 If you liked
Princess Princess
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 ...then you might like
Maria†Holic
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Princess Princess and Maria Holic follow the exact same premise, having males crossdressing as females in a school setting. The comedy element in both derives almost exclusively from the unlikely situations that arise from having traps as the main characters. Maria Holic is a parody that targets shows like Marimite with gusto while Princess Princess is not as referential and more interested in mocking yaoi conventions. They may be niche titles, to some extent at least, but these titles are very likely to share at least some of their fanbase.
It’s a trap!
PriPri is set in a all-male school and MH is set in a all-female school, but they have the same feel.
Both are comedies and basically make fun of, respectively, the shounen-ai and shoujo-ai genres.
Also, Yuujirou and Mariya are similar: pretty, blonde, popular, and quite sadistic boys.
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Recommended by RenaPsychoKiller
Crossdressing boys, room for slash, only diff is that Princess Princess is an all-boys school.
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Recommended by BadLuckTuck
You could call Princess Princess the brother anime to Maria Holic. The two anime involve crossdressing, are set in same-sex schools as well as having shounen ai and shoujo ai hints. Although both anime may have these hints there is actually nothing concrete from these genres, at most, a kiss.
Maria Holic, set in an all girls Catholic school could be considered a 'black comedy' since the main character Maria, is known to be a sadistic cross-dressing boy who bullies the bonafide lesbian and focuses on the idea of homosexuality a lot more whereas Princess Princess is more of an all-round comedy that deals with
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