Creating a Tangled Gender Web

Image from Robert 
Anasch on UnSplash

When I look back at my life, I wonder if I knew all it would entail would I do it all again.

The only change I would make would be to have have the courage sooner to go ahead and transition from male to female. Even though it sounds like a good idea to have jumped off my gender cliff earlier, the problem became the world around me. I am seventy four and the world at large has gone through several different realities when it comes to the transgender world. Back in the day, there was very little feedback when it came to being transgender at all. Basically, there were only two categories, transvestite (or cross dresser) and/or transsexual. Neither of which felt very natural to me, Plus if you went the transsexual route, you were expected to move and leave your old life completely behind. I never thought I could do it either. I still had a daughter I loved plus enjoyed small parts of my male life.

In other words, I was stubborn to the point I thought I could still transition my own way. If indeed I ever came to the conclusion I was trans. As I procrastinated through life, I created an increasingly tangled gender web. I was trying to balance what was left of my male life along with a long term marriage with a woman I loved very much. At that point, I was trying my best to try to discover my true gender self. My web grew ever tangled the more I tried to either escape or relax and enjoy the ride. The ride included taking my transition one step at a time. I found as I struggled in my tangled web I needed more than one transition to move forward. It took the evening when I finally decided to go out to be a transgender woman rather than as a very serious cross dresser just out to escape my male world. to change my mind The difference was major in that I was striving to discover who I really was rather than just playing some sort of game I had indulged in for most of my life. Much of it was in front of a mirror. Naturally the world was much more brutal and I needed to be better.

As it turned out, I was increasingly successful in both of my lives in the main two binary genders which caused my web to be even bigger and more tangled. I ended up sneaking out behind my wife's back, which caused severe problems with my marriage. It was increasingly evident I was stuck in a battle between two women. My wife and my inner woman were both strong feminine people and the war weighed heavily on my overall mental health. Before it killed me, I needed to finally escape the tangled web I was in and begin to live as a woman. Or, as my wife told me, be man enough to be a woman. 

Once I escaped, and with the help of several key friends, I was able to start all over in a new feminine  life. Although, once I began the life, I understood the fact my new life wasn't so new after all. My inner self had been waiting and observing my life just waiting to take over. Of course after I escaped the web, she had her chance and I was living my dream life.  At the least I never led a boring life. 

   

Ode to Halloween

 

Halloween image from
the Jessie Hart Archive (Tom on
Left)

I have lived long enough to experience Halloween coming full circle.

Early in life I experienced the urge to wear a feminine costume but never had the courage to break out of my gender closet and do it. Plus I lived in such a small rural area, there weren't too many kids to go around and once you were pigeon holed into a certain category with your peer group you couldn't get out.  Examples included friends who were good or bad students as well as those who were always the outstanding athletes in the class. There was never any space for a stray boy who wanted to be a girl.

So I had a deeper reason never, ever express my feminine longings at all on Halloween. On top of all of that, I never saw any other boys who were dressed as girls. No cheerleaders, princesses or any of the stereotypes from the female world. The only time I can remember ever seeing a fellow male in drag or cross dressed was for selected festivals in high school. I was amazed at their male to female transformation. Plus I did hear the gossip concerning another guy in school I didn't really know who was dressed in his sister's clothes for his "costume" as the rumor went. I was so envious!

Once the years progressed and I naturally achieved more freedom to be my own person, I was able to pursue more courageous goals as far as Halloween went. I tentatively used the holiday to sneak out of my closet and explore. Could I dare make it in public as my feminine self. Very early I learned lessons I could take with me for years as I transitioned. I found if I dressed more conservatively at Halloween I indeed could have a chance to present well in the public's eye as a woman. As it turned out, all of this would be just the beginning of what I could learn on my ever rocky gender journey. 

Halloween made it possible for me to understand I could indeed live a life as my authentic feminine self. The only real problem came when I could only experience my terrifying yet exciting new life once a year. I was increasingly forced into the real world to learn my new gender lessons. All of which were made possible by Halloween.

Ironically, the more I learned from my initial experiences, the more I found the lessons would serve me well when I transitioned into a world ran primarily by women. If I could get other women to accept me, the better and easier I would have it. I also learned the hard way the process I would need to go through with men to attempt acceptance. Along the way, when I learned the better I presented at Halloween parties as a woman, the more of my male privileges were lost. Almost instantly, my old male friends began to leave me alone with the rest of the women. 

These days I have gone full circle with Halloween. It has served it's purpose of launching my journey down a path to be a full time transgender woman. So I don't have any need to go to any parties with elaborate costumes. I have done all of that and it is time to sit back and recognize Halloween for all the amazing experiences I was provided.

Looking back...Again

Image from the 
Jessie Hart Archives

Rumor has it October is my birthday month and this year I am coming as close as I can  to being seventy five years old without actually being there.

As I am not really in the habit of celebrating anything but my milestone birthdays, so this year is not really in that category, yet. 

Even still this year for my birthday I find myself looking back at how I lived my life, good and bad. As I reminisce, the first thing I always encounter is how long I waited to let the world in to my true self. In other words was waiting until my early sixties until I came out to the world as a transgender woman. The time just felt right for me for several different reasons. The first being my life as a three days a week cross dresser just wasn't cutting it and I was becoming increasingly frustrated with attempting to live a life between two of the main binary genders. I felt as if I was being completely torn apart when I did it. 

I also felt as if I had taken my unwanted male existence and made the best of it for as long as I could and it was time to let it all go. During my male life I had achieved such milestones as fathering a child, completing an education, serving in the military and holding down a good job. And, maybe most importantly, my body had given me a healthy life to work with. To this day, the only operation I have undergone was having my tonsils removed. Most certainly, good health is the key to a good life. 

Perhaps, as I look back, I was a user when it came to my male life and a taker when I transitioned into a feminine world. When I made it into my sixties, I had used up most all of the male privilege life had to offer and it was time for a change. If you want to fault me for feeling this way, I plead guilty as I played the best I could the gender cards I was played. During my life, on occasion, I did gamble on moving and job changes to advance my male life, what I didn't gamble on was when I decided to complete my male to female gender transition. What I did do was explore every facet of the possibility I could live my dream and exist as my feminine self. I went out into many areas of the world to see how I was accepted and in most cases came back with a positive response.

Also, I know in some circles, waiting so long to trnasition makes me less transgender than others consider themselves to be.  I can only say, the past I lived and survived in was a different world than the one today.  Plus, I can care less what anybody says about me except my wife and daughter. With the outside world bringing all the pressure on the trans community politically, it is time to put petty differences behind us and go forward together. 

Perhaps the benefit of age can give us a better look around and not focus on the red hatted crazies who still support a former president.  But on a positive note, it is always good to put another year behind me and always hope for better in the year to come. 

The Power of Pain

Image from the 
Jessie Hart Archives

 Perhaps you have heard of the expression "What doesn't kill you will only make you stronger". Most certainly it is easy to equate the quote with being transgender. 

As we go through life as a trans woman or trans man, our upbringing follows us. If you suffer from gender dysphoria as I did, or not, very few of us escape the torment of our lifetime of taking a long gender journey. A journey which presents new challenges at every turn. First of all, we have to deal with the challenge of perfecting our appearance so we can attempt to go out in public at all, As I write about often, I went through severe challenges before I learned the hard way I needed to dress myself to blend rather than excite. 

Once I learned those hard lessons, I was able to move on to even more challenging moments in my male to female gender transition. The pain I was experiencing led me rather quickly to another big fork in the road when it came to living in a woman's world. What I needed to learn to be able to play in the girl's sandbox was to be able to understand how women communicated between themselves. I needed to adjust to living in a largely passive aggressive system in order to survive and even flourish. Also, I needed to learn what women were really trying to say when I was attempting to make it successfully in a system they were good at and I was still a novice trying to learn. 

Many times I didn't escape the pain when I was backstabbed or clawed in the back by another woman I thought accepted me. It wasn't until I found a small group of women friends who accepted me for who I really was and didn't use it against me. At the same time I learned from my friends the basics of learning to validate myself without a man and more precisely accept myself on my own terms. Sadly I still had my own share of pain. Then I experienced even more pain when I entered  the dark time of my life. Somehow it seemed I had to lose nearly everything else to gain my time to emerge as my true self. Truly a time of intense rediscovery and finally I was able to move on regardless of the pain I felt. I needed to take the difficult step to learning to trust myself again as a totally new person in the world.

Looking back at the painful dark portion of my life, I think I very much was able to emerge as a better person.  The biggest positive was I had the opportunity to live as a functioning member of both of the two binary genders. In fact, for awhile I found myself advising other women on communication problems they were having with their men. I was humbled and flattered to be included in their thoughts but still thought there was better advice to be had than mine. 

I guess, in the end result ,pain is what you make of it. Very few humans escape real pain as it is built into our lives anyhow as we all experience death. However it seems, being transgender brings even more pain to lives which don't deserve it. It is one of the reasons our trans selves have molded ourselves into such a resilient tribe.

As the Seasons Change

R.I.P Jimmy Buffett

As the calendar changes to September, around here in Southwestern Ohio, thoughts turn to the arrival of the Fall season.  Around here, Fall is finicky because it arrives in stages, It comes, goes and teases us before finally arriving for good with a vibrant display of colorful foliage in October. 

I have always been fond of the Fall. To me it meant the return of  warm fuzzy sweaters, leggings and boots. Plus, it means the return of football season which brings back many fond memories. I was fortunate my love of sports spilled over in many positive ways into relationships with all of my wives. Since I had developed my sports passions as a way to hide my true gender desires when I was younger, I was nearly panicked when I transitioned into a transgender woman and wondered how I would fill the sporting void.

Fortunately, I didn't have to worry long. I fairly quickly ran into other women who shared my passion and knowledge of sports. I have many great memories when I was able to gather with them and enjoy sports over a large draft beer. Something I would have considered impossible when I began to consider my male to female transition not so long before. The whole process enabled me to bring a huge part of my personal baggage with me into a new world.  Making my world more enjoyable was being able to enjoy the weather and the fashions of the season.

Before I did it, I needed to go through my wardrobe and add or subtract any necessary items. The whole process brought into focus one of the most enjoyable pastimes I craved when I transitioned. I had always been so envious of the women who were able to change their wardrobe with the seasons. Out went the old clothing boredom which came with men's clothing in came colors and vibrant change.  In fact, I have just started my process of wardrobe evaluation, and have began to plan for replacements. After looking, I know I better begin the process of shopping for more sweaters before the good selections are picked over. 

Over the years, I came to recognize the Fall with the good as well as the bad when it came to my existence. The change of the Summer foliage dying off represented the possible change of my old male self dying off. I remember vividly one night when I was driving all alone and shed a tear when I saw the dried brown leaves blowing across the road in front of me. I so badly wanted my life to change also but little did I know it would be years before it would. Speaking of changes, my blog gently weeps today when I learned of the passing of musician Jimmy Buffett. One of Buffett's biggest concerts every year was here in Cincinnati. It was one of the must see traditions for my second wife and I every summer. My passion for Jimmy began when I won the corporate front row tickets from the company I worked for at the time. His music always resonated with me and I am so sad to learn of his passing. Rest in Power!

The one good thing about a musician, their music has the potential to last forever.  

It's all In the Preparation

 

Anniversary Selfie from the
Jessie Hart Archives

Anyway you slice it, crossing the gender border to your authentic self is a huge task which takes a ton of work.

First of all you have to attempt to solve the problem of securing and applying makeup and clothes.  When I started I couldn't even paint my model cars well let alone my face. More times than not I ended up looking like a clown. It took me so long to be able to take my own meager funds and then sneak out to a store to buy my own cosmetics. The whole process was one of the scariest moments of my young life. To this day, I don't know how I pulled it off with my Dad working just  a block down the street. But I did and managed to learn the preparation needed to much later on leave my closet and join the world as a transgender woman. Of course with my wardrobe, again the same was true. I needed to mix and match whatever clothing items I could to do the best I could until I could afford to do better.

Perhaps two of the most beneficial things I did to further my transition was to take care of my skin and lose weight. Little did I realize, when I completed my daily hated shaving, I was actually helping my outward appearance, including when I applied a moisturizer when I did it. I am a believer it all helped when I began my hormone replacement therapy and my skin started to naturally soften anyhow. It was similar to going through puberty again. Just reversed from when I did I as a male growing up. The harsh, hated angles I acquired started to soften which made it so much easier for me to present to the world as a transgender woman.

The other main thing I did to further my male to female gender transition was to lose weight. In fact, I was able to lose nearly fifty pounds when I began to seriously attempt to the public's eye and begin to seriously go out. Of course it made finding and wearing fashionable clothes easer to find. It turned out, it was all in the preparation as I shopped for just the right accessory to go with just the right outfit. Fairly quickly, I faced the problem of over dressing the other women around me and needed to be careful if I wanted to blend in and not cause too much attention to me. Because, even with losing the weight, I still was a fairly large bodied woman and needed to do my best to present around the fact I had been subjected to testosterone poisoning in my past. 

Through it all, I learned again what I already knew. Being a woman meant joining the high maintenance gender and everything I thought I knew about being feminine had to be re-learned. A fact my second wife tried to tell me when what was left of my stubborn male ego wouldn't listen to her. When she told me I made a terrible woman, she wasn't talking about my appearance. Which turned out to be very difficult in one sense yet was the easiest  part of my transition in another. 

Often I wonder what it would have been like if I had had the opportunity to grow up as my chosen gender. To have had the peer pressure to look and act a certain way. More than likely, the grass would not have been as green as I think it would have been. Mainly because I think my Mom would have put increased pressure on me to conform to her world. Whatever the case, I think preparation would have been the key. Having more of it at an early age would have certainly helped.

In It to Win...A Transgender Life

 

Self Photo from the Jessie
Hart Collection

Once I seriously started to go down the gender path to a total transgender transition, I just had to be in it to win it. 

The question remained what the process would be to win it. Along the way, I had already suffered from (and conquered) a deep sense of feeling selfish. Once I did I made it to the level of impostor syndrome. First, let's deal with all the selfishness I felt as I transitioned. Many of my feelings came from knowing I was nearly single handling wrecking a male life I didn't want anymore. Most importantly it meant destroying a twenty five year relationship I had with a woman I deeply loved but she was completely against living with another woman. I was stuck between the rock and the hard place with no where to go. Life became hell. 

Perhaps the worst part was knowing I was being selfish. Every time I withdrew into my feminine self to escape the world was time I could have spent to make the relationship stronger. Finally, I needed to realize my pursuit to my version of womanhood was selfish and had to be if I was ever going to be successful. Also I needed to define success and what it meant to me. Increasingly, what success meant to me was to feel so natural as a woman. Deep down inside, I knew I was doing the right thing, no matter how selfish it was to do it. I was certainly in it to win it.  But winning it turned out to be far from easy. To be successful, I chose what I referred to as the "stair-step" method of gender transition. Or once I had conquered one step, I could try another. The first example would be when I began to just have confidence in my appearance when I left the house. From there, my basic confidence increased and I advanced to the point where I could navigate the world fairly easily as a transgender woman. 

It was about this time when "impostor syndrome" set in for me. Here I was out in the world and all of a sudden the feeling I was some sort of a secret invader came along to ruin everything for me. To be in it to win it, something else was coming along just to be another obstacle. Finally I was able to conquer impostor syndrome by accepting the woman I was becoming was a part of me all along. I had just become a woman by taking a different path than most cis-women I knew.   Most importantly I learned I could be a winner and achieve my goal.

Ironically, all our transgender lives are so similar yet so unique. Sadly most of us go through  similar bouts of selfishness and/or impostor syndrome and we transition into our authentic gender selves. We all have to succeed in our own ways to be survivors in an ever increasing challenging world.

The Levels of Transition

 

Photo Courtesy Parris
Freeman on UnSplash

Over the years I slowly came to the realization there were many levels of a gender transition. As I climbed walls during my journey, I was seemingly stuck forever in a gender maze. Often my frustration reached crisis levels as I tried to live as my authentic self. Every time I thought I had conquered a wall or turned a corner, another wall appeared. On the days when I was out exploring the world as my feminine self for the first time I thought I was looking my best only to have my walk or talk give me away. I even went as far as practicing my walk when I was cross dressed as a man late nights in big box stores. I am sure more than a couple store detectives were amused when and if they caught me on store cameras. It took me years to try to put my male past behind me and move forward. 

Finally it occurred to me I was doing something all wrong. Through my gender haze I was neglecting to realize I was escaping one closet into another I would have to transition out of. This realization led me to the evening at a well known casual dining/bar venue when I decided I was going to try to blend in with the mall worker women who came in after their shifts. For the evening I chose my favorite outfit. A black pants suit which was dressy to a point without becoming overwhelming. I decided to wear my favorite matching black flats and shoulder length blond wig. Climbing this wall in flats was terrifying and I ended up sitting outside the venue for a half an hour before I gathered my courage to go in.

Once I was situated at the bar and was able to breathe again, I knew my life had changed and I could never go back to being a closeted cross dresser. I felt so natural! Plus more importantly I had the chance to climb my latest wall and see a portion of what could lie ahead in my life. In the dim distance I actually could see myself actually transitioning again into a transgender woman. The more I considered it, the more complex the idea became. At the time I was still married to my second wife who never approved of any idea of taking hormone replacement therapy and living more and more as a transgender woman. She said she never signed up to live with another woman. Of course there were many other problems to consider such as having a job and losing friends and family. All of these walls to climb became unbearable at times and I resorted to trying to bottle up all my emotions along with hitting the bottle (alcohol) way too much.

What happened was all of the sudden my life was to change drastically as I went into a very dark period. I was knocked for a loop when I lost three very close friends to cancer and my second wife to a heart attack. The only good thing that happened was all of a sudden the dark clouds parted and my path to transitioning to a transgender woman appeared. During this time was even when the Veterans Administration approved using HRT for gender dysphoric veterans. Since I was already in the VA health care system, taking advantage of the program wasn't too difficult and helped me to afford the treatment. 

Years later after I transitioned into living a full time life as a transgender woman, I considered I would never  encounter many more walls to climb. But now I face the greatest transition of all. The final crossing from this life to whatever may or may not lie ahead. Plus what will happen to me during my final days if I end up in an assisted living facility or nursing home. These days I have steeled myself to jumping off that bridge when I come to it. 

So all in all, transgender women and trans men don't have it so different than anyone else who lives a long life. There are built in transitions to consider. We trans and LGBTQ folk just have more to consider.

The Mean Streets

 

Photo by Annie Spratt on Unsplash

When you get down to it, many streets or parking lots just aren't safe for women. All women, cis  or transgender. Yesterday when I was going back to my parking lot alone, I keenly felt the pressure of walking two blocks down an urban street alone. To my benefit, the time I was doing it was just before dusk so there was still plenty of light. Along the way I began to wonder why I didn't see (or notice) any uniformed police presence. Usually, the Cincinnati Police has an LGBT Outreach unit they send. Perhaps they decided to be present at the Transgender flag raising ceremony the same morning at City Hall.  One thing is for sure, I noticed nearly no one during my walk.

I don't move so well anymore so I couldn't move quickly if I had an incident. 

My paranoia proved to be just that and I made it to my car without an incident. There was a time years ago when I didn't. I was still very much a novice when it came to being in a feminine world. I still didn't realize how much of my male privilege I was giving up as I transitioned to a transgender woman. One of the biggest was my personal safety. No longer could I ignore parking in poorly lit parking lots or streets and it came back to haunt me in the worst way.

One night (late) I was coming out of one gay venue in downtown Dayton, Ohio I used to visit on occasion. When I left I was confronted on the sidewalk by two guys wanting money. Luckily I was able to defuse the situation by giving them my last five dollar bill and they let me go on my way. From then on whenever I went back there I made sure I was not alone. I remember vividly the first time I asked a trans man I knew to escort me to my car one night when I left a big gay club. Lesson learned which was reinforced on the night I have written so much about when I was physically threatened by a man at a party I attended. 

As I wrote, none of this is new to a cis gender woman. They grow up living in a world where they are in physical danger at some point in their lives.  One of the most important lessons you need to learn as you begin to navigate the "mean streets." 

None of this is meant to make you paranoid.  It is meant as a gender warning. Just as if you have faced a point in your MtF gender transition when you were treated as a second class citizen , potentially losing your personal security is even worse. 

As many cis women will tell you, welcome to their world. If you are careful, you can negotiate the mean streets just fine as your authentic self. Just don't make the mistake of thinking you can bully your way out of it. Plus, I know some transwomen who carry firearms to protect themselves. Even with my Army weapons training, if I did, I am afraid I would shoot myself before anyone else. Instead I choose to not be alone on the mean streets if I can help it. I am fortunate in I usually am with Liz who is very familiar with Cincinnati and knows where to go and where to stay away from. 

As they used to say on the old "Hill Street Blues" police show, let's be careful out there!