The application discloses an eartip, an earphone device, an earphone housing and a hearbud housing device. The eartip can include an outer portion, an inner portion, and an encapsulated volume formed by the inner and outer portion, wherein the outer portion is designed to contact the ear canal, and wherein the inner portion is designed to fit upon a stent. In an alternative embodiment, the airtip can include an inverted body, wherein when the inverted body is at least partially folded on itself the inverted body is arranged to include a bulbous region sized for insertion in an ear canal, a cavity internal to the bulbous region that holds a gas, where increasing pressure on the bulbous region releases a portion of the gas.