 If you liked
Otome wa Boku ni Koishiteru
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 ...then you might like
Maria†Holic
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The main characters cross-dress into this all-girl school for the apparently same reason (which I will not reveal since some might consider this a sppoiler -.-''). Even though the genre of these series don't really match, there were a lot of things that were particularly similar. For example, there's a ''Mariya'' in both series o.O
Not only that, I feel that the story lacked something... in both series
Otome might be a bit more... shoujo than maria+holic, but they are mainly the same: it follows the life of several girls and one boy.
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Recommended by Otaku-yarou
They share a similar setting and gender bending theme. Both of them excellent anime.
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Recommended by ariolander
Maria+Holic's lead is essentially a parody of OtoBoku's main character. The premise that causes them to do what they do is similar, but minus the sadism and arrogance in Maria+Holic's main character.
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Recommended by gloomheart
both boys are in a girls school by the same reason, there´s flesbianism too
also a guy disguise as a girl in a girl's school. though it's new i'm sure it will be a good way to continue with the boy beeing a girl in a girl's enviroment anime.
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Recommended by zinno-chan
Both of them tells about a boy who attending school at All-Girl school, and both of them was a beautiful wo(MEN). Please don't falling in love with her/him
they both have a guy cross dressing but in otoboku(otome wa boku ni koishiteru) there is less yuri scenes than maria+holic. But in Maria+Holic there is multiple text screnes. Otoboku has a sense of seriousness
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Recommended by Denmark-Chan
Both has cross dressing boys that can pass off as female students, because some messed relatives wanted these boys going to an all girls catholic girl. Plus the boys can also be traps as well, b/c they completely fool the girls around them and only a few of them know their secrets.