An eyeglass cushioning device useful for diminishing pressure placed upon a user's ears and surrounding area through extended headphone, goggle, protective eyewear and circumaural headset use. The eyeglass cushioning device includes a sleeve member, at least one headset spacer and a cushioning pad. The sleeve member is flexible and configured to slide over the temple of a user-wearer's eyeglasses. The headset spacer is attached to the sleeve member, and may be comprised of an upper and lower spacer relative to the eyeglass temple, configured to minimize deformation of the ear, and thereby diminish discomfort of a user-wearer with extended headset use. The cushioning pad is a compliant material configured to wrap around the back of the ear of a user-wearer during headphone, headset, protective eyewear or goggle use.