A vacation foursome, and non-monogamy lessons in dating other couples

Leading and frame are very important

A recent conversation reminded of how, many years ago, I volunteered at a sex party / non-monogamy mixer (an event that is sexy but not the place for actual sex), and, after the mixer, a guys hosted a small “after party,” which was just a place for people to continue hanging out: nothing fancy. The “after party” was about 15 minutes away, and I ended up with a couple who seemed cool–I was attracted to the girl in the pair, who we’ll call “Museum Girl.” We exchanged numbers and I promised to introduce them to the woman I was dating at the time. They liked me and were hoping this could head in a romantic direction.

A few weeks later, we all met up at a cool bar for drinks: me, my girlfriend, and the other couple. It was a bit awkward for me because it was hard to figure out who should be leading, as I didn’t know the guy well and wasn’t sure about their intentions. I should have just led (it is what I’d tell someone else to do), but I make plenty of mistakes and that was one. 

The “date” was fun, they were cool, we all talked about our connections to ENM, kink, etc. but the date was a bit stilted, as no one drove the bus. Normally, I wouldn’t sit across the table from a girl, but, with four people, there wasn’t another configuration that made sense. I’d also normally be attempting to escalate and move physically closer to the girl throughout the date. However, because I couldn’t read the guy, I didn’t want him to feel like I was trying to bang his chick without his buy in. In retrospect, a venue with circular tables or an isolated corner booth would have better.  

In this case my hesitation created space for the women to lead, which was a good resolution to our detente, although one that often fails. In a hetero foursome, and in all ENM and sex party contexts, women have social and other freedoms that men don’t. Most straight men do not have a problem with hot girls doing anything with their partners, so women don’t really need to worry about the boyfriend getting upset, and thus don’t have to awkwardly ask for permission. On the flip side, dudes have to worry about other dudes getting mad if you’re even just talking to their woman, even in an ENM context, and you just never know what people’s boundaries are. Girls like things to “just happen,” but ENM spaces often need some amount of explicit consent for things to work properly. Girls making out with and escalating other girls smooths this process. Since girls aren’t physically threatening, they can act in moments and in contexts where men are restricted. Telling your girl, “Ask that girl if she wants to make out with you,” is often a useful step. 

Back to the date: after about an hour or so of flirty banter, the other girl asked if she could sit on our side of the table. She left her partner and sat next to my girlfriend and basically seduced her in front of us. It was pretty hot. She completely ignored the two dudes, and I think she is the stereotypical bisexual girl who is more into women sexually but prefers to date men for social/monetary reasons. The other girl quickly escalated, telling my gf that she thought she was really hot, asking if she could kiss her, touch her etc. Eventually, we ended the date with soft plans to go away for a weekend and get a house and all have fun together. 

In hindsight, my biggest mistake was after the date, when we were all on a text thread planning out the date, was not getting clarity on what we were all signing up for. We all exchanged STI test info, so it was clear that sex was on the table, but with four people in two couples, there are a lot of possible options, and boundaries weren’t clear. There’s a risk with unclear boundaries, that someone else will treat you like Putin does Ukraine. 

Normally I’m very comfortable talking explicitly about sex, boundaries, etc, but for some reason I couldn’t bring myself to have this conversation in advance. This is a rookie mistake–don’t avoid hard conversations. I did at least have the conversation with my gf and as usual, she reported that she was game for anything and wanted me to take the lead (see above regarding male leadership). Helpful. 

The night before we went, as I was trying to game plan with her a bit, she mentioned that she did not find either individual in the couple attractive. What? This took me by surprise because the whole point of the weekend was to fuck them. Why would she want to fuck two people she didn’t find attractive? The difference between male and female sexuality really shows up here. She explained that she was really turned on by the idea of the whole thing, and that she didn’t really know how attracted she was going to be to them until she got into the moment because a lot of it is not physical, it’s behavioral (more could be said, but this again shows: girls want you to make a move, so just do it, or want to know if she likes you? There’s only one way to find out). So we just had to roll the dice and see how she felt!

Guys can learn much from the above paragraphs. At the very least, regular readers already realize that girls live in the land of “maybe” and often don’t know what they want. As a man, your job is to find out, and show them the way. Often girls will say no; there are always too few hot, height-weight proportionate and slender girls relative to the number of men who want them. Being in short supply must be fun for those women. But, to the point, who cares? You shouldn’t. Stop living in the “maybe” and make your move, because it may just be that in making it, you’re turning her on and creating an opportunity.

I won’t go into the details of the whole weekend, but suffice it to say everything about the weekend was the same as it would be if you went away on a normal, non-ENM couples weekend. We got tickets to events and all hung out in a very non-sexual way. Went out to dinner, etc etc, with no real, proper flirtation or escalation. This was part of my mistake, as I didn’t feel comfortable escalating without having talked to the dude about it first, and I should have called him before the weekend. So things ended up being pretty tame when it could have been a lot hotter with a lot of sexy banter and flirtation as the day progressed. Even worse, when we finally got back to the house we had rented, I had a small but real medical challenge. 

I usually press the throttle and go, speeding along the highway to the danger zone, revving up the engine and feeling the tension, ready to howl and roar, pushing along the red line into overdrive… but I genuinely wanted to back out at the last minute because it all felt so awkward. We were sitting around in the living room in our underwear all waiting for someone to initiate. There was a combination of fear and shame over not having sorted all this out before, and I was kicking myself for letting it get to this point. Luckily, my indecision was again rescued by two people who had clearly done this before and had a plan. Museum Girl suggested that her partner had brought some shibari rope and could teach me how to tie the girls up. This was a genius idea, for many reasons, but mainly it is on a short list of things that allows for a transition between not sex and sex (this is extremely important for women). Encouraging a girl to spank another girl, and then the guys taking turns on her, is another strategy. Museum Girl’s offer broke the awkward spell of us sitting around the kitchen all hoping someone would take charge and finally gave us all some direction.

One of the biggest problems in the group was that there was a clear difference in dominance between me and Museum Girl’s partner. He was tall but soft spoken, kinda nerdy, and, although he professed to be into kink and a dominant, energetically he was anything but. I try to not make other guys look bad in foursome situations, but he was making it hard. I didn’t want him to be emasculated by me and wanted to create space for him to show up as the most attractive version of himself. I have a tendency to take up a lot of metaphorical space in a conversation and so was trying to tone my personality down and make him more interesting, but up until the rope suggestion I’d come up empty. The minute he got the rope out, he came alive. 

Rope was an area where he felt super confident, and it allowed him to be the teacher and me the student, creating a nice hierarchy where he was in charge. He’d show me how to tie a knot, and then I’d repeat it on my gf. We’d switch and he’d tie up my gf and I’d tie up his. Switching allowed for a nonthreatening venue for the partners to get to know each other with a sexual element before penetrative sex. This was the first time I felt comfortable flirting/escalating with his partner and she responded with a bunch of IOIs. I finally started to come back into my body (out of my head) and feel comfortable, confident, and like we all were on the same page. 

Then Museum Girl (who describes herself as submissive but oddly not in certain respects) took charge again and requested the three of us tie my gf up while she fucked her for a while. She got a bowl of ice and went down on my girlfriend, which got my gf super turned on. Once again, Museum Girl broke the ice on partner swapping creating more safety and freedom for the men to do the same. After a while, I started fucking my gf and we all fucked for a while on the bed side by side. At some point I started making out with Museum Girl while fucking my gf and then eventually we switched partners. 

Sadly, the other dude could not stay hard; I should have offered him Cialis before we started (btw, this is a really common misstep guys make for a number of reasons, but in any new/challenging situation: go ahead and take the Viagra or Cialis–makes everything better for everyone)! Taking Cialis is super common in multi-partner sex situations, and one of the reasons I encourage every guy to take it anytime you’re in a stressful sexual situation. I take it even when I am going to fuck a new girl for the first time (solo), because, again: why have any stress? Part of being a man is heading off problems before they develop. 

I was having a great time fucking Museum Girl and she was loving it, but we both noticed the other two kind of struggling as he had a limp dick. My gf kept trying to join us and eventually it became too awkward and I didn’t want him to feel left out and so sent Museum Girl back to him. 

Afterwards, we all debriefed and I gave him some Cialis and told him that he should always take it and disclosed that I had taken some extra vitamins, so he knew I was juicing. Better living through chemistry. Many apparent woodsmen in sex parties and other ENM situations are on it. Sex parties and non-monogamy have grown in the last decade due to the Internet letting sex-positive people connect with one another, but the presence of  “the juice” helps too! Performance enhancing drugs are so named for a reason! Silicon Valley is built on coffee and tea, yes, but also Modafinil. 

I debriefed with my gf later, and she confessed that she ended up being super turned on by Museum Girl, but she was not attracted to the dude. This is what I had expected and worried about, and I told her that I appreciated that she tried to take one for the team. This did leave us in a bit of a pickle, because I really wanted to keep fucking Museum Girl, especially as a threesome, but they’d made clear they were a package deal. 

Even worse, Museum Girl spent the next day effusing about how much fun she had had and how hard it was to find couples to go away with. She liked us for our bodies AND our minds. We had to let her down hard, unfortunately, and texted her privately to let her know that there was no chemistry between my partner and hers. She was disappointed but understood. It’s all in the game. I bet she’s faced the problem of her partner being unattractive before. The more necessary links there are in a given situation, the greater the number of failure points.

This comes up because I recently reconnected with someone who knew Museum Girl and the other guy. They broke up. She has a few kids now. Life moves on. 

• This is an older foursome story.

• There are many others in the free book.