Various embodiments of a male massage apparatus having a flexible body having an exterior portion defining a textured surface and an interior portion defining an axial channel in communication with a proximal opening configured to allow passage of a male organ into the axial channel without establishing substantial contact are disclosed. The interior portion of the flexible body defines a flexible filament arrangement defining concentric rows of flexible elongated filaments that extend along the axial channel and being configured to contact the male organ when the user applies an inward pressure against the flexible body.