Boys Love manga Crimson Spell has an extra chapter in one of its volumes dedicated to a tentacle monster raping one of the main characters. The boyfriend eventually has its way with the father offscreen while the girl is out, resulting in his approving the marriage.
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Fortunately they're all rescued before anything hentai happens. Played with in the second season of Bludgeoning Angel Dokuro-chan , where a set of tentacles decide to ignore the three girls in the enclosed space they are in, and rape the male character instead, to which he lampshades that this is so different from what should be happening in an anime. They're "not technically hentai" but very, very close, resulting in an abundance of--ahem--" not technically NSFW " scenes. As the story progresses, he becomes nothing more than a head atop a mass of tentacles.
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And this is just a partial description. Possibly referenced in the twelfth episode of the second season of Shuffle , where Sia's dad replaces the water in the swimming pool with eels.
Hey, how long are you going to watch, you perverts?
And so, surprise surprise, there is.