You and Threesomes: How to Know When You’re Ready

The used panty marketplace

Threesomes aren’t just for grandma’s 1970s swinger party anymore. When one in seven people in the states have dipped their toes in these sexy waters at least once, it’s no surprise you found your way to this article. If you’re reading this, you’re at least a little bit curious about the joy of three, aren’t you? 

But before lapping up that first, golden opportunity quivering on your plate, make sure you’re equipped with the tools to have all parties coming back for more. Sex should be juicy and thrilling, and multiple partners should only make it more delicious. But the million dollar question is, how do you know when you’re ready for a threesome? And how do you even find the other two folks to get down with in the first place?

Before you go searching for the puzzle pieces you need to complete your fantasy menage a trois, there’s a little (okay, a lot of) groundwork you’ve got to lay for a first time you’ll never forget.

The first step is simple:

Throw your assumptions out the window

Unlearn everything you’ve been told about threesomes before. The western relationship to group lovin’ generally consists of lopsided ideas from porn and even cultural staples like Friends. Threesomes tend to be marketed as a circus for a straight man’s pleasure. The reality is more nuanced (and way more fun). The thing is, each threesome is unique. The boundaries and positions that work for some groups will crumble for others.

To have the best time? Enter each threesome (especially your first) with a fresh mind. There isn’t a cookie cutter way to find some cuties, flirt, and start going to town, because everyone’s sexuality and identity is a little delectably different. 

But there are a few ways you can prepare so the night goes as smoothly as possible. When you flirt with someone, listen to their cues – and in bed, listen even harder. If you thought it was work to intuit one partner’s needs, get ready to double up with a second honey in your bed.

Once you’ve shaken all the dust bunnies and porn misinformation from your head, you’re ready to dig in and examine your motives up close.

Know your why

The most important thing to ask yourself is this: what’s pushing you to get down with a duo?

No matter what the specifics of your answer are, the long and short is that you’re only ready for a threesome if you want to do it because it makes you happy. Maybe you want to explore your sexuality, or want to learn to service a new kind of bod. Maybe you just want two mouths on you at once (who doesn’t?). Whatever your reason, make sure your own desire is at the heart of it – nobody else’s. In fact...

Never do it for someone else

No matter how much you love your person, how cool you want to seem, or how much social pressure you may face, if you’re not feeling it, then don’t do it. Threesomes may just not be in your cards right now – or maybe ever. And that’s totally okay. As much as I adore a good roll in the hay with two (or three) cuties, I don’t believe threesomes are – or should be – everyone’s cup of tea. 

Sexuality is beautiful because there’s no wrong way to do it if consent is involved. So if you’re only agreeing because someone else really wants it, take a step back and reevaluate your bedroom priorities. It may be time you talked to partner about what you really want.

But don’t just think about you, either.

While your desire deserves the front seat, don't ignore everyone else’s. A threesome is an intimate group activity, and all parties need to be heard. Sex with only one person can be raw and is by nature vulnerable – sex with two people is only more so. 

Some people dive into a threesome just to fill a space, to feel wanted, to get attention – looking at you, pillow princesses. While we all want attention sexually, it doesn’t mean we should be diving in to get sexual favors to validate our own worth. Speaking from experience on both sides of the equation here: if you go into group sex to find some kind of validation, you’re liable to hurt someone else by making them feel undesired.

While laying back and enjoying the ride is fine, and threesomes do make you feel sexy AF, a threesome requires active and eager participation for it to flourish. So if you know your desire for a threesome is genuine, you do you. Don’t worry about inexperience, awkwardness, or a lack of finesse – the right partners won’t mind showing you the ropes.

Should you wait?

If you had a tickling in the back of your mind thinking about all this, look out for a few key red flags that let you know you should be waiting – or that a threesome may just not be for you.

Insecurity

A little insecurity is natural in our body-hating culture – just ask anyone on social media. But if you’re constantly comparing yourself to other bodies, or are consumed by shame with your own frame, a casual threesome may not give you the kind of sexual healing you hoped for

When I was at my most insecure right after going through menopause under thirty, I had a few threesomes that I wasn’t emotionally ready for. It wasn’t jealousy, fear of my partner leaving me, or anything like that. It was suddenly being confronted by new and beautiful bodies that I didn’t know I could please, when I was barely able to relax enough to enjoy myself with my partner. I spent most of those liaisons insecure, wondering what I needed to do differently, judging my body and pleasure and skills against what my lovers must have encountered before. It sucked.

But I was stubborn. I’d loved threesomes and polyamorous dating before that happened, and  so I forced myself to keep doing what I knew I loved in theory. Instead, I just ended up hurting people’s feelings, including my own.

I should have waited, but I didn’t, and now that I love my sweet and imperfect bod as is, I have one hell of a time invoking the pleasure gods with babes of all stripes and identities. So trust yourself, first. It’ll make your threesome immeasurably sweeter.

Jealousy

This green beast rears its head with different power dynamics. Maybe you’re in love with one of the people, maybe they’re in love with each other, or maybe you’re in love with both of them. Whatever it is, there’s nothing worse for a threesome than unchecked jealousy.

Take a second to think about it right now. If you’ve got at least one of your threesome babes in mind, close your eyes and picture them making out with someone else. Picture them giving oral to someone else (and vice versa). Do any of those make your stomach roil? 

Jealousy is a learned behavior in our relationships that comes from a lot of junk in our lives, including a lack of communication and trust. Feeling jealous is how we’re raised, so don’t close the book on a threesome just because picturing your lover smooching on someone else raised your hackles. Instead, read up on the magic of compersion. Jealousy’s sweet, tender opposite, compersion is that feeling of joy you get when your partner experiences pleasure. 

While that may sound wild to you, you can cultivate it by reading about it, talking about it, and stepping into the confidence your relationship really needs.

I’m ready – what now?

So you passed all that preliminary check stuff with flying colors. Now you’re ready to start preparing for the reality of your very first threesome.

If you’re picturing someone coming over and hot sex unfolding immediately with all your fantasy positions and little-to-no talking involved...you’re in for a wakeup call. Don’t expect someone to hop into bed without a date beforehand. No matter how casual the encounter, odds are everyone will want to get to know each other first. Go grab a coffee or beer, or take a walk in the park. When you do, flirt just like you would on a two person date. 

If you want to find someone for a threesome, try making a dating profile (just be transparent about what you want), or go for the meet cute by being an upfront person in your regular haunts.

Being ready to actually take the three-way date out on the town is your final test to make sure you’re equipped for a threesome. If you get jealous or feel weirded out, take things slow and communicate at every step.

Be ready to dish 

When you’re on that date or enjoying a nightcap back at home, you’ll have to talk about everything eventually – your health status, obviously, but also about your past sexual experience. 

If this is your first threesome, you might find yourself encountering acts totally new to you. 

And that’s okay. I’ve been on both the clueless end and the experienced one at different points in my threesome game, and telling your partners about your journey beforehand is the best way to smooth any bumps before they arise. When you let someone know you’re new to an activity, you save them from wondering why you’re avoiding certain acts – and save yourself from bungling through your first time eating someone out while pretending to be a pro.

If you communicate your greenness, you don’t have to worry too much: someone in your trio will probably be more than happy to teach you, or you could enjoy the sweet satisfaction of being a voyeur while someone else goes to town. 

Different strokes

No two situations are identical, but there are three common configurations for your first threesome. Each come with their own unique challenges and perks:

A couple spreading their wings

Couples have a lot in their corner when it comes to a threesome. At best, we’ve got a fun and trusting relationship to fall back on. At worst, we have jealousy and insecurity bubbling underneath. Just like you got to know your own motivations earlier, you’ve got to get to the bottom of why you and your partner want to explore the world of group sex now.

If you’re looking for a hookup because you want to explore desire and share new sensations, then full steam ahead, baby. But if you’re thinking a threesome will jumpstart a sex slump – pump those brakes.

Do what now?

If sex has been lackluster between the two of you, how can you expect to find sex that works for you (and avoids jealousy) in a threesome? Outsourcing sexy vibes isn’t a substitute for a good sex life with the person you’ve already been dating.

If things have been less than arousing in your home life, try spicing it up there first. Get into toys, talk about fantasies, or even put sex on your Google calendar to make sure you’re both getting the attention you crave.

And if you do those timed sessions? Don’t just schedule a quickie. Set aside an hour or three and use them to really explore. Play with each other’s bodies, try out new toys, and linger with a good massage. 

Once you’ve rebuilt that fire and have it crackling between you two, you’ll be ready to have a great time with another person. The third person entering your space is a real, breathing human. Trying to use them as a tool to mend your relationship isn’t fair and never ends well. 

In fact, be kind overall

You already have an emotional and physical bond with your partner. The new person may be a total stranger, or a friend who’s never gotten sexy with either of you. You have the advantage of a safety net – they don’t. Treat their desires and opinions as sacredly as you handle you and your partner’s. When you do, everyone will have a sexier time, and they may be game to come back and do it again.

Make sure you and your partner make a concerted effort to give the third person pleasure. It can be an excellent bonding experience with your human, and one of the spiciest joys to share between three people. By focusing more on the other person’s desire, you’re helping level that tipped playing field.

Know your power

When my husband and I were first getting our sea legs in the polyamory and threesomes world, we made a lot of mistakes. I still cringe reflecting on how totally clueless I was about the uneven power dynamics that come with being the couple. Don’t follow my example! You can skip those first flubs that hurt feelings if you first read up on couple privilege. While there’s a lot of interesting conversation whirling around about whether privilege is the right word to use, “couple privilege” breaks down all the kinds of perks you receive as a couple.

Couple privilege in a threesome boils down to this: you have an existing relationship there. You have someone to mull over the details with afterward. Your partner is the person in this trio that makes you feel safe. The person you’re inviting into the bedroom? They don’t have that security. 

This advantage crops up again when it comes to sex itself. If you have years of experience on how to make your partner moan, you have the upper hand again there.

To make things more even, communicate with as a trio. If you and your partner have specific rules about what the new person can and can’t do, ask yourself if you’re considering their needs, or just shoving them into a fantasy of yours. 

When you’re about to get frisky, you owe it to your casual partner to communicate explicitly about what your boundaries and turn ons are. The thing is, if it’s relevant to having a threesome, all three of you need to know. Whatever you said to your primary partner about expectations for the night is something the other person deserves to hear, too.

Don’t worry about going into details of trauma or highly personal past baggage, but do communicate things like “penetration feels off the table for me right now” or “I think I’ll just be watching this part.” Saying what you want and don’t want lets your newer partner know your boundaries, so they don’t step on any sore spots – and you don’t step on theirs. 

Sometimes it smarts to realize you have the upper hand and may have been hurting someone without meaning to. Couple privilege isn’t an inherently wicked thing. We live in this beautiful, messy, and painfully unbalanced world, and the best thing we can do is try to smooth it out. Instead of being sad, or denying the benefits you have, work hard to make sure your new late-night lover is getting all their needs met too.

Saving the relationship

Final thing about couples: if you’re thinking about having a threesome to salvage your relationship, just don’t. Period.

Flying solo

If you’re single and looking to get down with a duo, you’re in for a slog leading to a sweet, sweet reward. There are a lot of tricky obstacles and hoops to jump through ranging from straight guy rage to end-of-relationship blues, but by and large finding that dream duo is more than possible. 

You’ll have no problem finding someone interested, and you’ve got the space to be picky. Ask yourself what you’re looking for, first. Do you want two queer cuties? To give a new kind of oral? To see what the straight-guy fuss is really all about?

As much as I would love to think that other couples put in work to treat their lovers well, the truth isn’t so kind. If you’re brand new to the threesome world, my number one advice is this: run from anyone saying they’re unicorn hunters.

Unicorn hunting is when a straight couple wants a bi babe to fulfill their fantasies. Generally, they don’t care about what you want, and they’ll probably have some strange rules (like no making out). Instead of wanting to connect with you, a real human, they’re just looking for a doll to fill their fantasy void.

You can try your luck on Feeld, an app designed for the threesome experience (just watch out for those unicorn emojis!). Personally, I’ve had luck there as a couple, and it’s more queer friendly, meaning you won’t just be encountering folks who don’t care about your time.

Otherwise, your best bet seems to be meeting cuties in the real world. That’s where I’ve had most of my luck. Personally, I think it has something to do with my husband’s jewelry and chest hair. Maybe it’s our copious amounts of glitter. Whatever it is, the real world reaps real rewards if you’re looking for a couple. 

Your best bet is finding sillier people, ones who laugh and get down on the dance floor, at karaoke, or at a costume party. If they’re open and seem like a blast, the worst you can do is flirt and get turned down.

Safety first!

Look, meeting people out in the real world is fun, and maybe I’m just preaching to the choir, but put your safety first. I may have met people in all three of those scenarios described above, but we all met up sober later in the week for a good time – I’ve never asked a stranger to come home with us that night. It’s creepy, and it isn’t putting your safety in mind. If you like the couple and want to sleep with them, ask for their numbers and be clear about what you want them for. If they’re game, things won’t change the next day, and you can meet them clear headed to make sure sober you wants the same exact thing drunk you did.

NSA friends

This is a near-mythical status. Normally, there’s feelings involved somewhere, right? If you’re a lucky duck who can find two friends down to play for your first threesome, approach it like you would in any other configuration. Get to know your boundaries by going out and setting the flirty tone first with some dancing or a cocktail. Before the clothes come off, talk about hard limits, fantasies, and favorite activities.

This situation is really the hardest to come by, but if you find yourself this lucky, keep everyone’s feelings in mind and play like you want these people to remain your friends long after the clothes are back on.

It’s worth noting that these three configurations are common for your first threesome. If you’re polyamorous and dating both people, then you’re probably not new to the threesome game. If you are, then be considerate with your partners, love them well, and kiss them in equal measures. If you communicate to them both equally, things will be just fine.

Once you’re in bed, remember that you are always in control. Dial it back at any time and talk to both parties about anything that comes up for you. There’s nothing wrong with changing your mind, no matter how hot and heavy things have gotten. 

You ready?

Stay open through the whole experience, and communicate more than you think you’d need. If you’re rip roaring to head into the world of threesomes tonight, maybe even make a profile on Tinder or Feeld – just make sure your intentions are crystal clear.

And last of all – when you meet these new cuties, whether they’re into ecofetishism, selling panties, or just plain old missionary, respect their fantasies as much as your own. Who knows? You may just uncover your newest kink.