Skip to main content
This week in Humptown we're tackling threesomes; what are they, why you might want one, and how to make it happen.
So what's a threesome? Maybe you're rolling your eyes at the question because you think it's obvious. Three people having sex, right? Not always. One of my main jobs as a sex educator is breaking down the stuff people think is obvious about sex, because it's rare that two people's "obvious" lines up, and that's where we get into a lot of our sex and relationship trouble.
Related: Humptown #1 – So You Want to Visit One of Portland's Sex Clubs, But Don't Know How? Start Here.
"Three" is in the title, so that part is easy. Three people. But sex? Not so fast. A narrow definition of sex is problematic on lots of fronts. For one, the mainstream view of sex is very heteronormative. The "penis in vagina" view of sex leaves out all the people having queer sex. Not only that, but it leaves out people who have penises that don't always behave exactly how they'd like them to, and that's most people. But learning that you don't need an erection to have sex is news to a lot of people.
So what is sex? Can making out be sex? What about mutual masturbation? Or engaging in fetish play? When you're having your first threesome, just having another person in the room can feel exciting and taboo. And sometimes that's enough. A three-way make out can be really hot all on it's own. Or maybe the third person watches the other two have sex. Or maybe you all engage in hand sex, but don't exchange any fluids.
Especially for your first threesome, or your first time with this combination of people, starting slow can be the best policy. If everyone is into it you can always schedule another time to play, but there's no taking something back if you feel funny about things the next day.
Threesomes are a common fantasy, but that doesn't mean they're for everyone. Spend some time thinking about why they're something you're interested in before you move forward. If the answer is to please a partner I suggest you put on the breaks—that rarely ends well. Threesomes are a fabulous opportunity to discover all of your insecurities, to get stuck in comparison thinking, or to experience jealousy.
It's a good idea to figure out how you're likely respond in a threesome before you involve your potential third. After all, we want to treat people like people, not sex toys (unless they're into that.) If you're planning a threesome with a partner, think about that relationship. Do you two talk openly about attraction to other people? Can you each check someone out in public without it starting a fight? If you're not sure how you'll feel being around your partner and a naked person they're attracted to, take it on a test run. Try watching porn together and talking about what and who you find hot. Can you hear that your partner thinks someone else's body is attractive? Can you hear them talk about someone's boobs/cock/ass without immediately comparing it to your own, or thinking they mean this other person is better than you?
Because Portland is blessed with an amazing selection of strip clubs, that can be another way to take a trial run. Go to a strip club together and watch your partner look at another person naked. Watch them get turned on by someone. How does that feel? Is it arousing watching them enjoy themselves? Or does it make you uncomfortable? Keep in mind that treating people like people applies to the dancers too. So if you're going to a strip club, be polite and TIP! If watching people dance is going well for you both, try getting a couple's dance. It will give an even better opportunity to see how you feel being up close and personal with a third person. (Tipping and being polite and respectful goes for private dances, too!)
If you're ready to move forward with your threesome adventure, make sure you discuss desires and boundaries with your partner first. It's harder to negotiate when you're on the spot, so come to as much of an understanding ahead of time as you can. Maybe you just want to make out, or maybe you don't want any kissing at all. Maybe you want to focus on hand sex, or oral sex. Whatever you're comfortable with, make sure you communicate that to your third early on so they're fully informed about what they're signing up for. And don't forget to ask your guest star what they're hoping to get out of the experience. Everyone's needs hold equal weight.
Speaking of which, how do you find someone to have a threesome with? You can always hop on dating sites and apps like OKCupid, Tinder, and Feeld. But those tend to have mixed results. Sometimes you get lucky, and sometimes you look like creepy unicorn hunters (regardless of your gender, or the gender you're looking for.) The reason "unicorn hunting" gets a bad rap is because of couples who approach a threesome like the third is basically a sex doll – someone with no needs of their own who is supposed to show up and fulfill a fantasy, and then go away. So don't be those people.
I've had a lot of threesomes—so many I've lost count. And only one was with a couple I met online. The vast majority of the time they're with friends. Either a friend joining me and one of my partners, or me joining a couple of my friends. And there isn't always an existing couple in the mix, sometimes everyone is a free agent. The reason this happens so often for me is that it's part of the lifestyle I've cultivated. I have friends who are open about sex and sexuality. I have a big circle of people I trust, and people I play with. But you don't need to go as deep into the scene as I am to make connections. You might be surprised to find people among your current friends who are up for it.
Like we talked about last week, you can start testing the waters with friends by hosting sexy events. From erotica reading parties, to porn watching parties, to make-out parties, these events can be baby steps to more forms of play. And if you're not up for hosting, you can also gather a group for an outing to one of Portland's many sexy events. Get a group together to see The Mystery Box Show or Whoopee! and then go out for drinks or dessert afterwards and talk about what you saw. These events can be a great conversation starter and you might be amazed what your friends share with you when you make it safe to talk about sex. And that's what it always comes down to — talking. From deciding if you're ready to have a threesome, to making it happen, to making it enjoyable. Every step of the way you need to clearly communicate your desires and your boundaries.
So is it really the more the merrier? There's one way to find out.
Have you got a burning question of your own? Email askhumptown@wweek.com and keep your eye out for an answer in an upcoming column!