An exemplary uncomfortable sound pressure estimation system includes an HTL section for receiving information of hearing threshold levels respectively for a plurality of frequencies; a UCL measurement determination section for determining at least two measurement points at which to measure uncomfortable sound pressures, the at least two measurement points defining a first and a second frequency concerning a first and a second hearing threshold level; a UCL measurement section for measuring uncomfortable sound pressures with respect to the at least two measurement points; a calculation section for calculating a criterion concerning auditory characteristics by using the respective hearing threshold levels and uncomfortable sound pressures for the at least two points; and a UCL estimation section for estimating an uncomfortable sound pressure at a frequency corresponding to a given acquired hearing threshold level, according to the predetermined criterion.