150 + Flirty And Dirty Questions To Ask Your Boyfriend

Do you want to add some excitement and intimacy to your relationship? Asking naughty, suggestive questions is a fun and flirty way to explore each other’s hidden desires.

I’ve put together 150 tantalizing conversation starters ranging from sweet to steamy. Try sprinkling a few into foreplay and see where things lead you!

Here is an expanded list with 15 examples for each category of dirty questions:

Romantic and Flirty Questions

What physical features do you find sexiest about me?
Which outfit do you most love to see me wearing?
What non-physical trait turns you on the most in me?
When during the day do you tend to feel most desperate for sex?
Would you prefer a massage first or jumping right into foreplay when we’re intimate?
If you could touch me anywhere right now, where would your hands go first?
Would you rather I wake you up with gentle cuddling or frisky fondling?
If I greeted you at the door in just heels and lingerie, what would you do?
What public place other than the bedroom excites you most to fool around in?
Have you ever had a wet dream about me? Tell me all the juicy details!
Would you prefer sweet and romantic or rough hardcore sex tonight?
If I gave you a cheeky nipple pinch out of the blue, would you find that playful or annoying?
Which striptease song would you most want me to dance to?
On a scale of 1-10, how horny for me are you feeling right now?
If you could touch or kiss any part of my body right now, where would you start?

Oral Sex Dialogue

Do you prefer giving or receiving oral sex?
Have you ever 69’ed with a partner? Did you enjoy it?
What exactly do you like best when I go down on you? Be very detailed…
Would you prefer me to swallow or give a facial when finishing oral?
Can I practice my oral techniques on you for 30 minutes with no expectation of reciprocity?
Do you like lots of teasing and build up or prefer I dive right into intense oral stimulation?
What pace do you enjoy most – fast and vigorous or slow and sensuous?
How do you feel about having your testicles gently stimulated during oral?
Would you enjoy if I slipped a finger or two inside your bum while sucking you off?
Do you mind if I use my hands simultaneously while blowing you or do you prefer my mouth only?
How would you feel about trying to achieve female ejaculation through dedicated oral attention?
Have you ever received analingus (rimming) before? Did you like it?
Would you be open to incorporating toys like vibrators or butt plugs during oral play?
Can I practice edging you with my mouth by bringing you close to climax over and over before finally letting you cum?
Which location for receiving oral feels most exciting to you – sitting, standing, laying down? (Here is guide on How to talk Dirty)

Sex Toy Curiosity

Have you used vibrators or sex toys before either alone or with partners? Did you enjoy them?
Would you feel shy or nervous at all if I introduced a toy during foreplay?
Which category of sex toy intrigues you most – vibrators, plugs, massage oils, restraints, etc? Why?
If you could pick one toy for us to try first, what would you choose?
Have you ever used a cock ring before? Would you maybe want to try wearing one?
Is a clitoral vibrator something you’d be curious to experience?
CyberSkin masturbation sleeves feel incredibly realistic. Would a device simulating anatomical parts fascinate or weird you out at all?
Do you think remote controlled toys worn secretly in public could be thrilling?
Would you enjoy using a rechargeable wand-style vibe together during sex? Where should I focus vibrating: penis, testicles, perineum, elsewhere?
Have you ever tried a butt plug before? What size would you be willing to experiment with if you haven’t?(Guide To Anal Sex)
Bondage gear like silk restraints or feather ticklers can heighten sensations. Are those items you’ve fantasized about trying?
How would you feel about stimulating genitals simultaneously with a synchronized dual pleasure vibe?
If I surprised you by slipping a stretchy cock ring down your full erection would find that exciting or uncomfortable?
Do you think vibrator play focused exclusively on the frenulum and corona could produce explosive orgasms? Should we experiment?
Would you be willing to use a wearable vibrating male sex toy beneath clothes the next time we go out to dinner?

Anal Play Questions

Have you received anal stimulation like prostate massage or rimming (analingus) before? Did you enjoy it?
Would you ever consider more advanced anal play like pegging or double penetration with toys? Under what circumstances could you see experimenting with those activities?
Can I gently lick around the outer part of your anus during oral sex sessions?
If I slowly inserted my pinky finger just an inch or two into your bum during intense fellatio would find that intriguing or weird?
What about prostate stimulation while receiving oral – does manually massaging the male G-spot interest you at all?
If I slipped a very slim smooth plug or beads in you while going down would you be open to trying that once just to see how it feels?
Have you ever played with your own anus during masturbation? Did you incorporate any fingering or toys anal penetration?
How would you react if I gave you a surprise external prostate massage when you were highly aroused to push you over the orgasmic edge?
Would wearing a butt plug for an hour before sex heighten arousal enough that you’d consider trying it?
What about experimenting with a sex machine that allows self-controlled fully-penetrative thrusting – does working up to taking something sizable in your bum excite you or scare you?
If warming lube helps relax the anal sphincters, would you be more likely to attempt double penetration with me using toys and fingers covered in it?
Have you ever watched trans female on male anal porn before? Did seeing a taboo flip of gender norms spark any curiosity in you even briefly?
If you enjoy analingus, would rimming plus gentle fingertip prostate stimulation at the same time send you over the moon potentially?
Do you have interest in simultaneous double penetration – vaginally with your penis plus a second dildo or plug anally?
Would interactive solo tech like the Lovense Edge prostate massager intrigue you as a way to explore anal and P-spot stimulation privately first before trying partnered play?

Fetish and Roleplaying Ideas

Do you secretly fantasize about any fetishes or kinks that you feel too shy to ask me to explore with you?
Would you enjoy being blindfolded while I give you a naked full-body massage followed by oral pleasures?( Here is the Complete Bdsm Guide)
Have you ever experimented with soft bondage like silk restraints or fuzzy handcuffs during sex before? Did you find it exciting?
If I modeled fetish attire like leather, latex, or fishnets, would that kind of racy costume turn you on? Which is hottest?
What would your reaction be if I greeted you at the door wearing nothing except a frilly apron and holding a martini ready for you? Would you find that scenario playful or silly?
If we used a wireless remote controlled sex toy discreetly in public, when would be the most thrilling times for me to randomly activate strong vibes against your penis to create sexual tension? A nice restaurant? Driving in the car? At the movies? The options for erotic mischief could be endless 🙂
Have you ever incorporated food play into foreplay before like drizzling honey or chocolate sauce over body parts to then lick off? Would you be willing to experiment with sweet sensory teasing using whipped cream or fruit?
Slight sensations of constriction around the genitals can really amplify orgasms for some people. Would you be nervous at all about trying one of those stretchy cock rings or adjustable pleasure loops I mentioned? I’d be very gentle putting one on you of course! And if it felt uncomfortable rather than enjoyable, we’d take it right back off.
Do you think you’d achieve incredible hands-free climaxes if I slipped a vibrating prostate toy in you while simultaneously sucking your cock? Should we buy one to experiment with that intense dual stimulation?
Masks, wigs, costumes and roleplaying allow us to safely explore aspects of our shadow selves. Would pretending to be someone else forbiden entirely – like a priest plus nun – potentially free our darker repressed desires if we created anonymous alter egos?
Have you ever peeked at Femdom porn out of curiosity about the idea of a very assertive woman dominating a meek male? Did you find those gender/power dynamic reversals exciting even briefly or just unappealing?
Would tying you up spread eagle to the bed facedown, then teasing every inch of your body with fingers, tongues, toys, hot wax, and feather ticklers ultimately make you beg desperately for penetrative release after enough edging?

Taboo Topics

Does the idea of risky public or semi-public sex actually excite you tremendously even though it’s legally and socially prohibited in most places? What location seems thrilling – changing rooms, parked cars at night, rooftop hot tubs, empty theatres?
Would any incest-related roleplay scenarios turn you on intensely or just weird you out too much to enjoy them? Doctor/patient dynamics? Teacher/student? Mommy/son? Daddy/daughter? Etc.
Have you ever peeked at bisexual or gay porn out of curiosity about the same-gender experience? Did watching those scenarios spark even faint arousal or mostly disinterest?
Under what circumstance might willingly experimenting sensually with someone of your same gender occur – such as at a party if you were drunk or high perhaps? A prostitute on vacation? Etc. Basically what context could possibly enable bisexual exploration for you?
Does gender matter – do you think fooling around with another man would feel too uncomfortable while female/female play might be exciting since women are softer and feminine by nature?
Would you feel nervous hearing about my secret lesbian experiences yet also exhibit sheer primal arousal seeing me make out and grope another gorgeous woman? Does visual stimulation trump emotional discomfort for men when witnessing raw female homosexual energy?
Have you ever been to underground swinger/kink events before? Did you find the crossover between ART and raw eroticism empowering or mostly just awkward?
Do you think attending a classy burlesque show or elegant kink demonstration could open our minds to new erotic concepts in safe ways without actually swapping partners or groping strangers which feels uncomfortable?
Would you enjoy filming or photographying our own intimate erotic moments then privately rewatching those short movies as part of foreplay to become turned on? Does DIY amateur porn created strictly for us to enjoy together appeal to you?
If we designed Fetlife or alternative social media profiles to initially explore the kink community online only through discussion forums, not in-person meetings, would that digital entry point interest you? Just chatting with like-minded kinky people first before deciding if we want to explore anything in real life at sex clubs etc?
Have you ever engaged in any form of group sex – threesomes, partner swapping, orgies, etc? How did you find the experience and would you maybe want to try attending a swinger party “just to watch” first without swapping partners as a baby step?
Do everyday power dynamics – like boss/employee – ever sneak into your private fantasies? Do you think roleplaying forbidden scenarios would help subconsciously release shame, healing repression psychologically without actual noncon consequences?
What are your thoughts about the recent hype surrounding Orgasmic Meditation – apparently it’s just gentle stroking of the upper left quadrant of female genitalia without any goal-oriented climax, simply tuning into the pleasure senses mindfully. Does such a concept intrigue you or seem too odd?

I hope these naughty questions get both of our imaginations flowing! Tell me which themes seem appealing to explore together first and I’ll try to incorporate related teasing and play next time we’re intimate…

This list barely scratches the surface of naughty or amorous subjects partners can explore together! Feel free to build upon it over time as your comfort levels for experimentation expand.

The most important thing is avoiding judgment toward any kink or fantasy your partner shares, even if it doesn’t personally appeal to you. Show enthusiasm instead of scandal. That encourages openness and adventure.

So have fun getting flirty tonight! Spark intimacy through risqué conversation and then thoroughly enjoy whatever sexy inspiration follows…

Resources:

Dirty questions: Indigenous health and ‘Western research’