 If you liked
Kateikyoushi no Oneesan The Animation: H no Hensachi Agechaimasu
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 ...then you might like
Resort Boin
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Both Main Guys are surrounded by attractive women and is able to sleep with them all
Both of them are hentai OVAs starting in 2007 with actually pretty competent animation for the time, both are harem with lots of girls and one guy at play too, there's also the fact that there's the student/teacher scenario in both (with the roles reversed), this is definitely more apparent in Kateikyoushi No Oneesan, since Resort Boin is a sequel and they're in a vacation, but they still call him sensei.
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Recommended by Fabrizio00