Dating Tips

Introduction to Sexual Questions to Ask a Boy

Now is the best time to grab your guy and ask sexual questions. Finding out more about what to expect from him in bed is easy. Don't hesitate to discover his dirty secrets with our list of hot questions to ask a boy.

Drop your inhibitions and get to know his deepest desires and hottest sexual fantasies. Ask detailed questions that will get him turned on. Boys like girls who make the first move because they are a huge turn-on.

Reading books about male sexuality is a thing of the past as boys nowadays are willing to share what they like in person. Sit him down for a drink and ask sexual questions at your leisure. More than 70% of men admitted that they find it hot when women inquire about this topic.

Enjoy a hot conversation with plenty of flirting. Traditional ways of getting to know each other are not as popular as they used to be. While some may ask their partners about pets and parents, you can set yourself apart from the crowd and ask your boy about something sexual and daring.

It's best to avoid cliche questions since your boy has heard them before, and it's unlikely he'd want you to ask them. Wait until you feel comfortable and confident to start the conversation. Hit him with something he doesn't expect from the list of sexual conversation prompts, thus ensuring he remembers you next time a kinky thought crosses his mind.

Find Out What He Likes With Interesting Sexuality Questions

girl asks a boy sexual questions

Are you wondering how to find out what your boy thinks about intimacy and its role in a relationship? The good idea is to ask probing questions to dig into his sexual preferences and things that make him feel horny. After all, if you ask the dirtiest questions, you will have the most enjoyable time. Here are some of them:

  1. When did you lose your virginity?
  2. Who was your first crush?
  3. Do you have a lot of experience with sex?
  4. When did you have your first sexual fantasy?
  5. Who was the first girl you remember wanting to sleep with?
  6. What is your favorite sexual position?
  7. When was the last time you learned a new sexual position?
  8. When did you first flirt with a girl?
  9. What is your deepest sexual fantasy?
  10. Do you prefer to take the lead in bed?
  11. How often do you have sexual dreams?
  12. Have you ever had a dream about me?
  13. What was the hottest dream you have ever had?
  14. Are you into butts or boobs?
  15. How much foreplay is enough for you?
  16. What do you think drives girls crazy sexually?
  17. Do you have a go-to move in the bedroom?
  18. When was the first time you were sure you gave a girl an orgasm?
  19. How many girls have you had sex with?
  20. What do you think about a friends-with-benefits-style relationship?
  21. What is the one thing that a girl can do in bed that will drive you wild?
  22. Do you like cuddling?
  23. What was your first steamy make-out session like?
  24. What is completely off-limits for you in bed?
  25. What was one thing that a girl did during sex that completely turned you off?
  26. Do you really care if women aren't completely shaved?
  27. What was the best sex you have ever had like?
  28. Was there any scene in a movie you were embarrassed to watch with your parents?
  29. Who was the first Hollywood star you found sexually attractive?
  30. If you could sleep with any famous person, who would it be?
  31. What is your opinion on dirty texts?
  32. What would you think if I sent you a naughty photo?
  33. When was your best sexual performance?
  34. Have you ever been asked to make a sex tape?
  35. Have you ever had sex in a public place?
  36. Have you ever watched someone have sex?
  37. What's your favorite kind of porn?
  38. Do you prefer knee socks or thigh-highs?
  39. What do you think is the most important thing for a girl to know how to do in bed?
  40. Do you like 69?
  41. Do you prefer to give or receive oral pleasure?
  42. Have you ever regretted having a one-night stand?
  43. How many one-night stands have you had so far?
  44. What is your opinion about casual hookups and relationships?
  45. What is the most attractive thing a girl can do in public to make you want to sleep with her?
  46. How many times have you slept with someone on the first date?
  47. What was the most daring place you've ever had sex in?
  48. Has anyone ever caught you masturbating?
  49. What do you think about when you masturbate?
  50. What is the naughtiest fantasy you have about me?

If you're feeling shy, feel free to send a sexual text to your boy. Surely, he will be happy to answer any of your questions.

Sexual Questions to Ask a Boy You Like

photo of couple gossiping sexually

You might think that making the first move is awkward; however, it's not true. It's been observed that girls who initiate sexual talks are much luckier in love affairs than ones who don't. Try out the nasty questions to ask a boy mentioned below to break the ice and up your flirting game.

  1. What kind of flirting drives you crazy?
  2. What is the hottest thing someone has ever whispered in your ear?
  3. Would you rather see me in a sundress or tight jeans?
  4. What's your favorite part of a girl's body?
  5. Can you tie a cherry stem with your tongue?
  6. What non-sexual thing do you find incredibly sexy?
  7. Do you find smart girls hot?
  8. Do you prefer someone who challenges or supports you?
  9. What do you think is my favorite part of a male body?
  10. Do you find shyness hot, or do you prefer daring women?
  11. What would you say if someone kissed you out of the blue?
  12. What do you think about the dirty talk?
  13. What is the most memorable quickie you've ever had?
  14. Have you ever been caught doing the deed?
  15. Have you ever caught someone having sex?
  16. Do you find girls who do cosplay hot?
  17. What hair color do you think is sexiest on a woman?
  18. Have you ever had an orgasm while sexting?
  19. Have you ever spanked someone?
  20. What's your favorite line a girl has used on you?
  21. How many times has a girl made the first move on you?
  22. Do you think kissing is important when you're sleeping with someone?
  23. What's the longest you've ever gone without having sex?
  24. Do you care about how many times you've got laid?
  25. Do you think kissing another girl or boy is cheating?
  26. On a scale from 1 to 10, how attractive do you think you are?
  27. Have you ever had an erection in public?
  28. Do you wish your first time was different?
  29. Do you think flexible girls are better in bed?
  30. Has anyone ever done a striptease for you?
  31. Do you find girls who know how to dance sexy?
  32. Have you ever been with a bisexual girl?
  33. What fantasies have you lived out in real life?
  34. Have you ever paid for sex?
  35. What is the worst thing a girl has done to you in bed?
  36. Have you ever had phone sex?
  37. Did you ever have a long-distance relationship?
  38. How often do you like to have sex?

The 21 Questions Game to Ask a Guy — Dirty Version

couple sitting in cafe talking and initiating sexual talks

21 questions is a great game to play to get closer to your boy. Typically, the game is played by taking turns asking important questions about each other's views on life and the past. Give it a naughty spin, and find out every dirty thought your boy has. Feel free to use our questions to ask a boy and turn him on.

  1. Could you tell me about your hottest fantasy in detail?
  2. If you had to choose to have sex in only one position for the rest of your life, which would it be?
  3. Have you ever thought about hooking up with a same-sex partner?
  4. If you were given the choice to be with a girl who didn't need foreplay, would you be happy or disappointed?
  5. What are the top three spots where you like to be kissed?
  6. What sort of naked photo would you like to receive from me?
  7. What was the first non-pornographic movie scene that you watched that turned you on?
  8. What female superhero do you think would be the most interesting to hook up with and why?
  9. What superpower do you think would be best to have for sex?
  10. Do you think women who like to talk dirty are vulgar or hot?
  11. Do you prefer to take an active role or a passive one when you're hooking up with someone?
  12. If you had a choice between tying someone down or being tied down, what would you pick?
  13. If you were to do a kinky roleplay with a girl, what would be your role?
  14. Would you like to see me in white baby-doll lingerie or dressed in latex and leather?
  15. What is the one thing that a woman can do to make you orgasm in minutes?
  16. Have you ever fantasized about any of your friends when pleasuring yourself?
  17. If given a choice, would you like to get a week of blowjobs or one threesome?
  18. Did you ever have nasty thoughts about any of your friends' moms?
  19. Have you ever been to a strip club? What was it like?
  20. If you had to choose between never giving and never receiving oral again, which would you choose?
  21. What would be the most erotically creative thing a girl could do in the bedroom with you?

And there you have it! Using any of these sexy questions to ask a boy will guarantee that he'll be thinking about you for weeks to come.