How about a messy wheel? Make a wheel on wheel decide with a bunch of different messes and one "done" wedge. You can weigh the wedges depending on how messy they are. (the bigger the mess the smaller the wedge.) Maybe no repeats depending on how many wedges.
Also, have him stuff his mouth with marshmallows so they are all puffed up while in stripper wear?
I was trying to think of a fun predicament, but most kinda get elaborate. Maybe have him try to squat in place with heels for a while with his butt over a buzzer or holding something messy over him? If he buzzes or drops it he gets a punishment?
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