How To Make Group Sex Fun

Here’s a question that someone sent me about group sex:

My boyfriend and I have been together for a year. I love him a lot and the sex is great. He is the most sex-positive person I’ve dated, and is open to experimenting with me. I am curious about including others in our play, and he says he would be open to that. I think it could be really hot, and add extra fire to our relationship. This is a fantasy I’ve had for a long time, but I felt unwilling to explore it when I was single because I wouldn’t want to feel overexposed or forgotten at the end. Now, knowing that my boyfriend would be by my side, I am beginning to revisit the idea.

I am nervous about my own capacity for jealousy and emotional turmoil, however. It’s hard for me not to feel anxious when thinking about him cuddling or kissing someone else, for instance, or him growing emotionally attached to a new partner and wanting to be with them one-on-one. I don’t think I’d be a good candidate for polyamory, therefore, nor a completely anonymous hook-up, but maybe some form of swinging could work?

Rationally, I think our bond is strong and that he’s more capable than I am of separating sex from emotion — it might be me who struggles not to get attached. I should add that I never had “casual” sex when I was single, always waiting to be in a relationship, and have had trouble relaxing with partners I didn’t feel totally at ease with. Nevertheless, the fantasy persists, and I’m wondering if you have any advice about things to consider or ways to figure out whether this is an idea worth exploring, or if it would be best left in the realm of fantasy.


Step 1: Explore The Roots of the Fantasy

Whenever anyone shares one of their fantasies and asks what they should do about it, I always have the same question: what it is about that fantasy that makes it so hot/sexy/interesting/compelling? I think that’s the place to start because once you have a handle on that, you can decide what to do with it.

It might seem like the answer is obvious, but it really isn’t. Different people can have very similar fantasies but with totally different motivations. For example, a fantasy of group sex might be motivated by:

  • Wanting to be the center of attention from multiple people
  • Wanting your partner to be the center of attention from multiple people
  • Wanting to watch your partner with someone else
  • Wanting your partner to watch you with someone else
  • Wanting to show off together to an audience
  • A desire to have sex with people of a different gender, body type, or appearance from your partner
  • Finding pleasure in breaking the rules and doing something “naughty”
  • A desire for sexual adventure with someone new while also feeling the safety of being with an established partner.

These are just the tip of the iceberg. There could be lots of other pieces to your individual sexual puzzle. The more you can understand where your desires are coming from, the easier it is to decide what to do.

One good way to do that is to first explore the question: what about this fantasy is extra hot for you? What are the parts that keep coming to mind when you’re masturbating or having sex? What are the elements of the fantasy that make your orgasms amazing? What are the parts that make the story feel incomplete if you take them out.

When you know what pieces of the fantasy are extra sexy for you, you can ask yourself the second question: what is it that makes those elements hot? What patterns do you see among them, if any? How do they connect to your pleasure? Explorations like that can help you figure out what motivates the fantasy. And once you have that, it becomes a lot easier to decide what you want to do with them.

You still have lots of options at that point. You could co-create sexy fantasies while having sex with your boyfriend, taking turns talking about them, and never actually have sex with anyone else. You could role play by dressing up as two different people and pretending to “meet” at a bar or café. You could find someone (or more than one person) and watch each other over webcam while having sex with your boyfriend. You could go to a sex club or a swinger party and watch or show off without physically engaging with anyone else. You could have a one-time fling with someone. You could find someone for threesome booty calls. You might find any of these possibilities exciting, and you might find any of them boring. When you know what’s behind your fantasies, you’ll be able to make better decisions about which ones to try (if any).

Step 2: If You Decide to Fulfill the Fantasy

I think it’s clear that you have lots of options when it comes to deciding whether you want to enact your fantasy. If you decide to explore group sex, here are some useful tips.

One of the challenges when dating or having sex with more than one person is how you manage everyone’s attachment. I’m not talking about attachment in the Buddhist sense of the word, but rather, how strongly people connect emotionally with each other. You need enough connection to feel comfortable and safe in the situation, but not so much that it strains your relationship with your boyfriend. Everyone will have a different range that feels good to them, and there are lots of ways to keep in the zone.

For example, you might want to play with someone at a party and then go home with your sweetie. You might want to have recreational sex, without a lot of kissing or cuddling. Or maybe no kissing or cuddling at all, if that works better for you. You might want to reserve certain sexual activities for the two of you. You might want to have sexy dates and not have sleepovers. Going home and taking a shower, rather than sleeping with someone (in the literal sense), is a great way to reduce attachment.

That might get a bit tricky for you, since you have difficulty relaxing with new partners. Finding the sweet spot between “enough connection to help you feel safe” and “so much connection that it affects your relationship” will mean making some mistakes. There will be times that you accidentally step out of the zone and feel unsafe or jealous. That doesn’t have to be a disaster because you don’t need to expect or demand perfection. An experiment is only a failure if you don’t learn anything. So if you have an experience and it doesn’t work the way you’d hoped, it’s not a failure if you get useful information for the future.

In my view, having rules is really helpful when you’re trying out group sex. There are lots of pieces to the puzzle and it’s hard to figure out what does and doesn’t work when there are too many changes all at once. So if there are things that you know or feel really sure you don’t want to do, make that decision and talk about it with each other. Agree to keep to it, and do not change your mind(s) when you’re turned on. It’s easy to think it’ll be ok, and it very well might be. But if it isn’t, it’ll be a trainwreck. However much fun it is in the moment, it won’t be worth the hangover. Besides, you can always revisit the issue in a non-sexual setting and renegotiate the boundary as things change.

Tristan Taormino’s book Opening Up includes chapters on different kinds of open relationships and the sorts of rules that people often use. Since different relationship styles (swingers, triads, solo poly, etc.) have different shapes, there are lots of ideas in the book to consider. It will help you not have to invent the wheel over and over.

Step 3: A Few Potentially Useful Ideas

If you move forward with trying group sex, here are some suggestions to make it fun.

1) Anyone can join in at any time

I think that group sex works best when anyone can join in at any time. If you’re feeling left out, that’s a good time to join in rather than sitting across the room and wishing they’d notice. When you’re having the safer sex talk, say something like, “I want us all to have permission to sit back and watch at any time, and to join in at any time. I want to make sure that nobody ever feels left out.” Making that explicitly part of the conversation will give you more room to take charge of your own experience, rather than hoping that someone else will do it for you. That makes group sex a lot more fun.

2) Use a safeword

It’s a great idea for you and your boyfriend to agree on a safeword that means, “I need to get out of here.” Knowing that he’ll back you up and leave anytime you need it will help you feel safer and give you more freedom to explore.

It can feel sometimes feel awkward to say something in front of others. Fortunately, you can also use non-verbal safewords. My partner and I use three taps or three squeezes on an arm or leg to signal, “let’s get out of here.” If one of us uses it and doesn’t get a response, they repeat it in a few seconds. The other one then signals “message received” by returning the three taps/squeezes. That’s gotten us out of some boring dinner parties, and it’s pretty much invisible to anyone else.

3) Get really good at your safer sex talk.

Having direct and clear conversations about safer sex can take practice. Check out Reid Mihalko’s Safer Sex Elevator Pitch, and practice with your boyfriend. After all, there’s a good chance the two of you will be having a safer sex talk together with someone else, so you’ll be hearing each other’s anyway. Try it out together and see what words feel most authentic to you.

4) Accept that feelings will sometimes get hurt.

Group sex can be a lot of fun. And there will be times when someone’s feelings will get hurt. We don’t always know where the edges of our comfort zones are until we cross them. It hurts, just like being sore from overdoing a workout hurts. The better the two of you are at taking care of difficult feelings, the smoother things get.

Yes, I know that that’s true of monogamous relationships, too. But when you’re adding people to the mix, there are more variables in play and that increases opportunities to step on someone’s toes. I’ve seen lots of people go too far, too quickly with group sex or polyamory, so start off slowly and take care of hurt feelings before they turn into resentment. Resentment is the biggest relationship killer, so do what you can to avoid it. And there will always be another opportunity to take things further, so it’s better to move gradually and keep the inevitable hurt feelings more like a bruise than a broken arm (or heart).

5) If it doesn’t work for everyone, it doesn’t work for anyone

If one of you is having a great time and the other one isn’t, that’s not a fun evening. Exploring group sex as a couple means that it has to work for both of you. So commit to each other that if one of you isn’t enjoying it, then it doesn’t work for the other one. That will give you more permission to speak up if things don’t feel right.

I hope that helps!


If you have questions about how to make sex easy, send it my way. I’d love to hear from you!