Title: Bets

Author: Wysawyg

Summary: Sammy likes to make bets. A series of vignettes from Wee!Chester to the end. Warning: Character Death. Gen.

Disclaimer: You know the rules. Dean doesn't belong to me. Sam doesn't belong to me. Even PapaWinchester doesn't belong to me. Neither does the Impala or the colt. It's all Eric Kripke and them fellas at the CW.

A/N: This is my first Supernatural ficlet but the Muse grabbed hold of my head and wouldn't let go, even when I threatened to pull Dean out've my head to blast it full of rock salt. Un-beta'd but hopefully I've caught any mistakes. I am a Brit so there might be a few cultural fluffs. Feedback please, criticisms welcome.

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"Hey Dean, I bet I can hold my breath longer than you can"

It had been another boring day in a crappy motel. Dad was out on a hunt or probably at a bar by now, nursing his injuries with a stiff whiskey and ensuring the Winchester Nothing Ever Hurts mask was firmly in place before he returned to his sons. Dean had run out of items on his 'Things to do to keep Sammy amused' list and was starting to get a bit desperate. There was nothing in this world worse than a bored Sammy. Dean had once suggested his father take a bored Sammy along on a hunt and watch the monsters run in fear. That comment had earned him a clip around the ear and Winchester Lecture #23 – Why hunts are serious business and not to be joked about unless you are dying and need to relieve tension.

Dean wasn't quite sure when Sammy had picked up this trait of starting every other sentence with 'I bet'. It was probably around Winchester Lecture #7 – Hustling pool and poker for profit. In the past few days Dean had had to endure 'I bet I can eat my food faster than you' which had left Dean with a severe case of heartburn even when the human hoover remained fine. 'I bet I can get into the motel before you' had left Sammy stuck on the inside of a locked door and no means to get the door back open. This latest challenge had Dean determined to win, if just for the memory of the lecture he'd earned from that. Winchester Lecture #1 – Protect Sammy. Always Protect Sammy. He didn't think there was an equivalent lecture for Sammy.

Unfortunately stubbornness was one of the keen Winchester traits, just behind monster ass-kicking and a predilection for emotional trauma. Dean knew he had the larger lung capacity, the swim team loved him though would probably not be so keen if they knew it was a result of charging through various woods, houses and graveyards to kill the things that go bump in the night. Sammy however was still not taking a breath and his face was reddening and Dean's hazel eyes could almost see a tinge of blue in the corner of his lips. Dean took in a breath and let out a silent sigh of relief as Sammy did moments later.

Sammy wins again.

"Dean, I bet I can name more cities than you can."

Dean quickly regretted having got Sammy that ratty old atlas for his birthday. Ever since then Sammy had been spending all the long journeys in the Impala naming every single city, town and tiny blip that they were about to come up to. His father had tried cranking the music up to drown out the boy's voice but somehow the sound of Sammy cut through even the thumping rock beat.

Dean tried just making up cities but Geek boy insisted on looking up every single one in his atlas and glowering at Dean every time that he discovered the lie though Dean was surprised to see Sammy grouchily nod once. Turns out there was a city called Intercourse. The look Dean got off his father however made that minor victory not really worth it.

There was one city both of them avoided mentioning. Apart from one day every year when their father got blind drunk and apologised repeatedly to his dead wife, Lawrence, Kansas didn't exist.

Sammy kept score. One hundred and thirty two to nineteen.

Sammy won again.

"Dean, I bet I can make Dad madder than you."

No challenge, Dean thought, the two of them had demonstrated a singular ability in the past few weeks… months… year to find each other's sorest point and then jab their finger right in.

Dean was never one to back down from the challenge especially if it meant sparing his kid brother from the patented Winchester glare for a while. It didn't take much to wind up his father. Drinking his bottle of scotch was a good start though the pleasant buzz in Dean's head gave way to a sick tension in his stomach and he didn't miss his brother's smirk as Dean made a dash to pay penance to the porcelain god.

That did give Dean the idea to flood the bathroom though. The old toilet wasn't exactly hard to clog, just a rolls worth of toilet paper and it was full to the brim with water. Of course, when Dean discovered that his stomach wasn't quite as empty as he thought it was, he quickly regretted that plan and forced a hand through vomit-swirled water to remove the wodge of paper. He'd barely gotten his arm out of the way before he puked again into the newly cleared toilet.

Dean's lucky streak continued when the bang of the door announced his father's return, the clink of glass proved he'd found the empty bottle of scotch and then the prickle on the bad of his neck told him his father was standing behind him. Dean tried to give his patented cocky grin but had to bend over the toilet once more to gift what felt like his entire stomach and part of his intestine into the bowl.

The long lecture on drinking during a hunt, drinking while looking after Sammy, drinking his father's scotch and generally on everything Dean had done wrong in the past few weeks had Dean certain that just this once, Dean would win.

Sam just gave his brother a cocky grin, Dean's own reflected back at him, and then pulled out a white envelope with the Stanford logo embossed on the front and presented it to his father.

Sammy won again.

"Dean, I bet you call first."

Sammy had never actually said that one but Dean could hear it in every beat of his heart from the moment Sammy walked out that door. It was the same as all Sammy's unspoken bets. I bet you love me more than I love you. I bet you need me more than I need you. I bet you can't protect me forever. And the one which had been beating staccato more recently 'I bet I can be normal'.

When Dean was completely honest with himself, he wanted Sammy to win that bet. He wanted Sammy to have a normal life, to get married to some stunningly attractive blonde who was far out of Sammy's league and that he could drive his brother nuts flirting with on the frequent visits. Dean would be uncle to two, no, three kids: two boys and a little sister that they alternated between making her life hell and protecting her so fiercely that nothing could get close. Unca Dean would tell stories of things which go bump in the night, never letting them know just how true the stories were.

But when Sammy had shown his Dad the letter, the choice had become so simple. His Dad or Sammy. A father who needed his help or a brother that wanted to be away from him. Hunting and saving people or tagging along behind his kid brother. Letting his brother be normal or dragging him kicking and screaming into a life that he'd end up resenting and hating Dean about. No choice at all really, even if his fingers kept twitching to the phone.

It's only after Dean drags Sammy away from precious Stanford and whips out his phone to warn Sammy of impending cop visits at the motel that he realises.

Sammy wins again.

"Dean, I bet I'll find this thing before you do!"

Dean didn't think Sammy actually meant that to be a bet, more another complaint as Dean closed Sammy's laptop, almost onto his brother's fingers, and insisted they went out to scout the location of the latest killing. Sammy had been sitting tapping away for the past hour and it'd been getting on Dean's nerves, he almost missed the silence broken by orders which characterised hunting with his father. Sammy just ignored his brother, opened up the laptop and kept tapping away.

When Sammy had first come back, it had seemed like everything was back how it'd been before Sammy had slammed the door and headed off towards Stanford. For all that Sammy kvetched about hunting, once they were out there, weapons at the ready, Dean could see the adrenalin rush in his younger brother's eyes and the way Sammy moved like a hunter. It felt like home.

But they'd always have to return to the motel and Sammy would retreat to his books and his laptop and his quiet snipes about their father and his brooding over the death of his girlfriend and there'd always be that look loitering on his face, the one that said 'I bet I'll be normal' and 'one day I'll leave you'.

Dean turned back to their father's journal, turning each page with the reverence it deserved. He knew this thing seemed familiar, they had discounted a black dog despite the similarities. Memories tickled the back of his mind but refused to give him any more information that the transfixing red gaze and then a brief flash of white.

Sammy's gleeful call brought Dean back to the present and he glanced over as his brother span the laptop to face him. Cadejo, of course. He and his father had faced once down in Mexico, Dean saved only by the timely arrival of a white Cadejo. What one was doing this far north was a mystery for another time. Fortunately it looked only to be a half-breed this time and Dean pulled out his knives, strapping them securely in easy reach as Sammy did the same. It felt like home.

Sammy winning again.

"Dean, I bet you can kill me in under ten seconds."

Sammy's voice was hoarse and the light humour he tried to inject just fell flat in the face of his brother's red-rimmed hazel gaze and the gun currently levelled at a spot perfectly between Sammy's black-threaded brown eyes. Dean felt his hand cramp and try to tremble, had he been anyone but John Winchester's best little Toy Soldier then the gun would likely have been shaking.

Dean could hear the footsteps getting closer. No idea if they were police, hunters or some more of That Demon's psychic foot-soldiers. Either way, they were cornered and as soon as those footsteps got close enough, Sammy was screwed. Dean stared into his brother's eyes and they begged him to help. Sammy's mouth opened to remind him of the promise made back in that freaky doll-infested hotel.

Dean pulled the trigger and forced himself to watch as his brother's empty shell toppled backwards, a half-smile looking so wrong on that vacant face. Eight point five seconds. He slid the gun into the back of his jeans and ran.

Sammy won again

"Dean, I bet you won't survive me long."

Sammy never actually said that but in the moment that his eyes dimmed, Dean could read the words as clear as day, written out in guilt.

Dean gave up betting and took up a new gamble: Russian Roulette with six loaded chambers.

Dean won this time.

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