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.

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. 

Success equals More Success

Image from the Jessie Hart
Archive 

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.   

Shopping 201

Image from Brett Jordan
on UnSplash

Over the years I did quite a bit of shopping in clothing stores and malls, mostly successfully.

It took a while but I finally learned much of my success had to do with the fact my money was more important than my gender to the average store clerk. Many I think worked on commission and anything they sold was added to their paycheck. Even still, the experience was valuable in building my confidence as a novice cross dresser in the days I was running from the idea I could be transgender. I was paying my way to people so they would be nice to me. Only one time did I run into any problems when an older clerk told me my skirt was too short. In response, I left and never returned since there were plenty of clothing stores to go to.

In a short period of time, I grew tired of the same old shopping I was doing and started to expand into stopping for lunch where I needed to interact one on one as a woman with servers. The entire process opened a whole new gender world to me and for the most part I was treated politely with respect. Overall the process took me to a whole different level of Shopping 101. I grew bored and was ready for a new course I called Shopping 201. 

The new course ended up providing me with endless possibilities to expand my horizons as a very serious cross dresser. At the time, I was searching for ways to do different things in the feminine world. One way to sneak around behind my wife's back was to start doing part of the grocery shopping. I would pick times I knew the grocery store we went to would not be busy and out I went. The women's fashion trends back in those days fit me well. I could wear one of my oversized soft sweaters along with a mini-skirt and flats and look like any other fashionable woman without going overboard. One morning in particular was memorable. 

On the day, I carefully shaved my legs and prepared my wig. After dressing and putting on a light amount of makeup I took off to the grocery when my wife was at work. I arrived at the store, grabbed a cart and proceeded to pick up a few needed items. Then I headed up to the register line to be checked out. This was back in the days before self checkout so there was only one way to go. At the register there was one older cashier and one kid bagging groceries. When he saw me, his eyes immediately went to my legs and when he noticed me watching him, he blushed and stammered something about helping with my groceries to the car. Never before and rarely since have I affected a male such as that. The cashier just gave me a knowing smile. 

From there, I couldn't resist reverting back to Shopping 101 and made a quick stop at a nearby big box store to pick up another pair of panty hose and shop for new makeup. By doing so, I was able to hide my expenditures along with what I spent at the grocery store. 

I was able to negotiate the morning as my feminine self and learn so many new things so I could graduate Shopping 201 and move on towards life in a transgender world.   

Going Back

Image of Liz on left and Daughter on right
from the Jessie Hart Archives.

 Recently I read a rather sad post from a person who was giving up her gender transition and going back to her original life. 

Even though I consider myself very fortunate in how my gender path turned out, I could understand the facts the person mentioned when it came to her new life. Among other things, the person related experiences which have haunted many of us following a transition. Such as having problems with loneliness, finances etc. So many transgender women are stuck in their houses, often with just having a computer to provide any contact with the outside world. This de-transitioner was older and provided a picture which showed a very presentable senior woman. My heart broke when I saw her image, I just can't imagine going back after putting so much work towards accomplishing a goal. Perhaps it is because I tried so hard and risked so much when I crossed the gender frontier. Plus, possibly for one of the few times in my life when I ever set specific goals, I was able to achieve what I set out to do. 

One of the major differences I saw when I read the post was how I approached the gender goals I was attempting to accomplish than most others. One of the examples was how I approached on-line dating services. I went all in with three or four services with the usual results of receiving tons of trash back in the process. I tried everything such as woman seeking woman to man seeking man. Amazingly, when I was giving up, some how I ended up meeting my current wife Liz who lived within driving distance in Cincinnati, a city I had always loved. That happened over ten years ago and it all started with a date to a drag show. As an aside, Liz identified as a lesbian witch so I was intrigued. 

In addition, the lucky move I made to create a new social life came when I decided to not go to anymore male gay venues and decided to go to the sports orientated big venues I was used to. I figured if I was going to risk being discriminated against, I might as well go to a place where I could enjoy myself. The gay bars aggravated me because I was always treated as a drag queen. What I don't recommend is the amount of alcohol I consumed along the way. On the other hand, I ended up meeting several other women in the venues who became friends. 

Very quickly, going back in my transition never had to be an option. By the time I decided to go all the way as a transgender woman, I knew my daughter would support me as well as Liz and my small circle of friends. As I made the final slide down the gender slope my landing turned out to be very soft. Even still, my heart goes out to those who are considering going back. Perhaps the whole experience could be thought of an ultimate experience which failed. Or maybe, they just wanted their old male privilege's back. 

Then again reversing my life again would be unthinkable because I would be so unhappy. I am afraid the person who did decide to go back would never be happy on either side of the binary gender border. 

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-Ha Gender Moments

 

Image from the Jessie
Hart Archives

Since I have been fortunate enough to live a fairly long life, I have experienced several a-ha moments when it came to my all important gender needs. 

When I started my gender journey as a youth, even though for the most part I considered my desire to cross dress my boy self as a girl to be a fairly innocent hobby...unless I was caught. Looking back, I don't know how I managed to hide what I was doing. 

Perhaps my first a-ha moment came when I was able to save up enough of my own meager funds to buy my own makeup and pantyhose. Sure I was petrified but somehow I made it through and was emboldened to do more. The whole process was to set the stage for more gender adventures and a-ha moments or being scared to death but loving the feeling of success.  

A few of the biggest moments I mention quite often and I am sure I will remember them when if and when my life flashes in front of my eyes when I pass on to the other side. One was the night I decided I would make the effort to go out as a transgender woman and quit thinking of myself as a cross dresser. Knowing full well, there was nothing wrong with being a cross dresser, I just needed more since I was increasing how many times I was going out and the venues I was attempting to go to. On the night in question, I ended up in the parking lot of a nearby "Fridays" venue gathering my courage to go in. The end result was predictable as I was to discover later. I lived and was treated with respect. I had done so much more than just interacting with store clerks in the mall. 

The more a-ha moments I had, the more emboldened I was to try more. For the most part I was successful except when I tried a couple redneck venues where I was roundly rejected. I guess you could say I had different a-ha moments when I had the cops called on me. I learned the hard way and kept on trying. When I tried, I was able to find more success in my quest to see if I could live fulltime as a transgender woman. As I progressed, on occasion I was elated and couldn't stop thinking how I could fit in to the feminine world but other times when I thought of the enormity of what I was thinking of doing. My male self and wife were fighting me at every turn so life was not pleasant. 

As it turned out I out-lasted both of them and finally came to the conclusion I needed to transition fulltime into a world I had only had ever dreamed of. It was a huge a-ha moment and took a ton of pressure off of me. From there, it was a short jump to deciding if I should undertake hormone replacement therapy or HRT. HRT was yet another major moment of success. My body took to the new hormones as if I should have always been on them. 

The only problem I faced at that point in time was my feminine inner soul taking over my life. She had waited so long and proved time and time again she knew what to do if I would just trust her. 

As I near the age of seventy five, I am sure the a-ha moments maybe will be less numerous but more dramatic as I face the final hurdles of life. 

Virtual Outreach

Image from the Jessie Hart
Archives.
Ohio River in background...

 Recently I experienced a busy day virtually on the old laptop.

First of all, I needed to go through the pre screening process for another colonoscopy. I just had one a year ago but the doctors removed a sizable polyp which fortunately turned out to be non cancerous. Even so, instead of waiting the usual three years between check ups I was scheduled for to come back in a year. If you are not familiar, colonoscopies are not the most pleasant procedures to go through but on the other hand, having intestinal cancer is a terrible alternative. 

I don't know how many of these procedures the Cincinnati Veteran's Administration hospital does a year but the woman doing the intake on the phone almost immediately said, I remember you. Being transgender I am used to being remembered. However, this is one of the times I would have preferred not to be remembered. The woman I was talking to on the phone possibly reacted at my often poor attempt to sound feminine on the phone. Part of my transition I am always working on. Hopefully this time, I won't be miss-gendered when I go in early January for the procedure as I was last time.

The second part of my virtual day occurred later on when I attended the monthly meeting of the Greater Cincinnati Alzheimer's diversity committee. As always the meeting was very gender affirming as the other four participants were all women. It's almost as if I was in another mini girls night out. Plus, I am a big believer in helping anyway I can with the association because years ago, my Dad passed from having Alzheimer's. When I approached them to do more, I was pleasantly surprised to learn the association already had some guidelines in place to deal with LGBTQ patients. However as we all know, being transgender presents more unique opportunities we have to encounter than the rest of the gay or lesbian community. 

One thing I have had to do (which I have been putting off), is write a short post for the Association's Facebook page. It should be noted several of the members have made it a point to go to several of the regional Prides this summer to help publicize what programs are offered to help those in need. So hopefully I will be just aiding in the process. 

I also write for the local transgender - cross dresser monthly newsletter and each time I encourage anyone else to wants to become involved a path to do it. So far, no one has come forward to volunteer which is no real surprise because so many members are still deep in their closets. On a wider scale, if you have ever been touched by Alzheimer's and have time to spare, seek out your local association and see if they have a diversity committee to volunteer with.

One thing with a virtual day is, I need to apply makeup and fix my hair which is always good. In addition to my virtual appointments recently, I also had another one a couple days ago when it was time for the Dayton, Ohio VA LGBTQ support group. I learned then my long time (ten years) therapist is leaving for another job. I was very sad because I have always looked up to her as one of the top three influencers in my life. It will be interesting to learn if anyone else will run the group. 

Now, for awhile, life will settle back down as Thanksgiving has now passed us by and it has occurred to me I have not written about my family experiences yet. Where does time go?

Stuck in the Middle with Me

 

Image from Rene Ranisch 
On UnSplash

Once upon a time and probably more than once, my second wife told me my cross dressing existence wasn't all about me. 

We were usually fighting about my feminine existence when she came up with the same comment. The unfortunate truth was it was all about me. I had a singular desire to look better as a woman and I knew deep down the whole femininization process would not be accepted by my wife and if I was to succeed at all, I would have to do it myself. Since she was unable to help, it meant I was on my own to discover my own fashion, makeup etc. So, for the most part, we never saw eye to eye on anything when it came to my cross dressing. Over the years, it became obvious she didn't like my inner woman at all.

Even though I knew it was and had to be all about me, life went on and we were able to stay together for over twenty five years until her untimely death. Until the end, she resisted any idea of mine I would ever want to begin down the road to trying a transgender lifestyle by starting hormone replacement therapy. When she always stated she didn't sign up with me to be with another woman again I had to agree with her.

Since she did not accept me, I started to sneak around behind her back and found out it was possible I could follow my ultimate dream. In the world I was beginning to discover, I was able to begin to carve out a new life as a transgender woman. When I did I became stuck between the two binary genders. I was trying to live as my old male self a couple days of the week and my female self the remainder of the time. Of course my life became unbearable and I sustained dark days when it came to my mental health. Being stuck in the middle with myself was not a fun place to be. I would come to learn in her own way, my inner woman who was doing battle with my wife was just as strong willed. 

I quickly figured out my old male person was going to be the first person to go away when my wife passed. I'm sure in the next life, my wife wasn't surprised to see I quickly transitioned totally into a feminine world. She always said my dog would never miss her if anything ever happened and she could have added my inner woman would not have missed her either. To make matters worse with my overall mental health, my male self desperately missed her. Possibly knowing my wife was his last chance at maintaining any sort of life.

 Even though the times I was out exploring the world as a novice transgender woman on occasion I was terrified, I pushed on to experience the excitement of exploring a life I had always dreamed of. When I did, often I was surprised at the outcome. I never expected many of the results I had when my inner feminine self took over. Quite a few times I couldn't believe how easy and natural life turned out to be.

Being stuck in the middle with me turned out to be worth all the hassles I went through to arrive there. 

Gender Variables

Image from the Jessie Hart
Archives

When I was first looking at myself cross dressed in the mirror and when the mirror was lying to me, I felt as if I was well on the road to understanding what my life may be like if I ever had the courage to transition.

Of course I had no idea of the obstacles and challenges I would need to face as I attempted to live a life I had only dreamed of. There were plenty of times when I woke up in the morning following a vivid feminine dream wishing I was still the female I dreamed of being. The problem being was dreams don't ever equal reality. 

Reality meant I needed to learn all the gender variables I would have to learn the hard way if I was ever be able to follow my dream and live full time as a transgender woman. The first example I ran into was how I was dressing myself. I mistook trashy for sexy and tried to validate myself as a woman by trying to dress as a teenaged girl. Happily, I learned quite quickly I was dressing for the wrong gender. I was dressing how my male self thought I should, when in fact I should have been dressing to blend in with the other cis women around me. Cis women are women who were born female. 

Once I started to be able to blend in with and exist in the world as a visible feminine person, I found out again the hard way, how many gender variables I still needed to face head on. The main issue I always mention is how quickly I needed to learn to communicate in public. Unlike the mirror, these people really wanted to talk to me. At the time, I had barely given any thought of how my voice as a woman would even sound to another person. What I ended up doing was I tried to mimic the woman's voice who was talking to me. Men, for the most part, left me alone so I didn't have to worry about them. I think other women were just curious why I was trying to live in their world. Whatever the case, I needed a vocal or communication plan and quickly.

What I learned was women (as I already knew) operated on a totally different wave length than men. There were to be no more direct conversations which men do so well. I needed to learn the power of non verbal communication clues as well as the passive aggressive nature that women deal with. There were many times I ended up with scars on my back when I thought a smiling face meant support. All a part of dealing with the new gender variables I was learning.

As it turned out, I was learning new layers of the feminine gender I had only dreamed of living. Plus I was ultra confident I made all the discoveries I could when along came  even more challenges. At that point I developed the small group of women friends I needed to rise to the next level of gender variables I needed to face. Often I was terrified but determined to stay the course I was on. 

I learned once and for all what I had always known deep down. Women live a much more layered existence than men. Little did I know I would end up living all the gender variables and then some as I lived my life as a trans woman. 

A Night with the Boys

 

Image from the 
Jessie Hart Archives

Way back in the early days of going to what were known then as "transvestite" mixers, I ended up having a very special experience, In essence, I was still out with the boys, without my wife, it was just they were all dressed as women. 

The evening started innocently enough, with the usual sizing up of those cross dressers around us. A little bit of everyone was there from those cross dressers who were desperately trying to hold on to their masculine selves, all the way to the glamorous "A" listers who formed their own cliques. What I didn't know was during the evening, the group organizers were providing a few makeovers from professional makeup artists. 

I was intrigued by thinking I could be chosen for a makeover if I could fight through my fear to do it. Somehow I managed to land a makeover spot and then had to remove all the makeup I had spent so long to apply. Plus my ego thought I looked pretty good. I was to find out I was wrong.

There were several artists working, of both genders. It turned I was lucky and got one of the guys who were working diligently trying to do the impossible. In my case, he did do the impossible and I went through a magical transformation. To make matters better (or worse), along the way the make up guy was trying to explain all the techniques he was using to transform my face. I did my best to remember everything he told me and in the end run, he helped me to understand things such as the power of using a small amount of blush to highlight certain areas of my face. 

All too soon he finished his work and told me to put my wig back on. I could not believe the transformation and in my mind I was so excited  to show off my new look to the rest of the group. I did receive several compliments which cemented my desire to do more when the "A" listers went out on their own after the mixer was over. They normally went to some sort of a gay or lesbian venue to continue the party. To be able to go, I needed to be invited, so I began to seek out the one of the small group I knew and essentially invited myself along. I succeeded and managed to tag along for a night with the boys, all cross dressed as very attractive women. 

On this night, I was able to continue my own "Cinderella" experience when the group decided to call a taxi cab and go to an even smaller venue which to me looked as if it was a neighborhood tavern of some sort. It was somewhere in Cleveland, Ohio, which is all I remember now. This all happened during the pre-video game era and the place had two pinball machines. After I ordered a drink, I was able to find a couple quarters in my purse and started to play one of the games. Before long, a man approximately my age came up and wanted to play the same game with me so I had a decision to make. 

The rest of the group was wanting to leave and if I stayed, I would have to either call another cab or somehow depend upon this guy I had just met to get me back to the hotel. I made the split second decision to take the safe way out and leave with the "A" listers I came with. Before I did, to rub it in,  I made sure they knew I was approached by a guy and they weren't. 

From then on, I was more or less accepted by the group although I never had their privileged negative attitude which was so judgmental to others. However, from then on I was always searching for another "Cinderella" moment when I was able to spend a night with the boys without my wife. Partly because she normally always came along.

 Sadly, it never came again. 

Role Model

 

Image from Averie Woodard
on UnSplash

I have a close acquaintance who is taking a giant step forward in her transgender world.

She is stepping out of her comfort zone and will apply for a new job as her authentic feminine self. I was fortunate to be at one of her first attempts to explain why she was coming out of the closet which was tormenting her so much. I remember thinking at the time how far she had to go on her journey as I wished her the best.

During the following years, she has faced the same issues as other transgender women and trans men face, from marriage issues to kids and family decisions to decide upon. She has been very open on social media about her struggles. Including public pushback when her wife and her go out to eat. She lives very close to me and I know the venues she has had problems in and I understand why. In fact, I have had some problems also in one of the venues and we never went back.

Even with all of that, she pushed on and is now trying to take her transgender life to another level. Her current job is a truck driver which of course presented it's own level of challenge at every stop she made. She transitioned on the job and literally changed  her outward appearance overnight. I really respect the courage it took for her to take on her work world the way she did. Now the challenge she is seeking is to apply for another job (in the same industry) but in a whole different job as her feminine self as a logistical scheduler of sorts. 

If she gets this job or not, she is a true role model for others in the transgender community. To step out of her old gender comfort zone and sever ties with her old life as a man is remarkable.  It's a giant step forward. 

I am far from an expert in finding a job in todays' world. But from what I am reading in Cincinnati alone there are a few companies who are LGBTQ+ inclusive and offer employment possibilities to aid in a person's transition. It's good for both parties as the company can hire a good employee and the trans person is able to take a giant leap forward and support themselves financially in their new world. 

As I circle back to the person I know who is applying for the new job, I am sure this is just the beginning one way or another for her to step forward into a life she has always dreamed of. I hope she gets the job on the first try! 

Even though I am retired and don't have to face the work world as a transgender woman, I can still see a role model when I know one. 

The Good Fight

Image from Fred Moon 
on UnSplash

Often, our biggest enemy we face when we transition from one binary gender to another is ourselves. 

In the case of male to female gender transitioners the male ego never wants to give up his control. In my case it was a fight to the bitter end. A fight which nearly killed me. As along the way my old male self seized upon every means possible to preserve his existence and furthermore, he never fought fair. He felt he carried all the cards and only played any when he was pressed to do so. 

Through it all, what he never counted on was the inherent strength of my inner feminine self. Along the way he was ego driven to the point where he thought dressing as a transgender woman was simply a hobby he had to relieve the stresses of the world. When in reality, the opposite was true. She was letting him continue to express his masculine self while she bided her time and waited for her chance to shine in the world. 

As I continued to explore the world as my feminine self, it became clear to me who the winner of my gender struggle would be. Every step of the way in my brave new world felt so natural. Before I knew it my so called even split living life the best I could as a male and a female became more and more female and when I was spending life as a male, all I did was dream of what my next step would be as a woman. Where would I go and what would I do?

Of course the biggest problem I faced was my male self held the power cards such as family, friends and finances. The most powerful card he held was the influence he had with my wife of twenty five years who I desperately loved. She wanted nothing to do with my female and created the ultimate catfight between two women. In the meantime, in protest to having less and less influence in my life, my male self made my existence miserable, ruined my mental health and led me to try a suicide one night. He was prepared to risk my entire life just to maintain his. In addition, he pushed me into more and more alcohol abusive situations. Happily, I was able to end his influence when I transitioned before I seriously damaged my body. 

None of any of that mattered to my male self as he fought the good fight and slowly but surely was sliding down a very slippery gender slope. Deep down he knew every successful moment my novice transgender self experienced, the fewer chances he would have to claim his existence.  In typical male fashion, he moved ahead fighting change at every turn without thinking of the final outcome. In the process, he was making himself and everyone around him miserable. 

Finally he knew enough was enough and with the help of a few very close cis-women friends I took the leap and transitioned into a new life as a transgender woman. The slope I mentioned abruptly ended and I went into a gender free fall. Little did I know at the time how strong my inner female was and how much she appreciated finally being free and having the chance to run my life. 

It turned out she really knew how to fight the good fight since she had been fighting her entire life to live an authentic life. There are days, I wish I would have intervened in my gender fight earlier in life but as it stands now I have to live with what I did. 

Carry on Baggage

My wife Liz (right) and I with
Brutus Buckeye in the
Ohio State student union...

Those of you who have transitioned genders or those who are seriously considering crossing the gender border need to figure out how much baggage they will take along. If you are into sports at all (which I am) this time of year is fun to me because of all the huge football games being played.

So for me, the amount of baggage to consider was considerable. I wondered if my love of sports would have to take a back burner in my life. Because, back in those days, the choices were basically black and white with very little gray. If you remember, there were really only two groups of individuals you could identify with. Those were transvestites (or cross dressers) and the transsexuals who were headed for genital surgical intervention. Plus, after the realignment surgery, you were expected to exclude your past, move from your home and family and start your life all over.  No room for any baggage from your previous existence. 

Today fortunately is different. Mainly because cis-women of all sorts these days have or are living more diverse lives. The lines between male and female genders have been blurred. 

In my case I found out the easy way how much baggage I could bring with me. When I basically gave up on going to gay venues for any number of reasons such as being overall rejected as a drag queen or hating the music. I found I much preferred going back to the big sports bar venues I used to enjoy as a guy. Ironically, I found I was discriminated to less in the sports bars where I could order a large beer and watch my favorite sports team dressed as a transgender woman. Outside of a few notable exceptions I was able to establish myself as a regular by minding my own business and tipping well. I also found I could use all the help I could get as I researched if I could indeed add sports to my baggage as a trans woman.

On a higher level, I even found I could meet other women who were into sports and become friends I could interact with on a regular basis. Over the years I had a great time with them meeting and arguing sports with our tight little group of women.  

When I learned I could take on the biggest baggage carry on I could imagine, the rest of my life became so much easier. I could concentrate on learning from my women friends who happened to be lesbians all I could concerning my new life as a transgender woman. Especially valuable to me was the fact I was finally able to validate my gender dream. In other words, I didn't did a man to be seen with to validate me anymore. 

As I said, the ability to establish my new life and bring quite a bit of carry on baggage with me made my transition so much easier. Hopefully, you will have the chance to validate your new self also and make friends in the process. I would also be remiss if I didn't mention my wife Liz who took a chance on me when she saw my on line profile. She is the cis woman who told me a decade ago she didn't see any maleness in me and why didn't I throw the rest of my male life away and live full time as a trans woman. Her validation naturally was tremendous.

As with any carry on baggage, you naturally will find items you didn't really need but having the time to live a new life to find out what you can't live without, is important as you move on. 

Doing the Right Thing

 

Image from this Thanksgiving 
and the Jessie Hart Archives

At the most successful restaurant management job I ever had in my life, the company's main training point was to do the right thing.

Early in my life, I felt dressing as a girl or woman in any way was not doing the right thing. I suffered tons of guilt as I embarked along what turned out to be a long winding gender road. At certain roadblocks I found I needed to do the right thing again and again. Early examples came along when I needed to learn to dress my age and begin to blend in with the world. Often, doing the right thing for my inner feminine self came during the times I was soundly rejected by the public and came home in tears.

Perhaps the next step came around when I needed I had to finally leave my love affair with my mirror and begin to let the public be my mirror. It turned out it was one of the best moves I had made to that point in my journey. The whole process forced me to communicate with the world as a novice transgender woman and prove to myself the path I was on was the right one and it was leading me past the idea I had entertained for years I was simply a weekend, part-time cross dresser. Mainly because I felt so natural when I was living as a trans woman. 

Undoubtedly, I was doing the right thing with my life but there were so many challenges ahead. The more gender doors which opened, the more doors were still closed to me. A prime example was until I totally committed to living as a woman, I couldn't secure my permission to go behind closed gender doors and play in the girls sandbox.

Finally I arrived at the point where I needed to decide if I would subject myself to life changing hormone replacement therapy. After much soul searching and securing a doctor's approval, I decided to stay on the femininization road I was on and keep going. By doing so I knew I would be giving up what was left of my old male life. All male privileges I fought so hard for were gone and I was still searching for any female privileges which were still to come. The important point is I was still exploring my gender world to make sure I was still doing the right thing. After all, it was a major move. 

Perhaps the final chapter of if I really did the right thing won't happen until my final chapters are written, How will I be treated if or when I have to be admitted to an assisted living  situation. And finally will I be mis-gendered when I pass away. My only younger brother as already said he will never refer to me as my new legal name so that is that. 

In anyone's' life, doing the right thing is often the most difficult road a person can take. Especially when your life involves being transgender.

Thanksgiving and Beyond

Image from Kevin Dowling
on UnSplash

 As much as Thanksgiving was always a given as a time to meet up with family and eat a delicious feast.  Early on, the day was more enjoyable because one of my right wing nephews at that time did not want to start a political argument with me. 

Through it all, in the back of my mind, I knew something was wrong. In my own way, I was engaging in impostor syndrome. I wasn't the man I was portraying to be. Each year I used alcohol to dim the pain and move on the best I could. Even though I had very little control over Thanksgiving itself, there was a day I still thought eventually I may have some control over. The day in question was the Black Friday shopping event my second wife always insisted on going to. This all happened in the latter part of 2005.

Finally, I waited long enough or persisted long enough I was able to try out a Black Friday shopping experience on my own at a well known mall close to where I lived. My opportunity to cross another feminine experience off of my novice transgender woman check list came when I learned my wife (who worked in retail) had to work on Black Friday morning. Suddenly, since I didn't go in to my job until late in the afternoon, I had my chance to experience the shopping madness which was Black Friday as a woman.

When the day finally arrived and my wife left for work, my time to get dressed in my best sweater, skirt and comfortable shoes, added my blond wig, sensible make up and was ready to go. I was excited about finally having the chance to again live my dream. 

Once I arrived at the mall, predictably parking spots were at a premium but I finally found one. From there I had to gather my courage and enter the mall. Once I was in the shopping area, all my nerves faded away and I was able to concentrate on the relatively short time I had to fulfill a long term dream of mine. I wanted to experience the estrogen laden atmosphere of Black Friday.

All too soon, as I browsed a few of the stores for a gift or two, I found in particular no one paid me any attention at all. It was so crowded with mainly women, I was able to blend in with no problem. It was time for me to return to my boring unwanted male life and move on back to my impostor syndrome. I was learning I was never a guy cross dressing as a woman. I was a woman cross dressing as a guy.  

After I went into my work and became immersed in my job, at the least I was still mentally able to bask in the glow of being able to live out one of my big feminine dreams... to experience a Black Friday shopping experience as a transgender woman. As it turned out, my start to the holiday season was destined to grow and grow into one of the major holidays for me. Replacing even Halloween. Throughout the month of December, I will be writing more in depth about my times as I grew into a fulltime trans woman.

Thanksgiving Day and Covid

Just before Thanksgiving I was scheduled to receive my latest Covid vaccination update. I have to go to my local small Veteran's Administration clinic to get a shot in the arm.

We shall see if their amazing transition into an inclusive environment continues. Over the years they used to repeatedly refer to me as "Mr. Hart" or even "Sir". It seemed nothing more than a formal complaint from me could change the way I was treated.

Before I could file a complaint, however the whole place started to change. When I was called to go back for my appointment, I went from "Mr. Hart" to my legal feminine name which is on file with the VA. Plus, now the VA even has a place on their intake forms for transgender individuals.  I don't know what really happened but the change was night and day. I am not for sure but perhaps they changed out head administers for the clinic. I don't really care, I just appreciate the difference.

In addition, I hope I don't have any negative reactions to the vaccine because my wife Liz and I are scheduled to go to a family get together with my daughter's in laws. In addition to great food, I always enjoy the gender affirming experience as I am accepted by everyone. Especially from my transgender grand child. 

This time of the year is always bittersweet for me. In the past my deceased second wife really went all out. From feeding a big family on her own to extensive Christmas decorations, she did it all. Our big pre-civil war era house was ideal for her to serve a big dinner as well as putting up all the decorations. Remembering all of her work makes up the sad part of my bittersweet existence as I had to sell all of my wife's decorations.   

On the bright side (or sweet) part of the season all began when I began to do most all of my Christmas shopping cross dressed as a woman. As the holiday season approaches, I will go into more detail how the entire process worked for me. In the meantime I will tell you it all worked out very well. Maybe too well because I found shopping for others as my feminine self turned out to be a very enjoyable experience. 

I even went out shopping on the infamous "Black Friday" mall day surrounded by many many crazy shoppers who the majority of were women. I learned in a potentially stressful situation in a crowd of people, it is easier to disappear. In the meantime, learning to dress to blend and for comfort became of the distances involved when I went out.

There is much more to describing my experiences as I grew into being a successful transgender woman and how the season helped me. 

In the meantime, I hope you have some sort of family whom accepts you and you can enjoy your Thanksgiving. 

Transgender Day of Remembrance

TDOR, or Transgender Day of Remembrance was observed Monday here in Cincinnati as well as many other places. 

According to the  "Human Rights Campaign" at least thirty three transgender women and men have been tragically murdered since the last TDOR. This total only includes the United States and not the world. I say at least because sadly no one knows for sure how many other deaths could be attributed to gender violence. 

How tragic is it we trans individuals and allies have to observe this somber day every year along with the increasing amount of violence we feel daily. An example to increasing pressure on the transgender community comes from here in Ohio where currently there are five bills pending in the legislature. The bills range from anti restroom bills all the way to restrictions on trans athletes all the way to drag shows. Of  course these bills all are being pushed by a major political party which is not the Democratic one. 

Of course each of these bills do nothing to battle the anti-transgender sentiment in the public's eye which in turn can result in increased violence. It's no secret either, the vast majority of the trans deaths came from the minority community and are younger. 

Much of these statistics are aided by the fact the trans community still suffers from societies' inequities when it comes to jobs, education and health care. And, lets not forget the number of transgender youth who are rejected by their families and end up trying to live on the streets. 

I am fortunate to live in a metropolitan area which has several LGBTQ+ resources but it is never enough. On the other hand, if one life is saved, the effort is worth while. Hopefully you live in an area where similar resources are available. If not, perhaps you have a suicide help line to help if you are having mental health issues because of your gender problems.

One way or another, take the time to remember all of those who tragically died during the previous year and if you are so inclined, offer up a small prayer for those who are still being threatened. 

Stair Step Method

 

Image from Monica Sauro 
on UnSplash...

Every now and then I am asked how I managed to navigate a marriage, a male life and still transition to a feminine transgender life. It certainly was not easy.

I approached it this way, I took it one step at a time. I needed to prove to myself I could take on and conquer each challenge. Early on, the challenge simply meant looking the best I could as a woman. Then it all got so complicated. Each stair step required more and more work, especially when I needed to move fully out of my mirror and take on the world. 

Along the way, I became more goal orientated than I ever was in my male life. Unexpectedly at first  I was surprised when so many strangers wanted to interact with me. The strangers were mostly women who I think were mostly curious of why I wanted to enter their gender world. I needed to quickly add another step in my transition from one binary gender (male) to another (female) and start to communicate face to face with people I didn't know. I was traumatized since first I am very shy and second, here I was trying to modulate my voice to a feminine level and come up with feminine things to say. It was a huge step to take. 

To add into this step, I had to settle in on how I was going to look. No more going to the same venues with different wigs thinking I wouldn't be noticed. Of course I was and as I ascended to the next step there would be no more changing wigs and names when I was meeting the same strangers. As I said, all of this happened so fast, it was a blur to me looking back. 

Other giant steps I took were when I decided (finally) I was no longer a man trying to look like a woman (or cross dresser) and a man who deeply wanted to discard my life and live as my authentic feminine self. If I could climb more steps to get there. I needed to keep trying more and more venues to see where I would be accepted. Which included bathroom privileges. Most of the time I was successful except the notable times when people called the cops on me or I was banned by management. Nothing stopped me though and I just kept trying to find venues who valued my money. I always minded my own business and tipped well, so normally the employee's liked me.

Through all of this, I was desperately trying to negotiate a very serious twenty five year marriage. I guess you could say I was trying my best to build in hidden steps to save what was left of my relationship when all along my second wife hated the idea of me moving towards me living as a transgender woman. 

It wasn't until she passed away, did I take possibly the biggest stair step of all, being approved for and starting hormone replacement therapy or HRT. My body took to the new hormones so naturally, I wondered why I had waited so long. I just couldn't because of the woman I loved as well as being afraid to give up what was left of my male self.

Looking back at all the gender steps I took. I must have been a fairly good carpenter or gender contractor because I was able to arrive at my impossible goal of living full time as a transgender woman. Somehow, I managed to never fall and hurt myself along the way except the times when my ego was bruised which is the topic for another post.  

Mental Health and the Holidays

 

It doesn't take an expert to know we are entering the most difficult time of the year for transgender and/or LGBTQ individuals.

During this approaching time, many in the community face the truth of having no close family any more to celebrate the holidays with. It happened to me when my only sibling (a brother) and his wife decided not to invite me to the annual Thanksgiving Day family feast. We have not spoken since and that was ten years ago. What made it hurt even worse was my deceased second wife used to take it upon herself to cook and feed everyone for years.

Similar to so many aspects of me coming out, I was fortunate in I had a backup plan. What happened was my daughter and my partner (future wife) included me in their families. An improbable happening especially when I needed to mix in with Liz's heavily right wing conservative father. He has since passed on leaving me to forever wonder what he really thought of me. 

So destiny led me out of a potentially bad situation with my own often fragile mental health. As you may, or may not recall, years ago I was diagnosed with a bi-polar disorder along with having more than my share of anxiety. Again destiny stepped in and helped me cope with my mental health . I was nearly completely broke and could not afford my medications when a fellow veteran friend of mine suggested I take advantage of the Veteran's Administration health care. I did and again I was fortunate when I was assigned to a VA therapist who was able to separate my gender issues with my mental ones.

As I said, I was one of the fortunate LGBT or transgender community members who was able to cope with lots of help. To this day LGBTQ women and men are subject to much more substance abuse than the rest of the population because of reasons such as harassment, discrimination,  negative stigma and lack of family support. The basis for the information comes from a site called "LGBTQ+ Substance Abuse and Mental Health Resources"  Thanks to Enmanuel from FloridaRehab.com for the heads up for the site.

I make no secret of the fact I used to be very self destructive due to all the issues I dealt with in my life. From reckless driving in my cars all the way to trying to commit suicide with pills, I had a total disregard for my life. Plus, there weren't the outreach programs available in the pre internet/social media years which I lived through or groups of like minded individuals who provide social activities. Often, if you live close to populated areas, there are organizations you can take advantage of. 

Please, as the holidays approach, see what you can do to help your mental health.  There are sources available.