At work yesterday some of the women were talking about how unfair it is that so much women's clothing is uncomfortable to wear compared to men's clothing. I joked that it was not so hard really and they should stop complaining, and after a few laughs some of them suggested that if I thought it was so easy I should try it so they dared me. Our office has a halloween costume contest every year and they bet me that I would not dare to dress in drag for it when it comes around in October. They say they would give me a makeover and get me the clothes, the make up, wig, shoes, everything. I would be dressed in a business suit for work and a little black party dress for a party afterwards. I don't mind having a bit of fun and there are always good prizes in the contest, so do you think it is a good idea? Any advice?