Regrets?

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Jessie Hart Archives

I would suppose, similar to anyone who has reached the stage of life I have reached, may have a few regrets.

As far as I am concerned, I don't have many. Along the way, I have been fortunate to have loved and be loved by several different women. Three of which married me. In each of my marriages had their own special ups and downs. One of the regrets I do have was when I needed desperately to be the one who cheated on my first wife so I could marry my second wife. I wasn't proud of being the cheater in the relationship but I see my first wife (and mother of my only child) approximately twice a year and we get along well. We both moved on to other long term relationships which proved out to be for the best. 

I was with my second wife for over twenty five years before she tragically passed away from a massive heart attack. My regrets with her primarily revolved around me not knowing the full reach of my transgender feelings and I ended up dragging (no pun intended) both of us through the gender mess I created as I transitioned. It would have been easier if I had just pulled the band-aid off and just let the dust settle where it may. But I was selfish and still liked part of what I had accomplished as a guy. So much so, I didn't want to let it all go which was a major mistake. One which almost killed me. I would not wish attempting to live convincingly between the two main primary genders on anyone. From day to day, just to get by, I needed to concentrate which gender I was that day. I found myself in some sort of a gender twilight zone trying to figure out daily was I a man or a woman.

I did know I loved being a woman, I loved the clothes and the challenge of facing society daily as my increasingly feminine side. Sadly, as with anything else you love, many problems come with the process. Life at once became exciting and terrifying. I didn't know what I was doing as a novice transgender woman but I learned fast. At the least, I gave myself the latitude to make mistakes and keep discovering a new world. Regrets? Sure, I made many mistakes along the way as I presented myself to the world. Plus I was lucky too when I got away with more than I should ever been able to. The main ones occurred when I went behind my second wife's back to cheat on her. With another woman who happened to be me. I had always thought I was a honest person, so the whole deal proved to be excruciating to me. The more success I felt on one hand felt so natural but at the same time I was cheating on the person I loved.

I suppose everyone has regrets but destiny has softened my challenges I have experienced from the challenging idea I wanted to change my gender. Ironically, it was my third wife (and current one)who came along and saved me from myself in my darkest days. She made me a believer in myself as a person and convinced me I should have live fulltime as a trans woman. She sealed my belief in her when she told me she had only seen the feminine in me. That was over a decade ago and we have never looked back and our relationship remains strong.

It doesn't do much good to have any regrets anyhow. Life moves fast and if you didn't take the opportunity to seize it when you had the chance, it may never come around again. I am just fortunate in I have been blessed with a long life to try not to repeat my mistakes and have regrets. 

Changing the Gender Locks

Image from Adam J
on UnSplash

It took awhile for me to change the locks on my old male self. He kept hanging on and on to the smallest reason not to go all the way with my gender border crossing.

Through it all, he was quite comfortable on occasion taking advantage of all the male privileges he had come to take for granted. He was used to taking personal security and even intelligence for granted. Age seemingly was the only prerequisite in gaining respect. When the locks were changed years ago, life changed with it. 

Changing ones' gender is nothing to be played with. I'm biased but I think transitioning as a transgender person (woman or man)is one of the hardest things a human can experience. All the cards are stacked against you as early in life you are forced into a square hole when you are certainly a round peg. Perhaps the interesting fact of the whole gender experience is when one door opened and you went through it, often it was slammed shut and locked behind you. You then had to be quick on your feet and learn what to do next. Surely mistakes were made but it was the only way to learn. Some would call it tough gender love. 

The farther I went in life as a novice transgender woman, the more locks I needed to change. The more I entered the world and was successful as a feminine person, I felt natural and couldn't wait to lock the old male door behind me. Even when it led me to potentially dangerous situations. I write often of the times I was on the verge of being seriously molested or worse in my early days of exploring the world. One night I was dressed way to skimpily and attracted the wrong set of man. My second wife needed to bail me out of the situation so I never heard the end of it. Even still I locked that door behind me and moved on with an important lesson learned. 

I was doing what I believed in so I was stubborn and any progress gave me hope. To follow in someone else's path would just have not worked. So I said to hell with the possible consequences such as losing my three "F's" family, friends and finances, I kept changing the locks behind me. I needed a huge lock as well as amazing amount of duress and thought before I decided to go through with donating all of my male clothes and deciding to live a fulltime life as a transgender woman. Also, hormone replacement therapy was in my future should I decide to explore the possibilities of furthering my femininity through HRT.

Along the way, I became very proficient at changing my gender locks and hiding them from the everyday world. Depending on the door, often I had to stop and look around at a totally new and exciting world. Once I did, I always decided to move on seeking a new door to go through.

A Caricature?

 From disabled transgender poet Torrin A Greathouse:

"If we're not feminine enough, that is a failure. But if trans women are too feminine, that is also seen as a flaw. It is seen as a caricature of womanhood."

Where does that statement leave you? For me, it brings back memories of obsessing over every aspect of my feminine presentation. In fact, I have often written about the differences between my early posts here in Cyrsti's Condo as compared to my current offerings. Nearly all of the decade old posts have a definite  bias on every aspect of what I was wearing.  Perhaps I was presenting as too feminine and maybe I was a caricature myself. 

Of course time changes all of us and I was changed by the cis women I interacted with.  They brought a different feel to their femininity and one I happened to identify with.  All of a sudden finding exactly the correct accessory to wear when I met them wasn't the priority, communicating with them and the world became a real goal. I guess you could call it acceptance over accessories. Through it all, I was able to observe how they interacted with the world and my small tight-knit circle of friends ushered in my unique personal womanhood. 

In other words, I was able to escape the "caricature" mold Greathouse writes about by capturing what being a woman meant to me. Obviously there were surprises along the way. 

Overall though, I changed and was able to finally thrive. In no small deal thanks to all of them. 

They showed me the way out of the clothes into the real world and gave me confidence to live the life I had always dreamed of living. 

If you would want to read more of the "NPR" post with Torrin Greathouse, follow the link above. 

Tit for Tat

It doesn't take a genius to figure out the human obsession with breasts.  "The girls" are one of the basics of a woman's femininity and an attraction to others.

How funny is it when guys think I'm going HRT to just to grow my own breasts to play with. 

I won't deny breast development has not been a pleasant part of my exterior feminization. In many cases just the slightest touch is a constant reminder of where I am on my transgender journey. BUT on a much larger scale, the transformation of my skin and the thickening of my hair have been just as astounding. In fact, I should write a separate post just about my hair.

Plus, let's not forget my continued lack of climate control.  I went through the hottest summer of my life into my coldest winter. I wish I could blame it on the climate but I can't. It's real and it's me.

The main point is that all pieces of this gender puzzle are continuing to come together and the process feels so right. I can only hope this summer will be a little more "air cooled"!

Only Two Things are Certain Part Two

As we left this post we already had determined birth and death were absolutes in life. Anything else can supposedly be changed or at least altered.  Which brings us back to the holiday season.
It's the easiest time of the year to feel alienated from former family, friends and the world as a whole. I'm the first to admit I am so fortunate to have found a whole new group of cherished friends to enjoy and usher in a new year.

More than a couple of people have asked my "secret". The only secret is that I don't have one. My keys were honesty, networking and persistence. None of this happened quickly for me. On a time scale I went  four years or so going to gay venues as a "basic training" of sort- before I knew my transition had to begin  in earnest. At that point I started to explore my femininity in straight venues. Sure it was hard but then again the stakes were high. But we all know none of this transgender journey was going to be easy. It wasn't.

As I branched out, obviously some places were more receptive to me than others. Naturally I began to frequent the ones who were nicer to me. It turns out a potential negative wasn't. I was hard to miss and I was remembered. Sure I was a trans woman but I was honest about it and it was up to me to make my experience a positive one with others.  So within a couple of visits  I went from "hey isn't that a?" to hello Cyrsti (a real person). 
What happened next was a direct result of all this effort and a lot of good beer.
One of the bartenders introduced me to her Mom (we have been friends now for nearly four years) and one night a woman down the bar slipped a note down to me saying Hi and we have been friends for three years.(both lesbians I met in a straight sports bar.) Now keep in mind this was over a period of three years or so. You can not approach any of this process just a few times and run and hide in your closet which leads me to a controversial approach to networking yourself- the Internet.

At one point in time I went nuts on quite few dating sites. No transgender rip off ones but all kinds of others. All of them were consistent in only having two profile categories Male & Female. I was very experimental and spent a little money to subscribe to a couple sites.  On some I said I was a female then was quick to point out in my profile I was a transgender woman.  Others vice versa. I even switched which gender I was looking for. The whole effort turned out to be a total learning experience with a huge pot of gold at the end of the rainbow.

Of course I've heard the success stories of Internet dating these days and I know the percentages of people who have successful pairings on the web is on the rise. But then again there are bunches and bunches of worthless crazies out there. I encountered quite a few! However I met a person who is a dear friend and a couple others that I'm in contact with on a fairly regular basis I care about. The bottom line is that if you aren't really ready to sort through a lot of people and you fold your tent and run after a couple failures then the net search is not for you.

So that's my secret. None of it is quite difficult to understand but is very difficult to put in motion and of course it is my path. Who knows,  if you are facing a dark holiday period this post may help in some small way.

I'm living proof the unthinkable can happen and believe me I'm not that special. I hope it happens for you!

Looking Back and Forward

Following the weekend's intense activity, I finally have had an opportunity to reflect on life as I know it now.
Recapping just a bit, Saturday's burial of my outward male and emergence of my female self was intense to say the least. Sunday I sort of curled into a ball, Monday I worked diligently on all the projects I do and last night I went out for a drink to the place where much of my public coming out process happened.
I'm going to stop and quote a loving and giving quote from my Mom now: " Life is like a roll of toilet paper. The closer you get to the end, the faster it goes". As "non frilly" as that quote may seem-it's true.

Last night, I thought back on all the times I went to this very busy upscale sports bar in various "experimental" outfits and wigs. I've told whomever will listen (and some who won't) I was very much a trial and error transition person. (mostly error) I was fairly certain this feminine direction I was heading was the correct one but I had to find out for sure. One of the those moments occurred where I was last night. Years ago I was sitting there and this incredibly warm sense of well being came over me.  No, it wasn't the beer and I didn't have to run out and buy a store bought vagina- I just knew I found my true self.

At any rate, the last five years have been one hell of a trip. I went back to the dusty archives to pass along an ancient post from Cyrsti's Condo, called Weekend Update.  I was interested to see how completely I was into the psychical aspect of the moment...shaving legs, clothes etc. I won't pretend to say I'm not into the psychical aspect of being a woman now but it ceases to be the all encompassing factor. I guess it's important to me to look as good as I can but it's not the defining factor of my femininity. Again, I have been so lucky to have learned from a close group of genetic female friends currently and in the past on what a woman is and isn't.

As I look forward to the time I have left on this world, I'm incredibly excited what is around the next corner for me on this journey.  I'm never so sure what dose of positive karma brought me to this point. I compare my life as a human and a transgender person to an old school pin ball machine. Don't we all play this game?   Five silver balls and we are done- game over-see ya!  As hard as we try, we try to aim the silver balls and hope for big points. Skill is one thing though but what about luck and destiny? If you know those answers-please can I talk to you!!!!!

So looking forward, I'm hoping to have at least one or two balls left to play...and have as much fun as karma will let me!

Cross Dressing in the Old West

Being the "historical" not "hysterical" (most of the time) I am, I've heard of this book but never really read a review.
It's called Re-Dressing America's Frontier Past by Peter Boag.
Here's a bit of the review from Terri Schlichenmeyer:

 "For women, the frontier was a man's world. There was adventure and prosperity there, and becoming a man as much as possible was a way to seize opportunity. Safety was another reason for appearing masculine, cross-dressing could be scandalous fun, and it could help escape punishment for criminal behavior. There were also women who believed themselves to be boys from birth. For smooth-faced men, it was common to dress as women for dances and parties because biological women were scarce. Men impersonated women to entertain others. In some Native American communities, "berdaches" were encouraged to embrace femininity. Like some women, males took on girlish appearances to escape crime, and then there were the men who simply wanted to "be" women. But for those men, and their female counterparts, life wasn't easy. Being arrested for the "crime" of wearing clothes for the opposite sex was common and cross-dressers were often shunned. Interestingly, however, their partners (usually same-sex) were generally socially accepted. Re-Dressing America's Frontier Past is good, but long. Boag offers lots of excellent examples to back up his reasoning behind why these stories are largely hidden from history, and what he found will set western fans (not to mention screenwriters) on their ears. This is fascinating stuff, on many levels. And yet, the book has its distractions. It's very scholarly and often reads like a dissertation, which occasionally makes it hard to read if you're just looking for a peek at hidden history and not a lecture. That aside, because it uncovers a wealth of stories that are overdue for telling, I liked "Re-Dressing America's Frontier Past" and I think you will, too. If you're a Western History buff especially, you need to outfit yourself with this book soon."

It's a little pricey in today's world of E-books. Read more of the review here.