[Read Part 1 and Part 2.]

Glenn: Wherein I assess the titular friendship, in particular its humble beginnings and its evolution into something that was temporarily very gratifying.

My friendship with Glenn (that’s what I’m calling him; it’s not his actual name) began on Twitter, where my wife and I encountered him for the first time a decade ago or longer. He and his wife shared an account, though she seldom used it; for a very long time whenever we would interact, it would be with him rather than with her or with both of them.

Glenn and his wife – Susie? Samantha? Shannon? I use a lot of “S” names to refer to women I cannot actually identify due to privacy issues, so I think I’ll call her Alexandra. Anyway, Glenn and Alexandra were swingers. They didn’t identify as polyamorous; it was very clear that they were fans of sport-fucking without any pesky emotions. And for years, Glenn was a big proponent of the four of us hooking up. Yes, he was attracted to my wife – why wouldn’t he be? – but it was pretty clear that his priority was watching me fuck his.

As Glenn and Alexandra weren’t local, I thought little of his overtures. He’d shown me a couple pictures of his wife and I found her attractive, but as I hadn’t interacted with her at that point, and in fact had no idea whether she was even aware of his machinations, she held little tangible appeal for me. Though I’m not and never have been demisexual, I do prefer to know what somebody is about before I have sex with them, or at least to talk to them a bit and get a sense of whether they are even into me.

A year or two later, I interacted with his wife for the first time. I noticed her commenting on my sexy tweets with enthusiasm, and eventually we took the conversation private via Twitter DM. Our interactions were often intensely erotic in nature. I found her sweet and sexy, though reserved. I looked forward to occasional communication with her – her reservations lessened the more we talked – and I felt excited by the prospect of getting to know her and maybe even meeting. Time passed, and by 2015 a meeting between the four of us seemed a foregone conclusion.

The first meeting of many occurred in 2016. While passing through their city on the way home following a week-long road trip, the four of us met for a very enjoyable breakfast loaded with fun and flirty conversation, genuine excitement, and surprising feelings of connection. When we left the restaurant after four hours, Glenn and Alexandra invited us back to their place for a four-way. It was our first time doing same-room full-swap, and a great time was had by all. By the time Jill and I left their house and continued on our way, we were about nine hours behind schedule, but neither of us had cause to complain.

My wife was very interested in Glenn, and the feeling was mutual. Before we left their house that evening, they indicated they’d be open to seeing us again; we saw them three more times in 2016 alone. We swapped, of course, and even paired off and spent the night together in separate locations (Alexandra and I at our hotel, Glenn and Jill at Glenn and Alexandra’s house). We took day trips and did fun family-friendly stuff. Our kids became friends. Between visits, we stayed in touch, often sending flirty messages and sexy pictures.

During the fourth and final trip we took to see them that year, Glenn told Jill that he didn’t have the same feelings for her that his wife had for me, and vice versa. In other words, while he enjoyed having sex with her, he was unable to reciprocate her emotions. She was hurt; beyond the rejection she undoubtedly felt, there was surely a modicum of envy for the connection I had made. At the time it seemed that Glenn had let her down in the most earnest, ethical way imaginable. We all remained friends, and the eventual cessation of our annual summer road trips to their city was due only to COVID.

I enjoyed Glenn’s progressive values. Sociopolitically and socioeconomically, he leaned far left. Perhaps even farther than I did, in fact. He had a great sense of humor, and was sex positive, not obsessed with cars, and barely interested in sports if at all. This meant that I didn’t have to fake interest in football any given Sunday that we happened to be visiting. He was an unabashed geek, a die-hard fan of Lord of the Rings, Doctor Who, and Star Wars among countless other pop culture properties. This was someone I was fine watching fuck my wife, or for that matter having join me in fucking her. He was the first guy whose balls touched mine.

Around him I didn’t feel uncomfortable or inadequate despite his greater stature, his unwavering confidence, and frankly, his bigger cock. Above all, I didn’t worry that this man was going to turn out to be a problematic creep because it just didn’t seem possible. He supported my relationship with Alexandra, at one point gifting her a trip to California to spend a few days with me in a hotel. In retrospect his consistent encouragement may have blinded me to various red flags.

Despite my confidence to the contrary as demonstrated in the previous post, this makes me wonder if sex does motivate my friendships after all. Am I more likely to accept a guy as a friend if doing so provides me with some sort of sexual perk? Most guys I’ve known would not encourage a sexual relationship between me and their significant others, and if they did it’s unlikely that said significant others would be interested anyway. But what if they did? Would I be more likely to embrace a guy whose friendship brought with it the occasional three- or four-way?

Once again, I don’t really think that’s true. I don’t care what kind of perk you offer – free concert tickets, a twenty percent discount at Target, weekend barbecues at your rustic mountaintop home overlooking the San Francisco Bay – if you’re a MAGA hat-wearing racist who thinks women exist to breed, or for that matter a self-important corporate douchebag who excels primarily because of his privilege, kindly go fuck yourself.

Still, it doesn’t hurt to check in with oneself from time to time and re-assess. Make sure that your heart is in the right place and your motivations are as pure as they can possibly be. At the very least, I feel like really lousy people – the worst of the worst – rarely if ever bother to introspect.

In the next post I’ll explore one particular episode in our friendship that should have clued me in to the fact that all was not as healthy and functional as it first appeared. And would have clued me in if I was capable of seeing clearly, i.e. if there was sufficient blood flowing to my brain.

Continued in Part 4.