Jenna made the bet with her boyfriend Mark on a Friday night after too many beers. “I bet you a hundred bucks I won’t let your buddy Ryan fuck me,” she said, laughing like it was all a joke. Mark laughed too and shook on it. They both knew Ryan was hot, tall, and always staring at Jenna’s ass when he came over. The bet was supposed to be easy for her to win because she was loyal. Or at least that’s what she told herself.
Three days later Ryan showed up at their apartment alone because Mark was working late. Jenna answered the door in tiny shorts and a tank top with no bra. Her nipples were already hard from the air conditioning. Ryan walked in like he owned the place and dropped his gym bag. “Mark said I could crash here tonight. Couch is fine.”
Jenna felt the bet sitting in the back of her mind like a dare. She poured them both whiskey. They sat on the couch and talked shit about work. Every time Ryan shifted, his thigh brushed hers. She didn’t move away. After the second glass she said, “You know Mark bet me I wouldn’t fuck you.”
Ryan’s eyes went dark. “Did he now.”
“Yeah. Hundred bucks if I stay good.”
“You gonna stay good, Jenna?”
She set her glass down and climbed into his lap without answering. Her shorts were so thin she could feel the hard line of his cock pressing right against her pussy. She ground down once, slow, and felt him twitch. “I’m already cheating,” she whispered.
Ryan grabbed her ass with both hands and squeezed hard. “Then cheat harder.” He yanked her tank top up and sucked one nipple into his mouth, biting just enough to make her hiss. Jenna reached between them, shoved her hand into his sweats, and wrapped her fingers around his thick cock. It was bigger than Mark’s, hot and heavy in her palm. She stroked him fast while he switched to her other tit, sucking until it stung.
“Get these fucking shorts off,” he growled. Jenna stood up long enough to shove them down her legs. She wasn’t wearing panties. Her pussy was already slick; she could feel it on her inner thighs. Ryan kicked his sweats off and his cock slapped against his stomach. He pulled her back into his lap but this time he lined himself up and pushed straight in.
Jenna’s mouth fell open. He stretched her wide on the first thrust, bottoming out so deep she felt it in her guts. “Fuck,” she moaned. “That’s cheating real good.” She started riding him right there on the couch, bouncing on his cock while he held her hips and met every drop with an upward slam. The wet sound of her pussy taking him filled the room. She was dripping down his balls already.
Ryan flipped them so she was on her back on the couch. He hooked her legs over his shoulders and fucked her like he hated her, pounding so hard the couch creaked. Jenna clawed at his back and begged. “Harder. Fuck me like you don’t care about the bet.” He slammed in balls-deep and stayed there, grinding his pelvis against her clit until she came, cunt pulsing around his cock, juices running down her ass.
He didn’t pull out.
He just kept fucking her through it, chasing his own orgasm. When he was close he pulled out, flipped her onto her stomach, and shoved back in from behind. One hand fisted her hair, the other smacked her ass red. “Tell me you’re cheating,” he ordered.
“I’m cheating,” Jenna gasped into the cushion. “I’m letting you wreck my pussy and Mark’s gonna lose his bet.”
Ryan came with a grunt, flooding her deep. He stayed inside until he softened, then pulled out and watched his cum leak out of her swollen cunt. Jenna reached back and scooped some onto her fingers, sucking them clean while he watched.
They didn’t stop there. Ryan dragged her to the bedroom, bent her over the dresser, and fucked her standing up until her legs shook. He made her ride him again on the bed, this time facing away so he could watch her ass bounce. Every time she thought he was done he got hard again and used her. By the time Mark’s key turned in the lock at 2 a.m., Jenna was on her back with Ryan’s cock in her mouth, cum and spit running down her chin.
Mark stood in the doorway. He didn’t look surprised. He looked turned on. “You lose the bet?” he asked.
Jenna pulled off Ryan’s cock with a wet pop. “I cheated on it. Hard.” She spread her legs so Mark could see how wrecked and full her pussy was. “You owe Ryan the money. Or you can watch him fuck me again and call it even.”
Mark closed the door behind him and started unbuckling his belt. Jenna smiled around Ryan’s cock and pushed two fingers into her cum-filled cunt, already planning how she was going to cheat on every bet from now on.
