Have you yourself ever been tortured?
Since he was gifted with an abnormally high pain tolerance and sports very thick plating, Overlord often resorts to more extreme measures to satisfy his masochistic desires. Most mechs would classify it as torture.
His most rewarding experiences to date were the scant few times Knockout indulged him with a few surgical procedures, slicing open the triple changer, punishing the tender frame that lay beneath heavy plating. The medic had looked positively gleeful as he cut into subplating and protomesh, held cybernetic organs up to the light for Overlord to see, all before closing him back up again. The sensory feedback Overlord had felt was simply wonderful, true pain lighting up his sensornet, making him cry out and shake in blissful agony.
Has he ever been truly tortured? No. But he’d like to try. Preferably at the hands of an attractive mech or femme.