An apparatus for facilitating sleep is disclosed. Embodiments of the sleep system receive a person's lower arm in an arm cavity of a person laying in a sleep-on-side position. An exemplary sleep system has a trunk rest and head rest. Two separated cantilevered supports extending outwardly from the base portion of the head rest are in contact with and supported by a top edge of the trunk rest, thereby defining an arm aperture that receives the person's lower arm when laying in a sleep-on-side position. An arm cavity is defined by lower surfaces of the two cantilevered supports and a trunk rest cantilevered arm cavity surface that extends generally downward and inward.