Kimi no Koto ga Daidaidaidaidaisuki na 100-nin no Kanojo - Hakari to Karane to IchaLove H suru HON (Doujinshi) - Oneshot

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Ehhh, besides the fact that they're highschoolers, I don't see a reason this wouldn't happen sooner or later.
 
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The reason why Rentarou doesn't cross the line is because if he did the manga would get pulled by the big cheese, but in doujin land there is no such restrictions
That and it was literally proven he’s just that much of a gentleman
 

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