Darling Dre

Darling Dre

I knew the tourist wanted to fuck me as soon as she attempted to order a glass of wine from my shitty dive. Bartender crushes were inevitable—someone’s always projecting their desires at me.

It never mattered how aloof I was. And it made no difference how brusquely I explained to her that this wasn’t the type of bar with more than one generic bottle in stock. The blond was clearly smitten with the idea of me, playfully expressing disappointment in “settling” for the Pinot Grigio.

“I usually like my wine tall, dark, and handsome,” her eyes glowed in the dim light. I inhaled and braced for her to complete her clumsy metaphor. “But since you’re pouring it, I think that counts.”

Even the schlubbiest bartenders get shameless solicitations when their patrons are properly lubricated; fucking a bartender topped so many bucket lists. My mere existence as a six-foot-two dude who can make a simple old-fashioned bumps me higher on a stranger’s “fuck-it” list even though I have to be the least horny bachelor in Brooklyn. Rolling my eyes would hurt tips, so over the years, I’ve conditioned myself to chuckle as if amused. I excelled at pivoting conversations to ordering another round and then conveniently becoming too busy pouring drinks to chit-chat. It was usually easier to deflect than tell them that in the rainbow spectrum of sexuality, I was mostly gray.

But tonight’s shift was a slower-than-normal Thursday, which led to me riding a hotel elevator with a strange woman fondling the zipper on my jeans. She claimed to be in town from Detroit for a weekend of bachelorette duties and found herself drinking alone at my bar before everyone else got to town. She emitted suburban energy and her transience in town made me more willing to accept her invitation for a “tour” of the new Downtown Brooklyn boutique hotel where she was staying. Why not trade some half-hearted intimacy for a first-hand look inside the new gentrified phallus that was erected to tower over the skyline?

Erected. God, I’m a twelve-year-old.

As the elevator climbed to the 30th floor, I couldn’t help but sigh and hope the lady working the hotel front desk understood that I was an invited guest, there for consensual sex. The teenage memory of my dad warning me about being alone in a room with a woman bubbled up. No matter the circumstance, I would always be the sex-crazed aggressor, if she claimed any impropriety.

The tourist introduced herself when she first ordered wine, but I instantly forgot her name. Bad bartender. When she pressed me for my name, my reflexes were too dull and I told her the truth.

“I’m Dre,” I said. Usually I claim to be “Jay” or “Chris,” a reliable stock name for a generic Black guy. Very inoffensive and monosyllabic, so I wouldn’t accidentally stray from it after heavy drinking. It was perfectly nondescript so a web search would turn up nothing about my identity.

Of course she paid for her drinks in cash, preventing me from gleaning her name from a credit card. I didn’t have the heart to make things awkward later by asking her to reintroduce herself. Maybe it was Jeannine? Or Janie? Possibly Jeannie, because the bar was so loud when she said it. I learned long ago not to test my memory out loud if unprovoked, and honestly, she wasn’t going to quiz me anyway.

Just smile, nod, and suppress my internal monologue. Fortunately “Jeannine” did most of the talking, allowing me to space out a few times. All of her bachelorette talk reminded me how much fun it would be to plan my own wedding blowout. It’d be an open bar rager with a live band doing punk meets hip-hop covers of wedding soundtrack cliches. The Electric Slide would be so lit that the moshing would look like a coordinated music video: aunties dropping it low to the bass, while my COGIC cousins throw up metal fingers. I’d be an awesome groom, if only I dated.

Inevitably, my drifting attention would snap back to reality, like the elastic in a fresh thong, because Jeannine would say something egregious. Over the course of the night, she found several excuses to mention how Black guys were always staring at her ass.

“A woman who doesn’t skip leg day at the gym would make most people colorblind,” I droned, trying not to sound annoyed. She probably thought she was being subtle. The assumption was that I had been clocking her curves (or should’ve been). But really, I never think of sex organs when I meet someone. I winked, pretending I was caught with lustful eyes, instead of just an ambivalent gaze. I hated myself for playing to her ego but hated being stiffed on the tip at the end of the night much more. I’ve never really given thought to the ethics of sleeping with someone after they’ve tipped me in cash for pouring drinks. This was the first time.

The hotel elevator was outfitted with a spinning disco ball and strobe lights. Tacky. Speakers in the ceiling blared Michael Jackson’s “Don’t Stop Til You Get Enough” and there was so much auditory and visual noise that the security camera probably wouldn’t detect Jeannine cupping my balls through denim. I’d barely served her two glasses of vinegared wine before she commanded me to come with her for a blowjob. I guess the bourbons I poured for myself put me in the mood for compliance. Since college, I had averaged one sexual encounter every four years and I guess I was overdue: Jeannine was pretty, direct, and seemed nice enough for me to break my dry spell.

The elevator door slid open and Jeannine pecked my lips like a starved pigeon. She grabbed my hand, leading me down a neon-drenched hallway toward her room. I allowed myself to be pulled by the tourist but couldn’t resist swiveling my head back for one last glance at the elevator’s shimmering disco ball before the door closed. My easiest route of retreat was now gone. Before my eyes could adjust to the hazy violet glow of mood lighting in the hallway, I walked right into Jeannine who had halted in front of room 30B.

“Oops,” she giggled as she intentionally dropped her room key on the ground. It was more performative than an NBA player flopping to the ground to force a free throw. She folded herself to pick the key card up, poking my crotch with her butt. Weirdo.

I laughed, remembering a cumbersome lap dance I got in Vegas while a song by an early 2000’s nu-metal band provided the soundtrack. I don’t know whether the stripper was less aroused than me at that moment, but I sort of shrugged my shoulders and went with the cringe. Those moments always made for a funny story where I could later make myself the butt of the joke. It’s why sex was always more interesting to me in theory than in actual practice. It’s awkward as fuck.

Jeannine finally opened the door to her hotel room and pushed me inside, where I stumbled two steps and crashed onto the bed. By the time she tugged my pants from ass to ankles and planted a condom in my hand, I had seen everything. The room was much smaller than the shoebox I call my studio apartment, and my curiosity was immediately sated by its cramped benignness. The digital clock on the bedside table displayed 3:09am. The only interesting thing in the whole expensive-assed place was a zebra-striped paint job, which I couldn’t look away from while I fumbled with the condom. I always had a hard time figuring out which side of the rubber was right. Maybe it was the adrenaline and how quickly everything was moving, but my blood had mercifully rushed downward and “little Dre” was hard.

Jeannine arched her back and dug her knees into the base of the bed, motioning for me to enter her from behind. As I inched myself in, she aggressively slapped her own ass before I could start pumping.

“Yeah!” she yelled. “Spit on it daddy!”

Eek. I’d seen fairly vanilla porn and was a little dumbfounded. Did she want me to spit on her? Or maybe my dick? I definitely had no fluency in dirty talk and usually relied on muscle memory to kick in during these encounters. My brain usually let me dissociate till it was all over. I hadn’t had sex in years; who knows what new sexual norms had emerged since then.

Please don’t think that I’m one of those porn-addicted, incel losers. During college I got it in a bunch: girls, guys, groups. Everyone was always so sex obsessed, so I sort of had to give it all the college try. Reassurance that I wasn’t missing something. I guess I could’ve kept on fucking, but by graduation I was confident that I didn’t have an ounce of kink in me. Sexually, I was a boring-ass straight line drawn in invisible ink.

“Punish me daddy!” Jeannine moaned loudly, reaching back and swiping at my left quad. I think she was serious. I know some people find an ass slap sexy, but I thought better of hitting some random White lady I wouldn’t recognize in a week. I wanted to go home. “Fuck me harder!”

“Ma’am,” I thought. “I’ve barely moved my hips.”

I looked down. The majority of my dick hadn’t entered Jeannine and I hesitated to push it in. My tongue felt too big for my teeth. And dry. Maybe I should’ve downed a glass of water before closing the bar?

My eyes traced the stripes in the wallpaper and I slowly started to thrust. I returned my gaze to my flexed abs, straining to recognize the outline of a six pack under a layer of flesh enhanced by all the brown liquor I skimmed at work.

“Fuck me, Dre!” she screamed. As I pumped, I scanned the room for her phone. I needed to make sure she wasn’t secretly recording me for some sort of X-rated gotcha show. My poor penis was now semi-erect; the bottom section bunched up at the base and expanded like an accordion as my pelvis tepidly smacked against her ass cheeks.

“You love this white pussy?!” the tourist yelled, more a statement than a question.

I really wished she would pipe down. I’m sure the hotel guests on the other side of the wall were listening and snickering to themselves.

“Yes, Dre! Fuck me! Tag your name on my ass!” she hollered. What did that even mean? I exhaled and wished I was home playing Nintendo.

At least the tourist would be busy with a bridal shower in the following days and I would never have to see her again. No worries about her attempting to exchange phone numbers or social media handles when we were done. Usually I lied and said that I wasn’t on social networking sites.

“Does that feel good?” I asked, filling time by trying to act engaged in my half-assed gyrations. I ignored Jeannine’s affirmations and tried to remember if I needed to pick up soy milk on the way home, because lactose intolerance is real. My corner bodega had recently started stocking almond milk, which apparently contains fewer calories. Maybe a milk switch would help my abs resurface?

As my mind started to wander to oat milk, a premonition of Jeannine drunkenly invading my Saturday shift at the bar with a bunch of rowdy bridesmaids stole my breath. My imagination was suddenly inflamed by a gang of blondes wearing matching t-shirts and loudly shrieking around the jukebox. The locals would be so pissed at the tourists that they’d drop a buck on the counter as an annoyed tip and bounce, leaving me alone with the bridal party. If not Jeannine, one of them—maybe the bride—would make jokes about hooking up with me in the bathroom. I’d have to give them free shots. My heart rate spiked, pounding much faster and harder than my lower torso had been doing with Jeannine.

The digital clock in my eyeline displayed 3:16am. Time for me to force myself to moan, “Fuuuuck.”

“Yeah daddy, you like this little bitch?” she shouted. “Fuck me with your big, Black co–”

“Uuuughhhhh,” I interrupted the tourist with a fake seizure, sending my weight onto her.

I’d seen that happen in movies.

She mimicked me, collapsing onto the bed beneath me. We froze like two starfish superglued together. I counted to twenty and then rolled over, pulling the condom off. It only took three steps from the bed for me to flush the rubber down the toilet before Jeannine could take a look at it. This wasn’t the first time I’d faked an orgasm.

“That was great,” I lied while zipping my pants. I tapped my foot beneath the bed in search of my belt, like a blind person’s white cane, making sure not to break eye contact. Pretending to appear earnest always went a long way in moments like this and also worked especially well at the bar. I just had to be careful not to send any signals that I was up for a sleepover. “Thanks for your hospitality!”

“Oh yeah, that was fun!” her contribution to my lie. “I’ll be walking crooked tomorrow.”

I mumbled best wishes for the weekend of bachelorette festivities, thanked Jeannine one last time, and softly closed the door behind me to commence the walk-of-shame to the elevator. It didn’t matter whether I had any actual sexual prowess. Time and confirmation bias would solidify Jeannine’s description of me as the virile stud that I’ve never been. The hallway glowed with its poseur-neon. As I trudged down the hallway, an anonymous gaze from behind each peephole followed me. With all the noise Jeannine made, the hotel guests were definitely awakened by the sound of their mandingo fantasies being affirmed.

Jokes on them.

I chuckled as I waited for the elevator with its disco ball to take me back down to earth. I had almond milk to pick up. Cereal and video games would provide the only nightcap I ever truly lusted after.



About the Author

DL Dawson (not his real name) is a journalist and television producer living in Brooklyn, NY. His work as a journalist has appeared in the LA Times Magazine, Salon, the TODAY Show, ABC’s Nightline, BET, and the CBS Evening News


Photo by Pylyp Sukhenko on Unsplash