 If you liked
Boin
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 ...then you might like
Bakunyuu Oyako
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There's the same of plot of a lucky teacher being intimate with his students or just one student in the case of Bakunyuu Oyako, which also features the busty mother of the girl, in Boin there's also a sensei at play, she's not a milf, at least I don't think so, but she's definitely in the more mature part as the busty mom, and finally both are hentai from the same time, mid 2000's where animation for hentai didn't have as much budget as older OVAs, nor had the technology to conceal the lack of frames, so there's the same energy from both.
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Recommended by Fabrizio00