I have this friend who is a crossdresser in a very loose sense of the word. He really just wears pantyhose and has a fetish for pantyhose. He's never been totally dressed, the closest was last Halloween, he wore a skirt and heels but was otherwise in male mode.
Recently, he has joined a local community of pick up artists who, if you're not familiar with them, are men who make a lifestyle and living from picking up on women. Today he showed me a picture of his Halloween costume, a skimpy, sexy nun outfit that he intends to wear with pantyhose and heels.
On Halloween, he wants to hit the scene in his sexy nun outfit and pick up on women. I have to admit, I am completely intrigued by this and would love to be a fly on the wall as he attempts this. He can get away with it on Halloween but it made me wonder about something else.
Has anyone tried to pick up on women while dressed? I mean it's one thing to talk to a stranger you find attractive in regular guy mode but doing it dressed is entirely different. At least you have that part about you out of the way right? You don't have to break it to her later, no more secrets.
Has anyone successfully approached someone they found attractive while dressed or ever went out with or dated someone they met while dressed? Better yet, would you ever approach or pick up on someone while dressed?