Hester: 1, 2, 3, Peter, Paul & Mary

The first time I had group sex, it was out of the blue on a cold winter night with three of my best friends. The second time, I was in a relationship and we planned it. Currently, my SO and I are working on making it happen for a third time. What this means is really quite simple: I adore group sex, I wish I could have more of it more often, in all sorts of different configurations, and if you think you might want to try it, you absolutely should.

Based on my personal experiences, I can give some fairly solid advice. It will be tailored to specific scenarios, of course, but can perhaps be applied more broadly if you use your imagination.

The better group sex experience for me was the one with thought behind it. My partner and I constantly brainstormed different women we thought might fit the bill — it was half business deal, half dirty talk. Our ideal threesome partner was female. It was the classic “boyfriend wants to have sex with two girls” scenario, except that, in this case, his girlfriend really wanted to have sex with the other woman too. This can be something of a sticking point; I have heard many a girl lament that her boyfriend wants to have a threesome, and that she would do it, but only to make him happy. In cases like those, I’m inclined to suggest that it is actually worth trying. Maybe it starts as a way to please your partner, but morphs into something actually pleasurable for you. Or, if it’s something that you’re genuinely considering, maybe that’s hinting at a heretofore unacknowledged part of you that’s actually quite curious about same-sex sex. Just make sure that within the terms of the threesome is the ability for anyone, at any point and for any reason, to call time-out.

Here’s how my (very well planned) threesome went down: when she came over, we sipped wine, went over ground rules (she wasn’t comfortable with semen getting anywhere on her body, we developed a safe word), and went to town on each other (on the floor). As it turned out, I really liked watching my boyfriend kiss (and do other things to) another person — and then being able to kiss her myself. Plus, the extra hands and mouth resulted in an almost-too-good sensual experience. I must admit I was surprised by my lack of jealousy, as I can be rather territorial. But the voyeuristic thrill of seeing my boyfriend with someone else trumped everything. Plus, I was in control! I hadn’t stumbled upon some secret tryst that I wasn’t meant to see. Jealousy stems from insecurity, but I was far from insecure, because we (all three of us) orchestrated this experience. We had a mutual fantasy and made it happen.

It is possible that I just completely lucked out: having an open-minded partner and finding someone into the idea of fucking us. Beyond luck, though, I am convinced that this has everything to do with the planning that went on beforehand. Planning need not be as in-depth as it was in the scenario I described (you never know when the possibility of group sex might present itself). However, it does allow you and your partner to know what to expect from each other — you can both be open about your anxieties, hopes, and dreams. You can explain what makes you nervous and what turns you on about group sex. This will be valuable when the act is actually happening, and will help minimize pain and jealousy. It’s important to let your threesome partner in on the intimate chat, too. Our pre-sex discussion gave us all a chance to feel more comfortable, and to lay some ground rules and talk about our personal experiences. I would bet that this works the other way, too — if you want to ask a couple to have a threesome with you, it would be beneficial for everyone to talk about it first. Additionally, in terms of practical threesome-having advice, if you talk about positions and specific things you’d like to have happen, it’s not only sexy, but also a good way to establish a game plan. A lot of threesome-based nerves stem from not being sure about how it’s all going to work, and while I’m all for improvising and going where the spirit moves you, it can help calm some of those jitters if you dream up potential positions beforehand.

Of course, you can never guarantee that you will have a 100% foolproof threesome, especially if there is a relationship dynamic involved. Jealousy can rear its ugly head at unexpected times, no matter how comfortable everyone feels. Thus, I highly recommend establishing a threesome-specific safe word that everyone knows about. When I didn’t have one (i.e. when I stumbled across three of my friends having sex and was invited to join), I felt trapped mid-foursome and had no easy way out. Even though I am usually very communicative during sex, this scenario was somehow different from just another hook-up, and I found that the cat got my tongue and didn’t let go until our awkward encounter slowly fizzled and we all slunk away, never to discuss it again (until recently — we all laughed). For me, communication has made all the difference between being wholeheartedly into group sex and feeling somewhat detached from it.

So, I’ll let you all know how my next group sex experience goes. I’m hoping it will be with a man, so that I’ll be able to broaden my horizons and test my limits. The threesome might not happen for a while, as my SO and I have yet to find someone who is the right mix of trustworthy, wild and non-threatening (I swear I’m not using this column to solicit a threesome partner…). I’m confident, though, that taking our time, and fantasizing about different positions in the meantime, will allow us to find just the right person and will be well worth the wait.

Also, anyone who has had an overwhelmingly positive experience with impromptu, unplanned group sex, please comment about it. I don’t want to imply that such a thing doesn’t exist, I just haven’t experienced it!


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4 comments

  1. 1
    pressured? says:

    ” n cases like those, I’m inclined to suggest that it is actually worth trying. Maybe it starts as a way to please your partner, but morphs into something actually pleasurable for you”

    That sounds like a TERRIBLE idea. There’s a whole big can of worms here that I don’t really know how to begin addressing.

    1. 0
      Hester says:

      I don’t mean that a woman should give in to threesome pressure under any circumstances — I mean if she is curious and is willing, it could possibly turn into something more for her. This entire article keeps circling back to consent, and I would never suggest that someone engage in something they haven’t actively decided to do. Plus, I constantly point to the importance of the threesome being a safe space — if the woman in this scenario realizes she’s deeply not interested, she can stop. I think sexual adventuring is important, and that’s why I’d encourage someone to try a threesome who is a little on the fence.

  2. 0
    Nebbish Straight Guy says:

    “This can be something of a sticking point; I have heard many a girl lament that her boyfriend wants to have a threesome, and that she would do it, but only to make him happy. In cases like those, I’m inclined to suggest that it is actually worth trying. Maybe it starts as a way to please your partner, but morphs into something actually pleasurable for you.”

    Haha, oh dear God. Just when I thought the Daily Gazette couldn’t get more bizarre, someone posted an article about group sex. This is just too good. Please, come ’em coming!

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