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There was nothing left of the money.
It wasn't a situation that was unknown to Dean, he had lived his entire life by making everything out of nothing. Sam and him had been hussling pool and pertaking in credit card fraud since before either of them had been old enough to legally enter a bar or own a credit card.
Motel rooms had to be paid. Baby needed gas and maintenance. They needed food and clean clothes, sometimes new ones. Their gear needed to be repaired or replaced. Ingredients for spells needed to be bought.
There had always been something that had demanded a steady income of money without either of them ever really holding a proper job but they had made due. Somehow it had always worked out. Since finding the bunker their situation had loosened up a little, they had more resources to grasp from and secret accounts for the American Men of Letters for emergencies. After their troubles with the British Men of Letters they had even been given compensation, little as that made up for the friends they had lost and the hurt those bastards had caused them.
But as it stood the Winchesters had a rainy day fund now.
Which didn't mean that Dean didn't continue hussling pool, he may not need it anymore to feed Sammy until the next time Dad turned up from a job but it was still fun and an adrenaline kick when the case wave was running low.
Unless he found his wallet empty after he had side-eyed possible idiots to wring out of money roughly half an hour after stepping into the bar three towns over from Lebanon. Sam and Jack had been left behind in the bunker, Sam because he didn't want to go out and Jack because Sam had all but had an apoplexy when the kid had asked to be taken along. Cas had come along though, which Dean knew was more to keep an eye on him than for actual personal interest, Cas didn't like the seedy bars that Dean preferred for his rather illegal hobbies.
And he liked even less that Dean's usual suspects were rather the dimwitted bodybuilder type who could start raging so quickly.
But even those he could take apart tonight if he didn't have some money to begin with.
Where the fuck had his money gone to?
Dean was quite, basically dead sure that there had been fifty dollars left in his wallet when he had last looked into it yesterday... afternoon before he had driven into town with Jack and let the kid do the groceries because he had seen the local mechanic and had wanted to have a chat with him... dammit the kid. Tipped too much, was too nice and bought way too much candy. It was like Mini-Gabriel but nicer.
Grumbling to himself Dean dropped his jacket back onto the bench of the back corner booth he had pushed Cas towards after getting in to have the best overview of the whole place. Cas raised an eyebrow at him and Dean huffed before speaking, "the kid ran me out of money to get candy." He saw how Cas bit his lips to keep himself from laughing and scowled at him in response.
"Maybe you shouldn't always say yes to everything then," Cas proposed and Dean flipped him the finger, grabbing his bear to at least get buzzed when he couldn't get high on pool.
Fabric rustled and in the next moment Cas was holding out a twenty dollar bill to him.
"I'm not enthusiastic about supporting your question-worthy entertainment," Cas began, smile tugging at his lips despite the reproachful tone, fingers pulling the bill back when Dean made grabby hands for it, "but I'd rather see you happy tonight and not grumpy. And... I get a percentage of the winnings."
"Oh, who is condemning gambling now," Dean laughed and finally got to grab the money, Cas rolled his eyes and leaned back into the bench again.
"I'm not condemning gambling, I merely think there are more respectable ways of earning money," Cas argued and Dean snorted, finishing his beer before getting up.
"And where did you earn this money, huh?" He asked the angel while rolling up his shirt sleeves, Cas grinned, flashing white teeth.
"Helping Misses Rosenbaum with her groceries."
"Yeah, I'm gonna pretend I haven't heard that," Dean deadpanned and saluted Cas before walking off towards the pool tables. "Let's see then what Misses Rosenbaum's precious grocery helping money can win us."
--
"How much percent are we talking by the way?" Dean wanted to know a good hour later while he was counting his money at the bar after Cas and him had relocated there once bigger groups had come in.
"Twenty," Cas said very matter of fact and set his glass of something down, Dean had forgotten what he had last ordered, he wasn't wasted just slightly buzzed and hyped on victory.
"Twenty percent?" He responded in outrage though and hugged his many bills close to his chest, "are you out of your mind? I worked hard for this."
"You drank beer, played stupid and drunk and landed some trick shots, that's hardly working hard," Cas snarked at him and Dean was giddy enough to stick his tongue out at him.
"Still, twenty percent..."
"Without my money you wouldn't have been able to play in the first place."
"I would have found a way."
"You were pouting into your beer bottle when I got out the money."
"I do not pout." Dean argued back and abruptly stopped when he caught sight of the amused grin on the barkeeper's face. "Okay, fine. Take your damn money, you monster. Ripping off poor men who just want to have some fun." Cas took the offered bills and then good naturedly shoved Dean to the side, prompting Dean to grin at his current bottle of beer and grabbing the bar countertop to keep himself from falling off. "Come on, one last drink and then we're getting home. Pick our poison."
Cas waved the barkeeper down, "Whiskey neat," he ordered, pointing at the both of them, Dean grinned only brighter.
--
A few minutes later when they were sitting in Baby, Dean had no imminent desire to start driving, just wanted to enjoy the moment for a bit. Pockets full of money, pleasantly buzzed and warm and comfortable. He had spent a great night out with his best friend, had had fun and hadn't had to worry about a single thing for once.
"You good?" Cas asked quietly from the passenger seat after a good two minutes had passed without Dean starting the car. Dean rolled his head to the side and watched Cas in the dim light of the streetlight one car ahead of them. "Or do you need me to sober you up before you drive?"
"I'm good, Cas. Just... just taking in the moment, we don't get to do this a lot anymore." Dean told him and smiled after rolling his head slightly to the side where he was resting it on the back of the bench.
"It is a beautiful night," Cas agreed, looking out of the window at his side whereas Dean was offered up Cas' profile illuminated by the soft light of the street. And yeah, maybe he was a little bit more than buzzed to let those thoughts take root but he was so sick of always feeling down. They were getting a break from the shitshow that was their life and Dean was too old to not take it.
"Had a great time tonight, buddy," he admitted and Cas looked back around to him, had to glance down a little because Dean had sunk himself low on the bench.
"You did play a great many successful rounds, pissed off a lot of guys. I know you enjoy that." Cas pointed out, voice soft because he was letting himself have this moment, too, Dean could almost see how his angel was letting his walls down. A passing by car flashed its headlights over them and blue eyes seemed to burn so bright for a moment.
"Yeah but looking over and seeing that you were having fun, too, that kinda was the better part still," Dean confessed and Cas's smile could have lit up the car by itself.
Caught in the moment as he was it didn't take much for Dean to raise his right hand, curl it around the back of Cas' neck and then pull him down and closer until he could softly press their lips together.
"Are you..." Cas broke off his question as unsure as he had pulled back from the kiss after a short moment but Dean smiled and moved his other hand to gently slide his fingers into black hair.
"Yes, I am," he answered Cas and searched blue eyes for any sign of not wanting this but what he instead found was careful hope so he nosed at Cas' stubbled jaw until Cas tilted his head back down so he could kiss him again.
--
"Hi, guys. Bye, guys," Dean got out in a rush as he pushed Cas past the movie room, neither Sam nor Jack had any chance to pause their movie, let alone to turn around and get a glimpse of them. It wasn't like Dean would keep this new development secret from them but first of all he really wanted Cas to himself right now and secondly he wanted to spare Sam for one night what sure would come up in questions if Jack saw their rumpled state of dress.
He pushed Cas into his room, kicked the door shut with one hand and turned the lock with the other before advancing on who was undoubtly now his angel.
And his angel alone.