WWJDD: “How Do My Boyfriend And I Find Someone To Have A Threesome With?”

Editor’s Note

After multiple women accused James Deen of rape and sexual assault in November 2015, The Frisky made the immediate decision to end our affiliation with the porn star and to cancel his sex advice column with the site. In addition to believing it would be inappropriate to continue publishing sex advice from someone facing such serious allegations, The Frisky is firm in its commitment to believing and standing in solidarity with victims/survivors when they come forward. After serious consideration and input, we decided to leave the previously published columns up on The Frisky with this disclaimer, as we believe the glaring divide between Deen’s consent-focused advice and the rape allegations against him should be part of the public record. For a more thorough explanation on our decision to end this column, click here.

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Do you have any advice on initiating a threesome? My boyfriend and I are interested in adding a third into the mix but we’re not really sure how to make it happen, other than posting on a dating site or a skeevy-sounding Craigslist ad. Help!

First, it’s important to know that engaging in some sort of extracurricular sexual activity involving other people can be — but is not always — very stressful on a relationship, so definitely make sure that both you and your boyfriend are going into it as a couple. It sounds like you and your boyfriend are just looking to bang someone, so that’s what I’ll focus on – but if you were looking to engage in some sort of three-way relationship, a polyamorous thing, my advice would be way different.

As always when it comes to sex, there’s a lot more than one answer to your question, depending on who you both are, what your relationship is like and who you want to bring in as a third – specifically, a lady versus a gent, as they they should be handled very differently. There are fundamental differences between males and females — equality is great and all that, but it’s a mistake to pretend that everybody is the same and should be treated the same. People, male or female, should be given the same amount of respect, but then their differences should be embraced, so your approach to asking a man or woman to be your third should adjust to those differences.

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Let’s say you and your dude want to find another lady for both of you to fuck together. In my experience, it is usually best for the lady to break the ice, especially in IRL, as the kids say. For the most part, a lot of the people who go out at night to clubs or bars like sex and are looking to hookup. Not everyone, of course, but a lot of them. So, let’s say you’re at a bar and there’s a woman there that you both are interested in; it’s better for you, the lady in the couple, to be the one to explain the situation and ask if she wants to join in. You can be pretty blunt, honestly. After making some conversation, if you feel that chemistry, it’s okay to just say, “Hey, I find you very attractive – and so does my boyfriend. Would you be into hooking up?” She’s either going to say yes or no —and if she says no, it’s not the end of the world.

I think it’s a lot easier to find a guy who’s down to have a threesome, because dudes are basic when it comes to sex. They’re just down to have it. If you’re at a bar and you see a guy you like, go flirt with him the way you would flirt with any guy, and then say something like, “Hey, just so you know, I’m here with my boyfriend. I really want to get fucked by both of you.” The dude will probably be like, “YEAH? OKAY!” I mean, maybe he’ll be scared and run away — it’s a hit or miss type of thing – but what’s the worst that could happen? He says no? Who the fuck cares? This isn’t a long-term relationship that you’re looking for.

Now, if you’re looking to have a threesome with a guy for both you to fuck? I wouldn’t go to an American flag-covered biker bar to get your boyfriend’s dick sucked. I’d go to a bar with a rainbow flag in front of it. Or who knows, maybe there’s a dick-sucking gay biker bar out there. Actually, I’m confident there is. It’s 2015, you can probably Yelp or Google it: “Where to go in New York/Los Angeles/Kentucky/Wherever to find guys who wants to hook up with dudes and chicks?” Do a little research on the cool spots in your area and go out and meet people.

And yes, there is always the internet, where you can find plenty of people who want no strings attached sex. I can’t imagine meeting a stranger off Craigslist is going to be is going to result in the fantasy threesome anyone has ever hoped for. So fuck Craigslist – use Tinder instead! There are definitely couples who use Tinder to find thirds to hook up with – some even say so in their profile. Do that and you’ll know that anyone you match with or responds to your message is looking for what you’re looking for.

There’s also social media, like Twitter and Instagram, which allows us to meet all sorts of people we might not otherwise. Say you’re on Instagram and there’s a girl you follow that you both think is cute — send her a direct message that’s like, “Hey, I like your pictures and I think you’re really pretty — here’s a picture of me and my boyfriend and we were looking to have a threesome. Would you be interested?” She’ll respond or she won’t.

Same thing if you’re looking for a dude to fuck. Worst case scenario, the guy is like. “You’re a fucking fag and I hate you and I hope you both burn in hell!” Then you know, “Wow, that guy’s an asshole, I’m really glad we didn’t have sex with him!” and move on. It’s not that big of a deal. You might have to try that 5000 times, depending on what you’re looking for, but eventually someone will probably say “Fuck yeah, I’m down!” Just understand you need to have patience because it might take a long time to find the right person.

Once you find them, you’ll need to make it clear to them that there are going to be boundaries. Make sure that you’re comfortable with the person and that they understand that they are an accessory to your relationship and should respect that. Also, make sure that your dude understands what your boundaries are and that you understand his, if he has them.

It’s going to be awkward and weird at first, but it would be awkward and weird anytime you’re meeting someone you’re going to sleep with for the first time. A lot of it is social programming but I think it’s also human behavior. As much as sex positive people like to say it’s “just a physical activity” and you can take all the emotion out of it, at the end of the day, there needs to be some sort of interaction where chemistry can be discovered before you can have sex. Even if someone is coming over just to fuck you and your boyfriend, take a moment to get to know each other and build some sexual chemistry. You may even discover there isn’t any — you can always change your mind and say, “No, this isn’t working out.”

My last bit of advice for having a threesome is to not have expectations because it’s not going to be whatever you think it’s going to be. Don’t have a plan – it will not work out. Do not have expectations for what it’s going to be like – nothing will live up to them. Besides, super orchestrated sexual experiences are always fucking terrible. The best, in my opinion, are organic. So go with the flow.