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. 

Having an Affair

Image from Susan G Komen
on Unsplash

Years ago I experienced having an affair during my marriage  with my second wife. 

Before you condemn me any more than I condemn myself,  the affair I am talking about was with myself. That is right, myself. It happened when my feminine inner soul began to take over my life. What I was doing at the time was rejecting the pledge I had made to her to never leave the house cross dressed again. I became so entranced with how natural I felt in my transgender womanhood, I left the house any chance I could which was often. It turned out, the more exploration I went through, the more I wanted to do. Seemingly nothing was out of reach in the new exciting gender world I found myself in. Sadly, even to the point of leaving the vows I made with my wife behind. 

Let me point out also, I had never stepped away from my marriage during the twenty-five years before to be with another woman. Imagine my shock when I finally did, the other woman would turn out to be me. 

As is the case with many affairs, the passion was real in the beginning. Then begins to lessen overtime. In my case, the opposite happened. The more I explored and lived as a transgender woman, the more I wanted to do. I had a real problem on my hands on what was I going to do. On one hand, my wife had told me in no uncertain terms she would not live with another woman and on the other, I did not have the courage to tell her she already was. If I had faced reality, I would have known it was time to jump off the old male ship and begin to live a new life in a feminine world. Even though most likely, it would have cost me our marriage, perhaps we could have at least become friends in the future if she had lived. You see, she died of a massive heart attack at the age of fifty. 

The only thing I did do out of desperation was try to purge myself of most of my female belongings before she passed away and I even grew a beard. It turned out to be my last tribute to her and the years we had together. 

As with all purges, they don't last for long and one of the first things I did was shave off the beard and turn inward to myself in the lonely tragic days after her death. It took awhile but my inner female took control and let me know everything would be fine. Finally I decided she was right and decided to give up all the guilt I was carrying over the affair I had with myself. 

Once I did, my new life as a transgender woman took over. I found new friends and moved on but it took me five plus years to do it. In the meantime, I found all the work I needed to do to play in the girls' sandbox was worth it. I needed to be better than the average cis-woman to survive in the world I chose to live in. I found a woman's life had so many layers to it, I faced a real challenge. As big a challenge as having an affair in your marriage. With yourself.

My Second Gender Transition

Liz on Left. Image from a Banquet we 
attended. From the Archives. 

 I am a firm believer,  I went through more than one major transition when it came to building a new life as a transgender woman. Many transitions were helped along by friends and others I accomplished on my own. 

One of the biggest I did all by myself was one I mention quite often. It was the night I went to TGIF Fridays close to me. Just going was not so amazing, in fact, I had been to the venue many times as my male self. When I was there, I often was very jealous of all the other women I saw there, many of which were dressed in fashion I could only dream of. 

All of a sudden, I decided to make my dreams a reality and one night I set out on an adventure which I would never forget and would change my life forever. I can't really tell you why but something clicked deep inside me and I decided it was time for me to move away from being a cross dresser and explore my possible existence in a transgender world. The whole possibility terrified me more than anything else I had ever tried before in my life. Possibly because I knew if I was successful there would be no turning back. 

To begin with, I had the wardrobe I needed to wear to blend into the feminine environment I was headed. I knew the Friday's venue I was going to had a very woman based clientele which came every night at approximately the same time from a large mall which was nearby. I knew exactly, who I was trying to blend in with when I chose what I was going to wear. I chose my dressy black pantsuit, black flats, sensible makeup along with my shoulder length honey blonde wig. I felt I looked presentable enough to accomplish my goal of moving into the transgender world I was just beginning to explore. 

Once I came up with a time I could sneak out for a trip into the unknown when my wife was working late, I began the transformative femininization process. Once I thought I looked fairly presentable, I left for the twenty minute trip to the venue. Through it all, I was scared but not as scared as I would be when I arrived at the Fridays. When I pulled into the parking lot, I ended up waiting over a half a hour as I adjusted my hair and makeup in my car's rearview mirror. Once I came to the point where I could barely breathe, I opened the car door and gathered myself the best as possible. After all, I had improved from the point of not being to breathe at all to being able to walk in the front doors. 

Since I managed a similar casual dining venue to a Fridays I knew the setup, Essentially, once I made it past the hostess stand, all I had to hope for was being able to find a vacant seat at the bar. I was lucky I arrived shortly before the rush and there were several seats available. The Fridays I was going to had not remodeled yet so it had two big supports on either end of the bar. I was so scared and so lucky, I was able to get a seat next to one of these supports. I got as close as I could and tried to hide until I was approached by a friendly bartender and order a drink. From that point forward, I knew my life had changed forever. Just existing as a woman among other women in a public setting had removed any idea's of being a casual cross dresser ever again. 

In a moment, my second gender transition had taken place. My first came years previous in my youth when I viewed myself as a girl in the hallway mirror. Plus, deep down I knew the next transition I would undertake would be if I could ever undertake gender affirming hormones or HRT as it was known as back in those days. My visit to Fridays that night jump started my gender future. My problem then became how I would ever be able be able to co-exist with my un-approving wife ever again. She was certainly against being with another woman. Especially if the woman was me. So my second transition was heaven for my inner woman and hell for my wife and my marriage.  

Of course, I was able to transition even further with hormonal therapy and go on to lead a comforting transgender life. Going through the process was always not the easiest and I will always remember how I felt that night at Fridays from trying to hide behind a post all the way to how my panty hosed feet felt in my flats. It was quite the evening.

Somewhere between Heaven and Hell

 

Image from Sara Kurfess
on UnSplash

Very recently I received a comment from "J" asking me about my experiences coming out to my immediate family. After giving the comment some brief thought and I came up with this explanation, my coming out to family was somewhere between heaven and hell. 

To begin with, I had it relatively easy coming out since most of the important members of my family who needed to know anything about my transgender issues were not around. My parents, as well as many of my uncles and aunts had all passed away, leaving me only my daughter and my slightly younger brother to tell my truth to. 

The heaven and hell came in with both of these two close family members, it seemed as if destiny was showing me both sides of coming out. To begin with, I chose telling my daughter first at one of our breakfast meetings we often scheduled to catch up with our lives. One very nervous, scary morning, I chose to tell her I was indeed transgender. I will never forget her reaction which initially was a resounding why was she the last to know. Keep in mind by this time in her life, her Mom was long divorced from me and her Step Mom (my second wife) had recently passed away. So I guess she resented neither one of them telling her the depth of my gender issues. It certainly wasn't their fault because even though they knew I was a cross dresser or transvestite, even I resisted the idea of me possibly being transgender. In the meantime I was trying my best to hide any feminine desires I had from the rest of the world. Evidently, I did a good job and I was also amazed the cross dressing subject never came up with her. When she asked me why was she the last to know, I had no answer.

From then on, she gave me more support than I could have ever asked for. My daughter initially offered to take me on a shopping trip which I politely declined and then since my hair had magically grown to the point of being able to be professionally styled, she offered me a styling at her upscale spa and salon for my birthday. A gift I just couldn't turn down and after conquering my fears of going to the salon, I learned why women were so in love with their salon visits. I loved mine and I was in heaven. To the day, "J", my daughter has provided me with the heavenly acceptance I needed to make my male to female gender transition so much easier.

Now, the hell part comes in with my brother and his extended family. As luck would have it, I told my brother just before Thanksgiving over ten years ago. I wanted to know if it was OK if I attended as my authentic self or not. Before I asked out of respect, I knew the answer I would be given. My brother's in laws were all right wing leaning Southern Baptists, many of whom I always argued with during family get togethers. 

After some brief discussion with his wife, my brother sold me up the creek and said essentially it would be better if I did not attend the only family get together we planned for the whole year. The dinner was always the most important get together for my second wife and she did all the cooking a preparation for it for years after my parents passed away. So the rejection hurt a lot. I moved on quickly and haven't talked to my brother since. Which describes the end of my hellish experience of coming out to family.

Plus, I was lucky, I had my wife Liz and my daughter's extended family step in to fill the holiday void. And, I turned out better in the long term. 

I don't know, maybe destiny just wanted to show me the heaven and hell of coming out to family. While I didn't have the quantity of people to come out to as being transgender, I certainly was able to experience the quality of seeing both sides of the rejection/acceptance spectrum.

Thanks for the comment! I hope my experiences help. I value all your comments and questions! 

Regrets?

Image from the 
Jessie Hart Archives

I would suppose, similar to anyone who has reached the stage of life I have reached, may have a few regrets.

As far as I am concerned, I don't have many. Along the way, I have been fortunate to have loved and be loved by several different women. Three of which married me. In each of my marriages had their own special ups and downs. One of the regrets I do have was when I needed desperately to be the one who cheated on my first wife so I could marry my second wife. I wasn't proud of being the cheater in the relationship but I see my first wife (and mother of my only child) approximately twice a year and we get along well. We both moved on to other long term relationships which proved out to be for the best. 

I was with my second wife for over twenty five years before she tragically passed away from a massive heart attack. My regrets with her primarily revolved around me not knowing the full reach of my transgender feelings and I ended up dragging (no pun intended) both of us through the gender mess I created as I transitioned. It would have been easier if I had just pulled the band-aid off and just let the dust settle where it may. But I was selfish and still liked part of what I had accomplished as a guy. So much so, I didn't want to let it all go which was a major mistake. One which almost killed me. I would not wish attempting to live convincingly between the two main primary genders on anyone. From day to day, just to get by, I needed to concentrate which gender I was that day. I found myself in some sort of a gender twilight zone trying to figure out daily was I a man or a woman.

I did know I loved being a woman, I loved the clothes and the challenge of facing society daily as my increasingly feminine side. Sadly, as with anything else you love, many problems come with the process. Life at once became exciting and terrifying. I didn't know what I was doing as a novice transgender woman but I learned fast. At the least, I gave myself the latitude to make mistakes and keep discovering a new world. Regrets? Sure, I made many mistakes along the way as I presented myself to the world. Plus I was lucky too when I got away with more than I should ever been able to. The main ones occurred when I went behind my second wife's back to cheat on her. With another woman who happened to be me. I had always thought I was a honest person, so the whole deal proved to be excruciating to me. The more success I felt on one hand felt so natural but at the same time I was cheating on the person I loved.

I suppose everyone has regrets but destiny has softened my challenges I have experienced from the challenging idea I wanted to change my gender. Ironically, it was my third wife (and current one)who came along and saved me from myself in my darkest days. She made me a believer in myself as a person and convinced me I should have live fulltime as a trans woman. She sealed my belief in her when she told me she had only seen the feminine in me. That was over a decade ago and we have never looked back and our relationship remains strong.

It doesn't do much good to have any regrets anyhow. Life moves fast and if you didn't take the opportunity to seize it when you had the chance, it may never come around again. I am just fortunate in I have been blessed with a long life to try not to repeat my mistakes and have regrets. 

Cajun Night Out

From the Jessie Hart Archives,
my wife Liz on Left. 

Last night my wife Liz and I celebrated a combined celebratory dinner at our favorite Cajun restaurant which features a chef who worked previously in New Orleans.  Far from our native Ohio.

The weather had turned in our favor with the first night of fall weather arriving.  Which meant I could wear my birthday gift from my daughter which was a nice warm soft outer fleece. Of course, after a close shave, application of eye makeup, blush and lipstick I brushed back my long hair and was ready to go. In order to blend in with the very casual atmosphere of the venue, I wore my favorite jeans and sweater. Now I regret I didn't have Liz take a picture but at the time I felt so good about the both of us going out together, focusing on just me just didn't seem appropriate.

Once we arrived at the venue called the "Swamp Water Grille' the parking lot was packed and we knew we would have to walk which sometimes is a issue for me. However, I gathered my courage and headed into the restaurant. I found out long ago busy places are better for me when it comes to anyone questioning my gender orientation and I was not wrong last night. As we entered, the hostess cheerfully greeted us and said the wait for a table would be approximately one half hour which worked in perfectly with our plans. 

The best and most gender affirming part of the evening was yet to come when our male waiter addressed us as ladies when he brought us water to start out. At the time, I had not ordered yet and wondered if my voice was going to give me away as a transgender woman. It did not as he referred to us as ladies throughout our dinner all the way until we paid and left. During our dinner, the rest of the tables were full nearly the entire time and again no one even gave me a side glance,. Gender freedom is a wonderful thing!

Due to the enormous portions, we bought and brought dessert home with us to splurge since the evening also was reserved to celebrate our first wedding anniversary which is coming up soon. Last year, we decided to "tie the knot" after going together for nearly eleven years. I guess we did not want anything such as being legally married interfere with our happiness. It has not so far. 

Plus, outside of the wonderful companionship and great food, the whole evening did wonders for my gender euphoria. The whole process of acceptance on any level brought back the years of struggle I went through during my early years of cross dressing on the way to my time as a novice transgender woman. Last night made it all worth it.  

Impactful Month

 

Image from Stories
on UnSplash

The rest of October will be very busy for my wife Liz and I.

Towards the end of the month she has two surgeries coming up which could entail spending a couple of days in the hospital. The operations are so intense we have to go today to go over all the details of the surgeries. Plus, the pre-opt work on Liz's side starts next week. 

As far as I am concerned, I am deeply involved in the process and will accompany her to all the pre-surgical consultations. It means facing a whole new set of people I have never seen before, which sets off my interior shyness. However, I have resolved myself to stay strong primarily because I am so worried about anything going wrong. 

As you regulars know I write often about losing my spouse of twenty five years and I do not want to go through the trauma and pain of doing that again. 

Of course what I am wearing to the pre-surgical visits is a no brainer. I am wearing my good jeans and light green sweater along with a light application of makeup and my hair tied back off of one shoulder. 

Plus, before all of Liz's work happens in the latter part of October, next week I have my twice a year in person appointment with my primary provider at the Veteran's Administration. A primary provider is similar to having a family doctor. Since I was trying to save a trip, I requested my provider approve my pending blood labs for another VA provider and (if they can) set me up for my flu and Covid shots the the same time. Since I put my requests in on the VA online system, I haven't heard back yet if they have been approved. 

All things considered, recently during my last several visits to my local VA clinic, I have been treated with respect, which wasn't always the case so I am pleased. Sadly, the personnel changes so rapidly at the clinic, you never know who you will or won't see again.

One way or another, October will be an impactful month because it also contains our first wedding anniversary after being together for over ten years. Just a lot to keep track of! And I can't forget all the impactful Halloween memories I would love to re-share. Plenty of posts to come. 

Destruction

Image from Mika Baumeister
on UnSplash

At various stages of my life I survived being so very self destructive to everything around me. 

Of course being gender dysphoric as well as bi-polar didn't help. Before I was diagnosed and received medications it seemed all I did was go from being very depressed to being very mean and nasty. I am surprised my wife was able to stay around as I tried to tear down everything I attempted to build. Often I would change jobs at a frenetic pace just to see if I could. During the process I uprooted and moved my wife and I from our native Ohio, to New York City, then back again to West Virginia. She didn't like the moves but came along anyway.

It took me awhile but finally I came to the conclusion I was trying to out run my gender issues by all the moving we were doing. Since my inner feminine self didn't respect all of the work was male self was doing to be a success, she did her part to resist and tear all the work down. Very self destructive to say the least. 

One of the biggest pillars of my life which was left was my marriage to my second wife which I write about often since it lasted twenty five years. She knew I was a cross dresser or transvestite from the very beginning so in many ways dressing like a woman for me was a non starter with her. She didn't really care and/or put up with it. The deciding factor came when I began to feel the urge to see if I could actually live as a transgender woman. I can still hear her words echoing in my head, I never signed up to live with another woman. After tremendous gender focused battles and me essentially cheating on her by leaving the house behind her back, I finally gave in and tried to purge most all of my feminine belongings before she passed away. I view the whole experience now as a fight between two strong willed women, my wife and my female self.

After I began the MtF gender transition to living life as a transgender woman, I needed to go through a relearning process of sorts to not be so self destructive. Among other things, I needed to dress more conservatively to blend in to where I wanted to go and I needed to be much more wiser when I did it. I almost learned the hard way about being in the wrong place at the wrong time as a trans woman. My male safety privileges were stripped from me when I crossed the gender border and I needed to learn the new rules of being a woman...fast. 

As it turned out, my new feminine self was much less self destructive than my old male self. Once she had finally got her way, she wanted to keep it and build a much more pleasant life.

Pushing Trans Boundaries

 

Image from the Jessie Hart
Collection.. Back drop, the Ohio
River

Along the way, as the years went by I began to really push many of the transgender boundaries I faced.

A primary example was when I thought I had conquered one of my goals, such as my feminine presentation, I set a new goal. Often I went to different places and/or venues to see if I presented well enough to be accepted as a transgender woman. After malls and clothing stores became too easy for me, I expanded to stopping at restaurants to eat. Which in turn forced me into more one on one communications with complete strangers. I pushed the boundaries past just routine chit-chat eventually into full fledged conversations. I learned the hard way not to worry so much about how my voice was sounding and begin to consider more and more what I was saying. 

For a while it seemed, the challenges I was facing in those years were becoming overwhelming as I pushed my gender boundaries even further. Another major jump occurred when I decided to stop going to the so-called safe spaces which were the gay venues I was going to. I finally decided if I was going to feel like an outcast, I might as well do it in a venue I felt more comfortable in. I began to go to upscale sports bars and restaurants with many televisions and cold draft beer which I enjoyed. Since I stood out from the crowd for being transgender, I minded my own business and tipped well ,so in most places I became a regular fairly easily. On occasion, I still pushed too hard and ended up getting kicked out of a couple places I shouldn't have been in to start with. Lessons were learned.

Slowly but surely the process finally did become a blur. I made new friends and was beginning to thrive in my dream life of being a transgender woman. The biggest remaining problem I had at the time was I was still married. At that point my second wife and I had been together for nearly twenty five years. From the beginning she knew I was a transvestite or cross dresser and didn't really have any problems with it. However, when any discussion at all came up about the possibility of going further and beginning hormone replacement therapy, she drew the line.  Any time I tried to push the boundary farther, the more she resisted.  In many ways it was similar to the rock meeting the irresistible force and it was ugly. More precisely though, I had started the catfight of all catfights between my wife and my inner feminine soul who had finally been able to sample life in the world. Once she had seen the daylight, there was no way my feminine self wanted to give it up. From there, destiny took over.

When my second wife passed away, it didn't take long for my inner woman to take over. She pushed hard and became the dominant force in my life. Quickly it became evident she had known the path to take my entire life. She began to push my transgender boundaries until my life became meaningful again. My male self faded away. 

Trans Girl and the Biker

Image from Gijs Coolen
on UnSplash

Several times during my life I have encountered key experiences which involved a motorcycle.

The first was in Cleveland, Ohio and involved my second wife. At the time I was a very novice transvestite or cross dresser out for one of my first ventures in public. Since my wife and I had some time to waste, we decided to find a venue to have a drink in during the afternoon. Before the mixer began. as we sat at the bar a loud motorcycle rolled up almost completely in front of the door. His "bike" was impossible to miss. 

As it turned out, he and my wife began talking. It was the first time I really had ever noticed her flirting with another man when I had been around. Naturally, this time, dressed the way I was head to toe as a woman, I couldn't do anything about it anyhow. The worst part to me was, she seemed to enjoy watching my reaction. For the first time in my life, I was competing with another woman for the attention of the motorcycle guy. Her conversation went to the point when and if he offered her a ride and I wondered if she was going to accept. After keeping me in limbo for what seemed like forever, he did and she turned him down and stayed with her husband/girlfriend. She had made her point and moved on as I was left to wonder what could have happened had she left with him. Since she has long since passed away, I will never know.

The second experience came years later in a suburb of nearby Dayton, Ohio. In a certain venue I had become a regular in, I had been accepted into a small group of rather diverse acquaintances. One lesbian and four or five straight folks. One of them was a big bear of guy who rode a classic motorcycle and ran the lumber section of a nearby large home improvement store. Another of the "regulars" was an exotic beautiful hair dresser who danced on the side. It turned out within a fairly short amount of time, she decided to marry the big guy. I thought at the time, she wasn't the marrying type and I was right. It turned out their marriage lasted  approximately one week and it was over. To make matters worse, everyone in the group except for me seemed to not care about his feelings. Slowly but surely, we began to chat and formed a small bond.

As we did, the rest of the group as well as some others in the venue began to notice. I just felt he was hurt and needed a shoulder to lean on and it almost worked out to taking a ride on the back of his motorcycle. Which would have been my first ever. I would have/should have pursued it more except back in those days I was wearing a wig and all I could imagine was my wig flying off when I was riding. The ride never came and shortly there after, he was transferred out of town to another store. Leaving me with another "what if" moment. He was one of the few men I had ever formed a bond with and I missed him.

Whatever the case, he left and life moved on as it always does. The only other encounter with a cycle man came at a highway waffle place when I suddenly encountered a real life outlaw biker type eating his breakfast. He paid me no real attention as I tried not to notice him and nothing happened. 

To this day, this trans girl has never even been on a motorcycle at all. It's OK though, I have enough other habits to keep me occupied.

Gender in Layers

Image from Monika Kozub
o UnSplash

Quite early in life I thought being feminine was just looking like a girl/woman.

It wasn't until much later on, I discovered how wrong I was. Even though I was an avid follower of everything feminine I could find, it seemed everything I did wasn't good enough. Everywhere I turned cis-women gate keepers were keeping me out. As I did manage small steps on my gender journey I came to a point where I collided with my second wife. All along she was very outspoken in that she didn't want to live with another woman. Especially if the woman was me. So I counted her out when it came to me acquiring any new feedback from her. I was completely on my own.

Since I was on my own, I did make mistakes and sadly my biggest gender strides came after she unexpectedly passed away from a massive heart attack. It was then I was free to explore my feminine self in the world. Very quickly I learned my deceased wife was right, I had a long way to go. I needed to advance from she called the "pretty, pretty princess" stage of my life, gather myself and attempt to move forward into a world I found I knew very little about. If I was going to advance, I needed to interact one on one with the world as a transgender woman.

I started with looking at the different layers of life a woman faces which were different from a man. Of course the easy ones were family driven. Since women birth the children, often the kids were more central to their lives. No big surprise. I didn't have much problem when I communicated the fact I was a parent too when I was communicating with another woman. It was from there when the communication became a little more difficult. I was petrified the next question would be why was I dressing like a woman anyway. That question never came and often we moved on to less important topics such as jewelry, hair and clothes.

About the time I thought communicating with other women wasn't so difficult someone would come along with a passive aggressive thought which would send me back to the communication drawing board. Men were so forward when they communicated in my male world, I got burnt several times when I didn't adjust fast enough to the women's way of speaking. What was she really trying to say. Was I truly pretty or just pretty for a man cross dressed  as a woman. Finally I decided to leave all the paranoia about communication behind. Instead of what could go wrong, I adopted what could go right as my inner slogan.

Other layers in my new life as a transgender woman came along mainly after I began hormone replacement therapy. Fairly quickly my emotions were released as the world around me became softer, My sense of smell even became more intense. The entire HRT experience helped to add layers to a life which was increasingly becoming more feminine. 

Through it all, delving into the deeper layers of a woman's life helped to make mine so much more meaningful.   

The Wasted Years?

Photo from the
Jessie Hart Archives

 Many times when I am asked what my biggest regret in life is, my quick answer is I didn't transition quicker to my authentic feminine self.

However, after taking a deeper dive on the subject, sometimes I have to come up with a bit of a different answer. Most assuredly I miss not being able to have experienced all the facets of life a younger woman goes through but then I needed to realize not all early life feminine experiences were good, as hopefully she made her way to being a woman. Not every female can claim womanhood as it comes through a socialization process.

Also, saying I wasted nearly fifty years of my life living as a man would be wrong to say. I did have good times as well as experiences I am intensely proud of. Plus I think several of the experiences made me a better transgender woman when I transitioned. For example, even though the process had its ups and downs, there is no way I would have traded the experience I had when I served three years in the military. Or how could I ever give up the years when my only daughter was born and grew up. Obviously too, my second wife and I could not have made it twenty five years together if there were not some good times mixed in.

I guess you can say I became a survivor of all my male years. As I was surviving, it's important to note I was experimenting the entire time being feminine. I studied how the cis-women around me carried themselves and reacted to the public situations the best I could. And, although I could have never gone as far as I wanted to with my experimentations, the thoughts were always there in the back of my mind. Finally I made it to a point where I could develop a plan to see if I could in reality follow my dream of living as a fulltime transgender woman. Every time I was successful trying one adventure, I was able to move on to another. I learned one way or another I wasn't the only novice transvestite or cross dresser in the world as I began to successfully navigate clothing stores and malls where I lived. When I became bored, I started to go to more challenging venues such as restaurants and test the environments there to see if I would be accepted  When that worked I began to work on my overall communication skills and again concentrated on improving my presentation which was an ongoing process.

So, in reality, I wasn't wasting any time as I attempted to live a life between both of the main binary genders. Trying to do both nearly killed me before the doors opened wide and I again could pursue my life long gender dream. Could I ever really be brave enough to leave my male past behind, along with all the privilege I had earned and live as my authentic feminine self. 

The more I lived as a transgender woman, the more I felt I was doing the right thing and began to resent the fact I didn't try earlier. Throughout the whole process, it was easy to forget the evil days when I disliked all aspects of being male. But over the years I came to realize it was all a learning experience anyhow and helped me to realize how I could lead a more complete life.

Living Your Transgender Truth

Image from Brett Jordan on Unsplash

To live your truth as a transgender person, you first have to figure out what your truth is. 

In many cases, accomplishing knowing your truth when in comes to gender is very difficult. Even though I had realized from a very early age I wanted to be a girl and strongly admired everything feminine, it was still a difficult journey until I could actually live my truth. I believe the earliest  remembrances I had of being transgender was when I discovered just dressing up as a member of the feminine gender just wasn't enough. I actually wanted more. I wanted to actually be a girl/woman. Sadly, when I was discovering all of this, there was no internet or social media so I still felt isolated from the world. It wasn't until years later when I heard the term transgender for the first time. 

As the years rolled by and I learned more and more concerning what a transgender person actually was, I increasingly felt the term described me. Primarily because I felt just cross dressing as a woman was just never going to describe me. Plus, I had for the first time encountered other persons who identified as trans and I just knew I wanted to learn more about their lives. It turned out to be the right move since two of the people in my circle made their journey's all the way to living full time as women.  Right or wrong, they both became role models. Through it all, I wondered if I could ever follow in their footsteps and live an impossible dream as a transgender woman. 

One of the main differences was neither of them were involved in a serious long term relationship with a strong woman who did not approve of a gender transition. Also employment wise there were major differences such as one of the women I knew was a fire-person and had served out her initial twenty years so she had a good pension coming. And, the other woman was a very successful electrical engineer. She knew she was in demand employment wise and would have no problems with securing employment. Also, to make matters worse for me (or better for them) they were both gorgeous. Here I was just doing my best to look the best I could while all the time knowing I would certainly lose my job and my wife if I transitioned. Living my truth during that time in my life turned out to be rather murky. I was considering following in my acquaintances footsteps but couldn't quite figure out how it was possible. 

Through it all, I took my usual male sides approach and tried to hide my truth. Predictably, the entire process was ill advised and finally led me to a very serious self harm (suicide) attempt. To save myself and live my truth, it took a series of events in my life to do do it. Sadly, the biggest was when my second wife of twenty five years passed away when she was just fifty. Her passing, along with the fact I was quickly approaching retirement age led me down the path to being able to attempt a gender trnasition. It was during this time when I began hormone replacement therapy or HRT. The hormonal change propelled me even further to learning my truth...I always should have been a woman. My body just screamed for the changes it went through and it all felt so natural.

I realized in my early sixties, destiny was on my side and finally I would be able to live my transgender truth.

One Day

Tomorrow is Liz and I's wedding day.

Photo Courtesy
Jessie Hart

Yesterday we went to the store and bought cookies and beverages for the reception which is very small as I have written about before. I think our total expenditure was only around fifty dollars. Liz already had the table clothes, plates and cups for the event which helped with the cost. 

Along the way, Liz found a wonderful useable non copy writable beautiful set of vows to read. So far the weather is even on our side promising a beautiful fall day with temperatures near seventy degrees (F). 

Speaking of beautiful, I am set to have my mane of hair trimmed and my nails done. Don't know if I will be so beautiful but it will feel wonderful to "girl-up" for a special occasion. For my wedding outfit, I have chosen my long black embroidered skirt matched with my fuzzy teal green sweater and my charcoal grey boots. I even managed to see if my long unused earrings Liz made me still fit the long unused piecing's I have in my ear lobes.  

As you can tell, simplicity is the key to the whole wedding. As well as the long lasting love we have felt for each other over the past eleven years of being together. Plus I have written before, is the fact my transgender grandchild will be at the wedding with their partner. So nice to be a role model for both of them.

Later on today, we will be journeying forth into the grocery store world to buy supplies for the week and the beginning of Liz's diet plan. It's always interesting to me after all these years to see how I am received in the public's eye. After all this time nothing really negative or exciting has happened. I can even use the shopping cart as a form of a walker to help in my getting around. 

Through it all, I still can't believe it is happening to me. I went through all those years of having no one in the middle of a gender transition. It was after the time I lost my spouse of twenty five years and I was intensely lonely. Finally I managed to fid a new group of friends who provided a social outlet as well as an example of how I could live as my authentic self. Liz was in that group of people. 

As I look back at all the dark days I spent alone somedays I think all those days were just a test to see if I deserved to transition and find another partner as I aged. 

Tomorrow will prove I could. 

It's Wedding Week

Liz on the left. New Years Eve
Photo

It is here already.  This is the week Liz and I get married. As always, time flies when you are having fun. I can't say I was having fun the entire time but I can say I can't believe the time has gone by so quickly. 

You see, Liz and I have been together for eleven years now and we actually met on an online dating site. Literally, she reached out to me when I was desperately lonely. We quickly hit it off and started to seriously correspond. First by email and then by phone when I became brave enough to let her hear my voice.

Of course one of the major factors in getting together in person was the distance we lived apart. In those days I lived approximately a hour apart. I lived in Springfield, Ohio and she in her native Cincinnati. So we were within meeting distance. Another plus was I had always loved Cincinnati and deep down thought I would end up living there. 

Following a year or so of commuting back and forth I moved my dog, cat and myself to Liz's place in Cincinnati. Without much of a problem we managed to mesh as she had her son, a dog and two cats living there. Spiritually, Liz is a Wiccan and I lean towards the Buddhist faith so again meshing wasn't too difficult. Liz was way ahead of me when she said how deeply she felt the relationship was destined to succeed and flourish.

Fast forward eleven years and Liz and I are obviously still together and thriving even though I am twelve years older the relationship continues to grow. So out of the clear blue sky a couple months ago my daughter said why don't we and get married. I thought about it for awhile and asked Liz to marry me. She said yes and we moved forward and went to the courthouse and filled out the necessary paperwork. Then we had to make a few basic decisions on what would happen next. It is Liz's first wedding and my third so I left many of the decisions up to her. The only thing I didn't really want was a big wedding and I did not need a fancy wedding dress. None of my previous wives desired a fancy dress and neither did I. Then came the names.

Since I just changed my name legally a couple years ago, I didn't want to go through all of that again. Plus I still am proud of the last name I was born with. Liz on the other hand is eventually going to take my last name. But overall, she wants to be able to call me Mrs. Hart which is quite the change for me. As far as the wedding ceremony itself goes, just my daughter's family is coming plus Liz's son. So with the officiant we will be around ten people. We do have one special guest. I have a FtM transgender grand child who is going to bring their serious partner and I am honored.

What I want everyone to know is when this all started I had exactly no expectations I would ever again be in a serious relationship. I was extremely lonely and was searching in some of the wrong places. Out of sheer persistence I finally hit pay dirt. More on that in a later post. 

Legally Complete

Dinner with Liz on the right
Jessie Hart

Yesterday, Liz and I made the big step of going to the courthouse and obtaining a marriage license following eleven years of knowing each other. No need to hurry, right? 

After walking what seemed like a mile to me to get to the courthouse, we made our way by elevator to the tenth floor where marriage licenses are done. As I waited for the process, the more nervous I became. How would the clerk perceive us and would there be a bias. At the least we would be perceived as two women getting married and at the worst I would be outed as a transgender woman marrying a cis-woman. It turned out the only major problem I was going to have was my own fault. There was a pre-certification process I had to fill out before we went to pick up and/or do the licensing process.

For one, somehow I filled out the wrong question concerning my deceased wife and they had me as divorced at the time of her death. If all of that was true (it wasn't) I would have had to come up with a divorce decree. I was able to convince the clerk I filled the form out wrong and I was definitely still married to her when she passed away. 

Once I passed that hurdle, I had to go way back in my old noggin to 1978, to my divorce from my first wife. I was able to search county records on line from my hometown and actually located the file of our disillusionment I was looking for. Ironically the hardest part of the entire process turned out to be the part I did correctly because the clerk said all my information had been accepted.

From then on, it was clear sailing as we filled out the rest of the necessary paperwork and paid out the seventy five dollar fee. By the way, no bias was shown due to our gender situation. For all the clerk knew, we were two women getting married. Just the way I wanted it. The only thing that made it difficult was my own mistakes filling out the information.

We are all set now until the official wedding date of October 16th. Liz in particular is excited for her first marriage. 

Last night we celebrated by going to our favorite Mexican restaurant to have a Margarita and talked about our past, present and most importantly our future. Somehow I have always felt two is better than one so yes I am excited about the future.    

Time Flies

Liz and I on New Years Eve

 Unfortunately for her, one of my Mom's well worn comments I never forgot  when she caught me wishing time away went something like this, "Life is like a roll of toilet paper. The closer you come to the end, the faster it goes." 

The idea of Mom's is certainly coming true for me. An example is coming up tomorrow when Liz and I go down to the courthouse to secure our marriage license. It seems not so long ago the need to go was still weeks away. Before I know it, October 16th will be here and we will be married by our officiant Josh. For all of you who may wonder what an "officiant" is, Liz and I have not decided to be married by a minister/priest in a church. Josh is recognized by the state to do weddings and file the proper paperwork. He is also the leader of Liz's coven she is part of, so we will be in good hands. 

Hopefully, since we will be in an outdoor shelter hosue, the weather will cooperate also. 

Of course, this upcoming wedding is just one example of something either I never thought would happen or would be so far into my future I wouldn't have to worry about it for awhile. The older we get, the more time becomes compressed and moves along with more purpose. Perhaps it is why we think time is flying faster than before. Also when we were younger, you had time to overcome mistakes such as gender related issues. In all too many instances (such as my own) families need to be replaced and new friends secured. 

I was so old when I transitioned (60) I was certain a new life as a transgender woman was going to be a very solitary experience. One I was prepared to make even though I was still trying to meet others on line and in the very few venues I went to. Against all odds, Liz responded to an on-line search for that special someone. Impossibly I couldn't believe it was happening to me. 

Most of you know the rest of the story, in under a month I will be seventy three and shortly after that I will be into my third marriage. My first marriage ended fairly well and she knew the entire time I was a cross dresser. Most importantly my first wife was the mother of my only child, a daughter. The best gift ever. My second wife who also had no problems with my cross dressing always drew the line at any ideas of me having a transgender future passed away unexpectedly from a massive heart attack. No way possible did I ever think there would be a Mrs. Hart that  she would be me. 

Time does really fly by as the roll of toilet paper moves faster and faster.  

A Break in the Weather

 

Image courtesy Mike Tolliver
on Unsplash

The hot and steamy non airconditioned weather I have faced for most of the summer has finally given way to lesser humidity and lower temperatures. Oddly enough the climate change has helped to give me a break from my gender dysphoria, without an influx of gender euphoria. I rarely have very many moments of inner peace but have had a few lately. Perhaps it is just the lull before the storm.

When the VA gets it scheduled my Mammogram will be coming up relatively soon I hope. Plus, I also have my latest Covid booster shot coming up at the end of the month. 

Then there is the wedding to plan for. Between now and October 16th we still have quite a bit to do. What could be interesting is when we go to the courthouse to finish and submit the legal process. My mind tells me not to fully expect a flawless afternoon. Between the usual legal trip it will be interesting to see if my transgender status plays into the process at all. My legal documents all say female so we are attempting a same sex marriage, which in the City of Cincinnati "shouldn't" be much of a problem. After we celebrate with a cocktail (or two) it will be time to move on to what sort of ring do I want and what am I going to wear. Of course, Liz already has ordered and received her outfit. No pressure on me? Right!

Also I neglected to mention I have my birthday mixed in in October and sooner more than later I will have to check back in with my VA health clinic to set up an optometrists appointment and reset several prescriptions I have which are expiring. My only problem is the clinic itself. Overall, except for my last phone call which the person referred to me as "Ms. Hart",  not many others in the clinic have been gender friendly. As I have mentioned in a previous post, I have had enough and will start taking names and reporting people. At sometime also I have to pursue their (VA) help in obtaining a handicapped parking pass which increasingly I am needing. 

I know to those of you who lead regular non retired lives this perhaps doesn't sound like much but when you throw in the sometimes unexpected responses you get when you are transgender, life can become a little dicey. I am so fortunate to have such a "gender warrior" such as Liz by my side when the going could get a bit tough. She is quick to step in and correct the occasional person who refers to me with a male pronoun. 

In the meantime I have started up my walks again to attempt to build up my much needed physical stamina and will continue them as long as I can weather permitting.   

And the Process Begins

 

Liz on left and I. Photo courtesy Jessie 
Hart

After nearly eleven years, my partner Liz and I have decided to "tie the knot" and get married. No need to hurry, right? 

This morning I was able to fill out the necessary paperwork forms on line here in Cincinnati. 

Overall, we are looking to have a very small wedding in October with Josh our "officiant" my daughter and anyone who wants to come from her family plus her son AJ.

This will actually be my  third marriage and none of the others were really fancy affairs. On the other hand, it is Liz's first marriage so I am leaving the planning up to her. At this time I don't anticipate donning a fancy white wedding dress for a number of reasons. For one white should be out because I am far from a virgin. Secondly I can't see spending the money on a dress I would only wear once and finally none of my other weddings were "dress up" affairs so there is no reason for this one to be either. 

There are several other decisions we have had to make ahead of time. One of which was one of us who would naturally migrate towards the wife's role and that would be me. So you could say Liz put a ring on it after eleven years. The second major decision was who was going to change names (if either). To make things easier on me, Liz has agreed to take on my last name. 

I am sure as we grow closer to the actual marriage date there will be other hurdles to jump. In the meantime I am going to try to enjoy this latest chapter to my life. 

Equal Time

 Recently I have been writing several posts concerning the interaction between my Halloween adventures and the interactions with my wives (at separate times.)

First of all I had experience with two wives for the stories. The first was much more accepting than the second but both knew about my cross dressing urges before we became married. The problem became more prevalent  as I slipped further and further into the realization I was much more than a cross dresser. I wanted to follow the natural urges I was feeling to shove my male self into the closet and live full time as my authentic self. 

My second wife used the well worn phrase, she didn't sign up to be in a relationship with another woman. Plus, a few other phrases I will save for another post. 

What happens to the spouse when that happens? Back in the day, I used to take a look at a few blogs which dealt with women who were immersed in relationships with their husbands who suddenly told them they were transgender. Needless to say, the reactions I read from the wives were not positive. Even I was shocked. 

I think what we all miss during our Mtf transitions is that cis women have egos also. In many cases a husband figures prominently into her ego. Or, what she did wrong to "drive" her husband into the feminine camp. 

As far as I am concerned, I don't know how I would feel if the shoe was on the other foot and my spouse wanted to complete the difficult journey to another gender. I just know it would be very difficult. 

I can understand too how a transgender path could be considered the ultimate in being selfish. After all it is an all encompassing desire to make it to the other side of the gender divide. What happens to a families life, jobs and kids when it happens?  It's so difficult to help another person to understand there is really no choice when you are considering crossing the gender frontier. It is so much more than just dressing as part of the opposite gender. It is life or death. 

So, my heart goes out to all the understanding spouses I have been reading about recently. Or even the ones who begrudgingly have come to accept and stay with with their former husbands or wives. Of course the internet has helped with all of that. Positive information abounds on how couples in love have survived their gender journey together. 

Taking my local scene as an example. the transgender - cross dresser support group I am part of has recently featured several couples who are successfully staying together. As I wrote, all my positive thoughts go out to the spouses who made it happen.

Equal time! Good job!