Sunday, December 31, 2023

The Home I Don't Live In

Image from Daiga Ellaby
on UnSplash

It certainly took me awhile but I finally learned my male self was simply an empty shell I existed in to get me by in the world.

Over the years, even though it was difficult, he managed to secure a spot in the world and earn his white male privileges. Participation in such male dominated activities such as sports and muscle cars led the public at large off the beaten track of who I really was. I was a cross dresser or a woman pretending to be a man. Along the way, I was still able to build a fairly strong home I didn't live in.

Around that time, my life in an an empty house became predictably lonely, even though I was doing all the traditional male activities. I was married, had a child and served my time in the Army to add to two college degrees. It seemed the more I tried to do, the less fulfilled I felt with my life. It wasn't until years later when I understood much of my frenetic pace in life had to do with my gender desires being off center. In essence, I was building a home I couldn't live in. 

In it's place, I was increasingly becoming more and more serious about discovering if I could actually pursue a dream of living as a transgender woman. What I was doing was observing others in the trans community who were moving towards living fulltime feminine lives. I wondered if they could do it, why couldn't I? I was learning consistently by going to small mixer/parties in nearby Columbus, Ohio. The get together was hosted by a soon to be retired firefighter who restored an old house in a well known restoration district. I was extremely interested in her path because she was going against all the so called "rules" back in those days. Back then it was expected when one fully transitioned into being a trans woman, she was expected to leave her old life behind and start all over again. The woman I knew was going to not do any of that and I dreamed of doing it also. The same as her. Plus her parties included a diverse group, including the occasional lesbian and I learned early of the attraction I felt for lesbians' and vice versa.

Even though I did manage to slightly follow in her footsteps, leaving the male house I built proved to be anything but easy for me. To arrive at my destination, I would have endure intense moments of pain and suffering. As my old male self finally crumbled, I would be remiss, if I didn't mention the group of friends I found to help me build a new house. This time the correct one, complete with a life in my chosen gender. 

Even though the challenge was there to build my new house the correct way, I still needed to make sure all the improvements were built in to further make my new life more pleasurable. Out went the old male clothes and in came women's clothes including shoes, wigs, and makeup. 

The end result was, I discovered I could indeed build a brand new gender house and redirect the rest of my life living in it. The home I didn't live in was long gone and I felt a freedom I never thought I would ever have again in my life. 

Saturday, December 30, 2023

Sizing Up the Crowd


Image from Uwe Conrad 
on UnSplash

One of the earliest lessons I learned when I first began to attempt to present as a realistic woman in the world was how I was always on stage. It presented a problem since I had always been very shy around people.

It didn't matter because both men and primarily women sometimes went out of their way to size me up. Plus, while I am on the subject, I was very insecure about my size as a novice cross dresser or highly questioning transgender woman. Initially I made the mistake of walking slightly hunched over to hide the fact I was nearly six foot tall. Then I realized there were plenty of other cisgender women around me and I could stand up tall and project confidence to the world. I learned the hard way that people were similar to sharks and could sense another person's insecurities so I needed to do better in all aspects of my presentation as a trans woman. 

One of the key insights I learned quickly was quite naturally, the world I was trying to enter was run by women. So I needed to figure out how to effectively play in their sandbox. On the other hand, men were out since they had a tendency to ignore me anyhow. If a man did pay attention to me, he would normally treat me as a lesser individual. When men paused to size me up, my reaction was to quickly keep moving. I did have a few very rare interactions with men but didn't feel particularly secure with the experiences. 

Women were a different story. When I started my male to female gender transition I received more attention from women than I ever had as a man. As I soaked in the attention, I thought most of the women were just curious of why I was in their world and became amused when I needed to encounter the everyday issues they did in a feminine world. Such as personal security, hot flashes etc.. They would  simply smile and say welcome to their world. Little did they know how badly I wanted to be in their world. Being included in a group of women helped me not to be singled out for attention. When the group I was in was sized up, I was simply part of the group and not an individual. 

The group of women I was a part of just happened to be lesbians so I faced a unique situation when it came to what sort of crowd was sizing me up. On several occasions we would attend lesbian mixers, so blending in met a nice pair of jeans, top and in season boots in the winter. In terms of the society I was trying to fit in with was I attempting to present as an attractive lipstick lesbian. I was successful on occasion attracting super butch lesbians and in fact, one of my first dinner dates I had with a man was  a trans man. We stayed in touch and often he made fun of me for being scared to death on our date. Which I was!

Scared or not, over time I became experienced in sizing up the crowd and bracing myself for the impact I would make. Somedays I receive little or no response to my public appearances. When nobody seems to notice me I know I sized up the crowd and won my gender struggle. Other times, when the room I am in goes silent and I am stared at, I know I wasn't so successful. At this point in my life, I am used to all sorts of reactions, so I can move on quite easily. 

Even still, I am aware of the public crowds I face and do my best to size them up and react appropriately. No longer am I so shy.

Friday, December 29, 2023



Image from the
Jessie Hart archives. 

As I was seriously pursuing a life as a fulltime transgender woman the interruptions I went through made life very difficult.  

What happened was I was still attempting to live life as a man and a woman, I found I favored one gender over the other. The gender I favored of course was my feminine side. When I was out in the public's eye, I felt so natural and so alive. As I continued down my path, I became obsessed with improving my presentation as a woman. I had so far to go to try to perfect moving as a woman, not to mention any new communication skills I would need to get by. I was able to work on all of my gender issues approximately three days a week before I needed to revert to my old relatively macho male self. 

The problem immediately arose when I was forced to go back to my ingrained male ways or all the male type walking and talking guys do to survive. In order to be successful again as a guy, my path to femininity was interrupted and I felt as if sometimes I needed to begin all over again when I switched back to my newly preferred gender. When I did, I had to work harder to maintain what I had earned previously. Working harder allows me to explain more in depth a recent post I wrote here in Cyrsti's Condo called  "Trying too Hard." From the post I received several comments (thanks!) alluding to the fact I somehow mentioned working too hard to be a presentable transgender woman was not something we all go through as trans women. What I really believe is we have to work much harder than the average cisgender woman to earn our way in the world. Among other things, we trans women didn't benefit from growing up feminine. With no feedback on how we looked or how we acted. 

Of course too, all the interruptions I experienced on my gender journey just became worse the more I attempted to do to follow my path. It was so frustrating when I was mentally celebrating the evenings when I felt I looked and was able to act correctly as the person I increasingly wanted to be. Those were the evenings I felt my entire image worked. My makeup, hair, clothes all were on point and I was able to walk in my heels without falling or looking like a linebacker. Sadly, the next morning I would need to make sure I had removed all my makeup and had gone back to walking as a man. It was tough on my fragile mental health as I felt like a juggler trying to keep all my balls in the air. (No pun intended). 

Somehow, someway, I made it through this toxic time of my life. Ultimately, I used all the internal frustrations I was experiencing as motivation to move on. 

Moving on became a theme in my life for once I didn't use the theme to escape, I used it to move myself forward into a new gender world I had only dreamed of. Finally free of all interruptions.

Thursday, December 28, 2023

She Wouldn't Share


Photo from the
Jessie Hart Archives

As I was progressing down my increasingly exciting gender path it became clear to me I was heading straight to a crossroad which would require tons of thought and effort.

The main problem I had was my two binary genders (male and female) were constantly fighting with each other for dominance. I attempted to satisfy both of them, plus keep my unaccepting second wife away and maintain my sanity. What I was trying to do was live three days a week as a woman and maintain my male dominated job as well as convince my wife I wasn't doing more than we agreed to when I was a cross dresser. To make it clear, my wife never wanted me to progress any further in my life into a feminine lifestyle.

The problem became evident when I became more and more successful in most all of my feminine pursuits as it became clearer and clearer to me indeed I was transgender. In the process, I wasn't doing myself any favors as the gender ripping and tearing I was experiencing made life unbearable for me. I just couldn't easily shift gears when I needed to switch from feminine to masculine in a days notice. I caught myself doing feminine things when I was supposed to be a macho guy and vice versa. When I was trying my best to be a convincing woman I needed to not walk like a man or wear a male scowl on my face. As you can understand, the pressure I was experiencing was tremendous and it dominated all of my thought when I wasn't out attempting to see if I could indeed succeed in my dream to be a woman. Trans or not. 

As it turned out, my feminine self did not want to share me with my old male person. Plus, she was ready to do battle with my equally as strong willed second wife. The overall battle was no fun and I would wish the gigantic hassle on anyone. What should have been a more enjoyable time of discovery in my life was turned into a contest for my very being. The end result was a suicide attempt on my part which was fortunately unsuccessful. From there my wife won the struggle and I decided to "purge" for the final time in my life, grow a beard and reject completely my feminine self. Through it all, she went back into her closet but wasn't at all happy about what had happened. Sadly. she didn't have to stay in her closet long because within a year, my wife passed away from a massive heart attack. 

Very quickly after the death, it was clear to me which way I would turn. My inner female reasserted herself and brought joy to me during the darkest moment of my life when I didn't know what I would do. From then on, she didn't have to share me with anyone. It took awhile for her to accept my wife Liz but once she did, she went all in. It took her over a decade of interacting with Liz before she decided to get married. 

Over time, again and again the true dominant gender I was dealing with won out. Mostly by biding her time. When she did have her chance to live, it was amazing to me how fast and easily she took to her new life in the world. All the times I was facing the gender unknowns in the world, she would step in to help me.

She proved not sharing me ultimately was the correct move to make.   

Wednesday, December 27, 2023


Image from Brett Jordan
on UnSplash

For as long as I can remember I have been a procrastinator. Unless I was really pressed, it was always easier for me to put off until tomorrow what I should have done today. 

Later in life, being a procrastinator in my gender life came back to haunt me. As I continually gained ground in learning if I could exist in a feminine world, the more the pressure on me increased to decide what I was going to do with my life. Primarily effecting my already fragile mental condition. I had previously been diagnosed as Bi-Polar along with having elevated anxiety so I already had plenty to deal with mentally. So, I was not in any position to improve my mental condition by procrastinating over my transgender issues. Still I persisted and my problems only escalated. 

I was frustrated when every success I found as a transgender woman, seemingly just led me to the ultimate decision I was having a problem facing. Was I ever going to be follow my dream and live as a woman. Plus, all my procrastination led me to was an increasing reliance on alcohol to limit the mental pain I was suffering. What happened was, the effects of alcohol gave me courage to explore further if I could make it in a feminine world as a full time trans woman. Was I gay, was I trans? I needed to know.

Finally,  rational thinking took place and I could take it no longer. My gender truth was slowly but surely killing me. One night I sat down by myself and made the biggest decision of my life. As soon as possible, I decided I would seek a doctor's approval to begin gender affirming hormones and never look back on an old male life which was always a struggle to maintain. What a relief it was to finally face my truth and move on as my authentic self. It was time to put all my procrastination behind me and my life immediately began to improve. 

Still I was not up on any pedestal. As I always mention, I could have never have accomplished what I did without the help from several key cis-women friends and family. In essence my friends pushed me over the cliff into a world I had only ever dreamed of. Perhaps, not so surprising, my reliance on alcohol started to decline as at the same time my overall mental health began to improve. 

Ironically, my only problem became that I procrastinated coming out as a transgender woman as long as I did. I would have loved to have the years back when I anguished over which of the binary genders I would live as. In other words. sometimes I think I wasted too many years to claim a life as my feminine self I just kept putting off. The only excuse I had was, during my procrastination years, the world around me was changing. In the pre-internet years, there was a definite lack of information and contact. Our dark lonely LGBTQ+ closets were difficult to escape. 

The fact remained I still grew up putting off the most important aspects of my life and it continued until I finally decided enough was enough and it was way past time for me to live as a transgender woman fulltime.   

Tuesday, December 26, 2023

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.  

Monday, December 25, 2023

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.



Sunday, December 24, 2023

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. 

Saturday, December 23, 2023

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.    

Friday, December 22, 2023

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.  

Thursday, December 21, 2023

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 far. 

Wednesday, December 20, 2023

A HUGE Relief


Image from the Jessie Hart

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. 

Tuesday, December 19, 2023

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. 

Monday, December 18, 2023

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.


Sunday, December 17, 2023

Eating our Young


Image from the Jessie Hart

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.  

Saturday, December 16, 2023

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.   

Friday, December 15, 2023

Night Moves


Image From 
the Jessie Hart

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. 

Thursday, December 14, 2023



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. 

Wednesday, December 13, 2023

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.  

Tuesday, December 12, 2023

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.  

Monday, December 11, 2023

Owning It.


Image from the Jessie Hart

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.

Sunday, December 10, 2023

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.

Saturday, December 9, 2023

Supporting Cast

I'm on left with Nikki and Kim
on right.

There was no way I could have pursued my male to female gender transition as quickly and as thoroughly as I did without help from my women friends. 

Having said that, it is important to note I had already made it to the point in my transition when I could present rather well as a woman in public. In other words, I had paid my dues learning to dress to blend with other women in the venues I frequented. When I went to upscale malls, I went with my nicest professional business woman attire and then I would wear my jeans, boots and sweaters going to my sports bars or lesbian bars. To me at the time, the entire process was great fun and presented me with yet another facet of being feminine. 

After I had learned from all of my mistakes (or most of them), I was able to learn so much more about going even further towards my dream goal of living as a full time transgender woman. By pure chance I ran into two other women in the sports bars I was frequenting and we became fast friends. One of the main things I learned was I didn't need a man to validate my existence as a transgender woman because my two friends just happened to be lesbians.  Along the way, we drank a lot of beer, cheered on our favorite sports teams and had a great time. I think the evening I remember the most was when I was asked to be Nikki's wing person when she was trying to get a conversation started with another woman she admired. I agreed to try If you are wondering, I failed at my attempt to set Nikki up for success. It turned out to be my only attempt ever to act as a wing person at a lesbian mixer. All of that happened back in 2015.

Of course too, there was Liz who I met on a on-line dating site under "woman seeking woman" categories. She too identified as a lesbian, so I had quite a bit of experience on some of her thought patterns involving men. With her, my supporting cast just became stronger. At the time, I was in the last stages of still attempting to maintain some sense of having a male life. Very quickly, we formed a bond which included a first date to a drag show and a New Years Eve date when I first started my hormone replacement therapy medication. At the time, she very much sealed the deal on me transitioning further. I knew I was on the right path. 

I kept on putting off going full-time as a transgender woman long enough until Liz finally told me she didn't see any male in me at all and why didn't I leave him behind. I did and started a ten year relationship which culminated just over a year ago with us getting married. Throughout the years, she has been my supporting cast.

Plus I can't forget my daughter's input on my life. She has accepted me from day one. Even to the point of giving me my first hair styling appointment to her salon for my birthday. Which is a post for another time. 

To all of my supporting cast, I love you all.

Friday, December 8, 2023

Burning Bridges


Image from Marcus 
Clemens on UnSplash

Yesterday as I sat waiting for my wife Liz at one of her doctors appointments, I had a chance to pause and reflect back on my long and often difficult transgender journey. 

First of all I marveled on how I was accepted as me. Not necessarily as a woman or a man but as just me. The whole process to arrive took me over fifty years of my life to get here. A place where I could feel secure and relax with just being my authentic self. Then I started to think of how many bridges I torched to get here.

My main problem was my old entrenched male self. Even though he never wanted to be a part of my life at all, once he did, he never wanted to give up what he earned. So he fought completely to maintain his edge. He had an edge in what I like to call the "three F's" or family, friends and finances. He had built all three and was able to maintain a great job to support his other interests. In the meantime my feminine self was doing all she could to break out of the confines of the closet she was in.  She went as far as starting small and large gender fires designed to sabotage his very existence. 

The biggest bridge she tried to burn was the financial one. What happened was I began to stop at venues close to and even part of the places I was working at during the same period of time. My thought pattern was, they wouldn't recognize my feminine self as my male self. I was wrong and they did. Leading me to all kinds of potential embarrassments if anyone told my wife they saw me. The prime example of it almost happening one night was when the disc jockey (who also worked for me as a cook) played "Dude Looks Like a Lady" immediately after I showed up. Fortunately, my wife didn't notice anything but I most certainly did. I knew then, the world knew I was a cross dresser. 

Deep down, I thought if my deepest secret was discovered I would be relieved and I would have the chance to live the transgender life I had always dreamed of. Sadly I still had too much to lose such as the first two "F's" or family and friends. It wasn't until much later, when my friends and family started to pass away and I reached an age when I could retire on Social Security did I finally see a path forward to leading a transgender life. 

What a relief it was yesterday to know I had reached a point in my life when I didn't have to be so self destructive.  No more severe mental illness or thoughts of self harm. I could sit and be reassured I wouldn't have to burn any bridges anymore. 

Thursday, December 7, 2023

Success equals More Success

Image from the Jessie Hart

In an extension of yesterdays' post which mostly concerned  the success I experienced  when I began doing a portion of the grocery shopping cross dressed as my feminine self, I decided to go further.

If you were wondering, I chose grocery shopping to sooth my guilty conscious because I was sneaking out behind my wife's back while she was working and I needed to find a way to knock out two birds with one stone. Help her with the shopping and help me with my gender issues. It worked well and I needed more to do. When the Christmas holiday season rolled around every year, I found I could again put my new feminine cross dressing skills to the test by doing all my shopping as a woman. 

Since my wife and I were vintage antique buffs, going to several area antique malls became one of my favorite ways to find the perfect gift. Again I was able to multi task when I explained to her what I was doing in my spare time. Ironically, the malls were a perfect alternative to all the other clothing malls I was used to. The all important store mirrors I was used to were replaced by antique style vanity mirrors which I could catch a glimpse of myself to reassure me I was an attractive woman. Along the way, I was able to find the very special gift for my wife and sometimes even my brother. In the meantime, the malls never questioned my presence so I was free to browse on my own with no interference. 

I was so successful and the process felt so natural, I expanded my shopping into several upscale regular malls in the Columbus, Ohio area.  Of course, when I did, I needed to upscale my appearance to match the other women I would encounter. Much different than the antique malls I was going to. The whole process was fun and presented me with a whole different challenge. The places I was shopping at were upscale garden stores because my wife was a huge gardening enthusiast. Just like the mall experiences I had always had, it seemed no one cared about my gender, just my money so I challenged myself to do more. I always wanted to do more so I began to stop at different venues to grab a bite to eat. Interacting one on one with servers and/or bartenders helped me out of my gender shell I lived in. It worked and I was able to achieve more in my cross dressing life than I ever thought I could.

Even though I was successful in my shopping trips, I was still too shy to ask for help moving a large item I wanted to my truck or SUV. I found quite a bit about feminine privilege's when one night when I was dressed in my favorite black pant's suit, heels and blond wig. I then found an oak bookcase I wanted to give my wife but couldn't figure out how I would get it to my vehicle.  Problem solved when I gathered enough courage to go up to the check out counter and buy the piece of furniture, suddenly I was approached by two young men to move it. I was so relieved and flattered no one questioned why I couldn't move it myself. Once I got it home, in the garage, after I had changed out of my clothes, I slid it out of my vehicle and covered it up with old blankets. I made my wife swear she wouldn't look under the blankets and at Christmas she was overwhelmed with the gift which matched the oak roll top desk we bought together. 

From then on I was emboldened to do all my holiday shopping as my novice transgender woman self. I am certain my feminine side did such a better job doing the gift shopping, she deserved to do it all. Success equaled more trust and success.   

The Gender Waltz

Image from Clarisse Meyer on UnSplash Since the beginning of time, the two binary genders have done a special dance with each other.  Being ...