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.
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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?"
