My Wife and I Found a Wild Way to Include a Friend in Our Sex Life. But It Might Be Time for a Reality Check.
Our advice columnists have heard it all over the years—so we’re diving into the How to Do It archives to share classic letters with our readers. Have a question? Send it to Stoya and Rich here. It’s anonymous!
Dear How to Do It,
My wife and I had a threesome with a mutual friend a while back. It was fantastic, but we have no desire to repeat the experience, partly because we didn’t feel any physical chemistry with him. We’ve found a way to all enjoy each other, though.
We have our own private porn channel of sorts. We tease each other with GIFs, often of threesomes or moresomes. My wife and I often use it as foreplay, and he knows that and is happy to be included. Sometimes I even throw in a pic I’ve taken, or we’ll do a live video chat with him. He’s a voyeur, and we’re exhibitionists, and it plays to all our kinks, and we feel safe with him. We’ve gotten each other off quite a bit this way. Is this a healthy boundary? We’re far enough off in kink territory that I feel a need to reality-check.
Dear Three in Theory,
Your situation is so mired in mixed signals they’re even embedded in your telling of it to me, an innocent bystander. How can you have a “fantastic” sexual experience that is lacking in physical chemistry? That’s like taking a bath without getting wet.
Regardless, continuing to flirt with someone that you aren’t interested in having sex with again is essentially inviting annoyance and awkwardness. It seems quite likely that your spurned third will at some point request a repeat that you will have to turn down, probably in confusing terms (“It was fantastic! But nah … ”). I don’t actually see the boundary that you’re asking about, so I advise you to erect one that is more substantial. That said, if he’s aware and on board with the fact that you’re transitioning what was briefly a physical sexual relationship into a phone-based one, and he carries no expectations beyond those, I don’t see anything wrong with what you’re doing. Just know that without precise communication about what these exchanges mean to you (and what they don’t mean in terms of ever having sex with him again), you’re leading him on. And you wouldn’t want to do that, now would you?
From: I Live With Six Brothers. I Have Sex With Two of Them. It’s Fine, They Know. (Jan. 20, 2020).
Dear How to Do It,
I’ve been having a lot of casual sex recently, after moving to a big city with lots of humans around my age (I’m a 32-year-old heteroflexible woman) and accepting apps as part of my life. These experiences have been mostly OK, occasionally great, and occasionally terrible, as you might expect. Increasingly, I find myself “performing” being turned on to either improve or speed up mediocre or bad sex (secretly using lube so they think I’m wet, moaning, the usual stuff), and enacting other people’s fetishes and fantasies even if I pretty much already know they are not my thing (e.g. being submissive outside as well as inside the bedroom, told what to wear, told to video myself). I have a recurring thought whenever I’m performing in this way: “I could be getting paid for this.” My question is: Could I?
I live in the U.K., where prostitution is legal. I just don’t know how to become a sex worker. Am I too old? Am I being completely naïve? If not, where do I start?
I’m aware that in-person sex work would have to wait until after the quarantine, but I’d still welcome any advice.
I feel like you’re headed toward living out a modern and more liberated take on Belle de Jour, Luis Buñuel’s 1967 masterpiece in which Catherine Deneuve plays a housewife who becomes so obsessed with the notion of sex work that she just had to try it for herself. She found what you are likely to find: Part of what makes fantasies so exciting and gratifying is that they are, in fact, not real. It’s one thing to dream; it’s another thing to do. I don’t mean to denigrate sex work at all—I believe it is honest, necessary work. But it’s hard. You enter money into the equation, things become trickier. The person paying you for sex can easily assume a position of power, and part of the deal is for you to cater to his or her whims and desires. Of course sex workers retain their agency and their own power in many situations, but the transactional nature of these encounters means that you may find yourself in a gray area, performing things that you aren’t against, per se, but that you also aren’t inclined to do. It’s one thing to take it upon yourself to bluff your way through underwhelming sex, and it’s another to enter a contract that compels you to do so. It can really take a toll. And that’s to say nothing of the violence sex workers disproportionately experience.
Keep in mind that while sex work is not illegal in the U.K., exactly, much of what is associated with it is—pimping, running a brothel, and street soliciting are. (Online escorting is legal in the U.K.) I recommend watching this ITV report from January about the state of sex work there, which details the safety concerns that have many sex workers calling for legal reform. It may give your aspirations some needed perspective.
I want to tread lightly here and stop short of recommending you jump headfirst into an extremely complicated, sometimes dangerous profession, but since you asked: No, 32 is not too old. Charlotte Rose, a famous sex worker who is featured in the ITV report I linked to above, is 39 years old.
From: My Other Side. (April 13, 2020).
Dear How to Do It,
I have a wonderful new boyfriend, and we have been having great sex. The problem is that he does not smell good down there! I wasn’t so aware of the issue until our first night with some unprotected sex, and I immediately got a yeast infection. I started paying more attention and realized that he has some fundamental hygiene issue.
He’s uncut. I’ve been trying to take nice showers before with him, but the issue seems to be that he simply does not push his foreskin back to clean. Hence this terrible smell and yeast infection environment. I tried gently doing it in the shower and it clearly made him uncomfortable. So now we’re using lots of condoms. He has no issues during sex whatsoever, and then his foreskin is completely back. But I obviously don’t want to go down on him. He only likes hand action with the foreskin way up and not moving it at all down. It’s strange. I don’t know how to handle this. Obviously he’s a grown man, so I don’t want to lecture him on basic hygiene most that uncut men learn as a child. But something needs to change. What can I do?
From your description, I wonder if he’s experiencing a mild form of phimosis, or a related issue. That’s the name of the condition in which the foreskin is too tight to be comfortably pulled back and expose the glans of the penis. While people with phimosis are often incapable of moving the foreskin back from the head, “Score 1” phimosis refers to a retractable foreskin that is tight behind the head. Could it be that while technically his foreskin can roll back, it’s generally uncomfortable for him to do so, hence his masturbation technique and cleaning avoidance? I obviously can’t be sure from over here, but if that’s the case, well, he’s not just some smegma-collecting slob.
Either way, what he’s got going on down there isn’t compatible with your flora, and he should be doing whatever he can to preserve the integrity of your microbiome. This may require treatment, or it might require him to take soap to dick head. Requesting this doesn’t have to come in the form of a lecture—just ask questions, try to get some clarity, and then together figure out a way forward. He’s too old to be funky in the crotch, and your compassionate assistance may be what he needs to get himself right, annoying as that extra work might be for you. That’s partnership for you.
From: It Appears My New Boyfriend Never Got a Crucial Lesson About His Penis. (July 23, 2021).
More Sex Advice From Slate
Last year, my husband of two years—together six—and I were out to drinks with his childhood friend and the friend’s fiancée. (We’re both straight couples.) When we were several in, we were talking about losing our virginities, and his friend’s fiancée made a comment along the lines of “well, you know what they used to do.” I did not know what they used to do!