Guide to Threesomes

Group sex is one of those things where you’re either into it or you aren’t. You might think to yourself “yeah, I’m totally into that, dude, fuckin’ A,” but you don’t really know if you’re into it or not until you take a wrong turn at some girl’s underwear party and there’s a full blown orgy in development in somebody’s bedroom, and they’re gesturing for you to come and join in.

You’re either into it or you aren’t, and there’s certainly no shame in not being into it. It’s pretty spooky. I flinched. I was on the precipice of an orgy and I flinched. No biggie.

Threesomes, though, are a little different. Almost every straight dude in the world has at least considered being with two women at the same time. I don’t know what women think about being with two dudes or a dude and a girl or whatever, and nobody ever will because that’s one of their mysterious secrets that they can’t ever reveal because it’s not one thing. But I know about the two women at once thing. Every dude wants that, at least somewhere in their heart of penises.

So let’s say when I’m talking about threesomes, I mean “two girls and a dude,” because that’s a more common straight dude thought than “I would not find it at all uncomfortable to be in a situation where I might accidentally touch penises with another dude while pleasuring a beautiful woman.”

That’s in the realm of group sex that you’re either into or not and you don’t know until it happens and you want to jump out of your own skin and then burn it.

Anyway, yeah. Threesomes.

1. Whoa, guy.

Threesomes have to be the single most overrated thing in the entire universe. The entire universe. Threesomes are more overrated than, I don’t know, gravity or something. That’s how universally overrated threesomes are.

I’m saying this not because it’s totally true, but because it’s a helpful way to think. Threesomes are a tricky thing to rig. Either you do it the right way with your wonderful girlfriend who’s also curious about it and there are all these preliminary meetings and discussions about “emotional boundaries” and “safe words” and all kinds of unfun unsexy bullshit like that that you have to go through to have any reasonable shot at an enjoyable threesome, or you can do it the wrong way by going home with a couple of trashy drunks whose breath smells like corn. Either way, regardless of how much fun the threesome is, it’s going to involve you doing things that you’re not totally sure you want to do.

Let’s face it, you’re not Kanye West. You don’t get to have threesomes with two ridiculously hot supermodels who you just met and it all happens on a whim just because it’s Tuesday and maybe this time it won’t be boring like it was the last time three days ago. You’re going to have to make a few compromises to get there.

So it’s important to think to yourself that “threesomes are overrated” because that way you won’t get so excited about having a threesome that you make a compromise you don’t want to make. I’ve made those compromises. They’re the kind that make you wonder who you are after you wake up and your head feels like it collapsed and you’re naked and wearing clown makeup and you’re too ashamed to look at yourself in the mirror until you call an exorcist or something. That’s the sort of compromise that guys end up making when they get overzealous about having a threesome. So watch yourself.

Remember, they’re overrated. You don’t have to have a threesome before you die. That’s a lie. They’re overrated.

2. The setup.

So as I hinted about before, there are two ways to do this. Technically they’re the right way and the wrong way, but there’s a right and a wrong way to do both of them. That sounds complicated, and it is. Unnecessarily complicated. So there are four ways, if you’re keeping score. Shutup about it or I’ll turn it into nine.

Here are the four ways you can set up a threesome:

The Right Right Way.

You have a girlfriend who’s so cool you can’t believe it, and the only thing stopping you from marrying her is the fact that you don’t have a solid career or even, technically, a job. Maybe you just really like her a lot, I don’t know. All of this is a pretty fucking big “if” at any costs, because it involves having a girlfriend who is super into the idea of having a threesome with you and a friend of hers. Like it’s almost as much her idea as it is yours, and you’re both really into it and her friend is really into it too, and you’ve talked about it a little, like assurances are made that this won’t turn into a nightmare love triangle thing and you’re going to be adult about it, but the conversation was more of a formality because that’s how you both actually feel anyway. But that’s The Right Right Way to do it, when you’re already in a relationship of two people and you both really want to try it with somebody you can trust who wants to do it with you guys.

But of course this is like saying that the right right way to get rich is finding a briefcase full of money in your pantry.

The Wrong Right Way.

You have a girlfriend who you don’t really like a lot but you’re in the relationship because she’s the type of person who’d do a threesome just to keep you in her crazy hotsex clutches. Technically, you might as well do the threesome with her, because that’s what your priority levels are set at and you might as well go all the way with it, but just know you’re headed for a nuclear explosion of a breakup, and there’s a solid chance that the entire next year of your life is going to be horrible if you get involved with a woman like this. Not worth it.

Or you have a girlfriend who’s really awesome but who isn’t too into the idea of a threesome but you’re going to convince her to do it by, I don’t know, taking ballroom dancing classes or doing something else she wants you to do but you don’t want to do. First of all, you should just do the ballroom classes anyway, because they’re probably going to be more fun than you think and your girlfriend will have a good time. Second, if she’s not into the idea of a threesome, it’s not going to be a fun threesome. And a threesome is sex, remember, and sex is a bummer when people aren’t into it. In fact, it’s maybe the biggest bummer of all time.

So when it’s sexy what’s your fantasy talk time, just say, “I’d like a threesome, but no biggie, I’d also like to own a football team. I’ll settle for a blowjob.” Then maybe that way there’s a little idea of a threesome in the back of her head (right here I’m going to avoid a terrible joke which references the previous sentence) that she can’t shake and maybe she’ll get excited about it and you can do things the Right Right Way. But you don’t want to be pushy. If that little threesome bird never comes back to your window, then you have to let it go. It’s out there, flying free. No “please please pleases” or promises to do the dishes every night forever. Be a man. It’s over.

The Right Wrong Way.

This is the version of threesome where “it just happened.” Like you were hanging out with some people and you got drunk and then crazily there was like a near-threesome situation happening, and then you were like “fuck it, let’s do this,” and you had a threesome.

The problem with it is there’s almost no way to predict or control the situation. It just happens, so how do you set it up? Well, you don’t. You can’t. All you can do is be vigilant for the opportunity.

You have probably been involved in social situations which could have turned into threesomes and not known it. Just put that thought into your head, and the next time you find yourself in an extended conversation with two people over drinks, allow yourself to think “could this ever conceivably turn into a threesome, and if so would I be even mildly interested in that?”

It’s a fun game to play. Thoughts are free. You’re allowed to have as many of them as you want, even if that means talking to somebody about tort reform while imagining a threesome with them and their Dad. Nobody has to know you thought about it, and don’t worry, it doesn’t make you a bad person. It makes you a funny person.

Plus, if you’re in a situation where you think to yourself, “Yes, this could be a threesome, and yes, I want in,” you can act accordingly, which just means being equally friendly to both parties. That’s a nice way to be anyway. Nobody likes to feel left out. They don’t have to know you’re thinking “threesome threesome threesome.”

Then you just continue to flirt openly with both parties and gauge whether or not they mind, and if they don’t you get more aggressive and see if they mind, and so on until a threesome either “just happens” or doesn’t. But you never want to be like a drill sergeant about it, like “threesome at 0300 hours.” In fact, you never want to say the word “threesome.” You just go with the flow, and if the flow towards Threesomeville gets cut off, you’re cool with it. No biggie. You enjoyed the conversation.

Oh yeah: you should make sure you actually enjoy the conversation, otherwise you’re going to end up doing things The Wrong Wrong Way.

The Wrong Wrong Way.

This is where you meet two skanks at a bar and you’re lonely and bored and depressed and you think one of them is medium hot, like let’s say a 7, but she’s got a grating uptalky voice where everything sounds like a question, and the other one is slightly smarter but she’s got a really weak chin and she’s overweight in an uncute way, and these two for whatever reason have their entire sense of self staked on the notion that they’re “two crazy bitches,” as if that’s a good thing.

You see where this is going, right? You didn’t leave the house that morning expecting to have a threesome, and all of a sudden here’s one staring at you in the face, and it’s being about as subtle as the showgirl’s makeup it’s wearing on its eyes.

I’m not here to judge. Maybe you go for it. I’ve done worse things in my life. I just know that this is the type of threesome scenario that is A. more common than the Right Wrong Way or the Right Right Way, and B. the reason why “threesomes are overrated.” The smart play is to not hang out with people who you’re only hanging out with because of the possibility of a threesome. That’s not a great “only redeeming quality” to have. You’re better than that. But of course you have your penis to consider too. And you’re the only one who knows whether or not your penis is better than that.

3. Logistics.

Technically speaking, a threesome only really works if all three people are attracted to each other to the point where they’d go at it with just the two of them.

Otherwise it’d be a situation where two people are so attracted to one person that they don’t care what happens so long as they get to be there fucking that person. And you’re not going to be involved in one of those ever because you don’t have spooky Bill Clinton presidential sex charisma. I shook his hand once and I might have had sex with him. I don’t know. He was so charismatic I blacked out. I’m not even lying. It was like a crazy voodoo trick from the movies where the hero suddenly realizes he’s been drugged. Anyway, that’s not you.

So you’re looking to create a threesome situation where everybody wants to fuck everybody. Think of it as one thing. Instead of doing twice the “work,” (I hate to call it “work” when I’m talking about sex, because it’s not work, but let’s face it, sometimes it’s work, like it tires you out because you’re working really hard at fucking somebody) think of yourself of doing one third of the “work” of this whole event. It’s not about you. It’s about the three of you doing this together. Otherwise it’s going to get super boring the second you blow your load.

Yeah. That’s what I was getting at.

Real life threesomes have nothing whatsoever to do with porn threesomes, where two fake-titted weirdos bounce up and down on a roid rage boner and then it spews all over them and everybody’s happy, like “taadaa!” No. In a real life threesome your orgasm is just a minor landmark on the roadside. Or at least it should be if everybody’s enjoying themselves. Remember that women aren’t as goal-oriented as dudes. They do things like eat meals slowly in order to savor the experience, even when they’re really hungry. It doesn’t really make sense until you see it in action in a threesome.

That’s just how women are made. They’re totally insatiable because they enjoy everything too much.

So you have to keep doing something to continue the festivities even if you’ve just blown a load. Sorry, but them’s the rules. Otherwise you’re being selfish and making the whole thing about you. Actually, that’s a good idea even if we’re not talking about threesomes. But we are. Remember, even though you’ve totally had a big porno-style orgasm, there are still two people who are also having sex with each other, and if you can help them with that, you should. Otherwise they’ll forget you’re even there because they’re women and women are insatiable. You don’t want that. You want them to be as excited as you are when you’re ready to go again.

If that seems exhausting to you, great, you get points for being perceptive. It should be a crazy exhausting all nighter. Man up. You only get so many chances at this sort of thing.

As for the general tone of the proceedings, you want to go with a fun slumber party vibe for the initial stuff, like the removal of clothes and the making out and stuff. Then when stuff gets more serious, like when something’s happening that feels really really good to any one person, there will be a certain “we’re really serious about this?” hush, which you want to treat delicately. Don’t break that silence. Here’s one of those classic dude saying the wrong thing at the wrong time blunder opportunities. You’ve got a real chance to be about as sexy as the guy in the bow tie at the salad bar who really wants to talk in depth about the weather if you say the wrong thing during this silence. Just keep your mouth shut and be a cool customer. Quiet confidence.

Then when it’s clear that things are getting really really serious, like you’re next in line for an orgasm and you’ve got everybody’s attention, that’s when you’re allowed to start talking a little. Then once everybody’s had an orgasm you can go back to slumber party mode and things will be a little more relaxed.

But you’ve got to be careful in that initial sacred “we’re really doing this” moment. Think of yourself as a plaything, like the angel from Barbarella, or that Bjork song “Venus As a Boy” or, really, just think of Bjork. “Bjork Bjork Bjork. I really like Bjork’s music.” That’s the kind of dude you want to be in the initial proceedings. Then you can get a little more ballsy later once you’ve earned it.

Of course all of this is theoretical, right?

I mean, you’ve never had a threesome. If you have, you don’t really need this. You’re already living it.