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.   

Trying too Hard

Photo from the 
Jessie Hart Archives

As I was attempting to find my way in a new feminine world, I caught myself trying too hard to succeed. 

I tried too hard primarily when I tried to upgrade my presentation as a very serious cross dresser or novice transgender woman. The biggest problem I was having was, concentrating just on how I presented was the wrong path to take...if I took it too seriously. What I mean is, I needed to appear the best I could without going overboard and opening myself up to scorn or negative pushback. I was stubborn and held on to my hard earned previous ideas and took quite a while until I arrived at the point where I could blend in with other women close to my age. 

Now I wish I could have seen the light at the end of my gender tunnel was not the train and was actually a light which would shine bright on my future as a transgender woman. I just had to reach out and grab it if I had the courage. I was far from being any sort of a hero or role model, I was simply a person desperate to find herself and find my way down my gender path. It turned out, lessons I had previously learned in my male life came back to really help me. A prime example was my biggest lesson from Army basic training. A friend of mine who went through basic ahead of me said don't listen to drill sergeant threats and as soon as you got into shape there wasn't much else they could do to you. I connected the dots to the public scorn I received early on as a cross dresser. Once I recovered and learned what I did wrong, I could move on to be successful. 

At this point, defining success is important. Success to me became when I relaxed to the point where I could enjoy myself to a point. Often my male and female selves were fighting a serious battle for my soul. Of course my male self did not want to give up all the privileges he earned the hard way in a life he never really wanted. At the same time my strong feminine self was still wondering and waiting when her turn would come. It finally did work out for her and she didn't have to try too hard to enjoy it.

In fact, the whole time she was struggling to see the light, she was learning what she would need to do when her chance came. Now, life has come to her naturally and she is able to enjoy it. No more obsessing about what would happen next as far as her gender is concerned. Now fashion can be fun again and not so much of a chore wondering if everything works together. 

During the holidays, since my daughter has converted to Judaism, and my wife Liz is Wiccan, I don't have to try too hard anymore to find the perfect gift. 

On occasion, at my age, I think I have paid my dues primarily on my gender path. Now I can hope for the best as my life nears its end. Not being a pessimist, I am seventy four and no one lives forever and I consider myself fortunate to be one of the few humans to have experienced a life on both sides of the main binary genders.  

Merry Christmas

 

Christmas Party Image
My wife Liz on right.

Or should I say Happy Holidays to those of you who may prefer it. I am not particularly religious but deeply spiritual.   

No matter how you worship, or don't, hopefully, you were able to spend your day with family, adopted or not and find satisfaction. 

Now, it's time to say how deeply grateful I am to all of you who take the time to stop your day and browse my writings on whatever internet platform you choose.

Perhaps today also you can take the opportunity to pause all the drama which normally comes with the season and discover the blessings you may have. 

As I sit here watching the "Yule Log" on TV and getting my fill of Christmas music and I have my copy of "It's a Wonderful World" cued up (along with a Christmas Story) I'm ready to enjoy a mellow Christmas Day, thinking of you all.