How to Do It

My Greatest Sexual Fantasy Is Finally Within My Grasp—but, Uh, There’s a Problem

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Photo illustration by Slate. Photo by Honored_Member/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!

Every week, the crew responds to a bonus question in chat form.

Dear How to Do It,

After having hot fantasies about threesomes (I am a woman) for years, I might be on the precipice of finally making it happen. My preference was always two guys, but I thought I would be OK if the third was a woman—guys seem to have some hang-ups about FMM threesomes. Now, however, I’ve found two men who are theoretically down for it. One little problem: I have zero idea how to do this. How is it not just incredibly awkward? Do you tell them what day/time and … sit in between them for Netflix and chill? Offer snacks and make small talk? The porn example is not necessarily how I want to do it, where she is being railed and choking on the other’s dick (too much). Do I as the instigator play middle man in advance to get the list of yes and no items from both of them? As a note, I have already had sex with each of them over the years, if not recently. What are some practical ways to go about this that isn’t fake porn or erotic fanfic to start and keep it moving?

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—The Middle

Rich: I absolutely love this question, as it demands practical guidance that isn’t out there set in stone. There’s really no agreed-upon etiquette for coordinating group sex outside of the very rough basics of respect and communication.

Stoya: I’d point to certain pornography as an example of how to communicate well, but our writer seems averse to the medium.

Rich: That’s true! I think she can conduct herself as she would in any casual hook-up really, just in terms of her general demeanor. An important thing to keep in mind is that discussing the awkwardness of a potentially awkward situation is bound to make it more awkward. Play it cool.

Stoya: Alternately, sex, like most things, is always awkward the first few times you do it.

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Rich: When a hook-up comes over, what do you do? Probably chat for a bit, depending on how well you know them, before you start making direct physical connection. You’re just basically doing that with two people instead of one. I think the most awkward phase is the pre-planning phase, if you are in fact the coordinator, as it involves asking people if they’re interested, and then sending them each other’s pictures and holding your breath. “I’m sorry the other person isn’t into you” is a shitty message to have to deliver. I’m not sure how it works with ostensibly straight guys, though. Like does a straight guy need to see the picture of a guy he’s going to be in a threesome with (but not having direct sexual contact with during said threesome)? “FMM” could imply a bisexual threesome (as opposed to “MFM”), but I’m not sure that’s what she meant.

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Stoya: Well … OK. Let’s do “binary sexual orientation” for a minute. If we’re working with potential threesome partners who consider themselves straight, they might actually be offended by a picture of the other man. Because they’re doing this “for the woman.” To me, that’s a huge warning sign. Because having two penises inside your delicate bits that are operated by people who are afraid of coming into contact with the other’s cock seems like it carries a high risk of mechanical injury. But also this woman might not want double penetration, so that might not be an issue of concern.

Rich: Navigating the emotions of straight men seems like a most exhausting burden to take on?

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Stoya: Yeah, that does seem to be changing, but emotional labor is real.

Rich: My boyfriend and I were once invited to a “naked cocktail party” that was obviously going to result in an orgy. We were the last to arrive. Just a bunch of naked guys standing around with drinks in hand and dicks out. And then we had to come in and sheepishly say hi and disrobe. Talk about awkward!

Stoya: Oh no!

Rich: But you know, once everyone is having a good time, that awkwardness dissipates.

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Stoya: You make a very good point about timing. She should probably prepare some light, not particularly suggestive activity in case one of the MMs is late.

Rich: Listening to music, going through a coffee table book, video games …

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Stoya: And she would do well to make sure everyone is on the same page about whether this is going to be a big ol’ queer puddle or a “don’t touch my dick, I don’t want to touch your balls” situation.

Rich: Yeah, I think that would be a good thing to figure out in the planning stages and then maybe go over once they’re all in the same room. It’s a good way to cement the boundaries and shift the conversation to sex, too.

Stoya: For sure. Even between porn performers  who’ve worked together a number of times over a period of years, it’s generally considered best practices to talk about yeses and nos on the day of the scene.

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Rich: If she’s the host, part of her assumed job is to help make people comfortable, which is yet more emotional labor, but also pretty necessary to ensure a good time is had by all.

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Stoya: I’m wondering if she remembers what makes each of her M’s comfortable from her previous experiences with each of them. And how she segued into sex with them individually.

Rich: This could also be ascertained by talking with them separately before—–feel them out, ask them what would make them comfortable. You know, she’s the leader here, but this can be a collaborative process.

More to How to Do It

I’m a woman who has been with my boyfriend a year, and the sex has been great. I feel very lucky. My partner has said, however, that he needs to ejaculate every day. Masturbating daily is something he has done since he was a teen, sometimes more. If we don’t have sex, he uses porn. It bothers me. It’s frustrating when we just had sex eight hours ago, and I wake up to him on a do-it-yourself project. Isn’t this unhealthy?

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