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Alison Brie shares an especially experimental moment of college experimentation.

I went to art school. Now art school is not like regular college. Tai chi was a required course, we had a circus class taught by a bearded lady, and clothing was optional everywhere but the cafeteria. Similarly, the students there are of a different grain. They’re very deep and introspective, really open to experimentation of any kind, and they have weird haircuts. In my case, the first year there was fraught with exploration. I learned a lot about the inner workings of me. I learned how to become “a clean sheet of paper”; I learned how to breathe through my coccyx; I learned that pretty much anyone would have sex with me. This at first I thought was because I was “so talented” or “so creative.” Later, of course, I realized I was just easy. So I capitalized on it.

Exploring my newfound sexuality, there was, of course, the girl-on-girl action, the crazy threesome with the afros and whips, and the surreal ‘shrooms experience where I thought the tree was fondling me but it turned out to be my creepy male roommate with calluses on his hands… gross. You get the picture. I developed this (possibly misplaced) sexual pride, based solely on the quantity of penetrations of my vagina… and not necessarily the quality of the acts therein.

So one afternoon I’m sitting out on the grass with my overly contemplative, self-hating, gay friend Jon, who’s recently come out of the closet and thinks it’s the worst thing in the world. He hates being gay. He hates that he has to put it in his butt. He hates the creepy art major with the blond comb-over who wants to lay “his poopy wiener” in his mouth. He just hates everything about it. And I feel really bad for my friend. I want to help him. This was, of course, not the first time I’d had to listen to him complain about the hopelessness of his situation, despite the seemingly endless list of available male suitors I’d brought to his attention. I decide it’s time to get to the root of the problem and see exactly what Jon isn’t enjoying about his newfound same-sex sex. So I ask him, “Well, Jonathan, how many guys have you had sex with?”

And he’s, like, “None, ewww.”

I am a bit surprised by that reaction. So I probe deeper. “Oh. Well, how many girls have you had sex with with?”

And he’s like, “None, hello?! Ewww.”

And I think to myself, well, okay, the solution is blatantly clear. Jonathan needs to have sex! With me! Obviously in order to accurately evaluate his sexual preference and come to an informed conclusion, he must explore all viable options. And what if he were to discover he was actually straight? I would have saved him from a life of dysfunctional penetration. Literally my vagina would have been his road to salvation! One can only listen to the despondent rants of a depressed, confused, and sexually ambiguous virgin for so long before one must take action. Plus, who better to show him the ropes than his very own, self-proclaimed captain of coitus, the queen of copulation herself, and not to mention one of his best friends in the whole world?

So I pitch Jon the idea, and though he’s a bit reluctant at first, I really give him the hard sell, and next thing you know we’re both frolicking down to my room to grab the last condom from my sock drawer and then hurry down to his room before the impulse can pass us by.

We get to his room, a plain, ground-floor dorm room — bed, desk, wide-open space, and this big picture window that looks out at the school pool with those slat blinds that are always incomplete, always missing those essential two slats, as his appropriately are. So I close what’s left of the blinds and hop under the covers, he throws on some music and hops in with me, both of us pumping with adrenaline at our own spontaneity, and we’re off! We start making out and… we continue making out… and I tear off my shirt, and I tear off his shirt, and I rip off my shorts, and I pull off his jeans… and I’m starting to notice a pattern forming in regards to one person’s possible involvement more than the other’s. But I choose to ignore it until… I go to put my hands down his undies and he lets out a shriek so loud and so feminine, it’s like nothing I’ve heard in the bedroom before. I pull back, a bit shocked, and ask, “What?”

He’s like, “What’re you doing?!”

I smile, “I’m going to touch your penis…”

He’s like, “No, no no no no no no — I can’t, um… That’s not…”

I’m like, “…oh. Um, do we need to have a talk first about the fundamentals of copulation… or?”

He’s like, “No, no, I can do this, let’s just have a no-hands-below-the-waist rule. For now.”

So, I’m like, “Okay… okay, you know what, it’s weird, yes, but I’m the pro here. I want you to be comfortable, so whatever I can do, it’s okay. You’re in good hands. I know what I’m doing, and I can… not do that for you.”

So we start making out again, and slowly but surely, we get back into it; him awkwardly avoiding my breasts; me sensually stroking his… arms. And, you know, we go on this way for quite some time with no results down below, until finally I’m like, “Is there anything I can do? I mean, are you sure you don’t want to just let me put my mouth on it? Or…” And he’s like, “No, no, I just think I’m not so comfortable, you know, I feel like people outside can see me, I’m just kind of having trouble getting into it.”

Now at this point I probably could have read the subtext here, like, I’m not into this. I’m not really attracted to you at all. ‘Cuz I’m gay. But no, I chose to take this as a plea for further instruction. I mean, I’d tackled problems in the bedroom far more challenging than this and always concluded with a happy ending, so to speak.

So I’m like, “Okay, let’s brainstorm. Maybe if we put the mattress in the closet, we’ll have plenty of privacy.” (I failed to see the irony at the time.) But he’s okay with it, and so the next thing I know, we’re squeezing the mattress onto the floor of this small, dark closet and we get in there and he’s like, “One more thing. I think also you should get stoned. I just think I’ll feel more comfortable if you’re kind of out of it, ya know, so I can like, do my own thing…”

Now this gave me pause. I was suddenly a little worried. I mean, what were the real motives here? Was he going to wait till I was “out of it” and try to wiggle it into my butt? Did he want to dress me like a boy and sodomize me in secret? I momentarily pondered my predicament. Was I losing my erotic edge? Had I finally found an envelope I could not push? No! We had gone too far for me to back down now, and I wasn’t about to let this little fairy destroy my hard-earned sexual legacy; I’ve made out with Mormon chicks, for Christ’s sake! Luckily, I had my affinity for pot on my side, and the idea of free drugs outweighed any long-term insecurity.

So I say, “Sure! Sounds great! Anything you want.”

He’s like, “Great! I’ll go find better music to set the mood!”

So I’m smoking, I get good and high, and he comes back very excited, like, “Oh my God, I found the perfect song: Madonna’s ‘Erotica.'” Now… this may have been another moment that should have inspired hesitation, but actually I was really excited about it, ‘cuz I was stoned, and he was really excited about it. ‘Cuz he’s gay. So he gets in the closet with me — literally and figuratively — and we’re both into it now, like movin’ and touchin’ our… selves. And before we know it, he has liftoff! So he gets the condom on and I get on him and we’re doing it! We’re actually doing it! And we’re into it. That’s right. We grind and bump for a good ten, fifteen seconds when suddenly he grabs me and is like, “Oh my God, oh my God…. The condom broke!” And I get off him, fast. I’m freaking out a bit and I’m like, “Oh my God, what? How do you know?” And he takes it off, examining it, and he’s like, “Well, it’s all wet down there.” I lift my eyes, red and puffy from the pot, defeated and full of shame as I realize… “Oh. Well, that was me.”

So, I guess it’s safe to say that the whole experiment was basically a failure.

You’ll be happy to know that Jon has accepted his homosexuality and hasn’t had sex with a woman since. In fact he called me recently to tell me that he still has nightmares about that fateful day. I take it as a compliment. After all, I may not be able to turn a gay man straight, but I do leave a fellow with an experience he’ll never forget.


Excerpted from Worst Laid Plans: When Bad Sex Happens to Good People.
Copyright © 2010 by Alexandra Lydon and Laura Kindred and reprinted by permission of Abrams Image.

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