Group Sex

It’s possible that the roots of my curiosity about group sex lie within The Big Chill. It was my favorite movie when I was 13 years old—I rented and watched it repeatedly, and it began to form an epic place in my psyche as a representation of contemporary adulthood, a stage of life that as far as I was concerned, couldn’t come soon enough. I’m a Capricorn, so I wanted to be a grown-up from the moment I was born. My first complete sentence was “I love caviar,” which my parents had served for the adults at my 2^nd birthday party. And, whether it was because of my parents’ diplomatic but very definitive divorce when I was five, or an early childhood spent nipping at the heels of their circles of pithy, alcoholic relatives and bohemian friends, or what, but my vision of adulthood did not include me, daddy and baby makes three. That seemed rather lonely and isolated to me. Instead, I imagined something like a co-ed, incestuous family of friends forged in the heady maelstrom of a 1960s University of Michigan, who are brought together years later by the elegiac suicide of one of their group, to spend a weekend in a beautiful Carolina country house making sumptuous meals, doing drugs, having intellectual arguments and fucking one another.

Yeah. That was my shit. It turns out one of my best friends, Sara, was also enthralled with The Big Chill, and we began to conceive of our own Big Chill weekend, to occur at her family summer house in Wisconsin and include two of our other girlfriends and a group of four boys, the members of which changed according to whomever we had a crush on at any given moment. One day, Sara came to school beside herself with excitement: she had asked her parents whether they would actually chaperone us on such a trip, and they said yes! The date was set for May, over three months away. We immediately started a Big Chill notebook, which we passed among the girls, who each wrote fantastical entries of what would happen on this grand weekend in the woods. There was a lot of sex and intrigue in that notebook, although none of us had had sex and I don’t think any of us really planned to. A little making out, or “scamming” as we called it, was what we were conversant in and this was appropriate for our age.

But me, the sophisticate, ever trying to push the envelope, couldn’t wait. One weekend in March, we heard that Matthew Sanger’s parents were out of town and he was going to have a “set,” or party. All of the popular guys were going to be there. I remember Sara was over and I was ironing cloth napkins, a household chore I found oddly satisfying. I made a decision in my head that I then shared with my friend: “Sara, we need to make something important happen in our lives. I propose that tonight, at the party, we suck dick. No one in our grade has done this before. It should be us.” I’m sure Sara was apprehensive—and I was too, although I was acting like deciding to put my mouth on a penis was as natural as ironing cloth napkins. Nevertheless we went to the party, got our other girlfriend Rhys in on the plan, pulled two lucky guys into a bedroom and took turns sucking them off. The penises, and our skills, were underdeveloped, and I know that neither of the guys came—this was new for them, too. But when we emerged from the bedroom, and later from the party, I had such a sense of power and pride in what we had done. And we had accomplished it as a group! We did it, you guys! We sucked dick! And we did it together! But the fallout from our decision was not pleasant—rumors spread around the school like wildfire, and we got reputations not as brave and innovative sexual pioneers but uh… as sluts. And, to add insult to injury, I was dis-invited to the Big Chill weekend by Sara’s parents for corrupting their daughter.

But I never really lost that inclination to “make things happen” or to “conduct experiments” that came from ideas in my mind rather than sensations in my body. I went through more conventional sexual-romantic experiences in late adolescence and early adulthood of having boyfriends, having sex with them, alone, and happily alone, loving them alone, and happily alone. I became what my father is—a serial monogamist—which is a sight better than what my mother is—alone. But I was never really single, never had the experience of playing the field, of being my own agent, since those early days. I had three long-term relationships from the age of 17 on and as the years passed, in the back of my mind I started to wonder, is this it? Only this dick, only these lips? Are the only two relationship choices lifelong monogamy, or serial monogamy? I was determined to never be involved in infidelity, based on secrets and lies, which goes against everything I believe in. But I really couldn’t see how even the happiest couples wouldn’t at some point crave sexual, or even romantic variety. The divorce and adultery rates corroborate this suspicion. What was the matter with me? Was I a swinger? Ew. No. Well… maybe?

Fortunately, I had an ally in no less than my most recent boyfriend, Johnny, one of the most amazing people I have ever known, who to this day is my best friend. As openly communicative as we are, I was really scared to tell him, straight up, that I fantasized about being with other men. Of course I hoped he might be somewhat sympathetic because, unlike me, John is bisexual. And I was right. We began a conversation about opening up our relationship that lasted probably a year before any real action took place.

There was an earlier stage of this opening up, one that I like to call the Fucking Our Friends stage, which proved quickly to be too treacherous for either of us to handle. Turns out The Big Chill was not the ideal model after all. Bummer. We agreed we needed to put some structure on this. We needed to cast out way beyond our immediate, even tertiary circles. We needed to find the other open-minded freaks out there, and fuck them, and let them fuck us. In the same room? Maybe. Apart? Well, let’s just see who we’re dealing with here.

So that’s how we came to be members of the Lifestyle Lounge. Who knows what Lifestyle Lounge is? OK. Well, for those who don’t know, it’s a social networking website for swingers. It’s pretty amazing, actually. I recommend it to anyone who has a curiosity about this sort of thing. The interface is cheesier looking than Myspace and it costs $20 bucks a month, but if you want to enter a different, fascinating world where what’s up is down, where all these little pockets of our upstanding citizenry—all social classes, all races, all creeds—are making arrangements and celebrating the right to suck and fuck thy neighbor’s wife, and thy neighbor’s husband, or both at once—Lifestyle Lounge is the place.

It is important to know that the swinging lifestyle revolves around couples. The average couple on LL is in their mid forties, more physically fit than you will ever be, more tan than you will ever be, waxed to the gills—waxed all up in the gills, you might say… maybe a tit job, maybe a bleached anus. You know. And yeah, they like fucking all different kinds of folks in different kinds of ways. But other than that, they are totally normal. Like, completely fucking normal. Like, condo owning, “professional,” Range Rover driving, Trader Joe’s shopping normal. Well, maybe that isn’t so normal. But I guess I was expecting some more scenester young people and friendly hippies up on there. And the weirdest thing of all is that these couples, for the most part, are leading a double life. Their friends, their coworkers, their families—the “vanilla world” as the swingers like to refer to it—know nothing of their exploits. The hot threeway with some bisexual chick they picked up at a bar. The seven people pile-up out in the suburbs a few months ago. The trip to Hedo last spring. Ahh, Hedo… For a community based on sexual freedom, it’s sad to me that so many swingers are still in the closet. But there they are, locked in this duality of being that is not unlike adultery. They are having an affair with themselves. Crate and Barrel days, ass-to-mouth nights.

The other important thing to know is that the main forms of fucking these couples are looking for is either a threeway with an experienced bisexual woman, or swapping with a complementary couple. Single people get in where they fit it, the bisexual woman being primo top choice. Single men, or SMs, in Lifestyle parlance, are the least popular, and often treated by the couples like chattel or expendable drones in the beehive of group sex. However, this has created something of a buyer’s market for the minority of women and couples who want to invite different men into the bedroom.

After some fits and starts, we met Chris. He was 36, lived in Albany Park and managed a hip record store in Lakeview. Intellectually and physically he was our peer. We had a couple of hot threesomes, and then Johnny decided to go to Europe for a few months to work on a book. With Johnny’s blessing, Chris and I continued a nice little relationship of sorts, and I almost forgot that the reason we met in the first place was swinging. Chris started asking me if I was interested in this girlfriend of his or that, and what if she brought a guy over one night, and I realized, oh yeah, he wants to have a foursome. Oh, okay. Sure, I was game.

We made a date for a couple weeks later. This other girl Chris was sleeping with named Maria and some guy whose name I don’t remember showed up with a 12-pack of Stella and we sat around the kitchen nervously sucking down our beers and cigarettes. I think this was a first for all of us but Chris, who clearly enjoyed being the organizer and leader like the Leo he is. I sized the newcomers up and decided that, especially if I had a couple more beers, I could definitely have sexual relations with them—even Maria (I had never been with a woman before). I started to get excited. We retired to the living room. Chris and I started making out on the couch. Someone came from behind me and encircled my waist, their hand on my throat. I looked up to see other dude’s face looming in for a kiss. I made out with him for a minute. OK kisser, not great. I turned back around to see Maria and Chris making out beside me, shedding their shirts. Maria straddled me, pushing me back down on the couch. “You’re really pretty,” she breathed. “You look like Dita von Teese.” I’ve heard this before, but it’s a nice compliment. We started kissing, then expertly removed each other’s bras. The boobs were the best part: I have boobs, you have boobs. I’m touching your boobs, you’re touching mine. Other than that, making out with a girl for the first time was a dissociated experience for me. This is nothing against Maria, an attractive and experienced bisexual girl. But when I was kissing her, it just felt like I was kissing disembodied lips. I tried to give myself a thrill, to tell myself, you’re making out with a girl, isn’t this amazing?! But, it kind of wasn’t. Not bad, not good, just… not real feeling. I’m going to have to make out with a few more girls before I close the casebook on my sexual orientation, but I think it’s fairly safe to say that I’m straight. And being a straight girl does not bode well in the swinging world.

After these appetizers, we moved on to the main course. Chris and I were fucking on the couch and Maria and dude were doing stuff on the rug below. Chris sensed trouble with the other couple, and suggested a switcheroo. After about five minutes with dude on the floor, I figured out what the trouble was. Performance anxiety. He could not get a hard-on for his life. I’m a good sport, and I know this is a very sensitive, if not the most sensitive issue for men in the bedroom, and I really tried my best to arouse him, gently, slowly, with understanding and patience. But try as I might, an erection was not going to happen, and I wanted a break anyway. I offered to go get us some beers and we sat back on the rug in front of the fire to watch the Chris and Maria show.

Now this I was really curious to see. Besides the whole frisson of seeing my lover in action with another person, Chris had told me specifically that sex with Maria was different—that she liked a little rough play and domination from her partner. It was interesting to see how indeed, the sex was rougher than the sex Chris and I had, with him slamming repeatedly into her and her making low, growling little animal noises that crescendoed into loud, guttural come cries. In fact, for a second I thought she might be crying. And then, suddenly, out of fucking nowhere, as he reached his own climax, Chris spit directly on Maria’s face.

Whoa. That was a surprise. Frankly, I was disgusted. But Maria didn’t seem to mind and like I said, I was trying to be polite and a good sport. I started to clap, nudging other dude to join me. “Bravo!” I said. “Let’s smoke a joint.”

The post-coital of a group sex experience is probably my favorite part. It’s the closest to my beatnik commune fantasies as I’ve gotten. We sat around nude, blankets wrapped around us, passing around the joint and talking of this and that. In spite of our differences and our difficulties, we had made a foursome happen. And we did it together. I was proud of us, and told the group as much. We clinked beer bottles, and then Chris and I went to the bedroom, leaving Maria and dude to camp out in the living room.

When we woke up the next morning, they were gone. Chris talked to Maria on the phone later and apparently after we went to bed, dude was hard as a rock and ready to go, but came in like two minutes, leaving Maria unsatisfied. The next morning, he blamed her for introducing him to us depraved individuals, and damn right he couldn’t get an erection, that was the weirdest shit he had ever been a part of. “Seriously?” I said. “That sucks. I thought dude was pretty nice and smart, and I didn’t really care that he couldn’t get hard. But he called us weird and depraved, and dissed Maria? What the fuck? Why would he do a thing like that? What is wrong with people?”

Chris shook his head. “Because he is being an insecure dude!” He sighed, looked and me, smiled, shook his head again. “Jess, I like you and you’re really smart and everything but when it comes to certain things… kid, you’ve got a ways to go.”

By Jessica Riddle