Tennis Anyone?

Image from Tony Luginsland
on UnSplash.

 Back when I managed a prominent casual dining/bar venue, we had two women who would frequently come to our bar after finishing their round of tennis. 

Of course, I always noticed and was jealous of their short tennis outfits. I immediately put acquiring some sort of a tennis outfit on my cross dressing to do list. Since I had always admired short mini skirts and dresses on women, finding a short mini white dress to wear as the primary part of a tennis outfit was a priority.

As luck would have it, I found the ideal dress at a women's clothing shop in a mall I always went to. Once I had the white dress, I discovered the rest of the outfit would be fairly easy to put together. I ended up finding an inexpensive pair of white tennis shoes and socks to go with the shoes. The only problem I had then was what I was going to do about the hair on my legs. 

Even though my wife knew I shaved my legs on occasion, she was not overjoyed when I shaved. Primarily because she worried, I was up to no good when I shaved my legs, and she was right. On this occasion, I could not wait to show off my legs and new tennis outfit in one of the malls I always went to. Before I went to the mall, as always, I needed to create the time to do it away from my wife's disapproving eyes. I waited until she was working a day shift, and I began the fairly intense process of shaving my face and legs. 

Once I completed the shave and applied my makeup and hair, I was ready to test out my new tennis look outfit on the world. Immediately, I felt the thrill of my shaved legs in the short white dress I was wearing. So out the door I went into the world. As I arrived in the mall, I noticed my supposedly admiring public was primarily made up of retired men in the mall just to walk and admire the view. Since I was the view, I wore a pair of sunglasses so I could watch their reaction to me without being obvious. It worked and I could see them staring at the tall blond in a tennis outfit.

As I saw it, I received all the pleasure from tennis without putting in all the work. Now all I needed to figure out was how to hide my extra women's clothing. On this occasion, I used a little used closet and hid my new treasured outfit among a set of my old male clothes I never wore. 

For a change, my ideas of how to come as close as I could to learning for myself how a woman would feel in a tennis outfit came together. I could show off my legs and have fun doing it. Plus, I could cross another item off my transgender bucket list. Quickly, I was off to another quest. 

Seraching for Me

Image from Selcuk S
On UnSplash.

Ironically, during my life I have spent too much time searching for who the true me was.

Naturally, I am referring to finding the springboard I needed to determine which gender I was. When I was younger, I made the habit of waking up in the morning wondering if I was a boy or a girl. I was very gender fluid for years before I decided which gender direction was the correct one for me. The problem was I needed to put on my gender blinders and attack the world daily as a male. Something I never wanted to do.

It turned out the springboard I needed to find out the me I was looking for was still a long way in coming. I still needed to cross or follow many paths before I found me. More precisely, I had parenthood come into my life as well as many challenges such as military service, marriages and just life in many ways. I was constantly searching for my gender by going out and exploring the world to find out if I could ever achieve my dream of transgender womanhood. The journey was so difficult when I experienced negative feedback From stares and giggles, all the way to people singling me out for pictures, I did it all before I made a better effort to blend in with the rest of the world.

All in all, I found just being me was going to be much more complicated than I ever thought possible. It all started for me in the days when I always thought the grass was always going to be greener for me on the feminine side of the border. I discovered, even though my trip across the border was terrifying at times, on the other hand I felt so good and natural, I knew there could and would be no turning back. No matter how easy it would have been. At times, I was even a bit jealous of men who had never experienced any gender issues and were able to live out their lives enjoying male privileges. It all just was not in the cards for me during my life.

Just me, turned out to be so much more. I am a parent, a grandparent and a spouse to a supporting wife. In other words, I am so fortunate to be surrounded by people who care for me. Plus during my life I have been able to take an in-depth dive into how both main binary genders operate. What really breaks my heart is when one of the bigoted transphobic political commercials comes on with all it's lies. I want to tell the haters that even though I am a transgender woman, I have a life not so different from theirs. I am just busy being me.

Perhaps the problem is, since my life turned out to be more complex than the so-called norm, so people don't want to understand or care. 

By this time in my life, I have learned being just me will have to be good enough. I have worked too long and hard to give it up now. From having a gender fluid lonely youth to finding my true self in trans womanhood, I think I have been fortunate to end up where I am. Plus, I will continue to advocate for all transgender women or trans men such as my transgender grandchild with their whole life ahead. There is so much to do. Maybe I can just be a positive example to another novice transgender person still living firmly in their closet. Who knows? Maybe you can be next to escape and live as your authentic self.

What Would Mom Say

Image from Jenna Norman
on UnSplash

This week my question to answer on the year long bio I am writing for my daughter and family as well as my wife Liz involved what parent I learned the most from.  

As I compared my Mom and Dad, easily I learned the most from Mom. Outside of the usual circumstances, I found I could find many more opportunities to spotlight Mom's influence on me. For example, I remember at a very early age watching Mom put on her makeup. Being a product of the "greatest generation" she was not shy about dressing up. However, I don't think watching makeup being applied led me to being a transvestite or even a transgender woman really mattered. Somehow the gender issues I faced went much deeper. Perhaps as deep as the medication Mom took during her pregnancy (DES) which was offered to women at the time to prevent problem births.

It turned out, I was successfully delivered just before my parents had decided to give up after three still births and adopt a child. I think because of all of that, my Mom put an extra emphasis on raising me and my brother who came along two years later. So much so, I wonder now what would have happened if Mom would have realized she had a daughter rather than a son. In all fairness to her, the fifties during my youth had very little information on gender issues. When it was available, gender issues were known as mental illness. 

Throughout the years, I always mistakenly thought girls had all the benefits in life I always wanted. Girls were able to wear the pretty clothes I wanted, be gifted the dolls I wanted and even never had to worry about being drafted and serving in the military. Male privileges were not known to me in those days because I had not yet earned any. As a side note, once I did earn the benefits of being male, I learned some of them were automatic and I did not want them anyhow.

I have forever wondered what my life would have been with Mom had I been born a biological female. Being as similar personality wise as we were, we fought quite a bit as mother/pseudo son and I have to think it would have been worse as a daughter. Mom was very headstrong and I am sure we would have had battles over fashion styles in the 1960's as well as when I could begin using makeup. In fact, when I was sneaking around using her makeup, I was probably younger than I would have been had I been her actual daughter.  I am sure too, Mom would have tried to influence me into going to her college and joining her sorority. She would have done her best to push me down a certain path which was certainly going against my generation's rules at that time in history during the upheaval in the later 1960's.

By this time, you may be asking where was Dad during all of this. It was not like he was not an influence in my life but he was not as hands on as Mom was. He was long on providing and short on emotions which I struggled with for most of my life. One thing I remember most about him was how desperate I was to never disappoint him and since I rarely if ever heard a positive from him, I never knew what he really thought of my life. He was blessed with excellent health and outlived my Mom by ten years and I never came out to him before his death from Dementia.

I did try to come out to Mom but it was a dismal failure for both of us. Predictably, when I told her I wanted to be a woman, she offered up mental health counseling. The conversation took place just after I was finished with my military duty and was never mentioned again until her death fifty years later. I used to hold her thoughts against her and was quite bitter but I gradually mellowed with age and came to realize she was just a product of her generation. 

To honor all her sacrifices, I used her first name as my middle name when I legally changed my gender markers nearly ten years ago. Had I had the opportunity to be accepted as her daughter from the beginning, it would have been interesting how our lives would have intersected. Way past the pushback I would have received for wearing my skirts too short and wearing too much makeup when I was a teenager. I know what Mom would have said. You aren't leaving the house looking like that. Maybe I should have thought of that when I tried and failed to dress that way later in life.  

 

Building from the Inside Out

 

Image from Brooke Cagle
on UnSplash

Years ago I began to understand I was building a new human being from the inside out.

I began to realize it when a person very close to me told me how fortunate I was to be able to start over in the world as a transgender woman. At first I was scared, could I really re-create myself as a woman and at the same time achieve my ultimate feminine dream. Following years of living and training, I found I could indeed live a life as a trans woman.

Before I did, I needed to decide what old male baggage I would have to discard or adjust to the fact I would have to bring it with me. It was difficult since I decided to seriously began my gender transition at the age of sixty, I had years to consider what to do with my baggage. Initially, I was part of the old transsexual school which believed you had to totally uproot your life and move when you transitioned and start all over. The problem I had was, there was some baggage from my old life I wanted to bring with me. For example, I wanted to try to preserve contact with my family and wondered if my wife (who I loved completely) would ever accept me. Not to mention other key points of my life including my passion for watching sports. 

Fairly quickly, as I transitioned, I was able to indirectly control all I was building from the inside out. By this time, I had worked out most of the appearance or fashion challenges I faced, allowing me to work on expressing my internal self. First of all, I learned my only child accepted me totally and my only sibling (a brother) did not. Sadly, we have not communicated in over a decade now. I know I have survived and I have assumed he has also and we moved on. Since I was now a different person now and he is entrenched in his ways, I am sure it has all been for the best although it hurt me how he handled it by rejecting my invitation to the family's annual Thanksgiving feast.

In many ways, having the opportunity to rebuild myself was terrifying yet exciting. Along the way, I found I needed to transition again. Mainly when I finally decided to make the mental move from cross dresser to transgender woman. I say mental move because I wasn't doing anything outwardly any different as I was doing my best to put my best appearance foot forward as a woman. I knew if I was successful, there would be no turning back on my gender path. It was a huge continuing beginning in the process of leaving my male world behind.

By this time, I was well on my way of deciding what baggage I could bring with me and what I could leave behind. I was preparing to give what was left of my male clothes to a charity and I had fairly quickly established myself as a regular in a couple of the big sports bars I had frequented as a guy. By doing so, I could meet my small group of new women friends I had met and watch the games we all enjoyed. My new life was coming together from the inside out and I was loving it. 

Even still, it sometimes took all the concentration I had to remember I was living a new life and I needed to rely on my inner female to carry it out. By doing so, I was able to say what I was thinking and not screw it up by injecting any of my old toxic male self. The only thing I could rely on was my new friends and their reaction to me since they had no clue of the old me. It was very liberating to say the least. 

Overall, I have to say, building the interior person was more intense when compared to the exterior woman the world saw. Especially when I needed to communicate more and more with the public as my new self. When I did build from the inside out, I learned to live my truth and empower my life as a transgender woman.

  

A Trangender Happy Place?

 

Picnic Image from the Archives. 
Liz on right. 

Is there really ever a "happy place" to be considered if you are a transgender woman or a transgender man.

During our lives, we go through so much turmoil and change, we have very little chance to be happy with our choices. Primarily because we enter our interactions with others in a dramatic way. A prime example is the swapping of gender privileges. I remember vividly the night I lost a portion of my intelligence when I attempted to talk about a topic I knew quite a bit about with a man, It was the opposite of the intimidation a trans man friend I know told me about his new communication skills with other men, including rest room visits. Up to the point of me thinking initially the only privilege I was gaining was having men open the door for me. Later I learned I was wrong, there were other more substantial privileges to be gained by joining the world of women. They were just hidden from me and I needed to earn it. 

All the gender privileges in the world I found could not make me happy. Of course I could trace my search of the illusive happiness back to my up bringing. Being happy was not a priority in our family and I did not know how to be happy. So it took me years to at the least be satisfied with my gender transition process but not happy. I just had to be willing to take the walk. Since the walk included many ups and downs, my happy place still was difficult to find. Also, per norm, I was doing my transition different than many others. 

Examples are how I found other women who accepted me for who I was. I did it by going out repeatedly as a single transgender woman and risking the inherent danger in doing so. I was lucky and escaped several potential risks to my personal safety when I did it. The small circle of friends I found and I consumed way too much alcohol and drove all too frequently. Something I do not recommend to anyone. Another chance I took was going on line dating sites to try to find a partner since I was so lonely. Predictably, I was hammered by trash and less than stable responses. Plus, when I refused to meet up with the occasional local person who responded to me, unless we met first in a public spot, I was met with no shows or some squirrely guy who wanted to wear my panties. Not to mention the guys who were married. One of which I had a fabulous date night with but I knew there was no future. 

Through it all, I was still thinking I could find happiness. Somehow, I knew happiness could be around the next corner of the path I was on and was I blaming I could not be happy because I was transgender. Quoting "Jelly Roll" there was a very dark hallway between my ears. I needed to give up any ideas of impostor syndrome when I was successful in the world of women. I could not be happy until I gave up all of the guilt. After all, I was not doing anything wrong when I just was attempting to leave my old male self behind and live as my authentic self. 

All of this leads me to the question, am I happy now and does a transgender happy place really exist. While I am satisfied with my life as it exists now, I still work at being happy. For me happiness will be a learned response I can blame my parents for and not a result of being transgender. In fact, more than a few of the moments I call gender euphoria (or happiness) came because of my gender journey. 

The problem with envisioning a life of not having gender issues is impossible for me because I have always lived with it and it was never a choice. So I am biased that a happy transgender place has been very difficult for me, I have partially lit the dark place between my ears and am constantly searching for more. 

Legacy?

Messy Office, Messy Mind?

As I see it, leaving a legacy is mostly a male topic.

Little did I know, being a transgender woman was probably the only legacy I could leave with my only child (daughter) and my three grand-kids. As it turned out, I did not have much else to offer. Especially not the usual male attributes such as wealth, possessions etc. A prime example was my Dad who was a self made man. Building his own house and rising to the position of bank president, mainly with just a high school education. 

Along the way, I was surprised to learn one of my grand-kids is transgender, so all of a sudden I became a role model. A role I never thought I would have during all the years of struggle I went through as I transitioned from my old unwanted male life. It turned out in many ways, I proved to my grand-kids anything was possible if they wanted it bad enough. And I was fortunate in that my daughter accepted me the way she did and wanted to share my new self with the kids. So I could not run away and hide. 

I was so successful, I made it to heights I never asked for or ever thought I could achieve. Without a doubt the biggest one when two years ago I received my first Mother's Day card and gift. The card brought me to tears because it was something I never asked for. It meant to me I made it to the pinnacle of my gender transgender transition. 

Adding to my legacy is a year long project my daughter gifted me this Mother's Day from a company who takes questions about me from the family for the duration and then combines them all into a book. When it is completed, I will have had the chance to write about myself and maybe equally as important, is the fact the kids will have the chance to learn about their great grandparents who they did not know anything about. It is important for me to be some sort of a bridge from the "Greatest Generation" my parents were part of to the kids of today. The entire gift is quite the chance to explain my legacy to my daughter and grand-kids. Since I have a degree in history from college, the entire process is important to me.

Legacy was something I had given up on when I left my male life behind. I thought no one would care. When it turned out they did, I was impressed and needed to change my attitude completely. In a way, all of a sudden having family care about my life made me proud of my gender accomplishments.  I indeed would have a legacy as a transgender woman past just someone who changed their name in the family bibles. 

Years ago, a friend of mine did a deep dive family tree research on my families, mother and father and found we had a revolutionary war relative. Perhaps now in the future, after I am gone, some other person with gender issues will read my story and understand they are not the first, not alone and can be successful living the life they want to live. 

  

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.  

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. 

Strong Women Role Models

Hand Beaded Transgender Hair
Barret from Liz T Designs on
Etsy 

 I am speculating most transgender women or even trans men have experienced at least one or more strong women in their lives.

For any number of reasons, women have been forced to be strong and carry the load for weak men. For many, their first entrance into true womanhood comes with having children. With current economic conditions the way they are, the days of the old fifties version of Mom staying home to raise the kids and take care of the house is long gone. To barely make it financially, both partners have to work.

Problems then arise when the man still wants to follow the old outdated male standards of doing very little around the house to help out. 

By now, you may be asking what does this have anything to do with being a transgender woman. With me, at least, it means a lot. My Mom worked out a deal with my Dad in the sixties. If she went back to work as a school teacher and used her college degree, my Dad would help her out with hiring a part-time housekeeper. Even with the help, Mom had a lot to do with two sons in a very male orientated family. Even though I admired my Dad for being a self made man coming out of the Great Depression and WWII, I had more on hands experience with my Mom who was very headstrong. Who knows, maybe that influence with her had more to do with me being transgender than anything else. Later I was to learn my gender issues ran deeper than one person outside of myself.

Even so, I still searched for the perfect woman to model myself after. I wanted to appear as the confident women in the world I saw moving around in their lives. The older I became, the more I learned the perfect woman did not exist and many women were hurting themselves attempting the be a successful person in the world as well as on the home front. Not to mention, the overwhelming problem of appearance. Until recent times, aging has not been kind to most women who among other things suffer from extended menopause. 

All of these factors contribute to why I have such a high opinion of strong women and how I think the world is changing quickly as many more young women seize the new opportunities in the world around them while young men play video games. 

With all the changes, it is important to figure out how a transgender woman can fit in at all. Certainly, we have to be a better woman to do it at all. Which means understanding all the layers of a woman's life. That is once of the reasons some women resist letting trans women play in the girls sandbox at all. As my second wife always told me in no uncertain terms, I needed to earn my way in. Maybe that is why I never considered her a strong woman role model for me at all. My Mom on the other hand, was a strong role model for me. From how she applied her makeup to how she battled me for my future, I appreciated all she did for me. Including of course, birthing me. She remained my role model even though she rejected me when I came out as a transvestite to her. She immediately said she would pay for a psychiatrist which I rejected. Since I didn't have a mental health problem because of my gender issues. 

We never mentioned my desire to change my gender the rest of her life but even so I decided to adopt her first name as my legal middle name when I transitioned and legally changed my name. It was the biggest honor I could think of for all the things she did for me. The most relevant thing she did for me was to show me what a strong woman was and how to be one. A trait I would really need as I followed all the ups and downs of following a new gender path.

It is ironic to me, the strongest women I know like Liz or Kim have very little idea of how much they have helped me along and the most frustrating part is I don't think I can ever repay what they have done for me. 

Who knows? You might be an offspring of the very few strong women like my daughter. She had to became an ally for her trans child and was then able to take advantage of helping her child at an early age. Maybe your Mom realized your authentic gender self and became an ally rather than the cruel opposite.  If you didn't, you were forced to do what the rest of us did. Study strong women close up and do your best to join their ranks. I was fortunate enough to be able to work professionally along side several strong women who I learned from. The women seemed to combine strength and humility seamlessly to forge a successful business career. 

There are so many variations on how to become a successful strong trans woman it is difficult to mention them all. We all need to the do the best we can to force our way into a world where sometimes we are not wanted.

A Zig-Zag Trans Life

Party night at Club Diversity
Columbus, Ohio.

 Maybe I should have called this post I should have zigged when I should have zagged. Or vice-versa.

In many ways, I see all sorts of transgender women or trans men in the same situation. I started at a very young age when I would zig away from my younger brother when we were home alone and I was able to get away from him when I cross dressed by locking myself in the bathroom. Fortunately, I never needed to zag because somehow, he never caught me and told my unapproving parents.

Somehow I thought when I got older, my life would improve. The first thing I learned was my urge to be or at least cross dress as a girl my age would not magically disappear. In fact, it became stronger when I learned it was not just a phase and I began to understand my gender dysphoria better. At that point, I really had to start zigging and zagging just to maintain my fragile mental health. When I was old enough, I even began taking myself to therapists to seek out help. My only main success which came out of it was when I was diagnosed with a bi-polar depressive disorder. It had nothing to do with my gender issues at all. As far as zigging or zagging, I was able temporarily save my marriage and received my money's worth when my gender therapist told me the truth. She could do nothing about me wanting to be a woman. Overall, my desires should not be a problem and I should face my truth. Of course, I wasn't smart enough to follow her advice and resumed all the zigging and zagging. 

It took me years and years to grow up and away from my male self and settle into a life as my authentic feminine or transgender self. By this time, I was growing so tired of all the zigging and zagging I was going through. Even though the whole process was an exciting time of my gender life, I was still becoming fatigued by my life the way it was. Ironically, when I was, I settled into a long term set of appointments with a very understanding therapist. She talked me off the ledge several times and along the way helped me secure gender affirming hormones and the paper work I needed to change all the legal gender markers I could. All of a sudden, I was able to visualize myself living my dream as a full fledged transgender woman. With my daughter's help, we were even able to come up with a new legal name which would reflect my family history and would be easy for my grandkids to use.

Finally all my exhaustion came to an end and I was able to live how I pleased. All the zigging and zagging had worked. All the times I hurried to hide myself away from friends and family, were put behind me. Through it all I learned one difficult lesson. If you can somehow believe in yourself, you can live your best life. Even though you may (like me) take years and years to evolve into your authentic self, the trip is usually never boring as you lead a zig-zag trans life. Overall, it takes a ton of effort to weave your gender issues into a life of family, spouses, jobs and friends. You learn to be forever vigilant in protecting yourself and end up internalizing way too much of your life. It seems the entire process is just ingrained as part of a transgender life as breath itself. We just have to finally zig to get around it. Then zag to adopt your new life as a trans woman.

Earning Motherhood

 

Liz on left with me preparing to celebrate
Mother's Day with her son over a Margarita.
Photo by AJ Trumble.

To be clear, I never have asked for the honor of being called "Mother" from either one of my off springs. 

I have a daughter of my own who means the world to me and a step son who I love very much. I met him when I met my wife Liz and was accepted into his world immediately with no questions asked. 

My daughter started the Mother's Day ball rolling last year when I received a small gift and a Happy Mother's Day for the first time from her. Truthfully, I was brought to tears by the thought. I was forever finished with Father's Day. 

I consider the title of Mother to be the ultimate compliment and as I said, not one I take lightly. I also think being referred to as Mother represents a total erasure of all the years of testosterone poisoning and an unwanted male life I went through. It means to me, my immediate family sees me as a full fledged trans woman. I even respected my own Mom enough to use her first name as my middle name when I legally changed it. Even though she never approved of my gender transition. Even to the point of being a relatively harmless cross dresser or transvestite. Back in those days, neither one of us knew the depth of gender issues. I considered Mom to be a product of her generation (WWII/Depression) and moved on after her death. 

Needless to say, most of my gender journey was never easy and represented many roadblocks along the way. I can only say, I never expected to arrive where I am today. Maybe I should come up with another book and call it "From the Mirror to the World...A Transgender Journey." 

We shall see.

Transgender Closure?

Image from Nick Bolton
on UnSplash.

 Sometimes it seems as if closure to a transgender woman never comes.

In the very early days in the mirror as I cross dressed, I thought I had reached closure when gender euphoria kicked in when I admired myself. It did until the pressure built to cross dress again and again. Predictably what happened was, I became so frustrated with the process of moving back and forth between the male and female binary genders, I decided to purge (throw away) all of my feminine belongings and go back to a male life. The problem was, deep down I knew purging was not going to solve my transgender issues. Plus very certainly, I was getting no closure and I would always go back to the mirror.

Through it all, I was very naïve and thought closure was around every corner as I continued along my gender path. It turned out, all the small victories I celebrated had nothing to do with winning the war and having any closure at all. The prime example I can recall came when I decided to transition from a cross dresser to a transgender woman. When I was beginning to be successful, I thought I finally had it made when something came along and changed my mind. Foremost among life changing closure experiences occurred when I learned what my second wife warned me about. I really had no idea of what a woman went through in life and I had to learn before I could be accepted. 

I needed to lose my impostor feminine syndrome on several levels. Even though, I couldn't have things such as periods and pregnancies, I had other problems to deal with as a transgender woman to pay my dues. Primarily, losing all my male privileges was what I gave up first to join the world of women. I didn't expect any special privileges to be let in, I just wanted to be given the chance to let my feminine inner soul flourish in the world. She waited nearly a half a century to live and had learned a lot. Even still, I was viewed with a certain amount of mis-trust by several women who I think thought I could run home and go back to my old male life. There was no easy way to prove to them I had given all my male clothes away and there was no turning back for me. 

Once I broke down gender doors thanks to the help of certain close friends, I was able to enjoy more and more activities such girls nights out without impostor syndrome setting in. Finally, I was feeling more and more closure from my old male life. In many ways, I had insulated him from myself altogether. Even more so when I started gender affirming hormones and started to feel the full effects. I started to understand aspects of a woman's life such as emotions all the way to simple things such as the influences such as temperature changes on the body. Suddenly, I discovered women were not just being sissies when they said they were cold all the time except when they were having hot flashes which I went through also. 

As I was going through all the changes in life hormones sent me through, closure set in and I knew there was never going to be any going back. It took me awhile to realize the closure I was attempting represented the most intelligent decision I ever made with my life. I didn't have to worry about any more impostor syndrome because I knew I had paid my dues. 

Now the closure I need to look forward to is doing whatever I can to insure my final years are as smooth as possible. Much of it will be out of my control so I will just have to do the best I can try to pay it forward with organizations such as the "Alzheimer's Organization." My Dad passed from a very ugly case of Dementia years ago, so I hope I won't have to put my loved ones through the same thing. The rest, however is mainly out of my control with no chance at closure. 

Transgender Expectations

 

Picnic Image. My wife Liz on the right.

When I began the long and very difficult transgender journey I decided to take, I had many expectations.

At the time, I was still entranced with wearing all the pretty clothes a woman had access to. I could not wait to have my own wardrobe which would match any occasion from casual to formal. I was very naïve back in those days and thought a woman's life was all about how she looked. I was so wrong as I discovered as I explored more and more of a transgender woman's life. In addition to the layers cis-women went through in their lives, trans women face all of those and more. To begin with, we don't have the benefit of growing up around other girls and learning from them. Making our own way was difficult when the only input was coming from the mirror. 

Loneliness ruled my feminine side all the time my male side was trying his best to survive in the world he never really felt comfortable in. As I observed all the girls around me, my expectations of what their life was all about just increased. The problem was I had a distorted view of everything feminine. One example was I was shy and never liked having to ask a girl out on a date. I thought the whole process was so unfair just like worrying about serving in the military and getting shipped off to Vietnam. 

What I did not realize was the gender grass was not always greener on the feminine side. Was it easier to be the one asking someone out, or waiting for someone to ask you out. As far as the military went, there was nothing I could do about it, so I tried to hide my resentment and move on. 

As I did move on, I discovered many other expectations I never planned on. Communication was one of the major hurdles I needed to overcome before I could learn to live a quality life as a transgender woman. I was blindsided quickly when the public wanted to talk to me faster than I was ready to respond. Initially, before I went through vocal lessons, I tried to just talk in a soft background voice and hope for the best. Trying to match the voice to my appearance was not an expectation I planned on but it happened. It was just all a part of moving out of the mirror and into the world. 

As I matured as a trans woman and started to communicate with other women, I learned the grass was certainly not greener on the feminine side of gender. As I thought back to the Christmas envy I had because of my two girl cousins who were dressed in their new dresses and white tights. Liz ruined my illusions of pleasure when she told me stories of getting in trouble for getting her tights ruined by playing with the boys. 

Even though I found the grass was not greener on the other gender side, the more I learned of the gender differences I faced, the more I wanted to continue my journey. It seemed the more I experienced, I more I felt I had paid my dues as a transgender woman. More or less, as a rite of passage such as a mammogram. 

Since females are not born women but rather socialized into womanhood, transgender women have to go through the same process. By following all those expectations all those years, I finally arrived. The path I followed was difficult but in many ways the same as other women, transgender or not. 

Are You Really Someone Else as a Trans Person?

 

Image from Kevin Laminto 
on UnSplash

For the longest time, I considered the idea I was two separate people.

On one hand, I was living the male life I was entrenched in and on the other, I was attempting to carve out the precious time I needed to explore my cross dressing self in front of the mirror. Trying to live a life on the gender border between male and female as very difficult to say the least. When I was in male mode, I spent every spare moment wanting to cross dress again at the least and trying to imagine what living as a girl would be like the rest of the time. To make matters worse, I even dreamed of being a pretty girl when I was asleep. Then I had to wake up confused and bitter when I found out life really hadn't changed and I was still a male after all. I needed to go again and challenge an unwanted world. 

Through it all, I often wondered why me? It took years for me to embrace who I really was and know the answer. I was just me and it would have to be good enough. However, the family upbringing I went through made it so difficult. During my youth, I was taught nothing was good enough. When I brought home any "B's: in my studies, they were not good enough. Where were the expected "A's." The never good enough attitude carried with me into my cross dressing life, all the way to when I became a novice transgender woman. In other words, when I acquired a new dress, when its newness wore off, I always felt I could look better in another dress, It led me to being a thrift store shop-a -holic. I couldn't wait until I could take what I had set aside money wise from my wife and use what time I could set aside to locate the next great outfit. 

My problem became especially bad when I was able to afford shopping for new wigs. I went through what I called my clown era of wigs before I settled into one or two wigs I wore all the time. By doing so, I was able to finally begin to build myself as a stable transgender woman in the world. I was beginning to learn I was someone else and that person was not a guy. 

As I was doing all of this  and as I lived a new and exciting world as a trans woman, I found I was taking all the stress off my mental health. The new authentic me enabled me to feel more confident on the gender path I was taking. I was fortunate also to have had a good therapist at the time to help me talk my way through it with her. Since I had previously been diagnosed as being Bi-Polar, both of us were careful to keep my gender issues separate. Plus, no mention was ever made of me being two people. I set the idea aside as being yet another mistaken idea from my youth. It could have been my male self attempting yet another move to survive the onslaught of life changing ideas which threatened his very existence. 

My life today proves I was always only one person and that was my feminine side. It is so sad I needed to fight so long to feminize my entire life as a transgender woman. The only true person I needed to be.  

Opening Transgender Doors

Image from Nathan Wright 
on UnSplash

What is the old saying, "When one door closes, another one opens." I think the saying is especially appropriate for transgender women or trans men.

Along the way, I have documented several substantial times when I slammed doors during my past and opened new doors. 

Probably the first time I closed a door was when I was going out with a certain set of party friends who ranged from cross dressers to transsexuals who were planning their genital realignment surgeries. I wasn't very interested so much in the cross dressers but on the other hand, I was very interested in the women who were going "all the way." I wondered if I could ever slam the door on the male life I had fought to live and open a new door into a feminine world. 

Luckily I was able to see different sides of the gender coin so to speak. One friend in particular was a firefighter in Columbus, Ohio who was gorgeous and near retirement. So she had the financial risk of a gender transition covered as did the other main transsexual woman I knew at the time. She also was gorgeous and had a very secure job as an electrical engineer. She was so good at living a woman's life, she regularly went on snow skiing trips, spending whole weeks as her authentic self. So, as you can tell, I had lofty role models to try to live up to. I knew they would be difficult to match up to as far as appearance and income plus neither one had a spouse to deal with. I loved my spouse very much and wasn't sure I was able to close the door on my relationship with her. 

Even still, I continued to observe and learn as well as set out to open my own transgender doors. It just took me longer than others to find a path of my own. I know all too many of our gender journey's are similar yet so far apart. It is difficult to leave the first door in our closet and find the other doors in the darkness. Once I was able to find the light and it wasn't the train at the end of the tunnel, I was able to progress quite nicely but not without trepidations. Of course I still had to deal with the usual problems transgender women and men have to deal with when they transition and close the big door. Sometimes closing the door is the easy part compared to opening the doors to different living situations with family, friends and finances. 

I think too many potential transgender folk believe the transition itself will cause the life problems to go away and they haven't thought enough about the all the situations they would have to face now when spouses and/or families want to leave them behind. Not to mention the prospect of losing long term employment and friends. All of the process led to opening very heavy doors and not having much of an idea what the future held. 

I was fortunate when I finally had the courage to open my final transgender doors and face the world. As I did, I could look back at all the times I was petrified to try a new life as a transgender woman. Every time I was so scared it seemed I made it OK which felt so natural and gave me confidence to move forward and look for new challenges. I don't think I ever forgot the two early gender role models I had in Columbus, Ohio so many years before but similar to my male life, I was able to carve out my new life as a fulltime transgender woman so different from theirs.

Even still, I have my doors to open as I face a challenging future with end of life issues. I am still paranoid concerning facing the problems associated with nursing care or assisted living. It will be quite the journey as I face the final door we all have to open and see what is on the other side.

Prom Time

 

Image from Amy Kate
on UnSplash

I graduated from high school way back in 1967 and where I went to school in Ohio, going to prom was a big deal.

I was very shy and as it turned out my junior year in high school prom was my first date with a girl ever. I didn't even really ask my date out, it was pre-arranged by her friends who knew she did not have a date nor did I. So I was set up for success. 

Of course success for me was scary. I had no idea how I could ever spend an entire evening with a girl. What would I say? How would I even communicate? The only real interactions with girls were with my Mom. All others just seemed to be up on a far away pedestal I had invented. Then my gender issues came crashing in to make my problems even larger. All I really knew was deep down inside, I wanted to be the one wearing the pretty fancy gown rather than the restrictive monkey suit called a tuxedo. Worse yet, I had to spend my own hard earned money to rent a tux. 

It turned out renting the tuxedo was only the beginning of my expenditures. I was fortunate at the time to have had a very well high school paying job so my parents did not have to contribute much to my initial adventure with a girl. In order to go all out for the evening, tradition was the guy paid for nearly everything from flowers, to dinner at a supper club, to tickets to the after prom which was a way to spend the entire night out. What I didn't factor in was how much my date had to spend on finding a dress, having her makeup and hair done and of course locating matching shoes. All of the processes the girl went through for prom to me felt like a labor of love to me I couldn't have waited to try. 

My date's parents were doctors so Dad even went the extra mile and let me borrow his car for the evening. Needless to say, I was scared to death in my tux when prom time approached. Somehow I managed not to blurt out anything stupid when I was introduced to my date and let her Mom put the corsage on for me on my date's spaghetti strapped gown which I loved and told her so. Just didn't happen to mention just why I loved her dress so much as I wondered how it would look on me. Fortunately, we were meeting another couple for dinner, so I didn't have to feel so stressed about carrying any sort of a conversation myself. So far so good, my first date was coming off without a hitch and ironically I was able to experience some sort of transgender revenge when I went to the old supper club when it became a gay venue. I was there one night and was able to use the women's room completing some sort of gender circle in my mind.

By the time my senior year rolled around, I was a seasoned prom pro and ended up going to two proms in one night. Since I was dating a girl who went to a competing high school, we decided to go to both proms. I even drove my own car since she was familiar with it and I didn't have worry about asking my Dad for his car. Overall, I managed to have a good time since I wasn't so frightened of the whole experience. For the rest of my life, my prom experience was over. For better or for worse. 

Probably, my parents were relieved I was finally dating girls. I on the other hand wasn't doing anything to relieve my gender dysphoria. I still wanted to be my girlfriends and live their lives. My cross dressing tendencies continued all the way until I was drafted into the military and had to stop for obvious reasons. By this time, I had more to worry about than how I looked as a girl. I was looking at surviving college so I could stay out of Vietnam as long as I could.     

Today I see the young high schoolers seem to view proms as less structured affairs than we did so long ago. It's all for the best.

Being Prepared for a Transgender Future

Image from Chad Walton
on UnSplash.

For nearly a half a century, I hid behind the idea I was nothing more than a cross dresser who liked to wear women's makeup and fashion. What harm was I really doing? The answer is, the only harm I was doing was to myself.  

Had I known all I was doing was to prepare myself to transition into a transgender woman later in life, I may had approached the process in a different light. The problem was, everything seemed to be so life and death serious. Primarily since I was locked into a very lonely, dark gender closet. I had no role models around me to prepare for a highly uncertain future. No one to tell me my make up looked clownish and my skirt was way too short. I only had my old male ego and a mirror who were teaming up to make my life miserable. 

I really learned how miserable I could be when I began to leave my closet and explore the world.  Being stared at and laughed at to my face taught me the mirror could lie to me and the way my old male self was telling me to dress was all wrong. I was going back to my cross dressing drawing board too many times before I learned what I had suspected all along, becoming a part of the feminine gender was going to take a lot of work. I needed to go so far to finally understand all along I was a woman cross dressing as a man and not the opposite. 

The more I began to understand where I was in life, the more the future came into focus and preparations for major upcoming decisions became important. As I was exploring and building a new life as a novice transgender woman, it became clear to me I could indeed live my dream of living as a woman. Before I could arrive there, I still had heavy preparation work to do. There were major issues of coming out and telling what was left of family and friends I was a trans woman. Once I did, there would be no more running home and hiding in the mirror wearing a dress, The first person I told was my only child (my daughter)  went very well and I was emboldened to tell more people such as my only sibling ( a brother). He accepted my transness terribly so I ended up with an even split in salvaging any of the family life I had left since my parents had long since passed away.

The next crossroad I needed to navigate was what was I going to do about supporting myself in my new world. Following quite a bit of planning and preparation, I decided I was close enough to being able to take an early Social Security retirement which back in those days was sixty two. To get there, all I had to do was work another two years. Ironically, during the two years, I was able to prepare even further for my future when the Veteran's Administration Health Care System I was part of suddenly began to accept HRT or gender affirming hormones for veterans. So, the extra two years gave me the time to further prepare for a future which included changing all the legal gender markers I could including a new legal name. 

Since I was newly single again following my second wife's sudden passing, I really could use the time to prepare for the final transgender transition into a new life I had been preparing for since I was born.  

You got it...Now Live with It!

 

From the Archives, Club Diversity. Columbus 
Ohio.

For some unknown reason, I have been remembering more and more what my gender therapist told me so long ago, she couldn't do anything concerning me wanting to be a woman. Now I don't remember if she told me I could not do anything about it either. 

If she did and had I listened, I would have saved myself so much inner torment over the years from my gender dysphoria. At the time my male self was not even close to being ready to give up any claims to his life which at the time was becoming relatively successful. After all, he had worked long and hard to arrive at the point where he was. 

If I wanted to blame anyone but myself for not accepting my true authentic self, I would blame my home environment. I grew up in a very male dominated family. My Dad had two competitive brothers and his competitive personality filtered through to my brother and I. It seemed no one had girls in the family and if they did, they were second class citizens. How I existed was by keeping my true feminine desires a deep dark secret. I learned early the very male trait of internalizing any negative thoughts or ideas. The whole concept turned out to be very self destructive over the span of my life which included the years of being a very serious cross dresser or transvestite. The whole process nearly took my life before I finally figured out I had it, now I needed to live with it. 

All I wanted was the impossible. Give me back just a fraction of the time and effort I had wasted by trying against all odds to maintain any sort of a male life. The cruel and unusual punishment came in when the more I achieved as a guy, made it more difficult to give it all up. I had a spouse, family, friends and good job to suddenly consider. What would my daughter think? Not to mention my wife and brother. All of a sudden I needed to draw a line in my gender sand and decide which route in life I was going to take. 

Everything changed for me the night I finally decided I had put enough exploration as my feminine self to make the ultimate leap over the gender border. Needless to say, it was a huge weight off my shoulders. I had a chance to go back in life to a point where I was not so jaded by either gender and experience for myself what the future held for me. It was at this point friends jumped in and showed me the way I never thought possible. I found I had it all along. I was a transgender woman and now I had the rare opportunity to live with it. I discovered there was so much more I needed to learn when I entered the world as a trans woman. 

Plus it took a while for the overall excitement of transitioning into my dream life to wear off. Everything I did was new and different and even when I was not accepted, I learned from my mistakes and for a change, my inner stubborn streak served me well. I had it and now I was living with it. I guess if you are able to live long enough as I have, you have the opportunity to see life go full circle. I paid my dues as a guy and what he learned turned out to be beneficial in my new life as a woman.

Quoting the singer/songwriter Joni Mitchell song "Both Sides Now",  only when I was able to see the world from both sides of the binary genders, was I able to relax and enjoy my life. All along I had it and just missed out on the real possibilities of what I was missing. Living with being transgender was all that mattered.

Life's Little Nudges

Image from James Lee
on UnSplash

In an extension of yesterday's post, there were many times when I needed a little push to keep going towards my dream of living a life as a transgender woman. 

Perhaps the first push I needed was I had to know if I could exist in the public's eye as a novice cross dresser (or whatever label you want to put on me) at all. It seemed everytime I left my closet, I was being laughed at or at the minimum stared at. It was during those dark days I waited on any rationalization to come along to justify what I was doing to myself was right. The light I saw at the end of the tunnel certainly seemed to be the train back then. 

Somehow, I kept dodging the train and relied on the least bit of gender euphoria I felt on occasion to propel me forward. One example was the short, flirty tennis style outfit I came up with to wear to the mall. I managed enough pizazz to generate admiring looks from many of the old men who were in the mall walking at the time. Back in those days, I didn't really understand what a true validation as a woman meant to me. I was still obsessed with appearance only.

Slowly I was nudged off my appearance pedestal by comments from my second wife such as I did not have any idea of what being a woman was all about. Since I had spent nearly all of my life to that point studying the women around me, I resented the fact she said it at all but even still, I set out to find out what she meant. Sadly, most of what I learned from her comments did not come until after she passed away. At that point, gender doors began to open for me and I was nudged through them. Finally, I paid enough dues to be allowed to play in the girls' sandbox. Where the real learning started. Slowly I survived having my sandcastles destroyed and sand kicked in my face by the mean girls and I moved on.

As my world widened and I actually learned I could make it in a transgender world, it seemed each night was a bigger and bigger push in the right direction. Destiny showed me a path and I took it. My small group of lesbian friends showed me how to validate myself without a man and secured once and for all my sexuality. I was living my dream and decided to take it a step forward by beginning gender affirming hormones. After all, at the age of sixty, if I was healthy enough, what was holding me back. It turned out nothing was except for a surprising reaction to the new femininizing hormones in my body. It was much more than a nudge when my breasts developed to a point where they were easily visible under all my old male shirts. All along, I thought the process would take longer but it didn't and it was time to come out to what was left of my family. 

The coming out process showed me both sides of coming out as a transgender woman in a male dominated family where I was supposed to be the patriarch. Because I was the oldest surviving man. My brother rejected me and my daughter accepted me is the short and sweet version I relate to so much here in the blog. 

Even though it was at times a very difficult and rough gender journey I went down, life's little nudges made my life anything but boring. In fact, it tended to be on the terrifying/exciting side.   

Somewhere between Heaven and Hell

 

Image from Sara Kurfess
on UnSplash

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

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

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

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

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

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

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

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

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