Wow, best of getdare on his first post. Kudos. Great dare, works with an arbitrary number of people, complex without being complicated. This seems like an interesting dare to be used as a forfeit. The group could play a game of chance or skill, and the first eliminated, or everyone except the winner, or some group of people, could be forced to play. Alternatively, draw straws (or something) for who plays, but include some positive options (for instance, instead of only losing clothes, add a card where you get to take clothes from another player).
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