share of highs and lows and I can not say a transgender woman or trans man lows would be even more dramatic, but it seems possible because we have so much to lose as we pick up our lives and move them across the gender border. Until we find ourselves living behind the gender curtain where we always wanted to me.

Hopefully if you are in the midst of a low time, you have a little voice telling you everything will be OK. If not, remember life is but a circle and what is down will eventually come up.

As always thanks for reading along and comments are always welcome.

 

 

 

Sunday, September 13, 2026

It Was Always a Challenge

 

Image from Dwayne Joe
on UnSplash.

As a boy and onward to manhood, I had plenty of challenges to be sure of. Early on, my challenges were in athletics where I had very little natural ability, except for a passion to play ball of any sort.

On the positive side, my love for sports kept the bullies away for the most part and on the negative side, I lost a lot when I played. In the meantime, my feminine side beckoned and I was challenged even more because once again, I was not blessed with very little ability to present well as a girl. Testosterone tore my body up and produced many results that I did not want such as a bigger body and hairy legs and arms. Not good for a boy who wanted to be a girl as the major goal in her life.

At that time, I did not realize how complex my life would become when I decided much later to pursue the life of a transgender woman. How would I ever maintain a marriage as well as a successful career as a man that I was expected to do, if I wanted to be a woman at the same time. It was the beginning of an intense amount of pressure that I needed to live with as it became part of my permanent baggage when at the time, I was trying my best to minimize my life. Especially when I was in the military and almost everything I owned was being shipped home, on my back or in my duffel bag. I would never be free of entanglements in my life that I had then.

Then, even if I was trying not to add more baggage, life set in when I was discharged from the Army and marriage as well as my first and only child were quickly coming my way. All along I was conflicted about the new challenges I faced, I had set up basic guardrails in my life such as telling my first wife I was a confirmed cross-dresser or transvestite at the time and trying to use birth control which ended up failing on me which I will not go into.

I suppose I had no choice but to accept the new life challenges I faced with parenthood and trying to build a career for her and my small family as I moved along. It was what I was supposed to do, and I was trying to meet the demands of doing it. What I never counted on was the strength of my feminine inner self. She was always demanding more and I was on the verge several times of responding to her call when I had very little other male baggage to deal with. But I did not and went on to struggle with my gender dysphoria the best I could by internalizing it. The only release I ever had was cross-dressing in front of the mirror for my own pleasure as I dreamed how it would be to live a life as a trans woman.

A well-known path out for me became the exciting Halloween parties I could go to in my favorite costume…as a woman of course. The parties showed me I could begin to exist on my own terms as the person I always dreamed of being. If I answered the challenge to do it. If I had the courage to present myself to friends as a woman, could I ever decide to do it as another avenue out of my closet and into the world. While I was at the first Halloween parties I went to, the more I learned of the basics of being in a new exciting yet scary world where I always wanted to be.

I learned quickly that cismen around me would avoid me completely, while ciswomen asked me questions about who did my makeup and how did I gather the courage to shave my legs for my “costume”.  Later on, I used the basics I learned from the parties I went to when I tried to meet the challenge of being out with other women who wanted to communicate with and were still curious why I would want to meet the challenge of being in their world. By this time, I was becoming more confident in my true feminine self that the thrill of going to Halloween parties disappeared.

Just because the parties went away and my confidence increased did not mean that the challenges I was facing went away with it. I needed to face the complexities of living a life as a transfeminine person head on if I was ever going to be successful, I needed to communicate with a world which wanted to know more about me for the first time and it was the hardest thing I ever had to do in my life. It was the time I had always dreamed of when I could finally put the mirror behind me and put the total new me into motion. When another woman came at me with questions, I was there to answer hers and was beginning to be able to ask her questions of my own by looking her directly in the eye and doing it.

The only advice about overcoming the communication challenges you will face in the world I have is to somehow get out of your closet and experience what is going on firsthand. By doing that, you can let your own unique personality out into the world and leave your unwanted baggage behind you if you are a transgender woman or a transgender man. The same rules apply, just in different gender worlds you must live in and react to. If you do not answer your challenges and try your best to get out of your closet, you will make yourself a victim and never do it.

Also, the only warning I have is depending on where you live, know the anti-transgender laws and attitudes you will be facing and plan ahead accordingly. Remember you can not rely upon the old male security privileges you used to have and find yourself in a dangerous situation. Ciswomen are raised to be careful of potentially toxic situations and avoid them too.

You can also use your challenges as a mini-bucket list and move on after you have accomplished one goal. It is a relatively easy way to manage your male to female or female to male transition.

Good luck with your challenges and thanks for reading along. I appreciate you and any comments you may have!

 

Saturday, September 12, 2026

To the Dentist We Go


Image from Geo Days 
on UnSplash.


This is going to be another short post day because my wife Liz must go for an emergency visit to the dentist. Of course, we all have been in that situation before and if is a situation that you haven’t done, you don’t want to be in it.

As with my other recent doctor’s appointments going with Liz, I am wearing another of my “The Ohio State University” shirts because tonight is a huge game with Texas. Along with my leggings and tennis shoes.

Also, this morning I have already shaved closely, brushed back and tied my hair back which leaves me just enough time to apply a light coat of makeup and lip gloss. A routine I normally always follow if I am going to a place such as a medical appointment. Where most of the other people are involved in their own world, or the world of their cell phones. And will never notice a stray transgender woman in their midst.

Even though I don’t expect anything out of the ordinary to happen, I am always prepared for it in the back of my mind and probably will be forever.

If it does, you will be the first to know!

Friday, September 11, 2026

The Age of Gender Innocence

 

Image from Nicola Dowie 
on UnSplash.

I used to think that my initial days of cross-dressing were the most innocent days of my life. I was very young and the feel of the feminine clothes on my body and the expectation of seeing myself in the full-length family mirror brought me to the height of anticipation. For the moment at least, I was putting aside all the worries I had of ever being able to live successfully in a male world.

Now, with the benefit of age on my side, I wonder if I was ever so innocent. Sure, I loved all the things about being a cross-dresser such as shaving my legs and wearing panty hose, all the way to feeling all the sensations of being able to wear the same pretty clothes I had seen the girls around me wear. The biggest problem remained was that just the wearing of the clothes was never enough. The thrill I felt of dressing up was guaranteed to only last a couple of days before I could not wait to do it again. Even my young mind knew there was still something wrong.

What was wrong was I was not a cross-dresser at all; I was a transgender woman waiting her turn to live in the world. In the meantime, I would have to depend on the temporary thrills of mirror worship to get me by in life. It all set me on a very long path of gender discovery. Complete with many ups and downs along the way to make the journey either very scary or at least very interesting. It took me years of mirror living before I could ever gather the confidence I needed to finally conquer my fears and go out into the world as a novice trans woman. Of course, there were the on-going challenges of learning makeup as well as shopping for my own clothes on an extreme budget. When I discovered the thrill of shopping at thrift stores, I was able to find clothes that fit me well by having the chance to try them on before I bought them. If I made a fashion mistake when I got it home, it was not such a big deal because it did not cost that much to start with.

Rapidly, my days of gender innocence were fading away as I became more involved in the world of ciswomen. I quickly discovered their world was much more than just the external world of fashion, hair and makeup. Their world was so much more complex than a cisman’s I was not prepared for it. I found I had a lot of work to do to be accepted at all. To prove I belonged there at all, the first step was to prove I was serious about doing it. I would first have to prove to other women, I was not trying to enter their world as some sort of a dare, or that I was not up to something no good. I desperately wanted to cross the gender border and join the girls’ club and leave the men’s club forever. When I was able to, entrance behind the gender curtain opened for me like never before.

It took many times behind the curtain for my innocence to really go away. I needed to battle my paranoia with being shy to start with and then having to communicate on a whole different level before I could relax at the girl’s night’s out I was suddenly being invited to comfortably. And that was not the only one thing I needed to deal with. Such as how I would ever dress to blend with the rest of the ciswomen in the group I was invited to. I certainly did not want to embarrass myself by dressing too much or not enough and finding that special point where I blended right in. My innocence was real, since I was dealing with a world I had never been in before, but the pressure was real because I wanted to make it a success so desperately. I can compare the experience to first dates I went on with women I did not know well as a man. How would I start the conversation and what would I say.

It turned out I did not have to worry that much because the group conversation was easy to follow without men around. It flowed around family basically and the relationships the women were having with their men. I just flip-flopped my past life as a man to one of a woman. Being purposely vague about key issues such as not having the birth of my daughter but I was there when it happened. My communication efforts seemed to work with all but one woman who just glared at me. I ignored her glare and stayed in the conversation and got invited back.

As I experienced more of the world as a trans woman, the more my innocence went away. Sure, I encountered the occasional toxic woman or TERF but with my confidence level soaring I was able to handle most all of them. If you are wondering why I have not mentioned any men, it is because there were so few of them. For the most part, they knew I had left the men’s club and wanted nothing to do with me, Plus, I cannot take all the credit for my success I had a very tight knit group of women friends around me to support me too.

Perhaps the most lesson I learned about gender innocence was the amount of difference there is between the two main primary genders. Basically, I learned that men operate on some sort of a power matrix. When they are challenged, they are less likely to give you a chance unless there is something in it for them. Women, on the other hand, are much more open to the world. Especially when it comes to their sexuality, which is not as frail as a man’s.

As I always say, if you are just starting up your gender path, be prepared for a change in your innocence as you enter the world of your preferred gender. And thank you for reading along as I described mine.

 

 

Thursday, September 10, 2026

Just Another Lonely Day

Image from Jarge Johansen
on UnSplash.
Throughout most of my life, I was desperately lonely, as I had no one to fall back on as I explored my gender issues.

Growing up in a rural area, I started with just a
small circle of kids I interacted with and it rarely grew significantly, so again I was stuck with why I felt the way I did about myself. All I knew was I had a difficult time interacting with the boys at all and the girls seemed as if they were some unreachable magical creatures I knew nothing about.  While all of this was happening, all I could do was carve out my own little world where I was a pretty girl in front of the mirror in mom’s clothes and makeup.

Little did I know how those humble cross-dressing beginnings would come back to influence my life later. In fact, forever. As I grew, I became more skilled in using makeup and finding clothes which I could fit into when I outgrew moms. Then, the more I cross-dressed, the more I wanted to. Which did nothing for my extreme loneliness. It seemed to me; I would never find a way out and really did not until I hit my late high school and college days. What happened was, a group of girls at high school learned that a friend of theirs did not have a date to the junior prom and I did not either and matched us up for the evening. After a successful date, I was not so lonely when another friend of mine set me up with a single girl he knew and suddenly, I was a socialite as I entered college. In truth, deep down I was still the deeply conflicted person I always had been.

Amazingly, my early college years were so intense that I forgot about my gender issues for six months or so before they crept back in. When they did, they became as intense as they were before I left for college and stayed that way until they were put on my back burner when the military draft caught up to me when I graduated. For a while I was engaged to a woman I knew from college until she left me just before I was due to report to Ft. Knox for Army basic training leaving me completely alone again. When my fellow soldiers were getting mail from wives and girlfriends, I was getting an occasional letter from mom. At the least, I appreciated her efforts and once again I was back to being used to being intensely alone.

All along I wondered what my military time would do to my gender issues. Would they go away temporarily like they did in college or not was my question. The answer I was looking for did not take long to become evident to me. No my gender dysphoria was not going away and in fact, tools I had learned in the Army just made my dysphoria stronger. For example, I became more confident in myself as I had a better idea of what I could survive and I spent hours of what spare time I had daydreaming of what I would do with my feminine self once I had served my three years.

It was not very long after I was discharged that I gathered the courage to ask my first wife to marry me. Since she was in the Army too with me for over a year, she had witnessed my Halloween party costume at a hospital party we had went to with friends. Plus, my later confession to three friends plus her that I was actually a transvestite and my costume went a lot deeper than it looked. She also turned out later be the mother of my first and only child and the marriage did last several years until I fell madly in love with my second wife.

Oddly enough it was another Halloween party which allowed me to confess to her my deep dark secret that I was a cross-dresser. It turned out that she did not care which was the case for the twenty-five years we were married. Until I began to transition into a transgender woman. Just before she passed away from a massive heart attack. During those years we had our share of good times and bad times somehow, we always made it through, and she never knew how much of a role model she was to me when I went my separate way as a trans woman. Following her untimely death at the age of fifty.

When she passed, I went into a lonely shock I had not felt through the majority of my life. I could not understand why I was having to start all over again in my mid-fifties and search for another relationship. And furthermore, which direction would I take with the gender issues I had during my life. By this time, I was well ahead of my goal to possibly live as a transfeminine person. I had major decisions to make in my life, so I kept on searching for answers. To start with, I tried dating ciswomen again as a man which failed miserably and at the same time, get more serious in my explorations ss a trans woman which I found to be a natural social release for me.

By the time a couple more years of wasting valuable time went by, I was sitting by myself enjoying my new company and I thought why was I not living like this all the time? How stupid could I be not to take advantage of what I had learned in the world so far as a transgender woman. Most importantly, my lifetime’s dream of living as a woman was within reach, and I was not taking advantage of it.

From that point forward I put together a timetable to give away my remaining male clothes and pursue HRT therapy. There would be no turning back from that point forward. I was tired of the gender struggle and loneliness I was enduring. I was afraid if I did not make the change now, I never would have the chance.

You might say I played the odds and they came out in my favor but on the other hand, I researched the odds extensively before I did it.

 

 

 

Is It too Early for Halloween?

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