How to Do It

I Found a Woman With an Incredible Sexual Talent—but I’m Worried About What I’m Really Doing to Her

A Black man holds a Black woman to his chest. There is a neon eggplant emoji behind them.
Photo illustration by Slate. Photo by LightFieldStudios/iStock/Getty Images Plus.

How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!

Dear How to Do It,

I’m a man in my 40s and have been fortunate to have had lots of great, amazing sex over my lifetime. I’m kinky and enjoy a wide variety of sexual activities, but at base I’m very dominant sexually and my favorite kink has always been ass play, both giving and receiving. I’ve recently started seeing a woman who is the same age and was relatively inexperienced with ass play prior to me. To our delight, she has really taken to it and enjoys it very much. She is the only woman I’ve ever been with who has multiple orgasms from strictly penis-in-anus sex.

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So far, so great! We’ve discovered we are very sexually compatible and have really great sex in other ways as well. But here is the issue: When I penetrate her anally, she likes it very rough. While we always use plenty of lube, she likes it best when I do not really “warm up” her ass. I am well-endowed in both length and girth, and she is petite. And at her specific request, it is intentionally brutal. Our typical anal sex session involves me railing her mercilessly until I get off. These sessions can sometimes last a good while, at least where strictly penetrative anal sex is concerned (10 or 20 minutes). During these encounters, she is clearly in some level of moderate to intense pain nearly the entire time, but she always orgasms, usually multiple times. She never taps out (we have a safe word). I frankly have never encountered anyone like her in that department. I don’t know how she takes it like that. She doesn’t visibly bleed or experience any obvious adverse post-sex after effects other than some soreness/tenderness the next day. We have great communication and have discussed it openly. And hey, I’m not complaining. It turns me on immensely. And she consistently declines more slow and gentle anal sex when I have suggested that option.

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But what are the physical ramifications for her anus and rectum long term? We have had this type of anal sex several times a week going on several months now. She said she sees no adverse effects and has experienced no changes in bowel or bladder habits. But I’m concerned that anal sex of this duration, intensity, and frequency can have adverse long-term physical effects, such as loss of anal sphincter tone, which could lead to bowel issues for her later in life. She says she’s not concerned about it, but I’ve read about gay men who have been anal sex recipients over many years, as well as people who have regularly engaged in large anal penetrations, who experience incontinence, anal fissures, hemorrhoids, and other colorectal problems associated with these types of activities. While I enjoy it very much, I definitely don’t want to cause her health issues later in life from this. Are there exercises like Kegels that she can do to keep sphincter tone? I would be fine with less frequency, duration, or intensity with her if it would save her from having issues later, even despite her lack of concern about it. Your insights would be appreciated.

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­—Butt Trouble

Dear BT,

In my own poking around (heh), I noticed that there isn’t a ton of data on the long-term effects of receptive anal sex. I confirmed this with Dr. J. Michael Berry-Lawhorn, a clinical professor of medicine at the University of California–San Francisco’s Anal Neoplasia Clinic, Research, and Education Center. For nearly 30 years, Berry-Lawhorn has been seeing patients at risk for anal cancer, many of whom are gay men (but he noted he’s treated women). “I’ve talked to a lot of people about their sexual habits, what they do, their issues, and their problems,” he explained over the phone. He told me that it’s rare that he hears a patient complain about problems like you describe deriving from anal sex, even in extreme examples.

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“I have a fair number of guys in my practice who tell me they fist,” he said. “They’re not coming in saying, ‘I’m leaking all over the place. I can’t hold my poop. I’m staining my pants.’ Maybe they do, but they don’t talk about it.”

This last bit is important—just because they aren’t talking about it doesn’t mean it’s not happening. The little data that does exist suggests that there’s a higher rate of fecal incontinence among those who practice anal receptive sex. Berry-Lawhorn pointed to this 2016 study, which found, through self-reporting, that “fecal incontinence rates were higher among women and men reporting anal intercourse compared with those not reporting anal intercourse.”

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In 1999’s The Ins and Outs of Gay Sex, Dr. Stephen E. Goldstone wrote about the suspected mechanism that leads to such incontinence: “Insertion of a penis … causes your muscle to contract involuntarily. Repeated insertion through a contracted internal sphincter muscle may cause cumulative damage so that the muscle loses its ability to seal the anorectal canal tightly.” So learning and practicing anal relaxation is probably a good idea for long-term health.

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Berry-Lawhorn also told me that “there is some literature that shows women who have a history of anal intercourse are more likely to have anal precancerous lesions.” He recommends your partner get screened for anal disease, specifically HPV, by someone who specializes in managing anal dysplasia. He also recommends Kegels and the general promotion of good bowel function (like eating plenty of fiber).

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On the up side, the doctor, as much of an ass expert as you’re likely to encounter in the world, did not seem at all disturbed by the practices described in your letter. He said he was impressed by your concern for your partner’s health, and he put things into rather lovely perspective that I’m sharing and co-signing: “It’s true, women and men who practice anal intercourse have higher rates of fecal incontinence. On the other hand, life is complex. There are many things people do that are not the best for their health but they continue to do them because they get a certain amount of pleasure from them. I think it’s about risks and benefits. From the description, this woman seems very happy having this sex and doesn’t want it in any other kind of way. I don’t think there should be any judgments about that. I think as long as she’s happy and it’s mutually consented and agreeable, they should continue to do what they’re doing.”

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Dear How to Do It,

I am a man in his mid-20s who is currently dating a man in the same age range. I like him so much and things are going great so far, but this is his first relationship. He had never even kissed or made out with anyone before me. He really doesn’t know much about his likes and dislikes with regards to sex and making out. Meanwhile, it’s been a few years since my last sexual relationship, but I had a lot of wild (and fun!) experiences in college, so I basically know what I’m into and not into. I know he’s open to learning, because it’s only been a few weeks and he’s a great kisser now, but we haven’t done a whole lot on the sex side. I’ve pretty much only dated or had sex with people with more sexual experience than I, which was pretty great, but now I’m the one with more experience and I don’t know where to start! How do I teach him how to get me off, and how do I help him find out what he likes?

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—Willing Teacher

Dear Teacher,

I’m unclear on just how much you’ve communicated with this guy about his interests, so forgive my obviousness, but: Why don’t you ask him? Dan Savage has repeatedly made the point that so many satisfying gay encounters begin with an orienting question: What are you into? Employing such directness can be intimidating, but here it is not just worth it, it’s extremely important.

If you’ve had this discussion and he doesn’t know, ask him if there’s anything he’d like to try or has been generally curious about. You can look at his lack of clarity as a challenge, or you can view it as an opportunity for exploration. I urge the latter. Ask him if he wants you to take the lead. Put yourself in his shoes: What made you comfortable when the roles were reversed and you were the less-experienced party?

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That said, in the end, it’s really your partner’s job to understand his own sexuality, even if that means effectively tossing you the keys and asking you to do the driving. Are you comfortable with being in control, if in fact that’s what he wants? You certainly aren’t obligated to be. Some people feel naturally more or less submissive and aren’t much interested in switching to the other side. In that case, you may have found yourself in a mismatch, but that won’t truly be clear until you both can effectively communicate what it is you’re looking for. If nothing else, you seem to understand what gets you off, so ask him if he’d be up for doing that. If he says yes, let the instructions begin.

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Dear How to Do It,

I’m a 67-year-old man. I have had maybe four sexual partners in my life, including a 23-year marriage. None of the four women liked or wanted to experiment, so the only sex I’ve had was plain vanilla sex. I feel like I never really learned how to have good sex. I’m also pretty small, and have what I think the urologist called venal leakage, so I have a difficult time maintaining an erection. Because I’m built small, if I use a cock ring, there’s not much left in terms of length to penetrate that deep.

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So, I have not had sex in like four years. I’m really scared about my next relationship because I don’t have a lot of experience in various positions and am scared of looking like a teenage boy having sex for the first time. I also don’t know how to communicate that I have problems keeping an erection. Please help me figure out how to deal with this. I don’t know who else to talk to. There’s only about three certified sex therapists in my area and none of them take insurance, so I can’t afford their fees.

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—Running Scared

Dear Scared,

You might want to circle back with your urologist—if you don’t have your condition’s name right (it’s most commonly referred to as “venous leakage”), I have a sneaking suspicion that you haven’t done much to treat it. The PDE5 inhibitors typically prescribed to treat ED can yield poor results when the cause is venous leakage, and so you may want to pursue vascular reconstructive surgery (explained briefly here) or even a penile prosthesis (much, much, more about that in a past column). But you might want to try an ED med first, in case yours can be managed with one.

While specialized therapy can be pricey, see if you can find a more general therapist to at least manage your anxiety. What you are afraid of does not actually exist—in your feared scenario, you’re little more than a concept (a 67-year-old man who’s bad at having sex) coming up against the concept of a more experienced, demanding partner. In actuality, when you do find yourself in the vicinity of a potential sex partner, you’ll be a person in front of another person. She’ll evaluate you accordingly, and she may already have feelings for you if you’ve gotten to the point where sex is on the table. With feelings come compassion. There is plenty of stuff to do in bed that doesn’t involve a hard dick, and there are plenty of ways for you to attempt to get your dick in working order. It doesn’t really seem like sports sex will be a prospective hobby or that you’ll be frequenting orgies, but if you take your time and build understanding with a partner, you may find that which you fear eluding you: acceptance.

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Also! Plain vanilla sex can be good sex. It may not be the sex you’re after, but it is not inherently worse than other more specialized, kinkier varieties. If there is something more specific that you’re interested in, by all means, pursue it, but don’t turn your nose up at something just because it’s ostensibly conventional. Sometimes even basic friction can feel like magic.

Dear How to Do It,

I’ve been in a relationship with my boyfriend for three and a half years. He is six years my senior. We share children from both of our past relationships, and this year, we welcomed our first child together. At the beginning of our relationship, our sex life was great, no complaints. Now, we regularly engage in sex, although I would say I’m more active than he is. For the past year, he doesn’t seem to last. From the time we start intercourse, he only lasts about three minutes. Which can be very frustrating to me. I have talked to him about this a number of times, and we have tried solutions like more foreplay to make sure I’m satisfied too. Unfortunately, I don’t usually “finish” and have to take out my frustration with a vibrator when he goes to work the next day. His excuses are that “he just can’t last,” or “I’m too hot”—but honestly, it just feels like he is being lazy. I am at the point where I no longer desire to have sex with him because I think I’ll just be dissatisfied. Do you have any advice on what I can do?

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—Too Hot

Dear Hot,

Not to give anyone a pass for potentially lacking consideration, but reading Ian Kerner’s recent So Tell Me About the Last Time You Had Sex: Laying Bare and Learning to Repair Our Love Lives gave me a whole new perspective on premature ejaculation (or early ejaculation, as he often refers to it). I recommend picking it up. Kerner’s own experience with the issue led him to write a manual on cunnilingus, 2004’s She Comes First, and so it makes sense that his account is particularly sensitive and thorough. Now, keep in mind that three minutes exceeds the generally agreed-on parameters for what constitutes premature ejaculation (which Kerner says is ejaculating any time before two minutes, but I’ve seen it defined as one minute and under). But for your purposes, let’s consider your boyfriend’s ejaculatory latency time as dissatisfying to you, thus early. Firstly, the stereotype of a willful minute man who rudely comes as soon as he gets the hankering is somewhat overblown—there’s some evidence that premature ejaculation is hereditary. There’s growing evidence that it runs in families. On top of that, it may be related to neurotransmitters—Kerner reports that studies show that low serotonin levels have been observed in people with PE and that because of this, a low dose of an SSRI may help.

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Kerner offers a multipronged plan to help treat ED, which can include a numbing spray, pelvic-floor exercises, and the employment of various techniques during sex like the stop-and-start technique (which is exactly how it sounds—he stops when he’s close, waits, and then continues) and the squeeze technique (a thumb is placed on one side of the penis, middle and index on the other, and squeezing is performed upon nearing climax). These techniques require practice with the end goal of retraining one’s ejaculatory tendencies. Kerner also details forms of outercourse—the stimulation of the vulva/clitoris with the penis without vaginal insertion—and oral sex, which could get you closer to orgasm so that you could potentially have it when finally intercourse takes place, late in the sex script.

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All of this, by the way, requires work on your boyfriend’s part (as well as your own, as well as patience). His ejaculatory latency time may not be his fault—it may feel to him innate—but there is plenty he can to do attempt to manage it, and if he’s not, well, maybe “lazy” isn’t such a bad characterization after all. I do have to wonder why you wait until the next day to take out your vibrator and finish yourself off. If that’s a tried-and-true way of facilitating your orgasm, why not incorporate it into your sex with him? It’s probably wise to expand your view of proper sex beyond intercourse that ends with both of you orgasming at exactly the same time. It’s nice when it happens, but it’s not many people’s reality. Letting go of these ideals will allow you to approach this issue practically.

More How to Do It

From 2018 to the beginning of the pandemic, I had semi-regular (maybe twice a month) sex with a friend and coworker, “Mark,” who is married. His wife also works in the same hospital as we do. As soon as the pandemic happened, Mark and I stopped sleeping together. Now we’re all vaccinated and we have a bit of time off, and Mark suggested I join him and his wife to stay for a week in a cabin in the woods as they do every year. He’s told me before they pretty much just spend the whole weekend having sex. More shockingly, he told me it was actually his wife’s idea to invite me on the trip—except I don’t think she knows we used to hook up.

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