So You Wanna Try a Threesome?
Photo by Fusco Studio on Unsplash
Okay lah, so you’ve been thinking about having a threesome. Maybe it’s been in your fantasies for a while, or maybe your partner brought it up during pillow talk and now you’re both like, “Eh... can try or not?”
Whether you’re here for the excitement, the novelty, or just to tick something off your bucket list before turning 40 (midlife crisis, anyone?), here’s a thoughtful, cheeky guide to help you make your first threesome a spicy but safe success.
1. Choose Your Third (Very) Carefully
Finding the right person for your threesome is like choosing someone to go on a three-legged race with—except with less running and way more skin contact. The chemistry, communication, and trust between all three of you need to be spot on. There are generally three types of "thirds" people consider: strangers, acquaintances, or friends.
If you’re bringing in a stranger, this can add a level of excitement because there’s no pre-existing emotional baggage. But that also means you have to be extra cautious. Always meet up in a neutral, public space first. Feel them out (not literally—not yet, anyway). Do they seem respectful? Do they understand boundaries? Are they the kind who texts back in full sentences and doesn’t call everyone “babe” within five minutes? Green flags.
If you’re considering a friend, know that it might change your dynamic forever. No matter how mature everyone is, sex changes things. If you’re not willing to risk the friendship (or the occasional awkward dinner party), think twice. Also, don’t assume someone’s into the idea just because they once laughed at your dirty joke—you’ll need honest conversations.
Some couples also choose to go the online route. There are apps and websites that cater to ethically non-monogamous or kink-friendly folks. Just be honest in your profiles. You want someone who knows what they’re getting into—and out of.
Bottom line: you’re looking for someone who respects your relationship, understands consent, and won’t make things weird afterwards (unless you’re all into that).
2. Communication: Sexy in Theory, Essential in Practice
A lot of people think a threesome is all about action and acrobatics. In reality, the most important part happens before anyone gets naked: the conversation. You’ll need to talk openly and honestly with everyone involved about boundaries, expectations, and safety.
If you're in a couple, start by talking with your partner before you bring anyone else into the mix. What are your motivations? Is this about fulfilling a fantasy, exploring bisexuality, or adding excitement to your routine? Being clear on the "why" can prevent miscommunications later.
Next, discuss ground rules. Some people are okay with full-on everything, others prefer specific boundaries like no kissing or only touching in certain ways. You might think it’ll be a mood killer to talk about this, but trust us—there’s nothing sexier than consent and clarity.
Don’t forget to talk to your third person too. They’re not just a prop in your fantasy. Ask about their boundaries, turn-ons, and dealbreakers. Create a space where everyone feels empowered to speak up and say no if something doesn’t feel right.
And always, always establish a safe word. It might sound dramatic, but when you’re in the heat of the moment, you need a clear, non-sexy way to signal discomfort. It could be something as silly as "pineapple" or as local as "laksa."
3. Set the Scene (And Make Sure Got Aircon, Please)
Singapore is hot and humid. The last thing you want during a passionate night is for someone to tap out because of heat stroke. Whether you’re setting this up at home or in a hotel, the environment makes a huge difference.
If you're doing this at home, make sure your space is clean and comfortable. No one wants to get frisky next to a pile of unfolded laundry or last night's bak kut teh leftovers. Declutter, change the sheets, and maybe light a few candles—but not so many that it feels like a séance. Soft lighting can help everyone feel more relaxed (and let's be honest, a little forgiving when it comes to body insecurities).
Music helps too. Curate a playlist that’s sexy but not cheesy. Avoid anything with lyrics that remind you of your secondary school breakup or your mum’s karaoke playlist.
Hotels are a good option for privacy and neutrality, especially if you’re inviting someone new. Look for adult-friendly spots that offer privacy and decent soundproofing. Pro tip: boutique hotels around Bugis or Chinatown often strike a good balance between cozy and discreet.
And finally, prep the essentials: condoms, lube, towels, water, tissues, and maybe even a snack or two. Because nothing kills the mood like having to pause the action to hunt for that one half-used tube of lube you think you saw last CNY.
4. Safety First (And Second. And Always.)
Let’s not sugarcoat it: threesomes, like any form of sex, carry risks. But with a little preparation and care, you can focus more on the fun and less on the fallout. Start with protection. If you’re having sex with multiple partners in the same session, use a new condom every time you switch partners. Yes, even if it seems like a hassle. Think of it like chopsticks at a yong tau foo stall: you wouldn’t want someone else’s spoon in your bowl, right?
Lube is your best friend. More people often means more friction, and that can lead to discomfort (or worse) without proper lubrication. Choose a high-quality water-based or silicone lube, and make sure there’s enough to go around.
Before the encounter, have an honest conversation about STI statuses and sexual health. It may feel awkward at first, but it’s a sign of maturity and respect. If someone reacts defensively, that’s a red flag.
And don’t forget hygiene. Fresh towels, clean hands, and easy access to a bathroom are small things that make a big difference. If you’re using toys, clean them thoroughly before and after.
Last but not least, look out for each other. Check in throughout the experience. A quick "Everything okay?" goes a long way in making everyone feel safe, seen, and respected.
5. Debrief Like Grown-Ups (No Ghosting Allowed)
You did the thing! Maybe it was hot. Maybe it was a little clumsy. Maybe someone got a cramp halfway and now you can’t look at yoga poses the same way. No matter how it went, what happens after the threesome is just as important as the act itself.
First things first: check in with everyone involved. Not just physically, but emotionally. Did anyone feel left out? Did something unexpected come up? Was there a moment that felt awkward or uncomfortable?
If you're in a couple, have a separate debrief with just the two of you. Be honest about what worked and what didn’t. This isn’t the time for ego—it’s about growing together and understanding how the experience affected your relationship.
With your third, send a simple thank-you message or have a casual follow-up conversation. Ghosting someone after such an intimate experience is not only rude, it's damaging. Treat your third with kindness and respect, even if you don’t plan to meet again.
Use this time to talk about what you’d do differently next time (if there is a next time), what you loved, and what you’d skip. Maybe you discovered something new you want to explore more deeply, or maybe you realized three’s a crowd and two is your happy number. Most of all, don’t forget to laugh. Sex is messy, funny, and gloriously human. The more you can embrace the awkward along with the awesome, the better you’ll navigate these wild, wonderful experiences together.
Final Thoughts: You Do You
A threesome isn’t just about fulfilling a fantasy. It’s about mutual trust, open communication, and being okay with things not going exactly as planned. Sometimes, it’s fireworks. Sometimes, it’s two minutes of action and an awkward Uber ride. But if everyone involved feels respected, safe, and seen — that’s a win.
And don’t forget to have snacks after. You’ll thank yourself. Nothing bonds people like shared vulnerability... and McNuggets.