This is the story of a young pegasus stallion, or you specifically. After the passing of your mother, and your ever increasing distant father, your brother has never felt safe in the cloud home. Afraid of heights and normal life in Cloudsdale, you decide to abandon your former life to start a new one on the ground, in a town called Ponyville. While there you find a cute mare that runs the local post office who goes by the name of Ditzy Doo.

Pinwheel is a simple earth pony. She lives in a little cottage outside Sweet Apple Acres, she makes pinwheels for a living, and she has plenty of friends. But one day, when she goes flying with her good pegasus pal Dizzy, she takes a fall and lands in the dark crossroads between life and death! If that's not bad enough, the Grim Reaper is forcing her to bargain for her life! And what will she do when that bargain takes a somewhat more...personal turn?