An Opportunity or Challenge

Image from Dylan McLeod 
on UnSplash

If you are similar to me and if you had a quarter for every time you heard a so called problem was no more than an opportunity to improve, you would be wealthy.

As I moved forward down my gender path, I found an increasing number of opportunities. As I mention often (or all the time), I had a difficult time adjusting to how I should try to present myself as a novice cross dresser. All outfits which included too short mini skirts or shorts were out. In place came a more conservative wardrobe which I found I could blend in with the other women I encountered. The challenge or opportunities I encountered were exciting yet terrifying. 

I had many firsts to deal with in my wide wonderful new feminine world. Many of the firsts I encountered, did not go smoothly and I went home sobbing. When I did, in the safety of my own home, I took ownership of the damages and attempted to build a plan to do better in the future. I went through every opportunity to improve such as better makeup, wigs and wardrobe as examples. I was very focused on the entire process. To the point, I had a difficult time when I still had to function as my old male self. I experienced a new challenge to stay in cross dressed mode when I flipped my gender script. Slowly but surely I was spending more physical time as my feminine self. It took me years to realize I was a woman cross dressing as a man. Not the opposite. 

Then, when I really started to seriously cross the gender frontier and deal one on one with the public, other opportunities or challenges became important. By this time, I was becoming very courageous in how I lived my life. I sought new venues to see if I would be challenged as a transgender woman. Some worked out and some didn't, so I crossed many off of the list. Many of the opportunities became challenges back in those days when I first began to seek access to women's restrooms. The whole process was an overall success with some notable failures when I had the police called on me. Still I persisted and earned my rest room privileges the hard way by learning the etiquette involved with using the women's room. Such as always looking other women in the eye, not putting my purse on the floor and pausing to wash my hands (no matter how much attention I was creating) among so many other nuances I was learning. To go into it all would entail a whole different blog post.

Another huge challenge or opportunity I faced was when I decided to begin gender affirming hormones, formerly HRT. There was no way I could anticipate the changes by body would go through. Both externally and internally as I was suddenly seeing the world in a softer version of it's former self. My sense of smell heightened and my thermostat changed as I became colder easier are just two examples. All in all, my body took to the changes easily and I felt as if I should made the change years before I did.

If I had utilized all the time and energy I needed to overcome the challenges of changing my gender and put the energy into my male self, how much farther could he have gone. The end result was so powerful, there was no way I could ever look back and change my reaction to anything.  

The Elephant in the Room

Halloween Girls Night Out
Kathy on left. 

Many times in my life I have felt as if I was the elephant in the room and it had nothing to do with my physical size. I was a pretty good sized man at around six foot tall and two hundred fifty pounds which kept the bullies away when I was younger so I wasn't a huge man.

All my problems began to surface in my unwanted male life when I went to family events and felt strangely out of place. As my male self I was the elephant in the room, or you could refer to it as the impostor syndrome. All along I was a woman pretending to be a man. 

As life went by and I had more experience presenting in the world as my authentic feminine self, I felt even more out of place at family events such as my brother's house. It was the place we always gathered for big sporting events with him (my only sibling) and his two sons. All was good until I started my hormone replacement therapy and started to appear decidedly more androgynous. Even then, before my breast growth started to happen along with me being able to grow my hair long, I was able to wear a loose fitting shirt and tie my hair back to still remain vaguely male. My last attempt "purging" my feminine self came approximately six months before my second wife unexpectedly passed away from a massive heart attack. 

As I "purged" I vowed to grow a beard which would make it technically impossible to go out dressed as a transgender woman and/or cross dresser. It worked and I was extremely unhappy but my macho cooks at least responded in a positive way, saying I looked more "masculine." Not a compliment I wanted to hear, 

One of the first things I did after my wife's death was shave off my beard and resume attempting to learn more and more how to live a feminine life. When I did, I learned my size could be dealt with and it had nothing to do with being the elephant in the room. In fact, during a couple of my initial girls nights out, one woman acquaintance in the group was even bigger in size than I was. I finally figured out it wasn't so much how much bigger than most women I knew, it was so much more important how I carried myself, as well how well my fashion sense blended with the other cis-women around me.  

However, there were many times when I still did feel like the elephant in the room, when it came to be invited to other girls nights outs. One night in particular comes to mind when I accepted an invite to go with a group of servers and bartenders to party one night at another close by venue. Even though I was warmly accepted in the group, I couldn't shake the idea I just did not come up to their level of attractiveness, which included size. I finally concluded there was nothing I could do about it, relaxed and had a good time. For the most part, they were surrounded by guys trying to pick them up so I very much just faded into the background anyway. 

As with anything else in life, a person has to take the good with the bad. In the long run, my body has provided me with a successful base to operate from. I was big enough and barely athletic enough to keep the bullies away and not too big and masculine I could not squeeze myself into women's fashions. I guess you can say, my elephant ran enough interference for me to get by until I could establish myself as a transgender woman. 

I was the elephant in the room and felt it on many occasions as a impostor man and a trans woman. I lived to tell the tale...so far. 

A HUGE Relief

 

Image from the Jessie Hart
Archives 

What a huge relief it was when I finally decided I was living a lie barely surviving  as a male person. I remember the evening vividly when I made the decision years ago.

Even still, It took awhile for my male self to gave up and concede all along my feminine self was cross dressing as a man and not the opposite. His ploy was he was cross dressing as a woman to relieve stress or whatever the current excuse was,  because there were many. Such as was I just pursuing a fetish or some sort of a hobby such as golfing. Needless to say, in a short amount of time I discovered I had mush deeper issues when it came to dealing with my gender dysphoria. My desire to seek out the truth kept me searching for nearly fifty years.

The search also wrecked my fragile mental health along the path I was pursuing and I regularly sought out therapy for answers. On occasion, I felt better after visits with my therapist but overall my feelings never really improved. Mostly because I was not facing the truth I had always known but was afraid to face. I never was the man I pretended to be. 

Life became especially difficult for me when I grew older and friends, family and spouses began to pass away. When each death happened, it was like my feminine self was asking when was it going to be her turn to live before it was too late. Still I kept on searching, unwilling to totally give up on the male life I had built. Finally, when I was living my life torn between the two prime binary genders, it all became too much for me to bear. Either I needed to end it all and indulge in self harm or in a sense give up and do the right thing. Which was begin to live a full-time life as a transgender woman. What a HUGE relief it was. As I gave complete control to my inner woman, it was as if she had been watching and learning from the world the entire time I tried to hide her.

It turned out, all the days and nights I was so paranoid about facing the world turned out to be unfounded because I relaxed and let her take charge. The more my old male self stayed out of her way, the better she did. The prime example was appearance. She followed the basics of establishing a fashion sense which blended with other women around her and made life so much easier. The more she did, the more I wondered why I waited so long to give her control. 

Perhaps the biggest change was in my mental health. It improved so much, for the first time in years, I was able to leave my therapy behind. 

All in all I was fortunate in how I was able to transition into a new gender life as a trans woman. I already had a circle of supporting cis-woman friends who never knew much of the old male me, plus an accepting daughter and future wife who were pushing me forward into an authentic life.   I read of so many other transgender individuals who were not so lucky. I can never not give all my friends and family I often mention, enough credit for helping me to restart my life. The entire process of sliding down the male hill into a soft female landing was such a huge relief. 

Another De-Transitionist

 

Image from UnSplash

Recently I read another social media account post from a person stating they (my pronoun) were no longer identifying as transgender.

Predictably, they received push back from their followers. Many said it was a mistake and managed to state their thoughts in a very negative way. I simply said, it's your life, you should live it as you choose. Which for many transgender women or trans men is easier said than done. Many asked why and they replied they were not happy.

As far as I am concerned, I have written before how in my life, happiness has been difficult to achieve anyhow so a simple gender comparison for me was easy to make. The only fact I could zero in on was I was intensely unhappy with my old male life and wanted it to end. Plus, it made it easier for me to decide to give my feminine side a chance. One of the reasons was, everytime I had dared to give her a chance, the entire process felt so natural. Destiny was telling me my life was always supposed to be this way. I knew my gender path would not be an easy one but I was prepared to face adversity. Such as losing my family, friends and finances. 

I certainly do not put myself up on any sort of pedestal and think I am the only one who felt the way I did when I considered the forks in the road to get out of my gender closet. In addition, when I considered the person who wanted to de-transition, I wonder how deep they were into attempting to live as their authentic self. Or, were they confused what their authentic self was to begin with. It took me years to figure it out in my case. 

Perhaps a person who is considering going back to their birth gender didn't realize how completing a gender transition is nothing to play with. It's much more than changing clothes and entering a world stripped of all your old male privileges. It's a lifetime of commitment in an ever changing country which in many areas is enacting anti-transgender laws designed to put roadblocks in our ways. Conceivably, going back would also put them back in good graces with an unaccepting family system. I can understand the powerful draw of going back. In my case none of it worked. Once I started down the very serious path to living a feminine life, I knew I could never go back. My mental health improved and I was able to live happily as a full-time transgender woman. 

My biggest concern for the person saying they are transitioning is they don't go from the proverbial frying pan into the fire when they attempt to return to their previous gender. In the end, I hope they can just find happiness. 

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

 

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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

 

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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.