How to Do It

My Partner’s Sexual History Is Way More Intense Than I Thought

Hearing about it is a huge turn-on, but she’s shy. How do I get her to tell me more?

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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 have been with the most amazing woman for the past several years. We are older and each married before, each with kids. Our fast-paced life is complicated at times, but mostly we have fun, easy conversations, similar values, and great sex. I am totally smitten with her. Recently, through a combination of causal conversation, a few direct questions, and just a little bit of math, I have come to understand my partner’s sexual history is a bit more, and possibly quite a bit more, colorful than I had led myself to believe. She did present as a “simple woman” with a very “boring” past, so some of this is just shock, but I am surprised how much this new information is affecting me.

The “problem” is: I want more! I am dying to hear details about her past sexual encounters, and the more random or casual the better. Ex-husband sex does not interest me, but the one-nighters? I’m in! It totally turns me on! I know this has a little “cuckhold” sound to it, and I accept that. I’m way too insecure for supporting actual sex with another man, but the experiences she had before meeting me, well that’s a different story. I’m wondering how to get her to share more information? She claims she doesn’t have any more titillating stories, but I’m becoming less and less apt to believe it. She is also embarrassed, or at least uncomfortable, with some of her choices, but I’m totally fascinated. I know if I have to, I could put it to bed, so to speak, but I just don’t want to.

—Bedtime Stories

Dear Bedtime Stories,

This is her story, which means she gets to decide what she does with it. Not only am I not going to help you coerce her into sharing information that she has already expressed discomfort and embarrassment in revealing the little that you do know, I’m going to request that you stop aspiring to milk her for more info. Be happy with what you have. My only pro-social recommendation for you would be to foster an environment of free sharing by setting the tone and being extremely open about your history. You can lead by example, but you can’t force her hand. Stop being so selfish. You’re not entitled to her past.

Dear How to Do It,

I am a mid-50s widowed man. It has been several years since my wife passed, and I have reentered the social scene to some degree. A couple of years ago I started exploring my long dormant bisexual tendencies with a married couple. This has evolved to my hosting a group event every few weeks, usually including this couple and a few others. We have dinner, drinks, maybe smoke a little weed, watch some porn and then get naked for some good clean fun. Everything is done in a very safe, controlled fashion, and nobody is pressured to participate. We don’t recruit by social media, instead relying on word of mouth/friend-of-a-friend contacts. The groups usually number five to seven individuals, and our cumulative total for participants over time has been about 25 people. Most of the participants other than the first couple have been single guys or gals in their 20s and 30s. Our activities are currently on hold due to the COVID-19 pandemic.

Recently, an acquaintance approached me about our groups. I thought that he was interested in participating, so explained the basics to him. He was very put off by the concept, feeling that we were somehow taking advantage of these younger people. I tried to explain that there is no pressure or coercion, that everyone is there of their own free will and that there is no financial or other compensation. This encounter has left me wondering if there is something to his opinion about this, and if we should resume our activities when it is considered safe to congregate again.

—Curious Host

Dear Curious Host,

I disagree with your acquaintance. I don’t think there’s anything inherently wrong with having sex with people who are younger than you in the casual, hookup scenario that you describe. (Attempting to build a lasting emotional connection with someone who’s decades your junior, however, is another, more complicated matter.) Based on your telling, the people attending your parties are horny and willing, and if they weren’t having sex with you, someone who’s 20-to-30 years older than most of them, they’d be having sex with someone else. These are all adults capable of consent, and in all likelihood, they attend and return because they enjoy the environment you’ve created. Your available body is part of that environment. (I’m giving you the benefit of the doubt here that the substances that are used are being done in moderation and that no one is incapacitated beyond being able to properly consent, by the way.)

Why not, though, bring up this topic during your next get-together? It’s an interesting enough thing to discuss, and such a conversation could erase the ambiguity that your associate’s read on the situation conjured. You may find that communicating openly on this matter provides relief and perhaps an even stronger connection. And connected sex is a very good thing.

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Dear How to Do It,

I am a single, straight woman in her mid-40s. I have never been able to have an orgasm through penetration, and I’m fine with that. I also am only able to have one orgasm via clitoral stimulation, and after that, my clit is too sensitive to be touched for several hours. I’m not shy about telling my sexual partners about all of this, but all the guys I’ve met seem to take this as a personal challenge. They want to be “the one” to make me have a G-spot orgasm or have multiple clitoral orgasms, and then proceed to try to do just that, and it’s always super uncomfortable and not at all enjoyable for me. I am perfectly satisfied with a single, intense orgasm, but other than bluntly telling my partners this (which I already do), what more can be done? Should I be stating it in different terms? Am I just coming across a bunch of duds? At this point, as much as I crave the touch of a man, I’m feeling like I get more satisfaction and less frustration from solo play, which sucks!

—One and Done!

Dear One and Done,

The kind of directness you are displaying is the kind off directness that I prescribe. From what I can tell, you’re doing everything right, and your partners are effectively disregarding your self-reporting in favor of a fantasy about inducing female pleasure. They’re not listening to you, so the best you can do is speak to be heard. When talking to partners about this, I would emphasize the positive (perhaps softening the bluntness but not the specificity), by explaining that in fact the best way to please you is via a single clitoral orgasm. That is your version of the idealized pleasure that these guys think can only be achieved by manipulating your G-spot/multiple orgasms. It seems quite remedial, but you may have to point out to them that all bodies are different, and that you know yours well enough to be sure of exactly what you want and how to get it. Some guys know this, many do not, and it’s up to you as to whether you’d like to go above and beyond and be not only a sex partner, but also a teacher. I do think that you have run into some duds, and the best you can do with them is see them for what they are and move on. Clearly, those who want to be “the one” are not it.

Dear How to Do It,

I’m a 35-year-old woman married to a very loving 32-year-old man. We’ve been together for a few years, and usually had sex once every one to two weeks. I only orgasm through masturbation, but I crave more frequent sex and have a higher libido than him. He’s always had a bad back and bad knees and has always had bad generalized anxiety.

A year ago, he started experiencing occasional twinges in his penis when urinating. He has taken medical tests, but they haven’t found a diagnosis. I also experienced vulvodynia around the same time; no diagnosis for me either, but for me it went away quickly.

For the past year, he rarely ever followed my sexual advances and never initiated sex, but he purchased masturbation sleeves and pleasures himself in private. The two times we’ve had sex in the last 12 months, he insisted on wearing a condom just because he doesn’t know what’s wrong with his penis. It doesn’t physically hurt him to be inside my vagina, my mouth, or my hands, but he tells me he just doesn’t feel relaxed enough to let me pleasure his penis. However, we do continue to be physically intimate, playing with each other’s clothed bodies whenever we’re in the same room together. But he doesn’t know when he will feel like having sex with me again.

I don’t have strong sexual needs, but I really miss the sexual intimacy, and I feel like I deserve more in a marriage. In theory, I’ve always wanted to experiment with other men; and when we discussed it recently, he said he is fine opening up our marriage. But for me, the prospect of meeting strangers out of desperation is deeply intimidating and sad. I feel so much sorrow that something so minor has completely ended our sex life.

—Worried Wife

Dear Worried Wife,

Assuming that every single condition that is associated with painful urination has been ruled out (including prostatitis, UTI, kidney stone, and, of course, STDs) and that this isn’t an issue of chemical sensitivity to certain hygiene/household products, it seems like his reaction is more a manifestation of his anxiety. Or worse. Could it be an excuse to avoid sex? I’m afraid that’s what it is, dear writer, which means that the problem that has completely ended your sex life might be less minor than you think.

But regardless of his motivation, I think he indeed has issues with sex that could use addressing. And I agree, you deserve more. I have a feeling that his issues are too deep for you to tackle and resolve on your own, so ask him if he would consider marriage counseling. Opening up your relationship could have positive effects, as it would allow you to both stay with a man who isn’t satisfying you sexually and be satisfied sexually. But nonmonogamy isn’t for everyone. Sex outside your marriage doesn’t have to be desperate or sad, but if it makes you feel that way, engaging in it will likely create more problems than it solves.

One thing to consider is what you will do if the situation doesn’t improve—if, in fact, this is it? Can you stay with a partner who does not provide the frequency of sex that you favor? Could you possibly manage the situation via other partners? Or do you need your significant other to also be your sole means of sex? And if he’s not … do you leave? Your future may be staring you in the face, but know that you have options to make your life work for you.

— Rich

More How to Do It

Lately my boyfriend and I have been filming ourselves having sex, and we both love it. It started out simple with just a cellphone video, but now we’re doing multiple angles, lighting, the works. We love watching and rewatching it. What can I say, we think we’re hot! I’ve been wanting to experiment with posting the videos somewhere. I like the idea of other people watching us do it, leaving comments or even requests, etc. My boyfriend is also game. But we’re both worried about, well, videos of us having sex on the internet. We could try to make it so neither of our faces shows, but is there another way to safely live out this fantasy? We’ve also talked about having people come over to watch us do it, but have no idea how to find these people and whether anyone would be game to simply watch us fuck without joining in. Any ideas?