Anal

After some thought, you both decide on anal as the next challenge.

"Oh, I dunno, man. If your ass is anywhere near as tight as your throat, you're gonna have to visit the ER after I'm done with you," Bob taunts.

"Wow, I guess this is what all those guys online mean when they talk about porn addiction, isn't it? Maybe we really do need to go to the ER and find you a shrink."

"Fuck you, man."

"No, I'm serious. When we first started watching porn together we just watched lesbians, and now you're fantasizing about some hardcore BDSM shit."

"Well, if BDSM is what you want, we can always order a whip online."

"Uhhh..." you gulp, "well too bad it won't get here in time."

"I have Prime," Bob teases.

"Uhhh... well we already agreed on the challenge its too late to change it," You blush as you awkwardly worm your way out of your own trap.

You edge three times the next morning, driving over to Bob's as soon as you're soft enough to fit back in your pants. You sneak over to his window again and see him cheating again. Good thing I cheated too.

When your friend opens the door, he's as eager to start as ever.

"C'mon, let's play! I need to know who wins!"