[patrickm]

Great idea if you can find the right hotel (not busy hotel, very few security cameras, etc.) Alternative options could be an apartment pool (usually less security), or a secluded spot near a lake, river, or ocean.

If I were doing this, I'd say play the game to determine how long you spend swimming before you pick the swim trunks. Then both people jump in and swim around. Someone's gonna be naked. I'd also add a list of tasks for the naked loser to do while in the pool, so they're not just hiding in a corner for ten minutes.

For picking the swim trunks, you can place them in paper bags, so you don't necessarily have to find swim trunks that look exactly alike. Granted, one person will know if they have the dissolving trunks as soon as they see which pair they got, since someone had to buy them. Maybe head to the pool in just towels and pick the trunks there, so there's less ability to chicken out?