I Let Total Strangers Ask Me Any Question About My Sex Life

Sex Machina isn’t a sex column in the traditional sense because I don’t have as much sex as you probably think I do (I’m talking to you, man who commented “lil slut ;/” on a recent Instagram photo). I’m too lethargic to figure out why there’s a spoon in my pillowcase, let alone track down someone who interests me long enough to let them inside me. On the instances I do feel energized enough to get it in, the sex isn’t what you might call “great.” It’s also not an advice column because I believe people who thought the word “vagina” was actually “bagina” until age eight should be disqualified from offering sex tips.

Yet having written more articles about sex than Hail Marys my grandmother has said for me, I know a lot—and maybe too much—about people’s sexual habits, pet-peeves, desires, and failings, and I’ve also gleaned quite a bit of wisdom from the reasoned advice of sex therapists and coaches, adult film stars, and the Italian men in my DMs. For this reason, I now feel compelled to shout my earned knowledge from the rooftops, which, if nothing else, could help lighten my own personal burden of carrying the world’s dick stories on my shoulders. So, for the first and last time, I let readers anonymously send me their burning questions pertaining to my sex life or the craft in general by using the site Sarahah. l answered 18 of the most grammatically correct, least abusive questions I received to the best of my sexpertise.

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1. What do women really think about sucking dick?

It’s very boring to administer.

2. How weird is it to be very into the thrill of maybe getting caught having sex in public, but very not into actually getting caught?

This fantasy is very common, and yes, many people share your trepidations about getting arrested.

3. If you’re going down on a girl on the first date, should you ask before eating her ass or just go for it?

Ask her; always ask her. Always. Ask. Her.

4. How do most women feel about men having a foot fetish?

Most women I know don’t mind indulging the occasional partner’s foot fantasy, though I have yet to meet a woman who seeks this out or is, herself, stimulated by jerking a man off with her toes. But one thing I do know is that all things are possible and have happened thousands of times.

5. How often do you masturbate?

A few times a week. The exact number varies based on how depressed I am, or whether I’ve lost the charger to my vibrator.

6. Whats the naughtiest thing you’ve done, in detail?

Once I ate a loose Twizzler I found in the back seat of an Uber and didn’t even notice until someone pointed it out.

7. If you’re going at it for the first time, how much more difficult is it to be on top? It sounds like there’s some expectation of knowing what you’re doing to be up there.

I like being on top because I can control the rhythm and angle; however, I can neither confirm nor deny whether I “know what I’m doing up there.” To my knowledge, I don’t have secret moves that drive him wild, but I do have not-so-secret moves that drive me to orgasm, which at the end of the day, is the reason for the season. To answer the first part of your question, though: yes, being on top poses some challenges, regardless of whether or not it’s your first time with a partner. Supporting yourself upright and working against gravity—rather than lying comfortably on the bed as you would to watch viral Chinese cotton candy videos or replay break-ups in your head—takes a toll on the sedentary.

8. A recent episode of Insecure explored the feelings of shame/embarrassment/betrayal Issa experienced when her partner unexpectedly came on her face. Any thoughts on the cum on the face/body stigma? How would you/have you reacted to such requests or surprises?

Do I have thoughts!? Do I ever. I’m still bitter about the Croatian man who came on my face without asking, then ate two (!) bowls of fragrant beef stew before driving me home. Always ask. I’m very lenient! There are all sorts of mutually-agreed-upon places where I permit cum, but only if you loop me in first. This is a cheerocracy. Everyone must work together.

9. I am crazy for you.

I feel like my prompt was pretty straightforward.

10. What about rimming?

What about it? Do I like it? No. Do people? Yeah.

11. Do we believe the cultural suspicion that men who like a finger in their asshole may have homosexual leanings, or is this equally enjoyable to men of different sexualities? (Asked by a straight woman who is genuinely curious.)

While most men I’ve been with expressed zero interest in my interacting with their assholes—to the point where if my hand grazed the area, they’d say “woah woah woah!”—many men of all sexualities appreciate a finger in the butt. The superb 2016 article, “Let’s Be Honest, Straight Guys: We All Like Butt Stuff,” unpacks this desire (and the shame surrounding it) really well. At the end of the day, prostate stimulation generally feels good! Here’s a choice quote from one of the anonymous straight men cited in the story: “Playing with the butt-hole is pretty cool, mainly because it feels nice. And who doesn’t want to feel nice? There are people out there who think sliding your thumb into a nicely lubed-up asshole is for gay people, and maybe it is. Gay means happy, right? Because that’s exactly what I am when someone’s rumping-and-pumping or slowly tickling the inner-walls of my rectum.”

RUMPING AND PUMPING.

12. How did you learn about masturbation and start doing it?

Rarely do parents or sex educators sit girls down and say, “Hey, this is masturbation—it feels good and it’s not weird.” Many girls don’t know what masturbation is the first several times they masturbate. They just rub up on chairs and are so in the zone that they don’t notice the discomfort of house guests, family members, or classmates. Only later do they find out they were masturbating, and that maybe they shouldn’t in public.

I was fortunate enough to grow up in a household littered—just absolutely littered—with Dr. Ruth’s entire oeuvre, so I knew what was up.

13. Have you ever tried anal? What are your thoughts on anal?

For me, anal was excruciating, but if I were with someone I trusted who wanted to try it again, I’d be open to it. This butt plug was nice.

14. How do you navigate what might be called “esoteric turn-ons” with a new partner? I’m not saying it’s magic tricks, like look-where-I-found-a-quarter magic tricks, but for the sake of argument.

With compassion and honesty.

15. Hi. Just wanted to ask if you’ve ever been with a Nigerian before? If not, I live in London and would love to ask you out for coffee.

I have not! I also don’t have any plans to go to London any time soon, but be well.

16. Strangest thing you’ve masturbated to or with?

I’m reluctant to call this “strange,” but there’s a life-size cardboard cut-out of Drake in my bedroom that … has certainly played its part.

17. Best orgasm ever?

Earlier this year, I was tangled in a strange but ultimately magical configuration with a man I was seeing. While inside me, he rubbed my clit with his finger, and it worked out well.

18. I just read your article, “What Happened When I Tried to Get Laid on LinkedIn ” on the VICE website. I was amused by the content. With a smile on my face I was thinking, Why is someone looking for sex on such a platform like LinkedIn? But actually, I’m wondering whether you as a sex columnist never have shame on yourself?

Nah.

Questions have been edited and condensed for clarity.

Sex Machina is a very personal column exploring the intersections of sex, romance, and technology.