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400+ Dirty questions to ask a guy to strike some naughty conversations.

400+ Dirty questions to ask a guy to strike some naughty conversations.

Updated on Sep 22, 2022 | Published on Nov 16, 2021

Reviewed by Julianne Cantarella, MSW, LSW , Certified Relationship Coach

400+ Dirty Questions to Ask a Guy to Strike Naughty Conversations

So, you are here looking for dirty questions to ask a guy.

Honestly, you’re not alone. There are so many more like you.

It is not a surprise that most women want to talk about sexual desires openly without making it too obvious to their partners.

Plus, it’s so much fun (read: kinky fun) to have an intimate conversation with your partner about these topics.

But have you wondered what questions you should ask? Or how to start a dirty conversation and make sure it continues smoothly? I am sure you have.

That’s why you are here.

…and that’s why I have compiled a list of 400+ dirty questions to ask a guy.

You’ll find all the dirty and witty questions here, to relish in some kinky fun with your guy. Brownie points, if you have some wine handy! 😉

So, whether you are shy or extroverted, I’m sure you still want to indulge in an intimate conversation with a guy you are exploring.

To start a dirty conversation, it’s always good to play subtle and ask some personal questions before going into the hot stuff.

400+ Dirty Questions to Ask a Guy to Strike Naughty Conversations
400+ Dirty Questions to Ask a Guy to Strike Naughty Conversations

Personal dirty questions to ask a guy

If you know the guy sitting opposite to you on a personal level but haven’t explored his “dirty” depths. Now is the time for you.

Let’s begin!

  1. What turns you on the most?
  2. What color of lingerie do you generally like?
  3. Do you like to explore things in the bedroom?
  4. Will you approve of a one-night stand?
  5. According to you, what physical features of a woman make her irresistible?
  6. What can be the biggest turn-off for you?
  7. What was your age when you started dating?
  8. What is the one place you like to kiss your woman the most?
  9. What is the perfect way to end a love-making session?
  10. Do you think “size” matters?
  11. What was your age when you first masturbated?
  12. Do naked pictures of a woman excite you?
  13. Have you ever gotten horny in a public place?
  14. Did you ever fantasize about your female friends?
  15. Have you ever made out with anyone in public?
  16. Did you ever receive a dirty text from an unexpected person?
  17. Are you a boob or butt guy?
  18. What part of a woman’s face do you like to kiss?
  19. Do you believe in love at first sight?
  20. Do you find women older than you attractive?

Now that you are comfortable talking about this topic with a guy… let’s up your flirting game with some dirty questions.

Don’t forget to see the sly smiles on his face! 😉

Dirty flirty questions to ask a guy

I hope you’ve already had a taste of a “dirty” conversation. Well, obviously you can’t get dirty without being flirty!

Flirting is such an exciting task, especially when you are just getting to know the guy. Keep that adrenaline rush alive and uncover some flirty truths throughout the conversation.

  1. When was the first time you watched a blue film?
  2. Have you ever been physically attracted to any of your cousins?
  3. Have you ever made out when you were extremely drunk?
  4. Did you ever hit on your friend’s girlfriend?
  5. What part of my body attracts you the most?
  6. What should a girl wear to get you horny?
  7. Have you ever done it in an elevator?
  8. Did you ever jerk off seeing somebody’s picture online?
  9. Have you ever asked someone to send you a nude picture of hers?
  10. Do you like moaning during sex?
  11. What would you do to hint to me that you want sex?
  12. Do you enjoy neck kisses?
  13. Do you like roleplay to set a different mood?
  14. Would you love to get a lap dance?
  15. Do you like it when you are held by your neck while making out?
  16. Have you ever been friends with benefits with anyone?
  17. Have you ever secretly watched someone taking a shower or changing her clothes?
  18. When was the first time you saw a naked woman?
  19. Do you ever fantasize about doing it with a celebrity?
  20. Do you check out random women passing you by?

It’s definitely getting hot in here with all the chemistry between you and your guy, but do you know their sexual desires yet. No? Good, that we got you covered.

Sexual questions to ask a guy

Well, sexual desires are not something you can know out of thin air, right? It takes time to know a guy let alone knowing their sexual desire.

And what if the guy is shy or he doesn’t like it?

Do not worry, we are here to save you from all those hours of overthinking.

  1. How do you want me to seduce you?
  2. Does taking your name during sex turns you on?
  3. What part of your body immediately turns you on if a woman touches it?
  4. Have you ever secretly watched someone while they were doing it?
  5. Have you ever taken a shower together with your partner?
  6. What is the best color of lingerie one can wear to immediately turn you on?
  7. Would you drink alcohol from your partner’s mouth?
  8. Do guys like it when women make the first move?
  9. Does sexual experience matter?
  10. Would you love to see your partner in edible underwear?
  11. Have you ever had love at first sight?
  12. Would you sleep with someone 10 years younger than you?
  13. Do you like to choke your partner while doing it?
  14. Do you like to stay on top or keep the opposite gender on top?
  15. Have you ever grabbed your partner’s private parts in a public place?
  16. Do you feel good if a woman touches you down there?
  17. Have you ever tried making out in a classroom?
  18. Have you ever had a dirty dream of someone close to you?
  19. Do you like to look at your partner while you are doing it?
  20. Do you love to take off clothes yourself or let your girl do it?

I know, it is not enough! But honestly, are sexual desires ever enough?

Keep exploring and you’ll soon find out… he is a damn freak! 😉

Well, want to know how much of a freak your man is from the inside? These questions will give you in-depth answers to that. If you know, you know.

Freaky Questions to ask a guy

Let’s be honest, you can never spot the freakiness behind that super-cute innocent face. Can you? It’s only under the sheets you know that your partner is super-adventurous even in bed!

So, keep the conversation flowing and ask some heated questions to discover his freak side.

  1. Do you like to go down or want your woman to go down on you?
  2. Do you like it when your woman moans more?
  3. Do you like to pull hairs while making out?
  4. Do you like to tear my clothes off while making love?
  5. Do you like to go rough with your partner?
  6. Are you experimental with different sex positions?
  7. What is your opinion on a threesome?
  8. Do you like to bite on breasts?
  9. Do you like this number, I meant 69?
  10. Do you like to be seduced by dirty dancing?
  11. Have you ever been in a tub with your opposite gender?
  12. Does putting a thumb inside the lips excite you?
  13. Do you like tying up your partner during sex?
  14. Have you ever tried to use lubricants while having sex?
  15. Would you do it in front of a mirror?
  16. Have you ever made your partner horny in a public place?
  17. Would you ever do it in a car?
  18. Do you like it slow or fast?
  19. Does it turn you on if your partner is in wet clothes?
  20. What color underwear should a woman wear to bed?

Now, it’s time to crank the heat, ladies. And also add some fun to it.

Funny sexual questions to ask a guy

Apart from the fun, did you know laughter can also help you connect with him on a deeper level? Well, now you do.

And why not… I’m sure both of you must’ve had some really funny sexual experiences or desires that we are just too shy to share with anyone else.

Let’s lighten the mood with some funny questions to ask a guy that I’ve compiled for you in the list below.

P.S. For enhanced benefits, play this section as an after-play. 😉

  1. Would you have sex with a woman if she didn’t shave?
  2. What is the weirdest thing you want to pour on your partner’s body?
  3. Have your female friends ever caught you with a hard-on?
  4. Have you ever clicked nude photos of yourself?
  5. Do you get turned on if you see a woman eating something in a sexual way?
  6. Did you ever send a dirty text to your mom/dad by mistake?
  7. Have you ever caught random strangers making out in public?
  8. What was your weirdest sexual experience?
  9. What is the easiest item of clothing to remove from the body?
  10. Did you ever walk in while couples were doing it?
  11. Have you ever masturbated in a public washroom?
  12. Have you ever been sexually attracted to anime characters?
  13. Have you ever farted while doing it?
  14. Has anyone ever caught you while you were masturbating?
  15. Have you ever found your friend’s sister hot?
  16. Have you ever tried to do a new position but ended up laughing because it was too hard?
  17. Have you ever tried to talk dirty but instead it turned out to be embarrassing?
  18. Have you ever practiced kissing in a mirror?
  19. Have you ever wanted to do it with your neighbor?
  20. Have you ever created a page on social media to sext with anyone anonymously?

Most of us can ask fun dirty questions and strike a conversation. But to keep him hooked while you are at it is the real deal.

Let’s see how you can do that.

Interesting dirty questions to ask a guy

A conversation about sex is always exciting. But it can turn boring very fast if you fail to communicate the desire that you REALLY want to know more about him.

So, take some help from this list of interesting questions to ask a guy and make sure he feels heard.

Maybe you will be able to find a hidden sexual desire he didn’t even know he had.

  1. Do you like to smell your partner while having sex?
  2. Do you like to know your partner before having sex with them?
  3. Would you buy lingerie for your partner?
  4. Would you love to lick off chocolate from your partner’s body?
  5. What is the most nonsexual thing in a woman that turns you on?
  6. Do you like to talk to your partner after having sex?
  7. Is laughing in the bedroom during sex, inappropriate?
  8. 108. What is the one place on your bucket list where you want to do it?
  9. If you could have “it” in only one position for the rest of your life, what would it be?
  10. Would you have sex with a woman 2 times your age?
  11. Would you continue to kiss your partner if she says no?
  12. Would you love to do it in places besides your bedroom?
  13. Would you have sex only because your partner wants it?
  14. Would you do it if your partner is on her period?
  15. Have you ever tried to act like a fictional character inside the bedroom?
  16. Have you ever licked peanut butter from your partner’s body?
  17. Have you played sex games in the bedroom?
  18. Have you accidentally touched a stranger’s body parts around people?
  19. Have you ever sent a dirty text to your partner in front of family members?
  20. Have you tickled your partner during sex?

Isn’t it amazing when a guy really wants to talk to you?

But that was too much talk… with such a long list of deep questions to ask a guy.

Let’s get a bit, (actually a lot) erotic and find out all that he has in mind for your bed-times! 😉

Erotic questions to ask a guy

I told you, you are in for a long ride.

I would never want things to end between you and the guy when you are hot and bothered. Instead, it’s time to ramp it up!

This next set will do just that for you. Come on, the ride hasn’t ended yet.

  1. Do you find eye contact during sex sexy?
  2. What are some of the best places to give love bites?
  3. Do you like to have sex on an isolated beach?
  4. Will you have sex with someone online if you are horny?
  5. Do you like to be completely dominant or submissive?
  6. Have you tried sensual massages on your partner?
  7. Have you ever used spit as a lube?
  8. Do you like talking dirty to your partner?
  9. What would be the safest place to make your woman kiss you down there without anybody knowing?
  10. What is your favorite position?
  11. When you are horny where do you like to touch yourself?
  12. What is the kinkiest thing a girl can do to get you in the mood almost immediately?
  13. Do you like to use toys to spice things up during your session?
  14. Do you get excited if you watch someone doing it?
  15. Have you rubbed ice cubes on your partner’s body?
  16. If you could use only one pleasurable toy for the rest of your life, what would it be?
  17. Does it get more exciting if you don’t know the person before having sex with them?
  18. Do you like to make love under the blanket?
  19. Does it turn you on if you make love covered in sweats?
  20. Have you ever physically flirted with someone else in order to make your partner feel jealous?

We have all had weird sex experiences and so many memories to reminisce.

So, start asking the below listed super fun questions and be a party to the peculiar experiences of your guy.

Girl, beware, you don’t want to sound offensive!

Weird dirty questions to ask a guy

Human beings are weird (sometimes!). 😛

And when it comes to physical intimacy, you’ll definitely come across so many weird fantasies and experiences in your life.

Don’t you wanna know the naughty little secrets your partner has never told you?

Trust me, by the end of this list, you will both be laughing and rolling on the floor.

  1. Did you ever have a sex chat with someone you barely knew online?
  2. Did you ever catch someone doing dirty while being on a trip?
  3. Have you ever been sexually attracted to any of your relatives?
  4. Which movie character would you like to have a one-night stand with?
  5. What is the weirdest body part you have licked off your partner?
  6. Do you ever want your partner to behave like a certain celebrity to seduce you?
  7. Do you like to spank while doing it?
  8. What is the weirdest thing you have licked from your partner’s body?
  9. Have you ever kissed your cousin and liked it?
  10. Have you ever tricked your partner into licking you?
  11. Have you ever taken off your partner’s underwear with your teeth?
  12. What is the weirdest place you have made out?
  13. What is the most difficult position (with a guy’s perspective?)
  14. What is the weirdest thing a woman has done to you?
  15. Have you slept with anyone only to realize that you will never want to sleep with her again?
  16. What is the weirdest way you have asked for a naked picture of someone?
  17. Have you ever finished before your partner did?
  18. Have you ever tried to imitate scenes from fifty shades of grey?
  19. Who is the most unexpected person that hit on you?
  20. What is the one position you want to try out?

Hold on! What if you are talking to a guy for the first time? You want to play safe… and that is why I’ve curated some questions to spark up the “dirty” conversation for the first time.

Best dirty questions to ask a guy

Isn’t it exciting and naughty to ask dirty questions to a guy? Sure, it’s a risk but one that’s worth it. You definitely don’t wanna get too casual to make it dull or too close to make it awkward.

So, here are some of the best dirty questions that you can ask any guy without a second thought!

  1. Have you ever drank your partner’s saliva?
  2. Is it okay to fantasize about other women while being in a relationship?
  3. What is the best thing a woman can wear in public which makes it easier to touch her without anybody knowing? (if you know)
  4. What type of kisser are you?
  5. Where is your favorite spot to be kissed?
  6. Have you ever gone skinny dipping?
  7. Do you like to call your partner with different names while doing it?
  8. Do you prefer sex on the phone or video call?
  9. What would you want your girl to call you in the bedroom?
  10. What is your take on open relationships?
  11. What is the best dirty pick up line you have ever used?
  12. Have you ever imagined your parents doing it?
  13. Does rain put you in a sensual mood?
  14. Do you like to push your partner against the wall while making out?
  15. If you could choose one of your exes to do it for one night, who would you choose and why?
  16. Where do you press the most, during a session?
  17. If you could only lick one place on your partner for the whole life, where would it be?
  18. Do you like it if you are teased more before doing it?
  19. If I poured alcohol on your pants, how would you like me to clean them?
  20. Would you choke me during sex?

Want him to want you more but worried about going out of the line?

Don’t worry, I’ve got you covered baby! 😉

Sensual questions to ask a guy

There’s nothing a guy enjoys more than a sensual conversation… and of course, you’ll be able to see it in the eyes – how much he is craving for you.

The next list is specifically curated to tease him at all the right places.

Get ready to listen to some reaaalllyyyyy swooping answers!

  1. What color of a bra should I wear on our first make-out session?
  2. Have you ever watched porn with your partner to set the mood?
  3. Does falling in love makes sex more interesting?
  4. Do you like your partner to sit on your lap while you are making out?
  5. Do you love it when a woman bites her lip?
  6. What goes on in your mind while you are having sex?
  7. What is the best season to have sex?
  8. Does it turn you on when a woman bends down in front of you?
  9. Would you ever receive a lap dance from a stranger?
  10. What is the best toy you have ever used?
  11. How many positions have you tried till now?
  12. What is the most unexpected sexual dream you’ve ever had?
  13. Have you licked a woman’s body with just your tongue?
  14. Does it turn you on when a girl is wearing no panties in public places?
  15. Have you ever put your hand under a woman’s top in a public park?
  16. How much tongue do you like to use while kissing?
  17. How deep a woman has ever gone for you?
  18. Do you like it when a woman caresses your hair while kissing?
  19. Do you like to bite ears while making out?
  20. What do you consider sexier, eyes or lips?

Did you really think I would leave you there? No, of course, I want him to want you more. It’s the teasing that raises the temperature.

So let me take you down the road so that it never cools down!

Hot dirty Questions to ask a guy

I know you are loving it.

But don’t push too hard. Or if you think you’ve reached the comfort zone where you can share literally anything with each other, then why not?

Let’s dive in!

  1. Do you love to play with nipples or thighs?
  2. What is the wildest sex position you’ve ever tried?
  3. What names do you want your partner to call you while having sex?
  4. Would you continue making love if your partner is not satisfied?
  5. Have you ever tried to record yourself while you were doing it?
  6. What is the longest time you have ever lasted in bed?
  7. Have you ever fallen in love with a friend with benefits?
  8. Do you like morning sex?
  9. Have you ever masturbated in your relative’s home?
  10. Are you comfortable kissing your partner in front of people?
  11. Would you sleep with someone you met on a dating app?
  12. What is the most awkward make-out session you’ve ever had?
  13. Have you secretly watched older people having sex?
  14. Do you like doing it on the muddy ground?
  15. When was the last time you had sex?
  16. Have you ever been in a bathtub with any of your partners?
  17. When was the first time you were sexually attracted to a woman?
  18. What is the grossest place you’ve ever had sex in?
  19. Can you unhook a bra with only one hand?
  20. Did you ever have a partner with whom you had meaningless sex?

Getting intimate is one of the turning points in your relationship. It is important to know whether your guy is actually on the same page.  

If you want to know your guy even more but have trouble opening him up. Don’t worry, girl! We got you.

Sexually Intimate questions to ask a guy

After all the hot and dirty conversation starters, some of you may find this list of intimate questions non-beneficial. But let me tell you, intimacy is not all about sex.

If you are a long-term relationship type of person, you know it’s worth it!

Try using these questions during foreplay and thank me later! 😉

  1. Would you have sex with a person if you’ve only known them for a few days?
  2. Are you shy in bed?
  3. What turns you on more? Intelligence or beauty?
  4. Do you like it when I tough you on your thighs?
  5. What have you not tried in bed yet?
  6. What is the difference between a one-night stand with a stranger and doing it while being in true love?
  7. Is it okay to say I Love You during sex?
  8. What was it like the first time you did it?
  9. Have you ever done it on your parent’s bed?
  10. Have you ever fallen from bed while doing it?
  11. What mistake did you make in bed for a long time?
  12. Have you ever made out in a club?
  13. What is the kinkiest thing you have done in the bedroom?
  14. Have you ever licked off ice cream from your partner’s lips with your tongue?
  15. Have you ever wanted to kiss your teacher?
  16. What is your ideal place to have sex?
  17. Have you ever confessed your love during sex?
  18. Have you ever seen a disappointed look on your partner after sex?
  19. Have you ever gotten hard when an older woman 3 times your age touched you?
  20. Have you ever smelled your partner’s underwear?

If nothing comes under your “situation-ship”, you can always ask some random dirty questions to make the conversation interesting.

Random dirty questions to ask a guy

Well, it’s not always necessary to ask dirty questions to the guy you like. Dirty topics can be the highlight of any conversation.

So, I’ve compiled some of the dirtiest random questions to spark up any conversation and uncover some of the random secrets they have been hiding.

Get ready for some dirty fun, peeps!

  1. Did you ever follow any sexy pages on social media?
  2. Have you ever had a dirty dream of your relative?
  3. How many girls have you been with?
  4. Has anyone ever walked in on you while making out?
  5. Do gay couples turn you on?
  6. Have you ever hit on your friend’s ex?
  7. Has any girl ever abandoned you in the middle of making out?
  8. Have you ever asked for blue films from any of your friends?
  9. Did you ever cheat while being in a long-distance relationship?
  10. Have you ever fantasized about any of your friend’s girlfriends?
  11. Would you hesitate to have sex with a girl who is not a virgin?
  12. Have you ever booked a private room?
  13. Do you think you know what women want in the bedroom?
  14. Would you ever do it in a tourist place?
  15. What is the wildest thing you have ever done in the bedroom?
  16. What do you prefer more: Hands or mouth?
  17. Where was the most embarrassing spot you got horny?
  18. How often do you get horny?
  19. Have you ever seen gay blue films?
  20. Who is the best partner you have ever had in bed?

Do you know you can seduce your partner just by asking the right questions?

If you don’t know what to ask, here’s where you can start.

Seductive questions to ask a guy

Seducing a guy may not be as easy as it sounds. But it isn’t as tough either.

And if you know his weak spots, it’ll be a walk on the butter!

Don’t believe me, try it for yourself.

  1. Do you have any special roleplay experience in mind? Like doctor-patient or Kidnapper-victim?
  2. What part of the body do you notice first when you meet a woman for the first time?
  3. Have you ever directed a woman to meet you in an alone spot for making out?
  4. When I stay closer to you, do you smile?
  5. Have you ever done it in the kitchen?
  6. Do you like to communicate during sex or prefer no talking at all?
  7. What is the best kiss you have ever had?
  8. Have you ever been naughty while eating at a restaurant?
  9. How fast can you get a woman there?
  10. Do you like doing it with or without protection?
  11. Have you tried to do a hardcore session?
  12. Would you like to do it in front of the mirror?
  13. How fast can you take off clothes from your partner’s body?
  14. What type of song gets you in the mood instantly?
  15. Have you ever tasted your partner’s saliva?
  16. What do you prefer more? Boxers or briefs?
  17. Do you like to give a finger-job to your girl?
  18. Do you have a fetish? What kind of fetish?
  19. Do you like to moan your partner’s name? 
  20. If a woman wears a completely sheer dress, will it turn you on?

Get things a bit more down there, with some best sexual questions to ask your guy.

Sexual questions to ask a guy you like

When you like someone, no amount of time is enough for them. You always want to be around him either in person or call or text. But what if the guy isn’t making his move on you.

Well, take my advice. You take the first step.

It is very obvious that guys love it when women make the first move. But what should you ask him to spice up the mood?

Take notes from some of these super good questions.

  1. If I were there with you right now what would you have done with me?
  2. If given a choice, would you like to make out with me?
  3. Describe your sex life in 3 words?
  4. If you met me today for the first time would you have done with me?
  5. Have you ever tried to hit on your neighbor?
  6. Would you tear off my clothes?
  7. What is your best makeout spot?
  8. When was the last time you watched a blue film?
  9. What is your idea of a perfect woman?
  10. Do you like big breasts or big butt?
  11. Would you watch an adult film with me?
  12. What is the longest you’ve kissed someone?
  13. Would you like it if I am wild in bed?
  14. Do you like to kiss thighs?
  15. Do you prefer quickies more or a marathon session?
  16. Are you more of a cuddling or kissing guy?
  17. Do you like to keep the lights on or off?
  18. How many times can you do it in one day?
  19. What’s the most flirtatious thing you have ever done to attract a woman?
  20. At what age did you lose your virginity?

We all have that one friend or maybe the guy you like hasn’t done it yet.

While it’s pretty amazing to tease them, you have to play safe too.

So, keep faith in me for I have a complete set of questions to tease him perfectly but subtly.

Dirty Questions to ask a virgin guy

Haven’t lost your virginity yet? No issues. Will that stop people from making fun of you? Umm, definitely not!

Teasing a virgin with some dirty talking can be so exciting and you will also be surprised to find out what your friends are hiding.

  1. Would you like to fall in love before having sex with them?
  2. What is an ideal time to wait before losing your virginity?
  3. What is the perfect place to have sex for the first time?
  4. Have you ever been sexually attracted to your Mentor?
  5. Do you get turned on if you find couples making out?
  6. Are you shy to get naked in front of a girl?
  7. Would you make out with a sugar mommy?
  8. Have you ever masturbated seeing a blue film?
  9. Would you wait till marriage to lose your virginity?
  10. What should perfect foreplay look like?
  11. (If they have siblings) Have you ever been sexually attracted to any of your sister’s girlfriends?
  12. Have you ever tried to get your dirty picture?
  13. Do women in bikinis turn you on?
  14. Have you given yourself a handjob?
  15. How far can you go to have sex with a girl out of your league?
  16. Have you ever checked out your friend’s mom?
  17. When was the first time you touched yourself?
  18. Do you picture your female friends naked?
  19. Have you ever been to a nude beach?
  20. Has anyone ever caught you while your thing was out?

You would be lying if you never had played truth or dare in your life… how about we add some dirty flavor to it?

Wait no more. Spin the bottle and get ready for what awaits you! 😉

Dirty truth or dare questions to ask a guy

A game of truth or dare with a dirty touch can be the highlight of the night. You can play this anywhere – with your friends, or even on your sister’s birthday eve.

But if it’s a date night just with your partner, imagine how you can be so creative with the dares!

Hold those dirty thoughts, girl. Let him at least decide: Truth or Dare?

Whether he chooses to play truth or perform a dare, be prepared with the question list.

  1. Have you ever sent someone a funny picture of yourself?
  2. How many times have you been complimented for being good in bed?
  3. What is the maximum day you can go without doing it?
  4. Can you start doing it without foreplay?
  5. Have you ever felt the connection was off while doing it?
  6. Have you ever done it with a stranger hours after breaking up?
  7. Have you ever faked it?
  8. What is the one thing you will never do in bed again?
  9. Have you ever made out with someone just because you wanted a favor?
  10. Have you ever played dirty truth or dare questions with a group of strangers?
  11. Are you more of a casual or a serious guy in relationships?
  12. Have you ever tried to do a position you first saw online?
  13. Do you make a funny face during sex?
  14. Tell the name of the last person you kissed?
  15. Have you ever taped while doing it?
  16. Have you ever tried practicing a position with a pillow?
  17. Are you generally exhausted or enjoying the second round?
  18. Are you insecure about your size?
  19. Have you ever dated someone skinner or curvier than you?
  20. Has anyone ever mistaken your girlfriend as your underage sister?

You know a lot about a person when you put them in a position to choose between two. Well, it gets even better when you add some dirty spices too.

Confused? Let me explain.

Dirty “Would you rather” questions to ask a guy

Even if you haven’t played this game before, there’s no way in hell why you must not consider it.

In this game, the answerer is given two difficult choices and asked to choose one. It can put him in a tough spot, but that’s what this game is all about.  

I’m not taking responsibility if you make an ‘o’ face for a long time. Just kidding. 😉

  1. Would you rather kiss my ears or neck?
  2. Would you rather see a striptease or seductive dance?
  3. Would you rather touch me or let me touch you?
  4. Would you rather want me on top or under?
  5. Would you make love on a hill or on a beach
  6. Would you rather invite someone for a threesome or get invited for a threesome?
  7. Would you tie up your partner or get tied up?
  8. Would you rather watch an adult film or cuddle till you get horny?
  9. Would you rather book a room or do it in your house?
  10. Would you rather get a full body massage or give it?
  11. Would you rather give a blowjob or take it?
  12. On a blind date, would you rather let her make the move or you will do it?
  13. Are you the one that ghosts someone or gets ghosted after having sex?
  14. Do you like to do it more in hot or cold weather?
  15. Would you rather have more eye contact or nothing at all?
  16. Would you have a one-night stand with your ex or your friend’s ex?
  17. Would you rather die a virgin or sleep with someone of the same sex as yours?
  18. Would you rather lick melted chocolate from a spoon or my butt?
  19. Would you rather watch couples having sex or be watched while having sex?
  20. Would you rather do it on a boat or a bench?

Don’t stop here. You create so many more questions and keep the conversation going.

But since you are here, I figured you might be tired of creating questions and just want to enjoy the dirty talk.

…even on text messages.

Dirty questions to ask a guy over text

It’s very convenient to use these questions while you are sitting with him in person. While playing over text, it’s a different ball game altogether. But don’t worry, as I said, you have me until the end! 😉

Well, when you do not face to face, you can let yourself loose and stripe dirty conversations without making it too obvious.

Keep these questions handy for your dirty “text” conversation. The answers are sure to make you read your chats over and over again.

  1. If I were there with you in a room right now, what would you have done to me?
  2. What do you think I am wearing right now?
  3. Which parts of your body do you admire the most?
  4. Have you ever thought of me when I am not there?
  5. What was the age of the oldest woman you have ever kissed?
  6. Would you play sexy games with me?
  7. What is the best place to do it in your own house?
  8. Have you ever tried sexting?
  9. Where do you stare the most when I am sitting in front of you?
  10. Do you want me to send you a nude picture right now?
  11. Would you put your hands on my thighs when you are driving?
  12. Have you ever read erotic stories?
  13. Would you tape yourself masturbating and send me if I ask you to?
  14. Tell me a dirty truth about you no one knows?
  15. Would you ever take a shower with me?
  16. Have you ever had a sexual dream about me?
  17. Would you like it if I ran my tongue over you?
  18. Would you allow me to taste you?
  19. Have you ever clicked your nude pictures?
  20. Would you let me sit on your lap?

There’s nothing more exciting than doing some flirty dares over text. With all the right elements, a good internet connection, a fiery mood, and obviously a list of questions… you can create a memorable time for yourself. 

Get in the mood with some sexual dares that are a sure-shot way to spark up the heat. 

Sexual dare questions to ask a guy over text

This may be the last on this list, but hey, the fun has just begun.

Sending dirty dares over text will make your guy crave you like crazy. You will definitely not be able to resist yourself after asking this set of questions.

So, the next time you meet, there will be a lot of shy stares or sly smiles involved… and maybe some “bed” fun also! 😉

  1. If I was with you right now, would you watch a blue film together?
  2. Would you unhook my dress if I asked you to?
  3. If my texts make you smile, you have to kiss me.
  4. If you wanted a dirty picture of mine, how would you have asked for it?
  5. What would you have done, if I wanted you right now with me?
  6. How often do you touch yourself?
  7. Did you ever cheat on your partner and get caught?
  8. If you have ever done it with 2 different persons in 24 hours, send me a kissing smiley?
  9. Would you have me as a rebound if you broke up right now?
  10. If I were handcuffed and blindfolded on the bed right now, what would you have done?
  11. If you had me for only one night, how memorable would it be for you?
  12. Would you ever kiss my best friend behind my back?
  13. Let me go through your Google search history!
  14. What do you think is my favorite part of your body?
  15. What is the most kissable spot in my body?
  16. Have you ever asked someone to send a picture as a dirty dare game?
  17. Did you ever get there by sexting or calling?
  18. Would you always be naked while making love?
  19. Do you ever put on Santa’s naughty for a role play?
  20. Did you ever have a one-night stand before committing to a serious relationship?

That wasn’t all.

I still have some bonuses for you, girls!

After all, you stuck with me until here. I can’t do something special for you.

So, here are 5 tips on…


5 Tips to make the dirty conversation with a guy

Asking dirty questions can be really tricky… more so, if you don’t know the guy much.

But if you know the tricks and have a great question list handy, it can definitely give you a head start. But how will you separate an average list from a great list?

Here’s your answer!

1. Know your partner

Your guy should feel comfortable enough to answer these questions. If you want to save yourself from awkward glares, be careful of the questions that you are asking.

Know your partner’s boundaries and be subtle with your questions initially. Eventually, as he gets comfortable, slowly drives the conversation to the dirty side.

2. Make sure that the guy likes you

There is nothing more embarrassing to do all the hard work by asking these questions if the guy has no interest in you.

If you notice that the person is enjoying the questions you ask him, go with it. But if they aren’t, just play cool and be subtle.

3. Notice what kind of question the guy likes.

If he is not enjoying certain types of questions, refrain from asking them because at the end of the conversation you need to feel more connected to your guy rather than pushing him away.

4. Just be yourself

There’s nothing more attractive than being yourself. Play cool while asking these questions and gradually get deeper to get him to open up.

5. Lastly, enjoy

All the hard work will go into vain if you are not enjoying yourself. Pick questions in a way that the answers not only send you chills but also keep you both hooked to each other.

And now that I’ve already done half the task with this, why would you take the stress?

Over to you…

Like I said, asking dirty questions to guys can be tricky especially when you are just getting to know each other.

As a girl, you are expected to start a conversation but sometimes it is very difficult to identify questions that will not make the other person awkward.

I’ve been in your place too.

That is exactly why I created this list of questions while still keeping it hot and dirty.

Now, what’s the wait worth? Go ahead and keep asking, girl!

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