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I Will Protect You by Nagare Ippon is a little too hardcore for me. The sex itself isn't too extreme, but the story is just fucking depressing. Basically this really weak kid named Takeru is the heir to a dojo, his father sends him to a school for delinquents to toughen him up. His childhood friend Miyabi doesn't think he'll cut it over there, so she cuts her hair and says she'll protect him. It turns out that the delinquents that Miyabi protects Takeru from find out that she's a girl and rape her, threatening to hurt Takeru if she resists them. From there, she finds out it was the school's principal that sells her out and he rapes her too. Meanwhile Miyabi is forced to send Takeru away for a week on a character building field trip, and he starts to build himself up a bit. Unknown to him, Miyabi is being raped the entire time, and Takeru only finds out by walking in on her being gangbanged. The lead delinquent hits him in the back of the head with a pipe, and he wakes up to Miyabi giving him a blowjob. The delinquents force the two to have sex, and the principal fucks her and then immediately pulls out. Miyabi realizes that the principal's feels better than Takeru and rejects him, forcing him to watch her get fucked by everyone, while she belittles him. It all closes out with Takeru completely shattered, fucking Miyabi and begging her to tell him that his dick feels the best, while Miyabi just lies there practically comatose.
NTR doesn't usually bother me too badly, but that one just so thoroughly ruined the protagonists that I couldn't really take it.
