Ditching Good with Better as a Trans Girl

 

Archive Image
from Witches Ball
Tom on Left.

Ditching good with better has always been a difficult obstacle in my life. 

I always blame my parents for my feelings on doing the best I could on anything I tried. Nothing I did was good enough. If I got B's they should have been A's was a prime example. Even though I was an above average student, I don't remember ever being told I was doing a good job. I think now, their influence carried on with me in every facet of my life, including when I was a novice cross dresser and budding transgender woman. 

It all started with my appearance as a girl. When I was younger and before I went through any testosterone poisoning at puberty, it was much easier to look like a girl. But just looking like a girl was never good enough, I wanted to be a girl and enjoy their life. Or at least as I perceived it to be. I guess my parents attitude was rubbing off on me. At the time, all I could really do to further my looks was to over achieve with my meager allowance and take on a rural newspaper route. Between the two, I could sneak out to the store and buy the occasional wardrobe item or makeup I could experiment with. I was doing my best to ditch my good with better as a trans girl during my early age. If I had given the same effort to everything else I tried during that time, at the least I could have received better grades and my parents would have been pleased. 

On the other hand, my parents in no way would have been pleased if they had known I had issues with my gender. I shudder to think what would have happen to me if they had discovered me dressed in my feminine wardrobe and makeup. At the least, I know I would have been sent to a therapist during a time when even being a cross dresser was considered a mental illness. I never wanted to even consider what the worst could be. Perhaps since we were not particularly religious, Christian conversion therapy would not have been in my future. The only thing I know for sure is, I would not have had any understanding at all. All along I did the best I could and was able to hide my cross dressing with the world. How I don't really know.

The older I became, good certainly did not become enough. A prime example would be the Halloween parties I went to when I was first testing the world  I started with just trying to be a sexy sleaze of a woman thinking I would receive some sort of a validation. Several parties later, I grew more bold and wanted to see if I could be mistaken for a real woman, so I wore my business attire and then waited for reactions. Overall I was received well with strangers who did not know me mistaking me for a woman who did not have a chance to dress up for the party. I was discovering better was always best when it came to how I presented as a transgender woman in the world, under the cover of Halloween or not. 

All of my experiences led me to establishing myself in a new feminine world. I needed to try very hard to do away with all my old values to do it. My whole world became a concentration of new friends and life. In my own way, I needed to be better than the world to succeed in chasing my dream of living full time as a transgender woman. Sure I needed to look the part but suddenly I needed to be the part which meant moving and communicating as a woman. 

Ditching good for better in my transgender world was one of the best moves I ever made. By the time I was medically cleared to begin taking gender affirming hormones or HRT, I was more than ready for the results. Almost instantly I knew I made the right decision.  Since my parents have long since passed away, there is no possible way for me to communicate to them they were right. For all the wrong reasons. Their resistance  to giving me any positive feedback early in life made it easier for me to find my own path in the world as a trans woman. A place where good was never enough for me.  

Gender Expectations

Image from the JJ Hart
Archives

As I progressed through my gender transformation, I had so many expectations.

All I really wanted to be when I grew up was a woman but I had no idea of how I was going to achieve my dream. Unlike most of the major professions available to me, there were no schools I could apply to to be femininized. I just wanted to find my passion and follow it. 

To do it, I finally had to be free of the mirror and join the world. Even when I discovered that, I had to often snatch defeat away from the jaws of victory. Or I was defeating myself by going exactly the wrong way with my women's fashion, hair and makeup. At the rate I was going back then, there was no way I was ever going to exceed, or even make it, to my gender expectations.

Another problem I encountered was the complexity of the new life I was trying my hardest to live. Every time I turned one corner it seemed I had another blocking my way. I began to see life as a series of walls I needed to climb. For example, if I couldn't learn to communicate with the world, how could I ever hope to bring my dreams to life. Many times as I journeyed out into the world, I was flying blind not knowing what to expect. The whole process was at once scary yet exciting. It took me many evenings out on my own to establish myself in venues I wanted to be secure in. At the time, I was doing my best to separate myself from the gay bars I was going to where I did not enjoy being treated as a drag queen. 

It was very difficult at first to be accepted as a single transgender woman in the sports bars I was going to. Often I resorted to using my cell-phone as a prop to fend off anyone who thought I was going to be alone for any length of time. It was during this time when I started to meet a trans woman friend of mine and socialize in many venues I was fearful of going into by myself.  There seemed to be an extra amount of security when I was with a friend. When we were together my gender expectations were satisfied because I was allowed to relax and be more social in the world.

From there I transitioned into having my lesbian friends and had a chance to really blossom. All of a sudden, I did not need a man to validate my existence as a woman and they helped me climb another big wall towards achieving my dream. My experiences at lesbian mixers, roller derby matches and even professional football games helped me to come out of my gender shell fast. By doing so, I needed to free my long dormant feminine inner being so she could help me to become a new person. She gladly did so and took off tons of pressure from my gender expectations. If I did not know what to expect, she did and took charge and maybe most importantly gave me the chance to build a quality trans person. I had the rare second chance in life to learn from my mistakes as a cross dresser and a man.

I finally ran the string out and had seen all I needed to see as a transgender woman and couldn't wait for the gender affirming hormones or HRT I was approved to take to take further charge of my body. All my expectations had been exceeded and there was no way I could have dreamed of coming this far in life the first time I slid into hose and a bra when I was a kid. 

I don't completely know why I made it but I sure am happy I did. Along the way, my gender expectations were often confusing to me and impossible to explain to others. Even though internalizing my feelings was brutal, good therapy helped my mental health. Even more so if I had listened to my gender therapist years ago who told me there was nothing either of us could do about my desire to be a woman. Of course I was stubborn and did not listen. If I had, my gender expectations may have really changed for the better much earlier in life.

Buckle Up!

Image 
from the 
Jessie 
Hart
Archives

Recently, I have happened across several posts on my social media feeds from novice transgender women just beginning HRT or gender affirming hormones. 

In many ways, as I look back on my hormonal experiences, I am envious. Mainly because my experience was so exciting. Possibly because I was finally realizing my attempt to take a major step forward in my transgender transition. For years, I had dreamed of starting HRT, much to the chagrin of my second wife who was completely against it. She had always told me, she did not want to live with another woman and the hormones would take me dangerously close to doing it.

When I actually started down the HRT path, little did I know how right she would be. I was naïve and I thought my new journey would involve growing breasts and hair but never dreamed of all the other changes which would take place. My skin softened along with my facial angles which helped  my feminine presentation in the world. I could use much less makeup and do away with wearing wigs because I was fortunate I did not inherit any male pattern baldness.  

Before I knew it I really wanted it to happen, I was becoming very androgynous and had to do something. With my hair, breasts and skin alone, it was time to begin to think about the circumstances to what I was doing. Plus, I have not even mentioned all the extra benefits of going through the second major puberty in my life. When I did, I discovered so many new things about myself such as when my sense of smell suddenly improved and my body's thermostat went away. What happened was I was cold all the time and suddenly understood women were not making it up all the times when they said they were chilly.

Then there were the onset of emotions I went through when I started HRT. Previously in my male life I had become very insulated when dealing with my emotions. Sadly, I became so callous, I had a difficult time shedding a tear when my parents passed away. Suddenly, one night, when a late summer thunderstorm moved in, I sat alone on my side porch and started to cry for the loss of my old male self. It was such a powerful moment in my life, I will never forget it. 

Of course if you are just starting down your path to femininizing hormones, there will be many peaks and valleys or ups and downs. Similar to so many others, I questioned the gender path I was taking. Was it the correct one? So, I buckled up for the ride. I'm not sure now if I was ready for the first hot flashes I went through which hit me when I was out in public and I ended up wondering if the world had noticed I was getting ready to internally combust. Perhaps back in those days, the worst part of my gender journey was I had no one to share it with. I was just getting to know the small circle of women friends I started to hang out with on a regular basis and knew they would only say welcome to their world if I brought up anything such as hot flashes to them. 

After awhile, I came to the conclusion I had buckled up for one of the best roller coaster rides there were. The best part was, for the most part, I had no idea what was coming up next. When I was approved for larger dosages under the care of a doctor, changes continued to come at a rapid pace. Under medical care, I went from pills to patches which supposedly helped with the wear and tear on inner organs such as kidneys. Life was good as I adjusted to the new hormones and I felt as if my body was telling me I was a natural for gender affirming hormones all the time. 

The very few people who knew me pre-transition said it the best, I just seemed more relaxed and happy now as a transgender woman. I never said anything but I gave most of the credit for my new found joy to the hormones I was on. HRT had helped me to sync up my internal and external gender feelings. It would have been "TMI" or too much information for the average person to understand. 

I will always wonder how my deceased second wife would have reacted to me as a transgender woman. Would I ever have paid enough dues to move out of the pretty pretty princess mode she threw me in and ascend to the woman mode she was so afraid of. I would like to think at the least we still could have remained friends.  I will never know.

At the least, your journey will be different than mine in many ways and will include many twists and turns. Just try to enjoy the journey many others will never have the chance to take.

Cha-ch Changes

 

Vote BLUE!

After many years of keeping the blog title the same, I have decided to modernize it to reflect the name I adopted as my legal moniker approximately seven years ago. 

How I came by my final name change requires a little explanation. As many of you know, my daughter was and has been one of my biggest supporters. In a very short period of time she brought up the idea of where did I come up with my name of Cyrsti. Even though it is spelled different than the usual Kristi because of the way a light reflects when it goes through a prism. My daughter did not like it. Regardless of any of that, my daughter and I had a quick meeting of the minds and decided I needed to come up with a different name. Mainly a name which would be easy for my three grandkids to deal with and remember.

For a name, I decided to go back into my family history and select from the people I respected. For a first name I decided to go with a femininized version of my paternal grandfather's name. Then for my middle name, I decided to go a little rogue and honor my Mom by selecting her first name as my middle name. I say rogue because my Mom roundly rejected me when I came out to her years ago when I was home from the Army. As the years passed by and I became mellower with age, I began to have a better understanding of where she was coming from. 

She was firmly planted in the WWII/Great Depression mentality. Which left little room for understanding so called radical ideas such as gender issues. After her rejection, I was left to deal with my gender dysphoria on my own and we never discussed it again before she passed. I came to look at it this way, she put in the effort to birth me and raise me, so I could honor her as the daughter she never had. 

Happily, the name change has worked well. The kids seem to like it and outside of a very few instances. I have had no problems remembering  not to sign my old dead name. 

To preclude any added confusion, Cyrsti and JJ are the same person in the blogging world although Cyrsti does not exist anymore in the real world.

On another topic, even though I was saddened to see Joe Biden step down for reelection, I am extremely excited to see the quick progress Kamala Harris will have to get up to to speed and beat the former president who I have ranted against so often. If any knowledge you may have gained about Project 2025 has not swayed you against him by now, I can't say anymore except you are done living in a country we all used to know. 

Running from the Pain

 

Image from jc 
gellidon on UnSplash

Most certainly, I know I am not alone running from the pain of my gender dysphoria.

Most of you have been through it also. You know it takes a great amount of effort to out-run your issues. For me, it has been a survival of the fitness scenario. I was stuck between the proverbial gender rock and the hard place. Exactly between the two primary binary genders, or male and female. Of course I was raised male and often resented it. When I did resent where I was in life, I just became more and more frustrated and the pain set in. 

As the pain set in I had two alternatives as I saw it. Internalize the fact I was transgender or run from it. At the time, I hit a personal wall I didn't even know was there. When I became tired of totally internalizing my gender issues, I set out to outrun them. I ran from my native Ohio to the suburbs of New York City then back again to rural Southern Ohio along the Ohio River. At the same time, I was switching jobs almost as fast as I was changing my shoes. I was fortunate in that I was in an industry which was expanding rapidly and there were quite a few new job opportunities to be had. At least when I landed a new job, I had the opportunity to take my mind off of my true problems. 

None of the running worked and the pain increased. The only things I learned were there were pockets of acceptance wherever I went, including unlikely ones such as Parkersburg, West Virginia which had a small but active LGBTQ community. The problem became I could not become too involved with any transgender related activities without resistance from my second wife. So again my frustration and pain increased because I was so close yet so far away. 

Finally, I could stand it no longer and needed to face up to my gender problems. At the time, I was increasingly exploring the world as a transgender woman. At one point, I was even living half and half male and female. I was learning I had much more energy when I was in the feminine world than when I was living as a man. Even when I faced giving up all my hard earned male privileges. Increasingly, I shed a majority of my gender pressure and decided for sure I was transgender and then go for a life which reflected my new decision.  Since I had cross dressed so long I figured I was doing something  right especially when I felt so energized and natural in my life. I will forever remember the exciting yet scary night when I decided to do away with my male life and transition into a feminine world.

By doing so, I put my pain behind me and could stop all the running I was doing. It felt so good to relax and take a breath after all those years of running. Initially, I did not know how to act with all the gender freedom I was experiencing. Of course I learned to live a new life I had only ever dreamed of and was able to actually bring a portion of my old male baggage with me and discard the rest.

Baggage is actually a topic for another post but simply put, trying to carry all the extra baggage of two genders was exhausting. I don't see now how I did it but I survived, barely at times. Running from my pain nearly got to me and led me to suicide. Life then went full circle and I was paid back with the help of friends together we pushed back what was left of my male self and my female self prospered.

Much More than a Phase

 

Civil War Cemetery image
from the Jessie Hart Archives. 

When I was first experimenting with wearing woman's clothing, I worked long and hard to hide all my feminine wardrobe and makeup. 

Due to transportation and financial constraints I always had a difficult time adding to my very limited collection. Plus, I always wondered if my Mom ever really discovered her clothes and others I managed to "borrow" for my cross dressing trips to my mirror. If she did, she never confronted me about it. Perhaps she thought it all was a phase and I would grow out of it. Similar to the fallacy, being transgender is ever a choice, I learned my gender issues were much more than a phase.

Very early on, I discovered a lesson I should have relied on but kept on ignoring. The lesson was, I wanted to be a girl, not just look like one. The very beginning of the realization I was transgender as I envied everything girls around me did.  Which went far past their pretty clothes while I was stuck in my drab male clothes. All along I was stuck in a family which valued male superiority and I wanted to rebel but couldn't. I often wonder if I had been born into a more diverse family (if that was possible back in those days) I could have made my feelings known and thrived. Instead, I did the only male thing I knew how to do and internalized all my inner feelings. I even thought, if I ignored my gender issues long enough, they would turn out to be a phase and go away.

Of course my gender dysphoria never did go away and just grew worse as I began to understand the full depth of what I was facing. As I look back, Halloween parties were my first indication I could do more than living a shallow life in front of the mirror as a cross dresser. I learned the hard way, heels weren't so much fun when I first wore them on long walks all the way to how much fun I had experimenting with the clothes and learning from the parties as a whole. Another step towards showing me my phase was not going away, I was just growing into it.

Halloween parties proved to be false feedback in many ways. Most people who saw me were friends who thought Haha I was the clown dressing as a woman for a laugh. Even though I was going as far as shaving my legs. In my mind, my legs alone would do the trick and everyone would know I was much more than a once a year man putting on a dress. At least I wanted it to as I grew confident I could present more and more as a real woman at the party. When I had achieved my goal, I felt I was ready to pursue a future as a successful transgender woman. 

When I did, the work really started. Life was so much more challenging as I left my male phase in my past. I wonder now if my Mom ever thought my simple love of girls clothes was a phase, what would she think now. Outside of the one time I tried to come out to her as a transvestite and she rejected me, we never discussed it again before her death. I can't help but look back and regret how much life I may have lost if she would have ever accepted me. I on the other hand took the high road and honored her by using her first name as my new legal middle name.  

Normally, phases come and go but certainly none of it applies to being a cross dresser or transgender person. Once the public at large learns to accept we are not a phase, trans kids especially could benefit from more understanding when they are young. Parents and siblings could have a more serious outlook of what being trans is all about, helping the whole situation. Or, leave the phase out and help the person. 

Sink or Swim

Image from Trans Wellness Event. 
Jessie Hart Archives. 

Many times when I first entered the world as a new cross dresser or femininized male, I wondered if I was going to sink or swim.  

Leaving the mirror (who never lied to me) was difficult because the public didn't lie either and let me know if I blended in with other women or looked like a clown. Of course when I was stared at or laughed at I sank to depths of depression as I thought I was in too deep and would never make it to my transgender dreams. 

I discovered sometimes the hard way when I was out in the world, I could not turn back and needed to stick it out, even when the going got tough. It included the times that got so bad when I was laughed at. Then, something deep inside of me kept saying move on because times would get better. Similar to when I learned to swim at an early age, I gained confidence in the water and I began to swim onwards and learned women's fashion, hair and makeup which came closer to flattering me. 

Often my biggest problem was myself. My old male ego was telling me I needed to try to look a certain way when the opposite was true. I needed to blend in with other women in the venues I was going to which was especially important when I made it out of the gay venues I was going to and into the world I was used to as a man. Perhaps I was mistaken for a drag queen in the gay bars because I was dressing as one. Slowly but surely I started to be accepted as a transgender woman in the preferred venues I went out to and I began to swim with the big girls. By doing so I accepted the extra challenge of communicating with them. Far beyond just appearing as one of them.

As I always say, women lead a much more layered lives than men and here I was right in the middle of them trying to swim with the current. Which at times was difficult to do. I had so much to learn in a very short period of time. In order to not sink in the situation I was in  It took me tons of lonely soul searching to figure out if I was moving my life in the right direction and was losing all my white male privileges worth it. Of course you know I knew it was and I kept swimming towards my dream of living as a transgender woman. 

I was lucky when women along the way threw me life jackets to keep me afloat in my time of need. Their efforts just helped me to decide somehow I wanted to be more like them. If I survived my male to female gender transition, maybe then I could pay it forward and help other novice transgender women. Which is the primary reason I write. Most certainly I am biased but I think crossing the gender frontier is one of the most difficult tasks a human can undertake, so any assistance is good assistance Especially when we are swimming against the tide of society. 

Hopefully, if you are becoming tired or confused during your gender swim, I can throw you my version of a life jacket or boat. You can beat society's system and succeed if you are careful and keep trying. I sank so low once I tried severe self harm (suicide) to myself and was lucky I made it to the surface and survived. I bring it up simply as an example for those who think being transgender is some sort of a choice. It's what happens when trans women or men are round pegs being forced into square holes and never given the chance to sink or swim.

There are many ways to find your way to womanhood as a transgender woman, you just need to be patient until you find your path.

Finding your Happy Place

From the Jessie Hart Archives 

 As a transgender woman or trans man, it is often very difficult to find your happy place.

A happy place can often be called gender euphoria for all of us who suffer from gender dysphoria. If you don't know, dysphoria is the often evil process of hating the gender you were born in. After all these  years, I still dread the first look in the mirror every morning. Who will I see looking back? My same old masculine self, or a femininized version of him. Some mornings I land in my happy place and others I don't. I usually settle on a middle point until I am done with the mirror.  On occasion too, I suffer from having an impostor syndrome. When I think do I even belong here at all. Happily, the syndrome goes now away quickly because I know I have earned my place as a transgender woman.

Earning my place was never easy as I never inherited any feminine characteristics to start with. What I did have was a testosterone damaged body to work with. The only positives I had to work with were the compliments I received  on my freshly shaven legs at Halloween parties.  Then I had the tendency to overdue it when I explored feminine fashion. I thought I should emphasize my positives such as my legs and at the same time play down my body negatives such as a thick torso. All of it led to massive fashion mistakes before I learned to dress to blend in with the other women I encountered in public. I lived through all of those and found a happy place I could live with.

Around this time was when my happy place location started to change and move around. It shifted from appearance only into a personality based place. Mainly because, suddenly I was closely interacting with the public as a trans woman. It all meant so much more to me than my days as a casual cross dresser. All I know was I was up to the challenge and enjoyed my new happy place everytime it presented itself to me. Outside of a few instances of impostor syndrome, I was learning more and more I could indeed live my dream of being a transgender woman in the world. It turned out my happy place did exist in the feminine world and more and more I wanted out of my old boring male existence. 

Still I had a lot of climbing to do to rid myself of the old baggage I needed to lose to transition. I wondered at the time what I would do about everything I loved in life such as my daughter, (hobbies such as sports) and what was left of my business. It turned out destiny took it's own course with my baggage. My daughter supported me completely while my brother rejected me, so I was the recipient of the best part of the deal. As far as my business went, it mercifully closed due to a weakened economy and other factors, leaving me close to having an early retirement. As far as hobbies went, ironically I found a group of women who were as passionate as I was about sports, so I had friends to watch our favorite games with. So as you can tell, outside of the obvious gender issues, I was able to restart my happy place without a whole lot of extra effort. 

When I found my new happy place, it felt so natural I wondered why I did not pursue it earlier. I know early on I was into my appearance as a woman completely and often missed the basics of movement and communication to further my femininity. It turned out I did not have to worry because the deeper I delved into my new life, the more fluid and natural I became. Practice made perfect in so many ways along with the fact I became secure into who I was. When I did, I didn't care what others thought of me and my confidence as a trans woman increased.

It turned out, destiny took it's time but ultimately led me the right direction.    

The Gender Waltz

Image from Clarisse Meyer
on UnSplash

Since the beginning of time, the two binary genders have done a special dance with each other. 

Being transgender, I have been fortunate to have seen and experienced dancing from both sides of the spectrum. Before I go any farther, I do need to say I am a terrible dancer. In fact, the only time I have tried to dance was when I was so intoxicated I could barely stand up. Sadly, there were recordings made of my dancing struggles.

Certainly, my struggles with dancing were with women . I still tried but since I was so shy, I had very few interactions with girls or women at all. No dancing for me outside of the lessons my Mom made me take. It made it worse as I was at the embarrassing age when many girls were taller than the boys. We learned such trendy dances way back then such as the Cha-Cha as I remember. The grand experiment failed and immediately, I tried to put the entire experience behind me.

Of course gender waltz's go way past just real live dances. Just one of the main ones is inter-gender communication. When the book came out called Men are from Mars, Women are from Venus and appeared on the book stands, I wondered where was I from? It took me years to figure it out. I was from neither. Regardless, it did not take a genius to figure out there are very big differences in the genders other than biological. It is the reason, men and women have such a difficult time understanding each other.

Interestingly, the differences between  the genders extend to what friends we choose. In my case, since I grew up with only other males in my neighborhood, early on all my friends were boys. However, as I grew older, the vast majority of my friends were with women and I had very few close male friends at all. I guess deep down, I was getting ready for my future. 

Recently, I read a post from another transgender woman how she vastly approved having men friends over women. Why? Because she didn't  really like the interaction with other women including the body language on how they crossed their legs  all the way down to how they were sitting. In addition, she didn't enjoy the feminine give and take very much. She much more preferred to talk to men. In my case, I waltzed in the opposite direction. I didn't like the reaction I was receiving from men when I talked to them as a transgender woman. So I resorted back to when I was a guy and was able to communicate the best I could with the women around me. It was all I could do to survive in a new gender world. 

None of my new dance was easy to do. Even though it felt more natural to me. With women, especially, I needed to try to judge what they were really trying to say to me, often in a round about way. Was a compliment really a compliment or merely an opening to try to find out something else about me. I learned the hard way how to dance in a new world not as a cross dresser but as a novice transgender woman. Who knows, maybe other women sensed my innocent approach and it helped me to be accepted. Until the newness of meeting a transgender woman wore off and life resumed. 

Outside of a few exceptions, I rarely had many interactions with men I sought out and was accepted into a world of women. I enjoyed my new dance so much and wanted it to go on forever and so far, without a few exceptions, it has. Maybe I was just trying too hard to dance the wrong way after all.