Showing posts with label transvetite. Show all posts
Showing posts with label transvetite. Show all posts

Monday, October 20, 2025

It's Halloween Season

 

Image from Andrea Li
on UnSplash.

It is finally here, the season that all cross dressers and novice transgender women dream about, Halloween. It is the magical day when we can be ourselves without all the paranoia of being caught and exposed as a man wanting to be feminine. The time when everyone has a chance to cross the gender line and be themselves.

These days, since I sadly don’t participate in Halloween much anymore, I don’t write much about it. But back in the day, I was fanatical in my Halloween preparations. Without fail, I would begin thinking of my “costume” the first of October and change my mind several times before Halloween itself. I always felt a transgender woman had the right to change her mind. Would I try to be sexy this year or try for a more authentic “costume” such as a professional woman look. Major decisions I needed to make with the added pressure of knowing it would be another year before I could take advantage of the parties again.

Ironically, the “costumes” I chose followed in many ways my progression as an early transgender woman. In the early days, I would try to dress sexy and get away with the shortest mini dresses and highest heels I could find. Of course, then, I would give myself away as more than just a casual “jokester” at Halloween by shaving my legs, wearing a long sexy wig, and having great looking makeup. Which my wife took credit for when she wasn’t and didn’t wear any makeup at all. Even the most casual ciswoman observers at the parties I went to could tell how serious I was about looking my best as a woman.

As I said, I quickly grew out of my sexy/trashy Halloween costumes and began to dream of being accepted my mistake as a “real woman” at the parties I went to. That began my era of actually being mistaken for a woman just getting off work and coming to one of the parties I went to. I was professionally dressed in a dress and heels and ended up surprising other guests I had known for years. For the evening, I went with another woman other than my wife and had to sadly turn down a request to go with another couple to a different party. Later on, I learned that the man was a politician who was elected to Washington, so my political career was quickly ended by saying no.

Outside of that party, there was only one other party I went to when I was dressed in a moderately sexy “costume”. It was during my stay in New York and another night I got out of the house without my second wife going with me, for some reason. This time, my invitation came from one of my female managers where I worked, so I looked forward to what the evening had in store for me. It turned out my sexy “costume” hair and makeup fit it perfectly with the other women I ended up meeting for the first time.

I ended up meeting everyone in my manager’s house and they were all there when I arrived. I will never forget the delight I felt when I saw they were all dressed like me, so unknowingly I had dressed to blend with them. Also, I will never forget the hush that fell over the room as the other women looked me over from head to toe. I ended up tagging along in my heels, hose and mini skirt with all the other women who were almost as tall as I when we made our way to a close by neighborhood bar where the party was taking place. I had my misgivings about how I would be treated there, but after I was in the bar for a while, there was no indication from anyone that I was not anyone different than I appeared. I was even asked if I wanted to dance by a man. All I know was the night flew by in a hurry and my wife did not speak to me for days because she saw my “costume” before I left.

Even though my Halloween highs were very high, sadly they were accompanied by very lows I needed to suffer through. I became very depressed and mean and tried to make everyone around me feel the same way. My problem was only ultimately solved by getting out of my dark gender closet more than just once a year.

In order for me to exist in a life I was discovering I needed, I had to set Halloween aside as just another day. Which ultimately took all the fun and drama away from it. But sacrifices had to be made for me to live as a transgender woman and Halloween was just one of them.

 

It's Halloween Season

  Image from Andrea Li on UnSplash. It is finally here, the season that all cross dressers and novice transgender women dream about, Hallow...