40 Naughty Questions To Ask Your Shy Partner And Have Sex

Sexual, flirty, down right dirty questions to ask your partner

By Aey
40 Naughty Questions To Ask Your Shy Partner And Have Sex

We have all, at times, found ourselves in the mood for physical intimacy and sometimes at a loss for a decent enough way to segue into that conversation with our partners – having a shy partner makes this even harder. Are you sick of being awkward and horny around your partner and not sure what and how to get the mood and the groove on? Fear no more! Here we have for you a compilation of questions to ask a shy partner to gauge their interest and figure out your prime sexual compatibility.

How to Initiate a Dirty Conversation Good For a Super Shy Partner

Initiating a dirty conversation can be tricky – it can go really well but it can just as easily make you come off as a bit of creep if you misread your partner’s signals. Here are 5 ways to help you out!

1. Steering the conversation from a romantic subtext

If you are dealing with a super shy partner, you need even more priming and it would be best to start off with a more romantic subtext and steer the conversation into more of a sexual realm gradually. Compliment them or maybe, ironically, use a cheesy pickup line on them! Make your partner laugh and feel comfortable and close to you! Here’s an example,

You: Hey baby! Are you from Tennessee?

Them: Babe, you know I’m from Texas?

You: Really! Cause you’re the only ten I see!

They’ll laugh and open up to you and will give you a great chance to lean in and steal a kiss.

You can also respond to their stories in compliments and telling them how much you mean to them, so your shy partner feels safe and close to you.

2. Playful touch

Body language is key! – You do not want to start sexy talk without creating an environment where your partner feels safe but also excited and open to physicality. Physical proximity and playful touch is a great way to warm up a partner to the prospect of dirtier conversation. Play the classic counting shoulders trick or just put your arm on their shoulder so they can snuggle up to you. If you two still have not gotten physical and are a bit uncomfortable with your touch, try playing a game of thumb wars and play with their fingers. All of this sets the mood for a more explicit conversation that is hot and not abrasive and creepy.

3. Use an aphrodisiac

Okay so this next one may seem a bit extreme, “cray-cray,” but why not take some help from a good old aphrodisiac. Most people think an aphrodisiac is just food or a drink that is thought to heighten sexual drive, but not many know that scents can also be aphrodisiacs. For example, the scent of apple is a surprising aphrodisiac that arouses a primal sexual instinct. Oysters, chocolate or the good old, well known sexy snack, chocolate covered strawberries are also your best friends to set a sexual vibe. And make a conversation that could be awkward, easier. Feed your partner the chocolate covered strawberry or eat it yourself in a seductive way! Initiating sex with your partner will be all the easier with the help of these little aids.

4. Roll out the sexy tunes

We have all seen those smutty scenes in movies where the protagonists get down and dirty. And almost all of them feature some snazzy tunes to put you in the mood for some steamy time. Why not try putting on some of your favorite sensual songs and break out into a sexy or silly little dance to get their attention? It will put some arousing thoughts in your partner’s mind. Lip syncing some nasty lyrics is also a fun way to set a naughty mood! Music is a proven, tried and tested technique to influence and bring forth those sexual vibes! Lovemaking is an art and a good artist knows how to use his tools to the best of his abilities.

5. Massage your partner

Nothing beats physical touch in communicating nonverbally. After a long stressful day, give your partner a shoulder rub or a back massage. Maybe just place a hand on their thigh and massage to get the feeling that sexual energy. Few know this, but feet rubs are great gateways to sex – who would have thought feet would work for people even without those foot fetishes? – it’s because we have some intrinsic erogenous zones on our feet that stimulate the libido. Asking dirty questions during this is a great way to accentuate a vibe and not come off as aggressive or awkward.

If Your Super Shy Partner Is A Girl

  1. What do you look for in a partner for the bedroom?
  2. Spit or swallow?
  3. What do you think about toys in the bedroom?
  4. Does the thought of recording a video turn you on?
  5. Have you ever tried edible underwear?
  6. What was the last dirty dream you had? Was I in it?
  7. What's a naughty fantasy you have about me?
  8. What's one public place where you would want to do it?
  9. Have you ever played strip poker?
  10. What's the wildest thing you've ever done?
  11. Do you ever watch adult videos?
  12. Do you prefer to give or receive?
  13. Can you send me a sexy pic of your favorite body part?
  14. Can I watch you pleasure yourself?
  15. How would you feel if I made you breakfast while wearing only an apron?
  16. Do you prefer doing it in the morning or at night?
  17. Rough or sensual?
  18. What's the longest intimate session for you?
  19. What was your first time like?
  20. Who do you think of when you pleasure yourself?

If Your Super Shy Partner Is A Guy

  1.  In an ideal world, how long would foreplay be?
  2. What do my lips taste like?
  3. Is there a sexy scene from a movie that you want to recreate with me?
  4. If you had a pair of x-ray glasses, which part of my body would you look at first?
  5. If you could only touch me in one place, where would it be?
  6. If we were in a movie theater, and I wanted to do it, what would you want me to do?
  7. What's one thing you want me to do to you that I haven't done?
  8. What's the farthest you've gone on a first date?
  9. What would you do if I sent you a dirty photo of me?
  10. How would you describe your package?
  11. Do you want to play dirty truth or dare?
  12. Guess what I'm wearing right now?
  13. What would you do if I answered the door without clothes on?
  14. Have you ever been caught going solo? By who?
  15. Do you prefer your women shaved or all-natural?
  16. Is laughing in the bedroom okay with you or do you prefer keeping things serious?
  17. What's the longest you've gone without doing it?
  18. What's the most number of times you've done it in a row?
  19. Do you like watching me touch myself?
  20. I heard kissing burns a lot of calories. Want to help me exercise?

What to Do If Your Partner Is Not Responding Well

Sometimes even if you check all the boxes in romantically approaching your partner, they are just not getting the message! At this stage, you might want to approach things a little more directly and if they still are not vibing, it’s probably best to just back off and jack off in the bathroom alone! However, if you see some hope of salvaging the situation try to communicate with them – place a hand on their thigh or hold and place a gentle kiss on their hand and let them know you want the both of you to have a great time and want to know more about their preferences to be able to do that. Running into trouble initiating sexy talk or sex itself is not uncommon – try again in a different situation and most importantly learn from what your partner did not respond well to!

Related Article: 25 Naughty Games To Play With Your Partner When You’re Bored
25 Naughty Games To Play With Your Partner When You’re Bored

Boredom sucks...but so do you, which can make for some great naughty games that involve touching and chatting for you and your boyfriend!


The best advice is to be comfortable in your skin – if you are awkward and constantly second-guessing yourself your partner will not be turned on! Be confident, be respectful but most importantly have fun with it and have a little humor about it and you are sure to transfer that confidence and calm into your partner. If there is awkwardness the best way to get rid of it is to address, it! And know when to stop – if your partner looks uncomfortable do not go on, change strategies or try again later or maybe even have a candid conversation about it!


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