Love & Sex

How an Awkward Night with One Guy’s Special Curve Got Me Over a Horrible Breakup

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“You didn’t have to deal with three bad dates to reach an orgasm.”

It took months after our final shouting match for me to even consider taking off another man’s pants. Not that there were many options—most boys I knew still thought of me as “Colin’s girlfriend,” and I avoided meeting new men in favor of raw cookie dough and self-pity. My reasoning for becoming a shut-in was simple: If I didn’t wear mascara, then it couldn’t run.

But when the sexless ennui got to be too much, I invested in a vibrator to keep me entertained. The device was so shiny and sleek it looked like an Apple product, and came with a price tag to match. Pink was the only color the store had left, but the cashier convinced me it was the “Bentley of sex toys,” and I was lucky to have one, even if it was magenta.

When I got home, I was $200 poorer, and still didn’t see why a woman would want to shove a luxury car into her vagina. Then I found out.

Almost immediately, the buzzing sound drowned out my thoughts of dying alone. Sure, I usually scheduled sessions between break-up cries, but for a few minutes a day, it seemed I was finally getting myself together. It was easier to find relief in a new toy than a new person—you didn’t have to deal with three bad dates to reach an orgasm.

My roommate Danielle, however, saw right through my “fun.” She said this pleasure was more like procrastination, and urged me to give a sentient being a chance. Since she knew me well, she wasn’t talking about dating—a one-night stand was more likely to jolt me out of my misery. But while she was right, the thought gave me more anxiety than arousal.

In my Montessori school, we had sex ed every year, and learned everyone is a beautiful snowflake, right down to his genitalia. But I hadn’t employed those teachings in the past two years, and was rusty. I’d forgotten the “It’s huge, I swear” look I’d perfected as a slutty teenager, and was far from prepared to hit the hookup scene again.

But Danielle didn’t care whether I was ready. My brooding had taken over our apartment and that made it officially her problem too. She solved it on a Friday as we were getting ready to head to a bar across town. I was applying fake eyelashes when she appeared in my doorway, hands pressed into her hips.

She wasn’t talking about dating—a one-night stand was more likely to jolt me out of my misery.

“You’re having sex with Anderson tonight,” she informed me, stepping into the room to try on a pair of my heels. Anderson was her coworker, a boy I’d once Facebook-stalked and determined to be, “not that bad.” We’d never met, but apparently, that was going to change tonight, whether I liked it or not.

 “He’s meeting us at Casey’s, so wear something tight,” Danielle said, clipping toward her room, still wearing my shoes. “And seriously, take off those eyelashes—if you can’t spot the drag queen in the Irish pub, it’s you.”

When we arrived two hours late, the bar was as Irish as the Lucky Charms mascot, but its worn mahogany gave it a dose of authenticity. Each splinter told the story of a forgotten Friday night, while each graffitied penis told me to mentally prepare.

Though Anderson and I both knew the plan, Danielle went through the formality of introducing us. He was taller than expected, but in an awkward way, like someone had resized his photo and forgotten to hold down the shift key. He wore a white T-shirt, a hoodie, and a smile so weak you could hear his teeth click together for it. Since his physical self didn’t make much of an impression, I focused on a photo I’d seen of him DJing—we could work with that.

Both Danielle and Anderson worked for a recording company that paid more in prestige than dollars, so I had no expectations of him buying me a drink. This was good, because he didn’t. I pretended to enjoy the feminism of ordering myself a Pickleback, and it was worth it—one sip released the tension, like a kegel for my soul.

Our forgettable conversation was outshined by Danielle’s constant how’s-it-going glances. She was worried because she couldn’t sense an attraction between us, but soon realized that we didn’t need one. For both of us, sex was more of an errand: his, an end to a who-knows-how-long dry spell; mine, a box checked off my break-up to-do list. The musty air between us reeked of necessity. But if Anderson didn’t care, neither did I.

I awoke from a short blackout to find a gang of us at IHOP, one boy passed out beside his breakfast combo. It pleased me that, though I had no idea how I’d gotten there, I wasn’t the biggest shit-show in our booth.

The waiter set down a plate of alfredo I didn’t recall ordering, and it looked like something I’d already thrown up. I feigned disgust, but my standards for drunk-eating were comparable to tonight’s standards for sex—if it was in front of me, it was a go.

Anderson continued making eyes at me as I shoveled chunky white calories into my mouth. Danielle looked pleased with our dynamic, knowing that if most men saw me eat, there was no way we could have a sexual future—I often licked my plates clean, and always seemed to have a bit of lettuce stuck in my hair.

But from the nervous way Anderson peered across his pancakes, it was clear he needed tonight as badly as I did. When the check came, we kissed, mixing his maple syrup with my white sauce. Both of us did a good job ignoring how it tasted.

Despite the heels and fake eyelashes strewn across my room, I insisted we head to my place. It was a 30-minute cab ride to Venice, but my vibrator was there—in case of performance emergency, break glass.

We lay on my bed, and my hand crept to his jeans. This was it—the (hopefully) big unveiling. Would it be perfect and pink, like my vibrator, or long and thin, like Anderson? Would it drive like a Bentley, or more like a Jetta? Would it be manual, or automatic?

I tugged off his boxers and cocked my head to the side—something wasn’t right. I knew penises could be slightly curved, but this one came close to a right angle. I wanted to blame Danielle, but she couldn’t have predicted this. Genitals only make sense in hindsight—like first names, people grow to fit them.

Once our foreplay reached the point where Anderson could do no more with my boobs, I knew I was going to have to touch it. I did, and the dent was all I could focus on. It was like holding a weapon from Clue—Anderson with the Lead Pipe on top of my comforter.

Then, I wondered: Maybe a curved penis would be more fun? After all, my vibrator had a slight arc, and this shape resembled a finger stroke I knew I liked. Perhaps Anderson was bent for utility’s sake, like a periscope on top of a submarine.

Testing my theory proved difficult, as the tip and I repelled like two negative magnets, but I eventually swiveled on. No bonus sensation, but I was relieved that things felt relatively normal.

I tugged off his boxers and cocked my head to the side—something wasn’t right. I knew penises could be slightly curved, but this one came close to a right angle.

Almost on cue came a sharp twisting in my lower abdomen—something I’d never experienced before. Anderson’s anatomy was the first suspect, but that didn’t make sense since I couldn’t feel it earlier. I considered cramping might be a physiological response to the night’s meaninglessness, but I’d been so determined to cross a finish line that the idea of needing something more depressed me. I opted for a less personal, yet highly probable excuse—an excuse whose bad Italian seasoning I could still taste.

To convince myself of the alfredo’s culpability, I imagined a worst-case scenario: Globs of partially-digested cream landing on Anderson’s chest, him sprinting out the door, and my vibrator, in some karmic turn, permanently running out of battery.

When I dismounted and faked a yawn, Anderson seemed content just having made it this far. He buckled his belt without a whimper, and I stealthily downed three Motrin before walking him to the door.

As the night air hit our faces, we thanked one another and shared an understanding nod. It was a brief look, lasting only a moment, but our eye contact acknowledged our sex had somehow mattered. It had been confusing, disgusting, and orgasm-free, but it had still, definitely, been sex. We’d both needed it, and we’d done it together.

For the first time in months, I was sharing an intimate moment with someone. And though it didn’t quite hit my G-spot, it still felt great to check the box.

Image via Alan Levine