A sleeping support assembly for reposing in a prone position includes a first cushion that is configured to support a torso of a user. A second cushion is coupled to and extends from a first end of the first cushion. A penetration is positioned through the second cushion. The penetration is substantially ovally shaped. The penetration is configured to support a head of the user who is pronely positioned upon the first cushion such that a spine of the user is aligned. The arms of the user are positioned such that blood flow to the arms is unimpaired.