Interruptions

 

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.

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.   

Procrastination

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.   

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.