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 Adam4Adam of all places, the web site 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 Adam4Adam profile 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 Adam4Adam 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 A4A.”
“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 Adam4Adam in six months because the site 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.”
“Oh, yeah, I don’t know why they haven’t cleared that ice yet,” he said, his voice still nervous as he punched a code into a keypad and the door unlatched.
We stepped into a cramped stairwell, a couple rows of mailboxes on one of the walls, Diego leading me up the creaky wooden stairs. “It was definitely a surprise! All the sidewalks in West Loop are pretty clear right now.”
“Is that where you live?” he asked.
I realized I hadn’t told him that, just that I couldn’t host. “Yeah, it’s really close to my office.”
“That’s cool,” he said. We reached the third floor of the building, Diego swinging a door open and gesturing for me to walk in. “Well, I’m really glad you could make it,” he said with a shy but lustful smile.
Stepping inside, the place was obviously huge compared to my apartment, and I instantly feared someone else might have to suffer listening to our debauchery. “Wait, do you have roommates?” I wondered, my voice lowering just in case someone else might hear me.
“No, it’s a one bedroom,” Diego answered as he closed and locked the door.
I suddenly appreciated why people chose to live in Rogers Park looking around his apartment. “Wow, you have a lot of space!” I hadn’t seen the whole place yet, but it was definitely bigger than the two bedroom unit I had to split with someone else, and I knew the rent must have been significantly cheaper.
Diego shrugged his shoulders and smiled again. “It’s a longer commute for sure, but I think it’s worth it for the extra room,” he said, his voice less nervous than it had been when he’d located me outside.
“Yeah, I don’t blame you!” I pulled my coat off, dropping it to the floor as I sat down on his couch, Diego still lingering near the doorway.
“Hey, I need to spend a little more time in the bathroom getting ready, if that’s cool?” he asked.
Maybe that’s why he seemed so anxious? “No worries,” I said. “Take all the time you need.”
“Just give me five or ten minutes and I’ll be ready,” he called as he walked toward an open door.
“No worries,” I repeated, a sink turning on as soon as the bathroom door shut.
I pulled my shoes and socks off while Diego took care of business, drawing my half-hard dick out of my sweatpants and fantasizing about burying my massive hand in his huge ass as I stroked. His pictures had been good enough to lead me here, but he was obnoxiously attractive in person. I knew I needed to keep my expectations in check, but whatever happened, however far we went, this was going to be a fun night. The bathroom door swung open a few minutes later, my hand bolting away as I reflexively covered myself back up.
“I think I’m ready!” Diego said excitedly, walking over to the couch and kneeling down in front of me on the floor. He’d stripped off his clothes in the bathroom, everything except the blue and white jock I’d previewed the night before, the golden mounds of his incredible ass on full display. Our eyes met as Diego’s hands grazed my thighs through the sweatpants, his expression obviously pleading for permission to remove them.
This guy wanted me and he wasn’t wasting any time getting the action started. I grinned and nodded at him, eager to finally see what he could do.
Diego peeled my sweatpants and boxers down to my ankles, his face lighting up in awe as he freed my rock hard cock. I hadn’t sent him any pictures beforehand, but I could tell he was definitely impressed with my thick seven inches, immediately sinking his warm, wet mouth down on my shaft.
“Yeah,” I sighed, relishing being touched by someone else after months of going without. The long trip to Rogers Park already felt completely worthwhile watching him greedily bobbing up and down on my cock.
Diego slurped on my dick for a couple of minutes, struggling to fit the whole thing down his throat, lifting off with a moan as he stared up at me again. He was panting, his glance ravenous as he turned himself around on all fours. He reached his hands back and spread his big cheeks open, revealing a perfectly smooth slit-like hole.
His ass definitely had some mileage on it, all the signs of having been well-used. 18-year-old me would have been as horrified as I was when I’d watched my first fisting video, but 23-year-old me felt more turned on than ever. I stroked my spit-slicked dick for a few seconds taking in the gorgeous sight splayed out in front of me, Diego eagerly looking back to observe my reaction.
My face must have been just as intent and lecherous as his was as I gripped the couch cushion with my hands, launching myself behind him and lowering my knees down to the hardwood floor. I ran my finger against his hole, tracing it up and down the slit obviously wet with lube. If he hadn’t fisted himself in the bathroom, he’d definitely been using a dildo.
Diego was moaning softly, enjoying the simple touch. “You ready to open it up?” he asked longingly.
“Fuck yeah I am,” I growled, slipping one of my fingers into his hole. His ass swallowed it effortlessly, the warm cavern hugging me tightly as I started to probe.
“More,” Diego whispered almost immediately.
I withdrew and poised two fingers at his entrance, gently rubbing them up and down his lips before slowly pressing them inside. They slid in like they were nothing, his insides instantly parting open even more.
“God, you feel so good already,” he murmured, glancing back at me. His expression was even more desirous, greedy, pleading for me to keep pushing.
Diego was already a hungrier bottom than any other guy I’d ever tried to fist. “Want to feel even better?” I asked as I slipped my fingers out, quickly shoving three back into his ass.
He moaned sensually as I worked them in and out, his hole loosening, magically growing more spacious as I filled it even more. “More,” Diego begged again.
“Yeah?” I drew my fingers back just short of pulling out, positioning my pinkie underneath them, and sank all four digits into the warm, wet, slackening hole. Diego groaned as I explored him, starting to thrust the top half of my hand into his butt more vigorously. I didn’t even realize he had a bottle of poppers in his hand, but I heard the tell-tale sound of the bottle cracking open, the guy taking two deep inhales before he screwed the cap back on.
“Give me more,” he pleaded, his voice suddenly more lustful and desperate feeling the rush of a hit of poppers washing over him.
I grinned, barely able to believe how quickly we were moving. No other guy had ever taken this much so quickly. “Fuck yeah,” I hissed as I pulled back again. My thumb joined my other fingers to form a duck bill shape, and I pressed into Diego’s hole, all five of my digits sinking inside to the knuckles. I worked his ass slowly, stopping just short of withdrawing before I buried my hand to the knuckles in his butt again.
He looked back at me, determination all over his face. “I’m ready,” he whispered with an intent nod. “You want to shove your whole hand in? Let’s get on the couch.”
“Fuck yeah,” I murmured, a satisfied smirk sweeping across my face. I drew my fingers out of Diego’s ass, his hairless hole slightly gaping open. The moment of truth had arrived. Four fingers was easy, even five after enough warm up, but then a bottom had to swallow up the widest part of my hand, the knuckles and beyond down to my wrist. That was always the real challenge, the point where they all inevitably choked.
We both stood up, Diego bolting to the bathroom and returning with a towel and an open water bottle full of clear liquid. He pressed the bottle into my hand, and then he draped the towel over one of the couch cushions, climbing up and positioning himself on all fours again. He planted his hands on the armrest, his back arched as he poked the big cheeks of his gorgeous golden ass into the air. “I made tons of that,” he said, nodding toward the bottle. “So don’t hesitate to be generous with it.”
Shaking the bottle, seeing how viscous the fluid was, I knew it was J-Lube. “No worries.” I crept up behind Diego, settling on my knees and rubbing one of my hands against his smooth butt before I poured a bountiful amount of the thick lube into my palm. I slathered his hole with it, pouring more into my palm and starting to work fingers into his ass. Being covered with the incredibly slick J-Lube made the penetration even easier, my fingers freely gliding in and out of Diego’s warm hole. I quickly worked him back up to all five, sliding out and pushing my hand all the way to the knuckles with every thrust as he gently moaned.
Diego took a deep breath, taking two huge sniffs of his poppers and burying his head into the couch. “Do it,” he whispered lecherously. “I’m ready. Shove that huge fucking hand all the way inside me.”
I pulled back one last time, my hand effortlessly pressing all the way to the knuckles. Trying to venture deeper into him, hoping to grant his wish, I definitely felt resistance.
“Shove it in!” Diego begged. “Just shove it in!”
I pushed harder, the widest part of my hand suddenly popping inside his hole, the girthy mass slipping in until his tight ring of muscle was wrapped around my wrist.
Diego gasped, his head bolting up. “Hold it there!” he groaned, looking back at me and straight into my eyes. “Let my pussy get used to it for a minute and then it’s all fucking yours.”
My hand was buried in his tight, silky insides with barely any warm up at all relative to the other guys I’d tried to fist. And best of all, unlike the others who’d managed the achievement, he wasn’t immediately begging me to pull it out. If Diego really hadn’t taken a fist in three months, he was already the most talented bottom I’d ever met in my life.
“Move it around inside me a little,” he said. “But don’t pull it out yet.”
Now I was suddenly uncertain of exactly what I should do next. Every other time I’d shoved my hand into a guy’s ass, I just held it there until they quickly asked me to take it out. I’d seen tons of videos, but I had no real life fisting experience at all past the actual insertion. I figured the best path forward was just to carefully read Diego. If he was exuberantly moaning, if there was bliss plastered all over his face, I would know I was doing a good job of giving him pleasure.
I slowly twisted my hand around as Diego whimpered, sensing his hole steadily opening up even more, like it was greedily demanding to be filled up. I tried pushing deeper into him, feeling his walls parting to make way, my wrist slipping even further into his ass. Probing with my fingers when there was nowhere left to go, rubbing his insides, I felt Diego’s heart beating, his steady pulse thumping against my fingertips.
“Oh my god!” he grunted, his face peering back again. “Hold it there! Oh my god, that’s definitely the biggest hand I’ve ever taken!”
Looking into his eyes, I saw hunger like I’d never seen it before. Every other guy I’d tried to fist looked nervous, afraid even, but Diego was desperate, completely determined to deliver exactly what he’d promised. “You like it?”
“Fuck yes!” he answered emphatically. “Move it in and out, but keep it inside me,” he instructed. He sniffed the poppers again, moaning softly as he capped the bottle.
I withdrew a couple inches of my hand, Diego’s ass lips stretched wide around it, softly pushing back inside and burying myself as far as I’d ventured before. I repeated the action a few times, hearing his moans of pleasure mounting. The anxiety I’d picked up on in our first moments together had completely disappeared, transforming into pure lust.
“Faster,” he breathlessly begged.
I increased my pace, letting more and more of my hand slip out before I forcefully thrusted it back inside Diego’s ass, hearing him moan ecstatically from the cushion.
“Fuck!” he groaned. “Use that fucking cunt! Stretch that fucking boy pussy!”
“Yeah?”
“You’re going…to make it so…loose and sloppy,” Diego struggled to say as I pulled my hand in and out of his hole. “You’re going to…fucking punch it tonight!”
I slapped one of the globes of his massive brown ass hard with my free hand, the other buried beyond the wrist inside him, and Diego yelped. “I’m going to use that boy cunt up, right?”
“Yes, sir!” he whimpered. “It’s your cunt now. You’re going to fucking use me up. You’re going to punch that pussy until I can’t take it anymore.”
“Fuck yeah I am,” I grunted, starting to slide in and out of his ass again.
“Punch me for hours,” Diego pleaded, sniffing the poppers again. “Punch my cunt all night long!”
I was so painfully hard that I wanted to pull my hand out and fuck him right now, to bust my load in the only guy who’d ever been able to take me this far, but I couldn’t summon the will to stop barreling my hand in and out of his greedy ass.
Diego turned his head to me with that ravenous, insatiable desire in his eyes again. “Punch it,” he demanded. “Fucking punch it. All the way in, all the way out. Punch my fucking hole.”
I pulled out of him, strings of the thick J-Lube dripping off my hand, his hole gaping wider than I’d ever seen one gape in real life. I instantly plunged my hand back into his ass, the whole thing easily sinking all the way inside him.
“Yeah!” Diego grunted. “Just like that! Punch me! Punch that fucking pussy!””
I quickly drew my hand all the way out of his hole a second time, encountering no resistance at all as I easily buried it again. Sweat was dripping down my forehead as I worked into a rhythm, effortlessly thrusting in and out, Diego’s hole loudly squelching as he blissfully moaned.
“Oh my god!” he shouted. “Fuck yeah! Fucking punch it! Destroy my cunt with that huge hand!”
I’d fantasized about doing this for years, and now I was actually doing it. Diego was taking my massive hand like it was nothing and constantly begging me for more, his big brown ass infinitely hungry.
He looked back at me, the pleasure obvious on his face. “Hold it inside me for a second,” he panted. “Just a little break.”
I paused my onslaught, Diego’s body lifting up off the couch, his hands resting on his thighs. He turned his head toward me, our faces closer than they’d been all night, and I knew exactly what he wanted as his brown eyes stared into mine. I wrapped my free hand around his head, the other still resting inside his ass, pulling him into me so that our lips could unite. I felt his heartbeat on my fingertips as we kissed, the sparks flying everywhere as he shoved his tongue into my mouth. I started slowly punching his hole again, stopping short of withdrawing all the way, Diego moaning into me as our tongues passionately thrusted together, as I tried to bury myself as deep inside his mouth as I was in his ass right now. He pulled away after a minute of the most intimate making out I’d ever experienced, lifting his poppers up.
“You want some?” he asked, his eyes still lustful, still desperate for more.
I’d only done poppers a handful of times trying to fist a bottom, worried I was going to hurt them being too enthusiastic about getting in their holes with my horniness totally unleashed, but I knew he could handle that. “Yeah, sure,” I answered.
Diego unscrewed the cap and held the bottle up to my nose, his thumb pressing down on one of my nostrils. He let go after a few seconds, switching sides as I sniffed again. Pulling the bottle back from my face, staring into me, he looked hungrier than he had all night as he settled back into the couch and sniffed the poppers himself.
The high of the poppers washed over me listening to him inhale, more blissful than it had ever felt knowing that I was finally living out one of my fantasies. I heard the cap screwing back on with my hand still gently moving in and out of his hole. For the first time since he’d requested a break, I pulled it all the way out of his ass and quickly shoved it back inside, finding him looser than ever after the kiss.
“Harder!” Diego begged, his face falling into the cushion. “Punch that fucking pussy out!”
Feeling the intense rush of the poppers, fisting his ass was hotter than it had been all night, and I was relentless, forcefully pistoning my whole hand in and out of his butt. Diego’s moans grew more and more ecstatic until he was almost screaming, his ass finally yanking away from my hand.
He grunted, the glistening, perfectly arranged red petals of the biggest and most beautiful rosebud I’d ever seen in real life sitting just beneath his wide, circular gape. Violent gushes of piss loudly splashed out all over the towel and couch beneath us. “Oh my god!” he yelled.
“Holy shit,” I mumbled as his insides finally withdrew, his hole closing up again. I’d seen a mini-rosebud on one of the guys I’d tried to fist, a decent one on the twink from Rogers Park who had driven me there and taken my hand a few times, but Diego’s bloom was infinitely more impressive, absolutely stunning and totally incomparable. It was a distant fantasy suddenly and immediately realized.
Diego glanced back at me, obviously still in heat. “How am I doing?” he asked.
“Fucking amazing!” I answered, my lubed up hand quickly finding my dick. “That was the hottest rosebud I’ve ever seen!”
He smiled proudly and I saw the determination to please me take over again. “Yeah? I want you to make it even bigger. Train me to push that rosebud all the way out. Fist my hole until I fucking prolapse.”
I smirked at him, pushing four of my fingers back into his ass and meeting no resistance at all his hole easily swallowed them to my knuckles. “You want more?” I asked, already knowing the answer.
Diego pushed his face back into cushion, arching his back and wiggling his hairless brown ass. “I need more,” he said desperately. “Punch that pussy out. Make me pissgasm all over the couch again and fucking soak it.”
I drew my fingers back, pouring more lube out on his ass from the water bottle and spreading it everywhere. I made the duckbill shape with my hand again, sinking my fingers into his silky insides, his ass taking me to the wrist like it was nothing. He was wide open and I knew he was ready for an even bigger challenge. I pulled out and clenched my fist, pressing it to Diego’s battered slit and pushing, the whole thing instantly popping inside his hole.
He groaned as he capped the poppers. “Punch it!” he begged. “Punch that loose boy pussy out! Make that rosebud fucking huge!”
I held nothing back, mercilessly punching Diego’s hole with my closed fist as he moaned wildly, strings of J-Lube flying everywhere as I pistoned in and out. “Fuck yeah, man. Your pussy is so incredible.”
He couldn’t even answer, a cacophony of incoherent sounds pouring out of his mouth when he tried, my closed fist brutally tearing in and out of his hole until I felt his ass literally trying to push me out.
“Hold it there,” he panted urgently after a few minutes of relentless punching. He took a few moments to catch his breath, lifting his body up again so that our faces were close together, insatiable desire and blissful ecstasy painted all over him. I guided him back to my lips for the second time, my clenched fist still lodged in his butt, pulling his face to mine so that we could kiss again. Our tongues were pressing together so fervently we made the first round of kissing look like an innocent peck on the lips. We devoured each other like we were both living in the most satisfying moment either of us had ever experienced, exchanging pure, unbridled lust.
Diego broke the kiss, panting as he held the poppers up to me, his eyes asking if I wanted to sniff again. I nodded and he held the bottle up to my nose, his thumb pressing my nostril down. This time he kept the poppers there longer before he switched sides, eagerly looking into my eyes before he returned to his original position, arching his back and presenting himself for more.
I felt the horny euphoria taking my mind over as he sniffed, hearing him twist the bottle cap back on.
“Punch my fucking pussy,” Diego pleaded, his voice subdued but still desperate after a huge hit of poppers. “Fucking destroy my cunt. Use me up.”
I yanked my fist out of his ass, instantly thrusting it back into his wide gape, everything else in the world totally irrelevant as the rush consumed me. He was literally screaming again as I violently punched his hole a couple dozen times
“Pull it out!” he shouted.
When I did, a trickle of J-Lube gushed out, a loud spurt of air escaping. Diego’s rosebud emerged again, even fuller than the first time, huge streams of piss loudly shooting out of his dick and pouring down all over the couch.
“You’re fucking incredible,” Diego breathed into the cushion. His hole finally closed up, his slit looking puffy and battered.
“No, you’re fucking incredible,” I said back, slapping his big golden cheeks with both my hands.
His whole body jumped and he was still panting. “Don’t stop,” he begged. “I’m so fucking hungry for more. Keep punching that pussy.”
I poured another round of lube into my palm, spreading it everywhere. I tried to press my clenched fist into Diego’s ass, but it wasn’t budging. I made the duck bill shape with my hand again, my fingers slipping into him until the widest part of my hand popped inside.
“Oh my god!” he grunted. “Your hand is so fucking big!”
Within seconds I felt Diego’s ass already trying to push me out, forcefully rejecting my massive hand. I let his body do it, Diego grunting as more piss sprayed all over the couch.
“Oh fuck,” he mumbled, still completely breathless. “I think I need a long break before I can take more. Is it cool if we just hang in my room for a bit?”
I grinned knowing that he wasn’t finished, rubbing one of my fingers against Diego’s wrecked slit. “Yeah, sure.”
He took another minute to recover, finally taking a deep breath and lifting himself off the couch. He smiled at me as he stood up. “Sorry I’m having to ask for a break so soon,” he said like he was actually apologizing.
I chuckled, shaking my head. “Are you serious? That was the hottest thing I’ve ever done in my life. I’ve never fisted a guy like that before.”
Diego looked pleased, and even used up, he still had that ravenous glint in his brown eyes. “I told you I could take it.”
“Yeah, and you fucking meant it,” I said. “That was amazing!”
He smiled and motioned for me to follow him, leading me into a tiny room that barely fit a twin bed. The apartment was huge, but the bedroom definitely wasn’t
“You know there’s still J-Lube all over you?” I asked, just before he was about to climb into it.
Diego waved his hand dismissively as he settled in his bed. “I’ll just wash everything tomorrow.” He looked expectantly at me, still hovering tall up above him.
I knew he wanted me to join him when he led me here, but now I really knew. I settled down beside Diego on the pristine sheets, and within seconds my arms were wrapped around him, my hard dick jutting into his lube-slicked crack. We’d just met and we’d only kissed each other twice, but after fisting Diego, after feeling his heartbeat on my fingertips, this felt perfect. This felt completely right.
“I don’t even believe you saying you’ve never done that before,” he whispered. “You’re really, really good at fisting.”
For a second I felt like he was just being polite, but I’d seen all the evidence showing how much he’d enjoyed himself. He’d pushed out the biggest rosebud I’d ever seen and he’d probably destroyed his couch uncontrollably pissing all over it. I laughed and kissed his neck, my hands gripping his body even more tightly. “I didn’t really know what I was doing after I got my hand in and you weren’t begging me to take it out. But you seemed to like it.”
“I fucking loved it,” he said resolutely, one of his hands tracing over mine, his fingers struggling to wrap all the way around it. “Damn.” Diego pulled my hand away from his chest, touching our palms together. “I can’t believe you just put this whole thing inside me. Your hands really are huge.”
I chuckled and kissed his neck again. “Hey, I warned you they were big.”
“Yeah,” he murmured. “I don’t think any guy has ever fisted me like that before. Seriously, you’re a natural. I’ve been getting fisted for a year now, but that–that was unreal.”
I was struggling to believe him after experiencing what he could take, finally living out my fisting fantasies, but I played along. “You’re the natural. I wish every bottom I’d met up with could have taken it like you just did.”
Diego pulled my hand back into his chest. “Well, now you finally know a bottom who can handle you.”
“Yeah,” I whispered. The urge to kiss him overwhelmed me as I drew my arms back and pulled away from him. He looked concerned at first, like he thought I was going to get dressed and walk out the door, but that anxiety instantly retreated as I guided him onto his back and slid between his legs. I loomed over him, my hard dick sliding against his slick crack as I looked into his brown eyes and recognized exactly the same desire. Diego wanted to kiss me as badly as I wanted to kiss him right now. I lowered my face to his and we made out again, both of us softly moaning into each other as our tongues tussled together. Lifting back, looking down at his lustful face, I recognized something else: he wanted to fuck as much as I did too. I pulled Diego’s legs up over my shoulders, firmly pressing my dick against his already lubed hole.
He stared straight into my eyes and eagerly nodded, his expression pleading for my cock.
I sank the head of my dick into Diego’s hole, all seven thick inches effortlessly gliding into his wet, battered ass. He definitely wasn’t virgin tight, but I felt his insides pushing hard against my shaft, almost trying to force me out.
“Oh my god,” he whimpered, his mouth gaping open, his brown eyes still locked on mine. “You used me up so much. I seriously feel like I’m taking your fist again right now.”
I grinned as I slowly sawed my dick in and out of his hole, feeling his ass trying to expel me with every thrust, piss freely gushing out all over his stomach and dripping down his sides. We literally fucked for two hours, a short rest between each of my three cum shots before we started kissing and I mounted him again. By the end, we were both drenched in sweat, the formerly pristine sheets spattered with lube, cum, sweat, and piss.
“I don’t think my pussy can take anymore tonight,” Diego whispered, adamantly shaking his head after I’d pulled out the last time. “I still want more, but you fucking used it up. I’m exhausted.”
I felt exactly the same way as we cuddled again, our bodies pressing together and our hands intertwining. “No worries,” I muttered. “I’m exhausted too.” All I wanted to do was pass out with him in his bed right now, cuddled up beside him, but I hadn’t brought anything I needed for work the next day with me. I let a few minutes pass, just contentedly holding Diego, when I felt myself slipping, almost passing out. I knew I had to let him go. “Hey, I have to work in the morning,” I said groggily. “Maybe I should start heading back home.”
Diego instantly let me go. “Oh yeah, sorry I got so comfortable. You just felt so good.”
I chuckled as I forced myself to stand up. “You’re fine,” I said, looming over his spent frame in the bed. “If this was a Friday night I think we’d be getting brunch together somewhere around here tomorrow morning.”
He smiled at me, stretching his arms up and running a hand through his hair. “Yeah, that would have been nice.”
“Maybe next time,” I said, our eyes locking for a second before I trudged back to his living room. I didn’t want to leave, but I knew I had to as I pulled my shirt on and hiked my boxers and sweatpants up my legs, Diego joining me there still completely naked. “You need any help cleaning up?” I asked.
He gently shook his head. “No, I probably won’t even start doing that until after work tomorrow.”
“I mean, you know you’re probably going to have to burn this couch after what we just did on it, right?” I joked as I sat down on it and started tying my shoes. “We totally ruined it tonight.”
Diego shrugged and smiled. “Well, at least the cover is washable. I’m going to have so much laundry to do.”
“Hopefully it was worth it?” I asked, looking up from my shoes and staring into him.
His satisfied eyes betrayed that it was before he could speak the words. “Yeah, that was definitely worth it.”
I was already replaying punching his ass in my mind, picturing his huge rosebud with Diego standing right there in front of me. “When we can we do it again?” I wondered. I needed to do all of that again as soon as I possibly could.
He looked hesitant. “I think my hole is definitely going to need a few days to recover after what you just did to it, but I’ll definitely let you know when I’m ready.”
I nodded. “Yeah, just let me know. I’ll be happy to make the trip back up here.” I stood up and grabbed my coat off the floor.
“I will,” he said with another smile. “Please don’t die walking over the ice back to the Red Line. I really want to see you again.”
I laughed as I buttoned up my coat. “Don’t worry, I’ll be super careful.” Standing next to the front door, looking down at Diego, I recognized what he wanted. I stepped forward, wrapping my hands around his head and pulling his face into mine one last time. He sank his tongue into my mouth as soon as our lips met, the two of us gently making out for a few moments before he pulled away.
“This really was amazing,” Diego whispered. “I’ll text you tomorrow?”
Seeing his face, hearing his tone, I knew his anxiety was bubbling up again. He wanted to keep kissing me, but he felt like he was imposing. “Hottest night of my life,” I said seriously, trying to reassure him. “I really can’t wait to do it all again.”
He smiled, seeming relieved. “Well, I hope you have a good night.”
I shot him one last grin before I walked out his front door. “After that? I already did! Get some sleep, man!”
Diego was still looking at me intently as I passed into the stairwell beyond his door. “I’ll text you,” he repeated. “Good night, Luke.”
“Good night,” I said, glancing at Diego one last time as I swung his door shut. I hated that I had to go home, that work was getting in the way of my real life, as I walked down the creaky stairs. All that chemistry, and now I had to leave just so I could show up in a suit tomorrow? Real life is miserable sometimes.
I’d experienced incredible hookups in the past only to never hear from the other guy ever again, but climbing down the stairs of that building in Rogers Park completely exhausted and totally fulfilled, I knew that wasn’t the end. I’d unleashed something in Diego that night and he’d unleashed something in me; whatever it was, we’d never be the same. I felt absolutely certain that my life had suddenly changed forever as I pushed the front door open, stepping back into the frigid Chicago cold. I paused in the yellow courtyard before I started trekking over the menacing ice sheet again, adding Diego to my contacts. Pushing the gate open and stepping onto the ice, starting my walk back toward the Loyola station to venture home, I knew I couldn’t wait to see Diego’s name lighting my phone up again.
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