Looking for a fun new way to turn a guy on? Asking him dirty, flirty questions will get his mind racing with thoughts of only you.
Think of it as a naughty game of 20 questions. Not sure what to ask? Here are 100+ questions to help you get started.
The Exclusive “List of Naughtiness”
1. “Do you like talking dirty?” – Find out if he even likes talking dirty before you start asking naughty questions.
2. “Do you like to check me out as I walk by?” – This question will get him thinking about you (or your backside).
3. “What are you wearing right now?” – Follow up by telling him what you’re wearing. Be detailed!
4. “What part of a woman’s body do you love the most?” – His answer will tell you which parts of your body you should flaunt.
5. “What’s your dirtiest sexual fantasy?” – Find out what his fantasies are, so you can make them come true.
6. “Where do you like to be touched?” – Find out where his pleasure points are to heat things really up in the bedroom.
7. “What part of my body do you like kissing the most?” – This question will get him thinking about you in a naughty way.
8. “Have you ever had phone sex?” – If he’s had phone sex and liked it, maybe he’d be open to trying it again and with you.
9. “Where’s the craziest place you’ve had sex?” – His answer will let you know how adventurous – or unadventurous – he is.
10. “What’s your favorite position?” – This question will get him thinking about sex and will give you the opportunity to try out his favorite position.
11. “What should a woman wear to bed?” – Learn what his tastes are.
12. “Can you guess what color panties I’m wearing right now?” – A naughty question to get him thinking about you in a dirty way.
13. “Have you ever had a threesome? Would you want to have one?” – Another question that will give you a peek at his sexual fantasies, and if he’s open to new ideas.
14. “Have you ever gone skinny dipping?” – If not, maybe he’d like to try it with you.
15. “Have you ever been caught having sex? Did that person join in?” – His answer will tell you if he’s private or open about his sex life.
16. “What would you do to me if I was with you right now?” – A good icebreaker to get him to start talking dirty.
17. “Are you a good kisser? Care to demonstrate your skills?” – A naughty question to help get the action started.
18. “Have you ever used sex toys in bed?” – Find out if he’s kinky, and just how kinky he is.
19. “Have you ever had sex that was so good you woke the neighbors?” – His answer will reveal whether he’s wild in bed, or shy and reserved.
20. “What was your first time like? Was it with someone special?” – Sharing his “first-time” experience will help you get to know him better.
21. “Have you ever had a one night stand? Would you ever do it again?” – Is he a player? Or, has he only had a few one-night stands?
22. “What kind of foreplay do you love?” – Learn what foreplay moves turn him on the most, and start doing them more often.
23. “Do you think you can please a woman? Care to prove yourself right?” – This isn’t a question; it’s more of a challenge. See if he can live up to his claims!
24. “If you could have sex anywhere in the world, where would you choose?” – Find out if he’s a romantic, adventurous, or just enjoys simple love-making.
25. “Do you like being dominated in bed, or do you like taking the lead?” – If he likes being dominated, maybe it’s time for you to take the lead.
26. “If you were a magician, what piece of my clothing would you make disappear? Why?” – His answer will tell you what part of your body he likes the most.
27. “If we were in the same room right now, how long would it take for you to strip me naked?” – Another challenge question!
28. “Do you like making love with the lights on or off?” – Learn what his sexual preferences are.
29. “What type of role-playing turns you on the most?” – If you’re open to the idea, make his role playing fantasies come true.
30. “Have you ever had sex in a public place? Did you get caught?” – His answer will tell you how adventurous he is in the bedroom, and how he reacts in sticky situations.
31. “How long will it take you to get here?” – Let him know you want him – right now!
32. “What makes a woman sexy in your eyes?” – Does he love a woman’s mind or a physical feature?
33. “What’s the difference between making love and having sex? Which would we be doing?” – Find out what he defines as “making love,” and where the two of you stand.
34. “Have you ever been seduced by an older women? How old were you? How old was she?” – His answer will give you a look at his past sexual escapades.
35. “How old were you when you had sex for the first time? Do you wish you would have had sex earlier or later?” – Get to know him a little better, and find out when his sex life began.
36. “What kind of outfit do you like seeing me in?” – Know what he likes, and wear his favorite outfit the next time you see him.
37. “Have you ever had anal sex? Did you like it?” – Another question to help you learn more about his sexual tastes.
38. “What would you do if you caught me making out with a really hot girl?” – Would he be open to a threesome, or get angry at the sight?
39. “What would we do if we were caught in a rain storm and got soaking wet?” – Let his mind race with thoughts of the two of you making love in the rain.
40. “If you could kiss me anywhere, where would you choose?” – What part of your body does he love to kiss and touch?
41. “Have you ever bought sexy lingerie for a woman? Did she like what you picked out?” – His answer will tell you if he pampers or spoils the woman he’s with.
42. “Have you ever sexted? Would you like to try it?” – Invite him to try sexting with you.
43. “Have you ever gotten a massage from a woman? What part did you like the most?” – Invoke erotic thoughts and learn where his erogenous zones are.
44. “Of all the naughty things we’ve done in the bedroom, which one was your favorite?” – Get him thinking about your sexual encounters.
45. “If we were both horny in a public place, what would you do? Would you have sex with me in public?” – Gauge how adventurous he can be.
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46. “What do you wear to bed at night? What would you like me to wear?” – Does he sleep naked, or in pajamas?
47. “How old were you when you had your first kiss? Who was it with?” – Learn more about his past and his first romantic encounters.
48. “What part of my body do you think a tattoo would look best on?” – A question that will get him thinking about your body.
49. “What’s the sexiest thing you’ve ever texted to a woman?” – Find out how naughty he can be, and if he likes dirty texting.
50. “Has anyone ever accidentally walked in on you while you were naked?” – If so, how did he react?
51. “Would you rather watch a couple have sex, or have someone watch you while having sex?” – This question is an easy way to find out if your partner is an exhibitionist or a voyeur.
52. “Would you rather blindfold me, or be blindfolded?” – His answer will let you know if he needs to be in control, or can let go during sex.
53. “Do you prefer romantic sex, or something a bit kinkier?” – Or something in between?
54. “Which is better: having an orgasm during sex, or oral?” – This question will let you know how important oral sex is to him.
55. “What was your naughtiest sexual fantasy in high school?” – This question will let him reveal even his most bizarre sexual fantasies without feeling awkward.
56. “Would you rather go down on a woman, or have a woman go down on you?” – His answer will tell you just how important it is for him to please his woman.
57. “Does it intimidate you when a woman makes the first move?” – If his answer is yes, now would be a good time to make your move.
58. “What’s your idea of the perfect kiss?” – Let him show you – not tell you.
59. “Which of my features do you like the most?” – You’re not fishing for compliments here. You’re trying to get him to think about that favorite part.
60. “Have you ever sent a naked photo of yourself to someone?” – His answer will tell you how adventurous he is, or if he prefers to keep intimate moments private.
61. “Have you ever had cybersex?” – If he has, maybe he’d be open to trying it with you.
62. “Do you like quickies?” – His answer will tell you if he prefers longer, intimate love making, or a good, quick romp.
63. “Where’s your favorite place to have sex?” – Is he adventurous, or does her prefer to make love at home in the bedroom?
64. “If I allowed you to, which of my friends would you have sex with?” – Be careful with this question – he might see it as a trap. But his answer will give you an idea of what his “type” is.
65. “If you could have sex with any porn star, who would you choose?” – The woman (or man) he picks will tell you what his “type” is, and what type of porn he likes to watch.
66. “Have you ever had an orgy? If so, how many women did you have sex with?” – This question will give you an idea of what his sexual fantasies are.
67. “Have you ever had sex with two women on the same day? Did they know about each other?” – Find out if he’s a player, or if he prefers monogamy.
68. “What’s the highest number of sexual positions you tried in one session?” – Does he like trying new positions, or does he prefer to keep things simple?
69. “Have you ever watched porn to get yourself off?” – You know the answer, but the question will get him thinking about sex.
70. “Do you sleep after sex, or are you ready to go right away?” – His answer will tell you how big or small his sexual appetite is.
71. “What turns you on instantly?” – Learn more about what turns him on to make sex more pleasurable for him.
72. “Which celebrity do you think would give the best BJ? Why?” – Get him thinking about oral sex, and his sexual fantasies.
73. “What’s the craziest sexual position you’ve ever tried? The butter churner? The wheelbarrow? Missionary?” – Find out how boring or fun he is in the bedroom.
74. “What’s the kinkiest thing your partner has asked you to do? Did you do it?” – What kind of women has he dated or slept with in the past? Is he open to bizarre sexual fantasies?
75. “Do you like to talk dirty during sex?” – Or, is he a bit prude?
76. “Do you like it when I moan during sex?” – You know his answer will be “yes,” but your question will make him think about you moaning – and sex.
77. “Do you ever fantasize about what you want to do to me? Care to give a demonstration?” – Get him thinking about his fantasies about you, and invite him to play them out.
78. “What flavor lip gloss do you like best on a woman?” – This question will get him thinking about your lips.
79. “Do you prefer passionate kisses, peck kisses, or none at all during sex?” – His answer will tell you how passionate he is (or isn’t) during sex.
80. “What’s your favorite type of lingerie?” – His answer will tell you what type of lingerie to wear in bed.
81. “What turns you off?” – His answer will tell you what not to do in the bedroom.
82. “What is your idea of the perfect sex?” – What type of sex does he prefer? Something intimate or wild?
83. “Have you ever had sex with someone, and regretted it the next morning? Why?” – Does he make poor sexual decisions?
84. “Have you ever cheated on an ex? Did she ever find out about it?” – His answer will let you know whether you should keep it casual, or get serious.
85. “What’s one thing you want me to do more of in bed?” – Find out what he loves about having sex with you.
86. “What’s the dirtiest thing a woman has ever said to you?” – Get him thinking dirty thoughts.
87. “What’s one fantasy you’re too shy to share?” – Find out what his deepest, darkest fantasies are.
88. “Have you ever experimented with someone of the same sex?” – Be careful with this question – he may get offended.
89. “If anyone in this room could be a sex slave, who would it be? What would you have them do?” – Get to know the kinkier side of him.
90. “What do you fantasize about when you’re having sex?” – His answer might clue into fantasies that are unfulfilled.
91. “Have you ever had sex at the office? Was it after-hours, or while everyone was there?” – Is he a thrill seeker?
92. “Can I go down on you right now?” – Cut to the chase, and get down to it.
93. “Tell me one dirty thing you’ve always wanted to say to me in bed?” – Get him thinking about that one dirty thing.
94. “Do you like it better when I undress you, or when you undress yourself?” – This question will get him thinking about you taking his clothes off.
95. “What’s one place you’ve always wanted to have sex, but were too scared to?” – Maybe the two of you can conquer his fear together.
96. “What’s the most memorable sexual experience you’ve had?” – Maybe you can relive that sexual moment he treasures.
97. “What do you think of me sexually?” – Does he see you as a sex goddess, or the girl next door?
98. “If I could do anything to you, what would you have me do?” – This question will definitely get him in the mood.
99. “What sexual thing do you love most?” – Does he love anal, oral, intercourse, or all three?
100. “What’s the weirdest sexual thing you’ve ever done?” – Get to know his kinky side.
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Check out this great article from TheStallionStyle for more ideas for questions to ask your boyfriend. I know this resource will help you.