Ask me these probing NSFW questions ‘cuz I’m bored
SEXYTIMES EXPERIENCES
1. How many people have you had sex with?
2. Can you remember the names of everyone you’ve slept with?
3. With whom did you first do the sexytimes? Was it good?
4. What’s the best sex you’ve ever had?
5. What’s the worst sex you’ve ever had?
6. Where’s the most unusual place you’ve had sex?
7. Where’s the most unusual place you’ve masturbated?
8. Have you ever been caught doing the sexytimes?
9. If you masturbate, when did you start, and how?
10. Have you ever been caught masturbating?
QUEER SHIT
11. How would you describe your sexuality using only adjectives (describing words–busy, fluffy, squishy, etc.)?
12. Have you ever been in a queer relationship?
13. Have you ever been in a straight relationship?
14. How and when did you realise you weren’t straight?
15. Are you out to everyone you know?
16. Where do you meet queer folks to date? Do you find it difficult?
17. If your parents know about your sexuality, how did they react?
18. Does your best friend know about your sexuality? How did they react?
19. Describe your first queer kiss.
20. What’s the queerest shit you’ve ever done?
LET’S GET PHYSICAL
21. Are you happy with your body?
22. What’s the raddest part of your bod, and why?
23. What do you do with your body hair (pubes, underarms, legs, etc.)?
24. Do you have stretch marks? Where?
25. Describe your nipples in too much detail.
26. (Vagina-owners) Do you have an “innie” (small, tucked-in inner labia), or an “outie” (more visible/larger inner labia)?
27. (Vagina-owners) Is it very obvious when you’re turned on (swelling, wetness etc.)?
28. (Penis-owners) Describe the size and shape of your penis. Are you happy with it?
29. (Penis-owners) Have you tasted your own cum? Did you like it?
30. (Breast-owners) How does the size of your breasts compare? Is one bigger than the other?
SEXUAL FANTASY LAND
31. Describe your most unusual/taboo fantasy.
32. Do you fantasise more about real situations, or imaginary/impossible ones?
33. Who’s the oddest person you’ve fantasised about?
34. Do you ever find yourself fantasising absent-mindedly, or is it something you do on purpose?
35. Do you always fantasise while you masturbate?
36. When you fantasise, does it usually lead to masturbation?
37. Have you ever had sex with someone while fantasising about someone else?
38. Do you have any celebrity crushes that you fantasise about?
39. Have you ever fantasised about something by accident, and felt weird about it after?
40. Describe your most sexy fantasy.
KINKTOWN USA
41. How do you feel about BDSM?
42. What’s your most unusual kink?
43. In an SM context, do you prefer giving pain, or receiving it?
44. Do you consider yourself to be dominant, submissive, both, or neither?
45. Describe your most recent bondage experience.
46. In a BDSM context, have you ever referred to anyone as “daddy,” “mommy,” or any similar term?
47. Do you have a kink for any bodily fluids (pee, saliva, blood, tears, cum, etc.)?
48. Have you ever revealed a kink to someone and had them react negatively?
49. Do you have any kinks that you’re ashamed of?
50. How much money have you spent on equipment for your kinks (toys, whips, chains, etc.)?
COME FOR THE QUESTIONS, STAY FOR THE SUBHEADINGS
51. (Vagina-owners) Do you ever squirt when you come?
52. Have you ever come solely from penetration (anal or vaginal)?
53. Can you have an orgasm without your genitals being touched?
54. Describe how you like your genitals to be touched.
55. How sensitive are your nipples? Does nipple play turn you on?
56. Do you find it easier to orgasm with another person, or through masturbation?
57. Have you ever had an orgasm that you weren’t expecting?
58. Do you get off easier from rough contact, or gentle?
59. What’s the best orgasm you’ve ever had?
60. Did it take you a while to have your first orgasm, or were you an early starter?
ORAL FIXATION
61. Do you enjoy giving oral sex? Why?
62. What’s your favourite position in which to receive oral?
63. Describe your oral sex technique.
64. Do you find it easier to give oral to someone with the same genital configuration as you (eg., you both own vaginas/both own penises), or different?
65. Describe the worst oral sex you’ve ever received.
66. Describe the best oral sex you’ve ever received.
67. Do you ever simulate oral sex while masturbating (sucking on dildos etc.)?
68. How sensitive is your mouth? Is it an erogenous zone, for you?
69. Do you like 69ing?
70. Can you deep-throat?
EVERYTHING BUTT
71. Do you like it in the butt?
72. What’s the strangest object you’ve had in your butt?
73. Do you enjoy being rimmed?
74. Can you take a lot in your butt, or just a little?
75. Describe your most recent experience with buttsex.
76. Do you like doing stuff to other people’s butts?
77. (Prostate-owners) Have you ever received a prostate massage?
78. Do you own any buttplugs?
79. Have you ever had an embarrassing buttsex experience?
80. Have you ever pegged someone (ie., worn a strapon and fucked them in the butt)?
SHARING IS CARING
All questions assume you’ve done group sex of some kind
81. Describe your most recent group sex experience.
82. Have you ever had sex with more than two people at once (eg., foursome, moresome)?
83. Have you ever had an orgy? Would you?
84. Do you enjoy watching your partner(s) having sex with others?
85. Do you prefer to arrange group sex beforehand, or allow it to happen organically?
86. Have you ever felt left out during group sex?
87. Have you ever done a gangbang (ie., lots of people have sex with one person, but not each other)?
88. Have you ever teamed up with someone and given a double blowjob/double cunnilingus?
89. Have you ever been penetrated by more than one person at the same time?
90. Have you ever been ejaculated on by more than one person at the same time?
**BONUS DARES**
91. Post a selfie.
92. Post a naked selfie.
93. Tag your biggest tumblr crush.
94. Post your follower count.
95. Press ctrl-v, and post whatever comes up.
96. Tag your top five followers.
97. Post your most recent Facebook status here.
98. Post the last SMS you received.
99. Post the last SMS you sent.
100. Send me $500.
Couple more hours on the train back to the city 😈
