Fisting Expedition in Rogers Park

"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.