100 NSFW TMI Questions you probably have never been asked:
1. Are you a virgin?
2. Does anyone besides you know your bra/penis size?
3. Do you know anyone who has any STDs?
4. Were you married when you first lost your virginity?
5. Do you swear under celibacy?
6. When did you first lose your virginity? If you haven't, when would you like to?
7. Have you ever gotten tricked into aphrodisiacs or alcohol for sex?
8. Have you walked in on someone masturbating/having sex?
9. Have you ever seen someone masturbate or have sex with their permission?
10. Where is the weirdest place you have had sex?
11. If you had to chose one, would you have outdoor sex or car sex?
12. When was the age you first masturbated? Whether you knew it or not?
13. Have you ever helped someone "finish"?
14. Have you ever had an erection in the past month? (clitorial counts, too)
15. When was the last time you have had an erection? (clitorial counts, too)
16. Have you ever had an erection and someone noticed?
17. What is your method of masturbation? (ie. toys, clitorial, prostate)
18. What is your bra/penis size?
19. Has anyone seen your private parts other than yourself or a family member?
20. What is the strangest thing you have ever put up your vagina/anus?
21. Do you like rough sex or intimate sex better?
22. When was the last time you masturbated?
23. When was the last time you had sex?
24. When was the last time you watched porn?
25. Have you ever bought a sex toy? If so, which one did you buy last? First sex toy? If not, which one do you plan on buying when you do?
26. Guys: Circumsized?
27. Which not-genital part of your body do you like being touched?
28. Which genital part of your body do you like being touched?
29. Girls: Are you able to achieve orgasm just through breast stimulation?
30. What color/type of underwear are you wearing?
31. Have you ever sent someone a picture or video of you in the nude? Did it include sexual actions?
32. Have you ever posted a picture of image of you in the nude on a website? Did it include sexual actions?
33. Have you ever anonymously sent/posted a picture or video of yourself in the nude? Did it include sexual actions?
34. Have you anonymously sent a sexual ask to someone on tumblr?
35. When was the last time you have had a wet dream?
36. Which wet dream was your favorite?
37. Is there a friend you would willingly have sex with?
38. Is there a celebrity/character you would willingly have sex with?
39. Have you ever masturbated with someone?
40. Have you ever took a shower with someone that is not a family member?
41. Favorite sexual position? If you are a virgin, which position interests you?
42. Do you like being called a slut or whore in bed?
43. Are you into any BDSM?
44. Have you ever wanted to have sex with someone but knew you couldnt for any reason? Why?
45. Turn on's?
46. Turn off's?
47. Have you ever had a sexual fantasy about someone? Was it about anyone other than your lover?
48. Have you ever had phone sex? Video sex? Chat box sex?
49. What was the weirdest thing that has ever turned you on?
50. Do you like dirty talk?
51. Are you loud or quiet during sex? Masturbation?
52. Have you ever been inturrepted during sex or masturbation? Who/what?
53. Most embarressing sex/masturbation story?
54. Most hilarious sex/masturbation story?
55. What kind of porn do you like to watch?
56. First type of porn you have ever watched? (ie. lesbian, hentai, threesome)
57. What was the most recent type of porn you have ever watched? What category was it under?
58. Most hilarious/stupidest porn you have ever watched?
59. Have you ever fantasized over someone older than you? How much older? Younger? How much younger?
60. Favorite sex toy (if any)?
61. Have you ever had to break up with/divorce someone because you weren't satisfied with their sex?
62. Have you ever used anything/gotten any surgeries to improve sexual performance/feel?
63. If someone you knew asked for a nude image, would you do it? What about a tumblr follower?
64. Have you ever told someone any wet dreams/fantasies you've had about them?
65. Do you like to have sex like they do in pornos?
66. Have you ever confessed to someone that you got an erection over them? What about masturbated to them?
67. Are you able to be secretive when you masturbate? (like able to be quiet so no one can hear?)
68. When was the first time you achieved orgasm?
69. Is there only one way so far that you have been able to achieve orgasm? (ie. only by using toys, only from 1 positon,only from masturbating a certain way)
70. Favorite type of oral?
71. Strangest sexual positon you've tried?
72. Have you ever made up a sexual postion?
73. Girls: During sex, vaginal or anal?
74. Girls: During masturbation, clitorial, vaginal, or anal?
75. Do you like to be dominant or submissive?
76. Have you ever masturbated to someone?
77. Have you ever masturbated because your sexual partner wasn't there when you needed them?
78. Have you ever had a one night stand? Do you still keep in contact with them?
79. Have you ever had a friends with benefits? Are they still beneficial?
80. Have you ever had sex with someone who wasnt your partner?
81. Has any of your partners had sex with someone else?
82. Have you ever gotten pregnant? Were they your lover's or someone else's?
83. Birth control or condoms?
84. Do you ever masturbate to porn?
85. Does anyone know you masturbate? Did you have to tell them?
86. Did your parents ever find out you were sexually active?
87. Do you have any STDs?
88. Have you ever masturbated to a fictonal character or celebrity?
89. Have you ever had sex during "7 minutes in heaven"?
90. Spit or swallow? Or do you not like oral?
91. Have you ever been rejected for sex? Have you ever rejected someone else?
92. Do you have someone who said they are willing to take away your virginity if you havent lost it by a set age or if you just want to have a good time?
93. Have you ever experiented with the opposite sex?
94. When you first lost your virginity, was it intended or spontanious?
95. Has anyone ever walked in when you were taking a shower with someone?
96. Did you ever tell someone once you lost your virginity?
97. Does your lover know if you have masturbated?
98. Does your lover know that you want to have sex with them but cant?
99. Do you like masturbation?
100. (Asker's ask) If i were to ask you if we could have sex, would you say yes?