I’m a bisexual polyamorous woman in her 40s, and I’m fortunate enough to have both a girlfriend and a boyfriend. My boyfriend is my primary partner; we live together and have been dating for a little over four years, while my girlfriend and I just passed our one year mark. Both of my partners also date other people, and they get along splendidly with each other! I’m really lucky.

Here’s the thing: I’ve been openly bisexual since my teens and have harbored a longstanding sexual fantasy of having a threesome with two of my partners. I recently shared this with my partners when I was a bit intoxicated, and to my shock they both seemed game!

Now they’re looking to me for next steps, but (in the sobering light of day) I’m starting to doubt myself and worry that this is too good to be true. Is it a terrible idea, to invite both of my partners in the bedroom with me when they’ve never been intimate with each other before? What’s my responsibility here? Am I opening my otherwise stable relationships up to potential conflict, or should I just shut up and allow my sexual dreams to come true?

Hello hello you gorgeous, perverse heathens! I’ve missed you so. I hope you’ve been enjoying the content brought to you by my guest columnists, and I thank you for your patience while I mucked my way through a dull period of creative apathy. If there were ever a topic tempting enough to lure me back from my hiatus, however, a quandary about group sex dynamics does the trick nicely!

To say that I’m a fan of threesomes is an understatement of enormous proportions. Much of the sex I had in my twenties as a non-monogamous person involved multiple partners, and lord was it glorious. I was fortunate enough to have a primary partner at the time that was as reliably DTF as he was deft at navigating the intricacies involved, so much so that I pulled him in to help me give you the absolute best threesome advice possible! Aren’t exes grand? (Thanks for the ASSist, you handsome devil!)

Ask your partners about any past group sex experiences they’ve had, and have them include details about what worked for them (as well as what didn’t!).

It’s perfectly alright if, like you, your partners have never indulged in group sex before. However, if they have, an opportunity presents itself to improve upon the past! Perhaps your girlfriend was once pressured into a threesome and has been craving group sex with more agency and autonomy. Or maybe your boyfriend had a threesome he barely recalls because of the alcohol intake of all involved and is looking forward to having a ménage à trois he can be present in. By encouraging them to share their experiences - for better or for worse - you’re doing essential research that will pay off for all three of you!
Take the preexisting dynamics of your sexual relationships with each individual into consideration.

Do you engage in Kink or BDSM practices with one partner, but not the other? Is sex rougher with one partner, and more sensual with the other? Reflecting on the specifics in how you connect with each person will give you more clarity on where your partners’ overlap areas may lay. It could also enlighten you to group activities that you may want to avoid altogether. For example, if you and your boyfriend typically engage in rough play where he dominates you, you want to be certain that your girlfriend will be comfortable being in intimate proximity to that dynamic.
It might be a good idea for you all to go on a date before the threesome.

It’s wonderful that your partners already respect each other and enjoy one another’s company. However, the boundaries between them are about to change. It may be a good idea for the three of you to spend some flirtatious time together in the days or weeks prior to your threesome being actualized, now that it’s been laid out on the table. It gives you all a chance to engage in and enjoy this new erotic energy being cultivated and could build up even more anticipation for the threesome itself!

4. Encourage your partners individually to share what excites them about this particular threesome, as well as any concerns they may have.

Discussing your feelings about the threesome as a group is critical, but you want to make sure you’re also initiating these conversations one-on-one. No matter how friendly your partners are with one another, they are likelier to hold certain vulnerable shares back - namely, any reservations they may have about the impending threesome - when you’re all chatting about sexy stuff together. You have cemented yourself as a “safe” person in both of their lives - make certain you’re available to them individually to hold space and validate any insecurities or worries.

5. What kind of communication between your two partners are you comfortable with?

It’s natural to want to “stoke the fire” before getting busy. Are you comfortable with your boyfriend and girlfriend sending dirty texts or photos to each other prior to the main event, or does the thought make your stomach twist? As soon as you’ve taken intentional time to interrogate your feelings around it, communicate those feelings to both partners clearly and compassionately.

6. Logistics, logistics, logistics!

You’ve got the “who” part of the planning process down; now, determine the “when” and “where”. A house without roommates or other family members present is always a good idea, as is a place with non-intrusive neighbors. Consider if someone will need pet or child care arranged in advance. Finally, I always recommend leaving as much time as possible for any new sexual experience, so make sure you’re all reserving enough time (a few hours? an entire evening?) to allow things to develop and evolve organically.

7. Make sure you’re all on the same page about safe(r) sex practices.

This one’s self explanatory. If you’re not fluid-bonded with both partners already, discuss whether or not you all want to make that jump. If you don’t, make sure you’re all in agreement over which safe(r) sex methods - condoms, dental dams, gloves, etc - you’ll want to have on hand for the main event.

8. Acknowledge your unique responsibility as the “hinge partner”, but don’t let it overwhelm you.

Worrying about the possible “consequences” of orchestrating a threesome between you and your two pre existing partners isn’t silly. Quite the opposite - it’s smart. You’re dipping your toe into the unknown and no matter how much forethought you give to the situation, there’s only so much you can control. Plus, there’s little anonymity in a polyamorous threesome; the stakes can feel higher to all involved knowing that everyone is emotionally invested in each other.

Trust me, I know the feelings well. I’m a lifelong control personality who historically has taken on the role of “protector” in all of my romantic relationships. When it comes to group sex I’m almost always the common denominator, which used to make me feel entirely responsible for the perceived “success” of the interaction. Time and time again I’d find myself the focal point of multiple writhing, attentive bodies, yet I’d be unable to relax and receive the pleasure being offered to me. I was too distracted by my concerns about whether the others were having a good time/getting enough attention/etc etc. Don’t fall victim to these merciless anxiety loops; you’ll drive yourself crazy while denying yourself the pleasure you deserve. At some point you have to trust that your partners are adults who can and will take care of themselves. If you can’t trust them to do that, then why are you dating them in the first place?

9. What happens AFTER the threesome?

I’m referring both to the immediate and non-immediate aftermath. Will everyone be spending the night together, or will you all be sleeping separately? Will anyone need any aftercare? If so, what will that look like? Moving forward, will anything in your relationship dynamic change? What will your disclosure politics be around telling other people about your threesome? It’s also a good idea on your part, reader, to preemptively schedule intentional time with each partner in the days following the threesome. You want to reinforce your bond with both your girlfriend and boyfriend individually, as well as provide opportunity for them to decompress and process through the experience.

10. It’s gonna be awkward. Expect to hit the sheets and have a few laughs!

You may think that [my ex and] I have been gifting you this wisdom so that you may avoid awkwardness when you all fall into bed together. NOT THE CASE! Sex is awkward by definition. Sex between two people who have never fucked before is awkward. Sex between THREE people gets EXTRA awkward!

There are going to be lots of messy fluids and body parts tangled in sheets and weird noises and times where you accidentally forget someone’s boundaries and have to pull up short and apologize. You’re going to try positions you’ve only seen in porn and fail spectacularly. Your dog may panic at all the fuss and serenade you with a relentless series of desperate cries and howls. Allow for the awkward. Embrace the awkward. Find the sweetness and humanity in it. Laugh together and bounce right back from it knowing that the awkwardness will only add to the richness of the stories you’ll reflect fondly back on.

Andre Shakti returns as your resident polyamory pundit to assist a reader in navigating her first threesome!