Chris talks about his first time giving spankings, during a kinky Monopoly game:
We’d planned out a game of spanking Monopoly as a way to break the ice: both Raven and T had been spanked before, but I had never spanked anyone beyond the single yardstick swat above. After dinner, they went to change and came back wearing thin jersey-type shorts. I can’t remember which one got it first, but during the course of the game, both young lady’s went over my lap several times and got the seats of their shorts warmed. There were several memorable moments, including when I was spanking Raven with a long-handled bathbrush and the head suddenly snapped off and flew across the room, almost breaking a lamp.
I’m not entirely sure why beyond my shyness and lack of experience at the time, but the shorts stayed up through the game until the very end when Raven landed on Boardwalk, which I owned and had placed a hotel on. Since the default for this was rather high, I offered her the choice to drop her shorts and take a smaller number of swats. Next thing I knew, her bare bottom was across my lap, and I was almost too nervous to properly spank her, but a few minutes later she was standing back up and rubbing her buns.
I’ve never looked at a Monopoly board quite the same way since.
Those evil plutocrat landlords! The things they’ll do to the sweet and innocent tenants…