I actually did one year. I don't think I make a very good looking woman but my GF and her friends at the time said they would make me a knockout. After two hours of makeup and dressing I say I was kind of hot. It was still obvious I was a man and my GF dressed as a man so we were quite the attraction at the bar. This was the early 90s in the Midwest so if it wasn't Halloween it wouldn't have been accepted as easily. There were a couple guys that through conversation heard I was bi and asked if I would suck cock dressed like this. I was able to suck one guy in the bathroom. The GF was a little upset cause she wanted to find a guy that we could both play with that night.
We did end up with one guy back at his hotel and had a great 3 some.
I want so badly to get all dressed up and go out to the bars or to a Halloween party! It would be my first time going out in public dressed. I just need to find someone to go out with!
My First Halloween costume was prior to myself being a teenager, and it was an Alice in Wonderland outfit. I really enjoyed being a girl that evening, When I returned home, mom asked "well my son, or one should address you as my daughter?" How did you enjoy being Alice tonight? Oh mom, I just loved it and wished I was a girl. Since that October 31; mom began to dress me as a girl and have me wear a nightdress in bed. Now mom named me Jane.
