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I played a chick in EQ because people gave me free (really good) stuff and money just in hopes that I really was a woman and that I would be their friend.

In FFXI I played a chick but that's only because I wanted to be a Mithra (Manthra FTW!). What was scary about that game was that you would get crazy stalker people that wouldn't leave you alone even after you told them you were a dude.