How to Have A Sexy, Fun (Not Completely Life-Ruining And Awful) Threeway

The most important rule? Don't do it if your gut tells you not to.
Publish date:
October 1, 2014
threesomes, threeways, M

Threesomes are a blast, unless you totally screw it up.

Warning: There is a very good chance you will totally screw it up. (I know I certainly have.)

What is the main way to screw it up? Well, you do it with the wrong people. And here's the thing about threeways: You can't somehow later -- poof! -- magically undo the weirdness that has now been created if everyone is not comfortable with what's gone down. You can't undo the sight of seeing your significant other having passionate sweaty mindblowing sex with someone else or wipe out the nagging question you have gnawing at your psyche wondering if your partner is actually really more into the other woman.

I remember once considering hooking up with a man and a woman who were a "casual couple" where all seemed well and good until the girlfriend suddenly turned to me and said, "I'm not worried because I know I'll always give the best blow jobs." thank you. I had no interest in competing with this woman -- but it was pretty clear she either saw me as a threat (I wasn't; I had no interest in dating her guy) or she was being pressured into this. That's the worst possible situation in which to have a threeway, honestly.

My heavy emphasis on this level of potential threeway future regret is probably why I haven't had one in quite some time: It's just not worth it to me, and as I get older, I feel more of the impact of the psychic fallout that casual sex can sometimes bring.

But! When it's good -- man is it good.

So when a friend of mine confessed to me she was about to have her first experience as a "unicorn" (the female bestowing the grace of her presence for a couple to make the threesome complete), I told her everything I knew about this wide world of wonder. (For the record, she's been having positive experiences with 3nder so there you go, for anyone interested in trying out that app.) Now I'd like to share this important information with you:

#1: Do you know who a really great person is to have a threeway with? Someone you don't really like all that much.

Hear me out. I'm not saying to have sex with a horrible awful person, but it's probably not the best idea to risk the inevitable hurt that comes when you have spectacular sex with someone you're sort of crushing on and can't help but want something more from later on. But -- if it's impossible to imagine wanting to seriously date the guy or the girl you're having sex with to begin with, you're safe.

#2: Don't just automatically believe people when they say they aren't jealous.

Oh my god are people jealous. I'm jealous on behalf of every girlfriend or married woman watching her husband bone some other chick right now because she says she's just so cool with it. I'm not saying that it's always the woman who is going to be stressed out by the situation, it can obviously be either gender. But holy crap does it suck to be on both ends of this. I've had the girlfriend say, "I think you're too into her" about me and I've been the girlfriend saying, "I think you're too into her" about someone else.

But when there are less serious relationships at stake? This is not an issue.

To avoid a bad situation, ask questions beforehand to find out how each person really feels so as to avoid ruining an acquaintance or a friendship or a long-term commitment or a marriage later on.

Ruined relationships suck.

So do perpetually awkward vibes because of a laughably fleeting moment in time. Think ahead. Porn and masturbation and fantasy are often better substitutes than completely destroyed egos and eggshells that range anywhere from life-altering and tragic to just completely irritating and energy-sucking. But hey, if you're an adrenaline junkie and you're going to do this thing no matter what I say, just be careful and respectful of those boundaries so as to sow as little damage as possible. Which leads me to...

#3: Boundaries! Boundaries, boundaries, boundaries! They are just as essential in threeway sex as they are in regular sex.

Even if you are slurred and wasted and there's no stopping the three of you as this night is going DOWN, damn it all to hell, try to be really smart here.

This may sound like common sense but it needs to be said: Don't assume all of you can do whatever you want. Lay down what you are comfortable with and ask what the other two participants are okay with as well. You don't need to be clinical about it. Just check.

Sometimes people say, "Let's have a threeway" when what they really mean is, "Hey we're exhibitionists so we're going to bring you home to watch the two of us have sex and there might be a tiny bit of touching involved but mostly just watch us otherwise we will hate you for life."

Also, boundaries are actually pretty sexy. Your boundaries can be totally S&M if that's your game. Communication is always hot because it leads you to be more in the moment which is as sexy as it gets. I mean, don't talk non-stop. It's a balance. If you're actually comfortable with what's going on (which you better be! have you not read this article closely?) this should come fairly naturally.

One last little note about boundaries: Know what a good one is to respect? Getting the hell out of there if you're not wanted and taking cues (like when the girlfriend says after all the sex hath been wrought, "So uh do you want to stay...or can I gave you this money in my hand and you can use it to take a taxi and leave right now?"). If you do spend the night, don't assume where you can sleep and don't cuddle the person most potentially threatened by your presence. The next morning? Again, take the cues. If everyone is chill, go get breakfast. If things are weird, don't add to the weirdness. Maybe say: "I had fun and am going to take off. Do you want me to grab you guys some coffee before I go?"

Absolutely do you. As long as doing you includes all those sexy boundaries.

#4: Of course, getting loosened up by partying ahead of time is great but too much is going to kill the experience.

Not only will it lead to potentially no sex at all (please don't have sex with drunk people, whatever end of the equation you fall on here), if all goes well, you want to be able to remember it. If you have a great threeway, this is going to be one of your top spankbank memories so don't let that memory be total crap because you can barely even remember what went down. Have that water floater in between your gin and tonics.

#5: Do whatever you need to do to be safe and comfortable ahead of time.

Don't ever be embarrassed to ask what you need to in order to find out what you need to know before having sex with someone or some people. Better yet, take advantage of technology. You can even use this well-reviewed app Healthvana that shares your sexual health with a partner so you don't have to.

#6: Decided you're definitely doing this thing? Then F it all, take advantage of the fun and freedom that a threeway affords.

Here's how I explain it: You're never going to settle down and marry or have a relationship with the two other folks in the equation (of course you could, but for most people this isn't usually the plan) which is why a threeway can be such a blast. There are zero expectations, zero pretense. It's just pleasure and exploration and thrill. So often both of the parties in a two-way sexual equation are thinking about the future or the past. In a threeway, that's often not really the main factor.

As long as everyone feels good about what's happening, get lost in the flesh y'all. You'll never forget it.

Have you ever had a threesome -- or a threemany? Do you have any nightmare or amazing best-night-ever stories? Got some words of wisdom for other folks thinking about taking the plunge?

Lastly, did you know that threeways are most likely to occur in Australia? Seriously.


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