“That’s it,” he rasps, and slides his thumb inside my anus. Not all the way, just the tip, but my pussy clenches in response. I can feel how wet I am, how hungry my body is for more. He works his thumb in and out, slowly, then adds a second finger, stretching me, prepping me. The feeling is so strange I canhardly breathe; it’s like being hollowed out, made for something bigger.
He leans into my ear. “You’re my buttslut now, princess. You love Daddy’s fingers in your ass. Admit it. You’re my little anal whore.”
OMG, his words are so foul! But I can’t compute because my legs almost give out. Every muscle in my body contracts, shivering with a need I don’t understand.
He works me open, soft and patient, until I stop fighting and start pushing back with my ass, desperate to be filled. He lets go of my hair, uses both hands to spread my cheeks, and I feel the thick head of his cock line up against my back entrance.
“Oh my god, oh my god—unnnh!” I cry out helplessly as the huge monster penetrates my asshole.
He merely grunts and pushes forward, slow and relentless, the pressure mounting until it bursts into a sharp, sweet burn. I yowl, bite my own wrist to keep from screaming, but he shushes me.
“You love being fucked in the ass. That’s my good girl.”
He feeds his cock into me, inch by inch, until I feel stretched so wide I think I’ll split open. But then the pain fades, replaced by a deep, astonishing fullness. He lets me sit on his cock for a moment, adjusting to the size, then starts to move—tiny thrusts, gentle, letting me catch up.
I press my hands against the brick, desperate for something to anchor me, as he slowly drills my ass with long, smooth strokes. Every time he pulls back, I feel my rectum suction to him, clinging. He’s careful at first, then faster, rougher, pounding intome with the same savagery I watched through the crack in my dorm room door.
I’m moaning, gasping, lost. The dirty words pour out of him, fueling my fire:
“You’re Daddy’s anal whore, aren’t you?”
“You love getting your ass wrecked by a real man.”
“Such a filthy, hungry little bitch.”
Each one cracks me open, makes me needier, greedier. I want him to break me, want to be ruined in the dark by this stranger whose name I’ll never know.
At the very edge, he reaches around to finger my pussy, and the combination is electric—every nerve ending fusing into one white-hot supernova. I come so hard I see sparks, my body clenching on both his cock and his fingers, shuddering so violently I’m scared I’ll pass out.
“Ahhhh!” I scream. “Mmmmm!”
He’s at the peak too. The stranger groans, digs his teeth into my shoulder, and empties himself inside me with a series of savage, primal thrusts. “Fuck,” he bites out. “Fuck fuck fuck!”
I can feel the heat of his climax, the hot pulses of sticky jism in my ass, the pulse of his come shoot as he spurts again and again into my rectum.
“Fuck!” he bites out again. I moan headily, milking his thick cock with my anal walls, loving the deep penetration and the knowledge that I’ve pleased this man. It doesn’t make sense because I don’t even know him, and yet a warm rush of pleasure shoots through my veins as I moan headily, my pussy vibrating.
We stay like that for a moment, panting together in the blue-black dark. He pulls out, and I feel a hot, slick drip from my asshole and down my thighs. I reach for my jeans, dazed, and fumble my phone out of the pocket. Maybe it’s muscle memory, maybe it’s a fever dream, but I manage to snap a quick photo of his cock right as he pulls out. It’s dark and the snap’s probably going to be blurry, but so be it.
Thankfully, the man has no idea what I just did. He straightens his suit, buttons his fly, and tips my chin up with a single finger. “I’m glad we’re on the same page then. We’re two trains passing in the night, never to meet again. See you around, princess,” he rumbles, then vanishes into the dark like he was never there.
I stand there for a full minute, heart pounding, hands trembling, my insides redrawn around the memory of his size.
I don’t know his name. I don’t think I’ll ever see him again.
But I do know this:his cock was huge and I just won a thousand dollars.
I zip up, wipe my mouth, and walk back toward the dorm with my ass aching, still gaping from the deep penetration. Yet the night tastes new, dangerous, and full of possibility.
Maybe I’ll tell the girls tomorrow.
But for now, I’ll keep it for myself, a secret as dark and sweet as caramel.
3
TRYING TO CLAIM THE GRAND PRIZE
Andie
