A therapeutic cushioning device that encourages its user to sleep on the user's right or left side, instead of on the user's back or chest. Generally, the cushioning device includes a head support, a torso support, a leg support, and a hinge member that movably connects the leg support to the torso support. In some instances, the head support includes one or more air tube management system notches to accommodate a facemask. In some instances, the torso support extends from the head support to form an L-shaped cushion. Moreover, the torso support optionally has a perimeter having a concave portion and convex portion, where the concave portion is placed closer to the head support than the convex portion. By encouraging the user to lie in a side position, the cushioning device can help the user avoid challenges associated with sleeping on the user's back or chest.