Threesomes: Let My Experience Be Your Guide

Pros and cons to consider before you take the triple plunge

Published: September 19, 2022 | Last Updated: July 14, 2023

At 30, I’ve had a lot of threesomes. I’ve identified as polyamorous my entire life, since I started dating at 15, though I wasn’t sexually active until age 21. You’d be surprised how many threesomes you can fit into nine years — OK, closer to seven, since the pandemic dried me up, but after getting married at Ferndale Pride in 2019, that hasn’t bothered me too much.

I’ve had threesomes with strangers, with friends and within established polycules. In my 20s, I was down to fall into bed with almost any attractive, willing duo. There’s endless fun to be had with multiple sex partners — new positions, new bodies, new kinks.

Threesomes are great, and I’m pleased to have had so many of them, but I’m only one person. Everyone involved has to assess their emotional and physical safety — ideally before clothes come off.

Let’s talk about the good first.

Pros of having a threesome…

There are things I never thought I’d be into until I got a chance to try them with more experienced partners. Fisting was one of those things. I was never interested in fisting until a friend and I took a girl home from Gigi’s and it turned out both of them had done it before. We were going at it a bit rough, so watching a very dominant woman push her whole hand inside my friend was an unexpected turn-on. After that, I got to try it myself, and as weird as it is to have your whole hand enveloped by someone else’s body, seeing how much my friend loved it makes that weekend one of my most impressive encounters.
One of my favorite parts of having a threesome is getting a personal show. I find sex fascinating, but my fickle sex drive sometimes means I need a break. Fortunately I’m really into watching, so during a threesome I can take a sec to admire my partners, maybe drink some water. Otherwise, randomly stopping and starting feels kind of weird. Imagine withdrawing from a single sexual partner to stare at your phone for a few minutes until you’re in the mood again. Major no!
Threesomes majorly appeal to people yearning for sexual freedom. Sexual adventure within a stifling couple-based monogamous society is highly valued, especially when that involves escaping homophobia and transphobia. It’s thrilling to step outside the lines! I was raised super Christian, ingrained with a severe fear of “sexual sin.” Not fun. My first threesome was a lot emotionally, but after being stifled for so long I finally felt in control of my desire and choices.
Sexual experimentation can help you figure out your identity — it did for me. I identified as a lesbian for a decade, but during that time I did have threesomes involving masc-of-center people and, yeah, a few men. I was confused about my willingness to participate in those, even while being careful to establish physical boundaries. Eventually it stopped feeling like a fluke and I was able to accept myself as a transmasculine person who is definitely attracted to men.

Though this is a major bummer, group sex doesn’t always live up to the fantasy.

Cons I’ve experienced…

Jealousy is the big one. This is most common within relationships. I had a threesome with my wife and one of her partners. It was fun for the most part, but a few times I became insecure and grumpy because I felt left out. We communicated through it, but I did slink off to the other hotel bed to sulk for a while. Not my best moment.
Since threesomes often have a queer element, identity plays a huge part in establishing comfort during group sex. Above, I discussed how threesomes with people of different genders can help you find the perfect label, but on the path toward that, I felt a lot of guilt. I was still “in the closet” as a lesbian and hadn’t yet come out as my authentic self. I thought I was betraying lesbians by letting men touch me instead of us both focusing on the woman in the equation. Once I came out as a masc4masc guy, I made some impulsive decisions involving Grindr because I wanted to confirm my sexual discoveries. I can’t say I recommend the way I went about things.
After a passionate one-night stand, few things are worse than post-bang awkwardness. So it felt great in the moment, but fucking my roommates immediately after moving in wasn’t a great decision. In that instance I hooked up with both of them separately, but a few years before that I had a threesome with my partner at the time and a guy I was in a theatrical performance with. He got to make out with another cast member on-stage, and I was majorly envious. If you’re gonna see one or both people the day after smashing, put some careful thought into it.

On that note… If you’re still with me on the “yes!” train, before you agree to a threesome, you should ask yourself a few questions.

Can I stand to see someone else touching my partner? Because jealousy isn’t fun for anyone involved.
Will this affect our friendship? Because some people can’t help feeling awkward after giving a casual friend a rim job.
Does my desire to do this go against my instincts when it comes to single-partner hookups? Because an hour of indulging sexual curiosity is not worth feeling like you’ve betrayed yourself.
Is this situation empowering? Because empowerment lies in your ability to say "yes" and your ability to say "no."

If the answer to any of the above skews negative, you might want to decline. There’s nothing to be gained from forcing yourself into a situation to avoid disappointing someone(s). Consent and communication should always be mandatory, but especially here.

Between health issues, energy levels, and how difficult it is to meet people when you aren’t outside much, I’m not sure how active I’ll be sexually or if/when I’ll have a threesome again. However, I’d like to participate in an orgy before I die. Maybe that chance won’t come until I’m 70 and playing strip-bingo in a nursing home, but when it does, I’m gonna take it and hold on with both wrinkly hands.

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