A Guide to Having a Threesome for the Cripplingly Anxious

About five seconds into my first threesome, I confirmed what I'd already suspected: I wasn't ready.

To be fair to my partner at the time, Jesse (not his real name), he and I had been all about having a threesome in the weeks leading up to the event. For his part, Jesse didn't need much persuading. A Midwestern-raised, problem-solving digital marketing entrepreneur in his mid-30s, Jesse had registered us on several apps, it seemed, before I'd even gotten to the "à trois" part of ménage à trois. By the time I noticed inklings of uneasiness bubbling up over the prospect of my steamy fantasy being transformed into grating reality, Jesse had found us a third.

The third, let's call her Mirabel, was pretty and sweet. Having spent a few hours of awkward conversation with her and Jesse at a fancy wine bar at the start of the night, I started chugging fancy wine to overcome my increasingly apparent—to me, anyway—anxiety over what I'd gotten myself into.

But to try to stop what I'd set in motion right at the eleventh hour—and after Jesse had gone through the trouble of finding a third and buying us wine and ordering an Uber—seemed capricious and ungrateful. Besides, I reasoned, trying to bludgeon my reluctance as we sped toward the hotel, how would I know I wouldn't like it unless I tried it?

Fast-forward to the next morning, after we'd Ubered Mirabel home and it was just Jesse and me left in the hotel room. Seething with a red wine hangover in the unflattering light of morning, I felt mad at Jesse somehow, as if he'd been the one who coerced me into doing something I hadn't wanted. As if he should have sensed my hesitation. As if he should have read my mind and known I wasn't ready, despite my words and actions to the contrary.

"What did you think?" he offered, smiling uncertainly. Like a sullen, immature person who clearly wasn't ready for a threesome, I gave a cold, noncommital answer and was moody for the rest of the week.

Reflecting on the experience, it's unreasonable to expect I, an introverted, anxious then-kinky-sex virgin, would've nailed this highly intense, multiplayer, taboo sexual experience on the first (or second or third) try. Reasoning that practice makes perfect, I decided to give threesomes another go, but this time, I reached out to experts for guidance.

The case for threesomes

My persistent curiosity over threesomes is totally normal, which is to say, statistically common, according to Justin Lehmiller, Ph.D., a Kinsey Institute research fellow and host of the "Sex and Psychology Podcast" in Indiana. Lehmiller discovered in his research that 95 percent of men and 87 percent of women fantasize about multipartner sex, making it the most common sexual fantasy of U.S.-based adults.

"Part of the appeal for many is simply the novelty of an additional person during sex and all of the new sexual possibilities it opens up," Lehmiller said. "Threesomes can also be about exploring your sexuality, such as exploring bisexual or pansexual attractions or simply experimenting with different activities, or even seeing your partner in a different light, such as when a heterosexual man is aroused by the idea of his female partner being with another woman."

Celeste Hirschman, M.A., a sex coach and the founder of Somatica Institute in San Francisco, assured me that having a threesome, while clearly not without its potential pitfalls, can actually do a lot of good for your relationship.

"It can be a super-fun adventure if both of you are into it and can heat up your sex life," she said. "You might fantasize about it together for years to come and you might feel more desire for your partner afterward. If done well, it can build trust and connection."

How to have a successful threesome in a non-awkward way

Make sure you're ready—like, really ready.

"Having a threesome should only happen if you and your partner are in a really solid place," said Gigi Engle, a certified sex coach and sex educator, and author of the book "All the F*cking Mistakes: A Guide to Sex, Love and Life" who splits her time between Chicago and London. "It should never be something that you do just to please someone else or to save the relationship."

"A threesome is not a good way to try to solve a problem," agreed Stella Harris, Oregon-based certified intimacy educator and coach, and author of "The Ultimate Guide to Threesomes." "If you're fighting or unhappy, all of that energy will be brought into the threesome with you. Not only will it be no fun for you, but that's a terrible situation to bring a third into."

Bring it up the right way

Introducing the idea of a threesome as a sexual fantasy is a reliable way to test the waters. Engle suggested talking about a fantasy you've had or watching ethically made porn.

"Starting [with a fantasy] can give you a sense of where both partners are in their headspace with the idea," Engle said. "From there, you can start talking about what your ideal threesome would look like, your feelings about it happening in real life, and start strategizing together as a couple."

What if your partner isn't on board?

"If you get the sense that your partner is not that into it, you can talk about what the issue is that's making them not want to do it," Engle said. "But bottom line is that if your partner isn't totally into trying it, you shouldn't do this—you're not ready."

Plan meticulously

Engle stressed the importance of meticulous planning of a threesome, particularly if it's your first time.

"I think some people think it should be this super-spontaneous thing, but if you've never had a threesome before, it's a very risky thing to do," Engle said.

She stressed the importance of establishing clear boundaries, especially for people who feel a bit tense or awkward about the situation. Decide in advance, for example, whether kissing on the mouth is acceptable, if it's OK for your partner to penetrate the other person or for you to be penetrated or penetrate someone else.

Check in often

Before, during and after the threesome, Engle recommended checking in often to make sure everyone is still comfortable and enjoying themselves. To make sure everyone's needs and emotional well-being are being cared for, Engle suggested relying on a "traffic light" system of safe words where red means stop, green means go and yellow means, "I'm starting to feel uncomfortable with this."

"Take breaks," Harris advised. "Let everyone catch their breath, use the bathroom or get some water.

"Be flexible," she added. "Bodies are unpredictable and so are emotions. Don't be so committed to one plan or fantasy that you can't change things up in the moment based on what everyone is game for and capable of."