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“Actually Mikey … I don’t think jacking you off in the shower will be the end this time.” 

“I thought before I take a shower and wash all the sweat off …

You could get me REALLY dirty.

1. What was your first time having sex like?

2. Are you into BDSM?

3. Do you watch porn, and if so what kind?

4. What’s the weirdest porn you’ve watched?

5. Have you ever watched porn with another person?

6. Do you prefer professional or amateur porn?

7. Add a link to your favorite porn video.

8. What was your first experience with masturbation like?

9. How often do you masturbate?

10. What’s your favorite way to masturbate?

11. Have you ever had shower sex?

12. Have you ever had period sex?

13. Have you ever had sex in someone else’s bed that didn’t belong to anyone involved? (Not including shared spaces like hotels, Airbnb, etc.)

14. Have you ever had sex in a public place?

15. What’s the weirdest place you’ve had sex?

16. What’s your most embarrassing sex story?

17. Have you ever been caught masturbating or having sex?

18. Do you have any sex toys?

19. What is your favorite sex toy?

20. Are there any sex toys that you really want to try?

21. Have you ever tried anal, and if so do you enjoy it?

22. Have you ever used a sex swing?

23. Have you ever had sex standing up?

24. Have you ever recorded yourself having sex or masturbating?

25. Have you ever taken a nude and sent it to someone?

26. Write out a real or made up sexting conversation. (At least 4 lines)

27. What was your first time giving oral like?

28. What was your first time receiving oral like?

29. Do you like giving oral?

30. Do you like receiving oral?

31. Do you prefer clitoral stimulation, penetration, or both?

32. Do you enjoy penetration?

33. Have you ever masturbated in front of another person?

34. Have you ever masturbated with another person?

35. Have you ever masturbated in a public place?

36. Do you enjoy voyeurism? (Being watched or watching other people)

37. Does cross-dressing turn you on?

38. Do you have any kinks that you’re embarrassed about?

39. Have you ever had a sex dream or wet dream? If so, pick one and describe in detail what it was about.

40. Have you ever cheated? If so, do you regret it?

41. Are you into cuckolding?

42. How many orgasms do you typically have in one session?

43. Do you enjoy edging?

44. Have you ever had a ruined orgasm? Was it intentional?

45. What’s the longest you’ve gone without an orgasm?

46. When was the last time you masturbated? Describe what you did in detail.

47. Have you ever gotten injured during sex? If so, what happened?

48. Have you ever contracted any STIs?

49. Have you ever had unprotected sex and accidentally gotten pregnant?

50. Do you prefer to have sex in the morning, afternoon, or night?

51. Have you ever woken up in the middle of the night to have sex or masturbate?

52. How often do you wake up horny?

53. Have you ever had sex with a complete stranger without knowing anything about them?

54. Have you ever done anything sexual while driving?

55. What is your favorite thing about quickies?

56. Have you ever had a sex dream about someone unexpected and freaked out about it? If so, who was it?

57. Have you ever fantasized about having sex with one of your teachers?

58. Do you usually have sex with your eyes open or closed?

59. Have you ever had a threesome? Do you want to?

60. Have you ever had group sex? Do you want to?

61. Have you ever masturbated with a group of people?

62. Do you enjoy dirty talk? If so, give an example of something you would say or would want to hear.

63. Have you ever given a blow job to someone who was wearing a toy?

64. Have you ever had someone give you a blow job while wearing a toy?

65. If you had to choose, would you rather be a dom or a sub?

66. Have you ever done anything sexual with an animal?

67. What is your favorite sex position(s)?

68. What is the weirdest object you’ve masturbated with/humped?

69. What’s the worst place you’ve ever gotten an erection? (Bonus: What’s your most embarrassing story of getting an erection?)

70. Have you ever been so wet that you soaked through your clothes?

71. Do you get really wet, an average amount, or not wet enough?

72. Have you ever had trouble getting it up?

73. Have you ever squirted or made someone squirt?

74. What’s the naughtiest fantasy you’ve ever had about a stranger?

75. Have you ever been so horny in an inappropriate place that you’ve had to excuse yourself?

76. How many fingers do you prefer inside you?

77. Are you loud or quiet?

78. Do you like it rough or gentle?

79. Do you enjoy being on top or bottom?

80. Have you ever dry humped someone while being fully clothed until you had an orgasm?

81. Have you ever had sex while drunk or high?

82. Do you have a specific playlist for sex?

83. Have you ever role played? If so, tell the story.

84. Have you ever kept going even when you were too sensitive?

85. Would you rather have your hair pulled or be spanked during sex?

86. Would you rather be handcuffed or blindfolded?

87. Would you rather cheat or be cheated on?

88. Would you rather get caught masturbating by your parent/guardian or your crush?

89. Would you rather have an obvious orgasm every time you meet someone new or never have an orgasm again?

90. Have you ever had sex with someone who couldn’t satisfy you?

91. What’s something you’ve always wanted to ask about sex but was too afraid to ask?

92. Describe what you would do sexually if you had different genitals for a day.

93. How many dates do you typically need to go on until you feel ready to have sex with someone?

94. In your opinion, what makes someone good in bed?

95. What’s the most flattering thing someone has said about your naked body?

96. Do genital piercings turn you on?

97. How long was the longest orgasm you’ve ever had?

98. What’s the most sensitive part of your body?

99. Is there anything you won’t do in bed?

100. Ask any question you want!

You know how this works. Pick a number or a few and send it to my ask box.