Steamrolled Bareback POV

We hired a new House Manager a few weeks ago. The guy has some experience dealing with young delinquents, but I'll be damned if this guy doesn't have high pressure or something. Unfortunately for the virgin in question, his first punishment session happened to be with one of the worst new offenders we've had in months, and it didn't turn out well for the poor guy's hole. He was caught in an extremely groggy state with some contraband in plain view, which is a huge no-no. Based on how he took to getting steamrolled bareback, my guess is that he will at least do a better job of hiding his infractions in the future.