Some Playful Questions...

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116 Questions

Have you ever slept naked?

What's your bra size, or dick length?

Where was or would you want your first time to be and why?

Have you ever shown anyone your body parts and asked advice?

Have you ever seen any of your relatives naked?

Do you prefer doing it in the dark or in the light?

What's your greatest fantasy?

Would you suck on anyone's toes?

Where do you think would be the weirdest place to have sex?

Would you have sex there?

What and who turns you on?

What celebrity would you have sex with?

Whose the sexiest male you know?

Whose the sexiest female you know?

How many people would you have sex with at once?

Have you ever put on a strip show?

Have you ever seen a strip show?

Have you ever seen any of your friends naked?

Have you ever had a fantasy about a teacher?

Have you ever gone skinny dipping?

If you could be a spice what would it be?

Have you ever worn your underwear two days in a row?

Have you ever compared your body parts to someone else's while you were both naked?

Have you ever took a piss standing up or squatting in the woods?

What was the weirdest place you have ever done something with someone?

Have you parents ever caught you doing anything?

Have you ever caught them?

Would you ever have sex in the ocean?

Have you ever gotten sand up you?

Have you ever run or walked around your house nude?

What do you wear to bed?

Have you ever done anything with someone in your parents bed?

Would you ever consider rubbing hot oil or cream all over your guy or girl?

Have you ever used lubricant?

Have you ever taken off your bra or underwear on a main road?

Would you ever do anything on a Ferris wheel?

Have you ever tasted cum or female juice?

How old were you when you got your first real kiss?

Have you ever done anything with anyone in a pool, hot tub, or bath tub?

Have you ever tied up or hand cuffed anybody?

Were you a witness to someone having sex?

Would you ever have phone sex?

Would you ever do anyone in a tree?

Would you ever have sex with your best friend?

Would you have sex withsomeone you don't even know?

Do you find physical pain like spanking an element of good sex?

Do you find older women attractive?

Do you find older men attractive?

Would you rather have sex with or without a condom?

Who was the person you kissed that was the best?

What excuse would you give your parents if they caught you having sex?

What color is your pubic hair?

Does your hair color match the color of your pubic hair?

Have you ever opened your eyes while making out?

How many people have you slept with?

Have you ever had anal sex?

Where on your body is your favourite place to be touched?

When was the last time you had a dirty dream?

If you could have sex anywhere in the world, where would it be?

What’s the best sex you’ve ever had?

What’s your favourite position?

Name a sex position you’d like to try

What was your best orgasm ever?

Have you ever sent nudes of yourself?

Are you loud or quiet during sex?

Have you ever tried using food during foreplay?

Have you ever made a sex tape?

What’s the first thing that sexually attracts you to someone?

When it comes to BDSM, how far have you gone/would go?

Do you ever read erotic fiction?

What’s your favourite toy?

Have you joined the mile high club?

Would you say you’re kinky?

Do you enjoy shower sex?

Where’s the weirdest place you’ve ever masturbated?

Do you like to be spanked?

What was your most embarrassing sexual experience?

Have you ever fantasised about someone else during sex?

Have you ever cried or fallen asleep during sex?

Do you prefer eye contact or not during sex?

Do you like to kiss during sex?

Do you get tired after sex?

What’s a surefire way to turn you on?

Do you like dirty talk?

Have you had sex in a car?

Do you like sexting?

What’s the shortest and longest time it’s ever taken for you to have an orgasm?

Have you ever masturbated in front of your partner?

Have you ever been choked during sex?

Have you ever had a friend with benefits?

Have you ever worn lingerie?

Have you ever had sex outdoors?

Have you ever watched porn with someone?

Have you ever kissed multiple people in one night?

Have you ever had sex in a bathroom stall?

Have you ever tasted yourself?

Have you ever worn a butt plug?

Have you ever used a sex swing?

Have you ever had sex in a classroom or office?

Have you ever gone skinny dipping?

Have you ever been pinned down?

Have you ever had sex while drunk?

Have you ever had sex while high?

Have you ever orgasmed five times in one day?

Have you ever had morning sex?

Have you ever eaten food off of your lover’s naked body?

Have you ever used hot wax?

Have you ever worn crotchless underwear?

Have you ever had sex on the floor?

Have you ever had sex in front of a mirror?

What is your favorite porn category?

Do you like to have sex outdoors?

How long do you like foreplay to last?

Do you prefer being the dominant one or the submissive one?

Do you prefer rough or gentle sex?

Do you make noises during sex?

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.

reblog if you masturbate while on tumblr 😏

NSFW QUESTIONS

Pleaseeeeee ask me some of these

1: Kitchen counter, couch, or on top of the dryer? 2: Your last sexual encounter: Good or bad, and why?  3: A fictional person that you think would be good in bed: 4: Something that never fails to make you horny: 5: Where is one place you would never have sex: 6: The most awkward moment during a sexual experience was when: 7: Weirdest thing that ever made you horny: 8: What is the best way to sexually bind someone: 9: What is the fastest way to make you horny:  10: Top or bottom?  11: We were about to have sex but then ________ 12: Is one orgasm enough? Are multiple orgasms necessary? 13: Something that you have hidden in your room that you don’t want anyone to find: 14: Weirdest nickname a significant other has ever called you: 15: Two things you like [or dislike] about oral sex: 16: Weirdest sexual act some has performed [or tried to perform] on/with you:  17: Have you ever tasted yourself? [If no, would you?] [If yes, what did you think?] 18: Is it ever okay to not use a condom: 19: Who was the sexiest teacher you ever had? 20: A food that you would like to use during a sexual experience: 21: How big is too big? 22: One sexual thing you would never do: 23: Biggest turn on? 24: Three spots that drive you insane:  25: Worst possible time to get horny: 26: Do you like it when your sexual partner moans? 27: Worst sexual idea you ever had: 28: How much fapping is too much fapping: 29: Best sexual complement you ever got: 30: Bald, landing strip, Jumanji: 31: Is it good sex if you don’t nut: 32: Fill in the blank: “If they ____________, we are fucking. 33: What your favorite part of your body? 34: Favorite foreplay activities: 35: Love or Sex? 36: What do you wear to bed? 37: When was the first time you masturbated? 38: Do you have any nude/masturbating pictures/video of yourself? 39: Have you ever/when was the last time you had sex outside? 40: Have/would you ever have sex in public? 41: Have/would you ever had a threesome? 42: What is one random object you’ve used to masturbate? 43: Have/would you ever masturbate at work/school? 44: Have/would you ever have sex on a plane? 45: What is one song you’d like to have sex to? 46: What is something nonsexual that makes you horny? 47: Most attractive celebrity? 48: Do you watch gay/lesbian porn? why/why not? 49: If a child was born on the occasion of the last time you had sex, how old would that child be right now? 50: Has anyone ever posted nude pictures of you online? 51: What is one thing that NEVER makes you horny? 52: Do you have stretch marks? (How do you feel about them? Has anyone ever had a problem with them?) 53: Do you like giving head? (why/why not) 54: How do you feel about tattoos on someone you are interested in? 55: How would you feel about taking someones virginity? 56: Is there any food you would NOT recommend using during a sexual encounter? 57: Is there anything you do on Tumblr that you would not like your significant other to see? 58: Do you own any sex toys? (what is it? how long have you had it?)  59: Would you give your significant other unrestricted access to your Tumblr for a day? 60: Would you be offended if your significant other suggested you get plastic surgery? 61: Would you rather be a pornstar or a prostitute? 62: Do you watch porn? 63: How small is too small? 64: Have you ever been called a freak? Why? 65: Who gave you your last kiss? Did it mean anything? 66: Would you switch phones with your significant other for a day? 67: Do you feel comfortable going “commando”? 68: Would you have a problem with going down on someone if they hadn’t shaved their pubic hair? 69: If you could give yourself head, would you? 70: Booty or Boobs? 71: If you had a penis, what would you name it? 72: Have you ever been on an official date? 73: Have you ever cheated on someone? (Why?) 74: If you were a stripper, what would your name be? 75: Have you ever had sex in your parents bed? (Would you?) 76: How would you react if you found out your parents had sex in your bed? 77: What was your reaction the first time you saw a penis/vagina? 78: If you had a penis for a day, what are five things you would do?

Sexual Questions ;)

1. First kiss? 2. First time masturbating? 3. First sex toy? 4. First kink tried? 5. First time doing oral? 6. First time having sex?
 -Turn Ons 7. Biggest turn on? 8. Biggest turn off? 9. Quickest way to get horny? 10. Weirdest thing that ever turned you on? 11. Top 3 places to be touched? 12. Ultimate fantasy? 13. Do you like the idea of a three or moresome? 14. Do you send nudes? Do you like receiving them?
 -Preferences 15. Sex or masturbation? 16. Spit or swallow? 17. Cut or uncut dicks? 18. Rough or sensual sex? 19. Oldest person you’d sleep with? 20. Loud or quiet partners? 21. How much foreplay do you like? 22. How much teasing do you like? 23. What is too big for you to take? 24. Do you do hookups or only sleep with a partner? 25. How much kissing do you like during sex? 26. What’s the most attractive part of the body?
 -Location 27. Would you have sex in public? 28. Last place you had sex? 29. Where would you most like to have sex? 30. Do you like spontaneous sex, or do you need to be in the mood? 31. Could you go through with a hookup at a strangers house?
 -Kinks 32. What’s your biggest kink? 33. Are you okay with name calling in bed? 34. Would you do any BDSM? 35. Do you prefer to tie somebody up or be tied up? 36. Do you like orgasm denial/forced orgasm? 37. Do you like overstimulation? 38. Do you like having pain involved? 39. Do you like biting/being bitten? 40. Have you ever been made to/made somebody beg for it? 41. Do you have any strange or extreme kinks? 42. Have any roleplaying preferences? 
-Masturbation 43. Do you own sex toys? How many? 44. What do you masturbate to? 45. How often do you masturbate? 46. How often do you use sex toys to masturbate? 47. Do you masturbate with penetration? 48. Do you go for multiple rounds or settle at one or no orgasms?
 -Oral 49. Do you enjoy giving oral? 50. Do you prefer giving or receiving oral? 51. What makes you orgasm the fastest when receiving oral? 53. Can you deepthroat? 
54. Do you like playing with your clit? If so how do you prefer to do it? 55. What’s your breast size? 56. How often do you go braless? 57. Do you finger yourself? 58. How familiar are you with your g-spot? 59. Do you squirt?
 -Sex 60. How often do you do unprotected sex? 61. How loud are you in bed? 62. Do you enjoy having nipples played with? 63. Do you like/dislike cum? 64. How good are you at dirty talk? 65. Do you get sleepy after an orgasm? 
66. Do you trim, shave or leave pubic hair untouched? 67. How do you prefer partners pubic hair? 68. How many orgasms can you have in a day? 69. How many other people know your bra size? 70. What do you wear to bed? 71. Any funny sex stories? 72. What food if any would you use during sex? 73. Would you give somebody a sex toy as a gift? 74. What’s the weirdest porn you’ve ever seen? 75. Do you often get horny in public? 76. Ever used something that isn’t made for sex in the bedroom? 77. Have you ever walked in on somebody or been walked in on? 78. Do you have any friends you’d sleep with?