My boyfriend, Ryan, loves making stupid bets.
Free cuckold community
Sign up now!
It’s always something dumb—who can shotgun a beer faster, who can eat the spiciest wings, who can last longer in a Call of Duty 1v1. Usually, the stakes are harmless. Twenty bucks. A round of drinks. Bragging rights.
But this time? Things escalated.
We were at his friend Drew’s apartment, the usual weekend hangout spot. Ryan and Drew had been trash-talking each other all night over FIFA, and the energy in the room was tense. Drew’s girlfriend, Naomi, was curled up next to me on the couch, rolling her eyes at their macho bullshit.
Then Ryan said it.
“Next goal wins. Loser has to watch the winner fuck his girl.”
The room went silent.
I should’ve been shocked. Mortified. But my stomach fluttered. Ryan was possessive—always glaring if another guy so much as looked at me too long. The idea of him offering me up? It sent a thrill through me.
Naomi smirked. “You’re on.”
Ryan lost.
Badly.
One minute, he was yelling at the screen. The next, Drew was pulling me onto his lap, his hands already under my shirt. Ryan looked like he wanted to punch something.
“You don’t have to—” he started.
“A bet’s a bet,” Drew interrupted, his fingers tracing my waistband. “Unless you wanna pussy out?”
Ryan clenched his jaw. “Do whatever.”
Naomi laughed, dragging him onto the couch beside her. “Relax. You can jerk off if it’s too much.”
And fuck, the way Drew touched me—like he’d been waiting for this. He bent me over the armrest, yanked my jeans down, and ruined me. Ryan watched, his cock in his hand, his face a mix of fury and arousal.
The worst part? I loved it.
Drew came inside me, and Ryan had to drive me home with his cum still dripping down my thighs.
The group chat exploded the next day.
Ryan hasn’t made a bet since.