Sunday, October 29, 2023

Ode to Halloween


Halloween image from
the Jessie Hart Archive (Tom on

I have lived long enough to experience Halloween coming full circle.

Early in life I experienced the urge to wear a feminine costume but never had the courage to break out of my gender closet and do it. Plus I lived in such a small rural area, there weren't too many kids to go around and once you were pigeon holed into a certain category with your peer group you couldn't get out.  Examples included friends who were good or bad students as well as those who were always the outstanding athletes in the class. There was never any space for a stray boy who wanted to be a girl.

So I had a deeper reason never, ever express my feminine longings at all on Halloween. On top of all of that, I never saw any other boys who were dressed as girls. No cheerleaders, princesses or any of the stereotypes from the female world. The only time I can remember ever seeing a fellow male in drag or cross dressed was for selected festivals in high school. I was amazed at their male to female transformation. Plus I did hear the gossip concerning another guy in school I didn't really know who was dressed in his sister's clothes for his "costume" as the rumor went. I was so envious!

Once the years progressed and I naturally achieved more freedom to be my own person, I was able to pursue more courageous goals as far as Halloween went. I tentatively used the holiday to sneak out of my closet and explore. Could I dare make it in public as my feminine self. Very early I learned lessons I could take with me for years as I transitioned. I found if I dressed more conservatively at Halloween I indeed could have a chance to present well in the public's eye as a woman. As it turned out, all of this would be just the beginning of what I could learn on my ever rocky gender journey. 

Halloween made it possible for me to understand I could indeed live a life as my authentic feminine self. The only real problem came when I could only experience my terrifying yet exciting new life once a year. I was increasingly forced into the real world to learn my new gender lessons. All of which were made possible by Halloween.

Ironically, the more I learned from my initial experiences, the more I found the lessons would serve me well when I transitioned into a world ran primarily by women. If I could get other women to accept me, the better and easier I would have it. I also learned the hard way the process I would need to go through with men to attempt acceptance. Along the way, when I learned the better I presented at Halloween parties as a woman, the more of my male privileges were lost. Almost instantly, my old male friends began to leave me alone with the rest of the women. 

These days I have gone full circle with Halloween. It has served it's purpose of launching my journey down a path to be a full time transgender woman. So I don't have any need to go to any parties with elaborate costumes. I have done all of that and it is time to sit back and recognize Halloween for all the amazing experiences I was provided.

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