Worst punishment(degradation) - Unexpectedly being ordered to crawl over to the plug hole in the staff shower room and lick the drain hole cover-it was full of pubes. These had to be licked up then swallowed.
Worst punishment(pain) To self whip cock end with thin rubber band pulled to its max stretch, A dice was rolled ten times to decide on the number of whips to be administered and waiting for the dice to stop each throw just added to the torment. The band had to hit the same spot each time and my cock was clsoe to bleeding at the end of the sess. If i didn't pull the band to what master considered max stretch i would have to repeat it. The pain at the end of37 whips of my bell end at the same spot was indescribable.
Best moment-hearing master masturbating with true pleasure and gently moaning as I performed for Him.
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