 If you liked
Princess Princess
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 ...then you might like
Binan Koukou Chikyuu Bouei-bu LOVE!
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There is a group of guys who are forced to wear very "girly" outfits and say embarrassing things that you wouldn't expect to come out of a boy's mouth.
Although they protest at first, the boys are quick to accept their situations and act the part accordingly.
Both shows are very funny and weird, but you can't help but love them.
Both are set in an all boys' school and have really ridiculous plots. The main group of boys in each dress in girly clothing against their will (though they accept it anyway). The student council is pretty important in both as well (and Hiroshi Kamiya voices the student council president in both).
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Recommended by tearbender