The Teacher's Dirty Dare

Teacher catches his student jerking off in class, the student was dared by his friends to do it. The teacher smirking decides to join and jerks off with the student, stating whoever cums first loses

The classroom was quiet except for the faint squeak of a chair and the slow, deliberate sound of skin sliding on skin. The boy’s breath hitched, his hand moving under his desk, his eyes flicking between the open textbook and the half-hard cock in his grip. He bit his lip, trying to keep quiet—his friends had dared him, and he wasn’t about to back down. Then a shadow fell over his desk. He froze. Mr. Carter stood there, arms crossed, watching. The boy’s stomach dropped—until the corner of the teacher’s mouth curled into a smirk. "Keep going.” The boy hesitated, but Mr. Carter was already unbuckling his belt. He pulled his thick cock free, already half-hard. “New dare,” he murmured, stepping closer. “Whoever cums first loses.” The boy’s pulse spiked as Mr. Carter started stroking himself, his grip firm and rhythmic. The heat in the room thickened, the only sounds their strained breaths and slick, wet friction. The dare had just gotten a hell of a lot more interesting.

The boy’s grip tightened, his cock throbbing as he matched Mr. Carter’s pace. His eyes kept flicking between the teacher’s thick shaft—veins straining under flushed skin—and the slow, knowing smirk on the man’s face. Mr. Carter shifted his weight, his free hand braced on the desk as he leaned into each stroke. “Eyes on me,” he murmured. “Unless you’re scared of losing.” A shiver ran down the boy’s spine. His wrist worked faster, pre-cum slicking his fingers as he tried to focus—but it was impossible, not with the rough, hungry sounds of the teacher jerking off right in front of him. Then Carter stepped closer, close enough that the boy could feel the heat radiating off him. “Good,” he growled. “But don’t you dare look away.” The challenge sent a jolt straight to the boy’s cock. His breath came ragged, hips twitching as he fought the pressure coiling low in his gut. One of them was going to break—and he wasn’t sure if he wanted it to be him.

Mr. Carter’s pace intensified, his thick cock glistening under the fluorescent lights as pre-cum dripped down his shaft. The boy’s own hand moved faster, desperate to keep up, but he couldn’t tear his eyes away from the sight—the way the teacher’s abs flexed with each stroke, the way his breath hissed through clenched teeth. "Fuck," the boy gasped, thighs trembling as pleasure coiled tighter. Carter’s smirk deepened. He shifted his grip, thumb pressing hard into his slit before dragging down in a slow, punishing twist. "That’s it. Let me see you fight it." The boy’s back arched, his cock pulsing in his hand—he was close, too close, but so was Carter. The man’s strokes turned uneven, his hips jerking forward as a low groan rumbled in his chest. Then the boy’s breath hitched—his orgasm ripped through him, spilling hot over his fingers. Carter’s hand stilled, his own release just moments away. He exhaled sharply, victorious. "Told you you’d lose."

The boy slumped in his chair, chest heaving, his come streaked across his stomach. His skin burned under Mr. Carter’s gaze—half smug, half hungry. "Now clean it up," Carter murmured, stepping so close the boy could smell musk and sweat. He pressed his still-hard cock against the boy’s lips, smearing pre-cum there. "Unless you’re done?" The boy hesitated—then opened his mouth. Carter groaned as he pushed in, the wet heat swallowing him instantly. His fingers tangled in the boy’s hair, guiding him deeper, his hips rolling in slow, filthy thrusts. "Good," Carter growled. "Now keep your fucking eyes open." The boy obeyed, gaze locked on the man’s clenched jaw, the veins in his forearms as he fucked his mouth. Saliva slicked his chin, his throat working around every inch—until Carter’s grip tightened, his cock swelling as he came hard down the boy’s throat. When he finally pulled back, he wiped his thumb across the boy’s spit-smeared lips. "Next time, you won’t lose so fast."

The boy swallowed thickly, the heavy taste still coating his tongue as Carter’s grip loosened in his hair. His jaw ached, but the ache was nothing compared to the heat still pooling low in his gut—because the man wasn’t done. Carter’s fingers trailed down the boy’s neck, over his collarbone, then lower, skimming slick abs before wrapping around his half-hard cock again. The boy hissed, oversensitive but unable to pull away. "You think I’m letting you off that easy?" Carter’s voice was rough, his own cock still thick against the boy’s thigh. He squeezed—just shy of too tight—then dragged his thumb over the leaking tip. The boy shivered, biting back a whimper as pleasure sparked sharp under his skin. Carter leaned in, breath hot against the boy’s ear. "Gonna make you come again," he murmured. "And this time, you’re gonna beg for it." The boy’s pulse jumped. The words sent another jolt through him, his cock twitching in Carter’s grip. "Fuck—" The protest died in his throat as the man’s hand twisted just right, fingers slick with his own spend. Carter’s other hand clamped onto his hip, holding him still as he worked him ruthlessly. The boy’s fingers scrabbled at the edge of the desk, knuckles white. He was hard again already, his body betraying him, heat building too fast. "Look at you," Carter growled. "Can’t even fucking help it, can you?" The taunt burned, but the boy couldn’t deny it—not when Carter’s grip was relentless, not when every stroke sent sparks up his spine. His breath came in ragged gasps, thighs trembling. "P-please—" The word slipped out before he could stop it. Carter’s grin was feral. "Louder."

Carter twisted his wrist in a cruel, slow stroke, dragging the boy’s orgasm to the surface with brutal precision. The boy’s back arched off the chair, a ragged cry tearing from his lips as his cock throbbed in the man’s grip—spilling again, hot and helpless over Carter’s fingers. "Pathetic," Carter murmured, smearing the mess across the boy’s stomach. He didn’t let go, even as the boy twitched with oversensitivity, his breath hitching. "You’re already shaking." The boy’s thighs trembled, his chest rising and falling in shallow bursts. He didn’t trust his voice—not when Carter’s thumb was circling the head of his cock again, teasing the raw, sensitive skin. Carter leaned in, biting down on the boy’s earlobe hard enough to make him gasp. "One more," he growled. "And then you’re going to thank me." The boy’s stomach clenched. His cock was still half-hard, trapped between pleasure and pain, but the heat in Carter’s voice sent another wave of need crashing through him. "Y-yes—" he choked out, fingers digging into the chair. Carter smirked. "Good boy." His hand moved faster, squeezing just enough to make the boy whimper. The slap of skin filled the room, Carter’s own cock heavy and leaking against the boy’s thigh as he worked him toward the edge a third time. The boy’s vision blurred. Every nerve was on fire. "Say it," Carter demanded. "Fuck— *please*—" Carter’s fingers tightened. "Again." "Please, *please* let me come—" The boy’s voice broke as the orgasm ripped through him, weaker this time but no less intense, his thighs jerking as Carter milked every last drop from him. Carter finally released him, watching as the boy slumped forward, boneless and panting. He wiped his hand on his own thigh, then grabbed the boy’s chin, forcing their eyes to meet. "Now," he said, voice low. "Thank me properly." The boy swallowed, lips parted, still tasting salt and sweat. He knew what Carter wanted. His fingers curled weakly around the man’s cock. "Thank you," he whispered. Carter’s grin was dark. "Again." The boy leaned forward, tongue tracing the leaking tip as Carter’s grip tightened in his hair. "*Thank you,*" he moaned—then took him deep.

Carter groaned, thrusting deeper as the boy’s lips stretched around him, hot and eager. But then he pulled back, fingers tightening in that messy hair—just enough to make the boy whimper. "Not like this," Carter murmured, voice rough but softer now. He dragged his thumb over the boy’s swollen lower lip. "Turn around." The boy hesitated, pulse hammering, but obeyed, bracing himself against the desk as Carter stepped behind him. Hands slid down his spine, possessive but slow this time, tracing the dip of his waist, the curve of his ass. Carter’s touch lingered—almost tender—before his fingers pressed between the boy’s cheeks, teasing. "You want me inside you?" The boy shuddered, nodding. "Yes." A low hum of approval vibrated against his back as Carter’s body pressed flush against him, warmth seeping through skin. He reached around, stroking the boy’s spent cock slowly, coaxing it back to life with patient, filthy drags of his palm. "Gonna fill you up," Carter murmured against his ear, the words heavy with promise. "Make you feel it for hours." The boy gasped as fingers slick with spit pushed into him, working him open with a gentleness that burned worse than the ache of overuse. His knees nearly buckled when Carter’s cock replaced them, thick and insistent, pressing in with a slow, rolling thrust. Carter’s hands gripped his hips, holding him close as he bottomed out, panting against the boy’s shoulder. "Fuck—so tight." They moved like that—deep, unhurried, Carter’s arms wrapping around the boy’s waist, pulling him back onto every thrust. His lips traced the boy’s neck, biting lightly, sucking marks where they wouldn’t show. "That’s it," Carter growled, one hand sliding up to press over the boy’s racing heart. "Take it." The boy arched, moaning as Carter’s cock dragged against that sweet spot inside him, over and over. Pleasure coiled tight, and he reached back blindly, fingers digging into Carter’s thigh—*needing* him closer. Carter snarled, hips snapping harder, his rhythm faltering as he buried himself to the hilt. "Gonna come *inside* you—" The boy clenched around him, whimpering at the hot spill, Carter’s release pulsing deep. He didn’t pull out, just held him there, panting, their sweat-slick bodies locked together. Carter’s lips brushed his shoulder—almost a kiss. "Good boy."