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Webcam - Sex Issue 1122
Illustration: Esme Lonsdale

New Yorkers share their craziest, dirtiest and most awkward sex stories

How you doin’ (it), New York? Locals lay bare their kinky, out-there and cringeworthy only-in-NYC sexcapades.

Written by
Time Out New York contributors

We have a worldwide reputation for being DTF. But what exactly is going on inside (and outside) our bedrooms? For our annual sex issue, we asked New Yorkers to tell us every dirty, delightful and distressing detail. Prepare for titillating tales of pegging misadventures, threesomes as entrée to elite NYC and a whole lot of fetishes. And for more sexy New York goodness, dig our guides to the best strip clubs, sex shop staples, hookup bars and swingers clubs.


Illustration: Esme Lonsdale

↑ I robbed my Grindr date.

His Grindr screen name caught my eye immediately: CASH SLAVE. I’d heard about cash slaves—men who got off by giving away their money, or having it taken from them.

“I don’t want anything sexual,” he wrote. “I want you to rob me. Meet up with me, grab your dick, tell me I can’t have it, call me a faggot, take my money and go.” In my head, I thought we’d meet in a dim, seedy alley. But the actual street corner we met up on in Bed-Stuy was very well-lit, shining a spotlight on our pseudo-criminal activity. Then, I saw him: CASH SLAVE himself. He was walking his tiny dog, had bad skin, wore his hair slicked back into a tiny ponytail and was a little heavy. I bent down to pet his pooch, but when I looked up, I realized he was jittery and couldn’t even look at me.

I knew my task but I just couldn’t be mean to this guy. I got up and before I knew it, he had slipped a wad of cash into my hands and started apologizing. “I’m sorry, sir, I’m really sorry, that’s all I have on me,” he said. “I know it’s not a lot, sir, but there’s no ATM open right now, sir, but I want to give you more next time, I promise, sir.”

I just smiled and let him put his money in my hands. “Okay, well, I’ll see you around,” I said as I walked away, as if leaving a totally normal conversation and not an awkward-as-hell internet domination setup.

I couldn’t even wait the entire block home to take out the money and count it. My haul for the day’s work? Seventeen bucks.

Louie Rendon, 29, Bedford-Stuyvesant

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Illustration: Esme Lonsdale

↑I used my rich friend’s apartment to hook up.

After ending things with my last girlfriend, I resolved to date transparently: unfiltered photos, admitting to being between jobs and being honest about having dated men. (Some lesbians, I found, staunchly disapprove of this.) In short, I would charm the ladies with my refreshing authenticity.

But charm could not compensate for my digs in Queens. Wedged between Costco and a parking lot for ice cream trucks, the commute was a dating deal breaker. So when a friend asked me to house-sit his opulent Central Park West pad, I happily agreed. Couldn’t I take a brief integrity hiatus and play rich girl for an evening?

At the Stonewall Inn, I dazzled a gorgeous NYU grad student with tales of my totally fabulous, totally fictional life. She asked to see my mansion in the sky. Feeling giddy but guilty, I hailed us a cab back to Central Park West.

As the doorman’s gloved hands parted the massive front doors, my date looked around quizzically. “I think my uncle lives in this building,” she said.“Really? Which apartment?” I asked, as if I knew any of the neighbors.

6C. My friend’s apartment.

Of all the women in New York City, I had wooed the one who could definitively call my bluff. Feeling ashamed, I made up an excuse to get her to leave and returned to 6C alone. On the refrigerator I noticed my date’s year-old high school senior portrait. I vomited in the sparkling sink. I wasn’t rich enough for this apartment. She wasn’t old enough for bars.

Katherine Hunt, 33, Lower East Side

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Illustration: Esme Lonsdale

↑I was pissed on at kink camp.

Over lunch one day, a friend told me, “I’m going to a men’s kink camp this summer. You have to be invited. I’m inviting you.” Cut to two months later and, in a secret Northeast location, I was surrounded by 300 men in the sunshine: nude, in leather or leashed on all fours.

At the kickoff party, I was melting inside from shyness when this Asian guy right next to me started screeching as a horde carried him off. They tied him to a fence and pelted him with paintballs. My pal Bart said, “That’s an ambush! Usually happens to newcomers.” I thought, Eek! Would I hate that? Or maybe love that?

Two nights later, I was still feeling kind of homesick for New York. In the dungeon barn, I watched a rope master hanging twinks from the ceiling, when this pretty Puerto Rican fella named Diego I’d been eyeing all weekend sauntered up saying something about “pee play.” I said, “Oh. Yeah, I tried that once, and you know what? I loved it!” His eyes lit up. Diego motioned to this Ed Harris look-alike standing by his side. Suddenly, the two had me in a headlock, got my hands behind my back and handcuffed me. They dragged me outside, threw me to my knees and yelled to a single-file line of men waiting to use the toilet, “Don’t piss there! We have a urinal right here!” To my surprise, as seven men towered over me and the streams began to flow, I finally felt right at home.

Kevin Allison, 47, Bedford-Stuyvesant (

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Illustration: Esme Lonsdale

↑I used threesomes to see fancy-ass apartments.

After four months of struggling to stay afloat in NYC, I couldn’t believe I was sitting in a Tribeca loft sipping wine, about to join a ménage à trois. I wanted a distraction from the grind, so I answered a personal ad: Kinky woman wanted for threesome with rich, sexy couple. It was completely out of character for me, but multiple orgasms were exactly what I needed to forget my money troubles.

After I made out with them both, I reminded them that I was only into having sex with women. They found that even hotter. She and I had sex while he watched, then they got down while I watched. It was voyeuristic and arousing. After a couple of hours and a few orgasms, they suggested I stay over. We had omelettes for breakfast the next morning.

I had to do this again. Two months later, I did, meeting up with a polyamorous lesbian couple who lived in a chic brownstone in Brooklyn. Our foreplay consisted of oysters, copious amounts of champagne, lesbian porn, sex toys and role-playing. Besides the bed, we had sex in their enormous stand-alone shower. I stayed the night, and we all had sex again in the morning.

After my second tryst, I started to see a pattern. My kink wasn’t just threesomes, but hooking up with people who had what I saw as a successful life in New York City. After one more rendezvous, I decided I didn’t need my fantasy anymore. It was time to be my own success story.

Jacy Topps, 38, Glendale, Queens

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Illustration: Esme Lonsdale

↑I tried to peg my boyfriend.

Shawn had a brand new strap-on in a box beneath his bed, and I was determined to break it in. I slid the leather harness over my hips and fastened the buckle in back. It’s thick straps cut into my waist, confining me as if I were laced into a stiff combat boot.

And then the dildo came out six inches of Barney-purple silicone. Liek a drunk trying to put on a condom, I fumbled with fitting my lubed-up dick into the rubber ring at the harness's center. Eventually, Shawn had to secure my penis for me. Now that I was properly outfitted, I felt ready to fill him up.

“Is that it?” I asked, prodding to the far right of his anus, “Um, not exactly,” he said. “What about now? Am I in?” I wondered aloud, fucking the air beneath his ballsack. “Still no.” He was on all fours and suggested flipping over onto his back, which I found even more difficult. “This is hard,” I complained. “Can’t you go back on your hands and knees?”“I fuck you like this all the time!” he exclaimed. “Yeah, but you can actually feel your penis!”

All this raid-fire arguing was turning what was supposed to be a raunchy exploit into an episode of Seinfeld. Though his navigational suggestions (“To the right, no, up a little”) were constructive, it began to feel like we were copiloting a forklife instead of getting it on.

During the reare thrusts that actually granted me access to Shawn’s asshole, his taut muscles and my arrhythmic humping popped the dick out liek a champagne cork. When I did achieve more than one pump, it became too intense for him, a discovery that shocked me, considering that this mane routinely inserts a stainless-steel plug the size of an apple into his bum.

Before I knew it, Shawn was soft, and I felt like I’d failed him completely. “Maybe I just like stationary things in my butt,” he said. He washed off the dildo and placed it back in its back, where it remains. For now.

Madison Bloom, 28, Bedford-Stuyvesant

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Illustration: Esme Lonsdale

↑I had a lot of Skype sex.

Two years ago—after yet another guy tried to finger me like his hand was an eraser and my clit was a huge spelling error with just seconds to go on a test—I gave up sex IRL for a few months.

When a dude on OkCupid messaged saying he wanted someone to watch him jack off, my initial reaction to his request was disgust. But as a professional sex writer- on a self-imposed dry spell, I grew curious, wanting to understand his fetish. We struck up a conversation, and he turned out to be really nice. It also didn’t hurt that I had a thing for watching solo-masturbation porn. I decided to give it a go.

Here’s how our relationship worked: I’d text him to meet me on Skype, enjoy myself while I watched him come, then log off. It was like Dial-a-Dick: sexually satisfying, without requiring me to change out of my sweats (my camera was always turned off), and his cock was so beautiful it should be in the Smithsonian after he dies.

The funniest part? He lived four blocks from my apartment. We never met.

Dana Hamilton, 29, Astoria

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Illustration: Esme Lonsdale

↑I popped my BDSM cherry.

On a brisk Monday afternoon, I approached 45th Street right on time, just as I’d been instructed by an older man who’d cruised me on the subway a week earlier. I assumed I was headed toward his apartment, but soon the directions revealed that I was coming to his job at a Broadway theater.

I wandered lost and alone through the stage door and the eerily empty backstage, surrounded by towering 1930s set pieces, until I found stairs leading up to the dressing rooms. He was sitting down, intensely focused, repairing a shirt for the show’s leading man. Without looking up from his needle, he firmly instructed me to “sit down,” in the same demanding tone he’d used to ask my age when we first met.

“See that bag over there? Open it.” He named each item that I pulled from a black leather bag and placed on the counter: “Flogger. Paddle. Blindfold. Ball gag.”

I looked at these tools, all laid out next to the chorus-boy makeup, and then over to him. He was looking at me for the first time. My chest was pounding. I’d never done anything like this before.

“Strip down,” he instructed. “Hands against the wall.” He put his work away, and my knees shook as I awkwardly peeled off my long johns. Once I assumed the position, he came up behind me, caressed my torso and established a safe word. Feeling his stubble against my jaw, he said lightly into my ear, “This is the flogger.”

I never did use that safe word.

—Derek Smith, 29, Bedford-Stuyvesant

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