There was a time when sex with more than one partner at a time was considered a nasty cesSTDpool of sticky, patchouli-scented nonsense. Or something girls did with their coke dealers when they were low on cash. Regardless, group sex was not typically thought of as something that intelligent, educated, well-adjusted women of the world willingly did because, ya know, they just wanted to. Obviously, this kind of blatant, judgmental retro-sexualism is tired and sad now. I’m of the belief that we should pack up all antiquated sexual hang-ups, put them in a box with any leftover Adam Sandler DVDs we haven’t destroyed yet, leave them in 2012 for the Mayans, and head into the next Age with heads held high and vaginas unfettered by shame.
If you’re like me, one of your first steps outside the traditional sex realm — either in practice or fantasy — is threesomes! Yay! Threesomes are so magical based on the fact that they’re simultaneously in a completely different league than one-on-one sex (all those extra body parts are a real game-changer), and they’re reasonably attainable for entirely mortal, non-porn stars like you and me. Well, maybe you’re a porn star. But I’m not. And I’ve had threesomes, each of which turned out shockingly well — they were exciting, enlightening, drunk, blurry, electrifying… everything you could want from your first (and maybe only) foray into group sex. And I somehow kept my emotions, self-respect, and friendships fully intact. I know. I’m a goddamn hero among women. Allow me to drop some wisdom on you.
Be the guest star. Part of the reason I’ve found my threesome experiences to be so fulfilling, both vaginally and spiritually, is that I didn’t have that much at stake emotionally. Yes, the others involved were my pals. Yes, if things had become weird between us afterward and we were no longer friends, I would’ve been really disappointed. But I would’ve been “drifting apart from non-lifelong friends” disappointed, not “breaking up with boyfriend” disappointed. I can only imagine, since I’ve been smart / lucky enough to only be the special guest, but I assume it’s way better to be the sexy stranger, with fresh genitals and no emotional baggage, who comes in, passes out orgasms, and promptly floats out in a cool breeze that smells like freedom and inconsequence. The other two get to sit and wallow for a while in the tense, unspoken “what does this mean”-ness of the post-coital moment. Even if they’re truly that kind of liberated couple for whom seeing each other’s wet places grinding on a hot a piece of strange doesn’t tangle up their heart strings, they still have to deal with going back to the monotony of being a twosome. Not you, baby. You’re out of there and onto the next adventure, like not having to compromise on where to eat lunch. Bottom line: when there’s no one around to accuse you of “liking it a little too much,” you are free to like it as much as you want.
Don’t plan it, even if you know it’s coming (heh, “coming”). Even if the pre-threesome, ‘”this is totally gonna happen” tension has been building between you and your favorite friends for many a drunken outing now, I swear to god I will personally come punch you in the tit if you dare say it out loud. Because it will be utterly, irrevocably ruined. Premeditation is what takes a group sex experience from “wild, loving, bohemian expression of youthful willingness to indulge in an utterly beautiful, free moment of a hot, midsummer’s spiritual connection between (probably drunk) friends” to “sadness-scented craigslist ad.”
Don’t have feelings. Except for those that lead to erections and platonic bonding. Get #realtalk with me for a minute: if you have the kind of vajay that likes to slip a promise (cock) ring around every piece it lays under, or if you’re already pining in the heart for one of the slices of bread you’re about to become jelly between, just say no. You know this already, but allow me to be the friend who states the obvious: this will end badly. Scenario A) You bone them, the object of your secret affection doesn’t realize they’re in love with you at the sight of your nipples, and you’re sad. Or scenario B) You bone them, he/she does realize your genitals hold the key to their true romantic happiness, they leave their current girlfriend in a heap of tears and condom wrappers, the two of you are happy for about five minutes until the guilt slowly prods one of you closer and closer to “listen, I can’t do this anymore” and then you are still sad. And probably down two friends.
Do joke about it afterward. If you’re friends with your copulatory cohorts, and you’re all savvy and self-aware enough to have survived The Deed with your relationships intact, then absolutely feel free to talk and joke about it afterward and henceforth forever. Maybe it’s something you let others in your circle know about, or maybe you keep it your fun secret. Either way, allowing embarrassment, guilt, or awkwardness to creep in on the issue as time goes on is a dynamite way to retroactively ruin the experience. You can’t control other people’s level of weirdness, but if you stay lighthearted about it, the whole experience can be made even sweeter and sexier — a threesome can either become that “thing that happened that you don’t ever mention that silently strains your friendships until you just stop calling each other,” or a fun, fond memory the three of you share. Your call.
Condoms. Some sex laws are universally applicable, and this is one of them. I don’t mean to condescend. I know you’re smart and worldly enough to never lay bare your orifices without a latex security blanket (outside of a fully tested, vested, monogamous situation, naturally), but in disorienting flurry of surplus boobs and penises and whatnot, it can be easy to forget that this isn’t the Age of Free Love, you spritely little hippie biscuit. It’s the 90s! (I’m never going to stop saying that.) We know better. All the little soldiers in the room get helmets. 
