Sexplain It: The ‘Joke’ That Almost Ruined My Whole Threesome

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I’m Zachary Zane, a sex writer, author, and ethical Boyslut (a fancy way of saying I sleep with a lot of people, and I’m very, very open about it). Over the years, I’ve had my fair share of sexual experiences, dating and sleeping with hundreds of people of all genders and orientations. In doing so, I’ve learned a thing or two about navigating issues in the bedroom (and a bunch of other places, TBH). I’m here to answer your most pressing sex questions with thorough, actionable advice that isn’t just “communicate with your partner” because you know that already. Ask me anything—literally, anything—and I will gladly Sexplain It.

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My girlfriend and I met this woman on a swingers’ app, and we invited her over for a threesome. Before we got going, we sat in the living room and laid out boundaries. We explained that we were fairly new to the lifestyle, and we weren’t ready to do penetration yet, but everything else was on the table. She said that was fine…but then, she joked, “I’ll just have to slip it in when you’re not looking!”

We had no idea how to respond. We still went through with the threesome, since we’d done all this work to set it up, and it isn’t the easiest thing to find a third, but it was all pretty uncomfortable. WTF should we have done?


Dear Bad Thirds,

First, let’s do our best to avoid these situations in the future. If you and your girlfriend currently have a rule that you’re not having penetrative sex with other partners, I’d make that clear before the third comes over for a sexual encounter.

I’m just imagining if two guys hit me up to come over for a threesome, and I thought I was getting railed, so I ate light all day and spent an hour douching—and then when I got there, they informed me that they just wanted me to blow them. I’d be pretty frustrated! (Though I’d still do it, obviously.)

To be clear, I’m not justifying the third’s comment. Even if I were annoyed by a couple’s surprise boundary/rule, I wouldn’t make a joke (or maybe it wasn’t a joke) that’s like, “Welp, I might sexually assault you, so just a heads up—LOL!” That’s a wildly inappropriate thing to say. And honestly, it would make me question whether or not I’d ever want to sleep with her again because she seems a little bit like a wildcard (and who knows if she’d violate other boundaries in the future).

Back to my main point: If someone is coming over to have sex with you and your girlfriend, you should clearly communicate before they step foot in your home that you’re not up for penetrative sex. Send them something simple like this, adjusting for whatever feels accurate for the two of you: “Hey, just a heads up! We don’t do penetration with a third the first time we meet.” If she’s cool with that, great! And if she’s not, at least you’ll know before you’re three feet from the bedroom.

As for directly responding to a comment like that in real-time? There’s a way to be firm and direct without being awkward or “ruining the moment.” You could say something like, “Oh, don’t get me wrong, we love penetration too, but we have a rule that we’re not doing it with other partners right now.”

If you re-state your boundaries and the third just isn’t getting it, don’t fuck her! Say, “Hey, sorry; we’re actually not feeling this, so we’re going to have to ask you to leave.” Will that be awkward? YES! Will you live? Also, YES! And trust me, it’s much better to have an awkward five minutes than having sex with someone you and your girlfriend do not want to bone.

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