How to Do It

I Think My Husband Masturbates With His Best Friend

How do I, um, bring this up?

Partial view of the faces of two men with eyes behind them in neon lights.
Photo illustration by Slate. Photos by Albert Dera/Unsplash and Taras Chernus/Unsplash.

How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to

Dear How to Do It,

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! It turns out they masturbated together as teenagers, which included “giving each other a hand.” I was taken aback by this, but they all seemed to think it was hilarious, and my husband was embarrassed, so I shrugged it off. Teenagers do things. We didn’t talk about it again.

Recently, I was out with the fiancée for her bachelorette party. My husband was at the bachelor party the same night. Someone joked about them getting too friendly with strippers, and the fiancée said they were more likely to get too friendly with each other. She then started telling the group that she knew my husband, her fiancée, and at least one other guy from their friend group masturbated together into college and their 20s (we’re all around 30). She said she suspected they still do it now sometimes, but she doesn’t care because it’s “just jerking off.” I’m now kind of paranoid about this! I did some Googling that suggested this is a fetish for some guys who are with women. Um, is it? Is there a way I can bring this up with my husband without accusing him of cheating? If he’s hiding a major part of his sexuality, I kind of worry about what else he could be hiding.

— Five-Knuckle Shuffle

Dear Five-Knuckle Shuffle,

It does seem like more straight-identified guys are getting into mutual masturbation with other so-called straight guys these days. Or maybe connectivity has made this phenomenon more accessible and easier to gauge and discuss? Ya never know with these things. A recent GQ trend piece explored the phenomenon of “straight” masturbation clubs, and I’ve seen online ads for such clubs that specifically target “straight” guys and more or less rebuke gay ones. I put “straight” in quotes because, sitting around, dicks out, perhaps polishing a penis that does not belong to you, sounds pretty far left of strictly hetero to me, but it’s also increasingly clear that there’s infinite space in the gray area between a Kinsey 0 and a 6. It is therefore conceivable that there are guys out there who mostly have sex with women but enjoy the male bonding that comes with sitting around and busting some nuts with other men. As you may have noticed, spending time with naked men is fun.

So, perhaps this is not a major part of your husband’s sexuality but a minor one. The way I’m personally inclined to think about this goes something like: He could be sitting around with his buddies playing poker and holding cigars, or they could be sitting around watching porn and holding their dicks. It’s all time-passing leisure. If he’s not depleting himself of a sex drive from whacking it too much, or having his dick stripped raw by his buddies’ calloused workout hands, what’s the difference? You, naturally, are under no obligation to take such a laid-back stance. (After all, he’s your husband.) I think before you determine a method of bringing this up without accusing your husband of cheating, you should figure out if you consider this to be cheating. Many would! If you’re in a monogamous arrangement, it’s perfectly reasonable to expect your husband to keep his hands on his own controller and not be playing another guy’s joystick. You can bring this up quite easily by referencing the previous conversation on this topic that you were both present for. Request more detail and clarity. He might be embarrassed, but he owes you the full story. For maximum extraction potential, work from love and compassion, not shame.

The fiancée of your husband’s potential jerk buddy, though, is a real piece of work, isn’t she? She’s probably making things more difficult by being so loose-lipped about your husband’s potential predilection, something you have every right to feel sensitive about and not want blabbed. I think you’re in the right to tell her to cram it, if you’re so inclined. You needn’t be delicate with her.

Dear How to Do It,

I’m a woman in my early 30s, three years out of a decadelong relationship that featured traditional, infrequent, and very unsatisfying sex. Now that I’m getting reacquainted with my sexuality, I’m making up for lost time and discovering that I’m much kinkier than I realized! I’ve been having lots of fun saying “yes” to any sexual scenario that piques my interest—bondage, a threesome, polyamorous partners—and am hungry for more. My question is: How do I find them?

I don’t give off kinky vibes. I’m a mother, dress traditionally femme, and strike people as a “girl next door”—a persona I love subverting behind closed doors. I live in a somewhat conservative, rural university town and work in a community-facing field that requires I be discreet, so I don’t feel like I can go freely cruising on apps. The bar scene here caters to the student crowd; my friends are mostly colleagues. Being safe (physically and sexually) is important to me, and I’m more interested in finding partners for regular play than an anonymous one-night stand. I’m not near any big cities, and we don’t have anything like a swingers’ club (at least that Google has been able to reveal), but I’m sure others like me are out there. How do I subtly advertise myself as a kindred spirit?

—Seeking the Secret Handshake

Dear Seeking the Secret Handshake, 

Uh, it seems like you’re doing fine? Bondage, a threesome, and polyamorous partners in the past three years? That’s more excitement than a lot of people experience in a lifetime. Given your hawkish approach to discretion, moving at a slower pace and taking the kink as it trickles in might just be what you have to do. But I suppose there are ways to maximize your sex having. You can talk to the kinky/poly partners you’ve had about where to find more and/or congregate. You may not feel comfortable freely cruising on apps, but you could certainly at least create online profiles without any identifying features (such as a picture of your face) and see what kind of catch that yields. There are poly groups all over the country—surely one is within at least occasionally attainable distance from you. You may also want to go poking around whatever major metropolitan area is nearest you for other fun. This isn’t ideal, but you have a lot of constraints here (I’m talking about the figurative ones in this case). Given that you seem intent on protecting your public identity from being soiled by the fact that you are a human with sexual desires, it may be useful to essentially relocate your sex life while keeping your working/nonsexual social life where it is.

You could also consider coming out to some degree (or at least, not being so intent on remaining closeted). A lot of the time, the idea of other people knowing about our private sexuality is a lot scarier than the reality, and it’s much easier to go after the pleasure you’re interested in without the obstruction of hypothetical outside judgment. This is by no means true for everyone everywhere, though, so certainly weigh the risks and rewards with careful thought.

Dear How to Do It,

I’m a cis gay guy in my mid-20s. I’ve been sexually active since high school but had never had anal sex—topping or bottoming—until a few months ago, when years of psychotherapy finally kicked in. I realized I wanted to bottom, worked through a lot of fear and stigma, read up on the mechanics of butts, and have been having a great time.

Over the course of my newly energized hookups, I’ve grown curious about topping. My problem is that I am terrible at it. I can’t seem to stay hard enough to get it in, and the one time I did I almost immediately went soft. I’ve tried with three or four guys, all of them attractive to me and patient. I used to think the problem was my inexperience wearing a condom, but a recent bareback attempt confirmed that this was not the case.

I wonder if topping may just be physiologically challenging for me, but I suspect there’s a significant psychological component: I don’t have hardness issues during other kinds of sex; I still have some residual anxiety around anal sex (pain, mess, safety, the usual); and I know that I’m only at my very, very hardest when my partner is engaging with some of my more out-there kinks and fetishes.

I’d genuinely like to be able to do this if I can. (There’s no rush, fortunately. I’m just eager and exploring.) Should I keep doing what I’m doing—sticking with my therapy, hoping I’ll find the right bottom for me, expecting some more abortive topping attempts along the way? Or is there anything else I could sanely do to speed this along: cock rings, mental exercises, Viagra, elephant-tusk potions?

—Top Down

Dear Top Down,

Yep, cock rings and E.D. meds sound right. Try them out in that order. (I’ve never had much luck with pelvic-floor strengthening myself, but I know that some guys swear by it.) If you’re an ardent masturbator/porn user, try laying off for a few days to see if that gets you horny for some butt.

It sounds like you’re mostly just anxious—I wonder if the times when you’ve tried to top, you’ve essentially put yourself on the spot and then found yourself too shook to finish the job. Fear can be a major boner killer. You could probably do with a more relaxed scenario, perhaps with a vers guy who is as happy topping as he is bottoming. This way, all the pressure isn’t on your maintained erection to render the sex act successful. You might even be a good candidate for flipping—maybe you need to get fully turned on via bottoming before you can top. You might also just need the kink element there.

It could be that physiology has rendered you a natural bottom, but I think you have some more exploring and experimenting to do. Topping can feel very overwhelming, which is why it’s important to do so with a partner you are comfortable with. The right elements in place will help it along. Sometimes it takes that one successful ball in the goal, so to speak, to prove to yourself that you are the stud you suspect you might be, and topping just gets exponentially easier from there. But if it doesn’t work out, don’t beat yourself up: There’s no shame in being a full-time bottom, and you’ve been having a great time doing that anyway. When all else fails, make like Jerri Blank and go with whatcha know.

Dear How to Do It,

In high school, my then-boyfriend wanted to perform a particular sex act on me. He asked at least three times separately, and each time I said no, and he didn’t carry it further. I really, really did not want him to do what he was asking to do. I had even written out a little speech I was going to read to him saying it would never be in the cards. Then he asked when I was high (before I’d worked up the courage to read him the speech), and I said yes. I ended up liking it, and we did it many times with my consent. But I know I wouldn’t have said yes the first time if I hadn’t been high. Maybe I’m blowing this out of proportion, but since I said no several times, I feel like he shouldn’t have asked while I was impaired. It is now two years later, and I have never felt traumatized by this. Was that a violation? What do I call what happened? Should I reach out to him about this and let him know? We ended on pretty bad terms, but if this was a violation, then I would be willing to send him a message so that he doesn’t make the same mistake with anyone else.

—Worried, Not Traumatized

Dear WNT,

I’m always going to come down on the side of communication, especially when that communication might be therapeutic to at least one involved party and/or could make the lives of uninvolved parties easier in the future. So, yes, I would say you should reach out to him, if only because you’re still thinking about this two years later, regardless of how it should be labeled. The guy sounds like he has the potential to be an ass, though, so be forewarned that he may not be the most receptive audience.

As to whether it was a violation, the details here are too nebulous for me to say for sure. Like many instances, this seems to exist in the gray area between unabashed consent and rape. It’s definitely shitty behavior to keep asking for something you’ve already been denied—it’s at least pressuring, possibly coercive, and wholly annoying. From a legal standpoint, whether your inebriation obstructed your ability to give consent would depend on what state this happened in. And then there’s a matter of what state you were in: Were you unable to reason as a result of your high? Are we talking weed or another drug?

I’m mostly asking questions in my answer because I think you have more thinking to do. That you take care to stipulate that you enjoyed this sex act “many times,” went on to consent to it, and maintain that you haven’t felt traumatized by it is preventing me from coming down too hard on determining what this was exactly for you. Not everything that we look back on negatively or with a sense of regret needs to be understood as a cataclysm, but issues regarding consent are particularly sensitive, and I don’t want to absolve coercive behavior on the part of this guy just because it didn’t ruin your life.

Could “harassment” do the trick for your labeling and organizing needs? It might apply. It strikes me that a particularly frustrating feature of this situation could be its very haziness—this is something that perhaps doesn’t demand a shorthand way of referencing it, something that in fact you may never know what to “call” it and will require at least a few sentences when referring to it. Life is complicated like that sometimes.

If you do end up talking to this guy, prepare to have a long, carefully articulated conversation about what this meant and didn’t mean to you, perhaps one that even accounts for your feelings of confusion. Unfortunately, one thing this guy burdened you with is a lot of explaining to do regarding what he did to you.


More Advice From Dear Prudence

I am a freelance web developer who nearly went bankrupt. A few years ago a client referred me to a friend who needed some search engine optimization. The friend operates an adult website. Adult websites make a lot of money but have trouble finding honest, competent help. One job turned into another, and working with adult websites has become a thriving business for me. My problem is that nobody knows I do this. My wife thinks that I design websites for local companies. I don’t work with sites that do anything illegal; my clients are high-end, soft-core sites. I’m getting to a point where I can’t hide this anymore. I’m going to get a prestigious industry award, which means that an Internet search of my name will reveal the nature of my business. I’ve wanted to walk away for a while, but the money has gotten us a lifestyle that we struggled to have for years. I feel like I’m stuck between disappointing my family by turning off the money pump or having them find out that I work in the adult industry. What do I do?