What I Really Learned at Halloween

Kenny Eliason image from UnSplash.

 Sadly, since I have lived over ten years as a full-time transgender woman, Halloween has become just another day to pass out candy to any kids who may come by the house. The neighborhood is becoming older and we don't have the influx of kids we used to have years ago.

Regardless, I still have fond memories of when I went all out for Halloween. I used the experience as a testing ground to see if I could actually go out into the world as a woman and live. Throughout the month, I have focused on several Halloween adventures I had. When I first started, I thought dressing sexy would validate myself as a woman. Then I started to tone down my "costumes" all the way to going to the last party I remember dressed in feminine business casual attire which I was used to presenting in the upscale malls I was going to. 

The party itself was sort of a who's who of invitees held at a real live Victorian mansion in a restoration district in the town I lived in. I received my invitation because I was a fairly well known radio disc jockey in town at the time and happened to know the couple putting on the party. I knew immediately what I wanted to wear and just needed to decide who I wanted to invite to come with me. I knew my first wife was not into Halloween and wouldn't care if I invited someone else to go with me, so I invited the news-woman where I worked to go instead. An example of how easy going my wife really was. I always thought if I told her I was leaving for a month for gender realignment surgery, it would be fine with her. So the stage was set to be out and about as my authentic self. No playing around with a "costume", I wanted to be mistaken for the real deal.

Since there are no pictures from the party, my outfit consisted of a business suit, heels and blond shoulder length wig. Needless to say, my wife was not surprised but my date was completely. Mainly because of my shaved legs and how well I walked in the heels. When we arrived, thankfully, parking spots were not a problem and at the door, a coffin with a real skeleton greeted us . The mansion was really decorated well and we found a seat. 

Predictably, as the night went by, no one knew who I was and I blended in as a woman who arrived late from work and did not have a chance to find a costume. I was having a great time, when another couple came up and said how impressed they were with the way I looked and they thought I was a woman. Furthermore they were leaving soon to go to another party and wanted to know if we or I wanted to go along. Even though I was extremely flattered I turned them down but not before I found out who they were. The couple was a young congressman and his wife, leaving very soon to go back to Washington, DC. So I guess I destroyed any chance I had at a political career. 

What I really learned that Halloween was I could step out into the world as my authentic feminine self and survive. Very much worth all the time and effort I had put into to being a girl over the years. And, as far as the news-woman went, she never said a word.  

I guess you can say with out a doubt although the thrill is gone for my Halloween, the day more than any other one in my life served a wonderful need when I did not have any other outlet.

Set Her Free

Image from JJ Hart

Throughout my long life, which included fifty years of being a cross dresser, I could feel the stress and tension of not freeing my inner girl.

It all started innocently enough with trips in front of our family mirror in clothes I had borrowed from my Mom. Of course that all ended when I outgrew her sizes and I needed to strike out on my own to find fashion which fit. With my meager allowance and money I made from delivering newspapers to the neighborhood, I managed to get by and buy a few items to add to my wardrobe which then I needed to carefully hide away from my family.  Somehow I survived and my life as a male set in, no matter how much I did not want it to. 

The gender stress and tension continued over the years and even became worse with every success I had when I tried to set my inner self free. It finally became evident my entire gender life was backwards, I was not a man cross dressing as a woman, I was a woman cross dressing as a man and it was no wonder I was feeling the confusion and pain. I would not have wished the mental anguish I felt on my worst enemy. I found being transgender was far from being a choice and somehow I needed to set her free.

The problem was, I needed to face the same set of hurdles transgender women and trans men face. Such as family or spouses, friends and occupations. The longer you go in life, the more gender baggage you acquire, the more you have to get rid of. Or figure out how much you can keep. My prime example always is how I was able to maintain my love of sports when I fully transitioned into transgender womanhood. I had help when I learned the women around me loved sports as much as I did and I felt right at home. It was easier to set my woman free. 

Finally, I arrived at the point where I could take it no longer. I ended up living more time as a trans woman than I did as my old male self. So much so, I was feeling totally out of place in a male world as a guy and would have rather attacked it as a woman. Plus I still had the age old problems of doing my best appearance wise as a feminine person. I began by losing nearly fifty pounds and taking better care of my skin on a daily basis and worked my way forward from there. Through days of trial and error, I was able to arrive at a point where I could provide a reasonable attempt at presenting as myself on a regular basis. The key was to settle in to what myself should look like which meant stopping doing things such as switching wigs on a regular basis. Finding who I was proved to be the key to setting myself free.

Once I did manage to set my dominant self free, she did all the rest. I learned to keep my old male self out of the way and let her go. Among other things, she picked my friends and lover and opened the door to a life I never thought possible.

It was like she was saying I told you so and should have done it sooner. 

Fall Leaves

Image from Alisa Anton
on UnSplash. 

I write substantially how fall is my favorite season of the year. I love the cooler temperatures, wardrobe changes and how the trees change into their brilliant colors. All before the colors go away and drab winter sets in.

Long ago, I felt all the seasonal changes deep down to my inner soul. Of course as a novice transgender woman the wardrobe fashion changes were challenging and fun. I learned I needed to look ahead for the best clothing bargains if I was to be successful in locating all the fashion firsts in sizes that fit me. After a few seasonal changes, I began to feel so natural, I automatically felt the changes coming on. Fall was especially fun when it was time to go through all of my leggings, boots and sweaters to see what I would have to add or subtract to make it through another season.

Even though fashion changes were exciting and fun, other aspects of the season just brought about melancholy depression. I vividly remember the nights when I went out and just drove around in my car watching all the leaves blow around in the headlights. Here I was still stuck in a gender I did not want to have anything to do with and not seeing a way out. Very soon, the fun of fall would turn into the depression of winter for me. My final fall before leaving for Army basic training was especially bad because I knew for a fact I would not be able to do anything about my transgender desires for a very long three years of my life. It seemed so unfair my new life into transgender womanhood would have to be put on hold through no fault of my own. I was bitter. 

Little did I know, after waiting over two years out of three in the Army, karma would come back to help me. During my last year I learned of a Halloween party which was being planned by a hospital group which my friends and I were invited to. Immediately my mind jumped to the possibility of me dressing up as a woman and going. Of course the problem arose how was I going to do it because I did not want to go halfway. I wanted to be the sexiest dressed woman at the party. Fortunately, I had access to an apartment where I could finally shave my legs and put on makeup with a wig I managed to buy at a downtown Stuttgart, Germany shop where I was stationed. Through it all, I knew I was risking harassment or worse by my superiors in the Army if the word got out about my so called "costume" which may have been a little too good. But nothing ever happened.

In fact, because of the Halloween party, my life changed nearly full circle that fall. A couple of days after the party, when my closest friends gathered once again over potent, tasty German beer I blurted out the costume I wore was more than a casual fun idea I came up with on the spur of the moment. I was a transvestite as we were known back in those days and I enjoyed wearing women's clothes, makeup and wigs. I knew at the time, again I would be risking what was left of the time I had left in the Army if what I said found it's way into the wrong hands. It did not matter at the time as the first time I left my gender closet felt so good. So good, I tried to come out to my Mom who promptly slammed me back into my closet. 

All of this happened during the fall which still remains my favorite season of the year. As a  transgender woman, I appreciate the re-birth of spring but summer is too hot and winter is too long and drab. It's why fall leaves are so important to me.