How to Do It

My Guy Can’t Have Sex Until He Gets Circumcised

What’s taking him so long?

A man lies in bed. Behind him are neon scissors.
Animation by Lisa Larson-Walker. Photo by monkeybusinessimages/iStock/Getty Images Plus.

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

Dear How to Do It,

I’ve been dating a great guy for about five months that I’m totally falling in love with. I find him immensely attractive and have been hot in the pants since day one. He sends me signals and to a lesser extent tells me he feels the same way toward me sexually, and I’m confident we’re on the same page emotionally. The issue is we haven’t had penetrative sex, and the reason why is he finds it very painful. The solution to that is a circumcision. He told me this pretty early in our relationship, and he said he has plans to have the surgery scheduled in the imminent future … but he still hasn’t. And there seems to be zero rush! I am dying over here. We’ve had very limited oral sex and we often kiss/feel each other up and get to a point where sex can happen, but it doesn’t. He’s told me before he can have penetrative sex if he drinks, but I don’t want boozy dick, and I don’t want him to be in pain. I want him to get snipped!

We’ve discussed his hesitations regarding surgery and other alternatives, and I’ve suggested he consult with his doctor further, etc. I am beginning to feel that neither the surgery nor an actual full (meaning penetrative) sexual component to our relationship is meaningful to him. I find the lack of a full-on sex life being fine with him hard to believe, given his stories of his slutty past, but perhaps he’s just putting on a show. (Full disclosure: In my previous relationship of a year, my partner had significant emotional issues that severely stunted our sexual relationship in a timeline eerily similar to this one. We didn’t have sex the first six months of our relationship and then rarely and sparingly satisfyingly after that. I haven’t had both emotionally and physically satisfying sex in years.)

I don’t want to be pushy, but I don’t know how else to express I need sex without making him feel like I’m forcing him into surgery or making him feel less than. It’s been an ongoing conversation, which I was fine with, but I’m getting antsy. Please help!

—Wound Up

Dear Wound Up,

If penetrative sex were a priority for this guy, he would have gotten cut long before he got you. It sounds like he has some kind of sexual block—it could be anything from trauma to fear to a sort of ineffable lack of interest—and he’s using his foreskin as an extremely tight security blanket that he’s got pulled up past his neck and around his head. “The old phimosis excuse,” no one called it ever.

It could just be that the prospect of this surgery and what comes after is scary and daunting for him, but it doesn’t seem coincidental that you aren’t having much oral sex either. I suspect there’s something more going on with this guy, and maybe the reason you don’t know what it is has something to do with your having met him only five months ago. Maybe he’s not comfortable enough talking about it yet, or still figuring it out himself. Regardless, he should be more forthcoming, and you should be less trusting, since you’ve been in an “eerily similar” bind before. I know, I know. You’re falling in love and you couldn’t have looked before you leapt if you even tried, but from my perspective, you’re signing up for more sexual frustration given how sexless the honeymoon period of your relationship has been thus far. I don’t really think you have accrued enough time with him to reasonably demand this dude that you just met get an operation that changes the face (or head, I guess) of his genitalia unalterably, so control what you do have a right to: where you put your love and how generous you want to be with your patience. We’re so lucky to find love, but a mechanically functioning relationship is an entirely different matter, and from what you’ve described, what you have with this guy is already on the fritz.

Dear How to Do It,

I’m happily married. Two years. Dated two years before that. The second year of dating and the first year of marriage were long distance (read: military). I love my husband. I love our life together. And I love our relationship. I just don’t love the sex. We do it about once a week. It ranges from “just close your eyes and it’ll be over soon” (when it’s about him) and “good” (when it’s about me), but never great.

I kind of anticipated that this might be a problem early in the relationship. He’s not my type, physically. I was not initially attracted to him. But with a lot of work on his part, he was able to turn me on. And I love the person that he is. So I chose him. And we made our sex life work. But it turns out long distance was helping. The inability to have sex most of the time was a turn-on for me. So when we were together, I wanted it. Now that we live together and I can have sex with him whenever I want, I don’t want it. Part of it is that I’m still not all that sexually attracted to him. He’s slightly overweight and it doesn’t seem to bother him at all. I work out religiously and try to look good for him and myself. You could call me shallow, but abs are great for stimulation in some of my favorite positions. I miss those positions.

I’ve tried talking to him about the weight thing, that it would help me in bed and that I want him to be healthy and take care of himself, but he doesn’t seem to care enough to do anything about it. After living together for a year, my sex drive is almost completely gone. Which is fine when we’re together. I accept that this is my new normal. But when I go on work trips, my emotions are harder to control. I find myself noticing other guys, being attracted to other guys, thinking about other guys, struggling to restrain myself from talking to other guys … I don’t want to cheat on my husband. But I also wonder if this is sustainable. Can people have a long and happy marriage without satisfying sex?

—Needs Washboard

Dear Needs Washboard,

The answer to your question is clear: You will not be able to have a long and happy marriage without satisfying sex. You need it, and you’re going to have to figure something out, and yes, I think the responsibility falls on you because you got yourself into this situation and your husband seems content all around.

How to go about doing this is another matter. It’s hard to untangle all of your issues. I find it disconcerting that your slightly overweight husband is so unattractive to you. Why in the world would you get with a spare-tire-having dude if you had such a strong predilection for hard bodies? Haven’t you heard that for the vast majority of the population, it’s all downhill after your wedding day? People let themselves go out of comfort with their partner and because metabolism slows over time. (This is gonna get more and more difficult for you too. You’re likely to be eating birdseed and never not in a plank position by the time you’re 80.) Expecting physical perfection from your spouse is a recipe for disappointment.  You admit a degree of accountability in your letter, but I just want to reiterate—to quote my lord and savior Judge Judy—that you picked him! You set this problem up for yourself, and now you’re living in discomfort. Go figure.

What was it that won you over to the realm of doughy in the first place? And can that be brought back? If it’s a matter of proximity making the heart go yonder, you could put physical space between the two of you temporarily (Esther Perel might go as far as to recommend living separately for a while, and her Mating in Captivity is a good guide for reigniting the spark domesticity and familiarity can snuff out). You may need to contrive a situation that allows you to miss him a little.

I find your note frustrating for reasons I touched on above, but the part in which you wrote that the sex “ranges from ‘just close your eyes and it’ll be over soon’ (when it’s about him) and ‘good’ (when it’s about me)” has me flabbergasted. How is the sex not about both of you at all times? What exactly are you doing? Are you talking about receiving oral sex here (while the other party suffers through giving it)? Is there some kind of positioning that is excruciatingly uncomfortable for one party and astronomically pleasurable for the other? Are you that mismatched? Maybe try rethinking your approach and finding stuff that would allow you to be on the same page. At the very least, it would be a start.

Dear How to Do It,

A great guy just ended our friendship because I didn’t want to be intimate physically. I was open to it at first, but the thing is: He was a HORRIBLE kisser. Really truly awful. Imagine very tensed lips completely surrounding yours, constant pressure, no variation. We talked a bit about what I’d prefer (including some demonstrating), and it got a little better, but I found myself dreading it and certainly not wanting to go further.

It was uncomfortable—for both of us—trying to coach a grown man (we’re in our 50s), and I’m sure I didn’t do a great job of it. People can be really fragile in this department, and I probably didn’t say enough for fear of wounding his pride. Any advice for if this happens again?

—Read His Lips

Dear Read His Lips,

In a perfect world, moving forward, you could use a guy’s kiss as a litmus test for compatibility. If you were to encounter another really truly awful one—here defined as “I deeply dislike how he kissed”—you would then know where never to put your mouth again. You can’t remain kissing friends with everyone whose lips yours meet, and by definition not every man is the one. I’d say your minor folly here was spending so much time trying to teach a guy who was unteachable. That shouldn’t be your burden.

I realize, though, that perhaps there is a limited reservoir of available men that you are attracted to and that maybe circumstance calls for a lighter filter. I wouldn’t advise anything too drastically different from what you already did in your impromptu Kissing 101 with this guy aside from more patience and reassurance, which you essentially admit you didn’t provide enough of. I’d stop short of out-and-out charity, though. This is a situation where it’s perfectly reasonable to be giving to get something, and if he doesn’t stick around, you just trained a guy for his next lover. Invest your time wisely.

Dear How to Do It,

I had anal sex with my boyfriend some time ago. The first time it really hurt and the second time was really great. But I haven’t done it since because I am still scared. He brought it up recently and I’d like to try it again. He’s very sweet and considerate. We have great sexual communication. And I’m excited to try it again. But the anxiety is real. I’m hitting you up for relaxation tips and things I can do on my own to prepare for this special occasion. Any advice?

—Back to Back

Dear Back to Back,

Welcome to the land of butt. It’s nice, if a little bit finicky here. The best advice I ever received about bottoming was a paradox: You have to concentrate on relaxing. It doesn’t quite make sense, like when you’re stretching in an exercise/yoga class and the instructor tells you to breathe into your legs and you’re like, “My legs don’t have nostrils????” But you do it anyway because you’re there, and what else are you going to do, and it ends up actually working, or at least you think it does? I’m not trying to get all Tony Robbins on you here, but there is probably something to the expression “where focus goes, energy flows”—I truly believe that by mentally engaging with your butthole, you’ll be a lot more able to experience physical pleasure there. All of this is adjacent to meditating, this sort of willing your body and mind to go (and not go) certain places on a sensory level. This is one of those situations where as long as you believe strongly enough that you got this, you got this.

I feel weird about recommending poppers, because they’re so under-researched and who knows their possible ill effects while they make your nerves feel pyrotechnical for about a minute. But look, poppers do help you relax. I once had a gay urologist recommend poppers with an enthusiasm reminiscent of how my dermatologist used to evangelize Cetaphil, so don’t take my word for it; take the word of that doctor that I visited a few times and haven’t seen in years.

Lube is your friend (I hope you’re by now well acquainted). And since it’s your butt that’s being entered, call the shots. If initial penetration is accompanied by that searing pain that makes a dick feel like a red-hot poker, make him take it out until the pain subsides. Then, carefully, have him try again (it’s always easier upon reentry). Take advantage of his sweetness and consideration; your butt’s on the line here, and more literally than in most other situations.

—Rich