sex diaries

The Gay Art-World Guy Searching for Rebound Sex

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the Gay Art-World Guy Searching for Kinky Rebound Sex: Male, 28, Greenwich Village, works in the art world, gay, recently single again.

9:35 a.m.:
Rouse myself out of bed after hours of lying about. Barely slept last night as I constructed long, fictional arguments with my ex, who dumped me nine days ago because he “wasn’t ready for a relationship.” My dick is unaccountably hard.
10:40 a.m.: Text Grad Student I chatted with a few days ago while hunting for rebound sex on We said we’d try to get together during the weekend. In my text, I tell him I’m going to take a riding crop to his balls. Too forward? No answer.

11:30 a.m.: Totally unable to work, I take a quick gander at Craigslist, search for a few outlying words on Men Seeking Men: “disciplinarian” (a dozen hits), “consequences” (one guy, in Hoboken), “Harvard” (none).
1:05 p.m.:
Lunch at local café. Guy with deep but still obviously homosexual voice is sitting behind me. I crane around a few times but can only see the back of his head, so I walk over to the newspaper rack and swing around for a look. His face is a disaster.
3:15 p.m.:
E-mail from Bushwick Artist asking if I’m free tonight. We slept together once about four months ago and I got back in touch with him after the breakup. He’s got Brooklyn-standard mutton chops and a beautiful bottom, high and tight, that reddens up beautifully. I want him, but I really, really want my Grad Student (still no answer). I tell him to text me later.
4:30 p.m.:
Guy whose window mine looks onto is wearing a tux. I wonder if I should wave. He’s seen me naked a dozen times, and my ex and I used to go at it in full view of him. I moved in six months ago and still have no curtains.
5:15 p.m.:
At the gym. Shocked, really: The locker room is a doghouse, nothing but overweight queens and old men optimistically coating their flabby thighs with moisturizer. I know it’s because I’m looking. Two weeks ago everyone here was a porn star.
9:45 p.m.:
Jerk off thinking about the ex.
11:15 p.m.:
Text from Bushwick Artist, who’s leaving a party and wants to know what I’m up to. I don’t respond.


9 a.m.: In the Times wedding section, only one couple I know, which comes as a relief. It’s not so bad in the winter.
12:10 p.m.:
Text from Musician, another digital rebound possibility. We’d made tentative plans to meet today. He invites me over; I hesitate, but only for a minute.
1:25 p.m.:
Arrive at Musician’s place in Sunnyside, not before a 7 train disaster that deposited me in Jackson Heights. He’s hairier than I’d expected, but the apartment’s charming and he is, like me, a daytime drinker. Not as good of a kisser as my ex, but he’ll have to do.
1:50 p.m.:
Musician brings me into the bedroom and shows me his latest purchase: a fearsome prison strap, which he bought from a Russian woman in the East Village. He wants to use it on me. Not my inclination normally, but I cut him a deal — we’ll trade stroke for stroke. I take it first, and it’s brutal, leaving nasty red bars across my ass. But I get him back for it.
2:45 p.m.:
Jerk each other off after a round robin of over-the-knee action, plus a bit of paddling in front of the mirror. We get each other, but there’s not enough chemistry for anything really intimate.
2:51 p.m.:
Cleaning up, he mentions he went to the same college as my ex. I wonder if they ever hooked up.
3:50 p.m.:
I am sitting in a falafel joint on Queens Boulevard and squirming in my seat while watching a Turkish soap opera. My life, ladies and gentlemen.
5:15 p.m.:
I feel spectacular — first action I’ve had since getting dumped. I should have done this sooner. And I already want to jerk off, but I restrain myself.
5:22 p.m.:
Thinking about ex, thinking about Musician, telling myself I won’t jerk off.
5:37 p.m.:
Jerk off.


7:52 a.m.: Wake up, grab phone to turn off alarm, check e-mail, then open Grindr. Two guys have sent me dick shots overnight. What a waste of time.
8:15 a.m.:
Still in bed, thinking about session with Queens Musician. I can still feel it, faintly. Jerk off on my chest, hit the shower.
1:45 p.m.:
Drunken two-hour lunch with my best straight friend. Naturally I tell him everything in painstaking anatomical detail. He loves it and is only upset that I didn’t take pictures this time. We agree that if he were gay he’d have his legs in the air 24 hours a day.
7:30 p.m.:
Dance performance. Depressingly, I am sitting next to an empty seat where my ex should be, but I’m not thinking too much about him  —I am too busy gazing at the butts of the boys onstage, several of whom are wearing obscenely short shorts. I resolve to get a pair. I also resolve to do more squats.


11:10 a.m.: At the gym, failing to maintain composure while watching two gorgeous men on their hands and knees. My favorite position!
4:20 p.m.:
Take a break from work to check my second, sex-and-spam e-mail account, which I’ve neglected for a couple of days. Lo and behold, a note from Grad Student! He says he’s sorry we missed each other, but that he still wants to meet — later this week? Whoever said online hookups were quick …
7 p.m.:
I meet up with a college buddy, who brings along his new boyfriend. The boyfriend, it turns out, lives in the same brownstone as my ex, right downstairs from him. “He’s really hot,” the kid points out. It’s a small world, and it’s gay, and it lives in Brooklyn. I feel ill.
7:50 p.m.:
A few drinks in, arm around me, college buddy lets slip that a common acquaintance of ours, mild-mannered as can be, is a regular at the New York Bondage Club. Good datapoint.
9:15 p.m.:
Drunk already, home alone, pissed at the world: The only guy who came up to me tonight was an (admittedly very nice) 79-year-old who asked if I was a model and called himself “Mommy Queerest.” I wonder if that’s my future.
9:23 p.m.:
Look at sex ads in cities I’d rather be in than New York. There’s some hot stuff going down in Buenos Aires, apparently. Jerk off fast and pleasurelessly.


8:10 a.m.: Not much sleep last night. Lay awake dehydrated, thinking about boys and my future. 
12:40 p.m.:
Leaving the gym, silver fox with spectacular calves holds the door for me. Imagine him pinning me down and plowing me. I do really enjoy anal sex, but it happens so seldom when I’m single — largely because I get anxious about it on first nights, and I never get second ones.
1:47 p.m.:
Lunch uptown with acquaintance visiting from London. We gossip about boys next to Botoxed-to-death Upper East Side matrons. I whine a bit about getting dumped. Maybe more than a bit. But when I complain that ex wasn’t even into rimming, Londoner gasps and says he isn’t either. How the hell is this possible?
3:05 p.m.:
Grindr in the back of a cab. Guys’ ads on the Upper East Side are kind of hilarious. It’s like having my own little sociological X-ray.
3:11 p.m.:
Text Grad Student to see if he wants to come over late tonight.
3:37 p.m.:
Grad Student responds, says he’s busy but could do tomorrow. I agree, suggest a time and give him my address. I have no idea whether it’ll happen.
10:50 p.m.:
Rereading a Tony Kushner essay in which he writes that all sex is really just a pretext for kissing. He’s right. My ex might not have been into every little act I like, but he’s the best kisser in the tri-state area.


12:50 p.m.: At MoMA. Young guy in tight jeans is leaning towards one of the De Koonings. I stare at his ass, not least because early De Kooning bores me. Then he minces over to join his boyfriend. Try not to be jealous.
2:40 p.m.:
Text Grad Student to see if we’re still on for tonight.
6:15 p.m.:
Grad Student writes back at last, says he’s coming at 9. I still think he’ll flake out.
9:20 p.m.:
Grad Student arrives at my place, late. But we get along. He is adorably nervous. We have a drink and then make out like teenagers, fully clothed.
9:37 p.m.:
He’s calmer now. With a campy flourish I pull out my favorite straight-backed chair, sit down, and haul him over my knee. I start spanking him on his jeans (which hurts my hand), then let him up and order him to strip to his underwear. He’s wearing those American Apparel colored briefs, a gay hipster cliché. All the more reason to pull them down to his ankles and spank him on the bare.
9:50 p.m.:
We move to my bed, where I finally undress. He blows me. I make to do the same but he says he’s not into it, so I put him on all fours and probe his hole with my tongue, then grab him by the balls and start smacking him again. My mind drifts to my ex, who wasn’t into any of this.
10:03 p.m.:
I go to town on Grad Student’s balls. He yelps adorably.
10:20 p.m.:
Grad Student sucks me off — and swallows me! People still do that during a one-night stand? He then jerks himself off while I tell him what a slut he is, which is simultaneously hot and pathetic.
10:41 p.m.:
Lying in bed, him on his stomach with his red ass up in the air, having a friendly debate about Occupy Wall Street and the eurozone crisis. Nice guy.
11:03 p.m.:
We shower: lots of kissing, a bit of nipple play. I invite him to stay but he heads home.
11:39 p.m.:
My sheets are soaked with sweat and I’m sleeping alone again. This sucks.


4:15 a.m.: Another night in the Hôtel de l’Insomnie.
5:40 a.m.:
Still can’t get back to sleep. Grab my phone, read the news, spend two minutes on Grindr and block four guys who all said only “Hi” or “Sup,” then pull up a favorite Tumblr with the feebly amusing name Haus-O-Ass. I had sex six hours ago and I am already looking at porn. Jerk off and barely ejaculate. I go to the bathroom to clean up, look at myself in the mirror, and say all sorts of awful things to myself.
11:45 a.m.:
Gym. So many naked guys, so little action.
3:20 p.m.:
Send Grad Student a friendly day-after text, after waiting for hours; don’t want to appear too eager. No response.

TOTALS: Two sex dates, comprising two acts of fellatio (received); one act of analingus (given); three spankings and other disciplinary acts (two given, one received); one session of testicular torture (given); two orgasms; five acts of masturbation; no sleep.

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The Gay Art-World Guy Searching for Rebound Sex