The Many Configurations of Double Penetration


And you may tell yourself, “This is not my beautiful house.” And you may tell yourself, “This is not my beautiful wife.” And you may ask yourself, “Well… how did I get here?”

At least, I’ve asked myself that plenty of times when vacationing in other people’s relationships.

My Turn Me On episode focuses on group sex from the perspective of a man that plays the third party for a lot of couples. Appropriately, I’m writing it the morning after attending an orgy. Bryde and I originally discussed me offering the viewpoint of an ordinary guy in 2017, dating in the world of Tinder, Bumble, etc., but apparently providing a helping hand to married folks is a niche in its own right. So how did I get here?   

I think I experienced a pretty healthy sexual upbringing. I discovered the Sears catalogue at five, the Red Shoe Diaries at 10, poorly executed oral sex at 12, and good old penetration at 16. Then I became a monogamous relationship kind of guy and spent the next decade with wonderful and patient partners, all the while reading Craigslist ads in secret and fantasizing about meeting up with strangers to fuck. Good at love, bad at communication.

Fast forward to me in a new city as a freshly single adult, realizing that I could now act on those fantasies without hurting the people I care about. I started to dabble. I went for coffee with a dominatrix. I worked the grill at a BDSM BBQ. I used a rubber ducky paddle on a diaper-clad adult as they sucked on a pacifier. I put on a stage show with two women my first time at a sex club. And I quickly earned myself a reputation as a reliable addition for MFM threesomes. Probably because the kink scene is surprisingly small.  

Sleeping with couples isn’t my fetish, but it can still be really, really fun. You get to help others check a popular item off their bucket list. You get to see a beautiful woman basking in her time as the centre of attention. Ideally, you get to feel a lot of wonderful energy from everyone in the room. And you get to meet very interesting people, who are enthusiastic and open minded after time spent operating outside of social norms. What better way is there to get to know new friends than taking all your clothes off?

But things don’t always go smoothly. There is a lot of room for hurt feelings in group sex scenarios, especially with MFM threesomes. As a guest, you don’t know the intricacies of their dynamic as a couple or what their real motivation for the arrangement is. You don’t know the ins and outs of who they are as sexual people. Sometimes the fantasy isn’t what one or both parties expected. Sometimes people feel overwhelmed or left out because there are only so many hands, so many holes, and so much energy to expend. Sometimes it just isn’t as fun to watch another dude fuck your wife as you thought it might be. Whenever jealousy and fragile male egos set in, things go south real quick. I’ve watched people drink too much. I’ve witnessed slut shaming. I’ve been the catalyst for break ups. None of that feels good.

It all comes down to communication. Laying down expectations, boundaries, and goals for the night. Open and honest talks before, during, and after can change a potential disaster into an experience that everyone walks away from with a spring in their step. And talking about those practicalities in detail can be surprisingly good foreplay. Last hint: whenever possible, debrief over brunch.

Playing the third can teach you a lot. There is so much awkwardness inherent in these situations, but navigating that awkwardness is worth it. As a single dude, you get the incredible privilege of making people happy, fulfilling your own fantasies, and gaining insight into what sort of partnership you might want in the future. You get to fuck and grow as a person.

What a time to be alive. 

- C

Jeremie Saunders