YES, THIS! He'd be crying from overstimulation, let alone the torture, and then after a while he just wouldn't be able to help but come again, and then it would get *worse* when he's even more sensitive than before and then-- it just. keeps. going.

on his cock, one of those milking machines but on a setting faster than a normal human could take, in his ass, a huge, custom-designed for his body, vibrating dildo that stimulates prostate and perineum, and aaaallll the nipple play... (clover clamps, anyone?)