Friday, October 31, 2025

Halloween and Me

Image from Nice M
Nsshti on UnSplash.

Even though it has been years since I have been to a Halloween party at all, it still fills a special place in my heart.

The main reason it will is because it was the first time in my life that I was able to really explore if I could possibly make it to my dream of ever living like a woman on my own terms. In the recent past, I have written about the very first parties I went to dressed as a slutty, trashy woman, attempting in my own backwards way to be sexy. Also, when I started to go to Halloween dressed as me, I was doing it around people who knew me as a man, so I needed to put up with the idea in their mind that I was some sort of a jokester. When of course I was dead serious. One memorable evening took me to the freshly restored Ohio Theatre in downtown Columbus, Ohio for a midnight Halloween showing of the original “Dracula” movie, complete with background music from the original theatre organ. I went with my first wife who already knew I was a cross dresser and two other friends. I ended up having a fabulous time in my heels, hose and minidress surrounded by many other attendees in costume. The only problem I had was walking as long as I did in my heels. I was still too new to the cross-dressing style game to think ahead about my footwear if I needed to walk very far.

As the years and Halloween’s moved by, my whole focus began to shift about my potential “costume” I was planning on wearing. I began to move away from the trashy costumes I wore in the past, and into “costume” ideas another ciswoman would wear. At the same time, I stopped going to parties with my friends and began going to big clubs where I could see if I could blend in. It all was working out well until one night I was stopped by a guy wearing a full mask telling me he knew who I was. I was in shock and asked him how he knew, and he told me I looked like my mom. It turned out he grew up with me down the road and knew both of my parents. I was relieved as I was proud of my “French Girl Costume.” Which meant I was dressed all in black. Including a new pair of black tights, flats, blond hair and a black beret I purchased for a dollar at a thrift store. Other than being rudely recognized, I had another great time, and the evening ended too soon.

A few of my final Halloween parties I went to proved to me that I could possibly make it in the world as a transfeminine person. One was by pure accident and one I had planned ahead for. The pure accidental party was the one I recently wrote about which happened when I lived in the New York City metro area. Out of nowhere, I was invited by one of my female managers to a Halloween party her and her friends were going to at a nearby tavern, to her house. I don’t know why, but I decided to back slide in my “costume” idea and go to the party dressed a little on the slutty side. Mini skirt, heels, blond wig and all. It turned out all of her friends who were going were approximately as tall as I was and were all dressed to thrill also. What a surprise I had when I found I could blend in with all of them. The only problem I had was my second wife not approving of my “costume” even though she did not want to go. Life around the house was a bit frosty for a while.

The last major Halloween party I went to was a planned affair. I was invited to a party at a vintage restored Victorian mansion, along with a news girl who I worked with at the local radio station.  I was married to my first wife then and she did not care who I went with, so I planned to go as a professional woman just getting off of work. Just to see if I could. I did with a couple a write about often who thought I was a woman and were so entranced with me, they invited me to another party they were going to. I did not go but stayed and had a great time at a fabulous party.

Sadly, all my fun went away when I fully transitioned into being a transgender woman. Instead of putting on some sort of “costume” and going out into the world, I was just being me, and an exciting part of my life was behind me. Forever to be remembered fondly in my mind.

 

 

 

  


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Halloween and Me

Image from Nice M Nsshti on UnSplash. Even though it has been years since I have been to a Halloween party at all, it still fills a special ...