13InchDick loses.
I'm known to overthink things, so I'm adding some complexity; hope you'll still like it
Game played on skype (no face)
2 rounds
rules:
sunk ship: lose 1 items of clothing until naked.
once naked: sunk ship: toy goes in. Every ship after that, the plug comes out/in as many times as ships are down. (ex. 4 ships down, 4 times)
1st round uses a "medium" sized anal toy. 2nd round a large one.
Round winner earns 2 items of clothing back.
Triple-penalty for the loser:
- reveal the location of 2 ships each round;
- start off wearing only 1 item of clothing
- slap balls/clit with a crop (or similar) on every ship that's sunk.
Winner bonus:
- dress to start off as you wish
- If both rounds are won, you can make the loser play again same rules/start, but 1 extra ship to give up (up to having to give all up, after that it's over); as soon as he's able (time, company etc)