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20 Make-Or-Break Sexy, Freaky Questions to Ask a Girl

Want a girl who’s a little racier in her sex life than the usual? If so, these freaky make-or-break questions will separate the vixens from the kittens.

sexy freaky questions to ask a girl

Most of us guys have, at some point or another, made the relationship sacrifice of spending months of our time and hundreds of dollars on wooing the object of our desires in a desperate effort to get to the end zone. How disappointing it is, then, when the woman you’ve spent so long fantasizing about turns out to have the sexual principles of a Victorian school headmaster?

If we’re brutally honest, most guys want the elusive total package: a lamb in the streets, and a tigress in the sheets.

When we find out that we’ve subscribed to a package that is the total opposite of that, we feel like we’ve wasted a lot of time on a woman who isn’t really what we’re looking for.

Freaky questions about sex to ask a girl

To avoid such wasted effort, the following freaky questions will help you find exactly the kind of sexual beast that you want. Refusal to answer indicates a no-goer, as does a bland and evasive answer. Just don’t blame us if you elicit an occasional slap or two along the way!

#1 How often do you masturbate? This is a question that most women simply HATE to answer. There seems to be such a taboo about female masturbation that they’ll go to all kinds of lengths to avoid it. Or worst still, they’ll just flat out deny ever having done it at all. However, if you elicit an unashamed answer along the lines of, “As often as I can,” then you’ve definitely found the right woman for your own particular brand of freakiness. [Read: Female masturbation: 17 facts about the naughty secret]

#2 Have you ever slept with another woman? This is pretty much every guy’s fantasy to witness or to be involved in, and her admitting that she’s already been there opens up all kinds of freaky possibilities. A definite plus.

#3 Which part of me would you want to sit on first? You need some nerve to ask this question, which rates highly on our “instant slap to the kisser” scale. However, any positive answer, regardless of whichever part of you she ends up saying, is a sign that you’ve scored yourself a true hellcat! [Read: 8 tips and tricks to give her oral like a pro]

#4 When was the last time you watched porn? Much like masturbation, porn watching for single women seems to have something of a taboo surrounding it. Any answer indicating that porn has been watched at any time is, hence, a good one. [Read: 10 good reasons why women should watch porn]

#5 What’s your filthiest fantasy? Again, it’s the admission of a fantasy that is more telling than its content, although one that is particularly dirty is practically a guarantee of freaky nighttime fun to come.

#6 Do you have a secret dirty move you’d like to try with a guy? Similar to the last question, this one focuses her attention specifically upon the male form and gives you an insight into how her filthy mind works.

#7 Are you noisy during sex? Far from being just a stereotype, a woman who makes as much noise during sex as a church mouse in slippers has all the passion of a gutted fish. You need a woman who screams like a banshee and isn’t afraid to admit it. [Read: Loud sex! – Is your girl really faking the big “O”?]

#8 Have you ever picked up guys just for sex? If the answer is yes, how about a follow up question of, “Want to do it again now?” A touch forward, but hey, that’s why we’re here, right?

#9 Do you swallow? The best kind of female lovers are the ones who get stuck in and aren’t afraid of the messy sensual side of sex. This question, therefore, is a crucial one to working out if she’s a sexual freak or prudishly meek. [Read: 9 sex requests your girlfriend is sick of hearing]

#10 Do you enjoy anal? This really is hitting the extreme end of the sexual spectrum, and if you get a woman who isn’t scared of admitting that she likes to give it a go from time to time, then you can be sure that there isn’t much she wouldn’t do.

#11 Have you ever done something illegal? This is question number ten, multiplied to an exponential degree!

#12 Are you shaved or trimmed? The question itself isn’t nearly as important as whether or not she’s willing to discuss her genitals with you. The woman who paints a picture of her bush *or lack thereof* is no Bambi! [Read: How to safely shave your pubic area: A guide for men]

#13 What’s your favorite position? The answer to this question can be misleading, as there’s no reason why missionary sex can’t be as passionate and fiery as any other. However, coming up with a position you’ve never heard of before *an “Atlantean piledriver”, for instance*, betrays her vast sexual experience and a mind that is as attuned to freakiness as is yours. [Read: 20 moves to last longer during sex without any difficulty]

#14 Do you own a vibrator? If she doesn’t just own one vibrator but actually has a whole drawer entirely dedicated to sex toys, then you know you’re on to a winner.

#15 Have you ever had a threesome? A good question to see how far she is willing to go, as well as to work out if there’s any chance that you might get into your own little sandwich with her at some point in the future. [Read: Threesome tips – 20 things to know before entering one]

#16 Have you ever done a Don Corleone? The infamous Don Corleone, waking up with a horse’s head on the pillow, describes that moment when you wake up from a drunken night’s reveling and find that you’ve taken home a woman of less than perfect appearance. Although never a positive thing, if she admits to having done the same with a guy, you know that she values sex over appearances… and that’s a nice freaky quality for a woman to have.

#17 If you were a hooker, how much would you charge per hour? Prepare for a slap that will send your face into next week when you ask this question. However, if a slap-less answer is forthcoming, even if only in jest, then you know you have someone on your hands who is very ready for action.

#18 Would you be bothered if someone watched us have sex? Not only have you slipped the word “us” into the question so that any affirmative answer subconsciously betrays the fact that she’s thinking of having sex with you, it also shows how freaky her sexual principles truly are. [Read: Real life dirty sexy public flashing confessions]

#19 Are you getting aroused by my asking these questions? Just to make sure that she’s truly getting into the swing of things and not just stringing you along or laboring under the misapprehension that it’s all some big joke, this question highlights exactly what it is you’re after. [Read: 20 dirty questions to ask a girl to make her wet]

#20 My place or yours? Taxi! [Read: Dating your one-night stand – Easy or sleazy?]

If a freaky sexual relationship is important to you when choosing a future partner, then put some of these questions to the test to obtain the girl of your wicked dreams.

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David Cullen
David Cullen
David Cullen is frequently described as erudite, insightful and witty – but only by himself and only after several large glasses of Rioja....