15 Freaky Questions To Ask Your Boyfriend


Sometimes you have to make the first move if you want to get him to take off his boxers and that is why there are freaky questions to ask your boyfriend. Of course, those don’t have to be dirty questions but still, they can be the dirtiest you can think of. I will give you my choices of freaky questions to ask your boyfriend but they can be anything you want them to be… from, “Would you rather have a threesome or be with a porn star?” to, “Which part of my body do you like best?” The possibilities are endless.

Some of these freaky questions to ask your boyfriend are great conversation starters for when you’re on your first date. Others are, however, for when you have been in the relationship longer. In any case, freaky questions to ask your boyfriend will help you get to know him better. You will get to find out about his turn-ons or the craziest thing he has ever done. From the first time you ask your boyfriend dirty questions, he will want to hear more of them and some of them are perfect for turning texting into sexting. Don’t be shy and ask him for naked pictures or ask him about his sexual fantasies.

Your boyfriend might be dreaming of the moment when you’ll ask him to introduce dirty talk, sex toys, or edible underwear into your sex life. Don’t be surprised if a dirty truth or dare leads to foreplay, so make sure you’re wearing your sexy lingerie. Dirty questions like, “What is your favorite place to have sex?” and, “What is your favorite position?” and, “What is your favorite thing about sex?” will help your sex life. It’s a great way for you to make the first move and initiate foreplay. His boxers will fall right off when you ask him some of these freaky questions to ask your boyfriend. So, let’s see what sexy questions I have prepared for you.

15 freaky questions to ask your boyfriend

1. What is the most interesting sexual experience you ever had?

Now, this is a question that’s one of the great conversation starters on a first date. Maybe the craziest thing he has done is have sex in a public place or have a one-night stand or maybe he had a threesome or has been to an orgy. You can ask him other naughty questions such as what is the weirdest place he has done it. Try asking him about the number of times he has had a one-night stand to better understand his sexual experiences.

However, you can keep it clean and simply ask about his first kiss or the first time he slept with someone. You might get to have your first kiss with him that very night. Of course, you could also ask him about the number of times he has been to a strip club and if he has ever gotten a lap dance. If you’re feeling dirty, ask him, “Would you rather get a lap dance in a strip club or from me?”

2. What is your biggest sexual fantasy?

Freaky questions to ask your boyfriend about his fantasies will instantly get him to think that you will make them come true. Maybe he’s dreaming about an orgy with a porn star or he just wants you to ask him for a quickie in edible underwear. You’ll never know unless you ask him some dirty questions. Ask him about the weirdest place where he would like to do it or ask if he would like a quickie in a public place. These sexy questions will get him to tell you his turn-ons and his favorite place to do it.

You can also ask him if he would like to be in an open relationship. This is a good question for a dirty truth or dare, but be prepared that he might want to be in an open relationship with you. You could ask him dirty questions about the hottest thing he would like to do to you or tell him about the dirtiest thing you would like to do to him as well. Ask him if there are any sex positions he has been meaning to try but hasn’t had the chance yet.

3. What is your favorite part of my body?

Turn texting into sexting by sending him naked pictures and then ask him about his favorite part of your body and the hottest thing he would do to you. Once he tells you which part of your body he likes, you can send him dirty pictures of that favorite part. Freaky questions to ask your boyfriend include asking him about his favorite part of a woman’s body in general… Is he a boob guy or a butt guy?

Give him a task to come up with sex positions where he can enjoy that part the most. Your dirty pictures will get him to think about his favorite position anyway so why not ask him about his favorite position as well? Or you can change the topic by asking him what his favorite thing about you is. Make sure to buy lingerie that will highlight the part of you he likes best.

4. What is the dirtiest thing you have been meaning to try with me?

This is one of the naughty questions that will get you prepared for what’s coming. Maybe he has some sex toys he would like to try with you. He might simply want to go skinny-dipping with you just to get you out of your lingerie. If he has never gone skinny-dipping, this is your opportunity to create some memorable moments in your relationship.

There is one thing I figured out and have to tell you – guys love dirty talk! So maybe that is exactly what he has been meaning to ask you. More dirty talk will really spice up things in the bedroom, and these dirty questions are a great way to practice it. While you’re at it, ask him about the last time you two made love as well. You can use flirty questions such as, “Would you rather repeat the last time or try something new?”

5. Who is the sexiest woman in the world in your opinion?

Flirty questions about the sexiest woman will tell you about the type of women he likes. Maybe he likes some movie character that you can dress up as to fulfill his dirtiest fantasy. But, let’s face it, he will probably say that you are the best woman in the world to him. That way, he will deserve you doing the dirtiest things to him.

6. What is your dirty little secret?

You want your boyfriend to open up, and dirty questions can help you with that. Ask him to tell you his dirty secrets, and you’ll find out something new about him. Being open in a relationship is what matters the most when you are searching for someone you’ll spend the rest of your life with. But even if you aren’t, it’s great to find out what he has hidden from everyone. It will certainly get you to find out more about him and see what he is like on the inside. If he tells you his secrets, it’s a sign that he trusts you, and that is always good for a relationship.

7. Do you get jealous when I talk to other guys?

Not all questions have to be dirty… some of them could simply serve the purpose of getting to know each other a little better. Is he the jealous type? This is certainly something you need to know about before you hang out with your male friends. While you’re at it, you can ask him if he likes it when you get possessive over him. Tell him about how you feel when he talks to other women. Be honest with each other, because if there’s anything wrong, you can work on it.

8. Were you ever thinking about someone else while we were making love?

This is a very intriguing question, so I couldn’t resist mentioning it here. Still, ask yourself first if you want to know the truth. The truth is that he probably has but he will never mention it in a million years. Of course, you could try telling him that you have to get him to be honest with you, but he might get mad that you have instead. Don’t worry, you can change this question to, “What are you thinking of when we are making love?”

While you’re at it, why not ask him about what he’s thinking about when he is masturbating as well. You will get to hear a lot about how you are the only thing on his mind. Those dirty things that he thinks about, you can make them come true for him. So, this is definitely one of the more useful dirty questions.

9. What turns you on the most, and what is your biggest turn-off?

Sure, you can ask this when you’re first starting to date someone, as it will certainly help you find out what they like and don’t like. You can ask him for specifics and turn the conversation to what he likes and doesn’t like about you, as it would be great to find that out. Try asking him about what piece of your clothing turns him on the most or you can ask him to be specific about what he likes and doesn’t like in bed. Such questions might include if you like your hair pulled, whether you like it rough or sensual, whether you prefer to give or receive…

10. How many single girls’ numbers are in your phone?

Now, this is something you want to know about but be prepared that you might not like the answer. Still, you can continue by asking, “How many of them have you slept with?” But be careful with these questions because a guy will never enjoy telling his girlfriend about other girls in his life. However, it is a great question to ask when you are playing truth or dare. After all, you can always dare him to delete those numbers.

11. What would you like me to say to you while we do it?

As I mentioned before, a lot of guys dream of having a girlfriend who knows how to talk dirty to them, so, this question is the best way for you to find out what he would want you to say to him while you’re doing it. It will make things easy for you, as all you’ll have to do is repeat what he has told you. That’s a great way to start using dirty talk in bed and you will get inspired to come up with your own things to say to him that will turn him on even more.

12. Does the thought of recording a video turn you on?

This is a question for a long-term boyfriend whom you trust completely. Let me tell you something, every man is turned on by the thought of recording a video. Still, you can’t do such a thing with someone you don’t know very well. You don’t want him to use it against you if you two break up. Still, there is a solution if you still want to do it with him. Make the video at your place with your device, and don’t let him have it until you have been with him long enough to trust him. If you are already in a long-term relationship, this question is great because making a video could really spice up your love life.

If you have decided to make a video with your boyfriend, let him know about it by asking this question. Then have him come up with the ‘screenplay’ and what exactly you two are going to do in the video. This will keep him occupied, and he will be looking forward to the moment so he will be able to truly appreciate it. Have him come up with other fun things that you can do in the bedroom that will spice things up.

13. Have you ever cheated or been cheated on?

This isn’t a dirty question but it will tell you a lot about a guy. After all, if he has been a cheater, it’s good to know what his reasons to cheat were. In the other case, if he has been cheated on, it might have left permanent scars. It’s important for you to know where your boyfriend stands when it comes to infidelity. His opinions about it will help you get to know him better. Unfortunately, if he had a tendency to cheat in the past, it is very likely that he will cheat on you as well so this question could open your eyes to if your Prince Charming is actually quite a ladies’ man.

14. Do you have a name for your package?

A lot of guys have a name for their package. Still, all of them will let you name it and he will want to give a name to your lady parts as well. It’s a fun thing to do on a lazy Sunday. What’s great about it is that you will have your own inside joke that only you two will know about, and it will make your bond stronger. This kind of playfulness is healthy in a relationship and it reminds us to have fun.

15. Have you ever bragged to your friends about me?

Wouldn’t it be fun to find out what your boyfriend says to his friends about you? You want to know if he is really proud of calling you his girlfriend but it’s also fun to find out if he has been sharing the stories about your sex life with others. All men brag about getting a hot woman in bed with them so don’t be surprised if his friends have heard about how good you look when you’re naked. After all, girls talk about sex all the time, and they gladly share their experiences. Men are no different, so get your guy to tell you all about what he has been saying to his friends about you; it will be fun!


15 Freaky Questions To Ask Your Boyfriend