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Sex Questions & My Two Cents On 69 Of Them

by Robyn


I came across this “List of Dirty Questions to Ask Your Partner” in an online article. Obviously, stuff like this immediately grabs my attention. However, as I read through them, I found some of the questions … well … let’s say they could use some tweaking or deeper nuances.

And, it’s not just this one list. I’ve noticed many similar articles with similar questions.

Here’s one of them … but with my own two cents added.

What’s your dirtiest sexual fantasy?

First, as great as this question is, it’s not something you would ask someone you’re just getting to know. So, even though I would totally ask this, I would have divided this list into two groups

  • GREEN (Just fun. Or necessary if you’re going to be intimate)
  • YELLOW (Needs more trust or a sensitive topic)

It also comes down to the dynamic of the two (or more people). If it’s a drinking game among friends, someone trying to get to know a partner/lover better, or if you’re talking to someone more sexually open – this might change the color coding.

FOR EXAMPLE: I’m more open about my sex life, and someone new could ask me many of the “yellow coded” questions and I wouldn’t be phased. Then again, if some stranger approached me in a club and jumped right in with, “Hi, what’s your favorite sex position?” I might be put off.

69 Sex Questions I Found Across The Internet

  1. How many people have you slept with? I don’t like the wording. Too early and it feels like an interrogation question. It’s also something that might bring out insecurities. A better way to ask without being intrusive is, “How do you feel about your sexual experience?”
  2. Where’s the weirdest place you’ve had sex? Fun and a good lead into more communication.
  3. What’s your favorite part of my body? Yep. Good – complimentary.
  4. Have you ever had anal sex? Important to ask, because anal sex is something not everyone can jump into. It might be more delicate if it’s a woman asking a guy. But still, a great question.
  5. If you could choose what I was wearing right now, what would you choose? Hmmm, I think I would re-word this to something like, “What sexy clothing would you imagine me in?”
  6. Where on your body is your favorite place to be touched? Yep. Love it.
  7. When was the last time you had a dirty dream? Sure. Can be fun. But not everyone remembers dreams that well. You could adapt it to, “What’s the dirtiest dream you’ve ever had?” – Which is not the same as a fantasy, FYI.
  8. If you could have sex anywhere in the world, where would it be? I like this one. So much to talk about, and details that reveal the deeper part of someone.
  9. When did you first have sex? Fair question.
  10. What’s the best sex you’ve ever had? I would answer this with details of the act. Not who was doing it. Don’t risk it becoming a competition. Someone might not want to hear about how amazing your ex was in bed.
  11. What’s your favorite position? Yep, standard question everyone should ask. Especially if a quick hookup might happen.
  12. Have you ever been caught having sex? Could be an interesting conversation.
  13. Do you watch porn? Some people are sensitive about porn. Know what waters you’re about to swim into.
  14. What kind of porn do you watch? A fair follow-up question if the person answer is comfortable talking about it.
  15. How often do you masturbate? Might be personal for some people. Wait to ask this when it’s appropriate.
sex questions
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  1. Name a sex position you’d like to try. I’m on the fence about this. It could go either way. If you’re looking for new experiences, it’s a good discussion to get into.
  2. Do you prefer to give or receive? Needs to be asked if you’re going to play – doesn’t matter if gay, or pegging, etc.
  3. What was your best orgasm ever? If it is the orgasm and how it can be achieved again, cool. Not who gave it to you.
  4. Have you ever been skinny dipping? Sure, it’s a fun question. Mild enough to know if someone is a little adventurous.
  5. Have you ever slept with someone you work with? This gets more personal. It also feels I don’t know… weird? Don’t ask this WHILE at work ahahahah.
  6. If we were out for dinner and I said I wanted to have sex right now, what would you do? Can be HOT, if you know the person better.
  7. Have you ever sent nudes of yourself? As long as you’re not asking for nudes right off the bat.
  8. If you could sleep with any celebrity, who would it be? Totally okay to ask. It’s a fun question.
  9. Would you/have you had group sex? Definitely save this for when you know someone at least a little better. Also if you’re asking this in a kink club vs on a first date… well, you get the idea.
  10. What’s the most sex you’ve had in a day? This is similar to a libido question on this list. No harm in asking, but it gets into the grey areas of personal topics.
  11. Are you loud or quiet during sex? Might be important to know if you’re taking someone back to your place and your neighbors are nosy… or assholes.
  12. Have you ever tried using food during foreplay? Sure. I can get down with this. Harmless enough.
  13. Have you ever made a sex video? Yeah, this is getting into the personal side of things. Not to mention there’s the anxiety and fear around having that kind of media leaked – accidentally or not.
  14. What’s the first thing that sexually attracts you to someone? No harm in asking this. Anyone will have something that strikes their fancy.
  15. Would you say you have any fetishes? Some people have them but are too ashamed or not ready to even share the truth with themselves, let alone another person. Handle this situation with care.
sex questions
Credit Pexels
  1. When it comes to BDSM, how far have you gone/would go? My problem with this question is that BDSM is such a LARGE topic and cluster of practices, that it’s hard to answer in general terms. It’s like asking “How far have you gone in sports?” it can be answered, but I would have to get into the specific sport.
  2. What’s your favorite toy? Easy to answer and lots of follow-up questions that are equally interesting. But make sure you’re/they’re not insecure/shy about sex toys in the first place.
  3. Do you ever read erotic fiction? A good way to test the waters or have a warm-up question.
  4. Have you joined the mile-high club? Again, getting personal – which there’s nothing wrong with, but since it involves details about another person, best wait to ask this later.
  5. Do you think you could take off my underwear with no hands? Yes. I mean, if the flirtation is getting heavy, sure. But it’s not something to ask immediately.
  6. Would you say you’re kinky? This is a better way to get into a kinky conversation than some of the other questions.
  7. Do you enjoy shower sex? Good to know. It’s also safer than sex in water.
  8. Where’s the weirdest place you’ve ever masturbated? The definition of weird changes from person to person. Just don’t be judgmental about the answer, since you’ve asked that question. Maybe use the word adventurous, interesting, hottest, etc.
  9. Do you like to be spanked? Another one I’m on the fence about. If it’s already established the person is a kinkster or open, it’s safe to ask earlier on.
  10. What was your most embarrassing sexual experience? This can be very personal, even painful. Be careful.
  11. Have you ever fantasized about someone else during sex? Depending on who is in the conversation, this could be taken as a fun question or something intrusive.
  12. If I ever caught you masturbating, would you stop or would you finish? I don’t like the word “caught” because it makes it sound like what you’re doing is wrong. I would reword it to “If I walked in on you…”, then that could be interesting.
  13. Have you ever had an inappropriate crush? It depends on how someone interprets “inappropriate”.
  14. Have you ever cried or fallen asleep during sex? Errr. Yes, you can have sex so good, you cry. Or have had so much sex that you pass out. But these emotions can also be from bad experiences.
  15. Do you prefer eye contact or not during sex? A good thing to know.
sex questions
Credit Pexels
  1. Do you like to kiss during sex? Also important to know.
  2. Do you get tired after sex? I would say this is good to ask. Some people are just hit so hard with the post-sex sleepies that they just can’t help but fall asleep. Good for the other person to know so it’s not taken personally.
  3. How many positions do you think you’ve tried? Grey area. As long as it’s to search for new positions or be adventurous, it’s okay.
  4. What’s the longest you’ve ever gone without sex? This could be attached to a bad time in someone’s life. Handle with care.
  5. How high is your sex drive? This might be important for some to know sexual compatibility.
  6. What’s a sure-fire way to turn you on? Yes, please.
  7. Sex with lights on or lights off? Sure, why not.
  8. Do you like dirty talk? Yes, you need to know this. Because being called a “dirty whore” in the middle of sex could have wonderful or terrible consequences. Don’t forget to ask follow-up questions.
  9. Have you had sex in a car? Speaks to adventure. I can dig it.
  10. Do you prefer to take control or be submissive? If you’re kinky or exploring kink, it’s a good question to ask.
  11. Do you prefer one night stands or long-term sexual partners?
  12. Yeah, this is definitely on the personal side. It’s not a BAD question, just not a first-date question.
  13. Do you prefer to be on top or bottom? It’s not just about the power dynamics of sex. It could be attached to physical issues that are important to know so everyone has fun.
  14. What would you like to do more of in bed? Always good to know.
  15. What’s your favorite time of day to have sex? This might sound strange, but it’s important – not only for sexual compatibility but also schedules.
  16. Rough or romantic? Can’t it be both? Not everyone is static. People want different things at different times?
  17. Quickie or marathon session? Again. Why not both? Yes, people have preferences, and it’s good to find them out, but make sure to ask the right follow-up questions so you get to know the “why” better.
  18. What’s your favorite part of foreplay? Necessary. Do ask this. And give lots of it.
  19. Would you dress up for me in bed? Depends on the person’s comfort levels. You’re also asking for something directly just for YOU.
  20. What’s your favorite place to be kissed? Everywhere! I mean… good question.
  21. Do you like sexting? Also good to know. Someone might not be able to because of work etc.
  22. What’s the best thing about our sex life? A question you ask when you’ve been having sex for a while. Do ask this.
  23. What’s the shortest time it’s ever taken for you to have an orgasm? And the longest? Fun, but some women haven’t had an orgasm – or at least a significant one. Keep it lighthearted, unless you and the other person are trying to spice things up.
  24. How would you make me have an orgasm? I would reword this too, “Describe how/where/when you would love to make me orgasm.” Make it more of a fantasy or role-play than just the physical ending.

I bet, by now, you’ve thought (more than once), “No I wouldn’t ask that question so soon” or “What’s so bad about that question?” – I’ll say again, it totally depends on the circumstances of the conversation. Just use good judgment and know if you’re stepping over boundaries.

Are all these questions good? Yes. I’ve asked all of these, myself. Definitely use them and other examples from other lists – but don’t use it as a first date checklist, interrogation, etc.

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Any comments you have about these sex questions? Share in the comments!

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Tina Klaeger 06/19/2020 - 12:00 am

I am a 19-year-old woman and am submissive by nature. I prefer rough, marathon sessions of anal sex that last between 60 and 120 minutes. Pain doesn’t turn me on, but I am willing to endure substantial pain for an hour or two in order to maximize the pleasure of my boyfriend. He uses saliva as lube.


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