20 DIRTIEST Questions To Ask Your Boyfriend

You've always wanted to explore and find out if your boyfriend was freaky, well here are some questions to ask your boyfriend to get those answers.

By MJ Faublas
20 DIRTIEST Questions To Ask Your Boyfriend

I'll Tell You My Dirty (Freaky) Little Secrets....

So you and your boyfriend have been dating for, and you've been an open and honest girlfriend. You've shared so much with your boyfriend that you feel like he knows you like the back of his hands. When it comes to intimate conversations, you tell your boyfriend every little freaky detail about your wants, desires, and needs in the relationship. However, your boyfriend doesn't seem to share as many freaky details about himself as you'd wish. But you continue being the perfect girlfriend and tell your boyfriend everything as he holds all his freaky little secrets to himself. 

Understand that the time of being the perfect little girlfriend is over and now is the time to tame your boyfriend and get all the dirty little freaky secrets out of him. We'll steer the conversation, but you must deliver and get the freaky answers to your questions. We can only do so much, so get ready.

Getting Freaky with Your Boyfriend, What to Ask...

So, he knows you in and out. He knows how to play and manipulate your mind until you're spilling all your freaky answers to his questions. His questions seem to be kryptonite, and you're Supergirl. How does it do it, you just can't wrap your mind around his conniving ways. Well, here is your chance at getting some freaky little answers to your many questions. 

But remember, the goal of getting your questions answered with as much freaky detail as possible is to make your boyfriend comfortable. The mood will be created for you, and all you have to do is follow through:  

1. Make Your Boyfriend Comfortable

Make flirty suggestions about what he should expect on this special night. Be as soft and flirty as possible so that he will think he is in full control and is the man of the house. The more comfortable he is, the easier it will be to obtain answers to the many freaky questions you will ask your boyfriend tonight.

2. Feed Your Boyfriend

The best way into a man's heart is through his stomach, and the best way to his mind happens to be on the same route. Make some steak and baked potatoes, bring out that expensive bottle of wine. Let your boyfriend eat all he wants and watch him as his guards go down, and before you know it, you will get your questions answered in the most freaky ways.

3. Massage Your Boyfriend & Ease His Mind

Of course, your guy deserves a massage, so give it to him. Bring out some lavender oil to relax his mind. Pour more wine into his cup. And give your guy the most intense massage and watch him become putty in your hands.

4. Bring on the Comfort

Put on a movie that you know he won't be interested in and allow him to become as comfortable as possible. Bring out the blanket and caress his head, chest, and if needed, even massage his feet. The goal is to make him feel as comfortable and at ease as possible.

20 Dirtiest Questions to Ask Your Boyfriend

Now that you have him right where you want him to follow this blueprint to ask him the most freaky questions that you can think of. Be gentle and good luck:

1. Do you want to play dirty truth or dare?
       Of all the questions, this one will be the opener to get your boyfriend in the mindset of comfort and get you ready to ask the questions that have been plaguing your mind.

2. What do my lips taste like?
     This question requires your guy to dig deep into himself and allows him to be honest with you. The is the first of many freaky questions to come.

3. Have you ever wanted to sext me?
     Now you'll have him on the edge of his seat because depending on his level of freaky, he will want to answer more of your questions.

4. What's the one freaky thing you want to try with me that you haven't?
     One of the many questions to show him that you are open to being even more freaky with him. You're willing and able to explore your freaky side.

5. Would you like watching me touch myself?
     Now, of all the questions, this is the one you should be prepared to ask with confidence. If he answers yes, he will want to watch in the future; but if he answers no, well you're safe.

6. Do you like giving or receiving?
     This question poses a controlled answer when you ask it to your guy. If he prefers to give that will make you want to open up more, however, if he is a receiver, be ready to bring him into the giving light.

7. Do you like it rough or sensual?
    The answer to this question can be used later on when you two explore each other.

8. Do you like BDSM?
    This question can lead to your boyfriend wanting to explore BDSM. So be ready.

9. Do you think you can take my panties off with your teeth?
     The questions you ask will be actions your man take on you at a later date, so this question poses future response.

10. Would you like it if I pleasure you while we're on a long drive?
   This is one of those questions that will allow you to understand the sexual mentality of your guy. Be flirty when you ask this question. The goal here is to create an intimate connection that allows him to be comfortable enough to open up to you.

11. Do you own any toys?
  This question will allow you to see how far he's gone and how comfortable he truly is with his sexuality. If the answer is yes, your next move should be to ask if he'd like to use some with you. If the answer to your question is no, then maybe try to introduce him to the world of toys gently.

12. Under the sheets, are you Iron Man, The Hulk, Thor, or Captain America?
    Do whatever you feel with the answer to this question. The ball's in your court. laugh 
13. Have you ever had a naughty dream about another man?
   This question is important as it allows you to see how freaky your boyfriend really is. Ask this question with an open mind only.

14. Would you ever let me go down on you in a public place?
    This is a question that will create the scene in the near future. For example, if you're out after nice date night, you might suggest a quick stop by the beach and let your boyfriend fill your mouth for a few minutes.

15. Do you like it when I'm on top?
    If your boyfriend answers yes to this question, from now on take control of the bedroom and show him who's the real boss.

16. Do you think I'm a good kisser?
   Now don't go getting offensive if he answers 'no' to this question. Your next step should be to ask him to teach you how to perfect your kissing skills.

17. Where do you want to touch me right now?
    Be ready to let him explore that special spot.

18. What do you find sexy about me?
    And with that answer, your next question will have him ready for more fun.

19. Can I sit on you?
    If your guy was confused, he should have a clear understanding of what is next.

20. Can I kiss you now?
     Well, the questionnaire is over, go and have fun with your guy.

Questions & Answers

With all those steamy dirty questions answered, you should have no doubt in your mind if your guy is freaky. These questions were designed to help you get to know your guy in a more pleasing manner, so be as gentle as you as the questions and please keep your mind open to the answers you receive. You should be satisfied with the plan, question list, and the answers you receive. The final step is to follow through with the answers given.

Have some fun with your freaky guy.



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