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.