The Best Time I Accidentally Attended a Teenage Orgy

by Ashley Cardiff

I was a pretty late bloomer when it came to boys. Most girls in my hometown started holding hands in third or fourth grade, kissing in fifth or sixth, dry humping — as teens are wont to do — by eighth. But, because it was a small town, most of the kids with whom you attended kindergarten ended up right alongside you as you graduated, and if you’d forged an elementary school reputation as chubby and unlikeable, it was pretty hard to shake.

I ended up getting my first kiss at 15, when I went to visit a friend in rural Maine and got to be the exciting new girl for a few weeks. I was Californian and blond enough, and everyone was impressed at how I wore sunglasses even when it was overcast. That first kiss came from a young aspiring pharmacist who was a foot shorter than me and had tricked out his car to look like KITT from Knight Rider. He was a nice guy. My second kiss was from an older boy with a devilock, so that’s one I can be proud of.

My slow development was further stymied by homeschooling, which I’d taken up in seventh grade for reasons that are neither relevant nor terribly interesting. The point is: that year, I ended up in a charter school program that had me taking classes at the local community college, which was terrifying after years of studying alone.

I was socially inept and uninterested in dating of any kind until the first day of my sociology course, when this guy walked in and obliterated all solitary impulses: he was wolfishly handsome with straight black hair cut in a perfect rock ’n roll shag. He also dressed like a sexually aggressive 11-year-old at a mall goth store in baggy jeans and bowling shirts, and of course he had a wallet chain — but teenage hormones make a person discard not just reason but taste as well.

I stared at this guy throughout that entire first class, in disbelief of his cheekbones, and my infatuation persisted even when he spoke for the first time, when our urbane German sociology professor answered someone’s stupid question about evolution, and mentioned, offhand, the lemur.

“Oh yeah!” the beautiful one interjected. “Like aye-ayes.”

“Pardon me?” said the professor.

“Oh, yes, like those aye-aye things in Madagascar. Natives kill them because they think they’re demons.”

In retrospect, this interaction revealed nothing, but at the time I sat there in class drawing hearts on my notepad as my own swelled with thoughts of He likes animals!

In this way, teenage girls have no survival skills and are unequipped for the world.

For the rest of the semester, I’d stare at him longingly through class and think of him around the clock despite knowing I’d never work up the confidence to speak to him myself. Or to anyone. I knew no one in the class and spoke to no one on campus. I’d show up, attend my classes, go home and quietly do my homework. Every day.

As the semester progressed, I noticed a few of the more sexually advanced girls (all of them 19 or 20) would talk to him after class. To this day, I always get kind of jealous of women who can sit on desks and make it look so insouciant and enticing and effortless and it’s exactly thoughts like these that make me the sort of person who cannot sit insouciantly on a fucking desk.

One such girl ended up sitting next to me in class one day. A few minutes before class began, I took off my sunglasses and slid them into their case. She caught the designer logo labeled inside and looked at me startled, as if the weird, unlikable lump of matter beside her had suddenly become sentient. Little did she know I’d gotten them from an outlet mall.

“Great glasses,” she said in that slow, contralto, drawn-out way that advanced teenage girls do so well. “I’m looking for a new pair. I lost mine over spring break.”

I was really frightened that this girl was talking to me, because she wore hoop earrings and tight pants. I looked at her with wide eyes and she must have interpreted this as awe, because she continued.

“Yeah, I was down in TJ, partying like a rock star.”

“Oh,” I said and I had absolutely no idea where that was. (Tangentially, I did not crack the code that LA and Los Angeles were the same place until high school.)

“Yeah,” she said and grinned coyly. “My nose still hurts.”

“Did you fall on it?”

She paused for a moment and looked at me, unsure. Then she laughed. “You’re funny. What’s your name?”

Her name was Tiffany. Before long, she started sitting next to me in class and asking me questions about homework. Soon after, some of her other attractive friends started to sit in little satellite formations around us. They were all cooler and older and sexually experienced and carried themselves as such. I was waiting for them to figure out I was 16 and a virgin and slept with the lights on. Or that I maintained a scrapbook filled with pictures of my favorite action figures. Or that I drew portraits of myself eating spaghetti with Dostoevsky, one noodle strung between our lips like in Lady and the Tramp. Or that I was wearing Batman underwear from the little boys’ section of JC Penney. Or that I’d spent my last two months’ worth of Saturday nights making a suit of chain mail.

Another day after class, Tiffany came up to me and asked what I was doing later that night. I told her I didn’t have any plans and she said some of her friends from class were organizing a study session at her place. The midterm was about two weeks off and our professor’s tests were notoriously hard, so I agreed.

She motioned to the tall, beautiful teenage boy. “We’re going to study with him.”

I tried not to show the thrill in my spine and shrugged. “Cool,” I said. Just like in the movies!

“It’ll be really fun,” Tiffany continued, “four girls and one guy,” and it was here she offered an exaggerated, cartoonish wink. She gave me directions to her place and told me to show up around eight, which I thought was pretty late to start studying, but I figured she was so popular she must have lots of social engagements to attend after school or had to buy more hoop earrings and cutoffs.

“It’ll be really fun,” Tiffany continued, “four girls and one guy.”

I went home and ritualistically showered, slathered myself in the nicest moisturizers I owned and meticulously obscured my face in cosmetics. I made a bunch of flash cards from the text we’d been studying because I figured men were impressed by fastidiousness. Then I sat back and stared at the ceiling and wondered what it would be like to finally talk to him. I told my parents where I was off to and left half an hour before eight because I am chronically early to everything. I figured that punctuality, in addition to prim organization, would make me irresistible.

I was the first one at Tiffany’s apartment, which was the kind of space you fantasize about when you’re a teenager living with your parents: a windowless basement in someone else’s house with low ceilings and no stove. She let me in and asked if I’d like some Turkish coffee, which I found supremely exotic.

I cataloged every object in her apartment, awed at her independent adulthood, one in which you cooked things on a hot plate and had a print of Starry Night taped to your wall. All other decorative art in Tiffany’s place came in the form of — I’m serious — framed vanity shots of herself. One whole wall was just a bunch of black-and-white headshots, arty portraits, candid photos of her smiling with her eyes closed or being held up in a bikini on the beach by a row of ripped, interchangeable dudes. There was even a painting of her with a sheet slipping down to reveal her breasts. She came over to me looking at all the photos and handed me an espresso cup.

“I used to model,” she said.

I was so out of my league.

“Why’d you stop?”

“They kept telling me my legs were too long.”

I nodded with intense admiration.

“They want girls to look perfect but not, you know, like too perfect,” she said and shrugged with all the wisdom and experience one could have in life.

Even with an age difference of just three years, she seemed infinitely older than me. I wanted her to teach me to be like her. I wanted to sleep on a mattress on the floor in a windowless basement and demonstrate my cursory knowledge of art history and decorate with glamour shots of myself and steal perfume from the mall. I wanted to have to walk through someone else’s living room to take a shower. And then.

“So,” she said, looking contemplatively at one of the photos of herself as I wondered at the vastness of her thoughts, “let me take your bag.”

I handed her my backpack, weighed down with textbooks and flash cards and binders and even a stapler, because you never know.

She looked confused. “Did you bring toys?”

I looked at her and recalled that our entire interaction since the beginning had been a delicate series of facial expressions indicating I knew what she was talking about when I absolutely did not. I considered for a moment and concluded there was no way to fake this one. “Pardon?”
“Yeah,” she said as if it were obvious. “Vibrators, dildos, anal beads, handcuffs?”

“. . . What?”

She grinned from ear to ear. “I told you we were going to study with that guy from class. You didn’t think I meant we were going to actually, like, read textbooks, right?”

“No! No, of course not,” I said, by which I meant, I’ve never even seen my own vagina. I laughed extra long to buy some time. I could hear my heart beating between my ears. They were going to have sex with him! All at once! With me. The only thing more terrifying than losing your virginity in front of older, hotter people seemed like being the prude who declines the orgy because it’s a school night. What the fuck was I going to do? I fumbled. I worried. Time was running out. I laughed again, feigning more nervousness. “. . . I’ve just never used hand- cuffs.” Oh, me.

She lit up. “We’ll fix that. They can be really fun. So,” she held up the backpack again, “did you bring anything?”

I nodded frantically. “Yeah, totally. I have, like . . . four . . . anal beads in there.”

She looked confused, lifting the bulging pack and shaking it, trying to determine how it could be so heavy.

I nodded urgently. “They’re huge.”

Her eyes widened. “Kinky,” she said with the kind of witless, automatic approval of the unfathomable that had been my de facto response for the entirety of our time together. It was then her phone began to ring and she walked off. “That’s probably the other girls.”

By myself for the moment, the panic really set in. I had no idea how I was going to get out of this without seeming relentlessly prudish and un-fun and therefore, worse still, un-fuckable. Not to mention, at that age I watched porn only because I thought it was hilarious, had never masturbated and thought you could get an orgasm from kissing.

Then, of course, the boy showed up. She was on the phone and let him in. He came over to where I was and introduced himself. When I touched his hand I felt like my vital organs were all shutting down in unison. He was so much taller than me. He set his backpack down and it landed heavily. There was hope for me yet.

“What’d you bring?” I asked.

He looked at me oddly and said, “The textbook?”

“Me, too!” I blurted.

“. . . Cool,” he said, nodding. He went to sit down. I turned my attention to Tiffany’s phone conversation going on in the kitchen.

“What do you mean you can’t get it?” she was saying. “We need like a gram. I don’t fucking care what his deal is.” Her face crinkled. “Then go get some more.”

There I was in the basement with my knees bent so my head didn’t touch the ceiling, wondering how I was going to talk my way out of this weeknight teenage orgy and the four supposedly enormous anal beads in my backpack without sounding like the child I absolutely was. Some sort of rash flaring up out of nowhere? No, that would ruin future sexual appeal. I didn’t have any condoms! No, that didn’t seem to deter teenagers any from fucking. It’s not like they teach you to prepare for this. Hours before I’d been making flash cards about social stratification and then bam! The boy I’ve loved from afar for months is going to handcuff me and take my virginity in a moldy basement while a former model watches beneath a frayed poster of Starry Night.

I looked around and saw him sitting quietly, staring off into space, and the room seemed to go quiet and I realized the only way out of this was to tell the truth. If he didn’t like me anymore because I was a socially inept, frightened virgin who didn’t want to have group sex with him, then we just weren’t meant to be. I was going to tell them the truth and if that was embarrassing or objectionable to them, then they could fuck off and I was more than happy to go home right then and complete the best damn suit of chain mail Wine Country had ever seen. So I stood up and started to shake.

“I’m really sorry,” I began.

He looked at me, uncertain.

If he didn’t like me anymore because I was a socially inept, frightened virgin who didn’t want to have group sex with him, then we just weren’t meant to be.

“Motherfucker!” Tiffany shouted. She stormed into the living room and said, “Their fucking car just broke down and the fucking dealer is getting paranoid. I need to go bail these bitches out, so you guys have to go. Let’s take a rain check.”

It was like my fever broke. I grabbed my backpack and dashed out the front door without saying goodbye to either of them. I made it to the Volvo my mother had loaned me for the night, trying to unlock the driver’s side door as fast as possible. I dropped the keys in the dirt, shouted a stream of expletives and knelt down to find them. While I frantically searched, Tiffany hurried outside and drove away. He came outside, too. He went to his own car, stopped, walked back around and stood over me.

“What’s with you?” he asked.

“They were going to have sex with you,” I said, now more anguished by the missing car keys than anything that had transpired before.

“Those girls?”

“Yeah. They said it was going to be a study session but I guess that means an orgy. How am I supposed to know that? I’m a homeschooler.”

I found the keys just as he walked back to his car and sat down on the hood. I stood up and, for some reason, had the idea to walk over to him.

“I kind of thought that’s what was going on,” he said, “but you can never be too careful, so I brought the textbook and a box of condoms.”

I sat down next to him. “I guess that’s pretty smart.”

“Community college girls are all about the dick,” he said. I thought he, too, sounded very worldly.

I sighed and shrugged and at this point, the whole harrowing ordeal had subsided and my nerves were left to fray and I had no more will to fret about my desirableness. “I wouldn’t know.”

He squinted at me. “You’re weird. How old are you?”

“Not old enough for this.”

He laughed and I lit a cigarette and he made fun of me for not being old enough for that, either. We sat on the hood of his car for a while and talked about all the things we had in common, which were actually very few. But having just one TV show you both watched growing up, or reading the same book and liking it: it seems like all the intimacy in the universe when you’re 16.

At the time I was proud of myself for being ready to stick to my guns and turn down a group sex encounter with the best-looking person I’d ever seen. And for a while my self-control seemed to work out for me: the boy and I became friends. Six months later, we started dating. I eventually lost my virginity to him on a twin bed in a filthy house he shared with an obsessive-compulsive 45-year-old Scientologist who refused to throw away newspapers. I remember looking up at the ceiling as the Internet radio “chill” drum and bass played. I had no idea I was about to be in the worst relationship of my life.

Photos via skyturtle, stephenvance/flickr.

Ashley Cardiff is a writer living in Brooklyn. Her first book, Night Terrors, is a collection of essays about sex and dating. You can follow her on Twitter here, if you want.