“Do you know what this is?” Dean whispers in to Jack’s thigh, trailing his mouth over his skin until he reaches his hole, planting a sloppy kiss over it.
Jack fully shudders, face flushed as he pants softly. “M-My -” He can’t bring himself to say it.
“It’s your fuckhole,” Dean says, and it’s matter-of-fact, letting his stubble scratch against it. “And it’s where I’m gonna put my come. Because you want come, don’t you, Jack?” He kisses that pink fuckin’ treat again, sealing his mouth over it and sucking.
Jack arches up, screaming up, his cock twitching against his belly. “Dean - oh, God. D-Dean -”
“Tell me what it is, sweetheart.”
“There’s a good boy.” He hums, pressing his index finger in, crooking it upwards to just barely graze his prostate.
Jack wails; he’s got a leg up around Dean’s head now, flexing his thigh as he’s eaten out and fingered, hole getting sloppy wet from all the lube and saliva.
Sam - who’s been sitting in a chair on the other side of the room - saunters over to them, and gets on the bed. “Wanna see,” he says, and his voice is kind of greedy.
He peers down, taking in Jack’s pink, and then presses his own mouth to it, giving him a long lick.
Dean grunts, and gets back down there, too - and for a few minutes, it’s just the sloppy sounds of them eating Jack out together, occasionally kissing each other.
Jack’s a wreck, his cock red and wet, his belly so messy from pre-come. “Sam - Dean -”
Sam takes his cock into his hand, spitting on the tip before swallowing him down, and Dean gets to work sliding his tongue up the underside, keeping his finger firmly rocking inside him.
Jack can’t help it - he comes, and he comes hard, his small body bearing down on Dean’s finger, filling up Sam’s mouth, hot and sticky. He’s practically crying, writhing on the bed, muscles contracting wildly.
“Mmm,” Sam whispers, swallowing it all down, mouth a little messy.
Dean comes up, kissing the creamy remains off Sam’s face, and then goes up to push his tongue into Jack’s mouth, making him taste himself. “Oh, kid. You taste so good.”
Sam joins them, and soon, all three of them are exchanging sloppy kisses, Jack’s dick hardening again, red and swollen.
“Oh, there we go. Ready to go again. Next time you come, it’ll be with you stuffed at both ends.”