Vacation Post

 

Image from Johannis Keys
on UnSplash.

The day finally is here before my wife Liz, and I depart for our long-awaited journey to the Florida Keys very early tomorrow morning. So, this will be my last post for approximately ten days. The first time in my history of writing a blog I have missed this much time in over a decade. 

As luck would have it, we are traveling on a charter bus and there are hefty storm warnings for the bus to attempt to out-run when we depart Cincinnati very early Sunday morning. 

Outside of the weather, long term, I have spent quite a bit of time worrying about potential hassles I may receive from a stray transphobe in the group. Magically however, after we packed this morning, my fears began to disappear. As Liz told me, this is not our first trip, and on the other ones, I have had no problems. In addition, I have steeled myself to facing any detractors if I run into them. Confidence in myself is one of my keys to a fun trip. After all, I paid as much as the next person to go on the trip.

After we arrive in the Keys, I am going to do my best to enjoy the brief respite to the Ohio winter and even try swimming for the first time as a transgender woman. Hopefully, this trip will be less physically demanding on me since I have mobility issues. Since the last trip we went on out west to Colorado seemed to leave very little time to relax and enjoy our surroundings before moving on, I was exhausted before we came back. I didn't like it.  Plus, this time, I have made sure I tried to walk as much as I could to build a little stamina. 

I look forward to rechecking back in with you all after we return and hopefully share a few pictures of me with my new short hair cut. 

I'm sure I will go through some sort of withdrawal when I can't write daily but then again, a little break should do me good so I can refocus my efforts. 

Hope to see you then. 

Gender Harmony

 

My friend Racquel and her dog.

When asked when I first realized I had issues with my gender I began to tell the truth and say I had known forever.

In fact, my statements were only partially true. I knew something was wrong with me, but I did not know exactly what. When I was young, I knew how much pleasure I received when I dressed as a girl. What I was lacking was the knowledge of how much harmony I was missing by learning the aspects of living in two genders.

Over a long space in time of nearly fifty years, my male and female selves battled it out, which naturally created huge disruptions in my life. My already frail mental health was in shambles most of the time. Since I had already been diagnosed as being bi-polar by a therapist before, my gender issues seemed to be a bigger problem. In reality, both issues were working together to make my life miserable before I took action and did something about it.

I started with the easier one, my bi-polar condition. After I tried several medications, I found the right ones which I am still taking to this day. The much more difficult of the two issues destroying my inner harmony was my issue with my gender. Had I listened to my first therapist years ago when she told me there was nothing, she could do with me wanting to be a woman, I would have been better off. Maybe I would have been able to relax more with my issues and realize my transition into transgender womanhood was going to be a scary yet exciting journey I should try to relax and enjoy. Rather than fight and destroy my mental health as I did it. Plus, what made matters worse was all the people around me I attempted to make miserable too. Leading my second wife to even consider telling me to be man enough to be a woman. The problem was, back in those days, I did not have the feminine experience yet to do it. So, my miserable life continued.  Any sort of gender harmony seemed to me an impossibility.

During that time, I really set out to seriously discover what measures I would have to take to restore any sort of harmony to my life. Which essentially saved my life after a failed suicide attempt. I found I had to discover harmony or face losing my life totally. 

Initially, I was obsessing on my feminine appearance over any other aspects of being a transgender woman until my trans friend Racquel told me I passed out of sheer will power. Deep down, I knew what she was talking about. I was not and never would be the most attractive woman in the room, unless I could afford the expensive facial femininization surgery. Which I couldn't. It did not matter anyhow, since I had already decided to move forward in the world with the best possible appearance I could put together. 

Long story short, I found my path to a new life and am very fortunate to live as a full-time transgender woman. Racquel went on to several appearance altering surgeries and moved away so I have not seen her for years. I owe her for the honesty she expressed to me concerning my coming out experience. As my wife said too, there was so much more to a woman than just looking like one. Finding harmony with myself, enabled me to find harmony with others. I made friends in my new life and moved on.

Amazing

 

Image from JJ Hart

As I sat and watched a singer do a wonderful rendition of John Lennon's "Imagine" and watched the ball in New York drop to ring in 2025, I had the chance to look back and think about how amazing my life has been.

As in everybody's life, destiny stepped in and took me in directions I never thought possible. The entire process was how I perceive the supposed death experience people have when they die. In other words, they get to see their life pass in front of their eyes. If indeed that does happen, I may have to ask for a little extra time to view all of mine.

Over a long life, I have been so fortunate to experience so many things. Outside the all-encompassing world of gender for me, was when I managed to land a job in the Army with the American Forces Radio and Television Service in Thailand and Germany as a radio disc jockey. To put it into perspective, there were only sixty other troops in the entire Army who did what I did. Since back in those days, we were basically the only connection our listeners had with home, it was a very serious job. 

Once I had served my time of three years and was released from active duty, I needed to take on again my larger issues of gender identity. To do so, I undertook serious research and development. Any time I could such as Halloween parties, I began to explore public reactions to my femininized self. For the most part, people I knew were astounded and I moved on. Perhaps it was my shaved legs which gave me away. Whatever the case, time flew by, and I started to cross dress more and more in the public's eye. Plus, at the same time, I slowly began to perfect my knowledge of fashion, makeup, and hair. I discovered the more I did, the more natural I felt and the more I wanted to do. In no time at all it seemed I was accomplishing tasks such as doing the family grocery shopping as a woman and it felt amazing.

Imagine my surprise when I then discovered I was going through another major gender transition. All of a sudden, I was losing my desire to just look like a woman and I more and more wanted to explore a path to transgender womanhood. Mainly because I was feeling alive and amazing when I did it. Now we all know how difficult a gender transition is for the average human being, and I was no different. I had very few natural feminine characteristics to work with and I had to struggle completely to survive in the life I wanted to live. Especially when I hit what I call the dark period of my life when I lost nearly everyone close to me to death. 

In order to bounce back, amazingly, I was able to rely on my strong inner feminine soul to survive at all. She helped me find my way. During the bounce back period of my life was the time I found a whole new set of women friends to instruct me on how to live my new life. Included in the trio of new friends, was my new wife Liz who I never expected to meet. At my advanced age of sixty plus, I would never find another person to be close to the rest of my life. Especially since I carried so much gender baggage with me. At the time, I still maintained one tentative foot in the male world, until Liz told me she did not see any male in me at all and what was I waiting for. Go ahead and fully transition. I was amazed and still am since it was over thirteen years ago when our relationship happened and is still going on strong today. 

The end result of watching the ball drop to welcome the scary year of 2025 was I have been so fortunate to have led an amazing life so far. Mainly because destiny has been on my side, and I have lived long enough to accept it.  

Happy? New Year???

 

Image from Kateryna 
on UnSplash.

Well, I was preparing in my mind last night to write my usual semi-positive post concerning the new year which is here...but.

When I awoke this morning, all was changed when I heard of and watched the news coverage of the terrible disaster in New Orleans. If you are not familiar, at least ten people were killed and thirty injured when a driver drove around barriers and crashed into a crowded Bourbon Street full of innocent people.  

Needless to say, any ideas I had about making resolutions for the new year such as coming out of a dark closet seemed to be pointless. I have always believed making a new year's resolution to live as your authentic feminine self-more than you ever have before is an honorable choice to begin a new year. I know also, many of you may have thought about pausing your gender transition because of the possibility of problems which might occur with the incoming administration.

Whatever you decide to do, please be safe doing it and do your best to have a happy new year. 

    

Dream On

 

Image from Darius Bashar
on UnSplash.

Last night I had a dream which may have signaled my subconscious mind has finally caught up with my reality. 

For the longest time, since I transitioned into transgender womanhood over a decade ago, I wondered why my dreams still had me as a man. All the way to people using my dead name with me. I woke up frustrated it was even happening at all. When I was very young, all the way to my teen years, I cherished the nights I could fall asleep and dream of being an attractive girl. Of course, when I woke up, I was very disappointed to learn I was still stuck in my same old male world. 

Years passed by and I proceeded to work very hard to resolve my gender issues but still had the same old male dreams. Who would have thought it would be this difficult to change me completely, including my subconscious dream world. For some reason, last night, the dream switch was flipped. As I said, even to the point of the world using my legal feminine name I changed years ago when I journeyed out of the closet.

Maybe the dream was reflecting all the tension I am feeling on my wife Liz and I's upcoming trip to the Florida Keys. Since it is a bus trip from Ohio, we will be traveling through several states not known for easily providing rest room privileges to transgender women. Not to mention, the possibility of encountering a stray transphobic gender bigot on the bus itself. Liz keeps telling me I am overreacting and just being paranoic. I hope she is right. Maybe last night's dream was a higher power telling me to relax and enjoy the vacation. 

Regardless, I am going to take a ten-day break from writing during our trip. It will be coming up this weekend and will give me a chance to refresh and start all over again when we return back to Ohio. 

During my vacation and beyond, it will be interesting to find out if my dream world has reached the tipping point to my authentic feminine self. Perhaps it is unrealistic of me to think ten plus years of trans womanhood could overcome nearly sixty years of living as a man in my subconscious mind. The whole process isn't the most trying problem I have to conquer. But it would be good if I could. Even in a dream world, I still do not like to be referred to as my old male name or be back living in a male world at all. 

Total erasure of my past is my goal. Although I cannot ignore all work my guy self-put into our life to set me up for success as a transgender woman, it is still a process I feel I need to complete. In the meantime, I know dreaming is a natural part of life. Now I can hopefully relax and look forward to a good night of sleep in my authentic world.  

All Hands on Deck

 

Image from UnSplash

As I progressed farther along my long and difficult gender journey, there were many times where I wished I had company to aid my path.

Even though I often whine and cry concerning the lack of assistance novice cross dressers or transgender women have early on in their progression, the fact remains we need to work our way through it and do the best we can with our fashion and makeup. Until I began to see positive results, I am sure I looked like a clown in drag. Still, I was alone with my thoughts. I am old enough to remember with "Virginia Prince" and her Transvestia publication first came to my attention. It provided me with the first real look at others who shared the same interest in being femininized and looking like a girl. I was mesmerized with more than a few of the cross dressers I saw in the publication. I so badly wanted to be like them.

For years as I worked alone to look more realistic as a cross dresser, I still yearned for feminine help. I thought any cis woman could help me because of their years of practice and interaction with their peers. When I was engaged in college, the opportunity to be dressed from head to toe as a woman by another woman finally came my way. Somehow, I begged my fiancé to do it even though I don't remember now how I did it or was so persuasive. I went all the way by even renting a motel room for all the pre-prep work such as shaving my body I would have to do. 

Once I shaved and dressed, I was excited to undergo the long-awaited makeup process. Since she wore quite a lot of makeup, I was confident she could do a great job. It was finally time for all hands-on deck in my young cross-dressing life. Back in those days, mini skirts and dresses were in vogue so I brought one I found and purchased along with panty hose, heels, and a long blond wig and started the transformation process. To say I was excited would be an understatement. Time flew by as she finished my makeup, and I headed for the mirror. Instead of the beautiful blond I thought I was going to see, I was actually disappointed. I could not see much difference in her efforts from my own. Even still, I acted as if I was really impressed with her expertise when in fact, I was impressed with how much I had learned on my own over the years. 

It took me a long time working with makeup to learn each of us has a blank face to work with and we need to learn the best way to work with it. My fiancé was doing the best she could with the knowledge she learned from her own face, not mine. She was far from being a professional such as the help I finally received from a true makeup pro at a transvestite, transgender mixer I attended years later after I was discharged from the Army. He taught me lessons about my face I had never even considered such as which features to play down and which ones to build up. To this day, I owe him a huge vote of confidence and thanks.

It turned out the opposite happened with my fiancé. Due to knowing my deepest, darkest secret about being a cross dresser, she said I should use it to dodge the draft and stay out of the Vietnam war. There was no way I was going to do that, so we split up shortly before I was to leave for basic training. Actually, it was the best thing which has ever happened to me in my life. The pain it caused immediately would have been nothing like the suffering we would have gone through if we had stayed together.  

Looking back, at my life's work as a transgender woman, for the most part, it has been a solitary experience. Not having a female peer group to interact with and learn from was a problem to be sure but one I learned to work around. The end result was, I needed to be better than the next woman to make it. 

I Never Felt so Alive

Image from JJ Hart

 
One of the main reasons I found my way into transgender womanhood was when I was exploring the lifestyle of a trans woman, I never felt so alive.

It all started when I resolved one night to change my basic mind set from just thinking I was a part time cross dresser all the way to considering changing my mind all-together to I was a woman pretending to be a man, and I was so tired of feeling that way. All of my new thoughts centering on my gender led me to what I came to consider as my second grand gender transition on the night I went out to a venue to blend in with all the other professional women who were getting off of work. The difference was I did not just want to blend in, I wanted to be them. Even though I was petrified of what I was attempting, I made it through and even was accepted by all I encountered. 

The bottom line was I never felt so alive in my life and knew my life had changed forever. The problem was, in those days, I had serious male baggage to deal with. Similar to many of you, I had a spouse, family and good job to think about even though dealing with them as a male was pulling me down. Regardless, I kept on fighting and learning more and more about the femininized life I was considering undertaking. I was naive and thought I had achieved my goal of learning everything I could about living as a woman when I was just starting my path. I put all those years of just thinking my life would be just one of appearance. As my wife kept trying to tell me, I had a long way to go to learn what the life of a woman was all about. She was right, and I resolved myself to find out what she meant. 

Primarily, what I learned was a woman's life was very layered and difficult to experience because finding women who were willing to allow me behind the gender curtain were difficult to find. I was left to learn it all by myself until I reached a certain level of transition. In other words, I needed to pay my gender dues until I earned my path to the girl's sandbox. Often the route was bumpy, rough, and unforgiving but I lived and learned. Even though (as I always mention) I found friends to help me, I needed to basically keep my mouth shut and observe how the world around me was going about their everyday lives behind the gender curtain as women. 

Through it all, I continued to feel more alive than I had ever felt before as a male. I can compare the process to being guided by a searchlight in a gender fog which was my gender dysphoria. Call it gender euphoria or whatever, I could not wait until I could take the next step towards a complete life as a transgender woman. 

I Never Felt at Home

 

Image from JJ Hart

Rarely, every now and then someone asks me when I knew I had gender issues. 

The answer I give everyone is I knew forever there was something wrong with me. I just did not know what. Plus, by the time I realized what was wrong, I felt as if I was alone in the world with my gender issues. I was very confused. As I grew through my teen years, I knew I wanted to be a girl but just did not see a path forward. 

Through it all, I kept searching for answers. I knew for certain I felt elated and natural when I cross dressed as a girl and never quite felt at home when I was with a group of males. I felt as if I was an outsider looking in. 

The older I became, the better I was at hiding my feelings. I tried my best to do all the usual male activities such as playing sports and working on cars. I played the male game well to hide my inner most feminine feelings but all along still felt like an intruder. It wasn't until I began to seriously explore my transgender womanhood did, I finally learned the truth, I was not meant to live a male life at all. As I recently wrote, I was stuck in some sort of a gender never-never land I was destined to never escape. I spent too much time pitying myself and playing the gender victim before I stepped up to face my problems.

In the meantime, the biggest problem I faced was deciding what to do with the increasingly immense amount of male baggage I was accumulating. After being discharged from the Army and finishing my second college degree, we added my daughter to the family, and I suddenly needed to become serious about beginning a career which I could support a family on. Then came the route I followed to a successful job I would probably have to give up if I transitioned to a transgender woman. As I advanced up the corporate ladder, at all the macho leaning meetings I needed to attend, I still felt completely out of place. No matter how successful I was.

Then there was the biggest piece of baggage of all which was my second wife. Although, she knew from day one I was a cross dresser, she drew a line in the sand when it came to any idea at all I was transgender and wanted to begin gender affirming hormones. She and my male self-formed a formidable pair when it came to any idea of me going any further towards transgender womanhood. When she unexpectedly passed away at the age of fifty from a massive heart attack, my male self-lost his strongest supporter and he just faded quickly away.

At the same time, I was building a new set of friends who happened to be women and lesbian and I had never felt so at home in my life. They embraced me for my authentic self while at the same time I relaxed and learned so much about womanhood from them. I never thought possible, life would ever be so fulfilling again since I was already sixty. It was well over a decade now and during the same period I met my current wife, Liz. 

Feeling at home for the first time in my life was the best possible feeling I could ever have. 

Expedition Transgender

 

Image courtesy JJ Hart

The half century journey I embarked on to finally come up as my true authentic self was certainly an expedition. 

As I always mention, my discovery began with going through my mom's underwear drawer and trying on nylons, bras and girdles I could still fit into before testosterone poisoning really set in. From there, I progressed into makeup and very slowly began to increase my craft. I did not really want to look like a clown in drag so I did the best I could. 

Life went by and so did my expedition. Sadly, for several reasons, I developed several coping mechanisms to mask my gender truth. I tried and tried to convince myself my desire to wear women's clothes and look feminine was just a harmless hobby and perhaps was just a phase in life I was going through. It took me years to realize the true phase I was going through was that I was a male at all. With sheer willpower, I managed to learn to play the male game fairly successfully and lived a life which shielded my feminine self from most all intrusions. I went into my dark lonely gender closet and slammed the door.

It took me years to have the courage to open my closet door and tentatively look around. When I did, my expedition took sudden and encouraging turns. The more I tested the public as a transgender woman, the more successful I was. I set out to sample as much as I could of a woman's lifestyle and discover my feelings on what would happen next. I tried going to gay and lesbian bars as well as big sports bars and found I could carve out a spot as a regular in a so-called straight venue. I also tried to go to various other places such as bookstores and other retail venues single women would go. In other words, I was obsessed with coming as close as I could on my expedition to seeing what a cis woman went through in her life. By doing so, I could make the final decision on where I wanted to go with my life, as a man or as a woman. 

As my expedition transgender progressed, I found myself in a face-to-face decision on beginning to take gender affirming hormones or not. Since my only real opposition to beginning the hormones had passed away, my ultimate path was clear, and I sought out a doctor for approval. He checked me out and determined I was healthy enough to begin HRT with minimum dosages of Estradiol and a testosterone blocker and my life changed forever. All the changes which occurred would fill another blog post themselves. Perhaps the biggest overall surprise was how quickly my body took to the new hormones. So fast, I needed to rethink how quickly I was going to have to change the timetable of when I ultimately wanted to finish my expedition and enter my own transgender womanhood.

I learned the fact of the matter was, I was always living a gender lie. I had refused to accept the fact I was always deeply feminine and was forced into a male lifestyle from some cruel twist of fate. All the time I thought I was a man attempting to be a woman was wrong. I was a woman attempting to be a man.

I wish I could have a portion of my life back to re-center my expedition and start all over again.  

 

Getting What you Want

 

Image from Aiden Craver
on UnSplash.

This is not really a Christmas post, even though in many ways, it fits in well with the season. 

As I was growing up, I vividly remember being asked what I wanted to be when I grew up into an adult. I also remember lying and saying something like a lawyer or doctor. Anything to make my parents happy without telling whoever asked, I really just wanted to be a girl when I grew up. An answer such as that would have landed me in all sorts of trouble.  

I progressed through life doing my best to navigate a very dark and bumpy gender road without much help from anyone except the occasional therapist. Through it all, for the longest time, getting what I wanted was a faraway dream. During my gender journey, I faced all sorts of problems such as my reoccurring issues dealing with my feminine appearance. Like so many of you, I needed to learn the fashion and makeup arts all by myself with no one to help. Back in those days, there were not the plethora of on-line makeup videos and special makeup stores to help a novice cross dresser along.

Then there were the up close and personal meetings I had with the impossibly feminine transsexual women I met. Interacting with them made me feel again how impossible my dream of becoming a full-time woman of any sort would be. However, it was about this time I began to take better care of myself, so I had a chance of becoming a better feminine version of myself. 

I dieted and lost nearly fifty pounds and began a regular skin routine which really helped with using less makeup and achieving better results. Suddenly, there was a light at the end of my presentation tunnel which was not the train. Maybe I could get what I wanted after all. At that point, I really became serious about exploring the world as a transgender woman. The rest as they say is history. When I did gather the courage to enter the world, I found I could survive. I discovered a great majority of the world did not care and a smaller percentage was just curious and amazingly enough, a smaller percentage yet respected me for living my truth. The bottom line was I survived and became better at life as a transgender woman.

When I did survive and relaxed, I saw my reality shining through. Maybe, just maybe, I could shed the shackles of my old male existence and live my gender dream. I could answer finally my own question of what I wanted to be when I grew up. A woman. To further the process along, I was able to begin gender affirming hormones which femininized me even further. My facial lines softened, my hair and breasts began to grow, and my emotions softened to the point where I could cry freely for the first time in my life. Through it all, my body was asking me what took so long to start HRT.

Looking back, getting what I wanted was the most difficult trip I had ever taken in my entire life. Pure perseverance and destiny helped me along to a full-time life away from my old unwanted male self, into a life I always wanted.   

Creative Gender Tensions?

 

Image from Levi Stute
on UnSplash

As I moved along my long and bumpy gender path, seemingly I created many gender tensions which were overblown or not needed at all.

It all started innocently enough when I first caught a glimpse of myself for the first time wearing makeup and a dress in the family's full length hallway mirror. Immediately, I knew I was hooked and could not wait to cross dress again for my own personal pleasure and delight. Sadly, the gender tension began when I could not dress again for a while. All of it sometimes became unbearable when I woke up in the morning not knowing if I wanted to be the boy I had always been, or the girl I was increasingly wanting to be. To say the least, life was very confusing, and I felt I had to be the only person in the world dealing with the same gender issues.

In the pre-internet years (along with social media), I was in the so-called dark ages of information. I had very little in the way of outside information to guide me along or challenge the many new ideas I was considering when it came to my gender life. Everything was out of focus including my sexuality. Did I like girls at all or did I just want to be one. The tension was real but still I kept struggling along trying to be the best male bodied person I could be. 

Then the internet came along and with it, my life was changed forever. Once we could afford a computer, suddenly I found how un-alone I was and how many others there were in the world with similar gender issues to mine. Of course, I was just not content to read about others, I needed to try to interact. I became involved with several early chat rooms which eventually were discovered by my second wife when she learned how to search my browsing history. Even though the great majority of the people I chatted with were not geographically close to me, I found one who was. In fact, he was within fifty miles, so a meeting was certainly possible. That was until my wife found out and an all-new battle broke out over the control of the computer. Until I learned more about erasing my history on the computer, I needed to stay off of it. Which created a new set of gender tensions. 

Living with my tensions became second nature over the years. I followed the same old up and down patterns of being up when I cross dressed, to being down when I was forced back into my male life. I rode the edge of a double-edged sword for years until I finally decided to face the truth about myself and be me. Still, it took me years of careful exploration of my transgender womanhood before I cautiously decided I was on the right path. Once I did, much of my gender tension disappeared and I knew I was making the right move for a change. All that was left was to make the crucial decisions about who I was coming out to and when.  When I did come out, I was met with approval from my daughter and rejection from my brother, so I suppose it could have been better or worse. I still had immediate family when I did it which decreased my tension along with providing me extra confidence in myself, I never had known before. 

By now, perhaps you are wondering where the creative portion of all of this comes in. All the time when I was traveling my gender path to transgender womanhood, there were many chances to zig when I should have zagged, and I ran into problems I needed to get out of. Mostly trying to navigate the problem of expressing my new transgender self while still being involved in a committed relationship. All I can say is somehow I survived and made it to my new life as a trans woman. 

When I did, my tension went away, and I was able to live a life free of gender problems which had plagued me my entire life. The relief was real. 

Transgender Procrastination

 

Image from JJ Hart

During my life, I have developed with an excessive amount of procrastination. Who knows, maybe it started when I put off doing my homework until the last minute. Later on, I began to connect the dots to me pursuing a life as a transgender woman. In other words, why did it take me over a half century to finally decide to leave my male life behind and the confines of my dark gender closet.

The easy answer is I kept putting off what I did not understand or want to face about myself by cross dressing my life away. To be certain, it was a series of stop-gap measures designed to help me survive life at all. When I was able to cross dress in front of the mirror or later at transvestite mixers I attended to see for the first time, others who perhaps shared the same gender views as I did. Ironically, I found I was wrong as I found most of the others at the parties were still a bit (or a lot) different than me. I did not quite fit in with the transsexuals or the cross dressers who were seemingly still stuck with their male selves which they were still attempting to deny. 

Still, I survived and slowly began to carve out my own life on my own terms as a transgender woman. Of course, even then, I still was the mistress of procrastination. Increasingly as I began too seriously explore the world as a transgender woman, I could not procrastinate any further. The result was I needed to merge my conflicting genders the best I could. The holidays proved to be the best time for me to try to do it. 

I have already written about my adventures shopping for my second wife when it came to buying her a matching oak bookcase and my time shopping for the perfect garden accessory. As I have promised in the past, I have not written yet about my times searching the antique malls for the perfect vintage gift for my wife. The added benefit was I could complete my Christmas shopping as a woman.

It just so happens, one of the largest antiques malls in the Midwest where I lived was located in my hometown. It gave me extra time to shop since I did not have to drive far to get there to the mall. I had several favorite things to do once I arrived and made a last second check of my hair and makeup in the car mirror and went on in. The benefit of vintage shopping for my wife was at the same time I could admire myself in one of the many available mirrors of the vintage furniture for sale. 

The furniture was not in my budget but items such as vintage seed boxes were. In fact, during those days, the seed boxes were a hot item for gardeners everywhere, so they were pricey. Still, I persisted until I was lucky to find one from another company, she did not have in my price range. The other benefit of shopping in the antique malls was I could really relax and enjoy the experience. Back then, the feeling of my feminine clothes and the interaction I was having with the public was so new and exciting. Plus, I could not wait to see the look on my wife's face when she opened the gifts I found for her. Back in those days, we had three Christmas gift celebrations. Two with each of our families and one just between ourselves. The giving of gifts between us always came last and always included the gift or gifts she reserved for my feminine self. 

My procrastination always extended to shopping at the last minute. As a trans woman or not. Perhaps I was addicted to the excitement of waiting until the last minute to find and give the perfect gift. All tempered by the fact I was shopping as my true self.

All of the experience added to me not waiting any longer and finally deciding to take a huge weight off my shoulders and do the right thing. Quit trying to live a lie as a man and begin a new life as a transgender woman. Facing my truth led to the end of my gender procrastination. 

The Stare

Summer Image Dining Out
by JJ Hart.

 
Last night, my wife Liz and I went out to eat with her son as an early Christmas gift to him. 

We went to our favorite restaurant, and they were packed with early dinner guests. Since they normally turn their tables quickly, we were not overly concerned about being seated in a timely matter.  I need to mention also, I have never had any problems at the venue with being treated as my authentic feminine self. Last night could have been a little different. But was it really?

The surprise came when we parked and a woman looking out at nearby window was staring at me. Before we even came in the restaurant. I ignored her, and we went on in and were seated. It just so happened we sat near to her where she could continue to look at me. Then the stare down became more serious as again I tried to enjoy my dinner and ignore her. 

Finally, after I glanced her way a final time, she was smiling at me, which could have meant many things. It could have been she spotted me as a transgender woman and was ready to make a scene all the way to she was just being friendly. So, I decided to smile back then go back to my dinner as if nothing happened. It worked. From then on, when I quickly looked back at her, she had obviously lost all her interest in me and was talking to the other woman she was with. I never saw her look at me again.

So, it turned out I won last night's battle, but I know I am a long way from winning my overall transgender war. In an earlier life, I was ravaged by testosterone poisoning which I face to this day. Which means I have to work very hard to obtain any of the passing privilege I may have earned when I was younger. Plus, now, with the added mobility issues I face at the age of seventy-five, it is difficult now to walk at all. Let alone walk like a woman. 

Still, I refuse to accept defeat and walk as far as I can daily, and I will not give into in any stray transphobes I may run into. Who knows, maybe the woman last night was just trying to be friendly.  After the previous disastrous election, maybe I am just paranoid. I know I am fortunate also to have my wife with me most of the time to run some sort of interference for me if I need it. However, I know I need to fight my own battles when and if they arrive. 

Perhaps the biggest test I will have is coming up in a couple weeks when Liz and I embark on a bus trip to the Florida Keys. There will be plenty of tests on my restroom presentation to see how much I have learned over the years. 

I will see how many stares I will receive. 

Trans Girl Shopping

 

Image from Sam Headland on UnSplash.

Many Christmases ago, in the early two thousand's I began to do most of my special gift shopping for my second wife as a transgender woman. Needless to say, I learned a lot. 

My wife was a huge gardener, so greenhouses and specialty garden stores were my first places to go to if I was to ever find the special gift, I was looking for. To find the best selections, I normally made the hour trip to Columbus, Ohio which had bigger greenhouses and even a specialty garden store in one of their upscale malls. Since at that time, I had a reasonable amount of spendable income, almost nothing was out of reach for me as a gift for her. 

Normally, I made the trip during the day and wore professional women's business attire. My hope was I could present well as a woman just on her lunch break shopping for last minute gifts. Even though, I was beginning to feel more and more at home as a woman in the world. Still, I felt I needed to work hard to be able to present the best I could as a transgender woman to avoid detection. Seeing as how I was knocking out two birds with one stone, I needed to do it well. 

I should not have worried because one way or another I was treated warmly by more than a few of the clerks I faced and at the worse with indifference by others. I found the older clerks were more apt to help me and the younger ones left me on my own to shop. Even being left alone was alright with me because I was so intensely trying to find just the right gift for my wife who did not know it was my feminine self-doing almost all her shopping. Along the way, I found all sorts of unique gifts from new garden tools all the way to vintage seed boxes in antique malls. Which is a different story for another blog post which I will write before Christmas. 

Perhaps you are wondering what I wore for these new yet scary shopping adventures I was on. Depending upon which mall I was going to, I attempted to scale up or back on my outfit so I would not appear out of place. At that time, Columbus featured two very upscale malls, and I could not miss out blending in by dressing in my finest silky black pant suit, blond wig, and heels along with my very best application of makeup. All my efforts worked well as nearly everyone ignored me, except a few men. 

Since I was being successful in my transgender womanhood, and I was able to be out in the public's eye for an extended period of time, I decided to push my boundaries and stop to eat and use the lady's room. Both were a challenge for me since I had rarely done it before. I gathered my courage and stepped into one of the sit-down restaurants in the mall and just took a seat at the bar to eat. Sure, I was scared of having any one-on-one communication with the public but on the other hand, I was so successful so far in the day, why not push my luck. 

It turned out all my fears were unfounded as I was treated well in the venue I chose and the only problem I had in the restroom was navigating my way around using the toilet in my pantsuit. I did not think far enough ahead when I chose my outfit for the day and put fashion ahead of rest room utility. Fortunately, I was able to complete my struggles successfully, take care of business and leave the lady's room before anyone else came in. 

I finished the day of trans girl shopping as a very successful experience with the added positives of finding great gifts for my wife. I could not wait to do it again.

NOT for Entertainment Only

 

Image from Alice Alinari
on UnSplash

As I went along my path to transgender womanhood, I found the journey was never a choice and was not for entertainment only.

My journey did not begin that way. Similar to many of you, I started by exploring my mom's underwear drawer and wearing what would fit. All of that was seemingly innocent enough unless I was caught. Then there would undoubtedly be hell to pay, along with a trip to a psychiatrist. Later I would wonder if my mom ever knew because her underwear was stretched out, but she never approached me at all. 

It was all fun and games until it wasn't. Slowly, I learned wearing girls/women's clothes was not for entertainment only. I was becoming increasingly serious about it. For the first time in my life, I was obsessing over how I looked. How was my makeup and very limited access to a wardrobe appearing in the mirror. I even went as far as shaving my legs when I thought I could get away with it. In addition, I did my best to study the other girls around me. I did not know it then, but I probably was wearing makeup before a few of the girls I knew were allowed to do it. At the time when I could not seem to muster the same passion for building the model cars I had and painting them well, makeup was an entirely different challenge and one I could not resist doing my absolute best at doing well. With no help whatsoever. 

I found, for the first time in my life, I was completely serious about doing one thing and it was being a girl. Not just looking like one. It took me years to learn just gazing at my reflection cross dressed as a feminine person was just not enough. I needed more. My problem was early on was having the budget to do anything such as being able to afford having a nice wig. It was not until my college days until I could buy a long blond wig I cherished for years. Spending all the money on one specific fashion accessory proved my passion to look good was not for entertainment only. I was really serious.

Of course, then I really started to step up my gender game. When I was released from my military service, I began to seriously explore the world as the feminine trans woman I was destined to become. As I write about often, my journey was filled with ups and downs and my mental health suffered. Definitely not the way I thought it would be when I looked at myself dressed as a girl in the mirror early in my life. What I never had a chance to consider was I was not a transvestite or cross dresser at all. In fact, I was a transgender woman and needed to accept it. I was never in it for the entertainment and my life depended on a successful outcome. 

What I mean is, I needed to stop all the self-destructive behavior I was exhibiting as I sought to destroy everything successful, I had ever done. Along the way, I had tried to lose jobs, drink too much all the way to trying to kill myself with pills. Never realizing how much I had to live for if only I followed my transgender path far enough. 

I wonder now, if I had realized how difficult my journey would be and not be entertaining would I have ever undertaken it at all. I also realize now, I never had a choice, and my life would have been better had I realized it sooner. I would love to get back just a tiny portion of the stress and tension I lost during my life as I worried about my gender. Outside of a few therapists who tried to help me by telling me the truth about myself, I was on my own. My life was never for entertainment only as I followed a gender path full of turns and dead ends before I discovered my truth in my transgender womanhood. 

Mountain of Hope...Mound of Ash

 

Image from JJ Hart

On occasion when I was following my very long path to transgender womanhood, I did experience enough hope to keep moving forward towards my ultimate goal of living a fulltime feminine life. 

Those were the days I was on top of the world and felt good about my life as a whole. Sadly, too many times my dreams were crushed mainly with me making poor gender decisions. Those were the nights I returned home with tears in my eyes following brutal interactions with the public. I was at the least stared at and at the worst laughed at to my face. Since I had only the mirror to blame for lying to me, I needed to find a better way to improve my presentation as a novice cross dresser or transgender woman. 

Really, the only recourse I had was to keep going out hoping for the best and expecting the worst. Very gradually, out of sheer will power, I did become better at my craft and my confidence grew. I was climbing my mountain of hope and staying there. Sadly, my only mound of ash came when I was discovered by my second wife when I was returning home after a night out. Predictably a massive fight would happen, and feelings would be hurt. It wasn't until years later when I finally had the courage to face my gender truth and finally transition. By that time my wife had passed away and it was a moot point. Following her passing, I found I had another mountain to climb. 

My mountain was one of loneliness. For the first time in over twenty-five years, I was by myself with only my two dogs to take care of. No other person to worry about disappointing with all of my gender adventures. It did not take me long to decide which direction to go with my life. My inner feminine soul was screaming to be let out and for once there was nothing to restrain her. She was my woman, and I was her.  With new enthusiasm, I began to climb again. Sure, there were still setbacks and problems with my new life. A primary example was when I tried to date men and was constantly stood up on potential dates. Fortunately, when I began to be accepted by lesbians, I found I did not need a man to be validated as a woman. 

When I climbed my gender mountain, I began to begin too clearly see what was going on around me. As all the clouds and doubt parted and I could see there was only one path for me to pursue. I finally gave up on my male self, gave away all his clothes, started gender affirming hormones and never looked back. 

When I finally freed myself up to be me, I never had felt better. It was a huge weight lifted off my shoulders which I had carried way too long. Since I am afraid of heights, climbing my gender mountain was never easy but I made it. 

Trans Fun?

 

Holiday Image, JJ Hart author.

Are we having any fun yet as the holidays are upon us? 

Certainly, it is a tough time of the year as transgender women and trans men face the daunting task of facing unapproving families. Too many of us face a lonely existence this holiday month. In many ways, we are uniquely qualified to face the challenge. For those of us who were ravaged by testosterone poisoning and not gifted by natural feminine features, our path is a steep one to finding any acceptance at all in our transgender womanhood. 

In my sense, there was only brief gender euphoria moments during too many instances of rejection by the public. Every now and then, I would have moments of fun when I briefly succeeded at my goal of successfully presenting as a woman. Then, all too often I would ruin it all by not knowing how to move as a woman or more importantly having any idea how to communicate with the public as the person I had always wanted to be. 

Through it all, I did have enough fun, or at least satisfaction to keep moving forward. To be certain, there was a difference between having fun or being satisfied with what I was doing. To be satisfied meant deep down I felt natural when I was pursuing my feminine dreams. To put it another way, there was a flood of water under my gender bridge primarily in the decade after 2007 when my second wife passed away and opened the door to a total transition into transgender womanhood. If I wasn't hanging out with lesbians in their venues, I was finding my way in big sports bars as a regular. Slowly but surely, I learned I still was alone on my gender path, even though I was meeting and learning from a few of the cis women I stayed close to. It was difficult because I had always trained myself to keep everyone else at an arm's length so I would not be hurt. The difference was now I was finally at the level personally where I wanted to be as my authentic self so I could accept new friends.

If I had liked, it or not I had finally reached the bottom-line where I had always wanted to be. When I did, I began too actually relax and enjoy myself. Which means I was having fun, regardless of myself. Perhaps I was fortunate in that my path forward was complex but maybe not as complex as is the norm these days. Social media contacts were just becoming the norm and maybe it meant the tons of trash I needed to sift through to find my wife Liz was destiny and not luck since she actually sought me out online after reading my profile. Then, there was my public persona which I don't necessarily recommend because I was going out to venues as a single transgender woman. Back in those days at least, one did not have to worry about someone else putting date drugs in your drink while you were not looking. 

Looking back, I did have fun during those days and primarily it was because my confidence in my new self was increasing because of the people around me. I could copy what they did as women and do the best I could. Which was better than I had ever done before. I had paid my transition dues and was ready to face the future.  

Answering the Call

 

Image from Alexey Elfimov on UnSplash.

On occasion I am sorry to say it took me over a half a century to answer my gender call. But thankfully, I finally did take the call and listen to the urgent message. 

Please keep in mind I don't count all the years I attempted to cross dress my gender issues away. As I often write about, all cross dressing did was provide me with a quick fix. After I dressed as a girl, I felt better for a while before the same old tensions of life with gender dysphoria set in. The problem was, deep down I knew I wanted to do so much more than look feminine, I wanted to be feminine. 

One of the few good things which came from my gender struggles was practice made perfect. Even though I knew I was the only one who could see my progress with makeup and clothes, I stuck with trying to improve every time I cross dressed. It was so difficult for me since I only had the mirror to answer to when checking out my progress. The problem was the mirror was so good in telling me everything, but the truth and I tried to keep in mind I might look good, for a boy in drag. Not as an actual girl. In other words, I learned I needed to hold myself to a higher level than other cis women I observed if I was to survive among them. 

The entire process was so difficult for me since I had never been detailed orientated in my life. Just getting by was not going to be the way to go. I was fortunate when I encountered professionals in the makeup world who helped me along. One in particular came following a transvestite-transgender party mixer I attended near Cleveland, Ohio years ago. After the mixer slowed down, the organizers provided several makeup professionals to provide free tips to whoever had the nerve to ask. On that evening, I am happy I put my ego behind me and answered the call for much needed makeup assistance. The catch was I needed to remove all my makeup and wig and let the professional start over. His work and results were amazing, and I even understood all the tips he was trying to tell me. The end result was I was flooded with compliments and my gender euphoria soared to an all-time high. Furthermore, later on that evening, I was even hit on by a guy in a straight venue I went to with other transwomen from the mixer. 

That night, I did not answer the call to stay with the guy who showed interest in me. My reason was, I was in a strange town with a person I did not know, and I did not know if he realized I was transgender. Not a good place to be at two in the morning. On the other hand, I loved it when the other "A-listers" from the mixer were jealous of me for once.

Along the way, I ended up answering enough calls to barely keep myself going. There were plenty of times when I did not know if my mental health could take it, and I could keep going. It was then when I took the all-important call to begin gender affirming hormones and change my life forever. I was sixty by then and knew there would be no turning back. After I did, I learned taking the most important call of my life turned out to be a life survivor for me. I remember the evening when I decided to answer my phone for the last time. All of the sudden the voice told me I was free to live as my authentic self and the relief I felt was tremendous. All my previous misgivings were swept away. 

Who was the Problem?

 

Image from Ben White on UnSplash

Looking back at my long journey to transgender womanhood, I finally discovered I was the true problem all along.

I was in shock. All this time I was desperately seeking someone else to blame for my gender identity issues. I kept thinking I was alone in the world and why did it have to be me. Remember too I grew up in the pre-internet generation before there was much if any real information available to gender challenged people. The struggle was real.

It took me years to figure out I was not a man cross dressing as a woman but rather I was a woman cross dressing as a man. To arrive at such a major point in my life required years of trial and error in the public's eye as a novice femininized person. To advance to the life I had always dreamed of, required a lot of work on one hand and confidence I could do it on the other. 

Somehow, I needed to work through all my paranoia I was experiencing and begin to enjoy my new life. I equate it now with learning to dance with a new partner and beginning to feel at ease with it. Primarily when I tried to perfect moving as fluidly and gracefully as a natural woman. Moving like a linebacker at a dance was out. It all was a major obstacle towards moving to my dream. Or could I ever hope to be able to live fulltime as a woman like I had seen others around me do. Then if moving as a woman was not difficult, communicating came along and presented the greatest challenges of all. 

The act of communication came up on me quickly. As I started to go out in the public's eye just to get out of the house as a woman, the better I became doing it. I learned quickly, how many other women wanted to communicate with me. For the most part, they were just being nice and wanted to know what I was doing in their world. Once they found out why I was there and I did not pose a threat, they wanted to know more. If I did not learn the basics of feminine communication quickly, then I would be the problem if I came off as unfriendly or even worse, bitchy. To work on my fears, I went back to the mirror to practice talking as a woman. It was bad when at first, all I could come up with was a scratchy falsetto which just would not work. Initially, before I began vocal lessons, I started with a quiet background voice as I tried my best to mimic the woman I was talking to. 

Perhaps the biggest problem I encountered was adjusting to the basic passive aggressive spirit of women everywhere. Primarily, I needed to learn a smiling face did not always mean acceptance from another woman. I was the problem when I treated smiles as acceptance and learned the hard way when they were not. I think I still have the scars down my back to prove it.

It turned out, my basic stubbornness to leave my male self behind was the real problem. All the stress and tension he caused over the years cannot be reclaimed.  In the end, I needed to put all the blame on myself. If I could have understood all my gender issues over the years, life would have been so much more pleasant for me. I am sure it all goes back to me knowing I felt better as a girl and more natural. I have no idea now why I waited so long. Except I did not want to give up all the materialistic items I had accumulated as a guy. It took a transgender woman to whisper in my ear that all would OK if I just had followed my heart and transitioned. Then I would not have been the problem at all. 

Joy to the World

Image from JJ Hart Liz on right.

Gender euphoria is so wonderful to a transgender woman or trans man striving to present themselves in the world as their authentic selves. On the other hand, it is often very rare to obtain. 

The brief moments I experienced euphoria in the world when I first went out as a novice trans woman or cross dresser, kept me going but barely. The reason was, I suffered from huge bouts of  gender dysphoria which wrecked my life. It seemed every morning when I woke up and looked in the mirror, would I see the same old male I never wanted to be or somehow see behind him and view the girl I always dreamed of being. My dreams even reflected my gender issues when I would awake following a very vivid dream where I was the pretty girl. When reality set in, I was very sad.

It took me years to realize I could fight back against my gender dysphoria and do more to live out my dream of living as a woman. Years of sorrow when I failed became years of joy when I succeeded. Progress was very slow at first as I went out shopping in the world and sought out every mirror I could find to restore my faith I was indeed a presentable woman just minding her business in the world. When I discovered most people did not really care about me, my life became much easier and took quite a bit of the pressure off I was feeling. 

Still, I needed more. On every occasion I could, I was out the door seeking new places to visit as my new exciting self. I was walking the gender border and feeling the joy on some of the days I was successful and torment on the days I was not. My main problem was trying to find feedback with what I was attempting to do. The only time I did receive any response was when I went to the small, diverse parties I went to at an acquaintance's house in nearby Columbus, Ohio. From transgender admirers to inquisitive lesbians, I had a chance to meet new people in my world and see how I measured up to them. I knew I could never be a beautiful as a few of the impossibly feminine transgender women who attended but just maybe I could elevate my appearance to a feminine level where I could get by. The parties also proved to be the initial starting point of developing my own new personality as a trans woman, so they were very beneficial.

As I experienced the joy of being my true self, something had to give. Sadly, the something turned out to be my male self and my marriage of twenty five years to my second wife. Both of them suffered terribly. Naturally, neither of them wanted to lose any power. My male self was quite comfortable in the life he had built and my wife did not want to lose the man she married, so I was in for very difficult times. What happened next was my mental health went into a very steep decline. I did not know where to turn and at that time did not have a good therapist to fall back on. Then I resorted to the worst possible choice when I tried to internalize everything. By doing so, I made everything worse. 

I continued to go out as much as i could but ended up just forcing the gender issue and losing any of the joy I had previously felt. It wasn't until I decided to begin gender affirming hormones and transition fully, did I begin to reclaim the happiness I felt. 

Was it worth it? Sure as I finally achieved my dreams of living fulltime as a transgender woman. I just wish I had the courage to do it sooner. Or as my second wife told me a number of times when we bitterly fought...be man enough to be a woman.