Trying too Hard

Photo from the 
Jessie Hart Archives

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

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

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

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

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

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

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

Merry Christmas

 

Christmas Party Image
My wife Liz on right.

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

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

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

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

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

 

 

I Wish

Ralphie from the
Christmas Story Movie...

 Christmas is perhaps the peak holiday of the year to wish for things you may never receive. 

I always thought my wish was the impossible dream . It was to wake up in  the morning and leave my old male self behind. If I had my way, which I never did, if anyone asked what I wanted as a gift. I wanted so badly to be gifted a doll or a toy kitchen to play with. I was so deeply hidden in my boy life, all I received as gifts were boy things such as BB Guns. If you are a fan of the movie "A Christmas Story" as I am, I was the direct opposite of the child star "Ralphie". In the movie, he wished and hoped for a "Daisy" BB Gun, which he finally received. I, on the other hand was gifted a Daisy and all I really got in return was shot in the arm by my brother. 

In those days, I did quite a bit of wishing I was a girl. When we went on vacation one year, I spent the boring times on the interstate highway looking for, then admiring teen girls in other cars. Especially a dark haired beauty I remember who I really wanted to be. I ended up putting my pillow over my head and existed somehow until we stopped the next time. In fact, my whole life was just existing until the next time I could sneak around and put on my feminine clothes. 

I don't know what I was thinking but I was never sure what my older years would be. The only certainty at the time was the likelihood I would have to serve time in the military because of the Vietnam War which seemingly was endless. I just knew my search to be my authentic self would have to be on hold at some point. I say search because I was never certain what the ultimate gender question with me would be. 

As I have detailed in several earlier posts, when the holiday shopping season turned out to eclipse Halloween as my favorite holiday. I learned so much about my feminine self during this time of the year while at the same time I was gifting others. The end result was I could indeed at least live a life as a transgender woman if I wanted to. All the wishing I had endured in my life could finally end and reality could set in. 

It all turned out I was gifting myself with the ultimate gift I ever could receive. Before you think such a gift was selfish, it was a desperately needed gift I needed to even survive. Attempting to live in a world I never wanted was killing me, literally.  It wasn't much longer when I decided to write about my life in the hope it could help others who may have gender issues. 

This Christmas, I hope you are able to celebrate the holiday as you see fit, religious or not. I know this is the most difficult time of the year when LGBTQ+ and primarily transgender individuals suffer. Too many of us have lost family (including me) for just being ourselves. Sadly, all I can really do is wish you the best and as always thanks so much for taking the time to stop by Cyrsti's Condo. 
 

Making a List

Image from the 
Jessie Hart Archives

Making a list and checking it twice of course is a very Christmassy thing to do. The closer we would become to Christmas itself was the time I checked my funds and decided what last minute shopping I could do. 

Normally, by this time, I had visited all the usual antique malls (dressed as my feminine self) looking for that last minute special gift for my wife. Frustration built  if I couldn't find anything in my price range or find it when I was shopping as a woman. As time ran out, sometimes I was literally the last one in the mall looking for a gift. As luck would have it, many Christmases, I was rewarded and found a wonderful gift for my wife. The only problem was I had to shop as my old unwanted male self. 

She (my wife) was very difficult to buy for because I always knew she we attempt to outdo me in the gift department. We had three major gift exchanges to plan for, so I needed to do the best I could. The first exchange we went to was at my brother's house, the second in the afternoon between the traditional two of us and one at night when she gifted my feminine self with a couple of gifts. Normally, I received very nice sweater and skirt sets which I couldn't wait to put on.  As I remember, one year my wife gave in and let me cross dress and even took a picture (long gone) of me wearing the gifts she gave me. Obviously, most years, I couldn't wait for the special gift exchange to happen.

Through it all, I never made lists. I mentally kept in mind what I wanted to do and even did a fairly good job of keeping it all straight. This carried with me as I began to seriously transition into a transgender woman. Instead of notes, I knew what I had been successful at doing and then knew either I could try it again or attempt something new and often exciting. Examples included when I began to branch out from just going to women's retail stores in malls and trying out new venues such as bookstores and restaurants. Anything to see if I could successfully exist in my new gender world. What turned out happening was I could exist and needed to do more. Once I did. I still never thought I would need to build a whole new life so quickly and still not make any lists to do it. 

No matter where I was, if I tried to make a repeat visit, I found I would be easily remembered so I started to wear the same wig and always dress to blend. When I did, I discovered the world wanted to know more about me for whatever reason. Basically,  women were curious and men stayed away as I left one gender club and sought admission to another. What I would have never thought to put on a list was how I would need to learn to communicate with other women who were so used to saying one thing and doing another. It was difficult for me to determine which boundaries I could cross (or not) with each of them before the claws came out. 

I suppose if I had been a person who worked from written lists, I would have had quite the history of my transgender transition built up. Or how I went through several separate gender transitions to arrive where I am today. Such as moving from serious cross dresser, to finally coming out to myself as transgender, to making the decision, to begin gender affirming hormones. 

I'm fortunate in my so called legacy continues on with my daughter and grandchildren with no written record needed.    

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.