Cheryl's Return

When I was in college a black friend bet me he could seduce my girlfriend named Cheryl. He got her drunk and fucked her.

**The Bet** Cheryl laughed, tossing her blonde hair over her shoulder as she sipped her third vodka soda. The party was loud, sweaty—the kind where inhibitions melted faster than the ice in our red plastic cups. My roommate, Jamal, leaned against the wall, watching her with that slow, knowing grin. "I told you, man," he murmured under the music, just loud enough for me to hear. "She’s a sure thing." I scoffed, but my stomach twisted. My girlfriend was giggling at something he’d said, her fingers already brushing his arm. The bet had been stupid—*fifty bucks says I can get her into my bed tonight*—but now, as Cheryl leaned into him, her pupils wide, lips slightly parted, it wasn’t funny anymore. Jamal didn’t waste time. His fingers traced the curve of her waist, dipping just beneath the hem of her crop top. She shivered, but didn’t pull away. "You good?" he asked, voice rough. She bit her lip, nodding. "Yeah... just need to sit down." "Got you," he said, steering her toward the hallway, her steps unsteady. I should’ve stopped it. But I didn’t. The door to his room clicked shut behind them. I stayed frozen, listening—a low murmur, then the creak of his mattress. Cheryl’s breathy giggle turned into a gasp. Through the thin walls, I could hear it all: the wet slap of skin, the way her moans pitched higher every time Jamal drove into her. "Fuck, you're tight," he growled. She whimpered—not in protest, but *wanting* it. "Don’t stop," she begged. The rhythm got rougher. Faster. Jamal wasn’t holding back. My cock ached, pressed against my jeans. I should’ve been mad. Should’ve busted in there. But I just stood there, jaw clenched, imagining Cheryl’s legs wrapped around his waist, her nails dragging down his back. Then her scream—raw, unfiltered pleasure—cut through the music. A beat of silence. Then Jamal’s deep chuckle. "Damn, girl. You came *hard*." I exhaled, my fists tightening. Fifty bucks never felt so expensive. And the worst part? I couldn’t wait to hear it again.

--- The next few weeks blurred into a haze of sweat and humiliation—and *God*, I loved every second. Cheryl came back from Jamal’s room that first night with her lips swollen, her thighs sticky, and a dazed smile she couldn’t shake. "Did you hear me?" she whispered, still breathless, fingers trailing down my chest. "The way he *fucked* me?" I nodded, my throat tight. She laughed, low and wicked, before dragging me to my knees. "Clean me up," she ordered, spreading her legs. I obeyed, tongue dragging through her slick, tasting Jamal’s cum mixed with her arousal. She moaned, grinding against my mouth, her fingers fisted in my hair. "Fucking *pathetic*," she sighed, but the way her hips twitched betrayed her. Jamal didn’t stop at just fucking her. By the second week, he had her bent over the couch while his friends watched—some even took turns. Cheryl took their cocks like she was made for it, mewling as they stretched her open, her eyes rolling back when they came inside her. And after? She’d crook her finger at me. "Lick me clean," she’d demand, and I’d crawl over, my cock aching as I lapped up their mess. Jamal watched, smirking, as I swallowed every drop. "Good cuck," he’d taunt, palming the back of my head, shoving my face deeper. Cheryl’s moans were my reward. Pathetic? Maybe. But I never wanted it to stop.

Years later I married Julie. Six years after that we were at a party and Cheryl made friends with Julie.

The party buzzed with laughter and clinking glasses, but my stomach tightened the moment I saw Cheryl’s arm loop through Julie’s, pulling her into conversation. The years hadn’t dulled Cheryl’s smirk—or her effect on me. Julie laughed at something she whispered, her cheeks flushing, and Cheryl’s fingers lingered on my wife’s wrist. Too familiar. Too knowing. "You two know each other?" I asked, forcing casualness. Cheryl’s eyes flicked to me, slow and deliberate. "Oh, we just *clicked*," she purred, her thumb tracing circles on Julie’s skin. Julie giggled, leaning in. "She was telling me about this *crazy* college story—" Cheryl cut her off with a husky laugh. "Why don’t I show you instead?" Before I could react, Cheryl tugged Julie toward the guest bedroom, tossing a glance over her shoulder. Not at me—at Jamal, lounging by the bar. His grin widened. The door shut. A beat. Then Julie’s startled gasp. A moan. Jamal strolled past me, clapping my shoulder. "History repeats itself, huh?" He disappeared inside. The wet slap of skin. Julie’s breathy *"Oh God—"* Cheryl’s throaty laugh. My hands shook. My cock throbbed. And like always—I didn’t stop a damn thing.

The first time Jamal brought Julie home with cash stuffed in her bra, she couldn’t meet my eyes. Her lips were swollen, her thighs trembling—familiar signs. Cheryl lounged on the couch, smug as she peeled a bill from Julie’s cleavage. "Two grand," she announced, flicking the money at me like I was the hired help. "She’s a natural." Julie whimpered when Jamal shoved her toward the bedroom. "Go on, baby," he said, smacking her ass. "Earn your keep." The door barely shut before her muffled cries started—pleasure and protest tangled together. Cheryl tilted her head, listening. "She’s louder than I was," she mused, unzipping my pants. "You gonna sit here and stroke yourself like a loser, or are you gonna *watch*?" I followed her to the door, cracked just enough to see Julie on all fours, Jamal driving into her, her nails clawing the sheets. A stranger knelt behind her, waiting his turn. Cheryl’s hand wrapped around me, pumping in time with their thrusts. "Pay up, or she’s theirs all night," she whispered. I came in her fist, biting back a groan. Julie sobbed Jamal’s name as he filled her. And the stranger unbuckled his belt.

The stranger’s thick hands gripped Julie’s hips, his cock already glistening as he lined himself up behind her. Jamal pulled out with a wet pop, leaving her dripping—his cum leaking down her thighs as the new man wasted no time burying himself inside. Julie let out a sharp cry, her back arching, fingers twisting in the sheets. Cheryl tightened her grip on my cock, still slick from my release. “Still hard?” she murmured, her breath hot against my ear. “Guess that means you’re paying for another round.” Jamal chuckled, running a possessive hand through Julie’s hair. “Open your mouth, baby.” Her lips parted instinctively, her tongue licking at the tip of his cock before taking him deep. The stranger fucked her harder, his thrusts rough and uneven, grunting as Julie moaned around Jamal’s length. I could see it—the way her body trembled, the flush spreading across her chest, the way she gasped when Cheryl slid two fingers inside me. “Go on,” Cheryl purred, pressing against my back. “Tell her how much you love watching her take it.”

Julie’s breath hitched as the stranger’s grip on her hips tightened, his cock slamming into her with brutal efficiency. Jamal held her head steady, fucking her throat in a relentless rhythm, his thighs flexing as he pushed deeper. Drool trailed down her chin, her cheeks hollowed, but she didn’t pull away—just took it, eyes glazed and glassy. Cheryl’s fingers curled inside me, twisting, pressing—*owning*. “Say it,” she demanded, her free hand tugging my hair. “Tell her.” I swallowed hard, my voice ragged. “Fuck... I love it.” The words burned like shame but dripped off my tongue like honey. “Love watching you get used.” Julie sobbed around Jamal’s cock, her body jolting as the stranger bottomed out inside her, his balls slapping against her. The wet slap of skin, the creak of the bed, the grunts—all of it was too much, not enough. Cheryl’s nails dug into my scalp. “Louder.” “I *love* it,” I groaned, my cock twitching in her grip. “Love seeing you take every inch like you were made for it.” Jamal smirked, dragging his thumb over Julie’s swollen lips. “You hear that, baby? He’s *paying* to watch you break.” The stranger groaned, hips stuttering—no warning before he came, flooding her, his grip bruising as he held her in place. And Julie? She just whimpered, swallowing Jamal down like she was starving.