1. What’s the dirtiest thought you’ve ever had about a total stranger?
2. Do you prefer sex at night, in the morning, mid-afternoon, or NOW?
3. What’s your favorite way to be seduced?
4. What’s the dirtiest fantasy you’ve had at work?
5. How would you dominate your boss sexually if given the chance?
6. What do you do when you get horny in public?
7. Have you ever masturbated in a public bathroom?
8. What’s the weirdest thing you’ve thought about while touching yourself?
9. What’s the strangest prop you’ve used to get yourself off?
10. Do you remember the first time you felt aroused?
11. Who gave you your first orgasm?
12. Do you remember what that first orgasm felt like?
13. Have you ever had sex with someone whose name you never knew?
14. What’s your favorite thing about a quickie?
15. What the most sexually daring thing you’ve ever done?
16. Have you ever fantasized about fucking one of your teachers?
17. Do you ever mentally strip strangers just for kicks?
18. And then imagine, in dirty detail, what it would be like to fuck them?
19. Have you ever kissed someone of the same sex?
20. What inspires you to make the first move?
21. In your opinion, what does it mean to be good in bed?
22. Have you ever cheated on a boyfriend or girlfriend because you just couldn’t help yourself?
23. Have you ever pushed the boundaries of fidelity to the brink and then retreated just for the rush?
24. Do you have a go-to masturbation fantasy?
25. What kind of porn turns you on?
26. Have you ever had sex with your eyes closed?
27. Have you ever blindfolded or handcuffed your partner?
28. Does naughty talk get you aroused?
29. Are you sure about that, my dirty little forest nymph of a sex goddess?
30. What’s the dirtiest thing someone’s ever said to you during sex?
31. Have you ever watched another couple get it on without them knowing?
32. Have you ever watched another couple have sex with their permission?
33. How would you respond if a couple approached you to be their “third”?
34. What’s the most flattering thing someone’s said about your naked body?
35. When’s the last time you had a vivid sex dream?
36. What do you think an orgy would be like?
37. Have you ever propositioned a total stranger?
38. What does your ideal one-night stand look like?
39. How long does it take you to get yourself off, on average?
40. What’s the weirdest thing that turns you on?
41. Have you ever had a naughty dream about a close friend or family member?
42. Have you ever woken up humping your pillow?
43. When’s the last time you orgasmed in your sleep?
44. What’s the most embarrassing thing that’s happened to you while hooking up?
45. Do you like touching yourself in front of the people you sleep with?
46. What’s the dirtiest text you’ve ever sent or received?
47. Do you prefer professional or amateur porn?
48. What’s your favorite blowjob technique?
49. If you had to pick, would you be a dominatrix or a submissive?
50. Is there anything you won’t do in bed?
Want more dirty questions to ask a guy?