Opportunity Knocks

 

Civil War Cemetery image
from the Jessie Hart Archives
 

In my life I have found several really rare times where true opportunity actually knocked on my door. 

As I indicated, the situations were exceedingly rare and required split second decisions on how I was going to proceed. Possibly the first main one happened when I went with the "A" list trans women from the cross dresser - transgender mixer I was at in Cleveland. It was the night I gathered my courage, put on my big girl panties and was able to enjoy a professional makeover at the mixer. The result was I looked better than I ever had in my life and really wanted to claim my spot with the other impossibly feminine women in the room who were planning to continue the meeting with going to gay venues afterwards. At the second venue we went to, for the first time in my life as a woman I was approached by a good looking man who wanted to socialize. Since I was in a city I knew nothing about and with acquaintances who were about to call a taxi and leave, I decided to turn his advances down and leave. I often wonder what would have happened if I had stayed. What sort of opportunity if any, did I miss?

 Most likely, the second opportunity I did take advantage of was when suddenly I decided I had had enough of cross dressing and wanted to follow my gender instincts even further. It was the night I was determined to go out and blend in with a group of young professional women at an upscale bar/restaurant I had frequented several times as my male self. More than anything else, I wanted to see if I could blend in with the group as a transgender woman and enjoy myself. Perhaps what I remember most about the evening was how scared I was as I waited in the parking lot constantly checking my hair and makeup before I gathered the courage to go into the venue. As it turned out, opportunity did knock that night. I enjoyed myself after I could take a normal breath again and I knew my life as a casual cross dresser was gone forever. I needed new horizons to conquer as a novice transgender woman.

As I settled into attempting to find my way as a trans woman in the world, I tried to try different venues and situations to deal with. Some were successful, some were not. The ones which I can remember the most were the times I tested going to more or less red-neck country venues. I quickly discovered I wasn't welcome and moved on quickly but not before the cops were called on me a couple of times. No opportunity to succeed in those places for sure and I never went back.

Perhaps the biggest opportunity which came knocking at my door was when I had the chance to begin gender affirming hormones or HRT. At my age of sixty, I wanted to make sure I wasn't going to harm myself, so I took the proper precautions and sought out a doctor to prescribe the medications I had waited for so long. Fortunately for me my health proved not to be an issue and I was given minimum dosages to get me started. Seemingly, my body took to the hormones like I always should have been on them and new changes started almost immediately. In no time at all, I was moved up to a higher dosage and my new changes took over my body. So much so, I needed to move up my transition timetable when my hair started to take off and grow along with my softening skin and protruding breasts. 

Then, the most unexpected opportunity happened when I met my current wife Liz on line nearly fourteen years ago. At my age and transgender history, I was prepared to spend the rest of my life alone and especially never expected to ever be married again. Opportunity was telling me to never say never and here I am.

I have a very hard head however and many times opportunity had to knock loudly to get my attention. Often because I was stuck with life changing conditions where I could lose everything. I tried to fall back on my inner self and hope for the best and finally I let her lead me the right direction. 

Take Your Pleasure Seriously

 

Ohio River image from the
Jessie Hart archives. 

For a gender dysphoric person, the scale seems to be balanced against experiencing any gender euphoria.

 In my case, destiny allowed just enough gender euphoria for me to continue down my gender journey. As I questioned what I was doing, the "why" of it never really came into question. I just knew deep down I was on a process I could not control. It would control me. Deep down inside, regardless of any doubts I may have had dissolved when I felt so natural when I was dressed as a girl. In other words, I was home when I was away from my unwanted heavy male self. 

Still I persisted and tried to find my way in the male universe, I was taking my pleasure seriously when I was dressed head to toe as a woman. I found following one dream (feminine) didn't mean giving up on the other (masculine.) I often wonder, if there was any help available to me back in the pre-internet dark ages would I have had the courage to seek it out. One problem was back in those days we who existed with gender issues were still considered to be mentally ill. Which I knew I wasn't.

The gender unrest I lived through and with was to continue until much later in life. Nearly a half a century to be exact, I gave up any hope of ever returning to a male life and never looked back. Riding a wave of gender euphoria was something I had never experienced before. Living as my authentic self was amazing and even though my male self was still fighting to be recognized. He was to be denied and my life went full circle back to the earliest days of wondering what gender I really was.

By going full circle, I had a lot of ground to cover. In many ways, the world caught up with me. I was able to follow the progression of a term which would describe me and in a very small way enabled me to be a part of a transgender community. Along the way many things changed. Primarily in the terminology which began with what was transgender anyhow and went all the way to the LGBT label which has grown these days to include other letters which includes other communities. Including gender fluid people which on occasion, described how I perceived myself all those years ago. 

During my full circle journey, I learned to take my pleasure seriously. Different than most transgender women and one I don't necessarily recommend, I learned the so called "ropes" of being a single woman (trans or not) in alcohol serving venues. All of the sudden, I found myself in situations where I was the single woman. The positive side of taking my pleasure seriously was when I discovered a small community I could thrive in. The negative side came when I was approached by intoxicated men not in control of themselves. Early on, when I needed some sort of protection, I used my cell phone. Making a big show of acting as if I was talking to another person on the phone who was coming to join me and fill the empty seat beside me. Of course after I gained my small group of lesbian friends, I was nearly completely insulated from the world of men. Also my ideas of sexuality were determined for good. I had way more interaction with women than I ever had as a guy.

Along the way, my new found gender euphoria as I learned to live as a transgender woman began to put my unwanted male life behind me, I had managed to live through the down points in my life and come full circle into a new day. I don't know if the ups have ever equaled the downs but at the least I was never bored.  

Opening Transgender Doors

Image from Nathan Wright 
on UnSplash

What is the old saying, "When one door closes, another one opens." I think the saying is especially appropriate for transgender women or trans men.

Along the way, I have documented several substantial times when I slammed doors during my past and opened new doors. 

Probably the first time I closed a door was when I was going out with a certain set of party friends who ranged from cross dressers to transsexuals who were planning their genital realignment surgeries. I wasn't very interested so much in the cross dressers but on the other hand, I was very interested in the women who were going "all the way." I wondered if I could ever slam the door on the male life I had fought to live and open a new door into a feminine world. 

Luckily I was able to see different sides of the gender coin so to speak. One friend in particular was a firefighter in Columbus, Ohio who was gorgeous and near retirement. So she had the financial risk of a gender transition covered as did the other main transsexual woman I knew at the time. She also was gorgeous and had a very secure job as an electrical engineer. She was so good at living a woman's life, she regularly went on snow skiing trips, spending whole weeks as her authentic self. So, as you can tell, I had lofty role models to try to live up to. I knew they would be difficult to match up to as far as appearance and income plus neither one had a spouse to deal with. I loved my spouse very much and wasn't sure I was able to close the door on my relationship with her. 

Even still, I continued to observe and learn as well as set out to open my own transgender doors. It just took me longer than others to find a path of my own. I know all too many of our gender journey's are similar yet so far apart. It is difficult to leave the first door in our closet and find the other doors in the darkness. Once I was able to find the light and it wasn't the train at the end of the tunnel, I was able to progress quite nicely but not without trepidations. Of course I still had to deal with the usual problems transgender women and men have to deal with when they transition and close the big door. Sometimes closing the door is the easy part compared to opening the doors to different living situations with family, friends and finances. 

I think too many potential transgender folk believe the transition itself will cause the life problems to go away and they haven't thought enough about the all the situations they would have to face now when spouses and/or families want to leave them behind. Not to mention the prospect of losing long term employment and friends. All of the process led to opening very heavy doors and not having much of an idea what the future held. 

I was fortunate when I finally had the courage to open my final transgender doors and face the world. As I did, I could look back at all the times I was petrified to try a new life as a transgender woman. Every time I was so scared it seemed I made it OK which felt so natural and gave me confidence to move forward and look for new challenges. I don't think I ever forgot the two early gender role models I had in Columbus, Ohio so many years before but similar to my male life, I was able to carve out my new life as a fulltime transgender woman so different from theirs.

Even still, I have my doors to open as I face a challenging future with end of life issues. I am still paranoid concerning facing the problems associated with nursing care or assisted living. It will be quite the journey as I face the final door we all have to open and see what is on the other side.

Nonsense?

 

Recently I received this comment from Kendra referring to one of my political posts. Since I am a firm believer in  equal time, here is the comment:

"I am sorry you believe that nonsense about Trump. I am also TG, and I feel none of what you are speaking of. We conservatives are actually a loving caring group of people. Yes, many don't understand the lifestyle, but no one wants to hurt us. Please do not fear us."

Thanks for the comment and the first fact I would like to counter with is I do not fear conservatives and I have often thought of voting for Liz Cheney if she had ever made it on the ballot. To make it clear, I do not consider tRumpt to be a conservative. I consider him to be a threat to our country's security and the basic rights to all citizens. 

Now, let's add in tRumpt calling veterans (which I am one of) losers, bragging about reversing basic women's rights to their own bodies and increasing the national debt four times while he was in office while at the same time pushing through tax breaks for the very wealthy. Plus the biggest one of all, his threat to be a dictator from day one after trying to overthrow the government before (Jan 6th).

Kendra, what I really fear are the transgender citizens and allies who don't realize tRumpt and the paid off SCOTUS is coming after your basic rights. Perhaps you haven't heard of the 2025 blueprint. If you haven't I suggest you research it yourself. 

What I also fear is my hopes for my transgender grandchild's life in the future long after I am gone. At the least I want my grandchild to use the rest room of their choice which is being challenged now in my native Ohio by (yes) a conservative majority in the state legislature. I want them to know I tried my best in any small way to help the transgender and LGBTQ cause. 

I know sometimes I may sound as if I am some sort of a radical left leaning person but I value the counterpoints of having conservatives in the system and I used to have lively discussions when I was in the Army when I was the only once saying at the least Nixon was a crook. 

My deepest desire is tRumpt is never given a chance to advance his agenda against the the country in general and the transgender community in particular. It doesn't take someone in a paygrade higher than mine to recognize that after trans people are erased the bigots will come after the remainder of the gay and lesbian community. 

So Kendra, yes I deeply believe the "nonsense" about tRumpt. 

Un-Common Risks as a Trans Girl

Liz on left. Date Night. 

Most people undertake a risk or two as they make their way to the undertaker in the end. 

When you come right down to it, which person you chose to marry is a risk as well as which profession you choose. Transgender women and trans men seem to have an added layer of risk in their lives. Along the way as we pursue a gender transition, we have to make many difficult choices which aren't really choices at all. They are paths we have to follow or face devastating self harm to ourselves. Which results in extremely high suicide rates in the transgender community. 

When we are growing up in a world where our families often don't accept us, the entire process makes the risk factor even more important. I am so blessed to have a daughter who completely accepts and supports her transgender child and I am proud to have been a role model for my grandchild to follow but it wasn't easy. 

When it came to my marriages, seemingly destiny has led the way into several different areas of acceptance. Acceptance of course led to risks being taken. My first wife was very easy going and knew of my cross dressing desires before we were married and had our daughter who turned out to be my only child. My first wife accepted without question my desire to cross dress as a woman and venture out on Halloween adventures. I often thought if I came home from work one day and told her I was checking into a hospital for gender alignment surgery, she would have said that's fine, just be careful. As it turned out, I was not ready for that sort of surgical risk and would never be.

Then destiny threw me a curve ball with my second wife. The moment I saw her for the first time, I knew I wanted to be with her in the worst way. Even though she too knew I was a cross dresser, she still restored feelings I long ago had forgotten when I was ready to compete with another man for a woman. In order to win the competition I needed to divorce my first wife and move on to a totally different strong woman who knew somewhat of my gender issues. I say somewhat because back in those days I was just learning myself how deep my transgender feelings ran which were to cause strong problems in our twenty five year marriage later on after the newness wore off. From the start, I always thought she would be the one who would help me to break through in my cross dressing world and help me to be successful in my dreams. As it turned out, she wasn't that person and always drew the line if I suggested at all I wanted to go further into the transgender world. By the time she had passed away, our relationship had deteriorated into an ugly cat and mouse game of me taking risks and seeing what I could get away with.

Another main risk I took was with my job. Slowly but surely I had been promoted through the managerial ranks to a successful position as an executive general manager of a big popular casual restaurant chain. A position with a company I knew would not accept me transitioning into a transgender woman. In my haste to destroy myself anyhow, I began to go to my competition as a woman thinking no one would recognize me. Well, I was wrong and the roof began to fall in on me. It was tough but I denied all the rumors and kept on going.

By this time, my second wife's life was coming to an end and she suddenly without warning passed away from a massive heart attack. By this time I had purchased my own restaurant and was somewhat in control of my own financial destiny until a recession in the Rust Belt where I lived wiped out the population. I ended up losing my restaurant as well as my inheritance by taking a major risk and losing nearly everything I had. I finally was able to find me a fast food job to hold me over till I could take an early retirement from Social Security and sell vintage items my wife and I had collected over the years. Between the two I survived.

I then found myself in a period of wonderful gender discovery, when with the help of new women friends everyday seemed as if I was reborn. Specifically Kim and Liz helped me the most. Liz lived in nearby Cincinnati and we met on line. After corresponding by email  for months, I finally became brave enough to talk to her in person and our first date was at a drag show. That date was nearly twelve years ago and we are coming up on our second anniversary of marriage. Liz cemented her place with me when she told me she had never seen a man in me and why didn't I finish my transition into a feminine world with her.

Finally, after a half century of wondering and suffering over my gender dysphoria, someone else recognized my truth and wanted to accept it with me. My un-common risks were over. I accepted her advice, gave away my male clothes and never looked back.

Being Afraid to Try

 

Image from Jas Min on UnSplash

Since it took me nearly a half a century to fully leave my dark lonely gender closet, I have to assume there was an extraordinary amount of fear which was holding me back.

As life progressed for me and I became more and more entrenched in a male lifestyle I never really wanted, it was harder and harder to let go. I had a family and spouse who I loved plus a job I was progressing in. So it was not an easy decision to give it all up. 

It all finally came down to what my wife told me after one of our gender based arguments. She told me why didn't I man up and become a woman if I was so enamored with the idea. Had I followed her advice, I would have saved both of us so much turmoil over the years to come. By now, you know the story. I was stubborn and tried to live with one foot in the male gender world while at the same time learning if indeed I could live as a transgender woman. 

Through it all, even since I was taking small steps in my gender journey, the fear of not being able to make it as a full time transgender woman kept creeping back into my life. My scope became so much larger than just admiring myself cross dressed in a mirror to attempting to try the world in costume as a woman during Halloween parties. What kept me going was I felt so natural as my feminine self and then wanted to experience more and more. 

I write extensively about my experiences as a novice transgender woman. Even if I was petrified to try new experiences in the world, I pushed myself to still do them as my age was catching up to me. I wasn't getting any younger and all of a sudden, family and close friends around me began to pass away. Making my mortality even more of a reality than my gender dysphoria. Finally, when I reached the age of sixty and was exploring my life increasingly as a trans woman, it was time to act and put my fears behind me. Realistically, I knew I wasn't going to have a better chance to transition so I better do it. Setting all my fears aside and living in a feminine world turned out to be the best move I could make. I lifted a ton of weight from my shoulders when for the most part, my life restarted again. It was around this time when my new gender affirming hormones (HRT) were starting to change and control my body. Along with developing breasts and softening skin, my whole world softened and I felt emotions I never knew I had.

Now, I am so glad I wasn't afraid to try. My only disappointment is I waited so long to do it. Fear finally turned out to be a powerful motivator for me as it turned potential panicked situations into  successes. Rest rooms were a prime example of success or failure. 

This blog itself is another example. Way back when I was given the idea to write about my new experiences in this world, I didn't even know what a blog even was. Now with well over seven thousand posts and four million hits, it is time to stop and thank all of you for taking your time to stop by Cyrsti's Condo to visit. I have always embraced and enjoyed your participation and all I can say is I am humbled and flattered. 

 

Lesbian Bars

Image from the
Jessie Hart 
Archives.

When I was first exploring the world as a novice transgender woman, one of the first big discoveries I made was the male gay bar scene was not for me. 

I initially thought going to a gay bar was a safe place to be. I found I was safe, to the point of not being threatened but on the other hand I did not anticipate being ignored to the point of being discriminated against. Since I knew the odds of anyone hitting on me would be very low, again I was lonely all the way to the point of being ignored at the bar when I tried to order a drink.  Also, I disliked being treated like a drag queen on nights when there was a show. Within a short period of time, I grew tired of the experience and looked for other outlets to explore.  

About that time, I became aware of several new lesbian bars which had opened around the Dayton, Ohio area and wondered how my acceptance would be at them. Since my sexuality had never changed from liking women, I felt more comfortable in their company and wanted to see if they accepted me at all. Not to be "picked up" so to speak but to be treated on a friendly basis. Initially, I knew of three lesbian bars of which I tried to go to two. 

The first one I tried did not accept me at all. It was a very butch dominated bar where I got in trouble for playing Shania Twains "Man, I feel Like a Woman." The lesbians huddled around the small bar did not see the humor in my choice of music. Even though I wasn't welcome, I still persisted on going back just because I was so stubborn. On the other hand the second lesbian bar I went to was a completely different experience. They were friendly to me and I felt relaxed and welcome. Plus I was surprised when I discovered my male self actually knew one of the bartenders. Her and her wife were regulars at my restaurant. 

As it turned out, I had many exciting experiences there starting with how I presented myself.  Quickly I assumed the role of a "lipstick lesbian" in my boots, tight padded jeans and blond shoulder length wig. One night I presented so well, a "super butch' (very masculine) woman approached me to sing karaoke with her. She would not take no for an answer so I joined her along with her cowboy hat for a terrible duet. Since I am a terrible singer. When I finished, my singing partner said she was surprised my voice was deeper than hers as I began to plot my escape. While she took off to the restroom, I took off to pay my bar tab and left and I never saw her again. I know my friend behind the bar got a kick out of my whole experience. 

One night I am still sad I missed was when the bar scheduled a few exotic dancers to come in and entertain. The small venue was packed as everyone eagerly awaited the show and one of the other patrons actually bought me a beer and said she ought to take me home with her. Even though I was flattered, at that time I still had a wife to go home to and time was running short. I could not stay until the exotic dancers made it, so at the least I saved the tip money I was going to use. It was to be the only time in my life I would get the chance to experience how a group of women act around dancers.  

I was saddened when the bar closed and I had fewer venues to go to but it was a time of great discovery for me anyhow. My new small circle of cis-women friends were lesbians. The fun started when I began to receive invites to come along to monthly lesbian only mixers at different Dayton, Ohio venues. Some were straight while others were gay which made going even more exciting. One night, one of my friends even asked me to approach another person at the mixer for her to see if she was with someone else which marked the first and last time I was ever a "wing person" for another woman. 

Probably, the biggest lesson I learned about the lesbian community was the different layers of people from "Baby Dykes" to "Lipstick Lesbians" all the way to "Butches and Super Butches." I found for the most part I fit in except for one night at a woman's Valentines' Dance years ago when a bigoted TERF attacked me about being at the dance at all. At the time, my future wife Liz was part of a Cincinnati lesbian social group which I tried to join also. When I was turned down, Liz left the group. 

As you can tell, I owe quite a bit to lesbians and their bars which sadly have disappeared in many areas. I know of two still left in my local Cincinnati area but there could be more I have not heard of since we don't get out much anymore. I just know the venues I went to in place of gay bars were a welcome relief to my acceptance as a transgender woman. When I combined them with all the straight venues I had become an accepted regular in, my new life was off to a good start. 

Ownership, Skeletons and Politics?

 

My daughter's favorite saying used to be something to the fact if you have skeleton's in the closet you better make them dance. Which could describe many politicians in Washington DC.

This post however is not another rant on my part about politics. If you follow me at all you know I am solidly behind the Biden-Harris ticket and believe tRumpt and his cohorts want to erase transgender people everywhere. As well as do away with our democracy. But, as I said, this post is not about politics, it's about my life. 

In my case, I spent most of my life trying to change the inevitable. I was transgender and should just relax and make the best of the situation I found myself in. By cross dressing my life away, the only positive I can come up with is all the practice I put into the art of feminine makeup and fashion. It wasn't until I left the mirror and started exploring the world, did I begin to own it. The whole process turned out to be a blur and actually happened faster than I dreamed it would. In other words, by interacting as a transgender woman in public, I was teaching the skeletons in my closet to dance. 

The dance moves became more and more intense when the public wanted to invade my little private world and know more about me. First of all, when I finally moved from the easy clothing stores in the malls I used to shop at and into food venues where I would stop to eat. Then I found myself needing to communicate with servers and bartenders one on one as I was scared to death. At first I tried to mimic the range and tones of the women I was speaking with until I found I could take advantage of feminine vocal lessons at my local Veterans' Administration hospital. Slowly, I gained enough confidence to get by in the world. I was coming to realize I could not change who I truly was, so I better learn to know her better. When I did, I enjoyed the person she was, My feminine inner soul went way past just trying to look good in the mirror and do a better job with my makeup and fashion. I found I could just let her go and I could set back for a change, watch my skeletons dance and enjoy the show. For the first time in my life I did not have to feel guilty about the person I was becoming.

In addition to having less guilt, I was having the time of my life. For the first time, I was making new friends who had no connection at all with my old male self. My small core group of mainly lesbian women friends taught me more about owning who I was than they ever knew. I was validated as a transgender woman through them mainly because they saw me as me. The freedom was remarkable. 

Perhaps I could say I transitioned to my authentic self  not so much because of my friends but on the other hand, I started to own my life and live it with my friends. I was teaching my skeletons all new dances when I let them out of the closet. As always my old male self was resisting losing his grip and it took my wife Liz to send him away. When we first met, Liz barely knew what was left of my former self and she told me she never saw anything remotely male about me. That was it and from then on I went all out to own who I really was. 

See, I told you this was not going to be a political post, Now if you will excuse me, my skeletons are dancing for the public to see.  

It Was so Much Larger than I

 

Jessie on right with Tom
from the image archives.

Back in the so-called simpler days when I was growing up, putting on a dress, adding makeup and acting like a girl was quite the rush. The mirror meant everything to me and I couldn't wait to show myself out to it again and again.

It took me awhile to grasp the idea I wanted to do and be more than just a girl in the mirror. I wanted to be the girl. It was my earliest fundamental idea I was so much more than just a casual cross dresser, if the knowledge had been available to me, I would have labeled myself as transgender or at the least gender fluid. Bottom line is however you want to label me, the whole process was so much larger than I was.

From that point on, anything I did in life was predicated on my gender dysphoria. Each person I decided to establish a friendship with, I needed to wonder if they would ever accept the feminine side of me. The whole process led me to be very standoffish with most strangers and developed very few close friends. Of course the idea of marriage became a huge obstacle. I knew I wanted female companionship but did not know if marriage could ever be possible for me. The end result to any relationship could ultimately finish because of my gender issues which made me wary of knowing anyone. 

Eventually, I was able to work around many of my gender issues and my world broke open once I was in the military. It was there I met my first wife and future mother of my only child. She was unplanned since I was out of control in my life as I busily went about running from my problems. Becoming a father turned out to be so beneficial to me as it settled me down and I figured I could put off telling her her father was really a second mother of sorts. 

Through it all, I tried my best to keep running from my gender dysphoria. Mainly from abusing alcohol, changing jobs and moving homes. I became a gender survivalist. Still being very careful around strangers and keeping up my well crafted male persona. It was working as well as could be expected until I met my second wife. She knew I was a cross dresser from the beginning so I thought I had it made, a strong woman who accepted my feminine self. What I did not factor in was again I was more than a cross dressing man, I was a transgender woman lying to herself. When she married me, she made it clear she wanted nothing to do with living with another woman. A fact which would come back to haunt me totally in the future. 

My second wife and I managed to navigate a very complex relationship for more than twenty five years before she passed away. Sadly, during her life, I became increasingly active as a transgender woman and ended up cheating on her with another woman, who turned out to be me. As I was continually lying to myself, I was creating major problems for our relationship and my mental health. After she had passed on, I finally met my wife Liz as well as other female friends who convinced me my life as a trans woman was not larger than I. The more I emerged into the world, the more I understood my feminine inner soul was always the dominant person in my life and she was more than ready to take over. The easiest way to explain it was it all felt so natural when she was calling all the shots in my life. 

Little did I know, the half century I spent exploring my cross dressing world was little more than a huge build up to a new exciting larger life.  

Prom Time

 

Image from Amy Kate
on UnSplash

I graduated from high school way back in 1967 and where I went to school in Ohio, going to prom was a big deal.

I was very shy and as it turned out my junior year in high school prom was my first date with a girl ever. I didn't even really ask my date out, it was pre-arranged by her friends who knew she did not have a date nor did I. So I was set up for success. 

Of course success for me was scary. I had no idea how I could ever spend an entire evening with a girl. What would I say? How would I even communicate? The only real interactions with girls were with my Mom. All others just seemed to be up on a far away pedestal I had invented. Then my gender issues came crashing in to make my problems even larger. All I really knew was deep down inside, I wanted to be the one wearing the pretty fancy gown rather than the restrictive monkey suit called a tuxedo. Worse yet, I had to spend my own hard earned money to rent a tux. 

It turned out renting the tuxedo was only the beginning of my expenditures. I was fortunate at the time to have had a very well high school paying job so my parents did not have to contribute much to my initial adventure with a girl. In order to go all out for the evening, tradition was the guy paid for nearly everything from flowers, to dinner at a supper club, to tickets to the after prom which was a way to spend the entire night out. What I didn't factor in was how much my date had to spend on finding a dress, having her makeup and hair done and of course locating matching shoes. All of the processes the girl went through for prom to me felt like a labor of love to me I couldn't have waited to try. 

My date's parents were doctors so Dad even went the extra mile and let me borrow his car for the evening. Needless to say, I was scared to death in my tux when prom time approached. Somehow I managed not to blurt out anything stupid when I was introduced to my date and let her Mom put the corsage on for me on my date's spaghetti strapped gown which I loved and told her so. Just didn't happen to mention just why I loved her dress so much as I wondered how it would look on me. Fortunately, we were meeting another couple for dinner, so I didn't have to feel so stressed about carrying any sort of a conversation myself. So far so good, my first date was coming off without a hitch and ironically I was able to experience some sort of transgender revenge when I went to the old supper club when it became a gay venue. I was there one night and was able to use the women's room completing some sort of gender circle in my mind.

By the time my senior year rolled around, I was a seasoned prom pro and ended up going to two proms in one night. Since I was dating a girl who went to a competing high school, we decided to go to both proms. I even drove my own car since she was familiar with it and I didn't have worry about asking my Dad for his car. Overall, I managed to have a good time since I wasn't so frightened of the whole experience. For the rest of my life, my prom experience was over. For better or for worse. 

Probably, my parents were relieved I was finally dating girls. I on the other hand wasn't doing anything to relieve my gender dysphoria. I still wanted to be my girlfriends and live their lives. My cross dressing tendencies continued all the way until I was drafted into the military and had to stop for obvious reasons. By this time, I had more to worry about than how I looked as a girl. I was looking at surviving college so I could stay out of Vietnam as long as I could.     

Today I see the young high schoolers seem to view proms as less structured affairs than we did so long ago. It's all for the best.

Transsexual Harassment

 

Pow Wow Image from the
Jessie Hart Archives. 

In a previous post I promised to write about the times I was sexually harassed as a transgender woman. 

The first time I experienced harassment came when I attended a nearby mixer/party with my second wife in Columbus, Ohio. The parties were relatively small but very diverse group. Anyone from cross dressers to transsexuals headed for gender surgery to male admirers attended. 

To begin with, my wife did not approve of the outfit I was wearing, saying it was way too short to start with. Of course I did not listen to her and went with the dress I wanted to wear anyway and yes it was very short on me. Even to the point of making it very uncomfortable to sit down even though I had freshly shaven legs and new panty hose.

Once we arrived at the party, I grew restless and needed to move around. Space was limited in the small house of the host so everyone was basically confined to the living room. There was also a hallway which led to a bedroom and bathroom. When I did get up, I didn't notice one of the male cross dresser admirers got up to follow me also. I was/am a big person and had never experienced any problems with my size before and was shocked when I saw how big the person who was suddenly stalking me was. Before I knew it, he had me cornered in the hallway and for the first time in my life I felt helpless. I didn't know what I was going to do until I looked up and saw my wife glaring at both of us. He saw her too and immediately backed off and the threat was over but not before my wife gave me the I told you so lecture concerning what I wore. Even though deep down I knew my wife was right, the deeper meaning of what happened to me never went away.

From that point onward, I knew how a woman could be overpowered and sexually assaulted by a man. I found out the difficult way, once I put on heels and hose and cross dressed as a woman, my male privileges changed forever. Gone was the idea I would not be stalked and attacked on a dark lonely city street or parking lot. Of course I needed to learn the safety lesson the hard way too. 

When I first came out of my gender closet, I frequented my share of three male gay venues clustered together on a city block in downtown Dayton, Ohio. Once I made into the venues themselves, I normally did not have any problems. It was when I was going back to my car one night, I ran into problems.  As I was walking down the sidewalk, I was approached by two men who ended up stopping me. I was lucky that night and was able to "buy" them off with the last five dollars I had. 

From that point forward, I told myself I would be safer where I went. I made sure I parked in lots which were safely lit and park as I could to where I was going. I even would ask friends to follow me to my car when I was out. I was lucky to escape any actual harm when I first ventured out of the closet as a transgender woman. I discovered negative harassment in no way validated me as a woman. All it did was put me in danger. In fact, it wasn't until I began to hang out and visit my lesbian friends did I learn I didn't need a man at all to validate my existence, transgender or not. 

Once I learned losing my personal safety as a former man was behind me, I could move forward and recognize what being an out and proud trans woman was all about. Transsexual harassment became an unwanted and unneeded determent to my life.   

A Toxic Male?

Image from Jurien Huggins
on UnSplash.

As I transitioned from a male to a feminine life, I often looked back at my life as a guy to determine if indeed I was a toxic male in any way. 

Of course I immediately mentally recoiled when I thought I could be toxic towards women in any way. After all I had spent a considerable amount of time worshipping the women around me, wondering how it would be to experience just for an instance being a girl. How come I couldn't wear the pretty clothes and be the gender who was so admired by the other. The problem with me was, I went way past just admiring a girl sexually, all the way to wanting to be a girl physically.  

Did any of it make me a toxic male? No, I don't think it did. In fact, I think the opposite happened as I put women up on some sort of an impossible pedestal. By doing so, and adding the fact I was extremely shy, I never had much of a chance to interact with girls or women growing up at all. From my perspective, the feminine grass always looked so much greener. 

Since I was forced into the male camp, I needed to learn to exist and had to put up with sexist comments directed towards women from many of the guys I grew up with all the way to adult hood. Mixed in too were the bullies I needed to somehow co-exist with. I learned to bluster my way around the bullies without jeopardizing my inner transgender self to ridicule or worse. In order to do so, I participated in as many of the male activities of the day as I could such as sports and cars. It worked and I was left alone for the most part and I even dated a few girls along the way. Since it is prom season around here, I am always reminded of the two proms I went to in high school. Even though I was the perfect gentleman at the proms, I wonder if my dates thought perhaps I was a little too timid and took it personally. I will never know because one of my dates and first serious girlfriend before college later in life committed suicide years later when her husband left her. What a shame. 

As I started college and started to date more regularly, I really began to see the results of toxic males around me. Especially in the fraternity setting I was briefly in. Certain fraternities were expected to co-mingle and party with certain women and sororities only where I went to college. I found out very quickly I did not fit in with the frats social system. Which was a forerunner to me not fitting in with the strict layers I encountered at the first cross dresser - transvestite mixers I went to. I felt so out of place and the only toxic people I saw were the "A" listers who were doing their best mean girls high school impressions. Maybe their male toxicity was bleeding through. 

I completely learned how not to be a toxic male when I settled into a career in the restaurant business. Along the way, as I progressed into higher management positions, I needed to coexist increasingly with women. Both crew members and managers. I learned quickly female crew members had the tendency to build cliques (not teams like the men) to be successful and the women managers I knew had to be tough but fair to survive. I on the other hand needed to be on their side when it came to battling any toxic males at all. Looking back, I think male toxicity was the prime reason for letting someone go. Which included sexual harassment which is a topic for another blog post.

My only regret was I wasn't a more vocal advocate for women my entire life as a man. I could have certainly spoken up when another guy joked about a woman. My only excuse is I was so intent on hiding my interior feminine self, I was afraid to do more. Transgender women and trans men speak of the importance of allies speaking up for us. I feel the same way about standing up for women before I transitioned. 

Being Prepared for a Transgender Future

Image from Chad Walton
on UnSplash.

For nearly a half a century, I hid behind the idea I was nothing more than a cross dresser who liked to wear women's makeup and fashion. What harm was I really doing? The answer is, the only harm I was doing was to myself.  

Had I known all I was doing was to prepare myself to transition into a transgender woman later in life, I may had approached the process in a different light. The problem was, everything seemed to be so life and death serious. Primarily since I was locked into a very lonely, dark gender closet. I had no role models around me to prepare for a highly uncertain future. No one to tell me my make up looked clownish and my skirt was way too short. I only had my old male ego and a mirror who were teaming up to make my life miserable. 

I really learned how miserable I could be when I began to leave my closet and explore the world.  Being stared at and laughed at to my face taught me the mirror could lie to me and the way my old male self was telling me to dress was all wrong. I was going back to my cross dressing drawing board too many times before I learned what I had suspected all along, becoming a part of the feminine gender was going to take a lot of work. I needed to go so far to finally understand all along I was a woman cross dressing as a man and not the opposite. 

The more I began to understand where I was in life, the more the future came into focus and preparations for major upcoming decisions became important. As I was exploring and building a new life as a novice transgender woman, it became clear to me I could indeed live my dream of living as a woman. Before I could arrive there, I still had heavy preparation work to do. There were major issues of coming out and telling what was left of family and friends I was a trans woman. Once I did, there would be no more running home and hiding in the mirror wearing a dress, The first person I told was my only child (my daughter)  went very well and I was emboldened to tell more people such as my only sibling ( a brother). He accepted my transness terribly so I ended up with an even split in salvaging any of the family life I had left since my parents had long since passed away.

The next crossroad I needed to navigate was what was I going to do about supporting myself in my new world. Following quite a bit of planning and preparation, I decided I was close enough to being able to take an early Social Security retirement which back in those days was sixty two. To get there, all I had to do was work another two years. Ironically, during the two years, I was able to prepare even further for my future when the Veteran's Administration Health Care System I was part of suddenly began to accept HRT or gender affirming hormones for veterans. So, the extra two years gave me the time to further prepare for a future which included changing all the legal gender markers I could including a new legal name. 

Since I was newly single again following my second wife's sudden passing, I really could use the time to prepare for the final transgender transition into a new life I had been preparing for since I was born.  

Saving my Own Life

Image from Alysha Rosly 
on UnSplash
 

 
I make no secret of my Bi-Polar mental condition which went undiagnosed for a good part of my younger life. 

Ironically, it was my first gender therapist who connected the dots and determined my condition when I told her I often spent days struggling to even get myself out of bed. I just thought I was riding the waves of gender dysphoria  which kept me so depressed or elevated when I was experiencing brief moments of gender euphoria. During this time of my life, I was far from being the easiest person in the world to live with. At the least, I was prescribed medications which evened out my moods. The meds also helped me sort out my gender issues and finally figure out one mental issue had nothing to do with the other. In fact my gender dysphoria was not a mental issue at all but instead an organic one. Had I listened to my therapist, she was trying to tell me all of that but I was unwilling to listen. Primarily because at the point of my life I was in, I was still a novice transgender woman and didn't know if I could live my dream life.  There were still too many gender bridges to cross such as telling family, friends and bosses I was transgender. 

The furthest I had come at that point was telling approximately five close friends and spouses I was a transvestite. A long way from living as a transsexual with all the resultant rules I would seemingly have to follow Such as major gender operations, moving away and then starting all over again. To make matters worse, I hadn't even thought much about my sexuality. Would I suddenly desire men sexually? I was overwhelmed with all the big questions and just continued my life as a very serious cross dresser. At the least, I was able to work on my presentation as a woman and go from there.

Even though, my solution was far from perfect, I was saving my life the only way I knew how. The problem kept reappearing when I started to go out more and more behind my second wife's back. When I did, I fairly quickly began to build up a robust life as a transgender woman. Every step I took, the more natural I felt when I could never see how I could go back to living a male life. The whole process created tremendous pressure on my already fragile mental  health. I became increasingly self destructive, all the way to an unsuccessful, ill advised suicide attempt. Essentially, from the point of suicide, I purged most of my feminine belongings and even grew a beard to prove to my second wife I could do it. By doing so, I was intensely unhappy for the short time she lived until passing away from a massive heart attack. I often wonder what would have happened with us had she lived.

Following the tragedy in my life, over a short period of time, I regathered myself and refocused  on a new feminine life. I quit dwelling on death and began living a preferred life as a transgender woman. By doing so, I was all of a sudden needing to quickly learn more than I ever imagined about my new life. Throwing out or giving away all my male clothes was at once liberating and  on the other hand, very scary. I had never purged my male self my entire life and he resisted. 

Regardless, scary or not, the process of a gender transition saved my life. Over a space in time, my mental health has stabilized and with the help of gender affirming hormones, for the first time in my life, my body and mind are beginning to mesh. The entire process took me a lifetime to figure out but as I always say, it all was so worth it. 

One Gender Size does Not fit All

Image from Grae Phillips 
on Geraldo television show.

 If the truth be known, all the way back when I was a kid struggling to understand what gender I was on any given day, I would have been known as gender fluid. 

Of course, gender fluid was a term which hadn't been invented yet. Anyone who was interested in cross dressing was branded as being a transvestite and even worse labeled as being mentally ill. In the middle of my gender vacuum, even I knew well enough I was not mentally ill just because I wanted to wear makeup and dresses. I hid my desires and hoped for the best, which mostly came when I was left alone to cross dress and admire myself in the full length hallway mirror at home. Most of all, I was trapped and could do nothing about it. Keep in mind, all of this was happening in the information "dark ages" before the internet and social media. The gender underground I was interested in came mainly from the pages of Transvestia Magazine and Virginia Prince. Even I knew the pages of the "National Enquirer" and other predecessors of Faux News who sensationalized cross dressers were not to be trusted.

Then came the barrage of so called reality television talk shows including, Donahue, Springer and Raphael. All of whom seemed to be pushing the theme of cross dressing husbands Except for the impossibly beautiful and talented "Grae Phillips" who put everyone else to shame. All of these shows probably did little or no good for my gender dysphoria except for publicizing the fact there were cross dressers of transvestites of all kinds at all. All I knew was I desperately tried to watch or tape every show I knew was coming up from my "TV Guide". My wife was trying to tape her soaps and I was trying to tape my talk shows and both kept us busy. Even though I still had to watch my shows in private attempting to learn anything I could about the outside world.

I did learn once again. my gender size was unique and did not fit all. In fact, I still felt out of place when I started to attend my first cross dresser - transvestite mixers here in my native Ohio. I discovered there were so many different levels of participation from transsexuals headed for gender surgeries down to the weekend cross dressing hobbyists.  For some reason, I was not part of either group and once again my gender size was not fitting in. The problem was, all of this happened before the transgender terminology was introduced. When it was and I started to have access to my first computer, I was able to research the term which was unknown to me. Suddenly I knew what had been missing my whole life, a gender size which fit me and I set out to discover more about being transgender. For me, it meant being part of a gender description which was somewhere in-between the spaces I had been in previously.

Even though my gender size did not fit all, finally I was able to locate my own niche to thrive in. Life became fulfilling, scary and exciting at the same time. I found out I was fine being who I was all along and it felt so natural. I was home. 

You got it...Now Live with It!

 

From the Archives, Club Diversity. Columbus 
Ohio.

For some unknown reason, I have been remembering more and more what my gender therapist told me so long ago, she couldn't do anything concerning me wanting to be a woman. Now I don't remember if she told me I could not do anything about it either. 

If she did and had I listened, I would have saved myself so much inner torment over the years from my gender dysphoria. At the time my male self was not even close to being ready to give up any claims to his life which at the time was becoming relatively successful. After all, he had worked long and hard to arrive at the point where he was. 

If I wanted to blame anyone but myself for not accepting my true authentic self, I would blame my home environment. I grew up in a very male dominated family. My Dad had two competitive brothers and his competitive personality filtered through to my brother and I. It seemed no one had girls in the family and if they did, they were second class citizens. How I existed was by keeping my true feminine desires a deep dark secret. I learned early the very male trait of internalizing any negative thoughts or ideas. The whole concept turned out to be very self destructive over the span of my life which included the years of being a very serious cross dresser or transvestite. The whole process nearly took my life before I finally figured out I had it, now I needed to live with it. 

All I wanted was the impossible. Give me back just a fraction of the time and effort I had wasted by trying against all odds to maintain any sort of a male life. The cruel and unusual punishment came in when the more I achieved as a guy, made it more difficult to give it all up. I had a spouse, family, friends and good job to suddenly consider. What would my daughter think? Not to mention my wife and brother. All of a sudden I needed to draw a line in my gender sand and decide which route in life I was going to take. 

Everything changed for me the night I finally decided I had put enough exploration as my feminine self to make the ultimate leap over the gender border. Needless to say, it was a huge weight off my shoulders. I had a chance to go back in life to a point where I was not so jaded by either gender and experience for myself what the future held for me. It was at this point friends jumped in and showed me the way I never thought possible. I found I had it all along. I was a transgender woman and now I had the rare opportunity to live with it. I discovered there was so much more I needed to learn when I entered the world as a trans woman. 

Plus it took a while for the overall excitement of transitioning into my dream life to wear off. Everything I did was new and different and even when I was not accepted, I learned from my mistakes and for a change, my inner stubborn streak served me well. I had it and now I was living with it. I guess if you are able to live long enough as I have, you have the opportunity to see life go full circle. I paid my dues as a guy and what he learned turned out to be beneficial in my new life as a woman.

Quoting the singer/songwriter Joni Mitchell song "Both Sides Now",  only when I was able to see the world from both sides of the binary genders, was I able to relax and enjoy my life. All along I had it and just missed out on the real possibilities of what I was missing. Living with being transgender was all that mattered.

Smiles Equal Confidence

 

Go Ahead and Smile from the
Jessie Hart Archives. 

Where ever I go in public, I try to lead with a smile to ultimately disarm any potential transphobic individuals. 

I have to remember also I look better when I soften my face which still has a tendency to go back to my old male scowl if I am not careful. A male scowl in my world always comes off as a bitchy look which I normally am never feeling. 

The whole process goes all the way back to the days when I was cross dressing my way to the front of the mirror. Since all the ups and downs which followed, I needed to learn to put my feminine image in motion if I was to succeed in following my transgender dreams. Since recently I have been getting out into the public's eye more and more again, I have needed to reinforce wearing a smile to boost my confidence as a senior trans woman. This morning was no different when I went with my wife Liz to her eye doctor visit. 

After I applied a light amount of makeup to go with my casual outfit, I thought for once I looked presentable for the world. I even tripped off my gender euphoria for a brief second. My euphoria lasted until I went through the door into the doctor's waiting room. For the briefest of time the two receptionists just stared at me and finally said how could they help me. Not the friendliest of greetings and I became worried about my presentation. Since I had quite a while to ponder the situation, I came up with the problem and it was all me.

I had forgotten the most important part of my presentation which is my smile. For the greatest majority of the public I face, a smile disarms them and allows me to communicate with them on a one on one basis. Plus when I am smiling, I am showing the confidence I need to enable the people in my world to be more friendly also. Most importantly, a smile is my best accessory when I use it properly. Not using it at all takes me back to the day when I was shopping for clothes and suddenly nearly ran into a girl child who was darting between the clothing racks. When she stopped and saw me, she exclaimed to her Mother "Look at the BIG woman." I had long enough to consider the kid at least called me a woman. Then she ruined the feeling by calling me a "BIG Mean woman." From then on I resolved to try to put a nicer look on my face and not scare the public with my bitchy look. 

After living a long unwanted life trying to exist in a male world, some habits are still hard to erase. Putting a smile on my face shouldn't be such a big deal but it is. So big, the whole process is as big as makeup, fashion and hair. Putting the whole image into motion is what counts for me to be truly successful as a full time transgender woman.  

Tenacity of the Transgender Tribe

From the Jessie Hart Archives. I am
in the middle of two friends.

It's no wonder so many women don't trust a transgender woman's desire to play in their sandbox. In my case, it took me years to understand what my second wife was trying to tell me about being accepted as a woman in any form. It took more than just appearing convincingly as a woman to come closer to being one. I was far away from paying my dues and for the most part, she was against me doing it. So, I needed to step out on my own to discover the world on my own. Thanks to all the years of practice in front of the mirror with my makeup and fashion, I had a fairly good basis to work from as far as my appearance was concerned. The only real problem I had was living through my faux fashion adolescence when I tried and failed to dress as a teen girl. Once I made it through that point, I was able to blend in with other women  my age and discovered I had an easier time in the world.

The more I explored, I found I needed more and more tenacity to reach my goal of learning what living the life of a transgender woman could or would be like. At this point the true struggle began. Just learning how to communicate with other women on their level turned out to be the main problem. I learned the hard way women communicate on more levels than verbal ones and often say things of a passive aggressive nature such as, you look good...for a man dressed as a woman. Or they were just trying to find out what you were doing in their world. On too many occasions as I was learning my way around the sandbox, I ended up suffering serious claw marks up my back. Another way to put it might be to equate the acceptance process with trying to jump on a moving merry-go-round and claim the prize without doing any of the work such as having periods. Rejection was not rare. 

It was on nights such as those, I went home in tears wondering if my whole transgender dream was worth it. On those occasions, something told me it was and my tenacity kicked in. Even with more explorations to do. I just had to continue until I got it right. Finally I did and I moved along to adding gender affirming hormones or HRT to my list of exploring ways to better femininize myself. Perhaps then and only then did other women see I was paying my dues to be admitted to their world. I had the tenacity. 

As I reach the age of seventy five, I think now, more than ever before in recent history the tenacity of the transgender tribe of women and men is being tested. Here in my native Ohio, the gender bigots in the state legislature are once again trying to push anti-transgender restroom bills in the statehouse. Hopefully, once again, more rational minds will rise up and reject the measure. If not, I wonder how the whole law will affect me using the restroom which matches my transgender status in the future. Needless to say, I am scared.  I mean how will such a law even be enforced if I am just trying to go to the bathroom. I don't want to even know. All I do know is I won't go back to using men's bath rooms after more than a decade using the women's room. 

Finally, what the bigots don't realize is, the trans tribe has been around forever and is not going away. We just need to move forward as a group to fight. Once the bigots see we are not going away, they will have to find someone else to harass and our tenacity will prevail. 

Transgender Pressure Cooker

Image from Jeshoots.com. 

When someone writes or says something about me being a transgender woman being a choice, I have to laugh. 

I'm sure those of you who have gone through life the way I have with gender issues would agree. Primarily because we have given up so much to cross the gender frontier. Primarily, I am referring to losing family, spouses, employment and gender privileges to transition. Just losing male privileges alone is a major issue. Very quickly I discovered I lost a portion of my intelligence when by accident I became involved in a conversation with several men. I found I was not respected in their world until I finally got tired of being ignored and left the group. Then I began to not speak much until I was spoken to until I began to gain more confidence. 

When I began to be successful, the pressure to be even better as a transgender woman started to increase. For several reasons, my fragile mental health became worse as I started to try to live a life situated between the two main primary genders. In other words, I was stuck in a gender fluid universe I did not want to be in. Living one day as a man and the next as a transgender woman, nearly killed me.  It became so bad I needed to make a conscious effort daily determining what gender I was going to be that day. How was I walking and talking were just a few of the many gender considerations I was going through as the pressure kept increasing. 

All of a sudden, I was able to establish a whole new identity as a trans woman. I was talking to other women and building a small circle of friends which taught me so much about the world I so much wanted to be a part of. I kept going because the process became so natural to me and very soon the main source of pressure came from having to return to what was left of my male life. Even thinking about going back caused me stress and added pressure. 

Finally, I knew I had no way around it and never really had a choice with my life. As a gender therapist told me so many years ago, there ultimately would be no choice for me if I was a transgender woman. Sadly I did not believe her and stubbornly went on to fight a losing gender battle for years before I gave up and faced my gender reality. By doing so, I tried very self destructive measures including suicide and excessive alcohol abuse before I started to live my truth. 

I had no choice and needed to give up all the pressure I felt to transition into a feminine world before it all literally killed me. Thank goodness for all the friends and family I had who helped me through my difficult pressure packed days. The more good days I had with them led to my belief I could live my gender truth full time. Ultimately transitioning was similar to sliding down a hill towards a steep cliff for me. I had others around me who took the pressure off and made the landing a soft one.  

A Point of No Return

 

Image from the Jessie Hart
Archives.

For nearly a half a century I considered myself a more or less serious cross dresser or transvestite. In addition, I considered the transvestite label little more than just that, a label which was appropriate just to  use around others. Even though I rarely told anyone else about my gender issues.

The only people I can remember telling would number under ten before I finally came out into the world as a novice transgender woman. The first people I ever trusted enough to share my biggest secret oddly enough were friends I had in the Army. My disclosure came after I risked what was left of my time in the Army by dressing totally as a woman for a Halloween party.  Following the party, several weeks later under the influence of great German beer, the subject of the party came up. Of course then, the conversation went to what our costumes were. 

When the subject turned to me and how good I looked, I gathered the courage and told the three others the night was not the first time I had cross dressed as a woman and in fact I was a transvestite. I ended up taking a major leap of faith telling them because I still had approximately six or seven months to go on my enlistment and conceivably I could have encountered problems if the gender information I disclosed got into the wrong hands. After making it so far towards an honorable discharge, I certainly did not want to destroy the time I had put in. Plus, what would I tell my friends and family at home when I arrived back there early. 

To make a long story short, nothing negative happened with telling my friends I was in reality a transvestite and the experience was very liberating. On the other hand, I was not going to tell the rest of the world my secret. Of importance is the fact one of the people I told that night turned out to be the mother of my child and future wife. So I did not have to worry about telling her once we became married. I see her to this day and we still get along. Sadly, the other two friends I told are now deceased and I lost track of them almost completely before they passed. 

All of this brings me to the next person I told which was my Mom. It happened one night shortly after I was discharged and I was living at home for a very short while. One night when I came home from partying with my friends she was waiting up for me just like back in my college days. Somehow the conversation turned to my life and what I was up to. Out of the clear blue sky I decided to tell her my deepest secret about being a transvestite. I was still feeling liberated from telling my friends in the Army and felt secure in telling her, betting she would never tell my Dad. Just about the time I was feeling good about including Mom in my world, she turned around and roundly rejected me. All she really did was offer to pay for psychiatric care to solve the problem. Very quickly I rejected her offer and said no one was going to, in essence, plug me into a socket for electro-shock therapy.  From then on until she died, the subject of my growing gender dysphoria was never brought up again. 

The last person I came out to when I was still in my gender closet was my second wife. I write extensively concerning our gender battles but the fact remains she supported me as a cross dresser until I began my transition into a transgender woman. In essence, over the span of our twenty five year marriage, we just grew apart until her untimely death. 

Once I reached the point of no return in my male to female gender transition. there was no point in worrying about telling anyone I was transgender. It was obvious to the public who interacted with me what I was and they were left to draw their own conclusion. All of a sudden, all the pressure was off of me. All I needed to do was to do my best to present to the public who I really was. Plus, I would be remiss if I did not mention the roles gender affirming hormones played in my experiences. I was so happy with the results I was experiencing, I never wanted to go back to a testosterone filled life. For once, a plan came together for me and the point of no return never had to be challenged. 

Close Encounters of the Transgender Kind

 

Image from the 
Jessie Hart Archives.

Very early in my life, similar to so many of you, I suffered many close calls when it came to being caught in my feminine clothes by my younger brother or worse yet my parents. 

As with most inquisitive younger brothers, if I was out of his sight for any length of time, he wondered what exactly was going on. To make matters worse, we were just a couple of grades apart at the same school, so we rode the same bus home and arrived at the same time. Leaving me very little time to cross dress and admire myself. I even had to hide out in the woods when the weather was good to dress up.

My parents were partially a different story. My Dad was a banker and Mom was a high school teacher, so they arrived home usually in time to sit down to dinner. If you remember those days. My point being, seemingly for weeks at a time I couldn't find a way to explore my gender closet at all and the pressure to do it just increased to the point of no return. Which meant I needed to take risks. We had two bathrooms in our house and sometimes I could barricade myself into the one which contained most of my Mom's makeup. When I combined her makeup with mine, I had plenty to experiment with. 

On the exceedingly rare days I was left all alone, I went all out. Even to the point of being able somehow to get away with shaving my legs. I was completely in love with how wonderful the air felt on my freshly shaven legs when I took the chance to walk to the mailbox which was some distance away. No matter how good I thought I looked, the biggest problem I had was with my hair. In those days, I was stuck with either the ultra short burr haircut my Dad had or the equally as bad crew cut. A wig of any kind to me in those days just seemed like the impossible dream and it wasn't until my college years when I could afford to buy a nice wig I cherished for years. I even hid it, as well as other cross dressing necessities away when I went away to the Army. Hoping they would not be discovered. They weren't. 

Even with all my precautions, I still ran into the times when I had to hurriedly wipe the makeup off my face and change my clothes when my parents came home early. I don't know how but I somehow survived without a gender confrontation which would have been a disaster. At the time, I thought when I became older I would have more control over my cross dressing desires and life would be better. In no way did I feel as if all of the sudden I would wake up with no gender dysphoria and life would be much better. On the other hand I still felt I would not have to hide my true self to others. To compensate, I developed a very macho exterior self and avoided making very many friends who I may have to come out to later. A process I would come to regret later in life.

It turned out, mainly because of my wanting to not come fully out as a transgender woman, hiding away my true self from a loved one would reach new heights of desperation. The loved one I am referring to is my second wife who knew from the beginning of our relationship I was a cross dresser and accepted it. Everything in our relationship was good until I finally faced the truth of me being transgender, which my wife soundly rejected. Increasingly, when she was working nights, I was out exploring the world as a trans woman to primarily see if I could make it or not. When I found I could, I began to go out more and more which led me to having more chances of being caught. All of which led to huge fights when I came home as my feminine self and she was waiting for me. It was like I was a kid again and resented the process completely but it was like a train wreck waiting to happen.

Our relationship became so strained, my wife told me things like why didn't I just man up and live as a woman. A great point which I never did while she was alive. Somehow, it was similar to me trying a last gasp attempt at saving what was left of my manhood at her expense.

When she did unexpectedly pass from a massive heart attack, at the age of sixty, I finally was able not to worry about any close gender encounters. I had paid my dues and was so happy to fully come through an often very uncertain life and live in the world as a fulltime transgender woman with no negative people in tow. A dream I thought I could never achieve.   

Gender Euphoria

Image from Mohammed Nohassi 
on UnSplash.

During my circle of life which I am fortunate to still be living, there have been tines of intense gender euphoria. Those times seemed on occasion to correspond with  my severe bouts of gender dysphoria. 

Examples of euphoria came when I gathered the courage during a cross dresser-transvestite mixer I attended to have my makeup applied by a professional makeup person. He ended up working miracles on my face and I looked great (in my humble opinion) which was to be proven later that evening. What happened was I ended up tagging along with the "A" list cross dressers or transgender women in the group who always continued the party at an outside venue after the main mixer closed down. The first venue we went to was a large gay and lesbian dance club which I never really liked but I went anyhow. 

During the evening, the group broke up even further and we went to a much smaller venue which I couldn't tell was gay or not. All I knew was I enjoyed the music better and the place had pinball games I could entertain myself with. In a case of timing wasn't everything, about the time the remaining "A" listers wanted to call a cab and leave, I was approached by a handsome man who wanted to buy me a drink and play pinball. It turned out to be one of the pivotal moments of my cross dressing life when I politely declined his invitation and left. I was then forever caught wondering what would have happened if I would have stayed. Primarily I didn't because I would have been stuck in a strange city which I had very little knowledge of with a man I didn't know. On the positive side, I was the only one in the group who was approached by any other patron at all. In that moment my gender euphoria reached one of it's peaks. Perhaps the best part of the experience were the advanced makeup tricks I was able to understand and remember later. 

Of course there were other moments of intense euphoria such as the night I needed to show my male drivers license to be admitted to another transvestite mixer I went to. The greeters at the door thought I just had to be a cis-gender woman. Sadly, with every success I had with these cross dressing experiments, there were the downsides also. Mainly because of my ego which still in many ways was dictated by my old male self. For lack of a better example, every up comes with a down and when I crashed over a gender euphoric high, I was not an easy person to live with. To make matters worse, my crash was so bad, I couldn't keep my mind on anything other than the next time I could cross dress and go out as my feminine self. None of which my second wife approved of. Looking back, I don't see now how our twenty five year relationship survived. 

Regardless of these few and far between gender euphoric moments, I can safely say gender dysphoria ruled my life. Starting with the days when I was a kid wondering if I was a boy or a girl and continuing into and with daily combat with my mirror. Again and again I suffered the gender torment of seeing feminine in the mirror one moment and masculine the next. It was during my darkest moments when I found I could indeed lead a life as a transgender woman that got me by in life, barely. 

By the time I had reached my sixties and had started HRT, I knew I would never have wished my life's journey on anyone else. Going behind the gender curtain and learning life from both sides of the binary gender spectrum had certainly taken a toll on me. On the other hand, the experiences I went through taught me to be a better human being. 

Balancing gender euphoria with massive gender dysphoria in life can be a daunting task and one which should not be taken lightly as it can effect a person's overall mental health. Gender is one of the deepest emotional issues a human can have. It can never be taken for granted it seems with a transgender woman or trans man, unlike a large portion of the rest of the population. Which could be a topic for a future blog post.