Intern begs boss to pound his lube-ready ass over the desk for a promotion.
Jamie hunched over his desk in the dimly lit office, the glow of his computer screen casting shadows across stacks of urgent reports. It was well past midnight, and the deadline crunch for the quarterly filings had everyone else scurrying home hours ago. Everyone except him and Mr. Harlan, the stern, silver-fox boss who ruled the floor like a king on his throne. At 25, Jamie was the ambitious intern with stars in his eyes—and a perpetual hard-on for the 40-year-old alpha who'd mentored him into this overtime hell. Harlan was built like a Greek god who'd traded his toga for a tailored suit: broad shoulders, chiseled jaw, and those piercing blue eyes that could make Jamie's knees buckle with a single glance.
The rumors about Harlan's cock didn't help. Office whispers painted it as a monstrous 9-inch beast, thick as a wrist, the kind that rearranged guts and egos alike. Jamie had jerked off to the fantasy more times than he could count, imagining that slab splitting him open right here on the copier. Tonight, with the office empty and the tension thicker than Harlan's rumored girth, Jamie decided it was time to turn fantasy into overtime overtime.
He'd prepped like a pro: a generous squirt of lube between his cheeks before leaving home, his hole already slick and twitching in anticipation. As Harlan strode by with a stack of folders, barking orders about double-checking the spreadsheets, Jamie "accidentally" knocked his water bottle off the desk. In the clumsy scramble to grab it, he hooked his thumbs into his waistband and yanked his pants down to his ankles, bending over just so. His bare ass cheeks gleamed under the fluorescent lights, lube-slicked and spread invitingly, his pink hole winking like it was begging for a performance review of a very different kind.
"Mr. Harlan!" Jamie gasped, feigning shock as he wiggled his hips. "I—I slipped! But while you're here... sir, please, I need that promotion. Review my... assets?"
Harlan froze mid-stride, his eyes locking onto the presented feast. A slow, predatory smirk curled his lips, the kind that said he'd been waiting for this exact brand of intern idiocy. "Jamie, you little slut. Dropping trou in my office? That's not how we file reports." He set the folders down with deliberate calm, stepping closer until his cologne—musky and commanding—filled Jamie's nose. One big hand cracked down on Jamie's right cheek, the spank echoing like a starting gun. "But damn if you haven't lubed up like a pro. Begging for it already?"
Jamie moaned, pushing back into the sting, his cock throbbing against his thighs. "Yes, sir! I've been dreaming of your thick cock ravaging my willing ass. Please, pound me over the desk for that promotion. I'm ready—hole's primed and everything!"
Harlan chuckled, low and dangerous, delivering another firm spank that jiggled Jamie's flesh. "Eager little intern. Let's see how you handle a proper probe." His thick fingers danced over the slick crease, teasing the rim before one dipped in knuckle-deep. Jamie gasped, clenching greedily as Harlan twisted and scissored, adding a second finger with a wet squelch. "Fuck, you're obsessed with this, aren't you? Anal slut through and through."
"God, yes!" Jamie ground back, riding the fingers like a desperate cowboy. "I confess—I'm an anal fiend. Can't cum without something wrecking my hole. Your cock's all I think about, sir. Please, I need it stretching me!"
Harlan growled, a rumble that vibrated straight to Jamie's core. "Overtime means earning it, boy. Get on the desk—spread wide." He yanked his fingers free with a pop, shoving Jamie forward. Papers flew everywhere as Jamie scrambled up, ass high and cheeks pried apart in desperate invitation, his lubed hole fluttering openly. Harlan loomed behind him, unzipping with a metallic hiss that made Jamie's pulse race.
The escalation hit like a freight train. Harlan's pants hit the floor, revealing tree-trunk thighs and—holy spreadsheets—that rumored monster: a girthy 9-inch cock, veined and angry-red, already leaking pre-cum like it had a personal vendetta. He stroked it once, smirking at Jamie's wide-eyed stare. "Like what you see, intern? Time to tumble and earn that raise."
They tumbled in a frenzy, Jamie's shirt the only casualty as Harlan ripped it open, buttons pinging like confetti. Desk cleared in a swipe, Jamie bent doggy-style over the edge, legs splayed, begging with hip wiggles. "Ravish me, boss! Make me your desk whore!"
Harlan didn't need more invitation. He slathered his beast with spit and Jamie's own lube, the fat head nudging Jamie's rim. "Here it comes, slut. Take every inch." With a hip snap, he breached, the girth stretching Jamie's hole to its limits in one burning, delicious slide. Jamie howled, half-laugh, half-moan: "Fuck, it's like filing a promotion deep inside! Thicker than my wildest Excel dreams!"
Harlan laughed, a booming bark, gripping Jamie's hips like handlebars. "Humorous little shit. Let's see you spreadsheet this." He ravaged forward, bottoming out balls-deep, the desk creaking under the assault. Deep, pounding thrusts followed—each one a hilarious symphony of skin-slaps, wet squelches, and Jamie's over-the-top commentary. "Oh god, sir, you're rearranging my intestines! Promotion feels so good—harder, file that cock report!"
Harlan obliged, railing him mercilessly doggy-style, the massive shaft dragging over Jamie's prostate like a bulldozer. Sweat slicked their bodies, the office reeking of sex and printer ink. "Tight as a vice, intern. Begging for it like this? You're getting that raise—after I breed this ass."
Jamie was a moaning mess, pushing back to meet every plunge, his own cock leaking a puddle on the desk. "Yes! Pound my lube-ready ass—I'm your promotion slut!" But Harlan wasn't done escalating. With a grunt, he pulled out—Jamie whining at the void—then spun the office chair around. "Switch it up. Ride me reverse cowgirl, boy. Show me how frantic you can bounce."
Jamie hopped on like a man possessed, straddling Harlan's lap facing away, that slick hole swallowing the girth in one greedy drop. "Fuck yes!" He bounced frantically, cheeks clapping against Harlan's thighs, the chair squeaking in protest. Harlan's hands roamed, slapping those reddened cheeks with rhythmic cracks—"Ride it, slut!"—before two fingers joined his cock, probing Jamie's stretched rim and zeroing in on the prostate.
The climax built like a bad office party gone wild. Jamie's bounces turned erratic, prostate milked relentlessly as Harlan finger-fucked alongside his pistoning shaft. "Gonna make you squirt, intern. Anal orgasm for the win!" Pressure coiled, Jamie's moans hitting cartoonish pitches: "Oh shit, boss, it's coming—filing cabinet explosion incoming!"
He shattered, ass clenching like a fist around Harlan's cock, a clear squirt of prostate fluid jetting from his untouched dick, splattering the desk in a messy arc. "Holy merger, I'm squirting! Promotion approved!" Harlan roared, slamming up one last time, flooding Jamie's guts with hot ropes of cum, the overflow bubbling out around his girth.
Panting and spent, they collapsed in a heap, Harlan's cock still twitching inside. Jamie grinned over his shoulder, bow-legged bliss radiating. "Best performance review ever, sir."
Harlan chuckled, easing out with a obscene slurp, Jamie's hole gaping like a satisfied O. "Damn right. You're promoted, kid—my new anal-yst. Weekly meetings to... review your assets." He reached into his desk drawer, pulling out a thick, ridged butt plug—clearly a desk toy souvenir. With a wink, he pressed it home, twisting until it seated snug, sealing his load inside. "Wear this home. Keeps the promotion fresh."
Jamie moaned at the fullness, standing on wobbly legs to seal the deal with a cum-smeared kiss, tongues tangling salty and sweet. "Weekly anal-yst duties? Sign me up, boss. I'll waddle home bow-legged but beaming."
They broke the kiss, both grinning like idiots, Jamie tugging up his pants over the plugged ass, already dreaming of next week's "meeting." Harlan straightened his tie, smirking. "Get out of here before—"
The office door burst open, the night security guard's flashlight beam slicing through the haze. "Mr. Harlan? Heard noises—everything okay? And who's... holy shit!"