I was dressed as a woman for the first time in my life during Halloween this year. Here is what happened, and what I thought about it.

Hello everyone. I had told a few people that I would write my thoughts on my first experience dressed up in womens clothing since I agreed to do it on Halloween. I figure that here is a good place to post it since some of those people come here.

I am a little bit (well alot) lazy sometimes, and I also have a bad habit of procrastinating. I also had a few Halloween parties to go to, and I was threatened with bodily harm if I showed up as a psychopathic serial killer who was trying to blend in (i.e., in my regular jeans and t-shirt) like I usually do. I never did get down to get a costume, so I let some women I know fix me up in a costume. I didn't know what they were planning until I had already agreed to do it.

The costume involved a long dark wig, a red formal dress, a horrible torture device called a corset, hose, and high heels, plus make up of course. They got all of it new too, but since one of them owns a wig shop, one works at a bridal shop, one sells shoes, and the other one is a beautician (who can also do theatrical makeup) it didn't cost them much at all.

I found out that pantyhose feel really weird. The corset was horrible since the girls decided I needed to go from my normal 34 inches in the waist to less than 30. The heels also felt really weird, and they affected the way I walk since I am used to tennis shoes. The wig was like having a snow hat on, and the bangs on it got in my eyes a few times. That was annoying. The dress was not as comfortable as my jeans and t-shirt are, plus it was so long that I almost tripped on it a few times going up and down stairs.

When they put the makeup on me I thought they were going to poke my eyes out a few times and so I had to really fight my instincts to do what they said so they could do a good job. It also felt like my face was covered with too much stuff. When I was told I couldn't touch my face I noticed I felt an itch start up where there was none before. The fingernail polish felt weird too.

This experience helps me to understand a friend I have who is transgendered a little better, but I still do not understand why someone would feel comfortable in all that stuff. I did have fun with it though, and I had more pictures taken of me that day than I have had taken in the past few years. Even complete strangers wanted their pictures taken with me when I went to the store and the gas station. I did win 70 dollars and a gift certificate to Appelbees, and I got a free haircut (the best one I have had in a long time) from the beautician though.

I think I looked weird, but others have told me I turned out pretty good. I still can't believe all the pictures that were taken, especially by people I didn't know. A few of them are up at the Gabyzone in my gallery. Well, that is the first time I have ever been dressed up as a woman in my life, and my thoughts about it.