Triple Sex Tribulations(2008)

Triple Sex Tribulations is an adult anime series based on the Alice Soft game. Kousuke's monotonous life changes when his father arranges for him to live with Madoka, a woman he barely knows. When Madoka's protective older sister Sakura moves in to supervise their arrangement, Kousuke finds himself navigating an unexpected household dynamic with two beautiful women. What begins as an awkward cohabitation evolves into a world of romantic entanglements and intimate complications as the three navigate their newfound living situation together.