Whether it's your first time or your 500th, sometimes sex can throw you for a loop. Sometimes that's part of the fun; other times, you're left scratching your head. Luckily, our resident sexpert Karley Sciortino — AKA Slutever — is here to help. Got a sex question for her? Email her at slutever@jezebel.com.

I'm a 26-year-old European exchange student currently studying in the US for five months. I have a (relatively new) boyfriend back home who I'm totally into, and before I left we agreed to be monogamous. But now I have a dilemma: I love Chatroulette, and I usually skip over the random masturbating men, but recently I've been fantasizing about not skipping over the dicks and engaging in some hot, anonymous Chatroulette-cybersex. Would that be cheating? I want to think not, but I also realize it's different than porn — it's an actual sexual interaction with another human being. My boyfriend and I Skype sometimes, but it hasn't turned into Skype-sex. And besides, the fantasy is more about the anonymity of it. So: cheating or not-cheating?



Well, the concept of "cheating" is subjective, as it completely depends on the boundaries you've set with your partner. I realize that probably sounds like moralistic, guidance counselor speak — like as if any couple actually gets together and says, "Hey! Let's spend the evening drawing out a detailed map of our relationship's boundaries! BYOCrayons!" However, if you and your boyfriend engage in a reasonable level of communication, then you should hopefully have an understanding of what you both want and expect out of the relationship.

Think of it this way: some people (AKA prudes and religious freaks) think that simply watching porn is cheating. Others consider masturbation cheating, because they support that whole "But what were you thinking about?" argument. (Like as if anyone actually masturbates to the person they're dating—idiots.) Then, there are people on the other side of the spectrum—for example people in open-relationships—who are totally cool with their significant other taking part in the casual gangbang. Basically, when it comes to cheating, there's much room for interpretation. In my opinion, the best way to answer these types of moral questions is to reverse the situation in your head, and then think about how you would feel if he did the same thing to you. Would you be OK with your bf jerking-off with some random internet ho? I think the answer to your question lies in your response.


On another note: Bitch, you crazy. Why the heck would you agree to be monogamous with someone you just met, right before you moved to a foreign country for five months?! Five months is sooo long. I wouldn't be surprised if your vagina sews itself shut by the time you get back. You're in a new country, meeting lots of new people (AKA a new crop of human dildos), so why limit your potential experiences by devoting yourself to someone you barely know? Do you love this guy? If you do, OK fine, but if not I advise that you wait until your journey abroad is over before putting your vagina on a diet.

Ever since I started having sex I've always shaved my vagina without even thinking about it. It may look a bit nicer, but it's a pain in the ass having to plan ahead and make sure you're pristinely smooth every time there's the possibility of sex. I don't know if I'd like it grown out, but I think I want to try it. But I'm terrified the guy I'm sleeping with will freak out! It's my body so I can do whatever with it, but should I tell/ask him about it before the experiment begins? Where do you stand on the 'to shave or not to shave' debate?


Don't shave. Shaving is for girls in spaghetti strap tank tops who love tanning and have that mysterious type of hair that's like vaguely crunchy but also somehow permanently wet?? (How the fuck do they do that by the way?) Seriously, every time I see a completely shaved vaj all I can think about is the skin on an uncooked chicken leg—you know what I mean? Like all fleshy and raw, and covered in little bumps. That is not glamorous. When a guy looks at your vagina you want him to be thinking about a mysterious cave of unknown pleasures, not how good it would taste with BBQ sauce.


Shaving is OK for porn stars, because porn is exaggerated and separate from real life (i.e. a realm where it's totes casual to look into the depths of someone's gaping butthole), so it's OK for porn vaginas to be over-exposed and vaguely grotesque. That's hot in porn world. It's also fine to shave if you're a teenager, because teenagers are clueless and haven't worked out what looks good on them yet. (Also, teenage boys are idiots and generally can't figure out where the clit is, so it's probably best not to make things even more difficult with additional hair obstacles.) We all shaved our vaginas in high school, just like we all wore Uggs and got zebra stripe highlights and thought Kelly Clarkson had a "cool, funky style." But now we're older and wiser, and this sort of aesthetic ignorance is just unacceptable.

Do not ask the guy you are sleeping with about this, because his opinion doesn't matter. Listen to me, because I know everything: The premium bush style is a well-groomed triangle. Keep the hair around the lips too — why not? — but remember to wax your butthole for the love of god. For vagspiration, think 80s Madonna circa her Sex Book (#IconicVaj), 60s Jane Birkin (#VintageVaj), Chloe Sevigny (#IndieVaj), and Kate Moss (#ModelVaj). Basically, classy adult women do not shave their vaginas.

Dear Slutever, I am a 26-year-old boy, and though I'm not a virgin, I am terribly inexperienced. I've recently started seeing a girl (yay!), however I've been having a little ejaculation problem. The problem isn't that I cum too quickly, but rather that I stay hard all night and can't ejaculate! It's no problem for me to get hard, and stay hard, but it just requires too much mentally and physically for me to reach the point of orgasm. Am I not emotionally connecting? Is my problem psychological? Should I find some way to 'sensitize' myself?



There are lots of reasons why you might be experiencing jizz problems. Medically speaking, the condition of not being able to orgasm is called anorgasmia, and it can be brought on by a variety of factors. For example: a lack of comfort with intimacy or physical contact, past history of sexual abuse or trauma, disease, trust or communication issues with a partner, the use of SSRIs (commonly prescribed for depression), or — ta da! — anxiety. From what you wrote, it sounds like you're just experiencing some nerves. You've got virgin-vibes and are sort of freaking-out about it, but that's fine, because over time you'll learn things and gain confidence. And also, it's important to remember that you can still have sex that's hot and fun and rewarding, even without an orgasm. Duh, us girls do it all the time! (And we hate you for it.)

On another note, have you ever thought about just faking it? Under normal circumstances I would say faking orgasms is a bad idea — for both boys and girls — because you don't want to build a sexual relationship around something that's false. However, if the not-cumming thing is really stressing you out, then maybe pretending a couple times will help take the edge off a little bit. And who knows, maybe just knowing that you can fake it, as a last resort, will ease your mind enough that you'll be able to cum for real. (Although if you are going to fake it, remember to use a condom, otherwise your gf will be all like, "Uh, where's the smoothie?")


And lastly, this might be a shot in the dark, but your inability to cum could also be due to over-enthusiastic masturbation. Dan Savage talks about this a lot — about how over stimulation from watching a lot of hardcore porn, or from squeezing your dick too tightly while jerking-off, can lead to problems reaching orgasm when faced with an actual human vagina. In the words of Savage, you have to vary your routine: left hand, right hand, a little lube, a lot of lube, firm grip, loose grip. You don't want to ruin yourself for partnered sex by using the "death grip" — a fist clenched tighter than any human throat or pussy can clench — during solo sex.