I hooked up with this guy named Derek at a dive bar downtown. He was thick everywhere, shoulders like a linebacker, hands that swallowed mine when we shook. We barely talked. He bought me a shot, I told him my place was two blocks away, and we walked there with his palm already shoved down the back of my jeans, squeezing my ass like he owned it.
The second the door shut he spun me around and yanked my pants down. No lube at first. Just spit on his fingers and two of them jammed straight into my hole. It burned immediately, that dry stretch that makes your eyes water. I grunted and pushed back anyway. Fuck, youre tight, he said, voice low and rough. He worked those fingers in and out fast, scissoring hard, forcing my ring to open whether it wanted to or not.
When he pulled them out I heard the sound of his zipper. His cock slapped against my ass, heavy and hot. He didnt ask. He just lined up and shoved. The head popped past my rim and the rest followed in one brutal thrust. It hurt like a motherfucker. A sharp, tearing stretch that made my legs shake. I bit my forearm to keep from yelling. Derek didnt stop. He bottomed out, balls pressed tight to my taint, and started pounding right away.
Every stroke felt like it was splitting me open. His cock was too thick for a quick entry, veiny and ridged, dragging against raw tissue that hadnt been prepped enough. The burn was constant, a deep ache that radiated up my spine. Goddamn, youre gripping me, he growled, hands locked on my hips, yanking me back onto him. I could feel every inch battering my insides, the head punching past my second ring on the deeper slams. It hurt, but my own dick was leaking onto the floor, twitching with each painful thrust.
He pulled out halfway, spat on his shaft, and rammed back in. The sudden slickness made the next few strokes slide easier but the damage was already done; my hole was sore and puffy, clenching involuntarily around the invasion. Derek noticed. Hurts, doesnt it? he said, almost laughing. He slowed just enough to grind in circles, stretching the swollen ring wider. I nodded, breathing hard. Yeah. Keep going.
He flipped me onto my back on the couch, hooked my legs over his shoulders, and drove in again from a new angle. This position let him go deeper. The head of his cock battered my prostate with every thrust, mixing the pain with sharp sparks of pleasure that made my balls draw up. My hole felt wrecked, loose and used, yet still burning around his girth. Sweat dripped off his chest onto mine. He leaned down and bit my nipple while he fucked, teeth sharp, hips never slowing.
I reached down and felt where we were joined. My rim was stretched thin and hot around the base of his cock, puffy and slick with spit and precum. Every time he pulled back I could see the shine on his shaft. When he slammed home again I groaned loud, the hurt flaring fresh. Take it, he ordered. You wanted this dick. I did. I pushed my ass down to meet him, forcing more of that thick cock inside even though it made my eyes sting.
He changed rhythm, short brutal jabs that kept the pressure constant on my prostate while the shaft kept my hole pried open. The pain settled into a steady throb, background noise to the building pressure in my balls. My cock bounced against my stomach untouched, leaking steadily. Derek wrapped one big hand around it and stroked once, rough, matching the pace of his hips. The dual sensation, the deep anal ache and the tight grip on my dick, pushed me right to the edge.
I came first, shooting hard across my chest while my ass clamped down. The clenching made everything hurt more, the ring squeezing his cock like a vise. Derek cursed, fucked through it, and unloaded deep inside me. I felt every pulse, hot and thick, filling me while my hole still spasmed around him. He stayed buried until he softened, then pulled out slow. The drag made me hiss. Cum leaked out immediately, running down my crack onto the couch.
We stayed there catching our breath. My ass throbbed, sore and open, the skin around my hole tender to the touch. Derek ran two fingers through the mess and pushed some of it back inside. The intrusion stung but I let him. You took it like you needed it, he said. I nodded, already thinking about the next time Id let him wreck me again. The hurt was part of it, the price for how full and used I felt afterward.
