Pairing: Sam x Dean
Rating: 13+
Tags: first kiss, flangst, brothers being idiots
Word Count: 1.8k
Created for: @first-time-wincest-fest – Baby 11×04
Summary: On their trip to Oregon, Sam had been dropping some pretty big hints that he’s looking for something more in his life, someone else to share it with. Dean has always felt like they were that person for each other, and now it finally sounds like Sam is catching up.
He’s set up the table at the back of the library with a tablecloth, place settings, several courses of food – including a salad – even wine, because that felt classier than beer. He looks over his achievement one more time, gives himself a nod of satisfaction and grits his teeth. It’s now or never.
“Sammy!” Dean calls out, and he hears Sam change direction and move out of the hall and back towards the library.
“Dean?” he calls out questioningly, bounding up the few steps from the war room. Dean greets him with his arms out, standing over his masterpiece. Sam gives him a look like Dean’s standing there with a stick of dynamite – cautious, and ready to jump on top of a bomb for his brother if the situation calls for it. “What’s all this?” Sam raises his eyebrow as he steps closer to Dean and the fancy dinner.
“I- uh…” Dean realises with sudden panic that he hadn’t thought beyond ‘grand gesture’ to what he was actually going to say to his little brother once he’d made the gesture. How the fuck do you ask out your little brother? “I made us dinner,” Dean finishes lamely.
“I, um,” Sam laughs a little, clearly confused. “I see that. But what’s with the whole” –he waves his hands around– “Pretty Woman vibe?”
“Huh?” Dean glances around the table, unsure how a prostitute is related to what’s happening here.
“I just mean, this is a little classier than your usual burgers and beer,” Sam laughs, examining the table. “Is that salad?”
“Yes,” Dean smiles, proud of himself for that one.
“Dean, you hate salad. What’s going on here?” Sam is incredibly suspicious now – this is not how Dean planned on things going.
“Just, sit down Sam. Yeah? Eat the dang rabbit food.” Dean pulls out a chair for Sam, and now his little brother is looking around for some kind of big surprise, like he’s about to be pranked. But, after a moment’s more hesitation, Sam sits and lets Dean push his chair back into the table. “Wine?” Dean offers as he sits across from Sam and picks up the bottle of red.
“Uh, sure… thanks,” Sam is still on edge.
“Relax, man,” Dean sighs as he pours a generous measure into Sam’s glass. “I was just trying to do something nice. There’s no boogeyman hiding under your chair.”
“Sorry,” Sam grimaces, probably worried he’s upset Dean.
“Don’t be sorry,” Dean sighs, he really doesn’t know where he’s taking this anymore. “Just eat.”
“It looks really good, Dean,” Sam smiles reassuringly, holding his wine glass out, and Dean taps his own against it.
“Thanks, Sammy,” Dean smiles back.
They tuck into the salads that Dean spoons onto their plates while Dean starts making small talk; he quizzes Sam about what he was up to in town earlier, asks if he found anything interesting on his last run to the local university library a few weeks ago, asks what he’s watching on Netflix these days. He spends a good ten minutes trying to convince Sam to watch this new show he found the other day about street car racing with him after dinner.
“More wine?” Dean asks, already pouring Sam another glass – their third each, now.
“You trying to get me drunk?” Sam laughs, and Dean has a very clear flashback of a girl called Holly saying exactly that to him on a date once. He gives Sam a twitchy smile as he pours himself the rest of the bottle and Sam swallows a mouthful of wine much more vigorously than people normally do. “You are trying to get me drunk,” Sam says with astonishment. Sam glances at his wine, examines the table again – the candles, the checkered cloth, the nice plates and the silverware actually set out in the correct order. “Dean… what’s going on here?”
Dean gulps, deer in headlights. He still hadn’t figured out how someone is supposed to ask out their little brother – he had kind of been hoping Sam would just get the hint after all the stuff he’d been saying in the car last week about – ‘You don’t ever think about something? Not marriage or whatever. But … something? You know, with a hunter? Somebody who understands the life?’ What in the goddamn Hell had Sam been talking about if he wasn’t talking about this – about them. About the two of them doing something about whatever the hell this thing between them is.
Dean has been silent too long, and Sam is staring at him, clearly confused, and…
“Dean?” Sam questions and Dean gulps, and then Dean sees comprehension dawning on Sam’s face. “Dean…” Sam trails off, clearly grappling with the polite way to word what he’s trying to say. “Why are we on a date right now?”
“I, um…” Dean is caught in the headlights of Sam’s quizzical gaze, and he has no right to be caught off guard in this situation, he planned the whole damn dinner in the first place – but here he is. “Because…” –he sighs, scrambling– “I thought this is what you wanted,” Dean hedges his bets, not laying the depth of his own feelings out on the line just yet.
“Dean, um,” Sam tries to hold in a scoff but does a poor job covering it behind a fake cough. “Just… what the hell, man?”
“No.” Dean waves his finger between them, he is not letting Sam pin this all on him. “You don’t get to ‘what the hell’ me – what the hell were you talking about last week?”
“When?” Sam is perplexed.
“In the car!” Dean can’t believe Sam doesn’t remember, he hasn’t been able to stop thinking about his brother’s words since he heard them. “On the way to Oregon. All that settlin’ down crap! Finding another hunter and ‘not getting married’” –Dean’s air quotes are very aggressive– “but having something.” Dean raises his eyebrows accusatorially.
“Yeah… so?” Sam leans forward cautiously like he wants to check Dean isn’t having a stroke or something.
“So,” Dean feels like he’s explaining how crayons work to a three year old, “you were talking about this right? About whatever the hell it is we got goin’ on between us?” Sam stares at Dean, open mouthed, and Dean loses his annoyance with Sam and his confidence in his ability to pick up on Sam’s hints in one swoop. “You… weren’t talking about us.”
Sam’s face falls and he shakes his head at Dean forlornly.
“Well,” Dean nods to himself and his mostly full glass of wine catches his eye from its place on the table. He reaches for it and downs it as quickly as he’s able, taking a moment with his eyes closed to feel the swirl of the alcohol cloud his head just a bit more before he opens his eyes and goes for the spirits cabinet in the corner.
“Wait, Dean,” Sam reaches out as Dean passes him but Dean pulls out of his brother’s grasp, barreling towards the whiskey and the oblivion he knows he can bring on with it. “Dean,” Sam tries again, following him across the room.
“No, Sammy, don’t,” Dean can’t look at Sam, can’t see the pity that must be swimming in his brother’s eyes right about now.
“Dean, I’m not saying no,” Sam grabs Dean by the shoulders and spins him around, and Dean spins, bringing the whiskey glass and decanter with him. “I just– you surprised me is all. I wasn’t –” Sam backs up and runs his hands through his hair. “I made myself get over you.”
Dean’s head has been reeling since Sam’s ‘I’m not saying no’ and it takes him a little longer than he’s proud of to comprehend what Sam is actually saying to him.
“You made yourself get over me?” Sam gives Dean a little nod, his chest heaving. “Hang on” –Dean grunts, putting down the whiskey and crossing his arms– “when were you under me?”
“I don’t know, Dean,” Sam sighs exasperatedly. “Try my whole young adult life. So just – gimme more than thirty seconds to get back there, is all I’m saying.”
“Um,” Dean is absolutely stunned now, he wasn’t expecting to be turned down and then picked back up again in the space of five minutes. “Sure, uh, take,” he clears his throat, “take all the time you need, I guess.” Dean turns to grab his glass of whiskey, and when he spins around again, Sam is there, right in front of him, more negligent of personal space than Cas has ever been.
“Can I just,” Sam glances at Dean’s lips none too subtly, and Dean can see his throat bob as he swallows nervously. “I just wanna try something.” He leans down and kisses Dean softly, and Dean kisses back immediately but cautiously. If Sam doesn’t actually want to go through with this now, he can’t let himself fall any further. They pull apart after a moment, and Dean can feel Sam’s chest rising and falling violently against his.
“Wanna pour me one of those?” Sam’s eyes flick down to the glass in Dean’s hand.
“Uh, yeah, sure,” Dean nods, no idea where they stand after that, but he pours Sam a whiskey and hands it over to his little brother. Now, he’s just waiting.
“So I, uh,” Sam clears his throat and tries again, “I’m a little out of practice.” Sam grimaces, glancing up at Dean.
“Well,” Dean considers his options. It seems like Sam is giving this the green light. “What’d you say to that Piper chick last week?”
Sam lets out a barking laugh, then rubs at the back of his neck like he does whenever he’s embarrassed. “I uh, I asked if she wanted to see my car,” he admits sheepishly. Dean gapes at Sam, astounded that he would pull something like that after all the times he’s made fun of Dean for the exact same thing.
“Well, in that case,” Dean grins and grabs for a bottle of whiskey, downing what’s in his glass.
“You wanna come see my car, baby?” he holds a hand out to Sam.
“Ugh, please, don’t use the same nickname for me as your car,” Sam grimaces and downs his own whiskey, but gets up and takes Dean’s hand.
“C’mon, don’t be a bitch about it,” Dean laughs, pulling Sam along behind him towards the garage, and he smiles when he hears Sam whisper ‘jerk’ under his breath.
Write The Life You Want 
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