The Email Request

As always there are a number of things I've been wanting to post about especially before I forget it all but for this post I thought I would just mention an email received at my work a few days ago which took me back to the old days reading about sissy stuff. If you're reading this I expect it's a route you may have gone down as well. Crossdressers look for any excuse to dress up and make it not look like it's exactly what we wanted to do. 

Anyway, this email came from a man who I'll call Billy (not his real name). Billy informed us that he had just lost a bet (haven't we all?) and now had to dress up as a woman and work at a local business for a few days (for nothing). We would get to pick his outfit and if we wanted him to attend an interview in drag then he would be willing. No idea what this mysterious bet was but good on him for trying it. Hell, if he's able to find a place you can work in drag I'm willing to try it out. 

Reading the email took me back to reading about crossdressers experiences go out and also the self challenges that people may do such as going into shops asking to try on wedding dresses or lingerie although I think to do that you may have a bit of a humiliation fetish. Certainly I've written enough caps in my time dealing with lost bets. I haven't passed on the email so I doubt I would be able to give poor Billy a chance although I just imagine if I did it would be the best day of his life.