Halloween Dreams

It amazes me after all these years I can still have so many vivid memories of my early Halloween experiences.

One of the earliest goes back to the 1980’s when I lived near Yonkers, New York. I was working for a Wendy’s franchisee then and one of my assistant managers invited me to a Halloween get together she was having. I saw it as the perfect opportunity to get out and live as a woman for a short period of time…if I could figure out how to do it. 

Since my wife wasn’t really into Halloween and knew why I was, it was fairly easy to convince her not to go. Plus, she was always against what she thought were my sleezy costumes. With her out of the way, I was free to costume myself anyway I pleased.

I picked out a short mini dress, heels and one of my fave wigs for the evening. If you remember, big hair was “in” in the 80’s, so I fit right in. After freshly shaving my legs, applying my makeup, panty hose and getting dressed, it was time to go.

What I wasn’t prepared for was how well I was going to fit right in. 

It turned out, the Halloween “party” she invited me to was actually a group of her girl friends who all were going to one of their local taverns to party. I was in heaven when I saw all these women dressed almost like I was. Initially they were in shock when they saw me and looked me over head to toe until my friend told them who I was. Then I was accepted. 

The tavern was within walking distance of her house, so here we were all in our heels clicking along as we walked to the party. Again, I blended right in and felt great. 

Once we arrived at the tavern, we proceeded to order drinks and the other women got up to dance. Unfortunately I have exactly no rhythm and kept my seat. Inwardly though, I was savoring every moment and even got asked to dance. Again, I politely declined. 

All too quickly the evening had to end and I had to head back to my routine existence. However, the word spread through out my store how I had dressed for Halloween. Nothing much happened as I just said I always wanted to do it. Resulting in a few “yeah right” smiles.

Little did I know how long the memories of the evening would linger. It showed me how it would be to interact with women on their own level. If only for one evening.