One Woman's Long, Incredibly Complicated Quest to Have a Threesome

With my thirty-sixth birthday fast approaching, I have no problem admitting that I don't own property, have never been married, and haven't birthed a child. While the absence of these life events has the potential to deprive some people of sleep, keeping them tossing and turning at night wondering where they went wrong, I'm fine with all of it. What truly floods me with regret and despair has nothing to do with love or kids, it's the fact that I've made it this far in life without ever having experienced a threesome.

While being the filling in a penis sandwich and/or engaging in the type of spontaneous, steamy FFM threesome you've seen in the Wild Things trilogy has been in the forefront of my fantasy highlight reel for as long as I've been legal, I have yet to have one firsthand. And that's not for lack of trying.

When I'm seeing someone, they are generally—and mindbogglingly—not down for it. If they are, we have a tricky time finding a third. Rarely have I met a guy who shares the same threesome fantasy ideal—either me and two guys, who aren't making out with or into each other (we'll get to that) and are completely mindful of my comfort level, or me and a guy in a dominant role, with a hot, younger, subbing third we stumble across during a freshman week rally.

While the vast majority of couples I know don't register to me as potential sexual playmates, occasionally I'll meet a pair who has a free-spirited and open sexual candor that I envy and want to get in on. The guy is always down. The lady, not so much. When one friend asked if I wanted to join her and her boyfriend—whom I'd never met—some time, I told her I was game, but mostly because it felt imprudent to say otherwise. When she texted me a few days later, asking if I wanted to meet them at a hotel, I declined. The whole thing felt too professional, in the showing up and getting down to business, sight unseen kind of way—and not in a way that has the potential to turn me on. A similar incident happened a few years earlier, with a fella I was casually sleeping with when I'd swing through Los Angeles. I was in town on his birthday, and he had planned to meet me at my hotel. Before arriving, he texted to see if I'd be down with another lady joining us—it was his birthday, after all. When I told him it depended on whether or not I was attracted to her, he texted back: "She said the exact same thing." She never showed up. Another time, I was set to meet up with a fresh-faced pair of skater cuties I'd met on Tinder who were in town from Montreal. The night we were meant to meet up for a drink to see if the chemistry was there, they (well, the guy) told me their car broke down in Brantford, Ontario, and they weren't going to make it.

To help resolve my feelings of perturbation and non-fulfillment in my lack of experience, I reached out to several experts on the subject, to see how I could better confront my obstacles.

The science of threesomes is sparse, at best. A few studies have been conducted over the years: in 2004, ABC News found that 14 percent of adults (and twice as many single men) have had sex in a threesome, while a 2010 Cosmo survey (hey, I said there were few studies) showed that less than ten percent of women had had one.

So apparently, I'm not alone.

The fact that I'm excluding a slice of people—bisexual men—from my fantasy is not unique among women. Heather Armstrong, an associate researcher at the University of Ottawa, conducted a study looking at attitudes toward bisexual partners. What she found wasn't that surprising: women have more negative attitudes about having a bisexual male partner than men did about female partners. That is to say, a lot of men are totally game with hooking up with two ladies, while women aren't as open to having a threeway with two guys who are equally into both partners. (The study examined opposite sex relationships, and not same-sex partnerships.)

"The vast majority of the men were interested in participating in a threesome, especially if it was a casual sex relationship…whereas the women were much less interested in having that opportunity," she told VICE. "In general, women tend to want to have threesome more with women than with another guy."

Armstrong suspects that is a result of the widely held stereotype that bisexual men are actually gay men who are reluctant to admit it, while there's a greater cultural acceptance of bisexuality among women.

"So if she is bisexual, then the idea is she's straight and just fooling around with her girlfriends, so it's not a threat to a male partner," she says.

My reluctance to engage with bi or gay men in a threesome has nothing to do with me feeling threatened. While I identify as 12.8 percent not heterosexual, I'm simply not aroused by the idea of two guys making out. I'd prefer to have the attention focused entirely on me. But where am I going to find two straight men who are OK being naked together and turned on with the idea of sharing a woman?

My smartphone, that's where. 3nder (pronounced "thrinder") is an app that's basically Tinder, but with the intention of pairing couples with thirds and vice versa. I had great hope, so I created a profile, customizing my preferences to find a pair of men who were into a devil's threeway. Unfortunately, there were only three sets in my area, all of whom appeared too fey—and perhaps didn't understand the settings on the app—for my tastes.

I reached out to the app's creator, Dimo Trifonov. The London-based Bulgarian designer started the app after he and his girlfriend had trouble finding a third for some experimenting. They didn't relate to the clubbing lifestyle or swingers bars and were creeped out by polyamorous dating websites. So he designed 3nder as a way to branch out.

He says the demographic is 75 percent straight men, as well as couples and bi-curious girls who range in age from 18-26. Trifonov suspects that it draws a younger demographic who feel they don't have much to lose, while people with more conservative lifestyles might be nervous about the mandatory Facebook login.

Ironically, despite committing his life to an app that facilitates threesomes for people, Trifonov still hasn't had one.

"We were curious at some point but it wore off," he says. "We keep an open mind but this app is so deep into my life and opened up my mind to experiences, so that's cool too."

Reid Mihalko is a sex and relationship expert based in Oakland, California. While he regularly speaks at colleges and hosts seminars like "How to be a Gentleman and Still Get Laid," and "Navigate Successful Threesomes," he didn't come at his experience through scholarly studies. Basically, he learned how to teach threesomes by having lots and lots of them—more than 150, though he can't place an exact number. When we spoke, he gave off the same open and affable vibes as a seasoned Burning Man attendee. It's also worth noting that in 2004, he founded New York City's Cuddle Party. Mihalko is full of tips and strategies to get things underway in consensual, comfortable circumstances.

His bottom line is that if you want to participate in a threesome, you need to feel emotionally and physically safe. If you're in a relationship, talk openly about what you'd like from the experience with your partner. If you're single, talk about who you'd like to engage with—strangers, friends, a couple—and be clear about how often you've all been tested. Mihalko says it's optimal for threesome virgins to have their first experience with someone who is old hat to such activity.

Once everything has been established and the three-way is close to going down, Mihalko suggests the best time to get things rolling is when it feels most awkward.

"Take a breath and say 'I have an idea,' and then you ask for something you'd like them to do for you," he says, adding that three-way kisses are great. "Instead of something you'd like to do to them, because some people get anxious receiving."

Most three-way newbies refer to porn for the base of their foundation, which MIhalko says is potentially disastrous.

"They don't think it's three people in a shower making out and soaping each other up," he says. "People get nervous of having it go from 0 to 100 in a heartbeat. When you can suggest things that you count as a threesome, it gives people more choice and options initiating and getting the threesome started."

Having dug deeper into threesomes in ways that didn't involve watching porn has helped reassure me that it's probably best I didn't make it happen when I wasn't entirely feeling it. My future game plan is to meet the right fellow, and make it a joint effort. That way, my intentions on having a threesome will feel more like teamwork than a solitary quest. But for now, I will channel the patience of a Buddha and re-watch Larry Clark's Ken Park as fodder for creative visualization.

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