Having Fun????

 

Image from Jarritos Mexican Soda 
on UnSplash

Depending upon which label you use, transgender or cross dresser, when you reached the heights of dressing yourself as a woman, did you ever feel as if you were having fun?

I guess before you can answer the question, you have to define what fun is to you. To start I went to a popular well known source for an answer and it said whatever provides amusement or enjoyment. At that point I began to think at what point did I achieve either amusement or enjoyment. Although I couldn't remember many times I was amused with my life as a serious cross dresser or novice transgender woman, there were plenty of times I enjoyed myself. Even though many moments of gender euphoria were rare. However rare, there were enough moments to encourage me to move forward in the world I wanted to create for myself. 

There were many times my old male self filled in the blank spots in my life as he always did. To him, he rarely enjoyed anything and was amused by less than that. I can blame my parents on how I was raised to feel nothing was ever good enough, I could always do better. There was never time allowed for fun or enjoyment when I was moving on to the next thing.  My male life carried over to my earliest cross dressing days when I always thought my next outfit or wig would allow me to present better the next time I went out into the public's eye as a feminine person. Even on the rare times I was successful in my transgender quest, I never allowed myself a moment of fun. 

During that period of my life, like most people, I thought I would never be old and wrinkled and my idea of having fun would change. Even though, unexpectedly, the introduction of estrogen based hormones into my system plus the blessing of good genetics, allowed me to continue the partying lifestyle much longer after I should, sooner more than later I needed to calm down. In order to save my body the best I could, I needed to cut back nearly entirely my alcohol consumption. On the other hand, as I reached my mid seventies in age, I needed to find activities to motivate my mind and body as I approached the end of my life. 

What I decided to do was continue to write the Cyrsti's Condo blog on two on line platforms now and on the other hand try to push my body to do more walking. Since my Dad began to give up on himself and retire to his easy chair later in life until dementia ultimately led to a very ugly death, I figured even though I couldn't enjoy the same aspects of life I didn't take the time to savor when I was younger, I try to set myself up for the future and enjoy what I have. Such as the rare accepting cohesive family I am so fortunate to have. I cherish the relationship I have had over the years with my wife Liz as well as my daughter Andrea. 

Even if I am not having fun as such, being able to lead a life as a fulltime transgender woman is special to me. I try to always remind myself how truly special it is to lead the life I do. 

It is always special to me that all of you take the time to stop and read my blog. It means so much to me and thank you.

  

Eating our Young

 

Image from the Jessie Hart
Archives...

Recently I read a lengthy comment on social media from a current board member of the transgender-crossdresser local group I am part of. 

In essence, the post was about so called meddling with the current board of directors from "retired" board members. In many ways the whole meddling process is a continuing system which tears apart the transgender community. A primary example is the "I'm more trans than you" sad logic which too many people try to subscribe to. Sometimes the idea is born when someone has more gender surgeries than another transgender person. Over the years, I encountered push back questioning my transness simply because I hadn't undergone any gender surgeries at all. They looked at my choice as some sort of a gender negative. In response, my friend (also a transwoman) and I used to refer to the naysayers as "Trans-Nazi's". 

Backtracking just a bit, the local group I have been a part of for years seemingly goes through a push to tear it apart every so often by well meaning people. My prime example came  years ago when a far-right leaning transgender woman was pushing her views into the group, which initially kept me away. Predictably, during the pandemic she refused to be vaccinated and died from Covid. 

Since it is a volunteer organization, it is difficult to find people to step up at all. Especially if there is any friction at all. In many ways, I think the problem stems from a deeper problem which comes from lingering systems of having a male ego. Some are jealous of other transwomen who may be more attractive or have other problems with their personality. Since all of the sudden, people with such diverse backgrounds are brought together under often a vague umbrella called transgender. The expectations are often unreasonable. 

The problem is the whole scenario effects the solidarity we all LGBTQ+ individuals need to combat the surge of anti-transgender bills around the country. I am still amazed when I encounter the occasional transgender person (or mostly cross dressers) who still support the political party which is not the Democratic one or a candidate which supports doing away with our existence all together. I can't fathom their thought pattern.

At this stage in my life, I rely on my writing to do my outreach. Through my contacts with the Alzheimer's association, I am being contacted by another group for an interview of some sort. I look forward to being able to spread the word of diversity. 

In the meantime, I hope the local trans-crossdresser group can heal their spat and move on for the betterment of us all.  

At the Crossroads

Image from the
Jessie Hart Archives

As I continued along my gender path to living as a fulltime transgender woman, I arrived at several crossroads. 

The first of which was finally deciding I was transgender at all. For years I considered myself nothing more than a very serious cross dresser. Perhaps the biggest positive aspect of staying a cross dresser was my wife knew of my gender pastime before we were married. She even grudgingly bought me gifts such as woman's clothes. In fact, we had a separate gift exchange at Christmas every year especially for my feminine self. 

On the other hand, my wife was totally against any idea of me being trans, saying she didn't want to live with another woman. I had no comeback for that argument since she did marry my male self. Still it did not stop me from exploring ever further the feminine world I thought I wanted to live in. As I did my explorations, the process felt so natural I just had to keep going. At the crossroads I decided I was indeed transgender and I was pursuing a lifestyle not just participating in a hobby. From the point forward my life changed and I had many new decisions to make.

Decisions such as how would I even structure a totally new life in a woman's world. Along the way, I learned the possibility of living as a trans woman meant so much more than just doing my best to present well in the world and blend in with the public. What would I do about the three "F's" as I called them, or family. friends and finances. At the time, I didn't have the answers to many of the questions so I kept searching. Of the three challenges, I decided to come out to my family first and see how it went. When I did, I received a fifty-fifty split in return. By this time in my life, my close/blood family had been reduced to two people. My daughter and my slightly younger brother. As it turned out, my daughter was very supportive and my brother was just the opposite. I tell the story often how I gained a family with my daughter's in laws and lost my brother's family at nearly the same time. Sadly, it all happened over a decade ago and things have never changed.

The next step I needed to consider at my crossroads was what would I do about what friends I had left from my old male life. Again, sadly, I had very few close male friends and had lost most all of them to death in a very short period of time. So I had very few friends to tell. No worries since I had never been able to make since seemingly I kept pushing people away my entire life because of my gender issues. I thought the fewer friends I would have to tell, the better off I would be. 

On I went at my crossroad when I came to the third "F" which was finances. I obsessed on what I would be able to do to support myself. I had built myself into a successful well paying job which I knew would be impossible to transition genders on while I worked it. What did work in my favor was my age. I was close enough to to retirement age to consider taking an early retirement. Which meant all I had to do was work a couple more years and then not have to worry about transitioning on the job. 

What ended up happening was, I painted myself into a corner I couldn't get out of. The pressure grew so intense as I tried to live both as my old male self and my new feminine self. It literally tried to kill me before I said enough was enough. One night as I sat alone and pondered what I was going to do, I finally decided to do the right thing and give up totally my old male self and live as a transgender woman. 

From that point forward, I felt as if a giant weight had been lifted off of my shoulders. I had made the correct turn at the gender crossroads and was able to move on with a new life. I waited for the paint to dry in my life and gently learn to live as my authentic self.   

Night Moves

 

Image From 
the Jessie Hart
Archives

With all respect and credit given to singer Bob Seger, one of the line in his "Night Moves" song particularly resonated with me. Seger sings about having a 1960 Chevy which I had one also. Plus, I even copied Seger's lead and made out with a girl in the back seat. 

Basically, the basis of the song has to do with his early learning relationships with girls. Other than the connection with the car, I immediately made another connection with me being a transgender woman. Since I had many years to live as a heterosexual man, I had big sexual questions to answer when it came to my future feminine life. 

At the time I was coming out, I had certain cis-women friends who automatically assumed I would move my sexuality with me into all of a sudden being attracted to men. I worried how my new sexuality would effect me because I knew gender was between the ears, or in the brain, and sex was between the legs. It turned the sexuality did not matter that much to me after all. 

In order to understand where my sexuality would ultimately end up I needed to work on my own night moves. Very quickly, I found out women would still be in my future. As it turned out, not only was I going out by myself as a woman in sports bar venues (which was hard enough), I was going out as a transgender woman. Which meant greater expectations of what my night moves could mean. Along the way, I attracted very few men but on the other hand, I was approached by more women than I had ever experienced in my life. Going out to be by myself was quickly proving to be more of a failed theory than a fact. The public, mostly women, wanted to interact with me.

Of course at that time, I wasn't looking for a sexual relationship of any sort, so I didn't have any night moves at all to work on. Other than attempting to appear as presentable as I could. If I was approached by the rare man, I considered myself validated as a full fledged transgender woman. All the way to the times to I actually had dates with men. Plus there was a guy, if I had the time and would have put in the effort I could have seen myself going farther with him. The fact still remained I had no experience with flirting with a guy and all the experience flirting with another woman. 

By pure chance, all the cis-women who I became close to turned out to identify as lesbian. I think it happened for a couple of key reasons. The first of which was curiosity. The women were all curious why I wanted in their world at all. The second is I was still a mixture of some sort of a hybrid gendered man. I was certainly more mellow than any man they ever met and never made any sexual advances to speak of. I worked hard to not be the guy I didn't ever like. 

Embarking on hormones very much did away with any sexual advances I could ever consider as a so-called normal man. My doctor who initially prescribed my HRT told me was I OK with losing any sexual contact I had previously enjoyed. It didn't bother me because when I had sex with a woman, I always imagined I was a woman too.

I guess you could say since I was too shy to start dating until later in high school, I didn't have much experience with many night moves at all. What I did have was with women and it turned out it was all I needed. 

Intersections

 

Image Courtesy Transvestia Magazine

Over the years, I have realized I have experienced several important intersections in my gender development. 

Perhaps my first intersection came when I initially glimpsed my image as a girl in a full length hallway mirror I had at home when I was growing up. I was enamored and immediately wanted to do more. I was hooked to the point where I knew I wanted to do more than just look like a girl, I wanted to be one. Which turned out to be the first indication I had I was more than a cross-dresser, I was transgender. A key intersection into my future.

As I grew up, I faced the same problems other gender dysphoric youth faced too. Our gender closets were very dark and lonely. Particularly in the pre-internet and social media era. Many of you remember when Virginia Prince and her Transvestia publication intersected our lives and we discovered we weren't alone in the world. For me it was a life changing experience when I began to regularly receive my bi-monthly issue of the publication. Of course I wanted desperately to look as good as the models I saw in Transvestia. 

The next major intersection of my gender life came when I started to attend transvestite mixers I read about. Finally, I could meet like minded cross dressers and see what they were up to. What I discovered was a multi layered group of people who were much more diverse than the run of the mill cross-dresser.  I was very enamored with the group I called the "A" listers. Most of them were impossibly feminine and headed towards gender realignment surgeries but others weren't and even brought their girlfriends or spouses. Deep down, I knew where my intersection needed to be, I wanted to hang out with the  "A's" . Just not share their often arrogant attitudes. Even still, I felt I still didn't fit in with either of the groups. I wanted more than just looking like a woman or going under the surgical knife to somehow prove I was a woman. 

Even though I have been able to maintain my attitudes concerning gender surgeries to this day, none of it applied to the decision I needed to make when I approached the choice of undertaking hormone replacement therapy. Again the intersection of my gender life took over and I went to a doctor to be checked out and approved for my hormones. Finally I was on the external and internal gender path I wanted to be on. Externally I was feminized to help me get by in the world as a transgender woman and surprisingly there were many internal changes also. I intersected with my deep seated feminine self and suddenly I was able to feel the world in ways I never thought possible. 

Excepting gender surgeries I never had, I was intersecting with the world as my authentic self in ways I never thought possible. My days living in the mirror and wishing I was a girl were coming true. 

Under Twinkling Holiday Lights

Image courtesy Clifton Mill 

In my past, when I was progressing down my very difficult gender path and leaving my old male self behind, I began to try to experience new and exciting things. 

Part of my plan was to experience activities I enjoyed as a man and experience them as my new feminine self who was enjoying the time in the public's eye. Keep in mind she did not  know how being in public would work at all. She had so little time having done it. 

One of the activities my second wife and I enjoyed doing on a regular basis was taking the short trip to a vintage working grist mill It has become famous in the area for it's Christmas decorations To put it all into perspective, the venue says there are four million lights although I don't know who is patient enough to count them all. None of that mattered to me as I planned for my chance to experience life as my authentic self which was becoming much more than an impossible dream. At the time, my second wife had not passed away as yet and I was very much sneaking around behind her back when I cross dressed as a woman and left the house. I arranged my work schedule to have a rare Friday night off, knowing she would have to work because she was in retail as a manager of a major book store. My plan worked to perfection and in the holiday season hustle and bustle she indeed had to work. She knew all along of my cross -dressing desires but drew the line at me going public as my feminine self. 

As the time went by, I needed to plan what I was going to wear for this all-important evening. I needed to plan for the weather and for my comfort at the same time. I knew the parking situation at the Mill was not the best and I would need to walk a distance to see the lights and holiday displays. For the evening, which turned to be an ideal mid-December, chilly winter evening. The moon and stars were out and I was ready for the magic which was coming my way. But first things first, I had to choose my warmest, fuzziest sweater, leggings and comfortable boots which were suitable for walking. After putting on my clothes and makeup I thought I looked the part of an upscale woman out for a night at the Mill. Little did I know how wonderful the evening would turn out to be. Under the sparling stars and twinkling Christmas lights I finally would have the chance to live as the feminine transgender person I always felt I could be. 

Of course, the first obstacle I needed to conquer was the fairly simple task of stopping and waiting in line for a much-needed hot cocoa with marshmallows. Once I reached the front of the line, I was so nervous, I could barely order. I summoned every ounce of my courage to tell the woman behind the counter and in a low voice ordered my beverage. I was happy and my confidence grew when she smiled at me, took my money, and gave me my drink, and she even wished me a Happy Holidays.  From then on, I had to make a conscious effort to slow the evening down because I was moving so fast and not enjoying the moment as much as I should. From then on I slowed down and enjoyed being in the public's eye as the feminine person I always wanted to be. To celebrate, I even splurged and stopped at another concession for hot cocoa. 

What I remember the most about the whole experience was how heightened my senses were. The lights were brighter and twinkled even better than before. The only thing missing was a visit from Santa Claus himself. He was scheduled to appear later, much to the joy of all the kids in the crowd. In the meantime, I was able to shop the Mill's gift shop but could not buy anything for several reasons. The main one being having my wife questioning what I was doing there in the first place without her.

Before I knew it, I had seen all the animated attractions, plus the Santa doll display. All in full view of an accepting world which was a first for me. From that point forward I had the confidence to do more and more towards exploring the world as the person I always wanted to be. When I had the chance, I started to do the rest of my Christmas shopping as a transgender woman. I look back on my trip to the Mill as the beginning of a wonderful lifetime transformation. I discovered I could be me no matter how difficult the path may prove to be. Discovering the basic differences, the binary genders deal with was a major path to follow.

In many ways, the excitement of the first evening under the holiday lights would be a wonderful beginning to the life I was always destined to live. It was never as easy as walking among the crowds of people un-noticed sipping a hot drink, it was enjoying the totality of being myself. Which would become so increasingly complex as the years progressed in my life. All in all, the holidays lights were a wonderful, even magical beginning to a better life. Without knowing it, I was giving myself a wonderful holiday gift my inner self was wishing for. 

Sadly, time was up too soon and I had to head home to beat my wife there as well as take all vestiges of my makeup off my face. I knew one thing; I couldn't wait to experience such a fun night out again.  

Fear as a Motivator

 

Image from Amanda Jones
on UnSplash

Most of the time I can't remember the number of times I was paralyzed with fear as I pursued my gender path from a serious cross dresser to novice transgender woman. 

Examples include nights I sat in my car sitting in fear trying to figure out if I would go into the venue at all. Some decisions were easy such as entering gay venues but others were much more difficult.  Along the way also I made poor choices on which venues I was trying to go into which caused me to have more fear in the future. Mainly when I tried to visit redneck-ish places to see if I could present well enough to be accepted. The end result a couple of times were not good when I had the police called on me. I learned my lesson and was much more selective on where I went. It worked and the power of my fear was ultimately rewarded when I discovered venues where I could relax, have rest room privileges and become a regular patron.

There was a time when I considered the rush I received when I conquered my fear was a primary reason I cross dressed at all. Of course I finally realized fear was not why I wanted so badly to be a woman. The entire process went much deeper than all of that. What it did do was encourage me to go farther down my gender path. I set up goals I wanted to achieve. When I considered fear as a factor in future cross dressing decisions, it soon was reduced to just being nervous. Ironically, being nervous still sticks with me to this day. I need to push myself to certain restroom decisions because years ago, choosing the women's room was the primary reason I became a target of the public. By years ago, I mean the last time I experienced any restroom problems was nearly three decades ago but then again I am still nervous even though I know my way around the etiquette of using the women's room.  

Eventually I began to understand fear and used it as a powerful motivator. When I was considering not going to a party or a new venue I use fear as a reason to move forward. Of course now since it is rare I go anywhere without my wife Liz, we make a couple which keeps most transphobes at bay. 

Since I am mentally predisposed to having anxiety, I still have a tendency to worry about things such as me being mis-gendered again at my upcoming colonoscopy. Even though I keep thinking if that is all I have to worry about, I really don't have any issues at all...relatively speaking. I better begin to worry about the results of the exam as well as the unpleasant prep process I will have to go through before hand. 

It has occurred to me also, maybe I should have done a better job separating fear with excitement. My earliest days of exploring the world as a transgender woman were very exciting and the fear on occasion was a powerful motivator to conquer the gender anxiety in my life and move on. Plus, overcoming my fears gave me the all important confidence to move into a transgender life.  

Owning It.

 

Image from the Jessie Hart
Archives

Long ago I learned the hard way the power of owning my public appearance as a novice transgender woman or very serious cross dresser. 

I was tied too closely to my mirror and didn't realize until it was too late how it could lie to me. Examples included how the mirror told me I was an attractive woman who could go anywhere just to be bounced almost immediately by the public. Many times I would come home in tears wondering where I went wrong. Finally I came to the conclusion I was putting my feminine priorities in the wrong place. In reality my mirror was not in my house but was in the public's eyes. When I learned to dress to blend in with the other women around me, I began to own my existence as a transgender woman. No longer did I have to worry as much about being laughed at in public. 

Also, when I owned my life as a trans woman, I gained the all-important confidence I needed to follow and improve my right to exist in the world. If someone had a problem with me, it became their problem, not mine. The biggest pressure I faced was needing to communicate with the world as my transgender self. Suddenly the process went way past how I sounded into what I was saying. Owning the new gender world I was in meant learning to operate on an entire new spectrum involving an internal look at how the two main binary genders (male and female) communicated. Quickly I learned why men and women couldn't connect on the basics of communication. I learned also both genders put up a sort of invisible barriers when it came to talking to each other. Ironically, I began to be asked by each gender why their spouses or partners didn't understand them. 

I truly didn't find out why I had a key insight into both genders until I was allowed by other women into their world of life and communication. I learned the power of non-verbal communication as well as the seismic power shift between the genders. Basically the process is very simple. Men deal with power systems such as money and athletics when women deal with a more passive aggressive world. I was fortunate in that I was aware of how women formed smaller cliques (not teams like men did) and reacted passively aggressively to those with power. Such as management. When I was in my male management days, I learned the hard way if I wanted something done with my female staff, first I had to sell it with just a few key women on the staff.  Dealing with an alpha female was much different than an alpha male in more than the obvious ways. The ways I needed to learn if I was ever allowed to completely be welcome in the women's sandbox. I needed to win over the alpha females first.

I made it when I paid my gender dues and was able to own my life. The confidence I live with now is but a side benefit.

A Night at the Orchestra

 

Cincinnati Symphony Orchestra

Admittedly, my life as a music fan had leaned towards the classic rock genre. The closest I had been to a concert venue was years before when I went to a Halloween late night silent movie horror show dressed as a shabby prostitute. Now...

When I began to seriously date and live with Liz (now my wife), she expanded my horizons since she was a fan of all sorts of music including the classic and or orchestral scene. It turned out, she wanted someone to go with to see the Cincinnati orchestra's holiday concert. Without thinking of all the ramifications, I quickly agreed to go with her. 

The ramifications I am talking about were back in those days, I was still very much a novice as a public transgender woman. Plus I didn't have anything to wear to an event which ranged from semi-formal to formal. To find something to wear on a very limited budget, I set out on the improbable task of finding an outfit in a thrift store. Amazingly, I did find a black, very sparkly long dress which I could wear with a fringed shawl and for better or for worse I was ready to go. I finished off my black formal look with black tights and comfortable black flats for walking. Once my outfit had been decided, the toughest part was yet to come. 

Getting there was a different story. As I remember, public transportation was available for us to come close to the Music Hall where the performance was to take place. As always my limited mobility issues were a problem as we needed to arrive as close as possible. Plus, by using public transportation we could save money also as Cincinnati has a street car which runs close to the front of Music Hall but it didn't run late enough to help us in the return journey. What we did was decide to do was hail a taxi cab to take us to our next stop. Once we had the logistics of arriving and departing the concert, I needed to concentrate on the paranoia I was feeling about facing the public as a transgender woman in a totally foreign situation. 

Very soon, it was time to attempt to put my fears behind me and enjoy myself. Regardless of my fears, I think most of the public at the concert were in their own worlds and not mine. When that realization sat in, I was able to be impressed by the musical concert. It certainly was not all about me. 

The next stop for our evening was going to be a bit more difficult. First, we had to negotiate a crowd of people attempting to hail a cab. Our second stop or venue was approximately ten or more blocks away and was a place we had been to before so I felt comfortable ahead of time. We had a great time again and all to soon it was time for the trip home. Since we did not want to drink and drive, we ended up taking an Uber ride home. 

After the concert experience I had, I considered it one of the most defining experiences of my novice transgender life. I learned I could put my fears behind me and live a life I had always dreamed of. Overall, I had a great time and experienced a night I will never forget and for the year put me in a first- class holiday state of mind.