I'm A Straight Guy: Here's Why I Had A Threesome With My Best Male Friend

One Sunday last year, my best friend Ian and I got on a train in NYC heading back home from a night out. I took a seat in one of the two seaters next to a cute, short, blonde, while Ian stood over us. Both Ian and I had noticed her, but we were engrossed in a conversation about our exes and didn’t pay much attention to her.

At this point, Ian and I had been friends for nearly eight years, roommates for two, and had both gotten out of relationships about six months prior — with similar women. Suffice it to say, we’d been through some shit together. As two guys who consider themselves to be nonjudgmental, openly communicating feminists, we could comfortably talk to each other about the women in our lives — in detail — without shaming or objectifying.

As Ian and I delved into what was great, not so great, what we miss and what we’ll never miss about our exes, the blonde chimed in to say how refreshing it was to hear two guys talk so openly about their emotions. She introduced herself as Emily.

She went on to say that she had gotten out of a long-term relationship just a few days before and that she had plenty of opinions on the topic of emotional openness in a relationship. She began describing some of the sexual frustrations she faced in her last relationship. She definitely had our undivided attention at this point.

Eventually, we realized we were all getting off at the same stop, but she was heading to a party. As we got off the train, Ian and I both casually suggested we catch up some time. She agreed and gave both of us her number.

Ian and I walked back to our apartment, still flummoxed that a random woman essentially just told us she’d been dissatisfied and craving great sex for months. We casually agreed to both text her, see which of us she got back to first, and thereby determine whom she was more interested in. Given that Ian and I are both considered attractive, but in very different ways, what would happen was anyone’s guess.

I’m admittedly not very patient. And a part of me was interested to find out just how frustrated Emily actually was, so I texted her first. After grabbing drinks a couple of times, she and I fell into a comfortable, primarily sexual relationship. Soon after, an old flame came back into the picture and I decided to pursue that as a monogamous relationship. I discussed this with Emily and assured her that I wanted to keep in touch, but I also subtly encouraged her to get to know Ian better. From there, Ian and Emily’s dynamic evolved into a similarly sexually-focused relationship.

Let me take a moment to clarify: This is not about two dudes “passing a girl around.” Emily had a tremendous amount of agency throughout this process. She has a formidable sexual appetite and is an extremely bright and confident woman. She knew what she wanted. Ian and I, in no way shape or form, manipulated her desire or willingness to enjoy both of us separately. This is not that kind of story.

Right as Ian and Emily were beginning to really explore their sexual boundaries, Ian decided to switch careers and coasts, moving from NYC to SF. As I was then in a monogamous relationship, it appeared that Emily would be disappearing from both Ian’s life and mine. At the same time, Ian and I had coincidentally started joking about having a threesome — testing the waters. Would we ever have done it? Would we do it now if we could? Would Emily be interested?

Over time, we wrote it off as a pipe dream.

Shortly after Ian moved, I ended my relationship and found myself back in bed with Emily. Now it was her turn to mention her long-brewing interest in having a threesome with us. I encouraged Emily to send an email to both myself and Ian, detailing exactly what she imagined doing with each of us, and why she thought a threesome was the appropriate venue for that experimentation.

In the exchange that followed, Ian and I both expressed interest and invited her to explore the details more thoroughly. She made lists of questions for both of us, things she wanted to try (some being things done to her, some things done to us, some things Ian and I would do with each other). She laid it all out. To this day, I am blown away by how much courage that took. It meant a lot to both of us that she trusted us that much.

Ian and I gave feedback on what we were comfortable with (we agreed there would be no sexual interaction with each other) and shared our excitement about the experience. I then went typical Type-A and worked on scheduling the event.

At that point, Ian and I chatted again to confirm that this was definitely something we both wanted and were comfortable with, and to reassure each other that our past and our history were too strong for any threesome to fuck up. If anything, we thought it would bring us closer — figuratively and literally.

Since Ian was in California and we were in New York, we did all of this through email exchanges, which required constant, no-bullshit communication from all parties involved.

Given Ian’s sporadic visits to New York, Emily’s involvement in several theater performances, and my new job, it took more back and forth to agree on timing than on the sex acts we’d be performing on each other. We finally chose a night and booked a hotel overlooking Central Park. If you’re going to plan a threesome, you might as well do it right.

All of a sudden, it was the day before the big day. We’d ironed out all the details. The three of us had agreed this would be a safe space for exploration. Ian and I were confident in our friendship. I had chemistry with Emily, Emily had chemistry with Ian. We all got along. There was nothing to worry about. And yet, for whatever reason, I was nervous.

To calm my nerves, I spent the day doing everything I could not to think about the night ahead. I got Viagra from a friend, bought weed and a bottle of bourbon for us to share — all attempts to make sure the evening went off without a hitch — clearly a doomed distraction from the start.

In retrospect, I recognized that my nerves were signaling how important this experience was to me. I spent so much time preaching the importance of sexual openness and exploration, the comparability of repressing your sexual identity and repressing your personality. It was time to put my sex life where my mouth was.

Around 8 p.m., I met Ian at the hotel bar, where we immediately started downing drinks and making inappropriate jokes while we waited for Emily. Emily showed up looking fantastic, but visibly nervous. She had a white wine. Soon it looked like the booze was doing the trick for Ian.

Still at the bar, he started to lightly caress Emily. She welcomed his advances. Meanwhile, I stared anxiously into space, getting more nervous by the second.

We finished our drinks and went to the room. Total silence. Looking back, I think all of us were wondering, “What now?” “How the hell do you start a threesome?” Taking charge, I did the only thing I could think of: poured everyone another drink. Then I made sure Emily know we had Viagra and weed — meaning, everything we’d need to keep the night going.

Reflecting on it now, that was a decisive moment. I was finally able to overcome the indecision and awkwardness plaguing all of us, and kick off what turned out to be an amazing night. I like to think that says something about how I’ll handle high-pressure situations in the future.

We had made a group decision early on not to use condoms. Because one of our goals was to have an overwhelming amount of great sex, we all got tested, and Emily assured us that she was on birth control. Condoms, although necessary and encouraged when other precautions haven’t been employed, contribute to a hypersexualized dynamic about as much as a bottle of bleach.

The night was a blur of ups and downs, hard-ons and not-hard-ons, wet and not wet enough, orgasms and delayed orgasms, positioning and repositioning, laughter and silence, panting and muffled moans, and everything else you can imagine. The three of us started the evening at 10 p.m. and with the exception of breaking for food (Carnegie Deli — spectacular decision), we kept at it until about 4 a.m. taking a break to sleep — or try to sleep.

We picked things back up at 8 a.m., oscillating between more sex and not sex, until about noon. At times, Emily desired only one of us and the other would watch. Other times, we’d both be involved. Ian and I blurred the line of our sexual interaction, in a way that’s very characteristic of our relationship. Primarily, by helping one another when each of us was Emily’s primary partner. We were surprised at how naturally this happened. There was no awkwardness, no hesitation. When we spoke about it later, we agreed it felt natural to help the other enjoy the experience.

We finally left the room at about 1 pm as slightly different people. Each of us had explored areas in the great wide world of sex that we didn’t know we were interested in, done things we thought we’d never do, and found more comfort with them than we thought possible.

Personally, I never looked at sex the same way again. That experience completely reaffirmed my belief that there is a lot of great sex to be had with tons of people (if that’s what you’re into), of whatever gender you like, as long as you define what you want out of any given experience and allow yourself to be comfortable with your desires.

Exiting the hotel, Emily made us promise to keep in touch with her. We reassured her we would, then headed to a bar. We talked about the night, the way we always would, laughing hysterically at intervals. The sexual energy, the ego trip associated with that kind of desire, what it’s like to watch your best friend have sex, what each of our styles was like, and what we could learn from each other. We laughed at the inevitable, hilarious moments during sex when things don’t go perfectly, the times an act glorified by mainstream porn turns out to be really hard, or just not fun. We reflected on the fact that we were really lucky to have organized the experience so seamlessly and how rare it really was to do what we just did.

What I hope people take away from this story is this: There is a way to have almost any sexual experience you want, as long as you communicate openly and honestly. You’d be surprised what people are interested in, and what aspects of yourself the world has desire for, if you are open to the possibilities.

I was lucky enough to involve my best friend in a threesome — one all parties knew would be meaningful and positive, because we had communicated honestly from the very beginning. This can be applied to almost anyone, in almost any sexual scenario.

Go out there and find someone (or someones) who wants what you want. And don’t ever bullshit anyone about what that is — especially not yourself.

For more on exploring your sexuality, start here:

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