Gay sex in the city

48 hours of cruising offers plenty of eye candy.

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As the erect cock of a girthy, middle-aged gent at Paradise Sauna (2912 W Montrose Ave, 773-588-3304) extends toward me like the offering of a firm handshake, I’m wondering if this is really my life. It’s Sunday afternoon and the end of a long weekend of raunch that I swear started innocently enough.


On the Friday night that kicks off my dirty gay weekend, my curiosity is initially piqued by a press release that reads, “Dominant gay muscle couple seeks submissive sketch comedy audience.” It’s the tag line for Pinque Pony (Donny’s Skybox, 1616 N Wells St; Fri 21 at 10:30pm), a sharp new sketch revue starring comedian Andy Eninger (whose physique I used to drool over at XSport Fitness) and John Loos, his much younger and equally hot boyfriend. The show is whip-smart in its take on Grindr, threesomes and uniform fantasies, and titillating enough that suddenly the night feels ripe with possibility.


I end up in Lakeview where I’ve been tipped off that a Boystown bar has begun hosting a “gentleman’s social hour” every Friday night after last call. According to the bartender, who is ominously slicing into a mighty large cucumber while chatting me up, it’s an invite-only party in which doors are locked, lights are down, shirts or pants must come off and the sale of booze is strictly verboten (although complimentary Colt 45s are handed out to ease the tension).


Sure enough, as the witching hour nears and the clueless masses disperse into the night, in-the-know bunches of men in their twenties and thirties fill the joint. Shirts and pants start landing on the floor in piles that resemble clumps of autumn leaves, and I’m surprised to see a handful of guys abandoning their sartorial senses for full-on nakedness. A machine pumps out thick puffs of fog that give the space a chalky heaviness reminiscent of the Dagobah System, and there’s enough booze rattling around in my brain that I’m tempted to make some lascivious decisions. But familiar faces are numerous and my pejunkle recoils like a house cat frightened at the sound of a whirring vacuum.


Instead, I allow two friends to talk me into a 4am trip down the street to Steamworks (3246 N Halsted St), Boystown’s ebullient bathhouse. After checking “seeing my friends naked” off my to-do list, I wander alone through the second floor’s labyrinth of doors and mirrors, which never fails to remind me of the opening sequence of Godard’s Alphaville. I follow a handsome gent to the rooftop, which I realize is a smoking lounge (picture the burnouts at your high school, but in white towels). The guy I’m chasing lights up a fag and ignores me.


I hit the steam room and hot tub instead, and while pumicing the evening’s filth off my body in the gang showers notice a spectacled young thing moving in. “I don’t kiss,” he tells me. (I guess this means no holding handsies while perusing Top Shop together, either). I ditch this lame dud of a dude and call it a night.


Determined to have better luck on Saturday, I hit the Manhandler Saloon (1948 N Halsted St, 773-871-3339), a cruise bar tucked away discreetly in the heart of Lincoln Park. In the front room, there’s gay porn playing and the “cop” who just shot his load can’t seem to shake off that last bit of post-coital jizz (I hate that!). I make a beeline for the stable out back where things go bump (and grind) in the night. It’s early, and aside from some guy moaning and pumping his left hand furiously in one corner, there isn’t much to see.


At Jackhammer (6406 N Clark St), an old, nude Asian guy (who is a fixture on the gay scene and reportedly some sort of judge) is twirling around buck naked in the main bar to the amusement of onlookers, eventually sitting down near the stage where the go-gos shake it. I head to the Hole, the ’hammer’s basement bar and play space, which is under construction and not very busy. The enforced dress code is leather, latex or underwear, and I’m amused by two muscle twinks who look out of place in their fancy Diesel briefs. To my surprise, one of them pulls his dick out and starts whizzing exuberantly on the other. I watch in amazement as other men swarm them like bees and sniff and lick their willing armpits. The neat freak in me wants to clean up the mess. Instead, I go home and sublimate yet another failed night with some Reese’s Peanut Butter Cups.


I end up on Sunday at Paradise Sauna, a Korean bathhouse with a cruisy rep. Aside from being tattered at the edges, it’s actually not a bad place to unwind with a steam. In the sauna, a dude is becoming visibly aroused by my presence, but I shrug it off. I’m kind of over sex (until my Grindr app buzzes later that night).



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