How to Do It

My Friend Is Plotting to Steal My Hot, Charcuterie-Slinging Lover

Her recent proposal was a nice try, but I see her game.

Woman looking upset while on a phone with a neon of three people behind her.
Photo illustration by Slate. Photo by CentralITAlliance/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 an attractive sixtysomething single woman who’s had two bad marriages that included nonexistent sex in the first one and boring sex in the second. Then I had five, count them, five live-in boyfriends who were economically challenged and rushed me into moving in and the sex was so-so. After the last live-in relationship, I decided to get on Tinder and dabble in casual sex, which has worked out remarkably well. Then six months before COVID hit, I met this man who is in amazing physical shape and seven years my junior. We fell into seeing each other regularly, but didn’t qualify the relationship as being an item. I like the ambiguity. It keeps things exciting. Nothing has dissipated in our wonton lust for each other. (How amazing to be writing those words down at my age!)

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Enter a very good and dear friend who has always had to beat the men off her with a stick. She broke up her marriage years ago to get with an older man, and they’ve been a couple, but not married, for 20 years at least. She lives in another state (so really it’s a moot point right now since its COVID-19 time), but she brought up having a ménage à trois with my man and me. This freaked me out and I just said, “There will be no ménage à trois!” To me, this was something a kinky, porn watching man suggests from time to time, and I declined. A) I’m not attracted to women. B) Is this something her long-term man knows she suggested? I felt somewhat sad for her, as I’m having sex galore and maybe her man has something going on with E.D., so I suggested I’d gladly be happy if she had a fling with two men from my past (one of which she also had a fling with over 30 years ago) who are still very good in bed (the last time I checked), and I would not care in the least if she pursued.

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She said, “That would be a hard NO!” Like I was being inappropriate. OK, so, it’s a hard NO with the threesome. My question is, when are threesomes beneficial for everyone involved? She just wanted to have hot sex with my lover and used a threesome as a method to get to him, right? He actually has a very demanding work schedule in a Brazilian high-end charcuterie, and we have our little trysts in the wee hours of the night when he gets off work. She just wants to sweep in and bang him and think we could go on as if nothing has happened? I think a lot of her significant other and think of him like a brother, and maybe they have some kind of arrangement for her, but I’m not her facilitator for finding hot men.

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—Not Sharing

Dear N.S.,

I love this lusty vignette of senior sexual politics. I feel like you have the premise for a TV pilot on your hands, should you choose to pursue the avenue of screenwriting. I mean, the details alone! Brazilian high-end charcuterie?!? Chef’s kiss.

Given how clear it is that you enjoy sharing (your story, that is), I’m guessing you got to flapping your lips about this new injection of hunk into your life, and your good friend wanted to break a piece off. Depending on the attitudes of the parties involved, such a request could go exactly as you theorize (banging him and thinking you could go on as if nothing has happened) or whip up an immediate catastrophe. You handled this perfectly by shutting it down and offering to hook her up with some backup dick you have more or less on reserve.

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Threesomes are beneficial for everyone involved when everyone wants to be involved and is aware of what such an encounter is and isn’t. Ideally, everyone is equally attracted to everyone else. That’s not always the reality, but in order for it to go well, there should be at least some attraction between every party involved. People certainly will sleep with a couple because they are into only one of the partners (like ordering the surf and turf because lobster tail doesn’t appear by itself on the menu). But when you take one for a team that’s in such close proximity, your playmates are bound to notice. Having sex with two other people for the sake of having sex with one of them is the recipe for bad sex, drama, and maybe even tears. (I’ve seen ’em! In bed, dicks out, wet cheeks … on a face.) It should be avoided, and you did just that by seeing it coming and preventing it. Another satisfying episode; would watch next week’s.

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Dear How to Do It,

I’m a bisexual and multiracial cis woman, who’s been casually dating around for the past year and change. Before that, I was cohabiting with a long-term partner, and so now I admittedly feel out of practice. The good news is, I don’t have a hard time finding suitors these days; the bad news is, most people I’ve gone on dates with express their attraction to me by fixating on my race in very creepy ways. (Think: remarks about my hair, my nose, my lips, my butt, what our babies would look like.) In two instances, people asked me to dance for them or speak in my parents’ language on command—in a sexy way. I tell them I’d rather not.

Not all of them are white, but in any event, it disturbs me. I have a lot of trauma related to racism growing up, and I hate feeling singled out or preyed upon in this way. I think there are plenty of fun things about me that are not my race nor my queerness. So I’ve broken things off with all of them, vaguely citing lack of chemistry. But now one woman just won’t leave me alone, and treats me as her go-to resource for education. (I just ignore.) How the hell can I weed these people out before we even get to the bedroom? Unlike many queer women, I don’t wanna process trauma with people I’m just getting to know… I just wanna get laid without feeling disgusted! How would you suggest I handle this?

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—Fetishist Creeps

Dear F.C.,

My general philosophy is that weeding people out is worth the time it takes—the sense of closure in “absolutely not” after putting forth effort to get to know someone is a solid consolation prize in the absence of the primary goal of said interaction (an enduring relationship). In your particular case, however, it wouldn’t be appropriate for me as a white guy to encourage you to keep traumatizing yourself, and at any rate, I don’t think you should. For some practical help here, I recently discussed your question with Damona Hoffman, a certified dating coach and host of the Dates and Mates podcast. In case you’re wondering, Hoffman is biracial (Black and white). She said that she gets questions like yours often.

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Hoffman told me by phone that because your suitors are of various races and yet you keep feeling the same way, “the constant is trauma that needs to be processed, and if it’s not being processed in the right place with the right people, it’s going to be processed everywhere.” Maybe therapy or even just talking to friends with similar experiences/identities would be a good place to start.

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As for dating, Hoffman gave a civic-minded answer that challenges you to endure some discomfort. “I have a different perspective on this than a lot of other dating coaches of color,” she explained. “I think that part of the education process is walking through a little bit of discomfort with people as they are starting to understand where the lines are. For so long, we’ve kept our mouths shut and accepted a lot of the inherent racism in our society.
We’re at a really interesting time in our history where we’re allowed to speak up and express that some of these words or microaggressions are no longer going to be tolerated. I think for us as a society to be able to bridge this divide, we have to have some of these uncomfortable conversations.”

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Hoffman suggested that instead of shutting things down as soon as someone says something that strikes you as off, it might be useful to communicate boundaries. “If they understand this was a line and a retraumatizing event but, ‘I really like her and I need to make a change because I’ve made this person I care about uncomfortable,’ that’s where things get really interesting.” After all, someone who listens and takes your boundaries seriously is indicating that they might be a good partner.

Or maybe not! Hoffman said that if this keeps happening, it’s indicating that you’re missing signs early on. I floated the idea of a pre-date screening session in which you might quiz your potential date on a host of social justice issues. (Have they been to BLM protests? Do they have any sense of issues that people of multiracial identities face? Have they read Black authors?) Hoffman said she doesn’t love the idea of “dating by checklist,” but that she does generally advise people to have in-depth conversations early on in order to check whether the person you’re talking to passes through your filters. This discussion is conducted “not in a way that you’re interviewing them, but in a way that you’re trading stories and getting to understand their perspective on race and culture and social justice.”

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But her main advice to you is to process your trauma in more suitable venues than on dates with strangers, and to work on gaining the confidence to talk through the issues as they present. I don’t think you have any obligation to make the world a better place, and a turn-off is a turn-off, but I do love the idea of building tolerance to some bullshit and telling people exactly what they’re doing wrong—it might make you stronger and/or offer relief by catharsis.

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Dear How to Do It,

I am a 75-year-old man with E.D. I won’t go into the morality of this, but I have recently employed services of several escorts. The first lady was able to make me climax with oral stimulation surprisingly faster than I expected. It was surprising because the meds I take (finasteride) make it very difficult to climax without significant stimulation. In addition to oral, I was hoping with visual stimulation and giving her oral, I could achieve an erection capable of penetration. It did not work. With a second much younger, more visually stimulating escort, I was frustrated again by not being able to penetrate. She also did not have the skills to make me climax orally, which added to my frustration. This led me to purchase a vacuum pump on Amazon, of all places. I want to incorporate the use of the vacuum in my next session with this escort, having her help me. Should I wait for the urge brought on my foreplay until I ask her to pump me or should I do it before hand? How long should I leave it in the pump before it will be “ready”? I’ve tried the pump solo, but the mood is not sufficient. I also have a ring, which is supposed to help maintain. If, using a pump, I am able to attain an erection, will the sensation be sufficient for me to climax?

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—Old Joe

Dear Joe,

Don’t worry about the “morality” of the situation—this is a no-judgment zone for sex work. I think you should treat your escorts as you would any other partners and inform them of what you’re looking to do during your encounter. They are, after all, people too, who will have their own feelings about the situation. That said, I don’t imagine you’ll find too many people put off by your pump request—squeezing a bulb a few times is not very physically taxing work, all things considered. But do let them consider that for themselves.

Your more specific questions about how it will all function are impossible for me to answer confidently—you’re just going to have to trial-and-error this because I don’t know what your dick’s gonna do. Dicks, they’re all different! I think it would be wise to talk to your doctor about E.D. medication. “Vacuum erection devices (VEDs) don’t work well,” wrote Charles Welliver, a doctor and the director of men’s health at Albany Medical College, in an email after I showed him your question. (Welliver is my go-to urologist source.) “They have amongst the lowest (if not the lowest) patient satisfaction scores when we look at the different treatments for E.D. They are nice in that he can get one without doctor’s prescription but generally are usually more frustration than they are worth.” Welliver urges you to not let shame get in the way of talking to a doctor about your E.D. “Those of us who specialize in these types of problems are pretty used to guys being embarrassed about it,” he wrote.

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Dear How to Do It,

My husband and I have been married for over 15 years and have a varied and satisfying sex life. Here’s the catch: Although I’m happy with our sex together, I can only seem to have a truly mind-blowing orgasm by masturbating. And it’s often a long and arduous process. It can take a half-hour! I barely have the patience for it myself, let alone trying to do it together. So, many nights, while he dozes after sex, I secretly masturbate lying in bed by his side to “top off” the evening. It’s become a habit and I feel guilty and sneaky. We have tried masturbating together and it’s virtually impossible for me to get off. So, in some ways, this arrangement works. But I suspect it’s not really healthy. Why don’t I tell him? I don’t want to hurt his feelings, plus I really have no complaints about our sex together. It’s fun and satisfying. Just not … over-the-top. Am I doing it wrong?

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—Dancing by Myself

Dear Dancing,

As described, this seems like a benign workaround, though it does bring up consent issues—it’s not advisable to be engaging in sexual activity in the same bed as someone who is unaware. The real issue here is why you are doing this secretly. Masturbating after sex is part of your process, and that’s OK—it’s not taking away from a sex life with your husband that you enjoy despite its inability to deliver orgasms. You said you don’t want to hurt is feelings, but he is aware that you aren’t coming when you have sex (even manual sex) with him, right? If you’re faking orgasms, well, you’re contributing to a problem big enough that you’ve decided to employ the help of a stranger. Fessing up would help you declutter, if you are in fact faking it.

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I wonder why else your lips might be tight here. Are you afraid that if you told him, he’d want to help out, thus defeating any chance of coming? Or is part of the thrill the fact that you’re getting off in the same bed with him without his knowledge? The former is understandable (though not strictly ideal); the latter is fetishizing his lack of consent, and that gets a no from me. Ideally, you’d have a conversation with him about this, leading with how much you enjoy having sex with him (tell him How to Do It thinks you’re enlightened for being able to recognize that sex can be enjoyable even if it doesn’t produce orgasms) and finish yourself off in another room, or in bed with him with his OK. This doesn’t have to be a psychodrama, and a well-articulated conversation could clear your conscience and leave plenty of space for your self-administered, mind-blowing orgasms.

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— Rich

More How to Do It

I have a close friend whom I was once intimate with who asks me questions about sexuality, specifically bisexuality and bi-erasure in the LGBTQ community. He’s in his late 30s, and was raised in a homophobic Catholic environment. I am a woman, also late 30s, but am openly bi and queer. I think my friend is looking to me for acceptance of latent bisexuality, but I don’t know how to provide that support if he can’t admit it to himself. I am in a position of trust with him. I want to help him, but he is too shy to ask outright and deeply introverted, so I don’t think I can bring a third-party bisexual man into our friendship to demonstrate the possibility of the life he could choose. How can I best be supportive without any kind of confrontational outing?

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