Yes, she holds off

You watch the last slivers of sand in the hourglass tumble downward, but the sounds coming from Jen leave no doubt—she’s already right on the precipice.

Her fingers curl in Matt’s hair and her thighs quiver around his head, but the final grains drop and Chloe calls “Time.” Matt stops licking and Jen half-growls, half-screams in frustration.

“Well, looks like you lose, Matt,” Chloe laughs. “Let’s see what you’re hiding under those boxers.”

Matt flushes slightly. Jen takes a few moments to let her spasming muscles calm down before she sits up. She smiles and kneels before Matt, hooking her fingers into his waistband and slowly tugging downward. She takes her time, letting the waistband stretch over his erection. When only the tip of his penis is still being held down, she leaves it there for a moment and lightly tickles around the base of his cock. He lets out a breathy moan.

Then she pulls them down fully, letting his cock bounce around. She squeezes it gently, sliding her hands down to cup his balls. Leaving him rock hard and slightly leaking precum, she moves back to her seat.

He stands there a moment to collect himself before he spins the bottle again.