A/N: I've read a few different "drinking game" fics, and wanted to do my own take on one. Many thanks to the very patient RiverSongTam for her help on this story.
"Oh my god, Dean," Sam groans, flopping face down onto the bed. "We are not playing a drinking game right now."
Dean joins him on the bed, somewhat hampered by the large whiskey bottle in his hand, and pokes him in the ribs. "Why not?"
Sam swats blindly at him, pushing his face deeper into the pillows. "Because drinking games are only fun when you have more than two people," he retorts.
Dean sets the whiskey bottle on the bedside table, wiggles his hands under Sam's shoulders, and flips him over. "Oh, come on, Sammy," he breathes, leaning over him to press their lips together. "Never-have-I-ever made you do something that didn't turn out to be fun."
Smiling triumphantly, he sits up, grabs the whiskey bottle again, and shoves it in Sam's face.
"What?" yelps Sam. "What about that time—"
"Nuh-uh," says Dean, shaking the bottle under his nose. "You make me do all kinds of boring crap. At least with me, you're never bored."
Grudgingly, Sam sits up, uncaps the bottle, wraps his lips around the opening and drinks, his throat working in a long pull. Their eyes lock, and Dean flushes slightly, a small nugget of warmth heating his stomach, as though he's had a few swallows himself. He meant for them to be a little more buzzed before getting to the real fun, but he has no objections to starting ahead of schedule—so when Sam lowers the bottle slowly, considering, Dean closes his eyes and leans forward a little.
Sam is way ahead of him, though, ducking out of kissing range so that Dean's mouth meets the cold whiskey bottle instead, the glass clacking against his teeth. "Never-have-I-ever left food in the fridge till it got moldy!" Sam laughs, as Dean's eyes fly open again.
Normally this would earn him a cuff around the head, but now Dean just shrugs in acknowledgement and takes the bottle, deciding to let Sam win this round. After all, Sam's not the only one who can play dirty.
"If this game is stupid, it's your fault for not asking the right kind of questions," Dean says pointedly. He inches forward again, crowding Sam against the wall behind the bed, and lowers his eyes to Sam's mouth. "Never-have-I-ever turned down sex."
To Dean's satisfaction, Sam's fingers tremble slightly this time as he reaches for the bottle. His expression remains stubborn, though, and as soon as he's done drinking he fixes Dean with a narrow-eyed glare. "Never-have-I-ever worn women's underwear."
Dean opens his mouth, fully intending to deny that he has, either—rules of the game be damned—but he can't prevent his cheeks from flooding with telltale heat. Sam's eyes go wide, his mouth falling open in shock.
"Wait, you have?" He casts Dean a speculative look. "Did you like it?"
Dean clenches his teeth, grabs the bottle, and takes a large gulp. "Shut up, bitch. At least never-have-I-ever cried during sex."
Sam snorts. "Me neither."
Dean lets his voice go low and rough, the way he knows Sam likes it. "You did the first time." He grins a little, holding Sam's gaze. "If I remember right."
A small, choked noise is the only warning Dean gets before Sam's mouth is on his and he's being tackled back onto the bed, nearly spilling the whiskey. He chuckles as Sam straddles him, letting him lick his mouth open and thrust his tongue inside.
"Remember that?" Dean asks when they pause for breath, sitting up and running a hand through Sam's hair. "Made you come so hard you cried." He holds out the bottle. "You giant girl."
Sam accepts the bottle without protest, takes a healthy swig, and then pulls Dean's mouth back to his. "Never-have-I-ever taken someone's virginity," he pants against Dean's lips, barely pausing his kissing to let him drink.
Dean's pretty sure he makes some noises of his own as he kisses back, tasting the burn of whiskey on Sam's tongue. He's also pretty sure this counts as winning the game, and he is more than ready to move on to the next stage of the proceedings, but he can't resist one more round to drive his victory home.
"Never-have-I-ever slept with a married woman," he says. It's kind of a jerk thing to say, but then, the point of the game is to be a jerk.
Sam straightens abruptly, glaring again. "That's not fair. I didn't have a soul," he protests.
"Still happened," says Dean, unable to contain an amused smirk at Sam's annoyance. "Bottoms up, little brother."
Sam yanks the bottle from his hand and drinks. "Never-have-I-ever been so drunk I blacked out."
"I only did that once," Dean says, wincing. It was while he was fighting the Mark; he'd been trying to drink himself unconscious, trying to escape the rage that was consuming him, but instead he'd woken to a trashed motel room and blood on his hands.
"Still happened," Sam mocks. "Bottoms up."
Dean takes a long drink to quiet the memory, and then blurts out the next words that come into his head, not thinking beyond a desire to even the score. "Never-have-I-ever hit a dog with the Impala."
Sam flinches away from him. Belatedly, through the whiskey sloshing around in his brain, Dean realizes what he just said. "No—Sam," he starts, fumbling to grab his arm, "I didn't—"
But Sam is already lifting the bottle to his mouth. When he lowers it again, his jaw is clenched, lips tight. "Never-have-I-ever blamed you for trying to have a normal life," he spits.
Dean snatches his hand back. "You think I blame you for that?" he demands.
"I know you do," says Sam flatly, and okay, maybe Dean did, once, but he put all that to rest years ago in a dark, drafty old church, and the fact that Sam still doesn't believe it, even after everything he said then, is infuriating.
"Nah," Dean scoffs, as coolly as he can manage, "I got plenty else to blame you for. Like, uh...never-have-I-ever told you we weren't brothers." The words smart a little coming out, a much harsher burn than alcohol.
Sam seizes the whiskey bottle from where it's been forgotten, perched between them on the bed, but instead of drinking he shoves it at Dean, sloshing half its contents over the comforter. "Yeah? Well never-have-I-ever tricked you into doing something against your will," he hisses. Then, before Dean can say or do anything, he levers himself up and stalks away.
In the second it takes Dean to process what's happened, Sam is already halfway across the room, heading for the door. Dean doesn't waste any more time trying to figure out how the hell everything managed to fall apart so quickly; he just scrambles after Sam, his mind suddenly clear and focused on one idea: fix it.
"Sam, wait," he calls. Sam pauses in the act of reaching for the door handle, but doesn't turn around. Dean freezes a few steps behind him, afraid to move, as if Sam might spook and bolt like a startled horse. "That was a stupid game," Dean says quietly, after a few breaths.
"Yeah, I told you," Sam says, still with his back towards him. His voice sounds a little thick.
Hesitantly, Dean reaches out to touch his shoulder, groping for words, wanting to apologize, to tell him that whatever crap they've done to each other, none of it matters because...because….
"Never-have-I-ever stopped loving you," he whispers.
Sam turns to him then, finally, steps right up to him and loops his arms around Dean's waist, pressing their foreheads together as he whispers back. "Never-will-I-ever, either."
And that might not be forgiveness, exactly, not for everything, not yet—but it gives Dean hope.