[MessyJeopardy]

I'm on as MessyJeopardy. I am not a great player, but looking to play.

With a name like mine, my proposed stakes should not be a shock...players would both need to wear 5 articles of clothing, with the last article being tight underwear or pantyhose or the like...

Pawn - lose an article of clothing (first 4) / pour a glass of water over your head (last 4)
Knight - food (to be decided) down the back of the shorts
Bishop - food (to be decided) down the front of the shorts
Castle - pie to the face
Queen - slime / gunge over the head
Check - crack an egg (opponent's choice on location)
Mate - strip off and show off (or to be decided - I'm game!)

It would be a proper mess, and take some planning, but...

Added: I'd be more than willing to discuss other approaches, too...