Welcome to Hell

Inside "Casa Susanna" A dream trip I never made. 

My early days of dealing with a severe case of gender dysphoria can only be described as being in hell.

For those of you who can remember the dark days of information before the internet and social media, you also recall the days of being completely alone in your dark gender closet. Since I was raised in a very male dominated family, I knew escaping my own closet was going to be difficult at it's best. I was forced to sneak around behind my family's back to steal away the time to cross dress in my small stash of girls clothes and makeup. I even resorted to storing away my clothes and a spare mirror in plastic bags in a hollowed out tree in the woods next to our house.

Through it all, I knew the whole process of dressing as a girl made me feel better but somehow would have to be enough to get me by. I followed the vicious cycles of feeling the gender euphoria of being feminine in my mirror with deep depression when I was denied access to my clothes. I learned very early I wanted to do more than look feminine, I wanted to be feminine. Way before the term transgender was ever invented. to put the date in perspective, I would have been in the 1960's before I hit my teenaged years and still years away from my military duty and discovering Virginia Prince and her "Transvestia" publication which only dealt with so called heterosexual cross dressers or transvestites. I mention "Tranvestia" again because it was my first link to other like minded people. 

From then on, I knew I wasn't alone and could even go to transvestite mixers which were within driving distance of me. Even though I had discovered others, it turned out I was still dealing with my own personal hell. I still needed to be able to deal with the gender euphoric times followed by longer periods of gender dysphoric down times. Ironically I brought much of my hell on myself by not knowing the best ways to dress and apply makeup to best present my inner female to the public world. I had a difficult time dealing with all the stares, all the way to laughter when I tried to take on the world. Once I began to learn how to best handle the public, along came the Army to disrupt my life. As much as I didn't really want to experience military life at all, specifically I didn't know how I could exist three long years without having a chance to express my feminine self. For years, as I waited for the Vietnam War to draft me, I went through hell considering it's ramifications to me.

One way or another, I made it through the three years and couldn't wait for the relative freedom I had to escape my own personal gender hell, no matter how briefly. 

My big escape came when I made the highly personal decision to stop considering myself a cross dresser when I went out and I transitioned into thinking of myself as a transgender woman. Semantics to be sure but a huge move for me mentally. By mentally transitioning I was able to take a huge step out of my own personal gender hell. In many ways, I entered my golden years of MtF gender transition by leaving much of my hell behind and be able to increasingly explore the world. 

From then on I was able to free myself from my gender dysphoric hell and start to live my dream life as a transgender woman. Although I want to say the process was worth it, I wouldn't wish my journey on my worst enemy.

Coming Out to Employees?

 

Halloween Witches Ball Image
Liz on Right 

As we rapidly approach Halloween and my wife Liz's operation coming up, I thought it was time  for another Halloween experience while I still had time. 

This one happened when I was managing a fast food restaurant just outside of the New York City  metro area. More precisely, very close to the Bronx. As Halloween rolled around, once again  I was stressing out about what I was going to wear. The pressure was on since it was nearly impossible for me to leave the house we lived in dressed as my feminine self. I was back in the mode of waiting another year to escape from my mirror until the next Halloween rolled around.

As I faced the pressure head on, I decided to go all out as I decided what my "costume" was going to be. I put together what I thought would be a potentially a sexy look without crossing the line into being trashy. I pulled out my shortest dress, along with my highest heels. Most certainly, my wife's most hated outfit on me. In this case, I used her motivation of me to spur me on. For once, since she wasn't going anyhow, I decided she would have to get over it. I would have to put up with her displeasure with me for the next several weeks but it was worth it for me to pursue my dreams.

As I said, my outfit was going to be short and sexy as I to the best of my ability fool the world to what my true gender was all about. Little did I know, I would be able to find a situation where I was able to blend right in. 

As it turned out, one of my assistant (woman) managers was going out to one of her local taverns to celebrate Halloween with her friends and she invited me along. After I dressed, did my makeup and hair and was ready to go. When I arrived at my manager's house, it turned out the friends she was going with turned out to all be tall and beautiful . As it turned out, by pure accident, At least in the height department., I fit right in. When I first saw all of them, as the room grew silent, you could have heard a pin drop. Time seemed to stop for me as they examined me from head to toe. Of course I could only guess what they were thinking as we left for the short walk to the venue where we were going. Thank goodness for me (in my heels) it was not a long walk.

As we arrived, I learned a valuable lesson about being with other single women who were attractive. The first thing the women did was essentially split and worked the room. They left me on my own which was an experience in itself. After I bought a drink and found a seat at a small table, I settled in to try to enjoy my evening in the world as a novice transgender woman or even a transvestite. And it turned out, the night was far from over. As I tried to sit by myself, I attracted attention from an older guy who kept bugging me to dance. Which I refused although deep down I was flattered. Finally, the night was over, the group of women broke up and headed their own ways. 

I ended up back at my restaurant which I knew was closed by then. What I didn't count on was, the closing crew would just be getting done and they would see me in my "costume." Surprisingly to me, the response was positive even to the point of one of the guys saying I had good legs. 

More importantly, the backlash from me dressing as a woman for Halloween was a non starter for most of my crew and life went on. The only variable was my assistant manager who I think couldn't wait to tell my boss who smiled at me differently for awhile. However it was New York and there were bigger issues to deal with than me dressing as a woman for Halloween. Which was one of the reasons I wanted to move there from our native Ohio to begin with. 

As far as my second wife went, she finally made me pay my dues as only a woman knows how to do. I learned from it and moved on. Knowing I had been able to experience a truly wonderful evening to think about and remember forever. 

Pre-Political Meetup

Image from the 
Jessie Hart Archives...

 Long ago, following a few of my Halloween adventures when I did my best to stay away from looking trashy on Halloween. I was determined to do my best this night to be mistaken for a cis-woman. 

I decided to attend a party I was invited to as a professional business woman. The get-together was being held at a restored Victorian mansion which was owned by a casual friend I knew. A wide range of people were invited. I worked at a radio station in town at the time and since my first wife never really was into Halloween, I was left on my own to find someone else to accompany me. It turned out one of the news reporter women at the radio station had an invitation also, so we agreed to go together.

In no time at all, it was time to put together my "costume." I started with shaving my legs and putting on a brand new pair of panty hose. From there, it was very easy to choose an outfit from my growing feminine wardrobe. The years have clouded my memory so I do not exactly remember what I wore except it included heels and my red wig which I loved so much. Of course when my "date" saw me she was amazed and amused I would go to such lengths to be noticed on Halloween. Plus she was more than impressed when I was able to do such a good job walking in heels "for the first time." 

When we arrived, the hosts had done a wonderful job of decorating their old mansion. Even including a vintage glass topped coffin with a real skeleton. Most importantly, I was able to relax and enjoy being out of my gender closet for the first time in a year in public. I was truly a novice transgender woman just exploring the possibility for the first time if I could be accepted in the feminine world. 

As the night progressed, guests came and went and the alcohol flowed. Also I was receiving plenty of positive feedback on my "costume." I had made the correct choice to dress as a professional woman for the party. Most of the other guests assumed I was just arriving late from work and didn.t have a chance to dress up. Which was exactly my goal. 

The most flattering happening came when this couple approached me and said how impressed they were with my "look." They were totally fooled into thinking I was a woman. Through it all, I recognized the man and his wife as a newly elected politician on his way to Washington, DC. Plus they wanted me to tag along with them to another party they were going to,. Since I didn't know where they were going and was with someone else, I had to politely decline the invitation. Leaving me to forever wonder what would have happened if I had decided to go along with them. 

Who knows? Perhaps my political career was ended before it even had a chance to begin. At any rate, the evening turned out to be a blast and my "date" never mentioned how I looked again. It wasn't too long when she landed another news job and moved away anyhow. 

As far as the politician goes, he turned out to be re-elected several times to congress. I lost track of him also when his political career was over. I stayed friends with the owners of the mansion over the years until I moved away and they divorced. Maybe deep down inside I was disappointed no one brought up how I looked on Halloween that night so long ago. I was probably desperately trying to out myself and no one cared. Or I was so good at hiding my feminine side with my intense male self, no one could see my true self. 

It wasn't to be until years later, my feminine self finally took control and Halloween "costumes" became a thing of the past for me.