How to Do It

I’m Having Great Sex Again in My 40s. But the Penises Are … Different Now.

Please help me.

A woman confused by an eggplant emoji.
Photo illustration by Slate. Photos by 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 44-year-old woman who is having a lot of sex with men again after ending a 14-year monogamous marriage. I’ve always had a sky-high sex drive and consider myself very sex positive. I had tons of wonderful sex in my 20s, and it is even better in my 40s on many levels. But I’m having an issue that I’ve started to perceive as recurring and it’s messing with my head: For whatever reason, the men I was with in my 20s were all uncircumcised. I know this is at odds with the average, but I’ve done the math, and about 90 percent of men I’ve been with were uncut and the handful of circumcised guys were not great matches. My ex-husband, with whom I’ve had the most lifetime sex, was intact. I know my way around foreskin and the oh-so-sensitive parts of uncircumcised dick. And I LOVE it. There are no words to convey how much I love the look, feel, smell, reaction to touch, and growth trajectory of uncut dick.

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I’ve always taken a strengths-based approach to life. I loved giving oral and I was good at it. I loved hand jobs and I was good at it. Chicken-egg. The “problem” is that all of the partners I’ve had as part of this new phase of my life so far are circumcised, and I’m starting to feel a bit inept! I am having trouble getting these men off in the same ways I could always map and understand the particular contours of each unique dick (and brain controlling it) in my 20s.

There could be a lot of things going on here that are not attributable to circumcision. But I’ve begun noticing that the men I’m having sex with now are much less sensitive to touch or flicks of the tongue or even when I swallow them. I’m having sex with men my age and older, so maybe some of this could be from normal aging and it takes older guys longer to come? I’m used to being in control and edging men up to mind-blowing orgasm (before I knew it was called edging). Now, I’m sometimes getting to the point where I’m frantically trying to achieve the “goal” of orgasm. This does not feel good!

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I’ve asked two of my trusted recurrent partners to show me how they make themselves come in the spirit of learning. It seems that they both use so much pressure and are rough with the head of their cocks and around the frenulum in a way that have a hard time imagining myself pulling off. I’ve done some Googling about cut vs. uncut dick, and all the resources I can find seem to be reassuring people that uncircumcised cock is OK and not gross and how one might handle it. Not helpful for me. I want to like circumcised dicks, and I want to develop skills with it that make me feel like the sexual rock star I’ve always been. Am I making too much of this? How do I get back to a feeling of sexual competence when I seem to not know what I’m doing? I’ve thought of announcing a preference for uncircumcised men in my profiles, but that isn’t what I want. I want to be as good at pleasuring circumcised men as they all have been with me.

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I don’t think that the men I’m with are reading me as having an issue. They all seem satisfied, but I’m used to a higher standard of pleasure. Reading back through this I also think I might need to let go of my idea of myself as a sexual performer and just lean enthusiastically into fumbling around like a teenager again. But how do I do that?

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—Cocksure

Dear Cocksure,

I absolutely love that you read back over your letter and came to a possibly helpful conclusion yourself. Bravo for that initiative and introspection. There’s a really beautiful—and heady—feeling of power in executing sexual contact in ways that give our partners pleasure and goosebumps, and that can definitely become part of our identity in the same way that success at anything can. I think it’s smart to give yourself permission to experiment a little again, because that’s how you’ll get back to where you want to be.

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The other factors you describe are likely in play too, but in my own anecdotal experience, yes, circumcised penises are less sensitive. Far less. On the other hand, they have zero foreskin tangling issues in condoms, and may have lower susceptibility to some sexually transmitted infections, so there are upsides as well. While an uncircumcised penis can sit in your mouth as you swirl your tongue around and explore everything, I find most circumcised penises require more aggressive stimulation and more lubricant.

Here’s how I do it. I always try flicking my tongue around the head, especially under the ridge of the glans and the wrinkly part on the bottom where the edges of the glans come to a point, to see if they respond well. If so, I’ll keep spending time there. If not, I’ll try one last thing—gently nibbling with my lips on the aforementioned wrinkly area—and then move on to more up-and-down motions. I’ve never found a lube I like the taste of, and while I’d prefer not to do so, I’m not afraid of vomiting on someone’s dick, so I go for the thick-spit inducing deep throat to generate enough slidey liquid to protect them from friction. Once they’re lubricated, it’s about finding the squeeze pressure they like and the up-and-down pace they prefer. You can also do a motion similar to tapping your fingers but with them wrapped in a fist around the shaft of their penis. Adding the mouth is usually appreciated, and I’ve found much success with sucking as I pull up.

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Another tactic that seems to help is spending extra time on the non-genital erogenous zones they’re comfortable having touched. The more worked up they are, they more sensitive they seem to be. Good luck.

“I’ve Noticed Something Strange About My Well-Endowed Lover …”

New on the How to Do It podcast: “I had a two-year, no-strings-attached hookup friendship with a really hung guy. Now we’re seeing each other again. And I’m pretty confused about something I noticed.”

Dear How to Do It, 

I have an aversion to one particular thing with sexual intimacy that I have never heard or read about. I cannot stand to have someone hold my face in their hands. I like having it stroked or kissed or licked. But I absolutely hate having it held like they do in movies—the guy leans in and then grabs the woman’s head and holds it in place for his kiss. I don’t know if that’s where guys got the idea but I think it is aggressive and it angers and repulses me. I can’t even stand seeing it on a screen. Not all men do it but I don’t know how to handle it when someone does.

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My problem is twofold—how to express my dislike and when to bring it up. I’ve tried “please don’t do that,” “I don’t like that,” “that makes me uncomfortable,” and similar things, but guys are always mystified because they don’t know what I’m referring to since they’re not doing anything they think is unusual. If I say “please don’t hold my face” they think I don’t want it to be touched or kissed. Any of these tends to kill the momentum and the guy takes off never to be heard from again. It seems to require a more in-depth discussion but I don’t know at what point in a relationship that should come up. It’s definitely before “how do you feel about anal?” but seems out of place before even knowing if there is going to be a goodnight kiss on a first date. Some guidance, please.

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—Hands Off

Dear HO,

I think you need a full paragraph. “I like to have my face kissed and touched, but I don’t like to have it held or cupped. It makes me feel _____, and that’s uncomfortable. But please, kiss my face and stroke it with your fingers gently.” You might then field follow-up questions, which are a great green flag. You also might field further face cupping, at which point you should extricate yourself and move on.

The timing is personal. I bring sexual specifics up early and casually, but I’ve had over 15 years as a sex worker and five as a sex advice columnist, so “How do you feel about anal?” feels like appropriate coffee conversation. You might—justifiably, understandably, and reasonably—feel more shy. Depending on how much face-holding disrupts the mood for you, you might wait until they start to do it and give them your feedback then. It’s entirely up to you.

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Dear How to Do It, 

My husband and I have been married for 27 years, and for the most part, have had a decent sex life—except for the last four years or so. Well, menopause is done and over with now. Recently, I find myself wanting sex more often, which is not a problem, but now I feel awkward initiating it because of the dry spell in the last four years. Also, I am having trouble just relaxing with it, like I forgot how. I really like having my drive back, but am obsessing about it disappearing again. Any suggestions?

—Once and Again

Dear Again,

Tell your husband how you feel! Presumably the two of you are supportive of each other and have worked through other issues together in the past. Pick your time wisely—when both of you are comfortable, when you have time to talk and aren’t likely to be interrupted—and ask if he’s got the energy to talk about a thing that you’re struggling with. Then lay it out like you have here. “Now that menopause is over, I’m feeling more into sex again. But I feel awkward initiating it, and am having trouble relaxing. I’m also stuck on fears of it disappearing again. Can we talk about how to work through this together?” I think you’ve got this.

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Dear How to Do It, 

I started seeing my wonderful and hot partner about a year ago, but a few months into our relationship, I started having trouble getting in the mood. I chalked some of that up to stress and then grief after a loss, but recently I’ve started to worry that it may just be a lack of attraction. Months ago, we had one of our only fights about it, with my partner jumping to the conclusion that I was done having sex forever and shutting down. Since then, we’ve had lots of sex that I’ve enjoyed, but I’ve developed some minor anxiety and dread when it comes to my partner focusing on me. I have no problem “taking care” of them, and seeing them turned on is what eventually allows me to get turned on. But when they start off by touching me, I just want them to stop. We’ve been using toys and trying new things, which I like, but I’ve noticed the most successful encounters tend to happen after I’ve had a few drinks. I’ve never had this problem before in a long term relationship. We don’t live in the same city, so I feel like I should be jumping their bones the minute I see them, but I end up feeling nervous whenever there’s an unspoken expectation of having sex. This is lessened at “weird times” like in the morning or afternoon. A potentially significant wrinkle here is that partner is non-binary, and previously, I’ve only been in relationships with cis men. I’m recently out as bi, and this has sparked an existential spiral where I worry that I’m actually just straight after all, although a friend told me she had similar issues with women that she just wasn’t all that crazy about. I love my partner and we’ve been able to communicate openly about sex so far, but this is really bothering me. Is it too soon for me to have lost attraction? Is this just anxiety? Is there a way for me to bring this up without making them feel undesirable?

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—Suddenly Stone

Dear SS,

I don’t like the idea of you drinking to get to a place where you’re open to sex. Please be careful with that one. Emily Nagoski’s Come As You Are might give you an understanding of responsive sexual desire, which it sounds like you’re experiencing. The better you understand it, the better you’ll be able to discuss it with your partner. The short version is that every person has a sexual accelerator, and sexual brakes, and some people have more spontaneous desire while others have more responsive desire. It sounds like your anxiety around this is mashing your brakes down hard, and your accelerator isn’t getting the type of engagement—seeing your partner experience pleasure—that you need in order to respond.

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I’m not sure how common this is, but in my own dating experience, I’ve found that long distance means I need a day or two once we’re in the same place to adjust to them as a human in the room instead of a brain on the other end of a phone. You might suggest that the two of you try waiting two to three days before doing anything sexual once you’re in the same space, and instead cuddle and engage in other non-sexual forms of physical connection like massage.

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Questioning whether we’re bisexual, hetero/homosexual, or broadly sexual can also throw us for a loop in a major way. Kate Bornstein’s My New Gender Workbook might help. Do the quizzes and the exercises, and see what you think about gender and your sexuality once you’ve gone through the whole text.

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When you go to your partner, frame it as something you’re struggling with and emphasize that you find them desirable and love them. “I’m having an issue that I don’t understand. I love you and I find you attractive. I’m also struggling with arousal in general, and I don’t know what to do. I have some suggestions though.” Pick your time wisely. Good luck.

More How to Do It

I’m a 29-year-old woman who has been seeing a guy for about a year now. We’re lovers and friends, but not in a committed relationship. Recently, he said something during sex and I can’t stop replaying it—I’m a little freaked out.

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