Rooftop Shift

The city lights glittered like scattered diamonds far below us, but all I could focus on was Jake’s hungry stare as he leaned against the rooftop railing. I’d been waiting tables at the rooftop bar for months, and Jake was that regular who always sat in my section, tipping heavy and flirting harder every shift. Tonight the place had closed early for a private event that got canceled, leaving just the two of us up here with a half-empty bottle of whiskey and the warm summer breeze tugging at my short black waitress skirt.

“God, you look edible in that uniform, Mia,” he said, voice low and rough. His eyes dropped to the way the white blouse hugged my tits, the top two buttons already undone from the heat.

I stepped closer, heart hammering. “You’ve been staring at my ass all night again, haven’t you, Jake? Every time I bent over to clear your table.”

He grinned, crooked and wicked. “Guilty. Been thinking about bending you over this railing since the first time you served me.”

The explicit heat between us snapped like a live wire. I grabbed his shirt and pulled him into a kiss that tasted like whiskey and pure want. His hands were on me instantly, sliding under my skirt, cupping my bare ass cheeks because I’d ditched the panties after my last break just hoping he’d finally make a move. His fingers found my already soaked pussy and rubbed my clit in slow, firm circles.

“Fuck, you’re dripping,” he growled against my mouth. “This wet for me all shift?”

“Yes,” I gasped, grinding against his thick fingers. “Every time you looked at me I got wetter. I need your cock, Jake. Right now.”

He spun me around, pressing my tits against the cool metal railing. The city sprawled beneath us, distant traffic humming like white noise while he yanked my skirt up to my waist. I heard his belt buckle clink, then the hot, heavy length of his big cock slapped against my ass. He rubbed the thick head along my slit, teasing my entrance until I was whimpering.

“Tell me how bad you want it,” he said, voice tight with lust.

“I want you to fuck me hard,” I begged, pushing back. “Fill this pussy while the whole city watches from down there.”

He thrust in deep on one stroke, stretching me wide. The sudden fullness made me moan loud enough that I worried someone on a lower balcony might hear. His cock felt perfect, thick and veined, pounding into me from behind in steady, powerful strokes. Each slap of his hips against my ass echoed softly in the night air. I gripped the railing, knuckles white, as he reached around to pinch my clit.

“Shit, your pussy’s gripping me so tight,” he groaned, breath hot on my neck. “So fucking wet I’m sliding in balls deep every time.”

I pushed back to meet every thrust, loving the way his heavy balls smacked my clit. The angle made his cock hit that perfect spot inside me over and over until my legs started shaking. He grabbed a fistful of my ponytail and tugged my head back so I arched harder for him.

“Don’t stop… I’m gonna cum,” I panted.

He fucked me faster, the wet sounds of my pussy taking his cock growing louder. My first orgasm crashed through me so hard my vision blurred with the city lights. I cried out, pussy pulsing and squeezing around his dick as waves of pleasure rolled up my spine.

Before I could catch my breath he pulled out, spun me to face him, and lifted me onto a wide lounge chair nearby. I landed on my back, legs spread wide, my soaked pussy open and glistening under the string lights. Jake shoved his cock back inside me in one smooth stroke, this time in missionary so he could watch my tits bounce with every thrust.

“Look at you taking every inch,” he murmured, eyes locked on where we were joined. He leaned down, sucking one of my nipples through the thin blouse while his hips kept that relentless rhythm. The new angle let him grind against my clit on every downstroke. I wrapped my legs around his waist, heels digging into his back.

“Harder, Jake. Fuck me like you’ve been dreaming about all those nights at my table.”

He growled and gave me exactly what I asked for, pounding so deep I felt him in my belly. Sweat slicked our skin, the scent of sex mixing with the night air and distant rain on concrete. My second orgasm built fast, tighter and sharper. I clawed at his shoulders, moaning his name like a dirty prayer.

“Cum on my cock again,” he demanded, voice breaking. “I want to feel you milk me.”

I shattered around him, pussy fluttering wildly. That finally pushed him over. With a deep groan he buried himself to the hilt and came hard, hot spurts of cum flooding my pussy. I felt every pulse, every thick rope painting my walls while my own orgasm kept rippling through me.

We stayed locked together, breathing hard, his forehead pressed to mine as the city hummed far below. After a long moment he kissed me slow and lazy, still half-hard inside me.

“Best tip I’ve ever given,” he whispered with a grin.

I laughed softly, clenching around him just to hear him hiss. “Next shift you’re sitting in my section again. And maybe we’ll try the storage closet after closing.”

“Deal,” he said, already starting to move inside me once more. “But I’m not done with you up here yet.”