I Fucked Half the Men of Chicago. (God, I Love the Windy City.)
"As all true love stories begin, I started my night on my knees in an alleyway, with a half dozen men shoving their semi-hard chubs in my face."
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Like many New Yorkers, I have a tiny bit of a bias when it comes to the city. Even though rats the size of chihuahuas brush up against my legs as I walk down the street—I’m convinced it is the best city in the United States. And there is nowhere else in the world I could live, especially as a bisexual, polyamorous kinkster. It’s like, have you been to Brooklyn? Everyone here is bi, poly, and rushing to the subway with a vibrating butt plug up their ass that their Dom controls. Bitch, I live for it.
But none of y’all told me about Chicago. It is diverse. Queer. The boys are bi. And they play a little hard to get, which, frankly, I don’t mind from time to time. Make me step up my game and work for it.
And work, I did, especially my first Saturday night out in Boystown with my friend, Ella. Ella is a powerful slut. Truly, she knows how to use her sexuality to get what she wants, and she is living her best life. She is on Grindr as a cis woman and CLEANS UP. She gets all the bi boys. (While a part of me is like, maybe this isn’t the app for you, another part of me is like, get that dick.)
So when we went to Cell Block, a cruisy, gay sex club with dark corners, an alleyway, and a sling in the center of the room, I wasn’t (too) worried she’d be out of place.
“Zach, I love it here. I suck so many guys’ dicks.” That she did—but this story isn’t about Ella (or how she and I would be the same if I were a cis woman). This story is about how I fell in love with Chicago—or rather, the men of Chicago.
As all true love stories begin, I started my night on my knees in an alleyway, with a half dozen men shoving their semi-hard chubs in my face. (To be clear, this inside alleyway was part of Cell Block).
I was jerking off as many dicks as possible with my hands and quickly switching between cocks with my mouth, doing my best to keep everyone hard. It was like a plate-spinning routine. When I saw one dick start to deflate, I’d quickly rush over to suck or jerk it off. When I got that dick hard and saw another one losing steam, I’d deepthroat the semi, tongue out, licking his balls simultaneously.
Doing this juggling routine was arousing at first, causing me to pop a boner, but the sheer number of dicks was too much for one man to handle, and I started losing my erection. Alas, I had no free hand to jerk myself off, so I had to exit the alleyway. I didn’t even bother to put away my dick. I knew it would shoot back up in a second. I just needed to see a fat ass get railed.
Past the sling, where I saw a man thoroughly enjoying himself, I saw a big juicy ass in the corner, nearly bursting out of his jockstrap. He was shaking it slightly, waiting for his top to re-enter. The top, however, had lost his hard.
“Can I jump in,” I said to the two men. The top said, “Go for it.” The bottom whipped his head around and saw my now-erect penis standing at salute. He glanced at my face, making brief eye contact before returning his gaze to my fat cock. All he said was “Yes,” before he turned back around and spread his cheeks with his hands. I spat directly on his hole before tasting it. He was already wet. From lube, spit, cum? Unclear. But he was ready to go, and so was I.
Alas, angles.
Something you should know about me: My dick shoots straight up when I get hard. In fact, when I flex my dick when it’s erect, it touches my belly button. The stark angle of my dick, plus my height, can make standing sex a little challenging. Luckily, I’ve mastered what I called “The Swoop.”
Here’s how it works. Either he or I spread his cheeks apart. In this case, our forty-something-year-old big-bootied friend was on it. I bend my knees, tilt my hips back, and thrust inside his TTT (tight and tender tuchus, for those new to the zine).
Once deep inside, I typically leave my dick there for a few seconds. Let his asshole grow accustomed to this big foreign object inside of it. Then I start thrusting slowly until he loosens up. And then—then I hold his hips, lean back, and hit him with the deep thrusts.
However, our horny pal didn’t need any loosening up. He was clearly ready to go, and so the thrusts began instantaneously. He let out a long moan, and with each thrust, his cry got louder: “Uh, Uhh, UHHH.”
The man behind me, a short man in his fifties with a face full of Botox, started circling my asshole with his fingers. I angled up, implicitly permitting him to stick a finger inside.
He did, and my dick flexed inside my bottom’s hole.
“Stick your dick in,” I said.
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