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. 

   

Testosterone Challenged

Image from the Jessie
Hart Archives

Recently it was time to take our car into the shop for an oil change. When I learned I needed to accomplish such a simple task on my own (with no help from my wife Liz), my anxiety level began to rise up. 

All my anxiety stems from my early upbringing when I was struggling to find my footing at all as a male type person. On a fairly regular basis, my brother and I would accompany my Dad when he visited his best friend who happened to own and operate a auto salvage yard. For better or worse, my brother and I got to see so-called pet alligators all the way to dynamiting ponds and salvaging the fish which floated to the top. to eat.

On occasion, the experiences were fun but at other times I was wondering how I could ever break out of my well hidden feminine tendencies and be a man in the mold of my Dad who was in many ways a man who fit the stereotype of a self made man. He rose from struggling through the depression to become vice president of a bank and building his own house. I never came out to him during his life. I forever grew up in his shadow and always experienced huge doses of anxiety when I needed to participate in any male-centric activities. Which included going to any sort of auto parts stores. 

Which brings me back to my oil change experience. My basic problem was I thought I could have been taken advantage of since I am a transgender woman. 

The staff at the place was predictably all male and the testosterone level was very high and yes I was intimidated but I survived. It turned out the only major questions I needed to answer or respond to were how to open the hood, turn on the lights and operate the turn signals. Outside of not knowing where the hood opener was, I didn't have any major problems. Very soon, they were finished and I was on my way. No worse for wear from the extra testosterone I had to experience.  As with anything else, the build up to the event itself was much worse than going through it. I have a colonoscopy coming up in approximately one week and I know the build up would be much worse than the procedure itself. The biggest problem I had the last time I went through it was being miss-gendered by the staff. Hopefully by this time the staff will be more progressive and I won't have to put up with that this time.

Since the staff who dealt with me last time was all female, I hope they recognize my testosterone level is as low as theirs and my appearance is only damaged by an unwanted male puberty I went through.  Plus as I look at it now, the biggest problem I may face is having another sizeable polyp which would have to be removed and I receive a clean bill of health. Health, after all is everything and miss-gendering is ignorance. 

Through it all, I am sure my testosterone didn't increase and I survived my anxiety level went back to normal so I am satisfied.   

Arrival

Image from the Jessie Hart
Archives circa 2010

The beginning of 2024 has given me the opportunity to look back at the years of my life when I became very serious about the reality of entering the feminine world and living as a transgender woman fulltime. This post my give you some sort of an idea of the time sequence I went through in my lengthy gender transition. 

The year was 2010 and three years had passed after my second wife had died. In those three years, I had a brief fling with another single woman as my old male self. Predictably the relationship didn't last and we both moved on. Not before she stood me up on a summer in the park outdoor concert I invited her to. Not to worry, I dressed in my best concert clothes and took my inner female instead. I ended up learning quite a bit and enjoyed myself immensely. Until my wife Liz came along, I was certainly my own best friend. 

As it turned out, 2010 also was the year I decided to go down the road of gender affirming hormones as I sought to change my outward appearance as much as possible. Little did I know, how much the hormones would change my internal life also. It seemed as much as my emotional outlook changed, my entire view of the world softened as my testosterone "edge" disappeared. To highlight my trip down the new road in my life, my first dosage of the new hormones came that year when Liz joined me for a special evening as we were out celebrating New Years Eve.

Even though I had officially started this new path in my life, I found I still had a long way to go. Arriving meant I needed to do more than take gender affirming hormones and feel the part. Then, more than ever, I needed to walk the walk and talk the talk of being a full fledged transgender woman. Meeting the world one on one proved to be both exciting and terrifying as I needed to give up all the male privileges I had fought so long to earn over the years. I learned quickly how I would be barred from any future benefits of being in the men's club. Plus, at the same time. I needed to quickly understand all the responsibilities of being allowed in the women's club. Early on, it took me awhile to see any real benefits from being a trans woman except for the occasional man who would open a door for me.

In the meantime, arrival also meant having to learn things such as a whole new way of just using the restroom. No longer was just peeing taken to such a high level of etiquette. I needed to train myself to look other women in the eye and smile when I used the woman's room and be certain to always stop and check my makeup plus wash my hands no matter how threatened I felt. All of this was just a start.

In essence, arriving also meant being able to relax and enjoy myself in public as my authentic self for the first time in my life. So 2010 was a landmark year for me but at the same time was just the beginning. 

When I was stuck so many years as a closeted cross dresser, little did I know how bright and exciting the world would become as I started to arrive.

 

New Years

 

Image from Joshua
Kettle on UnSplash

It doesn't seem possible but it is time once again to look at a year behind us and look forward to another. As my Mom used to say, life is similar to a roll of toilet paper. The closer it comes to the end, the faster it goes. Very philosophical of Mom to be sure.

In my younger years I used to use a lot of alcohol to celebrate the coming of a New Year. The process didn't really amount to much other than a tequila or Mescal fueled evening of misadventures. One will forever be ingrained in my mind when I kissed my future sister in law before I kissed my future wife when the New Year began. Not to worry, my wife got even with me for years after the huge mistake I made. 

Of course the biggest problem I always had was trying to drink away my gender problems at the beginning of a New Year. Each year I wondered deep down if the year coming up would see me finally being able to live my gender truth and cast aside the shackles I had always felt living as woman cross dressed as a man. 

Eventually, it turned out all the grand predictions I made on New Years the year to come was finally going to be the one when I would explore all the changes I would need to make to transition into a transgender woman. Would I ever have the courage to do it. 

The whole process in many ways snuck up on me. Even though I stayed the course, good or bad as I kept exploring my options and I almost waited too long. The self destructive behavior I indulged in many times almost killed me. The end result was my resolutions to change my authentic self would finally come true. 

Now my party days are behind me and I will spend New Years with Liz from the comfort of my couch hoping nothing crazy happens when the ball goes down in  New York's Times Square. No matter where you are in your life journey, may you spend the New Year enjoying new beginnings which lead to a more fulfilling life.

Happy New Years! Thanks for stopping by Cyrsti's Condo over the past year. You make the whole effort worthwhile. 

The Home I Don't Live In

Image from Daiga Ellaby
on UnSplash

It certainly took me awhile but I finally learned my male self was simply an empty shell I existed in to get me by in the world.

Over the years, even though it was difficult, he managed to secure a spot in the world and earn his white male privileges. Participation in such male dominated activities such as sports and muscle cars led the public at large off the beaten track of who I really was. I was a cross dresser or a woman pretending to be a man. Along the way, I was still able to build a fairly strong home I didn't live in.

Around that time, my life in an an empty house became predictably lonely, even though I was doing all the traditional male activities. I was married, had a child and served my time in the Army to add to two college degrees. It seemed the more I tried to do, the less fulfilled I felt with my life. It wasn't until years later when I understood much of my frenetic pace in life had to do with my gender desires being off center. In essence, I was building a home I couldn't live in. 

In it's place, I was increasingly becoming more and more serious about discovering if I could actually pursue a dream of living as a transgender woman. What I was doing was observing others in the trans community who were moving towards living fulltime feminine lives. I wondered if they could do it, why couldn't I? I was learning consistently by going to small mixer/parties in nearby Columbus, Ohio. The get together was hosted by a soon to be retired firefighter who restored an old house in a well known restoration district. I was extremely interested in her path because she was going against all the so called "rules" back in those days. Back then it was expected when one fully transitioned into being a trans woman, she was expected to leave her old life behind and start all over again. The woman I knew was going to not do any of that and I dreamed of doing it also. The same as her. Plus her parties included a diverse group, including the occasional lesbian and I learned early of the attraction I felt for lesbians' and vice versa.

Even though I did manage to slightly follow in her footsteps, leaving the male house I built proved to be anything but easy for me. To arrive at my destination, I would have endure intense moments of pain and suffering. As my old male self finally crumbled, I would be remiss, if I didn't mention the group of friends I found to help me build a new house. This time the correct one, complete with a life in my chosen gender. 

Even though the challenge was there to build my new house the correct way, I still needed to make sure all the improvements were built in to further make my new life more pleasurable. Out went the old male clothes and in came women's clothes including shoes, wigs, and makeup. 

The end result was, I discovered I could indeed build a brand new gender house and redirect the rest of my life living in it. The home I didn't live in was long gone and I felt a freedom I never thought I would ever have again in my life. 

Sizing Up the Crowd

 

Image from Uwe Conrad 
on UnSplash

One of the earliest lessons I learned when I first began to attempt to present as a realistic woman in the world was how I was always on stage. It presented a problem since I had always been very shy around people.

It didn't matter because both men and primarily women sometimes went out of their way to size me up. Plus, while I am on the subject, I was very insecure about my size as a novice cross dresser or highly questioning transgender woman. Initially I made the mistake of walking slightly hunched over to hide the fact I was nearly six foot tall. Then I realized there were plenty of other cisgender women around me and I could stand up tall and project confidence to the world. I learned the hard way that people were similar to sharks and could sense another person's insecurities so I needed to do better in all aspects of my presentation as a trans woman. 

One of the key insights I learned quickly was quite naturally, the world I was trying to enter was run by women. So I needed to figure out how to effectively play in their sandbox. On the other hand, men were out since they had a tendency to ignore me anyhow. If a man did pay attention to me, he would normally treat me as a lesser individual. When men paused to size me up, my reaction was to quickly keep moving. I did have a few very rare interactions with men but didn't feel particularly secure with the experiences. 

Women were a different story. When I started my male to female gender transition I received more attention from women than I ever had as a man. As I soaked in the attention, I thought most of the women were just curious of why I was in their world and became amused when I needed to encounter the everyday issues they did in a feminine world. Such as personal security, hot flashes etc.. They would  simply smile and say welcome to their world. Little did they know how badly I wanted to be in their world. Being included in a group of women helped me not to be singled out for attention. When the group I was in was sized up, I was simply part of the group and not an individual. 

The group of women I was a part of just happened to be lesbians so I faced a unique situation when it came to what sort of crowd was sizing me up. On several occasions we would attend lesbian mixers, so blending in met a nice pair of jeans, top and in season boots in the winter. In terms of the society I was trying to fit in with was I attempting to present as an attractive lipstick lesbian. I was successful on occasion attracting super butch lesbians and in fact, one of my first dinner dates I had with a man was  a trans man. We stayed in touch and often he made fun of me for being scared to death on our date. Which I was!

Scared or not, over time I became experienced in sizing up the crowd and bracing myself for the impact I would make. Somedays I receive little or no response to my public appearances. When nobody seems to notice me I know I sized up the crowd and won my gender struggle. Other times, when the room I am in goes silent and I am stared at, I know I wasn't so successful. At this point in my life, I am used to all sorts of reactions, so I can move on quite easily. 

Even still, I am aware of the public crowds I face and do my best to size them up and react appropriately. No longer am I so shy.

Interruptions

 

Image from the
Jessie Hart archives. 

As I was seriously pursuing a life as a fulltime transgender woman the interruptions I went through made life very difficult.  

What happened was I was still attempting to live life as a man and a woman, I found I favored one gender over the other. The gender I favored of course was my feminine side. When I was out in the public's eye, I felt so natural and so alive. As I continued down my path, I became obsessed with improving my presentation as a woman. I had so far to go to try to perfect moving as a woman, not to mention any new communication skills I would need to get by. I was able to work on all of my gender issues approximately three days a week before I needed to revert to my old relatively macho male self. 

The problem immediately arose when I was forced to go back to my ingrained male ways or all the male type walking and talking guys do to survive. In order to be successful again as a guy, my path to femininity was interrupted and I felt as if sometimes I needed to begin all over again when I switched back to my newly preferred gender. When I did, I had to work harder to maintain what I had earned previously. Working harder allows me to explain more in depth a recent post I wrote here in Cyrsti's Condo called  "Trying too Hard." From the post I received several comments (thanks!) alluding to the fact I somehow mentioned working too hard to be a presentable transgender woman was not something we all go through as trans women. What I really believe is we have to work much harder than the average cisgender woman to earn our way in the world. Among other things, we trans women didn't benefit from growing up feminine. With no feedback on how we looked or how we acted. 

Of course too, all the interruptions I experienced on my gender journey just became worse the more I attempted to do to follow my path. It was so frustrating when I was mentally celebrating the evenings when I felt I looked and was able to act correctly as the person I increasingly wanted to be. Those were the evenings I felt my entire image worked. My makeup, hair, clothes all were on point and I was able to walk in my heels without falling or looking like a linebacker. Sadly, the next morning I would need to make sure I had removed all my makeup and had gone back to walking as a man. It was tough on my fragile mental health as I felt like a juggler trying to keep all my balls in the air. (No pun intended). 

Somehow, someway, I made it through this toxic time of my life. Ultimately, I used all the internal frustrations I was experiencing as motivation to move on. 

Moving on became a theme in my life for once I didn't use the theme to escape, I used it to move myself forward into a new gender world I had only dreamed of. Finally free of all interruptions.

She Wouldn't Share

 

Photo from the
Jessie Hart Archives

As I was progressing down my increasingly exciting gender path it became clear to me I was heading straight to a crossroad which would require tons of thought and effort.

The main problem I had was my two binary genders (male and female) were constantly fighting with each other for dominance. I attempted to satisfy both of them, plus keep my unaccepting second wife away and maintain my sanity. What I was trying to do was live three days a week as a woman and maintain my male dominated job as well as convince my wife I wasn't doing more than we agreed to when I was a cross dresser. To make it clear, my wife never wanted me to progress any further in my life into a feminine lifestyle.

The problem became evident when I became more and more successful in most all of my feminine pursuits as it became clearer and clearer to me indeed I was transgender. In the process, I wasn't doing myself any favors as the gender ripping and tearing I was experiencing made life unbearable for me. I just couldn't easily shift gears when I needed to switch from feminine to masculine in a days notice. I caught myself doing feminine things when I was supposed to be a macho guy and vice versa. When I was trying my best to be a convincing woman I needed to not walk like a man or wear a male scowl on my face. As you can understand, the pressure I was experiencing was tremendous and it dominated all of my thought when I wasn't out attempting to see if I could indeed succeed in my dream to be a woman. Trans or not. 

As it turned out, my feminine self did not want to share me with my old male person. Plus, she was ready to do battle with my equally as strong willed second wife. The overall battle was no fun and I would wish the gigantic hassle on anyone. What should have been a more enjoyable time of discovery in my life was turned into a contest for my very being. The end result was a suicide attempt on my part which was fortunately unsuccessful. From there my wife won the struggle and I decided to "purge" for the final time in my life, grow a beard and reject completely my feminine self. Through it all, she went back into her closet but wasn't at all happy about what had happened. Sadly. she didn't have to stay in her closet long because within a year, my wife passed away from a massive heart attack. 

Very quickly after the death, it was clear to me which way I would turn. My inner female reasserted herself and brought joy to me during the darkest moment of my life when I didn't know what I would do. From then on, she didn't have to share me with anyone. It took awhile for her to accept my wife Liz but once she did, she went all in. It took her over a decade of interacting with Liz before she decided to get married. 

Over time, again and again the true dominant gender I was dealing with won out. Mostly by biding her time. When she did have her chance to live, it was amazing to me how fast and easily she took to her new life in the world. All the times I was facing the gender unknowns in the world, she would step in to help me.

She proved not sharing me ultimately was the correct move to make.   

Procrastination

Image from Brett Jordan
on UnSplash

For as long as I can remember I have been a procrastinator. Unless I was really pressed, it was always easier for me to put off until tomorrow what I should have done today. 

Later in life, being a procrastinator in my gender life came back to haunt me. As I continually gained ground in learning if I could exist in a feminine world, the more the pressure on me increased to decide what I was going to do with my life. Primarily effecting my already fragile mental condition. I had previously been diagnosed as Bi-Polar along with having elevated anxiety so I already had plenty to deal with mentally. So, I was not in any position to improve my mental condition by procrastinating over my transgender issues. Still I persisted and my problems only escalated. 

I was frustrated when every success I found as a transgender woman, seemingly just led me to the ultimate decision I was having a problem facing. Was I ever going to be follow my dream and live as a woman. Plus, all my procrastination led me to was an increasing reliance on alcohol to limit the mental pain I was suffering. What happened was, the effects of alcohol gave me courage to explore further if I could make it in a feminine world as a full time trans woman. Was I gay, was I trans? I needed to know.

Finally,  rational thinking took place and I could take it no longer. My gender truth was slowly but surely killing me. One night I sat down by myself and made the biggest decision of my life. As soon as possible, I decided I would seek a doctor's approval to begin gender affirming hormones and never look back on an old male life which was always a struggle to maintain. What a relief it was to finally face my truth and move on as my authentic self. It was time to put all my procrastination behind me and my life immediately began to improve. 

Still I was not up on any pedestal. As I always mention, I could have never have accomplished what I did without the help from several key cis-women friends and family. In essence my friends pushed me over the cliff into a world I had only ever dreamed of. Perhaps, not so surprising, my reliance on alcohol started to decline as at the same time my overall mental health began to improve. 

Ironically, my only problem became that I procrastinated coming out as a transgender woman as long as I did. I would have loved to have the years back when I anguished over which of the binary genders I would live as. In other words. sometimes I think I wasted too many years to claim a life as my feminine self I just kept putting off. The only excuse I had was, during my procrastination years, the world around me was changing. In the pre-internet years, there was a definite lack of information and contact. Our dark lonely LGBTQ+ closets were difficult to escape. 

The fact remained I still grew up putting off the most important aspects of my life and it continued until I finally decided enough was enough and it was way past time for me to live as a transgender woman fulltime.