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115 Freaky Questions to Ask Your Boyfriend Over Text

Freaky questions to ask your boyfriend over text that will make your relationship more exciting and keep the sparks flying. Read more ⇣
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Written By Erica
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I'm Erica. I love to help people in their relationships and spiritual lives. I've been through a lot of ups and downs, and I want to share my insights with you.
Freaky questions to ask your boyfriend over text

If you’re in a relationship with a guy, then you know how important it is to ask flirty and sexual questions to ask your boyfriend over text. It’s one of the best ways to keep him interested in you.

Asking these kinds of questions will make him wonder what you’re up to, and it makes him think about what you’re going to do next

It’s also one of the easiest ways to keep yourself entertained when you’re bored or you need something fun to do.

Most importantly, it’s a fun way to keep the tension and desire alive, even when you’re not physically together. I’ve come up with 115 freaky questions to ask your boyfriend over text.

You should use this to keep things interesting and fun while texting one another.

You should also check out my list of dirty ’21 questions’ to ask your crush.

115 Freaky Questions to Ask Your Boyfriend Over Text

  1. What is the farthest you have gone on a first date?
  2. Where do you like to be kissed?
  3. Have you ever been attracted to a guy before; if yes, how did you feel?
  4. What is the craziest thing that you have done in your life?
  5. If I were there with you right now, what would you do to me?
  6. Have you ever done it in a public place?
  7. If you could only touch me in one place, where would it be?
  8. If we were in a movie theater, and I wanted to do it, what would you want me to do?
  9. Do you get turned on more in the morning or at night?
  10. Do you like talking dirty over text messages?
  11. Do you like it when I send you naughty pictures of myself?
  12. Touching myself while looking at your pictures is my favorite thing to do. Are you able to send me one right now?
  13. Is there anything you want to tell me about your dirty dreams?
  14. Is it more convenient to talk dirty on the phone or over Facetime?
  15. In regards to your love life, what is your freakiest fantasy?
  16. Do you enjoy it when a lady (like me?) massages your body?
  17. Is there anything you would like to do to me that is dirty?
  18. If I said I can’t avoid thinking of you at night when I can’t stand not touching myself? What would you think of that?
  19. Would you prefer to start with the upper or lower part of my body if we were lying in bed now? 
  20. I want you to rip my clothes off. What are your chances of doing that with your teeth? 
  21. Would you like to guess what color my new lingerie is? 
  22. If you were to bind me, would you prefer blindfolding me or tying me up?
  23. Could you imagine how you would feel if I served you breakfast by wearing nothing but an apron? We can test it out if you come over. 
  24. The part of my body that you like the most?
  25. When I аsk you to give me my full body massage, what part would you start with?
  26. Do you like dirty talk? What would be a good example for me?
  27. Do you like it when someone pulls your hair?
  28. Do you like the lights on or off during sex?
  29. What would you do if you could do anything with me?
  30. How does it feel when I go down on you?
  31. How do you want me to touch you? Describe it.
  32. Is there a sexy scene from a movie that you want to recreate with me?
  33. How can I drive you crazy with my body?
  34. Can you undress me with just your mouth?
  35. What is your favorite sort of foreplay?
  36. What is a sex position you have never tried, but would love to try? 
  37. Do you prefer rough or romantic? 
  38. What would you do if I answered the door without clothes on?
  39. Can I watch you pleasure yourself?
  40. Do you like getting tied up? How about tying me up?
  41. Do you like getting tied up? How about tying me up?
  42. What’s the dirtiest thing you’ve thought about doing to me?
  43. Who do you think of when you pleasure yourself?
  44. Would you rather see me in lingerie or nothing at all?
  45. Do you like me being possessive over you?
  46. Have you ever done it in the backseat?
  47. What is your favorite sex position?
  48. What object did your adult-ed teacher use to demonstrate how to put on protection?
  49. Under the sheets, are you Iron Man, The Hulk, Thor, or Captain America?
  50. How many rounds do you think you could go? What about on our wedding night?
  51. What’s the hottest thing you’ve done to someone else?
  52. Do you like going down on me?
  53. What’s the best bedroom experience that you’ve ever had?
  54. What’s your favorite position with me on top?
  55. What outfits turn you on the most that women wear?
  56. Have you ever stared at my butt or chest?
  57. What would you say or do if I sent you a dirty picture of me?
  58. Do you like experimenting with different positions, which is your favorite?
  59. What’s the most number of times you’ve done it in a row
  60. Would you rather see me in underclothes or nothing at all?
  61. Where would you like to get touched the most?
  62. How about recording a clip of us? Does the idea excite you?
  63. Do you want to have sex with me in a public place?
  64. Would you like to shower with me when we are together?
  65. Do you prefer to be in control or let me take charge sometimes in the bedroom?
  66. What would you do if I kissed you hard?
  67. How do you want a girl to seduce you?
  68. What are your thoughts on oral sex?
  69. What kind of adult films do you like to watch?
  70. Did you ever read erotic fiction?
  71. How kinky are you?
  72. Would you like me to spank you?
  73. What is the longest time you have ever taken for orgasm? And the shortest?
  74. What can I do to keep the feelings of being intimate going all day – outside of the bedroom?
  75. What is the hottest thing a lover can say in bed?
  76. Are you shy or outgoing, in the bedroom?
  77. If your body was a plant, how many times a day would I have to water it?
  78. Can you tell me if you think my bikini waxer did a good job?
  79. What porn are you watching right now?
  80. What do you look like, and sound like, when sex feels good for you?
  81. What would an erotic vacation look like for you?
  82. Is there a sexy song that tends to get you in the mood?
  83. Have you ever been caught having sex before? Tell me about it.
  84. What’s something you’ve always wanted to ask me to try—but assumed I wouldn’t like?
  85. Where’s the wildest place you’ve ever hooked up with someone before?
  86. Want to try making as much noise during sex as possible?
  87. Want to try sex as quietly as possible, as if we’re trying not to get caught?
  88. Can we spend a night devoted to your pleasure and what makes you feel good?
  89. Want to try using food as foreplay?
  90. Have you ever fantasized about someone else while having sex?
  91. What color underwear would you like to see me in later?
  92. Do you like playing music in the background or in silence?
  93. How many people have you had sex with?
  94. Do you remember the best orgasm you’ve ever had?
  95. Is spanking something you’d like to try with me?
  96. Which do you like more—sending dirty texts, or dirty talk in person?
  97. Have you ever thought about trying tantric sex?
  98. Have you ever been caught masturbating? How did it make you feel?
  99. Can you describe the last time you got turned on in public?
  100. What is the most amount of times you’ve had sex in a single day?
  101. Which would you like more—to be in control, or to be dominated?
  102. Would you rather have sex on a plane, or on a moving train?
  103. Would you rather have car sex or shower sex?
  104. What’s the most unusual place you’d like to have sex with me?
  105. Where’s somewhere in our home you’d like to ‘christen’ with sex?
  106. What would you like me to wear to bed tonight?
  107. Would you like to use one of these vibrators on me?
  108. Can we shop for sex toys together?
  109. I’m wearing vibrating panties right now—want to control the remote?
  110. Does the idea of partner-swapping make you feel jealous, turned on, or both?
  111. What would you like to watch me do to myself, sexually?
  112. What’s the dirtiest thing you’d like to hear me say during sex?
  113. Do I taste good?
  114. How does it feel when I touch you?
  115. What is the kindest thing you have ever done?


Are you looking to spice up your relationship by asking sexual questions? 

While it’s great to ask your boyfriend about his day, you can also use these questions to find out his experiences and thoughts on sex as a whole.

Next time you are texting him, try out these flirty, sexy, naughty, and freaky questions to ask your boyfriend.

I’m sure this is guaranteed to increase his desire for you in the sheets!

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