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Porn Star Advice: Getting Real About Orgasms With A Concerned Boyfriend

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Photographed by Signe Pierce

Kayden Kross answers all your important, sexy sex questions

As real-life, fully-certified porn star Kayden Kross says, “You can’t faze me. After all, I’m a notably awarded citizen, and 30 million eyeballs have interacted with my butthole.” Indeed, we’ve tried. Thus, we’re proud to have her as our official sex columnist. With her huge collection of experience-backed tokens, Kayden will be lobbing her left-fielded, unsubstantiated advice straight at the level of your forehead... well... only with your consent, of course. To get your question seen (and possibly answered), email Kayden@Nylon.com. Now, let the oversharing begin.

Question: I am in a loving, committed relationship with an amazing girl. We have sex all the time, and we both enjoy it, but she has never had an orgasm in her whole life! She loves to rub herself, but at a certain point she always stops and says that her hand just can't keep going. And she also loves it when I rub her clit, but at a certain point, she starts thrashing violently and yelling at me to stop. I asked my guy friends but they didn't know anything, and I don't want to embarrass her by asking her female roommates.  This is my first serious relationship so this is making me feel a little insecure. Even worse, she tells me that she has kind of just given up on herself! What can I do to help her? Should she see a doctor? Any advice would be greatly appreciated.

Thanks,

Concerned Boyfriend

Answer: Greetings, Concerned Boyfriend. Let me begin with a blanket apology for answering your questions with more questions while at the same time taking a stab at the answering part. You see, there is a significant portion of the female population that reports never having had an orgasm (some say as high as 10 percent, though I’d argue that there’s a bit of a reporting bias in all surveys sex-related). Of that breakdown of nonorgasmic women, some are simply not being provided with fertile orgasm ground, and others probably should see a doctor. I’m a terrible doctor, as evidenced by my nonexistent medical background, but I have a few things to say about fertile orgasm ground. I am, after all, paid to have them.

The thing you should be focused on is not the orgasm. An orgasm is the final destination of a journey if you will, but the actual work begins with arousal. That’s your footpath. You don’t expect your girlfriend to come in and immediately take you from flaccid to Jizztown without lending some love to building you a boner in between, do you? Of course not. That would be silly. But a lot of men come at a clit assuming that it’s immediately ready to be rubbed hard and fast without any foreshadowing. Have you ever tried to jerk your limp dick off hard and fast? Looks like you’re trying to throttle one of those blow-up tube men at your local car dealership, doesn’t it? Clits and dicks function in much the same way. Even the cells they begin as in the womb are the same. For women, it’s easy to know when to pick up the pace on a penis, because we can see the bright flashing signs of physical arousal in the form of a boner. The clitoris doesn’t send such raging signals. But regardless of whether you can see it, there is a difference between a clitoris that is aroused and engorged with additional blood flow, and one that is in hiding because what’s going on doesn’t interest it. The lesson: Don’t run in hard and fast on a clitoris. And once it is engorged, you still don’t want to do that. Women have twice the nerve endings in that tiny spot as men have in their penises. We feel a fuck lot down there. Too much stimulation too fast can chase the sensitivity away rather than bringing it closer. In my experience, there is absolutely a point of no return with regards to overstimulation. Once I reach it, I know I won’t be having an orgasm in that particular setting. I invariably opt to pack up my goods and go away.

I treat the female orgasm in much the same way survivalists treat starting a fire. There are sometimes a lot of false starts before you see smoke, even for the most woodsy types. There are also sometimes rainstorms that are evidence of the universe being stacked specifically against you. Do not despair. The universe will get bored and go away if you don’t engage with it. Do not let it believe that you are under any sort of time constraints as you try to start your fire. Do not let it know that you are frustrated when you do exactly what you’re supposed to do, and the fire still doesn’t start, and especially, no matter what, do not lead the universe to believe that your success or lack thereof in any way weighs on the state of your manhood, ego, or relationship. If the universe or your partner believes that any of these things hinge on your ability to rustle up a female orgasm, then you may very well be scaring it further away rather than bringing it closer.

Okay! Now that we’ve covered the part about checking your ego at the door, let’s talk about blood flow. Orgasms and blood flow go hand in hand. If you don’t believe me, ask your raging boner next time it comes around. Women parts also engorge with blood when aroused, though there is a little more mystery there, as evidenced by Pfizer’s complete lack of female Viagra options. What you want to maximize in that region, beyond that magical combination of comfort and stimulation, is blood flow. Have her lie on her back and then have her flex her muscles like her life depends on it. I mean really flex those fuckers. This is a tummy, thigh, and ass workout too. Think heavy breathing and elevated heart rate. Bonus points for a fine misting of girl sweat. I call it masturbatory planking. This is a tried and true method that I practice in my personal life, as well as on-screen. In fact, the easiest way to tell if I’ve faked an orgasm or not in any of my scenes is to simply look at my legs. If they are in a position where I was able to flex them stick-straight, the orgasm was real. If they are bent in any way at all, you’ve merely witnessed some very fine adult acting. Blood flow is why. So make her hold this masturbatory planking for as long as she can physically hold it while she uses her own hands (or a vibrator—I personally don’t like vibrators but they definitely solve the problem of a tired hand) to try to feel out that orgasm. If she catches the wave, her body will very likely continue that flex for her. I love this part because it’s like I went to the gym, only I didn’t hate every minute of it. She may not catch the wave the first time, or the fourth, or the tenth, but she’ll know when she’s on to something because the work involved in getting there will stop being a conscious effort and start feeling like an intuitive pull. 

I do wonder whether the issue is not so much an issue at all as much as it is a very new world for one or both of you, though. You mentioned it was your first serious relationship. Is it hers as well? Is sex new to you both? I was having sex regularly and enjoying the hell out of it for a full six months before I was able to actually orgasm from it. It just took that long and that much experimentation before I could find the right combination that would spring the lock. Regardless of how much or how little experience each of you has, DO NOT ask her roommates about it. This issue is hers and hers alone to decide who to bring it to and who not to. If she wants advice from her roommates, she will ask. The last thing you want is for outside people to get involved and only add pressure or negativity to an experience that is privately hers. Don’t ever forget that the experience of sex as a man is wholly different from one as a woman. Men are socialized to believe in their right to have and enjoy sex. Women are socialized to believe that they should be discriminating and private in that matter. She is fighting an uphill battle on the road to sexual enjoyment that you very likely know nothing about. Do not make decisions for her. That is not within your rights or your wheelhouse.

While I would bet, based on the small amount of information you’ve given me, that this is something that will work itself out in time, there is no reason to avoid asking a doctor to look at possible underlying medical problems. Low hormonal balances can wipe a good orgasm off the face of the earth, as well as a number of other things. But in the meantime, take your time with her, continue to experiment to find things that you both enjoy in bed, and remember that maximum sexual enjoyment—for both of you—is often just a matter of time and practice.

Photo by Handout / Getty Images.

From selling probiotic supplements to picture frames and umbrellas

A Kardashian-level of success doesn't happen overnight, and it certainly doesn't happen without proper planning. Kim Kardashian West clearly knows this because, according to TMZ, she has already filed for trademark protection on the name of her two-week-old baby, Psalm West. From personal appearances and entertainment services to probiotic supplements and scrunchies, she is leaving no stone unturned in terms of possible business opportunities.

Apparently, all of the Kardashian parents file these kinds of trademark protections for their kids even if the businesses never come to fruition. It's done as a precautionary measure to keep others from profiting off of their name and to make sure that, should they ever want to start a business, they don't have to worry about someone else getting to it first. The sheer length of this list speaks to the huge earning potential of baby Psalm, who can't even control his own neck muscles yet, let alone go into business. Still, this brings a whole new meaning to "securing the bag."

Below, a list of all the things Kardashian West is seeking usage rights for.

Hair accessories

Barrettes

Bands

Bows

Clips

Ties

Ornaments

Pins

Scrunchies

Chopsticks

Twisters

Wrap

Hair extensions

Ornamental novelty pins

Entertainment services

Personal appearances

Skin care

Probiotic supplements

Toy figures

Doll accessories

Computer software

Clothing

Baby bottles

Furniture

Strollers

Beverageware

Swaddling

Blankets

Skin moisturizers

Lotions

Creams

Bubble bath

Fragrances

Body powders

Shower gels

Body oils

Skin serums

Nail polish

Nail polish remover

Nail care preparations

Puppets

Puzzles

Toy jewelry

Toy cameras

Toy food

Bath toys

Baby gyms

Playground balls

Electronic action toys

Baby bouncers

Baby changing tables

Baby walkers

Pillows

Mirrors

Cushions

Picture frames

Playpens

Baby carriers

Cosmetic bags

Toiletry cases

Duffle bags

Umbrellas

Clocks

Watches

Key chains

Calendars

Books

photo albums

Stationery

Stickers

Writing utensils

Collectible trading cards

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FROM THE WORLD WIDE WEB
Photo by Pascal Le Segretain/Getty Images

Well, actually it's crocodile, but she looks out of this world so...

Winnie Harlow walked the Cannes red carpet on Wednesday on her way to a screening of Oh Mercy!, wearing a showstopping gown.

The sheer black dress featured green embroidery on the front and back, which Ralph and Russo confirmed was in the shape of a crocodile. She belted the dress with a black crocodile skin-like belt and finished the look off with some strappy heels. She didn't leave it at just that. For beauty, Harlow packed on full lids of sparkly purple eyeshadow. She kept her hair sleek and simple.

Photo by Pascal Le Segretain/Getty Images

Though the brand says otherwise, as Game of Thrones fans, we'd like to think the embroidery is reminiscent of a dragon's skin. Not to mention, Harlow looks out-of-this-world beautiful in it.

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Photo by Andreas Rentz/Getty Images

That denim kimono!!

Marion Cotillard shut down the Cannes red carpet on Wednesday at a screening for Matthias Et Maxime. Instead of an extravagant gown that's expected of the event, Cotillard wore a matching black crop top and shorts. Despite wearing an outfit I typically don to a hot yoga class, she looks incredible. She completed the look with an oversized denim kimono, a statement necklace, and heeled booties.

Photo by Andreas Rentz/Getty Images

At first, I was drawn in by the crop top and hotpants duo, but, after looking closer at the kimono, it's clear that it's the real scene-stealer. The floor-length Balmain piece was decorated with artful rips and dragon motifs. I would like to live in it.

Photo by Pascal Le Segretain/Getty Images

Let's all bow down to the Khaleesi of Cannes.

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Photo by Frazer Harrison / Getty Images.

"It doesn't make you weak to ask for help"

Singer Billie Eilish is continuing to open up about mental health, this time in a new PSA video in partnership with the Ad Council and Seize the Awkward.

In the video, Eilish insists that "it doesn't make you weak to ask for help." She doubles down on the importance of asking for help, and stresses the importance of friends and family being there when their close ones reach out and checking in on them as well. "You should be able to ask anyone for help, everyone has to help someone if they need it." According to Eilish, there have been times when someone reached out to her at the exact moment she needed it, and it helped.

It was particularly refreshing to see Eilish acknowledge that there are things she still doesn't know and has to learn about her mental health. At the very beginning of the video, the interviewer asks her to reflect on her mental health journey, and all Eilish can do is let out chortle. "I think when people hear, 'Remember to take care of your mental health,' they think that everyone else is, and that is not at all accurate," she admitted. "You know, for me I'm trying to learn still to make sure that I stay okay."

Check out the PSA below.

Billie Eilish On Mental Health & Friendship | Ad Council www.youtube.com

Photograph via @kimkardashian.

"#NotOnMyMoodBoard"

Kim Kardashian has definitely been accused of borrowing a design now and then. But when Instagram influencer and Kardashian look-alike Kamilla Osman claimed the entrepreneur copied her birthday look for a Met Gala after-party, Kardashian was not going to let it fly—and shared plenty of photo evidence to shut down the claim.

Fashion industry watchdog Diet Prada first noticed Osman's claims on Instagram and shared side-by-side images of Kardashian's Cher-inspired outfit designed by Mugler and Osman's dress. "Never get confused with who 'inspires' who. They won't give you credit but they will copy," Osman wrote on her IG story. "I designed this dress for my birthday last year. Nobody had a dress like this was an original design."

Kardashian responded by posting the true inspiration behind her look: images of Cher, in similarly sparkly, plunging-neckline dresses and wigs, and of model Yasmeen Ghauri walking a Mugler show in the '90s. In fact, the only similarity between Osman's and Kardashian's looks is the bodycon mini-dress style, which the two are not the first to wear. Among the images, Kardashian included a blank slide with the hashtag "NotOnMyMoodBoard," making it clear that this was in response to Osman's claims.

Screenshot via @KimKardashian Instagram Stories

Screenshot via @KimKardashian Instagram Stories

Though I am with Kim on this one, Kardashian does have a history of co-opting other people's work. From being sued over her Kimoji app, to claims she copied makeup palettes and perfume bottle designs, to being accused of copying Naomi Campbell's entire style, it's far from the first (and probably, far from the last) time Kardashian's name will be mentioned like this.

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