This was a custom I made for someone; email me if you’d like one of your own!

You and your wife are on vacation in Chicago, and you’re trying to convince your wife to go down to the hotel bar to pick up another guy. She knows it’s one of your fantasies to see her making out with another guy at the bar and to listen at the door while she’s being fucked by another man. You’ve roleplayed this before but never actually done it, and she’s pretty hesitant at first. She asks a lot of questions, finally agreeing to do it on the condition that you owe her one. Later that night you’re both... Show more