All The Times I Failed To Have A Threesome
In some ways, it's more aggravating that I came so close to having a threesome. If it had never been a possibility, then I might never have cared. But to fly so close to the threesome sun, and then to fail, to fall... well, it makes me feel like Icarus.
As you get older, the chances of taking part in certain activities diminish. For example, when I was a kid, I wanted to become either a fireman, an airline pilot, or a garbageman (weirdly enough). But now that I’m old(er), my window for becoming any of these things has closed. I’ve simply waited too long to train as a fire/ garbageman/ pilot. It’s just never going to happen.
In the same way, it seems like I’m never going to have a threesome. I’m too old and lame and out of shape now. It’s sad. No group sex for me. I got close to having a threesome many times (very, very close), but as the saying goes, “close only counts in horseshoes and hand grenades.” This is debatedly true, but one thing is for sure — “close” definitely doesn’t count for threesomes.
In some ways, it’s more aggravating that I came so close to having a threesome. If it had never been a possibility, then I might never have cared. But to fly so close to the threesome sun, and then to fail, to fall… well, it makes me feel like Icarus.
Anyway, at least you can savor the bitter stench of my failure. (Which makes no sense. Why would you want to savor a bitter stench? But whatever.) Here are all the times I failed to have a threesome.
1. Age 21 — Post-college failure. I’m dating an extremely annoying art student named Melissa. Over spring break, her even more annoying friend Ashley comes to visit from South Carolina. The only thing I remember about Ashley is that her parents were very very rich, and that her dad had bought her two cars — a black car to drive during the day and a white car to drive at night… which remains one of the dumbest things that I have ever heard.
Ashley, Melissa and I all get stoned, and Ashley expresses a willingness to partake in what the French call a ménage à trois. Melissa expresses a readiness to take part in this activity. Unfortunately, I can’t reply, because I’m stoned for the first time in my life — I’m too paranoid even to mutter the words “I have the munchies.” Eventually, I go and hide in the other room, and the threesome moment quickly withers and fades.
2. Age 23 — Stripper failure. I’ve moved to a different college town in the South, and am now dating a bisexual stripper girl named Stephanie. How many times in life do you get to date a bisexual stripper? Well, for me, this will be the one and only time. After six months or so, I decide to take advantage of this opportunity. One night in our local bar, I nudge Stephanie on the shoulder: “Hey,” I say, “you should invite that girl home with us.” I point to a brown-haired chick in a miniskirt. Stunningly, Steph agrees to do this, and even more stunningly, it seems to work. The girl doesn’t leave with us, but she does agree to meet us later on at our apartment.
Giddy with success, Steph and I exit the bar. Cut to us sitting at home. Two hours have passed. The chick is never going to come. Why, oh why did she lie to us like that?
Then there’s a knock on the door. Stephanie and I shoot each other identical petrified looks. Oh shit no she did come after all. In an instant, we both realize that we have not mentally prepared for a threesome. Both of us were counting on the fact that it would never ever happen. “You answer the door,” we whisper. “No, you.”
Steph answers the door, and lo, the brown-haired girl has a guy with her. Without our knowledge, the threesome has been upgraded to a foursome. Oh god no way. Also, the girl is all of a sudden wearing a cowboy hat, and she looks significantly older than she did in the dim light of the bar — kind of leathery-skinned, even.
What happens is this: All four of us just make awkward small-talk and end up drinking beers and watching TV. “The English Patient” is playing on Cinemax. It’s an excruciating movie to watch with two drunken horny strangers. Also, the movie is like four hours long. Also, it sucks. At the end of the movie, the British chick dies in a cave, and Juliette Binoche finds redemption. We turn the TV off. The strangers depart. No three-or-foursome happens.
3. Age 26 — Grad school failure. I’m living in New York with my grad school roommate, Jeremy. One day, Jeremy’s friend Diana announces to him that she wants to have sex with both Jeremy and myself. The J-man and myself are both pretty excited about the prospect, until we start to realize that we don’t even like walking around in front of each other in boxer shorts, and the whole thing starts to fizzle out from this moment.
The thing about this girl is, she wants the two of us to pretend to be her professors, and her to be the student. My roommate and I decide that it would be funny to have her come over dressed up as a schoolgirl, while the two of us sit behind a desk and use desiccated English accents, saying stuff like — “Miss… Jones. Professor Miller… and I… have detected a certain flaccidity in your treatment… of T. S. Eliot’s later… work. For example, in paragraph three, you completely… overstate the importance of Le Mot Juste, while ignoring the fact that of course Eliot placed nearly all of his… attention on the Objective… Correlative. Well. I’m afraid that we’re going to have a very… long night in front of us, Miss… Jones. I’m afraid that we must demand a complete… rewrite…” – and then just sort of drone on and on like that for two hours.
…Of course, what ends up happening is that we spend all of our time coming up with jokes like this, while never actually getting around to having the threesome. So, there is that. My theory the whole time is that Diana is secretly in love with Jeremy, and is just using the threesome as an excuse to get closer to him. But when I run into Diana a year later, I ask her about this, and she says, “No, I just really wanted to have sex with you two guys.” Oh. Great. Good to know.
4. Age 30 — Orgy failure. I drive six fucking hours from D.C. to New York in order to have a proposed orgy with my fuck-buddy Amy, my old roommate Jeremy, and Jeremy’s ex-dominatrix, ex-foot-fetish-model girlfriend Lucia (who are in an open relationship), plus Amy’s roommate, and Amy’s roommate’s fiancee (who are also in an open relationship). …Whew!
I have the following compressed conversation with Jeremy as I am driving up to New York — Me: “So we’re clear on the ‘not having anal sex with each other and not touching or even really looking at each other’ part of this orgy… We’re clear on all of that, yeah?” Jeremy: “Crystal.”
During the drive up I also become super-paranoid and start driving really slowly; thinking that I’m going to crash my car or that someone’s going to crash into me, because I’m thinking, “No way is God going to let me have group-sex for the first time in my life. No way no way no WAY. He’ll stop me or kill me first or something.” …But as it turns out, I don’t have to worry about any of these things; anal sex with Jeremy or God. Lucia has to leave early to go to a dance recital, the roommate’s fiancee doesn’t show up, which means the roommate can’t partake in sex, and the whole thing just turns into a disastrous failure, just like everything else in my life, sigh. And that was my last chance ever at a threesome or group sex or whatever.
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So what have I learned from all this? Well, here’s what I’ve learned. Organizing group sex is like organizing any sort of group activity — i.e., it’s kind of a pain in the ass. Like, if it’s just you and your girlfriend trying to do dinner and a movie on a Friday night, odds are you can manage to arrange that pretty quickly. But if three or four or six people get involved, then there start to be debates over Thai versus Mexican food, and some people only want to see an action movie while other people want to see a romantic comedy and, arrrgh, forget it. …And that’s the whole problem with group sex; there’s just too many damn people involved. 
