| Gun to your head
The rules: You must choose to sleep with one of the following people or fictional characters. If you choose both you get shot dead. If you prefer to die, you have to do both. Once you've chosen you get to think up the next diabolical choice. Of course, you have to keep it legal. No under 18s, no animals. Dead people are a-okay, but we'll all assume you don't mean their corpses...
You can make it as difficult (ie. Angelina Jolie vs. Heidi Klum) or evil (Richard Simmons vs. George W. Bush) as you wish.
Gun to your head:
Jessica Rabbit or the Little Mermaid? | 
