Cuz every girl's crazy bout a crossdressed man
A few years ago a week before that snowy Halloween in the Northeastern US I thought I was caught by my roommate when he came home early. I was not. To try to save my in closet hobby I decided to go in drag for Halloween. That Saturday I needed to go out to the mall to pick up a few things to complete my outfit I needed to find a waist cincher and some hip and butt padding. I was worried about walking in heels up until then I only walked in them for a few feet here and there in my apartment I knew I would be spending all night walking in them in the city. I decided to wear the heels out to the mall to get practice. After little bit of psyching up in the car I crossed the Rubicon and walked to the mall in my 6 inch heels. No one noticed. I got to the lingerie store to find my last-minute items only to find nothing in my size.
As I was waiting at the counter to ask a SA a question the young woman ahead of me noticed my shoes and began a conversation with me. She seemed very impressed when I told her what I was doing and within less than a minute of meeting me asked me to go to her Halloween party. This was new for me I'm not usually the type of guy who attracts female attention at least not that quickly. But alas I had plans with my friends that night and I could not have gone to her party. My next stop was a beauty salon that did makeup and nails. I made an appointment earlier that week so they were ready for me. All the women in the salon came over to the watch or give me compliments as I got my nails done and they all needed a picture with me once the makeup and wig were on. Once my friends saw me they were completely surprised and that is when I found out that I was in no way caught earlier that week. We made it to the parking lot in the city and met the female half of our group. They were all completely surprised by my costume some thought I was an actual woman from afar. The girls walked and talked with me as we headed towards the bar and they sympathized and were impressed with how I walked in those heels.
At the bar I got out onto the dance floor with much less prodding than normal. I dance with the girls from our group and some girls from other groups. One woman dance with me a little bit more than the others and we had that awkward getting to know each other chat whilel shouting at each other across the music and noise of a crowded bar on a Halloween night. She very much like my costume and she said she enjoyed dancing with me throughout the night but unfortunately she was a bartender at another bar and had to go on shift. I ended up meeting a guy she knew, a regular, who told me that she really like me and that if she had not had to go on her shift she was going to ask me back to her place. Again I am not used to being the object of such quick female attraction. This guy also told me that he has a friend that lived in Miami and he goes out in drag every Halloween because it attracts women a lot.
Now as a cross dresser the default thought is almost always that cross-dressing repels women. But this was Halloween and if it is seen that your cross-dressing as a costume rather than an all year-round hobby the man who cross dresses is look at in a much different light. A cross-dresser is probably seen as bold and confident because that's what it takes for a man to wear women's clothing in public. There is probably some empathy going on such as the shared torture of walking in high heels. I don't know but I do think the confidense angle has a lot to do with it. Once I made the decision to go out that night in drag and pass that first hurdle there was nothing that night that would scare me.
