Give yourself a chip for each item of clothing you are wearing and make bets on whatever it is you want, a sports game, an upcoming TV show debut, even people watch and make your bets accordingly. Negotiate what constitutes a fair bet (don't let your opponent make any too safe bets! and block them if they try to bet too high on safer bets) between you and debate the results as a fun little competition for the two of you! Three options upon winning a bet, you either get your chips returned or get your chips back but doubled (2:1 betting) - just pick before the first bet is made. Simply refunding the chips may be the best option for a game of Strip Bets, unless of course you would like to put more clothes on! If you cannot afford a bet, the maximum amount you can afford will be placed, if you are completely tapped out then no bet will be created. bet on anything, A TV show, sports game, people watching...
Instead of using individual chips to represent your clothing items, use multiples of 10 or 100 for much bigger betting potential. Add a forfeit, such as little punishments or drinks, to allow for cancelling of lost bets as a little extra fun.
Your above settings will be locked in as soon as you place your first bet.