Hand Maid Mai

Hideo Ozu is an editor in a shady adult video company. For years, he has dreamed of being a motion picture director while his childhood friend Mai Kurosawa has become an upcoming actress. Then one day, his dreams are shattered when Mai takes all of his amateur videos of her and tells him to get out of her life. On his way home after a few drinks, Hideo bumps into Cyberdoll Sara, who makes him mark an invoice. When he arrives at his pad, Hideo is greeted by three Cyberdolls—Mai, Ai and Mie. All three of them happen to look like different age variations of Mai Kurosawa. And when Kurosawa announces the release of a biography video of her using Hideo's old footage, Hideo decides to start his directing dreams over again using his three Cyberdolls.

Synopsis from Anime News Network