https://en.wikipedia.org/wiki/School_Days_(video_game)

School Days is a Japanese slice-of-life eroge visual novel game developed by 0verflow, released in April 2005, for Windows. It was later remade as a DVD game and ported to PlayStation 2 (PS2) and PlayStation Portable (PSP). The story follows Makoto Ito, a high school student who becomes the love interest of several girls during his second term. School Days has multiple endings depending on the player's choices. Some of these endings later became notorious for their graphic violence.