As the Clock Strikes Midnight

 

JJ Hart

New Year’s Eve is upon us again.

With it comes a flood of memories, some good, some not so good from both sides of my transgender border. First, let’s remember one of the ugly male experiences I had. This came from years ago when I had completed my tour of military duty and we were celebrating that as well as the New Years.

Being the huge drinker that I was, I ordered a keg of beer and a bottle of mezcal for a smallish party my second wife (to be) and I were having. Too much booze it seemed to stay socialized at all. To make a long story short, after a hard night of trying to drink the mezcal and the barrel of beer, when the clock struck zero and the ball in Times Square dropped, I did not kiss my future wife first, I committed the ultimate sin of kissing her more attractive sister. Needless to say, there was no way to hide what I did, and I was in deep trouble no matter what I had to say about it.  The damage was done, and I would have to live with it for years. In fact, I don’t think I ever lived it down.

I could blame the entire unfortunate episode on toxic masculinity setting in, but in fact, I was trying desperately to bury any thoughts that I had of being a woman on yet another New Year’s Eve. From then on, the yearly debacle which was a party on New Years went on by me in a blur. At the least I proved I could outdrink anyone else and at its best I learned the problems of acting like a fool and being careful to kiss the right person at the right time.

Nothing really changed until I met my current wife Liz approximately seven years ago when we went out on the town in downtown Cincinnati for a New Year’s Eve celebration. We began with having an Uber ride to our first destination, which was the Cincinnati Music Hall for a performance of the symphony orchestra. Even though I thought I was dressed appropriately for the occasion in my black sequined gown, I was still very terrified about going at all. It turned out that once again all the worrying in the world did not help me at all because nothing happened. I went, I blended and I conquered all those around me who may have questioned having a transgender woman in their midst. And probably, the best part was that the night was just beginning.

From the music hall, we took a terrifying taxi ride in a cab company called Einstein Taxi (really). He drove us at breakneck speed to a venue where we had dinner reservations down by the riverfront. Once we safely arrived, we did not have to wait long to be seated and once again I was met with no resistance to being me at all. The venue was also a micro-brewery which featured German food, so we ate well as we waited for the ball to drop on a New Year. This time, I made sure I was kissing the right woman. Liz of course, before it was time to head back home and no, we did not drive.

This marked the first time I can remember I did not have the thoughts of failure hanging over my head. I was not going to spend another year as my hated male self again. What a relief!

This New Year’s we have a huge college football game to watch as The Ohio State Buckeyes play Miami of Florida. Since the game does not start until seven thirty, we will have plenty of time to open a bottle of wine and toast the incoming 2026. Without dwelling on all of the problems the transgender community had heaped on us in 2025, maybe the upcoming year will be the one when the rest of the world says enough is enough and the upcoming mid term elections will sweep the evilness and the liars out. It is the country’s two hundred fiftieth anniversary. It is time to reclaim some of our past which made us great.

That is my hope for the New Year, as well as I hope you have a better year too, no matter what your goals and dreams might be. I will be spending it in the comfort of my own home with my favorite person who did more for my male to female gender transition than anyone else. It does not get any better for me and I don’t have to worry about who I am going to kiss.

Happy New Year’s!

You're so Vain

 

Image from Ava Sol
on UnSplash

Expressing yourself to the world as a transgender woman carries with it a certain amount of vanity.

Until you begin to relax in your new feminine world, I think you need to obsess over every detail of your exterior appearance. Since we all have such a vast amount of catching up to do to compete with other ciswomen in the world, details matter. Perhaps one of the first lessons you learn is how competitive the world is when you are a trans woman. Ciswomen are every bit as competitive as men but in certain areas not readily visible to the male gender.

For example, the major question comes to mind that do women dress for men or for each other. Sadly, we never had the input of mothers, sisters or girlfriends saying, “are you wearing that?” I know if I had that sort of input, it would have saved me a lot of embarrassment when I first began to go out into the public’s eye. It was a resounding yes for me when I learned who women really dress for…themselves. My problem was, my male self-kept getting in the way and had me dressing like a trashy teen girl. All poorly concealed in a testosterone poisoned male body. It was no wonder I was creating negative attention and getting laughed at. When all I was doing was trying to present myself well the best way I knew how.

After I began to learn and change my thought patterns concerning fashion and makeup, I began to have success in the world. So much so, that on occasion (when I was so vain and did everything right) I received a compliment or two from a cisgender woman. One thing was for sure; it takes a woman to know the work it takes to perfect a public image with makeup and fashion. Plus, I needed to be better than the average woman because I was working at the whole image after I started as a man.

It turned out, having to be better in the world worked well with my increasing source of transfeminine vanity. All I thought of was how much better I could look if I tried just the right foundation and mascara, as I haunted the many thrift stores, I went to looking for just the right piece of clothing to add to my wardrobe of feminine clothes. My personal newfound male to female femininization vanity was in full force as I was having fun. In reality, I saw nothing wrong with being vain in how I appeared as my authentic self, until I clashed with my second wife.

She rarely wore makeup or dresses at all and did not like the way I presented myself at all. On the rare occasions we went out together as women, I tried to tone down the amount of makeup I was wearing along with putting on my most conservative clothes. All because I wanted her approval, which I never got. If I wore any less makeup, I might as well say to hell with it and go out with her as my old male self. I was stuck between the rock and the hard place as far as my feminine vanity was concerned.

As I progressed with my makeup and fashion experience, I understood how much work I would have to put out to achieve the transgender goals I wanted. I knew I would never be able to transform my old male self into the prettiest girl in the room but on the other hand I could present well enough to get by. Everything that I was doing at that point just became a blur of change. Especially when I was approved for gender affirming hormones or HRT. As my skin softened, hair and breasts grew, it all was a welcome addition to all the work I had done all those years to just survive in the world. As I wrote yesterday, just not having to wear a wig anymore was a huge deal for me since I had no male pattern baldness to contend with. All of a sudden, I needed to contend with a new form of vanity when I went to beauty parlors to have my hair done just a certain way.

During all the years it took me to fully come out into the world as a trans woman. I learned the true meaning of competing with ciswomen in the appearance arena. Once I did. I needed to move ahead to the larger context of being allowed to exist in women only spaces by the alpha-female gatekeepers. In many ways, my second wife was an alpha female who never let me in, so I wonder what would have happened if she had lived long enough to see/know the person I am today. One thing is for sure; I am no longer the “pretty, pretty princess” she used to call me because I have paid my dues as a transgender woman.

All I know is I did go through my periods of extreme selfishness and vanity to arrive where I am today and I don’t know if there is any other way to go down the path, I ended up taking. Changing a gender is such an intense way to live, especially when you started with so much success as a male that it took me a massive effort to change. Not to say, all of the effort was not enjoyable but at least, it was interesting and challenging to see behind the gender curtain.

For many of us stuck in our own form of gender dysphoria, vanity is just one aspect of our larger need to survive.

 

 

 

Dark Side of the Gender Moon

 

Image from Maria Kovalets
on UnSplash.

Exploring the dark side of the gender moon for me meant a lot of work.

I equate it to the first times I could experience wearing my own hair in public without the help of a wig of any sort. The satisfying part was that I did not have to worry about the style and color of the wig I selected and how hot it was going to be on my head during the warm summer months when my makeup threatened to melt off of me as soon as I put it on. On the other hand, I needed to master the art of looking at the back of my head in a mirror to see how my new hair looked. I began to think of it as the dark side of the moon. No longer would I have the ease of styling a wig on a wig stand in the back so I knew it would look good on my head.  

Also, not wearing wigs anymore opened up a new wonderful world for me of visiting women’s beauty salons. I will forever remember the first time my daughter gifted me a visit to her upscale salon/spa. I was just coming out of my gender shell and the whole prospect of having my hair done terrified me, but I hitched up my big girl panties and said yes. Little did I know what was instore for me. Thanks to my daughter, first of all I needed to walk through seemingly an endless gauntlet of women in chairs in various stages of having their hair done. I gathered up all of my courage and tried to walk as femininely as I could until I met my new stylist.

The first of many decisions I needed to make was what color I wanted my new hair to be. As my daughter and stylist hovered over me with what seemed like an endless set of examples to choose from, I chose a red/blond streaked shade and then had to pick how long or short I wanted my new hairstyle to be. I had no idea choosing the dark side of my gender moon would be this difficult. Quickly though, I chose an off the shoulder look which maintained most of the hair I had grown. All too soon, my appointment was over and I was spun around in the chair to see the new me and I loved her! All the years of frustration of not being able to afford quality wigs or take care of them faded away and the best part was I had been blessed with visits to women’s spaces such as beauty salons and I walked away from the experience knowing why so many ciswomen value their beauty visits to the hair salon the way they do. The day following my first visit to a serious upscale salon, I thought I had been exposed to so much estrogen, I could skip my daily dosage.

I guess you could say, having my hair done was just the first of dark side of the moon gender moments in my transfeminine life. When you add in all my other journeys into women only spaces, there were plenty of other experiences to mention. Like the one I rarely recall when I was invited to go out and party with a few of the servers, I met at one of the regular sports bars I hung out at. Like the experiences of having my hair done, I had been out several times on girls’ nights out invitations in my past, but never like this one. These women were all much younger and prettier than I was so I wondered how I would fit in. The answer was that even though they were all nice to me, I did not really fit in at all. The other women were too busy getting hit on by guys so there was little time for other socializing. I quietly sipped my drinks and pleasantly left with the group when most of them did. More lessons learned.

As far as any major male to female feminization process goes, there are inherent risks to be taken when you go through the process of losing your male privileges and discovering your new feminine ones. I know in my case, I was starting to know I was successful as a transgender woman when I began to be treated in certain ways. Such as when men in particular began to question my intelligence as I talked to them. I thought to myself, did I treat women this way?  I was definitely on the dark side of my gender moon as I explored a new world.

As you begin to explore your new world, there is plenty to do such as gathering the courage to use the women’s rest room. Which is a natural need when you are out and about for any length of time as your new trans woman self. Not any of the rightwing paranoia being spewed by the bigots saying we are men using the women’s room.

Actually, exploring the dark side of your gender moon can be an exciting experience and one you have waited your whole life to take. Take it far past just styling your own hair and/or wig and expand it all the way to discovering a new world you wanted to live in so badly. Just try to enjoy the discoveries you make and any aha moments you live through. There is so much to be learned when you jump the binary gender border to live on the other side. All the work I put in was certainly worth it.

 

 

 

 

 

 

 

Fearing Change as a Gender Challenged Woman

Image from Joshua Gaunt 
on UnSplash. 

Gender change came so very slowly for me during my life.

First, I needed to free myself from the male bonds I was born into which I had no control over. Looking back, I think one of the main problems I had was fearing the changes I was looking to go through if I faced up to reality. From that point forward, life became a struggle as I feared changing it.

What I became was the best transgender procrastinator I knew. Any excuse I could come up with not to go through with living my dream, I clung to like a survivor on the Titanic. What I would do about spouses, family and employment were a few of the major questions I was asking. So, what did I do? I ran as hard and as fast as I could from the problem. I was running so hard, I even changed jobs very quickly so I would not be bored with my life as a transfeminine fugitive. Eventually, even though I grew tired of the pace, I found a stable good job and settled part of my life down. I say part of my life because during that time my gender issues were raging out of control.

Even though I was slowly becoming successful at blending my feminine self in with the world of cisgender women, I still had many fears to conquer. Just when I thought life was improving for me, I would hit another roadblock and send me running back to my cross-dressing drawing board. Which was crazily marked with clownish makeup until I got it right. The fear of applying skilled makeup kept me occupied for years it seemed. On the other hand, when I got my male ego out of the way and realized I needed to dress for other women and not men, did I begin to improve my overall look and the laughter I used to receive in public began to die away. When it did, I learned the most powerful force I had to combat gender change was having confidence in myself. Surely, I would never be the prettiest most beautiful woman in the room, but a lot of other cisgender women were not either and they were surviving and even thriving just fine. There were many layers to building womanhood and I just needed to find mine.

For some reason, the more success I felt as a transgender woman, the more fear I had. I guess it was because of my old male self-starting to panic because he was losing his dominance over my life. For years, what had seemed like the impossible gender dream was now looking as if it could become a reality. As he fought his new reality, the stakes towards living a successful life as a trans woman, increased dramatically. Every step I was taking towards my dream seemed to feel as if I was walking in quicksand since at any time, life as I knew it could be disrupted beyond repair in the little backwards town I lived in. I still lived in mortal fear that any day I could be discovered and the acquaintances I had built up over the years would realize I was living a gender lie. Which I was.

I finally made it to a point where I could not procrastinate my life any longer and I began to use every spare moment to explore the world as a transfeminine person. It all meant I accepted the challenge to finally go all in with making the final preparations for my new life. The bittersweet part of it all was part of my male to female final transition was built on tragedy. In the space of a couple short years, I lost my second wife as well as all of the friends I had built up over the years to death, and I had to start all over again. Sure, I was still afraid to do it but deep down I knew transition was the only way I could go. Suddenly it was up to only me to decide if I wanted to take the ultimate step and try to get a doctor’s permission to begin HRT or gender affirming hormones. I was approved and then the changes I was hoping for began to really happen for me. The changes were so dramatic, I sometimes take an entire blog post to relate them to you.

What frustrates me now are the haters who say that because I took so long to transition, I am not trans enough for them. Normally, they are younger LGBTQ individuals who have no idea of what the world was like way back when I was growing up. We all have our own gender crosses to bear, and we need to understand each other’s journey.

Sadly, there are all those transgender women and trans men who can’t take the burden of gender change fear any longer and tragically try to take the self-harm way out. The suicide rate in our community is completely too high and could come down with proper help and understanding.

In my case, my excuse is I had a heavy dose of ignorance combined with fear and procrastination as reasons it took me nearly a half a century to come out of my gender shell and live freely in the world as a transgender woman. These days, if you can steer clear of all the online trolls and haters, you can still get valuable information on the internet concerning ideas on how to build a new life as a woman from scratch. Plus, fear for me was a powerful motivator and when I was forced into a corner because of my gender, I came out fighting because I believed I was right.

It turned out I was.

 

 

 

  

Resolutions

 

Image from Nik on UnSplash.

I am a firm believer that most new year’s resolutions are made to be broken. Statistics say that nearly eighty percent of people never keep resolutions.

On the other hand, in my formative transgender years, I ended up making several resolutions that I intended on keeping. But by now you might be able to guess which ones I am talking about. The further I was going towards being able to live the feminine life I always dreamed of, the easier it was for me to set new resolutions to conquer in the upcoming year ahead.

Very early in my gender journey, it was easy to set easier goals such as getting out of my dark closet and into the world. I figured from there I could look around and see what was next. What was next proved to be terrifying, natural and exciting all at the same time. More and more I felt bored by the old idea that all I wanted was a chance to be a woman on my own terms. It got to the point where I did not have to make any resolutions which I would have to break. I was doing a good job at living out the ones I had already made. Ironically, I missed several resolutions I should have made but did not. Such as when I did not see my second big gender transition coming at all. It was when I shifted gears mentally and began to think of myself as being transgender and not a cross dresser at all. To this day, I have nothing against all cross dressers (since I was one for years) but my gender needs took me deeper.

Of course, going deeper into my transgender rabbit hole, brought out the need for new resolutions. The old shallow ones such as could I exist in a ciswoman dominated world no longer were making it. I was way past all of that and needed to find out once and for all if I could carve out a new life for myself that I had only dreamed of. You might say, reality of life began to outstrip my dreams as well as the need for more resolutions. At that point, I quit making them all together.

It was easier to go free form in my transfeminine pursuits and do the best I could. It turned out that for the most part I was successful and continued on feeling good about myself. Until the usual problems arose with my unapproving wife and a male self who continued to dominate a big portion of my everyday existence. As I thought more and more about them, I wondered what I would ever do about setting up more resolutions about changing my life for good and jumping the male to female femininization border.

I don’t think until you have walked a mile in our high heeled shoes as a transgender woman would you understand the relative importance of making new year’s resolutions. While others are thinking about losing weight or cutting back on their drinking, you (on the other hand) are wondering what in the world are you ever going to do about becoming a full-fledged transgender woman. It is especially difficult when someone you know asks you what your resolutions are and you don’t want to lie.

At that point, I just went back to my default position I used when anyone asked me about my future. When I was a kid, instead of saying one day I wanted to be a woman, to please my parents I just said I wanted to be a lawyer or doctor. Seemingly, nothing changed later in life when I was asked about my resolutions, I would just say to lose more weight or make more money. So, I lied and took the easy way out. There was one way I could tell the world the truth at that point in my life. Then I started to wonder how many other people who spoke of their resolutions on new year were fudging their answers too. All those people who rushed out to join a gym never really meaning to go like I did once. As I think about it, going to workout in any shape or form was yet another gender smokescreen I threw up to disrupt anyone who was sensing my transgender issues.

Overall, I wonder how many other trans women or trans men have had to try the same method and any sort of a public call for a resolution or two is just another way to hide while you are on your path. One of the statistics which I have read on resolutions said that only twenty percent of people making resolutions keep them anyway, so I don’t feel so bad about not making them anymore. And who knows how many of those making resolutions are closeted transgender people anyway?

Looking back, the only advice I could give to a trans person still in the closet thinking about the new years and making resolutions is to try to make yours doable and don’t try for too much. Failure only leads to disappointment and a deeper return to your closet.

Anyway, you cut it, a new year is on the way, and we have a chance to sweep away a very disappointing 2025 out the door. Just keep your head high and hope for the best in 2026. At the least we will have a chance to vote and change a very crooked regime in Washington. Something you can do from the privacy of your closet, and no one will have to know and if you do make resolutions and don’t keep them you will be in the majority of the population for a change. A real rarity.

 

 

 

 

Alone in a Crowded Room

 

Image from Bruno Aquirre 
on UnSplash.

I often refer to the days when I was first going out and seeking clues to my true identity as going out to be alone. I called it that because I had not yet met any regular acquaintances that I would have called friends on a regular basis. So, I was surrounded by a group of strangers no matter where I went. Even so, it was better than sitting at home by myself staring wishfully into the mirror.

Following leaving my painfully shy days behind me and becoming a rather social person, I did miss the interaction with the public. Going out alone was the only recourse I had which brought up several other problems. One of which was if I did present as a successful woman sitting by herself at a busy bar, always invited trouble because I was so out of place. It was during those times that I used my cell phone as a prop. In essence signaling to people, I was waiting for someone to arrive and join me. Plus, in the cold winter months, I could place my coat or jacket on the seat next to me to act like it was occupied. Both of which helped keep away any unwanted advances from mainly intoxicated men. On the other hand, other intoxicated ciswomen did not count, and I welcomed any of their advances which completely outnumbered men. Mainly because the women were so curious about what I was doing in their world.

Another problem I had was a huge case of impostor syndrome I suffered from. No matter how nice the stranger approaching me was, somehow, I felt I did not quite belong in the new exciting world I was in. It took me a while to get adjusted to the fact I was succeeding in a life that I had previously only considered a dream. I also still considered myself a rank amateur because of how I was able to conduct myself as a new transgender woman. I knew very little about how ciswomen communicated in the world away from men and it showed. For the longest time, the little nuances women use to communicate escaped me. Forcing me into shutting down and just listening to others and sometimes coming off as a standoffish bitch. Which was the last thing on my mind to happen.

I began to move away from being a stranger in a crowded room when I began to have enough confidence in myself to move forward. I was no longer just an virtual impostor just observing the world to jump in and inserting how I felt about things and people around me. A word of warning though, it took me a while to get there. Too much trial and error before I gained the confidence in my own unique form of womanhood which differed from many other women around me but at the same time, was still as complete. Sort of.

It was not until I began to build up my own circle of friends who happened to be mainly lesbians did, I began to relax and truly enjoy myself. I was no longer an imposter but now a full-fledged participant in my resurgent social life. Probably the only mistake I made was when I did not realize how different two of my friends were who I kept inviting to our impromptu meetings at sports bars and lesbian mixers. I was still naïve to the lesbian culture and did not realize the differences between a so-called gold star lesbian and one that had been with a man. I had one gold star friend along with another who had been previously married with three kids, so on occasion sparks did fly. In the meantime, I was off in my own little world jumping at the chance to be a wing person for one of my friends and trying to set her up with another woman at the mixer. It never worked, but I had a fun time trying.

The best part was I was no longer a stranger in a crowded room. I was becoming a full-fledged participant and loved it. The only problem I was having then was my new feminine life was starting to seriously force my hard-earned male life into an early retirement. A retirement he was so not ready for. Often the gender conflict I endured was mental and brutal. I did the only thing I knew to do and that was to internalize my feelings and move on. Which was the last thing I should have tried to do. My male self-wanted to keep me being a stranger in a crowded room so he could have his way. What he did not count on was, the more I worked on my dream gender life, the bigger and more accepting the room became.

The more I think about it, the more I think my male self-wanted to keep my female self as a kept woman. Validated by him only. Eventually, my transfeminine soul won out and he needed to face the truth. He was always part of living a lie in my life. Since my impostor syndrome was for the most part gone, it was the last remaining significant part of my life for him to cling to.

It felt so good to no longer just to be going out to be alone and know I would have the chance to meet my friends or even make new ones. Because I had hid my true self away for all those years, my transgender dream self could not wait for a chance to live and express herself in a crowded room.

 

 

Happy Holidays!

 

Ralphie!

Happy Holidays to you and yours!

I hope those of you who have experienced close family losses because you came out to them as transgender are able to rebuild close ties with other non-blood more accepting people. They are out there and it sometimes takes a while to rebuild trust with other people with your feelings I know. Sometimes, you can find connections within your local LGBTQ organizations. I know, around here where I live that is the case when organizations host potlucks as well as Christmas parties for anyone who wants to come and be around others.

Also, as we are preparing to put 2025 behind us, we look to the holidays to provide hope for the future. 2026 will be a huge election year for example. It seems we are building a chance to put the political tragedies heaped upon us by a rotten president leading an equally rotten, spineless political party which has used the transgender community for everything evil in our country. It will take all of us, pulling together, to make a difference which is part of the holiday spirit. That is why I urge even the most closeted cross dresser to look out of their closet to a future of freedoms they may need later in life.

Happy Holidays to me also means thanking all of you who took the time to wish me the best this time of the year.

On Christmas Day, I will be binge watching “A Christmas Story” which hits so close to home for me. Other than the time period which it is filmed in which roughly matches my life, there is the story of “Ralphie” and his BB Gun. If you have never seen the movie, Ralphie is the child star of the show who desperately wants a BB Gun for Christmas. And the movie goes through all the trials and tribulations he goes through to receive one as a gift. Just when all seemed lost, and all the gifts were opened and Ralphie was dejected, when his father pulls out a brand-new Daisy BB Gun he had been hiding and then the fun began.

My major point to all of this is, I had a major role reversal with Ralphie and the BB Gun. You see, I never wanted a gun of any sort for Christmas and would much have wanted a nice doll baby or a new pretty dress. But there I was once again stuck in a male world I wanted nothing to do with.  That is why I am so enamored with “A Christmas Story” which goes right up there with the National Lampoon’s holiday classic with Chevy Chase as one of my favorites.

I know I am so fortunate to be spending my Christmas with my wife Liz who scooped me up off the trash heap of life I was on at the time when we met online over a decade ago. She was kind enough to accept some of my off-the-wall holiday traditions as well as me accepting hers. I guess that is the basis of a good relationship but one which worked out so well for me. Hopefully, you will find yourself in the same situation or will be in the upcoming year. It happened to me when I least expected it. 

In the meantime, here is wishing you and yours a safe and festive holiday season and don’t drink all of the high-powered eggnog which I used to do! Save some for someone else…It is Christmas!

 

 

 

Acceptance...all that And More

 

JJ Hart.

Just a short post this morning since I was out and about with my wife Liz to medical appointments and more.

This morning, I got up early to go with my wife Liz to her doctor’s office appointment. Per norm, I did not expect much interaction with the public since we were going at such an early hour. So, I could keep my feminine prep to a minimum.

I kept my prep to a close shave and brushed my hair along with leggings and sweatshirt top and I was ready to go. With my rain boots along with the wrap my daughter got me for my birthday to keep the cold wet away. As Liz went to the receptionist at the hospital to be checked in, I grabbed a nearby seat to sit and wait, and the receptionist very much ignored me one way or another. I was off to a good start as all of the other people who followed us into the large waiting room were off in their own world and ignored me also.

As I was playing on my phone as I waited for Liz, I began to think about how far that I have come over the years when it comes to being accepted as me, as my true self. I used to obsess on my appearance when I went out and about at all, until I noticed I was the only woman doing it. Gender acceptance was as important to me then but was still somehow different. These days, my acceptance level seems to be at an all time high which is great for my continued confidence as a transgender woman.  I will certainly need all that I can get when Liz and I take off again for another extended vacation south from Ohio in the latter part of January. As always, my paranoia stems from using the women’s room in the states we travel through which frown on it.

Through it all, I keep telling myself this is the fourth or fifth tour we have been on, and I have never had any restroom problems, so why start now.

Other than that, we don’t have much going on except I have a mammogram in February.  It is hard to believe the winter will have moved on so quickly from me. Especially at my age, it is sad to see life moving by so fast. 

Back to the present, to reward Liz for getting her flu and pneumonia shots, we went through our favorite coffee shop, drive through for warm coffee drinks and a light breakfast sandwich and the girl at the drive through window said, “you girls have a nice day.”  With that comment, she made sure I did.

No matter how long I live my dream of being a transfeminine person, reinforcement from a stranger is always great acceptance and more.

 

 

 

The Hustle and Bustle of Christmas as a Transgender Woman

 

Image from Clarke Sanders
on UnSplash.

Doing the Christmas shopping shuffle as a transgender woman, often takes a lot of courage and confidence to do it.

Over the past couple of weeks, I have written about my holiday adventures leading up to the big day. From taking a short trip to Clifton Mill to view their extensive, festive lighting display all the way to letting two men load my heavy purchase for me at an Oak furniture store, I stretched the boundaries of what I was used to as a new cross dresser or trans woman in public. After it was all said and done, even though I was terrified most of the time, I was happy I tried it all. I came out of doing the Christmas shuffle with much more confidence in my girl self than I had going into the season.

In fact, as I have written before, Christmas quickly outpaced Halloween as my favorite holiday. Why? There were several factors, such as the length of the season and the creativity I could put into celebrating it. Plus, for once, I was doing good for others by buying gifts for them as I shopped. I positively loved it and wondered where the experience had been most of my life.

If you are a procrastinator and last-minute gift shopper like I was, doing the Christmas shuffle as a transgender woman is ideal for you. As you can get lost in the crowds quite easily and no one pays attention to a single woman out doing her late shopping. Custom made for you to do your shuffle and head back home.

I was fortunate when my second wife left her bookkeeping job and took a managerial position at a large bookstore chain. So, at Christmas, she was very busy and worked many hours. It was easy for me to schedule my hours around hers, so I had plenty of time to get out of the house and do gift shopping. I could obsess on wearing just the right outfit to blend in with a busy world and at the same time, search for just the right gift. Along the way also, I could stop in and grab a bite to eat at a restaurant and again stretch my ability to deal one on one with the world as a transfeminine person. Yet another reason, I came to prefer Christmas over Halloween because I hoped I was not perceived as a man wearing a costume, or worse yet some sort of drag queen.

As the big day approached, the sky was the limit for me. I did my shuffle as much as finances allowed and stockpiled my gifts for my special night where I stayed home with some high-powered eggnog and wrapped my treasures to go under the tree if they would fit. Of course, my wife was close to being a professional gift wrapper and I was just the opposite. But as the eggnog kicked in, I did not care, and besides it was the thought that counted. Right?

Finally, the big day arrived and I was shuffled out. Plus, we had family connections to visit all day on Christmas day. My thoughts for once were in other places than doing my precious shuffle which I had learned so much from. After the day wound down and my wife and I were alone, we opened the final gifts from each other. Which included a gift for my feminine self. I will forever remember a nice fancy fuzzy baby blue sweater she gifted me. It was snug fitting and I filled it out nicely with my new silicone breast forms I received from a cross-dresser acquaintance of mine who was purging. Naturally, that part of our gift giving day was the part of the day which was the most anticipated for me. I was like a little kid, brimming with anticipation.

Every year after the intense transgender Christmas shuffle was over, I had the chance to sit back and reflect on all my experiences and what they meant. Without hesitation, I think the confidence I built up from going out in the world as my trans self was the most important aspect of what happened to me. I learned what it meant to blend in with ciswomen around me and survive better than I ever could before. I also discovered the vast majority of the world did not and does not care about having a transgender person in their midst. The biggest difference is that back then, we did not have a Russian asset in the White House leading his blind, spineless party into demonizing a small portion of the population. Back then, I was merely a curiosity to many people, especially ciswomen.

When my second wife passed away, the need to do the major Christmas shuffle went with her too. The only blood family I had left was a brother and a daughter to worry about at all during the holidays. When I came out to them, I was roundly rejected by my brother and completely accepted by my daughter and her family. So, I broke even and even did better when I considered the relationship, I was able to build up with my daughter, son-in-law and three grandchildren. I won the family coming out shuffle in a big way.

Even still, sometimes I miss the hustle and bustle of doing the transgender Christmas shuffle as over the years, I have gone nearly the entire direction in the other way. It is hard to say what I miss most but it probably having the financial resources to buy basically as many gifts as I could afford might be it.  Maybe it all came from having a guilty conscience from sneaking out of our house to join the world as my authentic true self instead of my old boring male self and breaking the pledge, I gave my wife that I never would.

Whatever the case, I was extremely selfish and was a contradiction when I did it to buy gifts for others. I guess it fit in with the whole contradiction I felt from my deep-set gender dysphoria to begin with. I dealt with it all the best I could, did my Christmas gender shuffle and moved on with my life making the most of it.

 

 

Earning my Way into the Sandbox of Women

 

Image from Juli
Kosalapova on
UnSplash.

I call being accepted in the feminine world of ciswomen around me, as being able to play in their sandbox.

Getting a chance was similar to living a dream and very difficult for me to do. To begin with, I needed to lose whatever weight I could off of my very male dominate frame and take better care of my skin, so I could use less makeup. I desperately wanted to be pretty but accomplished it as naturally as I could. Motivation to do both came easily for me because I was obsessed with doing something very well in life that I cared so deeply about. Surprising even myself, I was able to shed nearly fifty pounds as well start moisturizing daily after I shaved. Obviously, the weight loss helped more dramatically when I could shop for a better selection of stylish women’s clothes in my new size and the decrease in makeup I needed spoke for itself when I presented better in the world.

Even with those positive results behind me, I was still very naïve and had very little knowledge of what I would have to do to be let in to play in the sandbox by the alpha female gatekeepers. As my second wife was always fond of telling me after major fights, we had that I made a terrible woman. Then she added she was not talking about appearance. Which was good since I had just had situations where I was mistaken for a ciswoman to back me up. Then I was confused, if it was not my feminine appearance holding me back, what was it? What would make me a better woman after all.

From that point on, I set out on a mission to understand what she was telling me but I had a major drawback…I was still living the vast majority of my life as a man and as such, ciswomen would not allow me back behind the gender curtain. For the most part, I was stuck in my part-time cross-dressing ways until I could find a better way out. The sandbox remained a faraway dream.

The main problem remained. My male ego would not easily let me pull down my male defenses to see and learn what really went on in a women’s world which operated quite nicely with or without male influence. For the longest time, he (me) refused to listen to women the best he could to learn what they were really saying when he was stuck playing the game behind the gender border. I felt as if I was in East-Germany behind the Berlin wall of gender. I knew I wanted to escape but did not have the willpower to do it. I was a victim to my newly discovered transgender hopes and dreams. At that point, I still had not realized how far behind my gender dreams being a victim made me and I still felt sorry for myself because of all my gender dysphoric issues.

As I always point out, it was not until I began to experience my version of womanhood in the public’s eye did anything begin to change for me. All the effort I put into my appearance came back to help me get my high heeled foot in the door with other women. Then the real work began when I needed to communicate and interact with them. What happened was many other ciswomen were encountering me on a regular basis in the venues where I always went, so I needed to develop a stable feminine persona to go with my appearance. What would I call myself and what wigs would I wear every time I went out are prime examples of what I am talking about. I was getting to the point where I was staring my forties in the eye and I knew I was not getting any younger and in the back of my mind, I had a sneaking suspicion that I had lived my life all wrong up to this point.

Rather than bemoan all of the mistakes or missed opportunities I had as a male, I needed to face the fact I was wasting my time as a male anyhow because I was always meant to be female. I went home and wrote in my secret diary that I was not a man cross dressing as a woman; I was a woman doing her best to cross dress as a man and build a life on a house of cards.

The realization of my true gender status enabled me to be my real self to the public and ciswomen responded well to my truthful gender identity. Even if they were curious what I was doing in their world and why I wanted to play in their sandbox and work my way into coveted woman only spaces. Finally, I was coming to the point where I could think I achieved my own womanhood, just in a different way than most ciswomen. I was still relevant to the world and should be allowed to play in the sandbox.

Another big lesson I learned was that once I was in the sandbox, I needed to work harder to stay. One slip up back to my old male self, and I would be labeled an impostor and barred from the box. Faced with the task of starting all over again. To the best of my ability, all of my feminine mannerisms, interactions and vocalizations had to be perfect. I was so afraid most of the time until I finally began to relax and have confidence in myself.

The best part about the entire process was I survived to write about it and hopefully to inspire others in this very trying, difficult time to be a transgender woman to make it also. We all have differing yet similar paths to make it to the women’s sandbox. Just don’t expect the process to be all positive and you can make it by hopefully finding ciswomen who knowingly or unknowingly help you along. Those minor claw marks you might receive like I did down my back were just learning marks and helped me along. More than the women scratching me ever knew.

They helped me to earn my way into playing in the women’s sandbox. The claw marks just equated out to the stripes I earned when I was in the Army.

 

 

 

 

Meeting a Hero's Wife

 

Image from UnSplash.

This is a short post which basically revolves around the unexpected meeting I had yesterday with a very special person.

Nearly every Friday afternoon I attend a LGBTQ support group (virtually) at the Dayton, Ohio Veteran’s Administration hospital.

It is one of the best support groups I have ever been involved in, and it is rare that all the original attendees still come to the meetings. It is a very diverse group with everyone from gay men and lesbians to transgender women like me. Yesterday we had a full house including a new participant who I assumed to be a questioning lesbian ciswoman.

I turned out to be very wrong and as the hour meeting went on the moderator very skillfully brought it out of her why she was there. It turns out she is the wife of a hero. Her spouse is one of the transgender service persons forced to leave the military by the supreme coward who dodged the draft “Captain Bone Spurs.” Better known as president tRumpt. When she told their story, I was wowed and expressed my position that her spouse was a true hero and would she be joining the group in the future.

Since she said, they were just exploring the area for LGBTQ contacts, that would be a real possibility. And I was thrilled to have the chance to meet her. So, I will see if I have the chance after the Christmas holiday when we have our next support session. I will let you know what happens.

In the meantime, my wife Liz and I will not be attending any concerts by the Cincinnati Symphony Orchestra this season. Years ago, I tested my courage and even found a sequined formal dress to wear to a holiday concert with Liz. Even though, it was not my favorite form of music, I managed to calm down and enjoy the show when I learned not everyone else was looking at me.

We even stopped for drinks on the way home (in an Uber) so we would not have to drive and had a great time. Since Liz is a Wiccan, we don’t celebrate Christmas as such, we celebrate Yule instead which is close since the Christians “borrowed” Christmas from the pagans in ancient times. Plus, my daughter converted to Judaism years ago, so I am pretty much left out of the Christmas holidays altogether which is a total change from the years with my second wife who was a fanatic. Poetic justice, I guess.

Even though those days are past me, I am fortunate to still have Liz’s family to feel the holiday warmth from. I know many in the transgender community are not so well off this time of year.

For me, just the chance to meet a hero’s wife in person was a huge gift unto itself. As I said, I hope she comes back for more interaction and brings the hero with her.

 

 

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.

 

 

 

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.

 

                                                                                                                                          . 

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.