Night at Checkmate, an NYC sex club

Because reasons, I will be leaving out a lot of the details around my recent night at Checkmate, an NYC sex club to which I very much hope to return. And soon. Checkmate is an NYC institution – over 25 years old!

First, the club is in the basement of a nondescript office building that, if I had to guess, I would say is home to a number of businesses that operate in the grey area. It gives off a sort of… sketchy… vibe out of keeping with the tony neighborhood. Or, really, it gives off the vibe of a slightly shady, if still classy, building-wide enterprise, of which the basement club is one arm.

The front area has the feel of a cross between a Russian disco, circa 2024, and a New York disco, circa 1977. Lots of neon and colored lights. A dance floor. A bar where they serve the (BYOB) drinks the guests have brought. None of the cheesy porn that dominated Le Trapeze. It’s pleasant, thoughtfully decorated, and has comfortable seating around the sides.

Between the front area and the back is a locker room. Much like the one at the old Le Trapeze, but slightly nicer, it’s attended to by Sasha, the affable, fun, funny all-purpose host. He told me he’d worked in the building for twenty years, at the club, for five. Fortifying my building-wide-enterprise hypothesis….

The back area consists of three smallish, clean, comfortable, well appointed rooms. There’s no large play room (or at least, I don’t recall seeing one), as there was at Le Trapeze, and I don’t think I saw any sex furniture. It felt much more like a bunch of bedrooms, much less like a porn set than did Le Trapeze. Lots of pillows and cushions, though. And nice, soft lighting. Not so dark that you can’t see, and not so bright that you see more than you want to.

And the crowd: on this night, it wasn’t too big. Maybe seven or eight couples in addition to the three of us. All reasonably attractive. None materially older than 60. None younger than 30. I’m told that, on Friday and Saturday nights, it’s typically much, much busier.

I don’t remember the music.

Many people found Le Trapeze skeevy and, in its way, it was. It didn’t feel clean (even though, honestly, I think it was). It felt… filthy. Partly, this had to do with the large proportion of attendees who were fat men with sex worker companions. Partly, it had to do with the ubiquitous cheesy porn. Partly, it was the lighting. And the bedding. And… everything.

Checkmate isn’t even slightly skeevy. It felt, at least on this evening, almost… classy. As classy as a BYOB sex club can be.

The vetting procedure is real. I had to send photos before, and get cleared for an invitation, and FetLife has some sad postings by more than one person lamenting, “I don’t get it! I’ve applied multiple times to Checkmate and never heard back!” The people all were, if not hot, at least attractive. And most were, honestly, hot.

After Sasha gave us the tour, we had him pour us some scotch, and chatted just a bit, taking in the surround. It wasn’t long before we traded our clothes for comfy robes. Milica kept her sexy black tights and panties and bra on. Charlotte and I were nude beneath the robes. Just as we left the locker room, I noticed Julian – a guy I saw literally every time I was at Le Trapeze (I described him back in the day as the Venezuelan guy) and who had e-mailed me after Le Trapeze closed, telling me about this place, encouraging me to visit. I greeted him. We had a brief, warm conversation. I noticed that he was with a woman two women, neither of whom was the pretty, be-glassed blonde whose cunt I remember fondly. Both were hot. One, Kristin, a striking, spectacular tall blonde, and the other, Nora, a pretty, petite, Latina brunette. Both have his name tattooed on their backs, and both, he told me, live with him. Before the evening ended, I would feast on Nora.

Charlotte and Milica and I made our way to one of the bedrooms, and they quickly began kissing. I stroked my cock, lying next to them. Milica moved her head down between Charlotte’s thighs and, at my suggestion, began gently licking Charlotte’s clit. Charlotte and I kissed while Milica worked.

Sadly for all, whether because of technique, mood, chemistry, or what, Charlotte – usually wildly orgasmic – wasn’t responding to Milica’s ministrations. Maybe she was self-conscious. A crowd was growing at the foot of the bed, admiring my good fortune: Milica’s spectacular ass, still in her tights, lifted high in the air as she licked and, gently (she has long nails) fingered Charlotte; Charlotte’s insanely pretty face only partially visible as it was pressed against mine.

Some time passed. I displaced Milica, encouraging her to lose her tights and panties, and to sit on Charlotte’s pretty face as I lowered my mouth to Charlotte’s clit. Charlotte responded not too far from her usual to me, bucking and writhing with her first orgasm only a minute or so after I began. My cock, sadly, was in some other place, distracted by my friend’s news. As were my thoughts. Was my friend ok? The events at hand, hot as they were, weren’t enough to distract me.

Whatever the cause, this wasn’t working, so I directed Milica to sit her pretty ass on Charlotte’s pretty face, while I switched places with Milica, maneuvering my head down between Charlotte’s delicious, meaty thighs. [I should say: my cock was not hard. It hadn’t, yet, been hard on this evening, notwithstanding my two gorgeous companions and all the fun that lay ahead. I think the bad news I’d gotten was weighing it down like a lead balloon.] Charlotte’s responsiveness was, I would say, 80% of what I remembered. While, with Milica, she really hadn’t been responding, to me, she was quickly bucking, writing, and as I devoured her sweet, salty cunt, she writhed, bucked, and, no more than 90 seconds after I’d begun, she came.

I slid to the top of the bed and positioned myself on the pillows. I directed the two women to share my cock. Milica had told me this was a fantasy of hers: to share my cock with another woman. As I lay there, these two fucking hot brunettes on my cock, it still just wasn’t really responding. One of the couples that had been watching (I’ll call them N & F) positioned themselves on a settee at the foot of the bed, and she began sucking his cock. N was a good-looking guy with short hair and (maybe?) a moustache and beard not unlike mine? (close cropped). F was a sweet, hot, blonde, with nice, full breasts, and delicious curves. My view was excellent.Two pretty mouths on my cock and, beyond, a hot couple….

The next hour or so is a bit of a blur. Things went a bit sideways what with my distraction. There were several breaks in the play, and, at one point, as Charlotte and I were talking, Milica came to me and said, “I’m sucking M’s cock in the other room. Is that ok?” I said, “Of course! Go ahead!” and she returned.

There was an interlude where the three of us sat in the front disco room in our robes, talking, as a couple near us performed a strange sort of imitation of “dissociated guy in a strip club,” the woman, in what Milica told me were $400 boots and a $10 dress (“so it wouldn’t matter if she got cum on it,” speculated Milica), danced for him, and he… watched. Milica and Charlotte were convinced she was a sex worker. I wasn’t so sure. Either way – the couple was attractive, I would say early 40s, white. The only thing I noticed about her was her preternaturally white teeth. Like, too white. I was distracted: were they dentures? (Charlotte says they were veneers. I have no idea what veneers are.)

Anyway: the evening progressed, and Charlotte, eventually, left. Milica was getting fucked by N when I returned to her after saying good-bye to Charlotte. By this time, Milica was kind of enjoying being the star of the club: every man there wanted to fuck her, and I wasn’t standing in the way. N finished, and then, Julian soon was pounding his thick cock into her ass. (Later, she told me he fucked her ass really well, that she was surprised he put his cock in right after his thumb, that she might have preferred an intermediate butt plug, but he just went straight in. “You’re gonna have to go real slow,” she told him, and he did.)

Back in the day, as I recall, his girlfriend was a hot blonde with cute glasses and spectacular breasts. I remember going down on her fondly. And, I remember that they had had a policy, as I recall, of her not sucking anyone else’s cock. On this evening, he had two new (or at least, new to me – not that new, given their tattoos) girlfriends. As he was pounding away at Milica’s ass, one of them – the one I described above, Cuban, sexy as fuck – and I kissed, just briefly, before I lowered my head between her slender thighs. “May I?” I asked.

She nodded, and smiled. A cute, seductive, smile, but… somehow, I felt as if maybe she… lacked enthusiasm?

Was she “taking one for the team”? Was I being permitted to be occupied with her so as to facilitate her partner’s time with Milica? Obviously, I’ll never know. Or maybe I will. What I do know is that her pussy was sweet, and responsive, and her hands gripped my head and pushed me down, hard on her. I don’t, generally, imagine that women fake orgasms with me, and I don’t know if/that she did. If she was faking, it was convincing. She trembled a lot, shaking, and the taste of her cunt grew slightly more saline. These feel harder to fake than simple oohs and aahs. But I still had lingering doubt.

The thing that raised the most doubt, though, was the alacrity with which, after Julian finished his plowing of Milica, she lifted my head from her pussy, gave me a tender kiss, and left the room with him.

I directed Milica – her pussy and her ass well used at this point – to put her mouth to further good use, and maneuvered her back between my thighs, where she belonged. Another couple came into the room – in their 30s, hot – and they sat on the bed, as I leaned back on the settee, Milica, on her knees, swallowing my cock. Finally, finally, I was getting hard. The guy and I admired one another’s partners, each of us delighting in a pretty fucking spectacular view.

The attendant (not Sasha) entered the room to tell us “ten minutes til closing time.”

“I can do that,” I said. About three minutes later, I filled Milica’s mouth with my cum for the second time that day, and we headed to the locker room.

F, N’s partner, asked Milica for her number. “I’m not from here!” she protested. “I don’t come here often! Plus, I don’t even remember my [Google Voice] number.”

“Give them mine,” I suggested. The pen wasn’t working with the paper.

We dressed, and F gave Milica her number, getting the pen to work by using a different piece of paper.

Milica left it in the locker. I took it – not because I think F wants to suck my cock – I don’t think she does (although, although, I really liked her sweet face, her curvy body, and I would welcome that). No, I took it because I thought, “I’m gonna write about these people, and I should share what I write with them.”

So Milica and I dressed, left the place, and got in a cab, debriefing a bit. She recounted the details of the ass-fucking, in particular. And we began our debrief of my mistaken handling of the night.

I should say: I’ve left out a lot of details here. But. As fun as all this sounds – and as great as Checkmate was – it was, in the end, a shadow of the evening it might have been. And not just a shadow: a shadow that, at the end of it all, I wish I had called to a halt before it began. I recognize that you wouldn’t necessarily know that from reading this post, but that’s how it goes.

Live and learn.

Ed. note: Julian, Kristin, Nora, F, N, Charlotte, and Milica all have seen, and approved, this post.