Would you rather spend the next two weeks in a cock cage or get a daily ass paddling by Satan?.Would you rather have the best sex of your life for one night or mediocre sex every day for the rest of your life?.Would you rather get sexually aroused any time your boss called or get sexually aroused any time you worked on a spreadsheet?.Would you rather accidentally send a sext to your mom or send a nude to your ex?.Would you rather orgasm every single time you enter a grocery store or never orgasm during sex?.Most of all, enjoy! 100 Dirty 'Would You Rather' Questions But it’s a risk we’re hoping you’re willing to take. Will some of them give you nightmares? Maybe. Luckily, we did the heavy lifting for you and came up with 100 of the best sex-related would you rather questions to ever exist. “I'm considering the option where I have sex with the mermaid, but can you tell me a little more about mermaid vaginas?” Like, just answer the question! We're all trying to have fun here! I kid. I personally find it especially telling when a person follows up with a need for elaborate context. You can learn a whole lot about a person by the choices they make in this game. Add in a sexual twist, and who knows what could happen? To be honest, 'would you rather' questions are a fantastic way to connect with someone new or to get the fire going with someone you’ve been in a relationship with for a long time.