Jessie Oliver is a somewhat shy, feminine boy who's always mistaken for a girl thanks to his looks. His life gets flipped upside down when he's enrolled in Pierce Private Academy and moves into the boys' dorms... only to be turned upside down again when he's magically turned into a girl! Romance, comedy, and general gender-bendery hijinks and drama await as Jessie meets a colorful cast of weirdos and learns to cope with his, er, her new lot in life.