Kisaku

A 2001 H Game by elf, the creators of Shuusaku.

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Kisaku Itou just learned on the newspaper that his brother Shuusaku died, ran over by a car. Does he really care? No. Kisaku however does criticize him for being too quick on his objectives and trying to rape women in an incredibly short period of time, and that his methods are much more slower, methodical, and efficient. Our protagonist then decides to check the newspaper for employment opportunities, finally settling for dormitory manager of Sugimoto Pharmaceuticals, a big company specialized on herbal Chinese medicine.

His objective is very simple: check who are the hottest women around, discover compromising material about them, blackmail, and rape them. However, thanks to his long-term methods, that also means he must keep his job, so it can't be all fun for him, to his annoyance.

Just like his predecessor, Kisaku is a Simulation Game , but like stated above in a much longer frame of time: Kisaku must choose first how he will spend the weeks of the next month, and then when every weekend when it arrives. At determinate points the game, he must obtain a certain number of points to avoid a game over. The game also have mini-game at determinate points, which are either optional or not for the player to win, one of tennis and one of bowling.

Just like his predecessor too, our protagonist also constantly talks back to the player, reacting to his choices, often in an annoyed way, because as turns out, despite being a rapist thug, Kisaku can do pretty, pretty good things. After all, as he himself says, he and the player are like one.

Kisaku was adapted into a OVA series of the same name in 2002.

Tropes used in Kisaku include:

All Girls Want Bad Boys: Seeing Kisaku threaten and cut a delinquent trying to rape her makes Madoka fall head over heels for him.
Arranged Marriage: Presidente Sugimoto tries to set up one with Kisaku. Kisaku tries his best to sabotage it, for the sheer idea of it, since it would interfere with his endless schemes to blackmail and rape women.
Awful Truth: Kisaku ends up revealing to Yuuri while taking her virginity that her father cheats on her mom. That further devastates her along being violated.
Blue and Orange Morality: Kisaku has his own twisted sense of honor where he can only rape women by blackmail, and consensual sex is somehow for losers, even when easily available.
Fat Bastard: Kanji is introduced molesting Yuuri, something Kisaku avoids with help of the player.
Fourth Wall Mail Slot: President Sugimoto will break the wall in certain game overs to tell the player and Kisaku how act to prevent them.
Freudian Excuse: Invoked, with Momoko trying to find one for Kisaku to convince herself he is deep good inside. Kisaku does end up revealing he had a pretty bad childhood, living in poverty and with his family treating him badly.
Girlish Pigtails: Shouko wears twin tails and is pretty girly.
Hair of Gold: Aoi fits the trope almost to an T, being a kind, young, beautiful girl, though not exactly innocent.
Heel Face Door Slam: Kisaku refuses any of Momoko's attempts at redemption.
Heroes Want Redheads: Madoka is the only heroine who can have a happy ending with the protagonist, and just happens to be redhead. Of course, to achieve her ending Kisaku has to be well less malicious than usual.
Hospital Hottie: Aoi Akimoto, one of Kisaku's targets, is a pretty nurse with a curvy body.
The Last of These Is Not Like the Others: Madoka do not resists to Kisaku, and we mean it. When he brings up his blackmail material, she acts amused, and treats having sex with him almost as a challenge. When he tries to rape her, and by that we mean doing no foreplay, in no time she doesn't need it anyway because he arouses her. Basically, she is playing along with his blackmail method, but he really doesn't need it.
May-December Romance: In the Madoka ending, she and Kisaku end up together. Kisaku is stated to be in his fifties and she is only nineteen.
Meganekko: Aoi is a sweet delicate girl with glasses. Sadly for her, Kisaku only sees that sweetness as more of a reason to blackmail and rape her.
Nietzsche Wannabe: Kisaku tries to lecture Momoko about how is natural for him to act solely for self-pleasure because life is all that is to him.
No Fourth Wall: Kisaku not only adresses the player, he outright complains or praises every decision he makes.
Refuge in Audacity: Kisaku manages to get away with using the incredibly rude pronome "kisama" towards President Sugimoto by playing it as them being close, something Sugimoto laughs about.
Smart People Wear Glasses: President Sugimoto and Minami are the highest ranking members of Sugimoto Pharmaceuticals and both wear glasses.
Too Kinky to Torture: Madoka gets pleased by everything Kisaku does, so his efforts to try to make her suffer invariably fail.
Victim Falls For Rapist: Momoko and Madoka both fall for Kisaku, though it is made pretty clear Madoka is attracted towards him even before by comments you hear from her.
Villain Protagonist: Kisaku wants to blackmail women and rape them. Everything else is an accessory to it.
Your Cheating Heart: Tatsuya Himeno is cheating on his unnamed wife, Yuuri's mother, with Madoka, something Kisaku stumbles into.