Rapeman

The protagonist of the manga and H-OVA of the same name.

The Fukken Rapeman
High-school teacher by day, Rapeman dons his iconic costumes and operates his Rapeman Services at night. As the name might imply, the latter consist of him stalking and subsequently raping women on a contractual basis, with the ultimate goals of his employers ranging from taking disruptive co-workers down a notch, allowing parents to form a bond with their daughter through a traumatic crisis, or plainly revenge against an unfaithful wife. His motto is "Righting wrongs through penetration".

Rapeman is very serious about his job and will bring his contracts to their respective climax even if he himself finds them distasteful. For the same purpose, he also has adapted a variety of techniques meant to instill more pain in his victims when the latter should become unresponsive or show signs of enjoying their violation.

TCR/Season 1
Contracted to rape some shota who's girly enough anyway.

Episode 9

He's used to being raped and fends Rapeman off, unable to fulfill his contract.