Three’s A Crowd: My Awkward, Illuminating First Threesome

“It started with a lie of omission.” Our editor gets real about the good, the bad and the ugly of her first threesome experience…

“My girlfriend’s going to love you,” he said. It was 3am on a Friday, and between the swerving cab and deserted Taipei streets blurring past us, I regretfully considered my last shot of cheap tequila. Replaying his words in my head, I realised two things: the man taking me home from the club was not single, as I had assumed, and I was en route to my first threesome.

We met a few hours earlier. He was a 20-something American basketball player based in Taiwan. I was freshly 18, some months into a Mandarin programme and sick to death of language schools’ incestuousness. Finally, a new face.

We talked about nothing for what seemed like forever, but kept engaged by observing each other beneath the strobe lights. High cheekbones, I thought as he explained a three-pointer. Nice lips. 

Eventually I couldn’t think of any more questions about basketball, and he seemed uninterested in asking me anything, so we danced. As his nearly-seven-foot body hovered over mine I briefly considered that some men were too tall, but then I took another sip of my drink, and the thought floated away. 

We moved closely but awkwardly. My 18-year-old self was preoccupied with how I looked to him, choreographing whatever I thought was “sexy” at that age while also trying to appear effortless. He mostly swayed side to side, with some interjections of holding my waist. Then he asked if I had finished my drink. I nodded, although there was still half left. “Good,” he said, downing his own. “Let’s get out of here.”

It wasn’t so much of a question as a statement, but I found myself replying “totally,” as if he asked for my opinion. So off we went, squinting as we emerged from the dark club into a fluorescently lit stairwell. 

Realising I likely looked like a wreck, I tried to subtly dab the sweat dripping off my face. No luck, we made eye contact as I wiped my upper lip. “It was mad hot in there,” he validated, sparing me the embarrassment of saying so myself. 

Then, the taxi. His words were still ringing in my mind: My girlfriend’s going to love you. Had he brought this up earlier? I racked my brain for the minutes I spent tuning out his voice, but to no avail. Even if I wasn’t really paying attention, surely I would’ve remembered him having a girlfriend. Oh well, I resolved, this will make a good story someday.

As we entered his small Taipei studio, I caught my first glimpse of his girlfriend, who lay burrowed under the covers of her bed, fast asleep. “Babe,” he said loudly, gently shaking her awake. “Babe, look what I brought you.” 

At this point, I considered excusing myself — I had never agreed to be “brought” to anyone, and her being unconscious made it even weirder. But I didn’t. Instead, I stood there dumbstruck as the woman slowly rose from the white sheets, blinking in the half-light.  She looked at her boyfriend, then at me, before breaking into a smile. “Hey,” she giggled, giving me a small wave. Then, to her boyfriend: “She’s cute.” 

I sat on the couch as the girlfriend went to freshen up, and the boyfriend joined me. A million questions flashed through my mind but, afraid they might reveal my inexperience, I stayed silent. He didn’t seem eager to communicate either; instead, we made out until his girlfriend returned and joined us. 

The next several minutes were a blur of bodies and intertwined limbs. Everything felt natural yet new, and for a moment I silently laughed at my earlier discomfort, wondering why people made such a big deal of threesomes. But then the boyfriend leaned back suggestively, and everything changed. 

Having indicated that he wanted to watch, the girlfriend and I continued on our own. This suited me fine; I was pleasantly surprised by how comfortable it was to be intimate with her, despite neither of us knowing the other existed 10 minutes earlier. It helped that I was attracted to her, but it was even more helpful how confident she was, plainly communicating what she wanted — to me, a stranger she woke up to find in her apartment.

After a long while of us ignoring him, the boyfriend invited himself back in. But the dynamic had changed. Suddenly, it was awkward. Neither of us seemed particularly interested in his participation, which felt ironic since I had come home with him. 

“Damn,” he said to me, astounded by this rejection, “you really like girls.” When neither of us responded, he retreated to the corner, switched on the TV, and began watching porn by himself.

In the moment, I felt guilty about his exclusion. But years later, I wonder how differently things would have played out if he’d approached the situation differently. Maybe if he’d communicated more openly beforehand — that he had a girlfriend, for starters, but also what their dynamic was — things would’ve felt more balanced. Maybe I would’ve never gone back to his place at all. Instead, both she and I were blindsided, with no clear direction for what the rules were.

Looking back, my taxi cab musings were correct: this three-ish-some did make a funny story at one point. Well, to me, at least. I can’t imagine what the couple’s conversations were like the morning after (I hurried out before he woke up, awkwardly refusing the girlfriend’s request to stay for breakfast). Was he upset? Was this normal? Did they laugh about it, or was there unspoken tension? I’ll never know.

For me, the aftermath was less about them and more about unpacking my own experience. I, for one, had no idea what to feel the next day, or in the days that followed. I still wonder why I went along with it in the first place. Curiosity? Wanting to feel desired? A fear of saying no? At 18, it was probably all of those things. After all, I hadn’t yet learned to ask myself what I wanted.

That night in Taipei taught me that “newness” is intoxicating, but whatever fantasy you have gets a quick reality check when it doesn’t go to plan. If I were to do the night over again, I’d ask more questions and set clearer boundaries. I wouldn’t let anyone bring me to their girlfriend like a prize to be unwrapped.

Likely because of this experience, I also have little interest in having a threesome if I were in a couple. Things got weird, but I was able to escape the next morning without discussion. I wasn’t forced to reconsider the dynamic every time I was intimate with my partner, so I never suffered from any lingering resentment. 

Because at the end of the day, sex is always give and take — the balance between each can be telling, especially when more than two are involved. These experiences are thrilling (and almost always a little awkward), but more importantly, they hold a mirror up to who we are and what we want, even when you don’t have the slightest idea what that is.

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