Save an Uber, Ride a Cowboy is a column exploring queer millennial sex culture. The stories presented here are based on true events. Identities have been changed to protect the privacy and reputation of those involved.
“Gay men are not meant to be monogamous,” Caleb said staring at Riley.
“What?”
“I think a benefit of being queer is not conforming to heteronormative relationship molds.”
They kissed.
Riley pulled away, “I’m not mounting you on a park bench.” It was close to midnight, and he didn’t want to be that tacky duo grinding on each other in a public park—not to mention the ingrained fear that some passerby would see two boys kissing and decide to do something not so nice.
But tongue trumps reason so Riley straddled Caleb.
They decided to go somewhere more private, in this case Caleb’s questionably legal co-op a few miles away. An abandoned warehouse he and his roommates re-purposed into makeshift apartments, complete with a scattering of tarps and half-full paint buckets. As a result of climbing rent, young kids working shitty day jobs had to become increasingly creative.
Caleb went to the restroom, during which Riley snapped a few photos on his phone. Evidence, because this place looked like a spot where someone might reenact that Silence of the Lambs scene. But he figured he was safe since Caleb’s hands were moisturized.
It was summertime, which meant inside it was sweltering. Since essentially every apartment building in Brooklyn is old, they lack aspects of modernity — like AC. Leaving suffocatingly hot rooms relieved only by cracked window or a P.C. Richard plug-in fan, sometimes two.
Caleb’s “room” was no exception. Riley was looking at his mattress on the floor and wondered how the sheets would look with their bodies’ sweat stains when Caleb offered, “Want to go on the roof? It’ll be cooler.” The mechanics of a rooftop hookup alluded Riley, but to the bead of sweat forming on his brow, open air sound positively erotic.
As they ascended the crumbling stairs, Riley contemplated turning back. There’s plenty of dick in New York City, he thought, dick that lives in foundationally-sound homes. Then he was hit with the view: a borderless stretch of roofing that looked if you walked over the edge, you’d step clean across the East River into the Manhattan skyline.
On the other side of the roof was a brick chimney, whose edges and crevices were adorned with different potted plants. “You have a garden!” Riley squealed, left a little breathless by the greenery’s audacity to exist within such industrial harshness.
He turned back to find Caleb swaying on a metal swing next to the roof’s entry way. The mechanics of the hookup were beginning to become more clear.
“Dude, I love you roof,” but Caleb was done talking, and pulled Riley onto his lap. Murderer or not, Caleb was a good kisser. And what’s better, he seemed to really like it, couldn’t get enough of it. You’d think this would be a given, but in the world of casual sex where, for most, the goal is penetration, many are quick to move their lips lower than your mouth after delivering a few obligational pecks.
The creaking of the swing’s rusted metal was eventually drowned by the pair’s heavy breathing, when Caleb broke for air to ask, “Do you like to be spanked?”
“I’ve never tried it.”
“Bend over.” Like they were in some sort of domination vid, Caleb positioned Riley on all fours across his lap; the swing squeaked furiously.
First the cool air tickled Riley’s (at this point) bare ass, followed then by a firm smack from Caleb’s outstretched palm. Riley normally liked it when his partners took charge, but Caleb, with his slight frame and boyish face evoked more substitute teacher than dominator. Riley stifled a giggle and was beginning to lose his boner.
Thankfully, Caleb was not, and after their brief misstep, they got back on track and soon found themselves off the bench, onto the floor of the roof groping, sucking… The roof was probably dirty, but neither of them seemed to notice. Funny how practical thoughts evade you when a cock’s in your mouth.
Riley wanted to see Caleb finish first, it was one of his kinks: watching someone’s breath quicken, abs constrict, face twitch, body vibrate, and know it was you who gave them that pleasure.
But when Caleb got close, rather than let Riley bring him to completion, he started jerking off. Watching him tug away manically made Riley feel a little obsolete. Wanting in on the action, he quite literally tried to lend a hand, but Caleb pushed it away. From a foot away, Riley watched from his knees as Caleb’s body tensed and fertilized the dingy rooftop.
“That was hot,” Riley lied, still recovering from the coldness of Caleb’s shove, but determined to finish strong. He was touching himself, hoping for Caleb to join in.
A long moment passed between them. Surely he isn’t going to make me ask, thought Riley, who up until this point had never had to ask someone to return the favor. He conceded after more deafening silence, “Aren’t you going to help me cum?”
Caleb gave a helpless smirk, “but I came.”
Riley blinked at him.
“Sorry, I’m just not horny after I cum.”
Standing there naked with dick in hand, he searched Caleb’s eyes for a sign of malice or contempt, but only found honesty. Which somehow made it worse.
They began to retrieve their clothes, retracing the steps of their encounter. Riley tried to stay turned away from Caleb to hide his red cheeks. They didn’t say anything until something in the way Riley aggressively pulled up his jeans prompted Caleb to ask, “Are you annoyed?”
Riley wanted to say that no one was horny after they orgasm, but they got their partner off anyway because they wanted to make them feel good. He wanted to say that sex should be viewed as a mutually beneficial, a fucking symbiosis, not two people separately using one another to achieve their private goals. But all that internal dialogue sank into the growing pit in his stomach: an emptiness borne from the moment when anger subsides to sadness.
“No, I’m not annoyed.”
Caleb walked him down the neglected stairs. “Do you want to sleep over? You can.” Riley shook his head. Caleb pulled him close for a final kiss, deceivingly tender. “Thanks, I had fun.”
It was either very late or very early, the sun having yet to rise, Brooklyn a cast of shadows and faint traffic murmurs. The kiss lingered with Riley for a few blocks, a disorientingly intimate touch to a night that felt anything but.
Walks of shame normally filled Riley with a sort of immature excitement, a march of sexual independence that he’d looked forward to since his virginal years. Usually he’d float along enjoying the momentary peace of mind that comes with being wanted by another. But Riley was feeling less desired and more like an exciting substitute to a night alone with some lotion and a palm.
He hadn’t gone into it necessarily thinking he’d want to see Caleb after tonight, but since when did casual sex denote being an asshole? Riley was reminded of all his friends’ stories of men’s callous bedside manners. “They’re just shit humans,” he’d assure them, and come morning he knew he’d pity Caleb for his limiting sexual outlook, but right now it was hard to shake feeling like a mode of someone else’s satisfaction. Rather than stew in his insecurity, Riley decided to call an old friend who he knew would still be awake at 4AM.
Paloma’s buoyant voice came on the line, and his heart somersaulted. She listened and concluded, “Fuck him, he sounds like a shit person. Side note, I think I’m in love.”
Paloma was famously scatterbrained. A reliable wild card, too charming to be considered a total mess, she and Riley had partied away much of high school together. Although always popular with boys, she was never eager to be tied down, so this confession came as quite a surprise. It was even more shocking when she started to cry, “But he’s leaving the country.”
Paloma never cried, not even during their very bad shrooms trip junior year.Â
Thoughts of Caleb felt very far away as Riley consoled her over the phone. Paloma felt all these feelings. Having given so much of herself away to this guy, she was devastated at the prospect of him leaving. While his heart went out to his friend, part of Riley couldn’t help being soothed by her groans. It was awful of him, he knew, but he felt a selfish comfort in that he’d only given away one night and chance to cum to Caleb.
Bodegas were starting to open, their owners sleepily peeling up the gates. In the early morning, love sounded awfully complicated. “Babe, that sucks, but I’m sure you’ll meet somebody else,” he told himself as much as her.
Riley quickened his pace, spurred on by the prospect of a hot shower and his own bed, empty as it was, he knew it wouldn’t make him cry in the twilight hours. Besides, he could always make himself cum.