Looking for a fun, flirty way to really get to know someone, build anticipation for what's coming later, or add some spice to a long-distance relationship? "Would You Rather?" fits the bill perfectly! It's simple to play, and the raunchy would-you-rather prompts below guarantee the conversation keeps flowing 😉

107 Dirty Would You Rather Questions

1. Would you rather I stopped hugging you or stopped kissing you forever?
2. Would you rather have sex in the morning or at night?
3. Would you rather have sex with the lights on or off?
4. Would you rather be on top or underneath? Learn: How to confidently ride your man.
5. Would you rather only have sex in the bedroom, or only outside it?
6. Would you rather have romantic sex or kinky sex?
7. Would you rather watch others have sex in front of you, or have others watch you?
8. Would you rather have anal sex or get anally fingered tonight?
9. Would you rather have only anal sex or only oral sex forever? 27 blow job tips.
10. Would you rather get sexy pictures or sexy videos?
11. Would you rather narrate every detail of your sex life to someone, or hear every detail of theirs? (Great one for playing with friends!)
12. Would you rather be stuck doing Doggy Style or Missionary forever?
13. Would you rather marry your first-ever partner or your most recent ex?
14. Would you rather have sex wearing socks or a t-shirt?
15. Would you rather strip naked in front of 50 strangers, or five people you actually know?
16. Would you rather sleep with someone who remembers every detail about you — good and bad — or someone who forgets everything about you entirely?
17. Would you rather be labeled a prude or a slut? Learn how to embrace being a total slut.
18. Would you rather quietly go down on someone at the movies, or have someone go down on you there?
19. Would you rather lose your best sex memories forever, or keep them but have mediocre sex for the rest of your life?
20. Would you rather confess your feelings to your crush right now, or lose the chance forever?
21. Would you rather have a threesome with me plus another woman, or me plus another man? Try the Eiffel Tower sex position next time!
22. Would you rather accidentally send a sexy text to your parents, or to your boss?
23. Would you rather lick ice cream or chocolate syrup off your partner's body?
24. Would you rather get kissed right after giving oral, or kiss someone right after they went down on you?
25. Would you rather get caught masturbating or caught mid-sex?
26. Would you rather watch porn or read erotica?
27. Would you rather have sex only with music playing, or never with music playing? Check out this sex song playlist.
28. Would you rather see a nude photo of whoever's sitting to your left, or your right?
29. Would you rather burp or fart every single time you orgasm?
30. Would you rather burst into uncontrollable sobbing or laughter every time you climax?
31. Would you rather spend forever with your very first kiss, or be single for life?
32. Would you rather have phone sex or cybersex with your celebrity crush? How to make phone sex awesome!
33. Would you rather make out with your best friend or a total stranger?
34. Would you rather lose every sexual memory you have, or become a virgin again?
35. Would you rather randomly orgasm at unexpected moments during the day, or never orgasm during sex again? Discover how to orgasm.
36. Would you rather always be trying something new in bed, or never try anything new sexually again?
37. Would you rather be locked in chastity (cage or belt) for a week, or be forced to orgasm nonstop for that same week?
38. Would you rather date someone amazing in bed but a terrible kisser, or a fantastic kisser who's bad in bed? 22 tips for kissing.
39. Would you rather sleep with someone who smells bad, or whose moans you can't stand?
40. Would you rather have incredible sex but never orgasm, or orgasm every time but the sex itself is mediocre?
41. Would you rather be forced to touch yourself until it's uncomfortable every time you masturbate, or lose the ability to self-pleasure forever?
42. Would you rather sleep with someone gorgeous who's terrible in bed, or someone unattractive who's incredible in bed?
43. Would you rather watch a sex tape featuring your own parents, or have your parents watch yours?
44. Would you rather give sex advice to your grandparents, or receive it from them?
45. Would you rather never dine out again, or never receive oral again?
46. Would you rather hold unbroken eye contact with your partner for 6 straight hours, or never make eye contact with them again?
47. Would you rather permanently give up masturbation or partnered sex?
48. Would you rather give up your favorite meal forever, or give up sex forever?
49. Would you rather be a sugar baby, or a sugar daddy/mommy?
50. Would you rather have completely silent sex forever, or have your partner scream at max volume every single time?
51. Would you rather be banned from ever talking about sex, or have to narrate everything you're doing out loud during it?
52. Would you rather meet your dream partner but only ever have phone or cyber sex with them, or be physically intimate forever with someone you can't stand?
53. Would you rather never show your partner any public affection again (no kissing, hugging, hand-holding), or have to go completely over-the-top with PDA constantly?
54. Would you rather have sex while freezing, or while sweating profusely from heat?
55. Would you rather try a new sex position or a new toy every single month for life?
56. Would you rather give up kissing forever, or give up receiving oral forever?
57. Would you rather sleep in a separate room but have amazing sex, or share a bed but have disappointing sex?
58. Would you rather watch porn together, or film yourselves having sex?
59. Would you rather be submissive or take the dominant role in bed?
60. Would you rather have painful hickeys hidden where nobody sees them, or one massive painful hickey somewhere visible?
61. Would you rather wear a blindfold or a ballgag during sex?
62. Would you rather your family stumbled on your browser history, or your sexting?
63. Would you rather have sex with someone else while your partner watches, or watch your partner have sex with someone else? (If option two sounds hot, you might be into cuckoldry!)
64. Would you rather orgasm every time you cry, or cry every time you orgasm?
65. Would you rather be known as terrible in bed, or a terrible kisser?
66. Would you rather never know when your orgasm is coming, or know exactly but only get 60 seconds to make it happen?
67. Would you rather wake up to being penetrated, or wake up to oral?
68. Would you rather sext (sexting tips) nonstop all day, or get one guaranteed, uninterrupted phone sex session?
69. Would you rather go skinny dipping or sunbathe completely nude?
70. Would you rather have someone stimulate the back of your knee, or the inside of your elbow?
71. Would you rather have sex in a secluded cabin in the woods or sex in an upscale hotel room?
72. Would you rather see your partner in lace lingerie, or leather?
73. Would you rather reveal all your NSFW fantasies at once, or drip them out slowly over time?
74. Would you rather get freaky in a mirror-covered room, or in front of a window where you could be seen?
75. Would you rather play strip poker or dirty Twister (once you've finished these spicy prompts, of course)?
76. Would you rather deal with sexual problems or financial problems in your relationship?
77. Would you rather only have kinky sex or only vanilla sex forever? Discover what being kinky really means.
78. Would you rather wear a regular costume to an adult party, or a sexy costume to a family event?
79. Would you rather wear your partner's clothes in public for a week, or streak in public for 5 minutes?
80. Would you rather lick flavored oil off your partner, or have them lick it off you?
81. Would you rather eat something disgusting while blindfolded, or give oral to someone whose identity is a mystery?
82. Would you rather develop feelings for a friend with benefits who doesn't feel the same, or have someone catch feelings for you that you can't return?
83. Would you rather suck someone's toes, or have yours sucked? 22 toe sucking tips, techniques and positions.
84. Would you rather be with a partner who stays completely still during sex, or one who moves but stays totally silent?
85. Would you rather get intimate with someone who has bad breath, or bad body odor?
86. Would you rather get so wet it shows through your clothes just once, or never get wet again?
87. Would you rather experiment with hot wax, or ice cubes?
88. Would you rather every one of your social media followers see a nude photo of you, or read one of your raunchiest fantasies?
89. Would you rather accidentally wear see-through clothing in public, or accidentally flash someone with no underwear on?
90. Would you rather give oral with something spicy in your mouth, or have someone go down on you with something spicy in theirs?
91. Would you rather accidentally moan your ex's name during sex, or have your partner moan theirs?
92. Would you rather only ever have sex in public places, or only ever have missionary sex in bed forever?
93. Would you rather have sex after a terrible date, or miss out on sex after an amazing one where the chemistry was obvious?
94. Would you rather your partner only ever use their hands (fingering), or only their mouth on you? 85 tips on how to give a woman great oral sex.
95. Would you rather have sex knowing your breath smells bad, or your body does?
96. Would you rather be undressed using only teeth, or only hands?
97. Would you rather have sex outdoors during a tornado warning, or outdoors while getting eaten alive by mosquitoes?
98. Would you rather never feel sexual tension again but always have great sex, or feel constant intense tension but never have great sex again?
99. Would you rather guess my lip gloss flavor by kissing me, or my perfume by smelling me?
100. Would you rather wake up to soft kisses, or intense fondling?
101. Would you rather have a partner who finds you incredibly hot but not very bright, or one who's madly in love but not sexually attracted to you?
102. Would you rather get flogged with a stingy toy (a thin cane) or a thuddy one (a paddle)? Impact play tips and basics.
103. Would you rather find out someone thinks about you while masturbating even though you don't find them attractive, or admit to someone that you think about them while masturbating?
104. Would you rather return a bottle of lube to the store, or have airport security hold up your sexy underwear in public?
105. Would you rather try a golden shower, or scat play?
106. Would you rather use flavored lube, or a warming/cooling sensation lube?
107. Would you rather get caught mid-sex by your parents, or by your partner's parents?

These dirty and playful would-you-rather questions set you up for a good time, whether you're texting or sitting face to face. With this much variety, you can replay the game again and again without it ever feeling stale — and you'll probably end up dreaming up plenty of your own spicy prompts too!

April 24, 2024