Fisting Expedition in Rogers Park

Author's Note: This is a hardcore fisting story, so don't read it if that's totally unappealing to you. Anticipating some feedback ahead of time: no, it's not painful at all if you're doing it right; no, your ass isn't permanently loose if you do it; and yes, it can definitely be extremely pleasurable and intimate. Feel free to send me an email if I didn't already answer your question.

*

Chicago was ridiculously cold, exactly what you would expect in the middle of February, the whole city covered in a thick blanket of ice and snow. Spending most of my time trapped inside my warm apartment, I'd been watching porn and jerking off constantly, and that's exactly what I was doing at 1:00 AM. With my rock hard dick in hand, I was browsing an old hookup site of all places, the page a derelict relic compared to when I'd first used it coming out five years earlier. I hadn't logged into my account in six months, but after spending the whole winter flirting with the same tired crop of guys on Grindr, I was eager to finally see some new faces.

My profile on the hookup site had another advantage too: it was faceless and explicit about my kinks, boldly declaring my interest in fisting to anyone who clicked on it. I'd always been afraid to openly advertise my fetish on the other app, where my face was prominently displayed, worried that friends or coworkers might happen upon my profile and suddenly learn way too much about my sexual proclivities. I shouldn't have cared about what anyone else thought, but I did. Maybe that sensitivity reflected my own initial reaction to fisting.

I was an 18-year-old college freshman the first time I happened upon a video of a guy getting fisted, watching a few seconds of the clip out of morbid curiosity. The top was brutally punching the bottom's hole, pulling his fist all the way out and immediately plunging it back inside the gaping maw, and I felt horrified. I quickly closed the tab in my browser, wondering how an activity that seemed so violent and destructive could possibly feel good. Surely that bottom's ass was ruined for life. Could he even appreciate getting fucked after being destroyed like that? Fisting was immediately a hard pass until years later, when a guy I'd hooked up with a few times casually mentioned that he was into it after inquiring about my fetishes. I never would have guessed from our encounters; his hole had definitely been accommodating, but it was still tight and looked completely normal. When I pressed him with probing questions, he admitted that getting fisted was the most enjoyable, pleasurable thing he'd ever experienced in his life. My curiosity was instantly aroused, knowing that his ass wasn't cartoonishly wrecked and permanently loose after fitting a whole hand. Maybe fisting wasn't the horrible, sadistic thing I'd assumed when I first encountered it. Maybe it could actually feel good.

The next time we fucked, I wound up burying my hand inside him. The experience was brief, just a couple insertions after more than an hour of stretching his cum-lubed hole with my fingers, but seeing the bliss on his face when the whole thing eventually sank inside, hearing the way he moaned swallowing up that much girth, I was hooked. I suddenly found myself obsessed with insatiable bottoms, devouring hours of fisting porn, watching every clip I could find and reliving that moment when my whole hand had slid into another person's hole.

My fuck buddy moved back home for the summer a couple weeks after his hole had been wrapped around my wrist, denying me the chance to immediately explore more. I texted him when the new academic year started, but he revealed that he'd transferred schools. Just my luck. In my last years of living in a small college town, I managed to find a couple other curious bottoms, but they were total beginners, neither of them actually managing to swallow up my hand like the first guy had.

When I graduated and moved to Chicago to take a job, the universe of gay men around me suddenly seemed infinite. I'd met up with six enthusiastic bottoms in the city trying to replicate my first fisting experience, wanting to live out the scenarios I'd seen in videos online, only one of them actually managing to take me to the wrist. I was only 6' tall, but apparently I had absolutely massive hands, a serious challenge even for guys who enjoyed regularly getting fisted. I should have been meeting more people and trying more often, but it was discouraging to constantly fail, to hear over and over again that conquering my girthy fist was going to take a substantial amount of practice.

The site's message notification chimed in my headphones, interrupting my mindless scrolling. My profile was honest about my interests, but it rarely attracted any attention; I hadn't actually met up with someone I started talking to on the site since I was 18. I eagerly clicked on my inbox, wondering if my luck had finally changed.

"What's up?" the message asked. "Looking to fist right now?"

He was 24, 5'10" and 180 pounds, a Latino guy with golden skin, brown eyes, and black hair. I hadn't seen his face yet, his dick picture trying way too hard, but I didn't care about any of that. I was already obsessed with the image displaying his massive, smooth bubble butt, pumping my cock harder as I fantasized about taking him up on the invitation.

"Can you host?" I quickly replied. "I definitely can't right now." My roommate was asleep down the hallway, just a few hours left before he needed to wake up for his morning shift at a coffee shop, and I had enough fisting experience to know that it definitely wouldn't be a quiet activity.

"Yeah," he answered. "I'm douched and ready right now. Want to come over?"

I hadn't met up with anyone in months, but I couldn't stop staring at the picture of his alluring ass. "Where are you?"

"Rogers Park."

Of course he was all the way across the city. I lived in West Loop, and I knew from all my trips home from the gay bars in Boystown that the trains definitely moved faster when it was late at night. Unfortunately, I'd have to take a train to the Loop and then transfer to another train to go north. Maybe that would take 45 minutes or maybe it would take more than an hour, depending on whether I had to wait twenty minutes for the next train to show up.

"Might take me an hour to get up there," I wrote. I didn't want to waste his time.

"Oh, maybe we should wait then. I have to get up for work in six hours. You free tomorrow? Around 7:00 PM maybe?"

Apparently he was willing to lose some sleep to have a good time right now, but I couldn't fault the guy for not wanting to give up that much. I was so tempted to walk out the door that I'd totally forgotten I was supposed to be working in the morning too. "Yeah, that might work," I wrote back. The guy asked for my phone number and I waited for him to text me, my eyes still fixated on his smooth, golden ass and fantasizing about the possibilities.

I'd visited Rogers Park once before on a fisting expedition. A twink with a ton of experience under his belt had accepted the challenge of my massive hands, driving all the way to West Loop to pick me up. Actually seeing my hands in real life, stretching his fingers around the widest part of one and realizing they were inches away from meeting, he'd instantly started lamenting that he was out of poppers. We stopped at a sex shop in his neighborhood, the place right next door to a gay bar, and I appreciated that this part of the city I'd never visited before must be crawling with kinky gay men. In the end, the experienced twink was the second person to ever take my whole fist, the first in two years who had actually managed the feat. After an hour of endlessly sniffing poppers and a few successful penetrations, he announced that he was already spent. I fucked him and then he drove me home, the guy begging for the chance to try again the whole way back to West Loop. We flirted with the idea of meeting up a second time for a couple of weeks, but it never happened. My experiences never seemed to pan out the way amateur videos portrayed. He'd pick me up and spend an hour sniffing, struggling to take my hand, and then what? I'd shove it in a few times and he'd tell me he was done. I didn't want to volunteer for another round of disappointment.

Now, though, sexually pent-up after being confined indoors for months, I felt ready to try again. My phone vibrated on the desk, the screen lighting up with a text from an unknown number. "Hey, you have a face pic?"

I picked it up and sent the guy a couple of my best ones. "You?"

"You're really hot," he wrote, a couple of his pictures appearing a few seconds later.

His clean-shaven face was soft and slightly feminine, his fine black hair shaved on the sides and longer on the top. He was definitely a good-looking guy, but could he handle my fist? "Any of your ass in action?" I asked, eager to see an example of what he could take.

He sent a short video clip of his ass getting fucked, a dick plunging in and out of the huge, perfectly smooth brown globes of his bubble butt, and I was smitten. I wanted to ask if he had any videos of himself taking a fist, but even if my big hand did prove too much, I knew I had to have that ass. I was jerking off more fervently than I had all night replaying the clip over and over again, listening to him seductively moaning as his cheeks clapped into the top's body. "Fuck me harder!" he begged in the video. "Use that pussy!"

"Fuck, that was so hot," I finally replied after watching the clip ten times. "Noisy and verbal. I love that."

"Just imagine how noisy I'll get when your fist is in there."

"Yeah, I definitely am, and it has my dick rock hard." He talked a big game, but they always did.

"How's tomorrow looking?" he asked. "I'm Diego, by the way."

"I think I can make it work," I answered. "I'm Luke."

"Nice to meet you, Luke! So what are you into?"

"Haha, I think my interests were pretty clear on the site."

"Lol, punching holes open?" he wrote.

"I'd love to get that far! I have huge hands and they've always been a serious challenge."

"Don't worry about that," Diego assured, just as so many other eager bottoms had before him. "I've been told my hole is very accommodating. Lol."

"That sounds perfect," I replied. "And really fucking hot."

"You cool with poppers?" he asked.

"I don't think I've ever tried to fist a guy who wasn't sniffing."

"Good!" Diego wrote. "Fuck, my hole is throbbing right now."

I'd been down this road plenty of times before with a hopeful bottom, but it was still fun to imagine that he might finally be the one I could realize all my fantasies with. "I wish I could just leave and destroy your ass right now."

Diego sent a picture of himself kneeling on a couch, his smooth golden ass framed in a blue and white jockstrap. "I wish we could! I really want to be your bottom fist toy. Punch my boy pussy out and make this gaping cunt yours. Fill it up elbow deep maybe?"

I could tell he was just as horny as I was right now. "Let's see you actually take my hand first," I wrote. "But you sound like a total fist slut."

"I really want you in me and filling me up," he replied. "I want to hear my hole squelching while you punch it hard and leave me gaping open."

Reading that I almost busted, imagining myself actually living out the scene, but I didn't want the chat to end yet. "If you can take my fist like that, you'll be the only guy who ever has."

"It's been three months since my last fisting," Diego wrote. "But I can do it. You'll see."

I sighed reading the message, my enthusiasm instantly deflating. He hadn't taken a fist in three months? The guy sounded eager, but so had all the others. I already knew he'd never be able to take my hand the way he was promising on his first try, but I still wanted to fuck that beautiful ass. "Why so long?" I asked.

"My regular fisting buddy has been gone on business," Diego explained. "He usually keeps me pretty loose. You want to leave me with a loose, gaping boy pussy? I want to hear it squelch and I want my body squirming with every punch. Fuck, I really need it."

Despite my doubts, I was pumping my cock hard again. "Fuck yeah, that's how a boy cunt should be. Loose and sloppy."

"Come over tomorrow," he wrote. "7:00 PM? If you want to come later that's cool too. I'm right off the Loyola Red Line stop."

I knew I had to try. "Yeah, I'll be there."

"Get ready for a tight hole tomorrow," Diego replied.

That made me wince. A tight hole was exactly what I /didn't/ want, but I played along. "It won't be tight for long. Not with these big hands stretching you out."

"Shove those poppers up to my nose and feel my cunt open up for you little by little. This pussy needs to get fucking stretched out."

"Stretched to its limits," I wrote. "And I'm sure we can get there, but seriously, only a couple of the many guys who have tried could even get my hand all the way inside their holes."

"Oh, don't worry, I will," Diego promised. "You're going to be punching my cunt out tomorrow night. 7:00 PM." He sent his address with a smile emoji.

At least I'd definitely be fucking his perfect ass. "I'll be there."

"Awesome," he replied. "You should save your load up for me tomorrow night. I'll be all poppered up with your big hands punching my cunt and then you can fuck every drop of your cum into me."

"I can't wait to hear you beg me for it," I wrote, thinking of the clip he'd sent, hearing his desperate, pleading voice in my mind. I was already obsessed with the idea of making Diego moan like that for me.

"Fuck yeah! Tomorrow! Alright, I'm going to bed, Luke. Excited to meet you for real."

"Me too," I replied. "See you tomorrow."

Diego sent a winking emoji. "I can't wait!"

I hadn't logged into the site in six months because it never seemed to get me anywhere, even with my profile boldly proclaiming my fetishes, but now I was glad I'd signed in. Realizing it was after 2:00 AM, I decided to sleep too, climbing into my bed and pulling a blanket over my body. Thinking about Diego, his big, beautiful ass still crystal clear in my mind, my dick was full and throbbing. I struggled not to cum as I stroked it, knowing that I would have the opportunity to shoot two days' worth of my seed inside his hole tomorrow. I finally let go, all my kinky fantasies subsiding as sleep overwhelmed me.

***

I spent a hellish day in the office, so slammed with work that I didn't even have a chance to glance at my phone until lunch.

"Hey," Diego had written with a smile emoji in the morning. "Still down for tonight?" he asked an hour later. "Let me know if you still want to meet up," he added just a few minutes before I finally saw his messages.

He was definitely looking forward to hanging out tonight, already seeming to worry that I might flake. "Yeah, I'm still down," I wrote. "Sorry, really busy day at work."

"Unleash all your stress on my pussy tonight," he quickly replied. "Use me up until I can't take it anymore. Fuck, my hole is throbbing just thinking about it."

One way or another, that's exactly what I planned to do. "Fuck yeah, I can't wait!" I felt my dick filling out in my dress pants, the temptation to go jerk off in the bathroom almost overwhelming. I resisted the urge to scroll up to Diego's ass pic knowing that scores of other people were sitting around me, but I pictured those smooth brown globes clearly anyway. Thank god work was going to keep me busy until it was time for my second trip to Rogers Park.

***

When I stepped outside bundled up in my winter coat, it was ten degrees, the wind gusting so menacingly it was literally pushing me toward the Green Line station as I walked. Maybe it was a sign? I timed the train perfectly, stepping onto the platform right as it slowed pulling into the station.

"On my way," I wrote as I settled into a seat for the short trip into the Loop.

"What's your ETA?" Diego asked after I'd already transferred to the Red Line and started moving north.

He'd spent the whole day seeming to think I was going to flake, like I was the one who was too good to be true. "Probably thirty minutes away now," I wrote.

"Cool." He didn't even wait the whole thirty minutes to check on me again. "Where are you now?"

"Berwyn," I answered. "Only three more stops!"

"Can't wait to be your slut tonight," Diego wrote. "My cunt is going to be a gaping mess when you're finished with it."

Just imagining that sight had my dick stirring. Hoping to avoid tenting in my gray sweatpants when I finally stepped off the train, I slipped my phone into my pocket without texting anything else.

"This is Granville," the automated announcement declared, chimes sounding as the doors shut. "Loyola is next. Doors open on the left at Loyola. Soliciting and gambling are prohibited on CTA vehicles."

I chuckled to myself, definitely feeling like I was gambling coming all the way up here. Whatever, I was going to make the most of it. I stood up and headed toward the door, grabbing a pole as the train pulled into the station. The doors slid open.

"This is Loyola."

Diego's stop. I bounded off the train, into the frigid air of the open platform, whipping my phone out to check the GPS as I climbed down the stairs. I exited the station and walked toward his apartment, the sidewalks relatively clear until I actually reached his street, an obvious sheet of ice seeming to stretch endlessly before me. My pace slowed struggling not to slip, every building on the street surrounded by wrought iron fences with sharp-looping points at the top of each bar. I sighed struggling across the ice sheet, wondering who thought that was a brilliant design in a city that faced slick, icy sidewalks for so many months of the year. I trudged on anyway, those pointy ends threatening me every time I felt my sneakers slide. I reached the point where the GPS had led me, but it was dark and I realized I couldn't see the numbers on any of the buildings around me.

"I think I'm outside?" I wrote.

"It's the building with the yellow courtyard," Diego replied. "First door on the left."

Looking around in the darkness, I couldn't see the color anywhere. "Can you come find me?"

"Yeah, I'll be right down," he wrote.

I stood there for a couple of minutes trying to divine where his building was, struggling not to slip on the ice every time I moved, when I noticed a figure across the street walking toward me. Seeing no one else outside right now, I assumed it was him. I crossed the street and he kept approaching, swinging a gate open. After a few more paces, I recognized his face beneath a hoodie. The guy was even more attractive in person. "Hey," I greeted, nodding my head.

"Hey, I'm Diego," he said, sounding nervous now that we were meeting in real life. He reached out his hand.

I smiled at him as I firmly shook his hand, already imagining myself inside him. "And I'm Luke." Anxious or not, despite all the obscenely slutty things he'd texted the night before, Diego exuded warmth and kindness.

"Nice to meet you, Luke! Come on in." He turned and started leading me up to his building.

My gaze quickly wandered to Diego's jeans, the mounds of his ass beautifully accentuated in the tight fabric, begging to be appreciated. I couldn't wait to tear the pants off of him, my dick stiffening as we walked.

"Was the train crowded?" he asked.

"No, not bad at all. I think I almost died getting here, though," I joked.

He peered back for a second, a serious expression on his face. "What?"

I laughed as we walked up to the building's front door. "All that ice on the sidewalks and all those sharp, pointy fences everywhere! I would have been here five minutes ago if I wasn't worried about falling down and impaling myself."