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2020-09-06
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Dean Winchester's Guide On How To Woo Your Brother

Summary:

Canon-divergent after S8:E23-Sacrifice. Let's just pretend Season 9 never happened, okay?

 

It takes Dean some time to realise he and Sam are kinda married. Now, the trick is to get Sam to realise the same. It's not like he can Google tips on 'How to win your brother over'. He's on his own. Awesome.

Notes:

For Kitty, who wanted domestic fluff, and Ship, who asked for a first kiss under the stars. I tried to keep it fluffy, guys, but the angst snuck in anyway. Sorry about that XD

(See the end of the work for more notes.)

Work Text:

  It was a few months of living in the bunker until Dean handed Sam a cup of coffee at the war table and suddenly thought, Fuck, are we married?

   He froze, one hand still wrapped around Sam’s mug. Sam frowned, fingers curled around the handle and gently tugging. “Dean?”

  Dean stared at him for a few seconds, then blinked. “Nothing.” It sounded like a squeak and he cleared his throat. “It’s nothing.” He escaped to his bedroom with the excuse of feeling tired. Once safely behind locked doors, he fell onto his bed and stared up at the ceiling.

  So, they were married. They made each other meals, shared hoodies and flannels, died for each other, talked to each other while one was in the shower, went grocery shopping together, doomed the world for each other, and now they weren’t just driving around in a car all the time, they had actually put down roots, which meant they were married. Great. Except it wasn’t really enough. It never had been.

  For years, there had been a weird, unspoken… Thing between them. A thing that had begun when Sam, 19 and angry and holding tickets to California, had just leaned in and kissed Dean. Dean, 23 and heartbroken, had kissed back and then let him go. The thing had stayed stagnant for years, even after Sam was back on the road. It was never the right time for them, one or the other thing always going wrong, one or the other outsider always carving out a space between them. So, Dean had buried the thing deep in the darkest places of his heart, then buried his heart under a mountain of the baser things in life.

  Maybe Sam had done the same. Maybe not. Who knew?

  The problem now was that Dean literally couldn’t have picked a worse time to have his revelation of being platonically married to Sam and immediately deciding he wanted to be actually married to Sam. He was still a little weak from the Trials, for fuck’s sake. Cas was human and living in the bunker with them. And who knew if Sam was over Amelia yet? They didn’t exactly talk about that stuff.

  So, how exactly was Dean going to breach the topic? Ask him out on a date? Just plant one on him? Simply drag him to the bedroom and tear both their clothes off? Court him?

  For about half a second, Dean entertained the idea of research. How to tell my brother that I want us to be a couple? probably wasn’t something the Internet could help him with.

  Dean sighed. Courting it was, then. Surely, the Internet could help him with that much.

  Three hours spent surfing the net proved him wrong.

  So, instead he drew up his own game plan.


   Step 1: Set the tone. Start off easy. Let him know something’s different, but don’t overwhelm him.

  That should be easy. Dean was a master of subtlety and subterfuge.


  Sam looked up from his laptop as Dean returned from his shower, smiling at him.

  Sam raised an eyebrow. “You okay now?” He asked. “You were acting a little bit weird last night.” Sam wasn’t going to admit it now, but he’d peeked into Dean’s room thirty minutes after he ran out. Dean had been absorbed in something on the laptop and Sam had chalked it up to nothing.

  Dean shrugged. “Nothing. Just felt tired. Watched a movie and fell asleep.” He sat down next to Sam.

  Sam blinked. “What is it?” He asked.

  Dean looked at him owlishly. “What?”

  Sam looked at the chair across from him, where Dean usually sat. He looked back at Dean, who was still waiting. “Nothing,” he said. It would be a little weird to ask why they were sitting side by side rather than opposite each other. He turned back to his laptop instead.

  After a few minutes, Dean leaned in closer, peeking at the screen. “Case?”

  Sam shook his head. “No, just reading up on lore. We don’t know a lot about the eastern mythology, probably a good idea to learn some stuff.”

  “Stuff like… The Greek pantheon being full of incest?”

  Sam choked on his own spit. Dean rubbed his back in sympathy, despite the shit-eating grin.

  Sam couldn’t even verbalise why he’d had such a violent reaction. There were just a few things they never spoke of, some concepts they refused to put into words. The i- word happened to be one of the more important ones.

  So, as soon as Sam caught his breath, he turned to glare at Dean. Except Dean didn’t look mocking anymore. He had a soft smile, the kind he only wore when he thought no one was watching. Except Sam was watching right now, but Dean didn’t seem to mind, just kept smiling at him like that, like… 

  “Why are you looking at me like that?” He blurted out, annoyance forgotten.

  Dean shook his head, eyes dropping away uncertainly. “Just wondering how we’re related,” he answered, almost flippant but with a note of wonder. “I’m bored, man, talk to me about that lore of yours.”

  Sam sighed internally at the deflection. One day, he told himself, he’d successfully break down every single one of Dean’s walls and get to the heart of him. For now, he turned back to his Mythology Weekly email and started talking about Ancient Egyptian beliefs.


  Okay, so maybe he wasn’t as subtle as he thought he was. Fine.

   Step 2: Flirt. Make him laugh, make sure he enjoys his time with you. Tease him, but don’t overdo it.

  Well, luckily, Dean was an expert in flirting and in making Sam laugh. All he had to do was put the two together, throw in a few compliments and he’d be golden. As soon as the right opportunity came along…


  They were supposed to be playing pool. Hustling got boring if they weren’t in need of cash and it was always more fun to play each other while trading insults.

  Except tonight, Dean was obviously looking to get laid, judging by the way he kept smirking over his cue stick at the slender brunette by the bar. 

  Sam thought he was entitled to a little annoyance. "Dean," he sighed. "Eyes on the game. Or I can go back to the motel."

  Dean just gave him an easy grin. “Or you can go talk to that redheaded chick by the corner. She’s been eyeing you all evening.”

  Sam rolled his eyes. “You promised me no flirting with chicks tonight,” he reminded, trying his best not to sound like a whiny pre-teen. “That’s why I agreed to even come to a bar in the first place.” It was the truth. Sam may not protest against Dean’s serial hookups, but he drew the line at actually watching him at work. There was only so much envy his heart could take.

  For a moment, Dean looked mildly contemplative. Then his grin changed, turned smoother. Turning fully towards Sam, he teased, “Aww, Sammy. You know you’re the only one for me.”

  Sam refused to blush. “I’ll believe it when I see it,” he shot back in good jest. He did believe it, more than anything else in his life. Girls or no girls, Sam knew exactly what he and Dean were to each other. Selfishly, he just… Wished they could be more.

  But Dean shook his head. “Obviously, I haven’t been doing a very good job,” he lamented. “Don’t worry, Sam. You’re still the prettiest girl I know.”

  This time, Sam did blush. He closed his eyes for a second, trying to at least appear unflustered. “Play the game.”

  “It’s your turn.”

  Seeing he was right, Sam forced his thoughts to change, lining up his shot instead. There was an easy shot that he might as well take instead of-

  The hand between his shoulder blades startled him, but the familiarity of it had him stay still, unbothered. “Don’t look now, Sammy,” Dean’s whisper was whiskey-smooth at his ear, lips brushing against the shell. “But that chick from before looks just a little interested. And jealous.”

  Sam resisted the urge to shiver. “The redhead or the brunette?” He asked, holding his position.

  “Both.”

  “Why?”

  Dean chuckled, sounding impossibly closer. “Cause they’d do anything to be in either of our places right now.” The pressure was suddenly gone. Dean’s voice rang out easy and clear when he spoke again. “Take the shot.”

  Needless to say, Sam missed. When he straightened, Dean handed him a drink. It burned going down his throat, but somehow, Dean’s scrutiny had more heat.


  Well, that had gone a lot better than expected. Dean had been half-expecting Sam to laugh him off. Best case scenario- he’d have flirted back, which was what Dean had been hoping for.

  But the trembling shyness and disbelieving confusion was almost better. At least it proved that Dean did have some semblance of effect on his brother. Now.

  Step 3: Treat him. Nothing too extravagant, because otherwise he’ll be suspicious.

  Well, this had to be the easiest one yet. Sam's birthday was coming up anyway and the way to a man’s heart was through his stomach, right?


  “Dean, you’re… That’s… I…”

  Dean looked at him oddly. “What?

  Sam stared at him, then at the frozen vegetables in his cart. “Those are vegetables.”

  “Yeah. I know that.”

  “You’re… Buying vegetables. By yourself. Willingly.”

  Dean sighed, sounding annoyed. “I know that too. What’s the problem?”

  Sam was not going to get an answer out of him this way. “Nothing,” he managed to say. “Just, um… I was about to get them myself. Now I won’t. Because you did.” He shook himself. “Come on."

  “Weirdo,” Dean muttered.

  Sam tried to put it out of his mind. He almost succeeded too, as he and Cas sat together in the library trying to figure out a way to get him back to full angel power. 

  "You nerds need some more alone time? Or can we have dinner now?"

 Cas peered at Dean, then at his own stomach. "I believe it's time to eat, yes," he murmured. With a frown, he looked up at Sam. "Does the hunger occur at regular intervals? Or randomly?"

  "Uh, depends on what your body's used to," Sam explained. "Dean and I can go long enough on a little food, because that's what we've been doing since we were kids…"

  The words trailed off and Sam was shocked into speechlessness for the second time that day. 

  "Vegetable omelets?" He whispered. He cleared his throat and looked at Dean. "You made vegetable omelets?"

  Dean nodded.

  "Are they secretly filled with sausages?" He asked. 

  "Sam, how could sausages even be stuffed into an omelet, for god's sake?"

  "You never make them!" Sam exclaimed. He glared at the food with mild suspicion.

  Dean sighed. When Sam met his eyes again, his lips quirked up into a smile and he mouthed the words, Happy birthday. 

  Sam couldn't help the sharp intake of breath. A quick look at his phone confirmed that it was, in fact, his birthday. He'd totally forgotten. And Dean hadn't said a word because he knew how much Sam hated making a production of the date. 

  There was a lump in his throat as he looked at Dean and smiled shakily in thanks. He couldn't even remember the last time either of them had celebrated a birthday. Why start now? 

  Sam kept staring at Dean, at the utter softness of his smile, the affection in his eyes, even though his words were being directed to Cas. Was Dean…? Did he…? Had something changed? 

  The second the thought crossed his mind, Sam pushed it out viciously. Dean was just taking care of him, probably because it hadn't been all that long since the Trials. 

  Yeah. That's all it was.


  Okay, now that had been an absolute success. Apart from those scary few seconds where Sam had looked ready to cry. 

   Step 4: Spend more time together, outside of the norm. Keep it casual.

  Okay, this might be a little complicated. Sam and Dean spent almost all their time together. Literally. What else was there?


  “God, I’m not even a little tired,” Dean groaned. "But you know, I don't wanna go out either. I mean, what the hell?"

  Sam chuckled. "I think it's called a midlife crisis," he offered as an explanation. 

  Dean scowled at him. "Fuck off. What are you doing, anyway? Still reading?"

  Sam shrugged. "Actually, I was thinking of watching a movie."

  Dean clapped his hands together once, getting to his feet. "Great. Let's have a movie night."

  Sam bit his lips. "Um, it's an art movie. You won't like it."

  Dean shrugged too. "I'm bored enough that I actually might. Come on," he wheedled. "I promise not to make fun of your terrible choices."

  Sam sighed. "Fine. Lemme get Cas and we'll watch it in my room."

  "Wait!" Dean exclaimed. "Uh… Can we just… Just you and me?" He ended the question in a mumble, eyebrows raised slightly. 

  Sam had never been good at refusing Dean anything when he asked like this, unsure and hopeful. "Sure," he said, holding back a smile. "But if Cas finds out we didn't invite him, you're the one explaining."

  Dean rolled his eyes. 

  To be perfectly honest, Sam fully expected Dean to get bored and leave. He was right on only one count. 

  After about twenty minutes, he became aware of Dean's weight leaning against his side. A glance confirmed that his brother had fallen asleep, his head tilted back on the headboard. 

  Sam couldn't help his smile this time. He wasn't going to admit it, but he missed sharing a room with Dean every night, missed the certainty that Dean was right there, within easy reach. He'd almost said something when they'd first moved in here, but Dean had been so ecstatic at having his own room that he hadn't had the heart. So tonight was kind of… Nice.

  But it got Sam thinking. What had been up with Dean lately? He was acting a little… Different. There had been the openly fond looks, his favorite meals more often, the flirting… 

  It gave Sam ideas. Ideas that had no business existing anywhere in his head. Ideas like pressing his fingertips to Dean's lips to check if they were as soft as he remembered. 

  It had been years, almost a decade since that one kiss before leaving California. They hadn't even mentioned it after that, had pretended like it never happened after they got back on the road. 

  Sure there were moments when Sam caught Dean looking at him too long, moments when Sam ran his fingers over Dean's skin a little too softly while patching him. But they were fleeting, little hiccups in their carefully constructed ignorance. 

  Never mind the fact that Sam couldn't help compare every woman he felt any interest in to the man he spent his whole life with, but was always out of reach. 

  Sam sighed to himself. Who was he kidding? Dean had just wanted to spend some time with him and here he was trying to read into it. 

  Gently, he adjusted Dean's form, making sure he was comfortable on the pillows. Then with a last longing glance, he turned the movie off and slipped off the bed. He'd just sleep in Dean's room tonight.


  Dean wasn't entirely sure if he should count this as a success. On the one hand, he'd woken up in Sam's bed. On the other hand, he'd woken up alone. 

  Honestly, he was starting to get a little nervous. Did Sam really not see what he was trying to do here? 

  A more terrifying thought struck him. What if Sam just… Didn’t feel the same way? It had been so long, after all, with too much crap piled up between them. What if he really had moved on?

  Dean closed his eyes, rubbing the back of his neck tiredly. He’d give it another few weeks. If nothing happened, he’d let it go, nurse his broken heart with whiskey and blood and sex, and Sam would never have to find out.

  Step 5: Appreciate him. Remind him of how much he means to you. Make him feel special. 

  This one was going to be the most difficult of them all. Sam believed compliments about as much as he believed Dean's promises of joining him for a run one day. Which was to say: not at all. 

  Dean frowned to himself as he idly trudged out of the room. When was the last time, life and death situations and impending doom notwithstanding, he'd genuinely complimented Sam?

  He couldn't remember. That wouldn’t do. 

  Dean felt a slight pang of guilt. He knew exactly how fragile Sam's sense of self-worth was. As bad as his own, for sure. 

  Right. Wooing or not, he had to at least try to change that a little.


  Sam tore the bloodied shirt off as fast as he could, the smell of it making him sick. One would think he’d be used to it by now. And he was, but… But it was Dean’s blood. And he needed it gone.

  Dean watched him from the bed, chest cleaned and bandaged. He’d protested against putting a shirt on again, the fabric against the bandages always making him itchy.

  Sam stripped and redressed within seconds, ready to keep vigil in case Dean tore the stitches in his sleep. He always tended to be restless after a hard hunt.

  “Sam,” Dean said quietly.

  Sam stilled, forcing himself to take deep breaths. Slowly, he sat on Dean’s bed, near his feet. Reaching out, he curled his fingers around his ankle, trying to find the pulse. “You’re such a jerk,” he muttered.

  Dean scoffed weakly. “What else is new?”

  Sam grit his teeth. “You can’t… I know the girl was in trouble. But that doesn’t mean you let yourself get hurt.”

  Dean looked incredulous. “Don’t kid yourself, man. We both know you’d have jumped in front of her just as fast if you’d been closer than me.”

  Sam looked away. “I just… You could have died today. I can’t… We got lucky tonight.”

  “Hey.” Dean’s foot twitched, nudging his hip. “Come on, Sammy. I’m fine.”

 Sam shook his head. “I can’t do this without you,” he whispered. He was shaking, he realized. They hadn’t had this bad an experience in a long time. Sam still felt jittery sometimes, aftereffects of Trial juice lighting him up from the inside, and it made him fear that he wouldn’t be able to move fast enough on a hunt one day. And Dean was constantly trying to martyr himself and… 

  “Sam?”

  “I can’t do this without you,” Sam said again in a rush. He swallowed immediately, closing his eyes. “You can’t… You have to be more careful, damn it. I can’t… I can’t.”

  Dean was quiet for a minute. When Sam managed to look at him again, he had a soft look of realization on his face.

  “What?” Sam asked.

  Dean just shook his head. “Come here, you sap,” he muttered fondly.

  Sam hesitated for a second, then slowly shifted to lay down next to him, carefully keeping an inch or so of space between them. “I need to keep an eye on your stitches,” he mumbled.

  Dean rolled his eyes, turning his head to face him. “You’re right next to me. I’ll be fine. Go to sleep.”

  Sam tried. He really did. But Dean’s even breathing and his own exhaustion combined- his eyes slipped close within minutes.


  Dean woke to the effects of the pain meds just beginning to wear off, enough to make him slightly uncomfortable. Wonder of wonders , he thought wryly, noticing his bandages were still in place. Usually, he tossed and turned a lot after bad hunts.

  Still in the process of waking up, it took him a second to realize that there was a heavy arm slung across his hips, a leg thrown over his calves, and a solid warmth pressed across his side, effectively keeping Dean pinned on his back.

  Dean took a deep breath, before risking a glance. Sam was still asleep, his face smoothed out and lips slightly parted. Unable to help himself, Dean slowly wriggled a hand free. It was an awkward twist but he managed to gently flick away the hair fallen across Sam’s face.

  Sam twitched at the caress, eyes fluttering open just as Dean quickly withdrew his hand. Their eyes met and Dean simply wasn’t awake enough to hide the soul-deep ache, the desperate longing, the sheer want that he knew was written all over his face.

  His only consolation: Sam was looking back at him the same way.

  “I can’t do this without you either, you know,” he whispered without thinking. “It’s you and me, I meant that. I don’t know what I would do.”

  Sam’s lips quirked slightly, like he wanted to argue.

  Dean really didn’t want to hear it.

   Step 6: Increase physical intimacy.

  Dean found Sam’s hand from his hip, interlocking their fingers together in a way he never would have even with any of the numerous women he’d been with. Sam’s gaze dropped to the bandages. His thumb stroked the back of Dean’s knuckles. Turning slightly, his lips grazed across Dean’s bare shoulders in a deliberate move, testing, checking. Dean took a shaky breath, waiting, hoping…

  The phone rang.

  Sam jumped, bolting upright. There was a semblance of fear and shock in the tense line of shoulders. Dean felt his heart sink.

  If this was the universe’s way of telling him “It is never going to happen’ , then Dean was sorely conflicted between giving up and flipping the universe off.


  Things went back to normal. Sort of.

  Dean still cooked his favorites more often, happily split their movie nights between Westerns and art films, still touched him more softly, more often.

  But he stopped flirting, he never fell asleep besides Sam again, and the little touches were unconsciously bestowed, until Dean would seemingly check himself and back off. Sometimes, he’d get distracted from whatever he was doing and just stare at Sam, something like heartbreak flickering over his face for a few seconds before disappearing.

  Sam was a smart guy. Smarter than average. He was just a little slow on the uptake sometimes, when it came to the important stuff.

  He was starting to understand what Dean had been trying to tell him, to show him. He was starting to be able to be able to decipher the looks and the caresses and the smiles.

  And when Dean absently reached out to tuck Sam’s hair behind his ear, before snatching his hand back, looking horrified- Sam was stuck between the desire to laugh and the urge to bash his head against a wall. How could they both have been so stupid? Why the fuck had they wasted so much time when they’d literally been on the same page since forever?

  “There’s a meteor shower tonight,” Sam spoke up randomly. “It’s only a couple hours of road. Wanna see it?”

  He didn’t take his eyes off his screen, but he could almost hear Dean thinking, weighing the pros and cons of star-gazing. “I guess,” the answer came cautiously. “Why the sudden interest? We’ve never gone out of our way for this before.”

  Sam shrugged. “Yeah, but it’s been so long. Plus, this is supposed to be one of the best meteor showers ever and it only happens once every eighty years.”

  Dean snorted. “Figures you’d be into this stuff. You sure you’re not secretly a girl, Samantha?”

  Sam took a careful sip of his coffee, meeting Dean’s eyes over the rim of the mug. “I’m sure, but if you want to check or something…”

  Dean didn’t quite spit his coffee out, but it was a close call.

  Sam chuckled quietly and got to his feet. “Come on. We should leave in a few minutes if we want to be in time.” He patted Dean’s shoulder as he passed him. And if his fingers trailed over the side of his neck? Well…


  Dean lay back on the hood, alternating between staring at Sam and staring at the sky. They’d been here for around twenty minutes, waiting for the meteors, idling the time away with stupid games.

  “Simon Says you should try to do a keg stand.”

  Dean had enough alcohol in him to giggle. “Simon Says you’re an idiot if you think I’m gonna do that out here.”

  Sam frowned, looking down at him. “That’s not how the game works.”

  “Sure it does.”

  “I’m not ten, Dean, you can’t just tell me something stupid and expect me to believe it.”

  Dean pretended to think. “I don’t know, man, the Easter Bunny obsession lasted till you were twelve.”

  “Eleven!”

  “And a half.”

  “Fuck off.”

  Dean just laughed.

  They stayed quiet for a few minutes.

  Then Sam spoke up again. “Never have I ever been terrified of airplanes.”

  “That how you wanna do this?” Dean demanded. “Fine. Never have I ever tried to stab a clown soft toy.”

  “You put it on my pillow, it was the first thing I saw when I woke up, what did you expect?” Sam huffed. “Never have I ever gone skinny dipping.”

  Dean just gave him a lazy grin and a quick wink.

  Sam groaned, but there was a hint of something more as his eyes gave Dean a quick once-over.

  “Never have I ever hooked up with more than one chick in a town.”

  Sam sighed. “Fine.” He took a sip of his beer, then paused, half-formed words dying on his lips as something else seemed to occur to him.

  Dean felt a stab of concern. “Sam?”

  Sam swallowed, licking his lips slowly. “Never have I ever… Loved someone more than you.”

  The silence around them was weirdly complete, broken only by the sound of crickets and rustling wind. Dean couldn’t look at Sam. He was so not going down this road, no way, not when Sam was only going to drag everything out in the open. Either that, or it was pity, and Dean didn’t want either.

  “Dean?”

  “When’s the meteor shower starting again?” He asked. “Because, I swear, if you dragged me out here for nothing-”

  Sam was suddenly leaning over him, palms braced on either side of Dean’s head, hair hanging down to brush Dean’s jaw. Dean closed his eyes.

  “Sam,” he spoke slowly. “Stop it.”

  “You really want me to?” There was genuine curiosity there, an undertone of insecurity.

  It made Dean open his eyes again. “Sammy,” he pleaded, voice breaking. “Please…”

  “Why?” Sam asked in a whisper.

  Dean shook his head, unable to look away. “I tried… I’ve been trying. Kept trying to show you, you never… You didn’t-”

  “I’m sorry,” Sam interrupted with a wince. “Dean, I didn’t realize what you meant. You gotta know, man, come on, I…”

  Dean waited for a few seconds. “You what?” He asked.

  Sam didn’t answer. Instead, he leaned closer, lips brushing against the corner of Dean’s mouth.

  Dean’s breath hitched. He closed his eyes and tilted up on instinct. Sam kissed him gently, one hand cupping the side of his head to control it. Dean was more than happy to let him, content to savour the heat of their bodies pressed together, the rapid beat of Sam’s heart, the taste of beer on Sam’s tongue.

  When they broke apart for air, Dean decided that oxygen was entirely overrated. “You complete bitch,” he hissed half-heartedly to hide the teary tremble of his voice. “You dick! We could have done this so much earlier if you’d paid attention instead of keeping your nose in your books and your laptop.”

  “Hey!” Sam looked as indignant as one could while half-straddling someone. “You’re the one who decided to go about the entire courting process. Ever think that just laying one on me would have worked quicker?”

  Dean scoffed, hooking a foot around Sam’s calf. “I was being a gentleman,” he defended.

  “No, you were brooding.”

  “Dude, brooding is your thing. You’ve got it down to an art form. All I do is-”

  Sam didn’t let him finish, kissing him again, messy now, slow and wonderfully dirty. “One more thing,” he murmured, nipping at his lip. “There isn’t a meteor shower tonight. I lied. Just wanted a good view for this. Sorry,” he tacked on, sounding totally unrepentant.

  Dean gave a mock sigh, smiling up at the sky as he twined his fingers into Sam’s hair. “Whatever. It’s a beautiful night.”

  He could feel Sam’s grin against his neck. “And you call me the sap?”

  “Whatever,” Dean replied and pulled him back into another kiss.

Notes:

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