Grindr Roulette: A Drama in Three Acts

Trick 1: 4:50 pm

I’m sitting in S’mac in the East Village on a Monday night. There’s a small cast-iron skillet of macaroni and cheese before me. Chunks of ham stud the creamy pasta; steam still rises from the surface. It’s a cold day out, and I’m indulging in an early dinner. I’d rather be at home right now, feet up on my ottoman, heat cranked. But, grudgingly, I’ve hauled myself into Manhattan for a meeting this evening.

Are you sure we can meet? I’d texted the group’s leader earlier. I mean, is the building even open on a federal holiday?

Sure! he’d texted back. They’re always open.

I’m peppering the mac and cheese when my phone buzzes on the little cafe table beside me. It’s the group’s leader. No meeting tonight, he says. The building’s closed because of the federal holiday.

Well. Shit. Usually I like being proven right, you know? On a frigid winter day though, with the New York City wind blasting to the bone at every intersection, I was kind of kicking myself for not calling the Center myself from home, before my commute.

There are worse things than being at loose ends in the metropolis, though. So I close out my messages and fire up Grindr just long enough for it to register my location. Then I go back to my meal.

I’m three-quarters of the way through my skillet when I fire up Grindr again. Sure enough, I’ve gotten about eight responses. A couple are just taps from blank profiles—those I ignore. A couple more are from good-looking boys, but their one-word inquiry of Looking?? put me off. I might be looking, but I’d like a little more interaction than that.

There’s a message from a guy who’s a mere 250 feet away, though. In his forties. All I can see in his profile is a chest shot, but it’s a hot chest shot. The dude takes care of himself. Furry bod. Firm pecs. Trim waist. You look close and I need breeding, he says. Any other pics?

When I reply I’ve got some for swap, he immediately returns a photo of his face. It looks like the kind of head shots actors take in for their auditions . . . and if this fellow isn’t quite leading man material, he’s at least studly enough to be cast as the guy the female protagonist in a rom-com uses for rebound sex to make her ex jealous. You know the type. Handsome, in a bland way.

I send him back a couple of dick shots. Fuck, he writes. You’re hung! How soon can you be here?
Ten minutes? I say, looking at the remnants of my meal and guessing how long it would take to walk 250 feet. It’s 4:50

Sounds fucking hot. You got me so boned here. See you in 10, buddy. He gives me an address.

All right, then. I’m going to enjoy this one, I can tell. Hot guy, hot ass, needs breeding, is only a quick walk away. What could go wrong?

Ten minutes might’ve been an overestimation, I realize when I look up the guy’s address on my phone. He’s all of two blocks away, down Second Avenue and around the corner. I stall a little buy prolonging the last few forkfuls of the macaroni. Once I’ve popped a couple of mints in my mouth, I kill a little more time by bussing my table and taking a quick piss in the restroom.

I walk up to the address the guy gave me at exactly 5:00. I find his apartment number on the list next to the intercom and ring the bell. There’s a pause, and then the intercom speaker clicks. “Uh,” says a staticky voice. “This is kind of embarrassing. But . . . oh fuck. Just come on up.” The latch vibrates.

I let myself in and climb three flights to the guy’s apartment. This is the oddest reception I’ve ever gotten. Do I know the guy and not realize it? Does he recognize my secret superhero Breeder identity? What’s embarrassing, and why did he seem to be considering not letting me in at all? (Wasn’t that what he had implied over the intercom?) Had he catfished me? Was the photo he’d sent not his own?

The door opens the moment I knock. I hadn’t been catfished. The guy’s face was the same as in the photo he’d shared; he’s wearing only a pair of loose sweatpants, and standing there shirtless with an abashed expression on his face. But he makes no effort to gesture me inside. If anything, he plants himself against the half-open door and stands there as if to impede me from crossing the threshold.

“Like I said, this is kind of embarrassing,” he says without preface. “I really wanted a breeding, but your pics were so hot that I . . . kind of . . . finished myself while I was waiting for you.”

It takes a moment for the words to sink in. “It’s been only ten minutes,” I finally say, each word leaden. The spark of excitement in my groin extinguishes.

“Yeah, but you know how it is.”

No. I really don’t know how it is to make a date with a guy for a hot fuck and then to masturbate so furiously that I’m spent before he arrives mere minutes later. I blink at him with incomprehension.

“Anyway, sorry. Maybe next time?”

“Uh-huh,” is all I can say.


Trick 2: 5:35 pm

I’m in a coffee shop up Second Avenue, closer to 14th Street, nursing my wounds with a latte that tastes vaguely of gingerbread in one sip, coconut milk the next. And I’ve got Grindr fired up again.
I’m getting messages on a regular basis; the guys on the grid are closest to me in mere tens of feet rather than the hundreds I get at home. You look like the kind of top I need right now, writes one guy. I’m ass-up in my apartment, cleaned out, and ready for your load, if you’re interested.

My disappointed dick is definitely interested. This guy is in his early forties. He’s got a professorial appearance about him. Something about the unkempt curly salt-and-pepper hair in his profile photo, his wire-rimmed glasses, his half-closed eyes, speaks of years of working toward some lowly tenure position. The fact that he writes in complete sentences with proper punctuation, on Grindr, nails home the impression. I could be interested, I type back. If this interests you.

I send him a dick pic. I have one photo I privately call The Deal-Clincher. It’s a self-shot of me reclining on my bed, legs spread, dick in hand, my head drawn slightly back, my brow furrowed, my mouth drawn into a perfect O. In the shot I look close to shooting, and simultaneously insanely smug—a little bit like I’m going to say either Oh my fucking god, this fucker’s about to blow!, or else, Oh shit, is this not the biggest dick you’ve ever seen in your life? I tend more to the latter, because in this particular shot my weapon looks like a fucking baseball bat. It’s so engorged that it’s purple. It fills up my hands. It looks like horse cock. I’ve got a lot of attractive shots of my meat to send out, but when I bust out The Deal-Clincher, it’s because I mean business.

What kind of idiot would NOT be interested in that monster? is his reply.

With satisfaction, I think to myself, Right?

His address is a little further north and closer to Union Square. I swig down the rest of my brew and start the trudge up that way. I’m feeling good about this one; the first guy was just an anomaly, I tell myself.

The guy buzzes me into his building and I take the elevator up the ninth floor. He’s naked when he opens the door, though the darkness of the hallway beyond keeps me from seeing much of his body. In the studio apartment beyond I can see bookshelves around two of the walls, crammed with volumes. Yeah, this guy’s an academic, all right.

Not until my backpack has hit the floor and I’ve kicked off my shoes does he step into the light to reveal the dark coils of hair covering his lean body, the hipbones jutting out at angles below his waist, his unusually large feet. “Thanks for making this so easy,” he says to me, standing on tiptoe to press his mouth against mine.

I reciprocate by leaning down to meet him. He purses his lips and projects the tip of his tongue through the tight embouchure. With the rapidity of a sewing machine, he thrusts it in and out of my mouth.

Oh dear.

Not every guy is a good kisser, I realize. But who the hell is teaching guys to make out like this? That protruding tongue business is about as erotic as a lights-out party with your own maiden aunt. I abandon any attempts at passion and allow him to guide me to the bed. He hops up onto the mattress on all fours and assumes the position. “Fuck it,” he demands.

No foreplay, I guess. No sucking of my dick, no sexy undressing, no attempts to get me hard and ready. Nothing. I guess I’m just there to perform. So I unbuckle my belt, undo the button of my jeans, tug down my pants and shorts, and rub his hole while I masturbate myself to stiffness.

“Oh fuck yes, babe,” he hisses, when my fingers stretch his hole. He’s already wet; it feels more like silicone lube than some other guy’s seed, though. “Get me ready. Get that big penis out and stick it in. Give your baby your big penis. Me wants it. Me wants it.”

His sex chatter is unerotic, but I’ve worked miracles with much less. My dick’s not exactly the overstimulated proportions it reached in that Deal-Clincher photo, but it’s hard enough to fuck. I add a little lube to it from the dispenser by the bed and slide in.

“Fuck that pussy!” yells the guy. “Fuck it! Fuck it! Fuck that—aaaaaah!”

I have a vague idea of what’s going on from the sounds he’s making. Sure enough, when I pull out to look, the asshole has sprayed a load directly onto the bedspread. I don’t know whether he assumes that I’m done, too, because in order to see what’s going on, I’ve pulled out. Immediately he bounces up, though, and starts to pull on some around-the-apartment duds that are lying in a crumpled pile by the bed. “That was great!” he enthuses. “See ya round!”

I’d been in the dude for all of fifteen seconds. If that. Silently, I stuff my junk into my shorts, pull up my jeans, and fasten my belt. He’s standing by his front door, obviously itching for me to leave. Truth to tell, I’m no less anxious to get out, either.

It’s while I’m sitting down on a stool, next to where I removed my shoes, trying to unlace them and stuff my feet in and lace them back up again in that awkward silence, that I take a glance at his books. I see some titles that look familiar to me. “Hey,” I say, genuinely surprised. “You’re a Patrick Dennis fan.” I reach out and touch a spine. “First Lady? No one has First Lady. You’ve got Genius . . . 3D, Tony . . . Wow. You’re a real enthusiast, aren’t you?” I’m a little surprised; other than Auntie Mame, no one reads Patrick Dennis any more (and mostly they haven’t read him . . . they’ve seen the movie).

He was a major influence on my own writing style and outlook. What wouldn’t I give to have a really good conversation about one of my favorite authors with someone else who enjoys his novels? I’d even forgive bad sex for that.

I stand up, hoping for some response. But the guy just shrugs. “Sure. I guess.”

Okay then. I don my coat, grab my backpack, and head out once again.


Trick 3: 6:15 pm

Smart New Yorkers keep two databases in their heads. One is an ever-evolving list of clean and reliable public restrooms at places that aren’t named Starbucks. The other is a compendium of public spots, again not named Starbucks, where it’s possible to sit down and relax between appointments . . . or unsuccessful Grindr hookups.

The Barnes and Noble just north of Union Square sits on both lists. It’s right in the vicinity of the disappointing academic. The fourth floor has a section of seat for lectures and readings that’s fairly reliable . . . and there’s a clean restroom only a floor down. Propped in one of the end seats with my jacket on my lap and my backpack at my feet, I cross my legs and consider what to do.

I’ve had two disappointments so far. Realistically, I should just cut short my losses. Call it a night. Spend the next couple of hours shopping, or grabbing a drink at one of my favorite bars. It’d make sense to head over to Uniqlo and shop for some socks I need. What I shouldn’t do is fire up Grindr again. I’d just land another dud of an encounter. My dick probably smells like the academic’s ass. What if I did get a bite, and the guy went down on me, and came up gagging? What if, after two disappointments, I couldn’t even get it up? Nah. A third go at Grindr isn’t for me.

I’m on the app thirty seconds later, of course.

Hey. It’s a 20 year old. That’s all I know about him, because his profile photo is a starry sky.

Hey, I write back.

Looking to suck big cock. You got big cock for me?

Along with the message he sends a naked photo of his entire self. He’s a skinny little twink with a skinny little butt, smooth from neck to foot. He’s got sloppy brown hair and a fringe of scruff on his chin. In other words, he’s incredibly fuckable.

Yeah. I’ve got big cock. The kid’s given me a boner in the middle of B&N. In retaliation, I unleash the biggest weapon in my Grindr arsenal: The Deal-Clincher.

I want it in my throat. You want to come over?

I should say no. I know I should.

Give me an address, I say instead.

He send me a location a couple of blocks away, on Sixth and 17th. Be there in 10, I tell him.

I’ve got business in the restroom before I leave, though. I grab a handful of paper towels, run some lukewarm water over them, and in one of the stalls I clean up my dick as best I can. It doesn’t look dirty, but I feel a little bit better about shoving it in some kid’s mouth after it’s been in another man’s hole . . . albeit oh-so-briefly.

The walk’s not far, but it’s dark now, and the wind blows in my face like it’s determined to make a particularly icy point. I’m glad the lobby of the kid’s apartment building is stuffy and overheated, because I get a chance to thaw out a little on the elevator up.

The kid opens up the door on my first knock. He holds up a finger to his lips before I can say hello, then reaches out a hand and pulls me into the dark foyer. “Hi,” he whispers. There’s a pulled partition between the foyer and the living room beyond; I can hear the sound of a television sitcom on the other side. “In here.”

His fingers still wrapped around mine, the kid pulls me into a room to the right of the front door. It’s a tiny space. I realize almost immediately that it’s supposed to be a coat closet, or an umbrella room—some kind of pre-war outdated storage space that can barely fit a twin bed and a dorm-room mini-fridge. He’s put up shelving around the tops of the high ceilings to hold his clothing and books. A student, maybe, renting a tiny room in someone else’s apartment.

When he takes my other hand in his, and pulls himself close, I look at the boy for the first time. He’s got a pretty face. Big, open, liquid eyes. Soft pink lips. Pale, smooth skin. The fuzz on his jawbone is downy and trimmed to a point. There’s a corresponding line of thin fur that trails down his stomach to his pubes. He looks like a young James McAvoy as Tumnus the faun. “I really hoped you’d show,” he says in the softest possible voice.

I don’t get the impression that he’s not supposed to have guests. I do, however, understand that he’d rather keep our conversation quiet. “How could I resist a beautiful boy like you?” I whisper.

He is beautiful. Half of me is convinced something got to go wrong. He’s probably a bad kisser. He’ll get my pants off and decide I’m not the guy for him. Maybe he’s got a colostomy bag. Like the academic, he has to stand on tiptoe to press his lips to mine. I raise my hand. Cup his jaw. Pull him in.

No. He’s a great kisser.

He’d greeted me shirtless. All he’s wearing is a pair of soccer shorts. They slip to the ground in a puddle. His dick is hard already, curved, pointing toward my feet. I seize it with a fist and pull him closer. “Daddy,” he whispers.

“Be a good boy,” I tell him as I struggle out of my jacket. “Get my pants off and suck me.”

The kid obeys, but first kneels down to remove my shoes and socks. Then he unbuttons my shirt and slips it over my shoulders. Finally, he unbuckles my belt and unbuttons my jeans, and tugs them down with my shorts. He stares at my cock as he helps me step out of the last of my clothing, but not until he pushes me back onto the thin mattress does he finally open those soft lips and take my meat between him.

He’s no disappointment in the oral department, either. Fuck. Far from it. The sensation of his mouth on my dick is electric. He’s not gagging; I must’ve done all right in that bookstore washroom. He’s going down on my inches like he’s starving and it’s a nine-inch sub. Then he’s back up with his narrow waist between my thighs, taking my tongue in his mouth. Back down to the dick he goes, sucking and slurping on it hungrily. Then up to my mouth again, trembling with pleasure and desire as I run the flats of my hands down his smooth back and across his tiny little butt.

I’m not even aware I’m pulling apart his cheeks and fingering his butthole until he pauses, on one of his trips between my mouth and my dick. “I didn’t get ready to be fucked,” he whispers. “I just wanted to suck tonight.”

“That’s okay,” I say, meaning it. If anyone’s going to get me off orally, it’s going to be this kid.

Am I surprised then, minutes later, when he gets my dick especially wet with his spit, then reaches around and pulls my dick to his tiny little pucker as he makes out with me? I’m not, really. I say nothing, though. This can be his decision.

I feel him rubbing my sloppy-wet knob against his boyhole. There’s barely enough room for him to sit up on me without knocking his skull on the shelves overhead, but he rests his weight on his knees and leans back anyway. I tuck my fingers behind my head and watch him. He’s struggling, internally; he wants me inside him, I can tell, but he’s not sure if he should.

“It’s all right,” I whisper, startling him enough that he opens wide his half-closed eyes. “You don’t have to. You’re a good boy.”

I can see it written plain on his face. He doesn’t have to. But he wants to. He wants to be a better boy. The best boy.

He spits in his hand. Adds the moisture to his hole. Then slowly, almost painfully, he starts backing down on my cock. His own dick, fat and curved down, drips with precum. “Fuck me, daddy.” He mouths the words more than pronounces them. His eyes are closed again. He’s lost in a world of his own. “Fuck me.”

“Good boy,” I say again, and then again. “Good boy.” Over and over I use the words, as he engulfs more of me. Each time I invoke the phrase he sighs to himself. He’s happy to be a good boy. He wants to make dad proud, I can tell.

It’s not difficult to get all the way in the kid. He swallows the last few inches in a single, greedy gulp. He rests for a moment, then begins sliding up and down the pole. With his hands resting on my chest, he leans forward and looks down into my eyes. His lips part. For the longest time, I wonder what he’s going to say.

Finally it comes out. “I love it.” Plain and simple. What every dad wants to hear. “I love it. I love it,” he repeats.

“I . . . love . . . that . . . ass,” I whisper back, delivering each word with one of his thrusts. “Kiss me, son.”

When he shifts his weight forward, I pivot my hips upward and plant my heels on the mattress. I take over the hip action; he’s a curled ball over me, his mouth glued to mine. The bedsprings squeak as I begin pounding his hole from below. It’s not going to take long to shoot in the kid, I know.

“You want my load?” I ask. “You want dad’s load?”

He doesn’t have to assent. I can tell by the hunger of his kisses that he craves it. Then, “Please,” he says. “Please just fuckin’ load me.”

We’re still keeping it as quiet as possible. The TV’s laugh track from the other room is still louder than any noise the two of us are making. When I cum, it’s silently. My lungs seize. My cock lunges into the deepest part of the boy. He gasps, and presses his palms against the shelving overhead. While I quietly unload into his guts, he releases his right hand and furiously beats his downward-facing dick. It’s mere seconds until he releases a load onto my chest.

For long seconds we remain frozen in that tableau. Then slowly, like a rag doll, he crumples down onto the mattress beside me. My cock comes out with a sloppy squelch. I put my arms around the boy and become big spoon to his little, as his sperm glues my chest to his spine. He raises one leg for a moment, so that he can maneuver my cock between his thighs. Then he brings them back together again.

Jackpot, I think to myself, as the boy sighs with contentment. As he snuggles against me, the two of us cuddle and silently listen to studio audience applause in another room.