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.
“Do you want anything?” Fratboy asked Riley.
“Nah, I’m good.”
6AM on New Year’s Day in a McDonald’s somewhere on the Upper East Side with sweaty hair and cum still drying on his torso, Riley tried to process the past few hours as Fratboy ordered his second XL diet coke of the night.
It wasn’t so much the twilight hour or unceremonious post-hookup behavior that needed processing… these were fairly routine for Riley, whose sex life had not quite evolved into the glamorous spectacle Sex and the City had promised — although, it should be noted that Fratboy did have a bed frame, an upgrade from the usual mattress on the floor. Less routine was Fratboy’s supposed heterosexuality, which was only divulged after Fratboy’s first and very premature orgasm.
* * * *
Riley hadn’t been particularly eager to ring in the New Year with a stranger, but after the countdown had finished, the combo of booze and a need for touch made Fratboy’s Tinder profile start to look more promising. The stranger had a cute face and since his bio didn’t read “never been with man,” Riley figured he could do a lot worse.
So he began a (cis male) queer pre-date ritual: selecting a crop top, choosing an earring, and contorting oneself on the bathroom floor to insert an enema — because nothing makes you feel beautiful like flushing your anal cavity before a seduction.
Once Riley felt confidently clean (or as confident as one can feel when ass play is imminent), he did as generations of Brooklynites did before him: hopped on an uptown train in pursuit of getting laid.
As he emerged from the subway station, he was greeted by the January cold and the characteristic silence of the Upper West Side (even the holiday couldn’t shake the affluent neighborhood’s mode of restraint). Like a thrift store rat trapped in Saks Fifth Ave., Riley fiddled with the broken clips of his faux fur jacket while his earring twisted in the breeze.
He walked a few blocks to find Fratboy waiting on the stoop of his apartment building. A lost social nicety that caused Riley to be more nervous than appreciative. Niceties were out  —  didn’t Fratboy know? Millennial dating isn’t bogged down by gendered normatives like modesty or chivalry. Instead, today’s dating is a competition of casualness, a game of dodging texts and making plans to “hang.” Mere seconds into meeting, Fratboy had already thrown off the equilibrium.
In hindsight, there had been a lot of clues that Fratboy was straight.
For one, he was a lot fitter in person than his Instagram initially led Riley to believe. Straight men, radical in their lack of fucks given about crafting a social media persona, are not preoccupied with aesthetic and angles. In short, they dare to take front-facing photographs. Oh, and he was also wearing a Grateful Dead t-shirt.
“What’s up?” asked Riley.
“Not much, just got back from a Phish concert at Madison Square.”
Straight.
Riley took a moment to recover. “How was it?” Fratboy bobbed his head enthusiastically and replied, “Dope. I’ve actually seen them two nights in a row.”
Flaming hetero.
They went upstairs and began the pre-coital dance. Where are you from? What brings you to the city? Have we mutually decided that we’ve made enough small talk to get on with it? Turns out Fratboy went to school in the Midwest and was being groomed to become the next president of his university’s top (he emphasized this distinction) fraternity, and that was about all Riley could gather before he dived in.
Fratboy was a shit kisser, but there’s an oddball charm to shit kissers, Riley thought, a rhythmic puzzle that, when solved, will reward both parties with a make-out sesh for the books. Plus Fratboy had a taut torso, so Riley tongued on.
Then came the hands. At first clumsy, then awkward, Riley guessed they were more a product of the late hour rather than a reflection of Fratboy’s sexual prowess. But as Riley straddled him, something felt markedly off.
Fratboy was holding his middle, several inches above his hips. Perspective has since supplied Riley with the answers. Fratboy was used to wider, female hips. While they kissed, his arm wrapped dramatically around Riley’s head. Because Fratboy was used to keeping longer, female hair from falling in his face.
Yet the real zinger was the early climax.
Now, reader, there is no inherent shame in a premature ejaculation. In fact, for those whose self-esteem is volatile at best, a premature ejaculation from time to time can serve as a much needed confidence boost. However, there is cumming fast — and then there’s cumming fast. Lips around cock and few bobs up and down was all it took for Fratboy to tense and grunt, signaling that round one had promptly ended. It was then, through the clarity that only comes post-orgasm, that Riley pieced it together. Phish, the fraternity, the uncertain hands…
“Don’t take this the wrong way, but have you ever been with another man before?”
Fratboy shook his head. Round two followed promptly, because nothing is hotter than honesty.
Round two served more as a cultural experiment, a chance for Riley to play out the title of Pornhub video: Fraternity Bro Digs First Gay Blowjob. 15min 24sec. 3/5 stars  —  and to see if all those sexual stereotypes about hetero guys in the bedroom were true.Â
They were.
With a sense of entitlement only institutional masculinity can breed, Fratboy lied back with his arms behind his head while Riley was at work. During a breather, Riley asked him if there was anything he wanted to try during his first time touching another man. “This,” Fratboy responded after Riley repeated the question three times, finally utilizing those communication skills heterosexual men are so well known for.
They didn’t fuck. Partly because Riley didn’t think Fratboy was entirely ready for the complexities of male-on-male anal sex, but mostly because there was no lube. Not eager to get another hemorrhoid, Riley took a moment to mourn the minutes wasted cleaning his ass then returned to sucking dick.
In a move that broke script with the PornHub mode of operation, Fratboy returned the head. He kept this up for a minute before resorting to a gruff, tensely-fisted handjob.
* * * *
After Riley’s first and the Phish enthusiast’s second cum, Riley became acutely aware that he was in bed with a straight guy. Afraid that Fratboy, now no longer driven by lust, would be angry with him for initiating him into a new kind of brotherhood, Riley addressed the pussy-loving elephant in the room before Fratboy could.
“But you’ve been with girls and enjoyed it?”
“Yes.”
“And you’ve had sex to completion with girls?”
“Yes.”
“Am I asking too many questions?”
“I’m an open book.”
And he was. In a refreshingly reverse narrative, Fratboy seemed at ease — satisfied even, with no apparent societal guilt weighing on him. He told Riley that while he’s always been attracted to women, he noticed two years ago that maybe his attraction might also extend to his own gender. So he decided to do something about it.
“That’s brave,” said Riley, hugging his knees to his chest.
Maybe for Fratboy getting off was just getting off. Even so, Riley couldn’t help but admire his attitude. How many people have gone their entire lives suppressing sexual desire, opting for normalcy over sexual truth? Not Fratboy, for here he was, in the most intimidating of cities, taking matters into his own hands, clumsy as they were.
Fratboy blinked at the queer boy in pink H&M briefs who was lying in his bed. Riley met his gaze, searching for a change, a shift, or something profound. But that’s not life and that’s not sex. It’s not always out of body experiences or aha moments; sometimes you’re very much in your body, confused and fumbling, and you don’t necessarily come out the other side wiser for it.
“My sister is going to wake up for work soon, but we have a minute to chill,” said Fratboy. Apparently this was her apartment.
“And she doesn’t know anything about you…?”
“No.”
“So I should go.”
“Well, we have a second — ”
Riley began finding his clothes, not eager to be part of a coming out skit at 5:30 in the morning. Fratboy seemed discouraged, “But I’ll walk out with you. I could go for a diet coke.”
The McDonald’s employees didn’t give the two disheveled boys a second glance as they waltzed into the establishment in the twilight hour. Then again, who is more seasoned in the varieties of humanity than a 24-hour McDonald’s employee?
After they talked for a bit and Fratboy had quenched his thirst, Riley thought it best to begin the return journey to his borough. His presence was due at the restaurant in only a few hours. They walked together to Riley’s train. How does one say goodbye to a straight man? A kiss seems presumptuous, a hug too affectionate. Fratboy settled for a thank you and a stiff wave. He sent Riley a text later in the night, but Riley had already fallen asleep.
At work the next day, Vanilla Ice yelled at Riley. Apparently he had not delivered the celebrity-customer service the 90’s one-hit-wonder thought was appropriate. Riley apologized, but struggled to contain his giggles at the server’s station as he fetched Mr. Ice’s hot coffee. His coworkers asked him what was so funny. Nothing, he told them, it just really was a new year.
Original artwork by Scott Walker.Â