How the Hell Do You Initiate a Threesome?

Lindsey Lanquist
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How the Hell Do You Initiate a Threesome?
Photo: Allison Kahler.

Thus far in life, I’ve had exactly one opportunity to have a threesome. Two of my friends and I had talked about it: We were mutually interested in each other, and we were mutually interested in having a threesome. The next time we’d be in the same place was over the holidays, so we tentatively agreed to do it then.

Great, step one accomplished, I thought to myself. We know we want to make it happen, but how, exactly, are we going to?

Concerns began to swarm my head. Would we meet at one of our houses? None of us lived alone, so how were we going to make that work? Clearly, we’d need alcohol, but sitting around in a room drinking and awkwardly anticipating group sex seemed super weird. OK, so we’d go out first. We’d drink there and casually hang out like we always do—that’d be normal enough. Then, one thing would lead to another and we’d… take a 30-minute Uber back to my place and then have a threesome? It’s not like we could hook up in the Uber; we’d have to get all hot and bothered and then spend 30 minutes cooling down before getting to the main event. What if one of us fell asleep on the way there?

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The more I thought about it, the more mental roadblocks I hit. Whenever I’d thought about threesomes before, they were merely the stuff of fantasies. Now that there were logistics to deal with, the whole thing seemed cumbersome, awkward and completely unsexy. But there were plenty of people in this world who had threesomes and made it work—what did they know that I didn’t?

To find the answer(s) to this question, I put out an open call online. I simply sent the question, “Have you had a threesome?” into the digital universe and waited for actual threesome-havers to get back to me. And a handful of them did. Here, those six people teach me exactly how to have a threesome—from start to finish, because it’s really the start that’s the confusing part, right?

Clearly, we’d need alcohol, but sitting around in a room drinking and awkwardly anticipating group sex seemed super weird.

Finding Your Partner(s) and Making the Ask

There’s no singular right way to make a threesome happen. Steff* was approached by a guy she’d been hooking up with; he was in an open relationship, and his partner had mentioned she’d like to have sex with both of them, together. Stella* was talking to her friend about their recent hookups when she mentioned her friend’s partner sounded so incredible she wanted to sleep with him, too. Her friend told her she could—as long as it was a ménage-à-trois rather than a ménage-à-deux.

And in what’s probably the most quintessential threesome story of all time, Demi* was approached by her former lover’s current wife; she wanted to give her husband a birthday present he’d cherish forever—in this case, a threesome with the two of them.

These were just three of the people I’d talked to (and just a few of the threesomes those people have had), but in each of these cases, connection arose pretty organically. Steff was already hooking up with her friend with benefits, Stella was super close with her friend and Demi had already slept with the birthday boy.

But what happens if you want to have a threesome with someone you don’t already know?

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For starters, you can look online. Blair*, who’s married but in an open relationship, uses dating apps, and she’s careful to be clear about her relationship status in her bio. Sometimes, her matches will express interest in sleeping with both her and her husband (that’s how one of her most recent threesomes came to fruition).

Jim* also turns to online dating—though the sites he uses (adultfriendfinder.com, swinglifestyle.com) are much more targeted toward group sex than, say, Tinder. “It’s so quick and to the point,” he says. “Like any kind of dating, you’re still dealing with a lot of flaky people. But most of the guesswork is taken out of it.”

And of course, if online dating isn’t your scene, you can still do things the old-fashioned way. April says she and her husband had their second threesome with a woman they met at a convention. They’d run into her a few times, talked some and flirted a little. By the end of it, they just decided to ask her to their house for drinks.

“We just said something like, ‘You’re really cute. We’re getting along. Why don’t you come over to our place later?’” April says. “I mean, you’re already feeling comfortable with that person—you already have a rapport going.” So as you would with anyone, just ask them out. “The worst they can say is, ‘No. I’m flattered, but sorry!’” she says. “Best case scenario, they’re like, ‘Sure.’”

We just said something like, ‘You’re really cute. We’re getting along. Why don’t you come over to our place later?’

Preparing for a Threesome—the Right Way

Once everyone’s on board, you should give yourselves some time to think it over. One of Steff’s threesomes involved a guy she was in an open relationship with (her partner) and a guy she was hooking up with (her friend with benefits). Her partner suggested the threesome, so she mentioned it to her friend with benefits—but she made sure to give him a week or two to consider it.

“We didn’t want to rush into it,” she says. “You know how people talk about sex ruining friendships? The same is true, even if there are more than two people having sex.” (In fact, she says, the closer you are, the more you should talk about it.) The key is to make sure it’s an emotionally and physically healthy encounter. So after making the ask and thinking it over, get ready for a whole new conversation: one about safe sex.

“There are definitely some things you’ll want to discuss in advance,” Steff says. Protection is a big one. Will all three of you be fluid bonded (sharing fluids—namely, ejaculate)? If not, how are you going to ensure that? When was the last time everyone was tested? What forms of birth control will you be using? “You’ll need more condoms than you think you will,” Steff says, laughing.

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Then, there are other questions to consider. “No threesome will ever be completely equal,” Steff says. Her second threesome, for instance, involved two of her best guy friends. Things ended up falling apart before any of them had sex, but even as they were engaging in three-way foreplay, questions arose—like, who gets to take off Steff’s shirt? Should she, or should one of them?

“Each of the participants should figure out whether they’re willing (or unwilling) to forgo certain things,” Steff says. “If you have a guy and two girls, and he’s a one-and-done type, then obviously both of you aren’t going to get to have sex with him during the encounter. So who’s OK with not getting that?”

And of course, you’ll want to make sure everyone is truly down to have a threesome. “Make sure you’ve talked it through and that the other people are on board—that it’s not just you turning the screws because you want this fantasy to happen,” Jim says. “There have been a few times where it became obvious to me that one person wasn’t feeling it and that they were probably just there to make their partner happy.”

Though these conversations might seem daunting, Blair promises they’ll help you have more fun later. “It’s so important for you to be comfortable and not be worrying about anything while you’re in the moment,” she says. “The greatest thing you can do for your own enjoyment is to know that you’re in a situation you feel comfortable with, where everyone respects each others’ wishes.”

You’ll need more condoms than you think you will.

Setting the Scene the Night of

Once you’ve established that everyone involved is definitely down to have a threesome, it’s time to set a date—and, yes, you might actually want to set a date. “We picked a day and time,” Stella says. “We just said: We’ll hang out, have a couple drinks, relax, and it’ll all unfold.”

If whipping out a calendar and picking a date seems too arbitrary to you, you can schedule your threesome to coincide with a specific event, like a party. “Day of, I went over to their house for a house-party-esque thing,” Steff says. “At some point, the guy just came over to me and his partner and said, ‘Hey, want to go see my bedroom?’ which was code for, ‘Hey, let’s get this started.’”

And of course, for threesomes that originate more day-of—like April’s at the convention or Blair’s on the dating app—you just pick things up a few hours later. No calendar involved.

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Once you’re there, you might want to put on some music and pour a few drinks, Stella says. You might also just want to get straight to the action. “It’s actually really similar to how normal sexual encounters go down,” Steff says. Sometimes, there’s hanging out beforehand. Sometimes, there isn’t. Just initiate when you feel comfortable, and trust that one thing will lead to another.

“Be open to whatever might happen,” Blair says, when I ask her what advice she has for threesome-hopefuls. “Going in with a lot of rules makes it difficult for everyone to relax and have fun.” By rules, she’s alluding to some of the restrictions couples place on each other in threesomes. The third person can perform oral sex on my partner, but I’m not OK with them having sex—stuff like that.

“Part of that is just good manners. You want to welcome your guest—whether that guest is invited to dinner or your bedroom,” Blair says. “You don’t want to treat somebody like an object that’s there to help you fulfill a fantasy. They’re a person.”

So if you’re in a couple inviting a third person in for a threesome, be mindful of how everyone else is going. And if you’re the third person who’s been invited to join a couple, don’t be afraid to self-advocate. “Only you can control your own happiness with the situation,” Steff says. “So don’t be afraid to advocate for yourself.”

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And remember, you won’t know how you’ll react until you’re in the situation. “It might seem sexy, but then some vanilla jealousy might kick in,” Jim says. Cut yourself a break if it does, but don’t hold yourself back just because you’re not sure if it might.

“From my perspective, threesomes can be a beautiful thing. They can really strengthen a relationship, and I think a lot of people might not see that,” Jim says. “But my experience has been that when you open up and separate the sex, jealousy and love elements of it, you build a whole new level of trust. It’s pretty hot.”

*name has been changed

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