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How to Have a Successful Threesome

One of the most classic and universal fantasies and, to some, the most taboo, almost all of us have thought about the idea of a threesome at one point. For some of us, it’s more than a fantasy; it’s something we’d like to try for ourselves. But how do you manage to pull off having an actual threesome — and how do you make sure it’s not wildly messy? Here’s what I recommend for making your threesome happen successfully.
Imagine your perfect threesome

As with any relational project that carries some stakes for your mind and heart — that is to say, all of them — it’s best to go in with as clear an idea as possible of what you want. When you imagine a threesome, what are you hoping for? Is this about adding a third person for one thrilling night to a pre-existing relationship? Do you fantasize about joining two strangers or at least casual partners? Would it feel affirming and exciting to have a threesome with existing friends (or friends with benefits)? Are there gender(s) you specifically want to include?
What dynamics are you — or a partner — looking for in a threesome? Is the core of the fantasy about being at two other peoples’ whim, or enjoying a new, novel third person and being in control? Are there actions you definitely want to try or have done to you, or that you know you want to avoid? Are you hoping for a warm, intimate experience where everyone involved cuddles afterward and gets breakfast in the morning to debrief, or are you turned on by the idea of a casual encounter, almost quasi-anonymous? Being clear about what you’re looking for helps you communicate clearly and directly with other potential threesome participants making it more likely you’ll get what you’re looking for — and so will they.
Finding threesome participants

Arguably more trepidatious than planning and executing a threesome is finding three people with the same vision who are all on board with it. While I won’t discourage anyone who’s starting from scratch, by far the easiest way to get started on assembling a threesome is to have at least two people out of the three already on board: yourself and one other person.
For many people, this looks like seeking a third person — often called a “unicorn” — to join you and an established partner that you’re in a committed relationship with. However, that doesn’t have to be the only arrangement. Perhaps you’ve been seeing multiple people non-exclusively as you casually date, and you’d like to have a threesome with one (or more) of your casual partners; maybe you have a friend who’s open to becoming a friend with benefits, a threesome being one of the potential benefits on the table. If you are dating casually and interested in a threesome, consider sharing that fact with your dates — maybe they know someone who’d love to join you.
Once you have two people (including yourself) interested in a threesome, the key is to find a third. Many people use dating apps for this; if you use apps, you’ve likely seen posts from two people looking for a third, either for a full-on relationship or for a one-time thing. Depending on the circumstance, it isn’t out of the question to meet a third person “in the wild” — if you’re at a certain kind of party or hang out in sexually open circles, it might not be impossible to approach someone in person as a couple. Just make it clear from the outset what your intentions are; it can feel like a bait-and-switch to feel like you’re hitting it off with someone cute that you think might want to be your partner only to find out they already have one, and they’re auditioning you for both of them.
Manage expectations — including your own

It’s important to communicate explicitly and directly about wants, needs, expectations, boundaries, and desires before all sexual encounters — yes, even casual sex.
This is arguably even more important in the context of threesomes; if two of the people involved are in a couple, they have the privilege of knowing a lot of each others’ background and likes and dislikes; the person joining in has none of that, and is in the vulnerable position of having to ask two new people to learn about and respect their boundaries.
Because threesomes can for some carry some loaded connotations — even participants who are excited and enthusiastic could find themselves feeling jealous, unsure, fetishized, or needing a break in the middle of things — it’s helpful to have very thoughtful and nonjudgmental conversations up front, as well as establishing that consent can be withdrawn or change terms at any time without anyone getting upset or resentful. It can be hard to tell one person no; telling two people no, and feeling like you’re ruining a fantasy, can be harder.

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