This is kind of a dangerous subject, since it's so open to ridicule, but we might as well allow for equal opportunity. Men playing female roles has been a long and honored tradition in European theater, and in Kabuki. The reverse also exists but not for as long, with the all-female cast of Takarazuka playing both the male and female roles. When it comes to maid cafes, the Dansou cafes have women dressing up as butlers, and there's also the "little brother" cafes with an all-female staff. Finally, okama bars, or transvestite bars, have been popular in Tokyo for a while as well.
The Japan times recently ran a story on Hibari-tei, an okama maid cafe.