A Halloween Political Decision

Image from Nice M Nshuti
on UnSplash

This is the second in my month-long series of Halloween decisions I made during and after the parties I went to.

This party took place in a wonderfully restored Victorian Mansion in my hometown where I worked as a radio disc jockey. Just to get an invitation was impressive to me as I struggled to come up with a “costume” to wear. Ironically, by this time in my life I had almost went full circle in my choices of what I was going to wear. I had long since gone from my slutty/trashy woman look all the way to a more moderate less clownish woman with my “costume.” I could still try to be sexy without going overboard as most ciswomen around me were doing on Halloween.

I finally decided to go full circle and see if I could wear something so authentic that the normal party person would not recognize me as a guy at all. I thought it would be the ultimate chance to test how far I had come as a transgender woman in the world on a low risk-high reward Halloween evening. Once again, my wife did not want to go with me, so I ended up with the news girl at the radio station as my companion for the evening.

I discovered I was off to a good start as my companion for the evening marveled at my “costume.” I chose to be a professional woman, just getting off from work and coming to the party to test my newfound freedom in the world. For at least one night.

When we arrived and found a parking place, I loved how my heels clicked up the sidewalk as my “date asked me how long I had practiced in the heels to wear them as well as I did. I just told her longer than it took me to shave my legs and apply my own makeup, so she left me alone after that. As far as asking any further questions about my skills dressing as a woman. Fortunately, it was a beautiful warm evening for Ohio in October, so I did not have to worry about any sort of jacket, sweater or coat as we made our way up to the mansion’s front door. The whole house was beautifully decorated for Halloween, complete with a vintage wooden coffin complete with a real skeleton.

I was met at the door by the hosts for the evening who like my “date” marveled at my male to female transformation. With the good start I was having, I immediately started to relax in my new surroundings and enjoy looking at the other costumed visitors. I was just about ignored as I did manage to blend in as a professional woman until later in the evening when a couple arrived and started to talk to us. It was just after a little bit of conversation that they told me, they did not recognize me as a man at all, and my “costume” had worked. My mind was shooting fireworks of joy when they told me that and it even went on to new heights when they even asked me to leave with them and go to a different party.

By this time, I had recognized the couple who were very active in politics and was on their way to Washington due to a recent election victory. So at least I knew who I was dealing with and if it had been just up to me, I would have said yes and went to the other party with them. But it was not just up to me since I had driven and I needed to get my “date” back home, so I had to sadly make a split-second decision and say no. Either way, I was very flattered by the offer and who knows what I would have encountered as my feminine self at the other party. We stayed on at the original party for a while had a couple more drinks and headed back to the house where I needed to reluctantly return to my old male life for what I thought was going to be another year. Always maintaining the “what if” ideas if I had continued with the politician and his wife, Maybe I could have gone to Washington also.

Another good thing that happened with the Halloween party I went to was, it was the first time that I ever thought/proved I could make it in the world as my true feminine self. Plus, I knew I could not wait another year for Halloween to roll around for me to live as a novice transgender woman again. If I had made it one night as a professional woman in the world, there was no reason I could not do it again. I just had to take matters into my own hands and do something about my gender dysphoria which was helping to wreck my mental health.

The evening was also more proof I had done the right thing for a change when it came to testing the strength of my male to female femininization project. I found I was coming along faster than I thought and I could never go back to living the totally male life I had before I tested the gender waters at the Halloween parties I went to as a cross-dresser. It was as if I had found a giant search light on my gender path and suddenly, my life made more sense. It was so much deeper than anything I thought it could be.

That is why not going out with the politician and his wife maybe cost me a chance at more fun and even enlightenment about who I really was. But on the other hand, I did the right thing by my wife and my date if she did not want to go early and end my evening. I felt better about it in the years to come. Even though, I wonder what would have happened if I had made the other decision. Most likely nothing and the memories are better than the actual experience.

Another reason Halloween will forever occupy a special place in my soul and there were several other evenings I will try to pass along before the actual holiday. Thanks for reading along and commenting!