21 Sexual Questions To Ask a Guy For Fun And Intimacy

21 Sexual Questions To Ask a Guy

These 21 sexual questions to ask a guy could well be a relationship saver in some situations. It could be what might give you and your boyfriend that intimacy you’ve been longing for. So grab a cup of coffee or something, make yourself comfortable and happy reading.

So, you and your crush have been flirting back and forth, you finally went out on that first, second and even third date, to say nothing of subsequent outings, and you’ve decided to make it official: you two are a couple!

Or perhaps your relationship isn’t quite so whirlwind. Maybe romance has blossomed out of a longtime friendship, which is seen as somewhat rare anymore, but it’s all the sweeter for the longevity and trust built between the pair of you.

This is particularly true if you’ve gone through certain milestones with each other as younger people, such as your first driver’s license, going to school dances, studying for difficult exams, and even deciding that you don’t want time and distance separating you after high school, so you enroll in the same university.

Whatever scenario you find yourself in, even beyond college, there comes a point in any budding relationship where the inevitable happens: the pair of you have clearly gone beyond innocent flirting, and one night, you perhaps decide to “make it to home base,” to use the old baseball metaphor.

Here’s the deal, though: in order for you and your guy to really build trust in the bedroom, concerning what each of you likes, what you’d want to try out, what turns you off, and so on, you’ll need to ask questions of each other. You might to decide to play a game and write out sexual questions to ask a guy when playing 20 questions

The following are 21 of the most commonly asked questions you can ask your guy, and you can even turn it into a fun, more intimate version of “20 Questions,” which is always a fantastic way to spend time together without laying out a bunch of cash.

Unless you have certain questions in mind that actually involve a certain level of interactivity, that is, and you don’t have specific “equipment” on hand, as it were. Then it might be time to hit the adult novelty store before your fun can truly begin. And if you want to put your guy on the spot for some fun, write out some awkward questions to ask a guy secretly and throw them at him unexpectedly and see how he reacts.

Let’s start with the first bunch of questions, shall we?

Sexual Questions to Ask a Guy Over Text

Even if your guy has a decent grasp of a good work-life balance, or work-school-life balance, making you a priority in his life as much as possible, it never hurts to turn up the heat via text while he’s at work, especially if he’s somehow already got an office job where it’s a bit easier for him to hide a certain reaction to the hot, intimate questions you might send him. Such questions might be better saved for the weekend if he has a more service-oriented job, such as a cashier or stocker.

Here are some great possibilities, ranging in “temperature” from “lukewarm” to “blazing hot”:

1) Do you check me out when I walk away? An innocent, flirtatious question that’s perfect for when you suspect the guy you’re crushing on is crushing on you right back. It indicates both sexual and emotional interest on your part, and if you get a bold “yes,” you can say something like, “Good, because I do the same to you.” Add a “wink” emoticon, and ta-da! He’s likely to keep the flirty, sexy texting going as long as he’s able.

2) Can you guess what color panties/bra I’m wearing? Say your initial conversation goes as you hoped, and he’s confessed to really having the hots for you. Turn up the heat a bit more with this question, and he won’t be able to get the image of you out of his head, even with a pile of work on his desk. Caution: this might lead to some burn-the-circuits-level sexting, which could easily be interrupted if he’s not the head of his own firm with the power to say “hold all my calls.”

3) Have you ever skinny dipped? A fantastic question, especially in the summer, and you know there’s a local place where you both can do that without anyone looking on. This is particularly good for folks who live near oceans or have a private pool.

4) What’s the sexiest thing a girl can wear to bed, if anything? An ideal query if this is the first time you’ve considered wearing sexy lingerie, and have seen something you might enjoy wearing for your guy. This question can lead into a really intriguing conversation, especially if this is your first real relationship and your guy’s a bit more experienced. (Hey, you have to start somewhere!)

5) If I was with you right now, what would you do to me? An all-cards-on-the-table question that will get your guy’s mind reeling and a volcanically hot conversation started. Again, questions like these really ought to be used with caution, based on your individual work-life situation.

Sexual Questions To Ask a Guy You Like

“Those questions are great,” you say. “But I’m only just seeing this guy for the second or third time. It hasn’t really advanced to heavy text-flirting like that. What’s more, I want to let him know I want to take that next step, but I’m too scared to get him in trouble over sexy messages. Also, texting seems so impersonal. I want to be with him when I ask this stuff.”

Wanting your newest flame to keep his job and wanting the pair of you to be physically present with each other while asking sexy questions are both fair arguments to make. So, here are some questions to ask the guy you like, without the barrier of circuitry and potential interruptions from a boss or co-worker getting in the way of your getting closer to your crush:

1) What was your first time like? Was it with anyone special? If he hasn’t yet revealed his past history, this will open him up for sure. Should he be trusting and honest enough to reveal that you are his first, whether because of self-imposed restrictions, outright shyness with girls, or any other reason, it goes without saying to tread a bit lightly. He might be feeling embarrassed that he’s not the more experienced one, since that tends to be the secular expectation towards guys.

How to handle this? With as little judgment as possible, as well as a playful, flirtatious hint of “It’ll be a lot of fun starting with the ultimate basics.”

2) Are you a good kisser? Care to demonstrate? If you’re on your second or third date—or more--and it’s clear there are some sparks, but he hasn’t completely made a move yet, chances are, he’s scared he’ll make a move too soon. Guys prefer directness and getting to the point of something, so if you’re staring at his mouth and wondering how he kisses, this question will thaw out the iciness of fear and give him a super-flirty green light, especially if you lean in with a flirty smile and a low, sexy voice with that second part of the question. You can’t get more direct than body language!

3) Do you like talking dirty? Technically, this question should be at the very beginning of this post, but since this question could be suitable for second or even third dates, we’re leaving it here. Chances are, most guys you’ll meet don’t mind dirty talk at all on one level or another. You’ll have to let him know your own limits for dirty talk, of course, if you’re uncomfortable with certain words, phrases, etc. Either way, this is a fabulous ice-breaker of a question.

4) Have you ever had phone sex? Chances are, if he’s actually been with a girl before, he’s very likely had phone sex. Asking this question in the most sultry voice possible will very easily get his engines going, as it were. If he hasn’t done this, your next step is to ask if he’d be willing to try it with you, especially if one of you has an upcoming long-distance trip.

5) Have you had sex so good it woke the neighbors? Ultimately, this will help you suss out if he’s literally quite vocal about how good sex feels, or if he’s keen to keep the noises of mutual pleasure to a minimum.

6) Ever had a one-night stand? If you have, would you do it again? While this could be a legitimately serious first-date question, this could also fall under the category of a naughty “Truth or Dare question”. Particularly if you’re at a party with other close friends, and the lot of you are making a game of getting to know each other via sexy questions.

You could ask such a question of the one guy you’re crushing on in the room without letting on you want to jump his bones, let alone date him. While this may seem a bit too indirect a way to get his attention about such things, it might allow you to suss out if he’s a player, or if he’s more interested in a long-term deal these days. (After all, why waste your energy crushing on him if he’s too busy breaking hearts?)

7) Where in the world—literally--would you most like to do the deed? Once more, a great ice-breaker for double-date game night (best done with people you’re really close with!), or a teasing tete-a-tete on maybe your fourth or fifth date. It lets you know what your current fling is thinking about concerning lovemaking locales.

Intimate Questions for Couples

Now, here is the third—and likely the naughtiest—section of questions. These are for couples who have made their twosomes official with quite a few rounds of joyous bedroom gymnastics (performance scoring optional), but even a year in, they are always keen to learn more and more about their partners in order to keep the flames burning between them, let alone make the resulting event a personal Olympic sport.

For these questions, we’ll mention whether it’s a query from female-to-male, male-to-female or if either one can ask.

1) Have you ever purchased a sex toy? If not, would you want to?

Who asks: Either partner.

Believe it or not, sex toys can really spice things up between you, so this is not a question to be missed, and there are plenty of websites to grab some sex toys and to explore, so have fun!

2) Say I told you I liked certain types of pornography or erotica? Would you watch/read it/act it out with me?

Who asks: Female-to-male.

There’s still a certain stigma against pornography and really explicit written erotica, especially concerning the idea of women enjoying it, as if they’re still supposed to act perfectly virginal and prudish about the whole thing.

If your tastes—and beliefs--fly in the face of conventional attitudes, why not use this question to stay connected to your partner in ways that other couples might struggle with? Mind you, your guy might not go for the “50 Shades” stuff as much as you might, but if you try something and find out that you’re both into BDSM in general, and that’s become part of what turns you both on, more power to you both for figuring it out.

3) What do you think about the Kama Sutra? Do you think it’s just a bunch of spiritual “mumbo-jumbo” paired with sex positions, or do you think it has true spiritual merit?

Who asks: Either partner.

You’ll have to know your partner really well in order to ask this question. Of course, if you were already aiming to find a lover who felt the Kama Sutra has deep spiritual merit, and you’re currently with them, well, the question is a moot point, isn’t it? But if you and your beloved are only maybe six months to a year into your togetherness, this is a worthy question to ask, concerning both sexual and spiritual compatibility.

4) What is the one thing you really love for me to do to you in bed?

Who asks: Either partner.

This question is probably one of the best for either partner to ask each other. It pushes both to be open and honest, to say nothing of perhaps starting up a frisky game of “show-and-tell.”

5) We’re headed out on a really nice dinner date, and I can’t quite decide what to wear, and I ask you to pick something out for me. What is the one outfit you’d love to see me in?

Who asks: Female-to-male.

Gentlemen, if you’re reading this, this is your chance to tell the truth about which outfit you’d pick. Don’t just say “You look good in anything.” Be specific, especially if what you’d really want to see her in is quite racy, but still suitable for going out.

6) What sort of dancing would you want to see me do: Traditional burlesque striptease complete with feather boas and long gloves, or bellydancing, with a sexy bellydancing outfit and Middle-Eastern music?

Who asks: Female-to-male.

This is a somewhat quirky question to ask, but if you’re a lady who not only loves to dance, but also likes the idea of putting on a personal show for your guy, then you’ll definitely want to get your guy’s thoughts on the matter. Whether he chooses one over the other, or gives you the option, you’re likely to blow his mind either way.

7) Would you want to have sex outdoors? Why/Why not?

Who asks: Either partner.

Now, this might seem like a question to ask in the slightly earlier stages of dating, say, around the six-month mark in the middle of summer when everyone’s thinking about camping out.

But let’s face it: not everyone reveals everything at once. Not even during those seven-hour-long conversations you have right at the beginning of a relationship, let alone those really deep conversations you might have in the middle of a truly intimate partnership.

Sometimes, a question like this can be quite surprising and interesting, especially if the only sex you’ve been able to have, so far, has been indoors, and neither one of you has given a whole lot of thought to the matter of outdoor sexy shenanigans. Just be sure to add the “why/why not?” to your query, or else the conversation won’t be as open-ended, and you’ll either get a “yes” or “no” that might come from very little thought at all. And the whole point of these questions is to provoke thought and discussion, let alone a bit of “getting busy.”

8) What’s the hottest fantasy you’ve ever had?

Who asks: Either partner.

Okay, so this question sounds typical, even cliché, but it can actually open up doors to further intimacy, both emotional as well as sexual. After all, this sort of question requires a certain level of trust that slightly more established couples tend to have, as opposed to people who’ve only been dating maybe one to three months.

9) Be real now: Which do you prefer being, the dominant or submissive?

Who asks: Either partner.

Thanks to the “50 Shades” phenomenon, which has opened the floodgates for BDSM to be part of the collective conversation about sex, a question from one partner to another about whether they prefer being dominant or submissive is going to come up sometime, and it might as well be now, whether you watch “50 Shades” together or not.

Such a question could not only lead to sexy times, but deeper conversations about your own beliefs, hangups, etc around anything that you might deem as “kinky,” and whether or not you’d want to let go of such hangups and try something out just once, even if it’s just taking a page from Christian Grey’s book and using a silk tie for light bondage.

Yes, these questions were divided up between the three sections, but they do total 21. Of course, there are many, many other questions you can find out there to ask your partner, and there are some questions that you can rephrase or take inspiration from to create your own questions, if you don’t want to feel like you have to “stick to a script.”

Ultimately, take these questions, print them out, or read them off from the webpage to your partner, whether over a meal, or after dinner when there’s time for the pair of you to snuggle up on the sofa with your tablet or phone and have a sexy, heart-to-heart conversation...which could easily lead to some lovely skin-to-skin contact.

In another article, I will be going into freaky questions to ask your boyfriend and freaky questions to ask your girlfriend to you and your boyfriend connect on a deeper level while having fun together. If you would like to see such article, please leave a comment below it really means a lot to me thank you.

Photo Credit: Christof Timmermann Flickr via Compfight cc


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