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There are lots of great ideas. Easy is to just dress up as a girl. Marilyn Monroe is a good one. A girl scout or super hero. A devil. Or get a girl to be the opposite, I've always wanted to do bo...

I would dress however you want for Halloween. The best thing that could happen is that someone mentions that you dressed 10 years ago. Then you can reply, "I had a blast then and I am having a...

For your swim suit idea reminds me of a costume that a friend of mine came up with- "East German Swim team". It's a little dated, but it has all the crossdressing and humor combined. You don't even...

My wife wants to have a halloween party and even though she frowns on my crossdressing, she said that I could dress for halloween. I have decided not to dress as a girl this year, but I am trying to...

I think you should go and apply to be a waitress. I guess it would be easier if it was at a bar that specializes in drag shows, but there are plenty of bars and restaurants that would be happy to...

go shopping and pretend that you are shopping for yourself. when the sales girl comes around to help you tell your friend that shopping isn't as easy for a girl and hand him some clothes and tell...

So, I've been dressed for Halloween a few times. A Hooter's girl (I was dating one at the time), and a school girl. I've also gone out just dressed as a girl.

The best response on halloween...