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A Supernatural Bet

Summary:

The time Dean Winchester lost a bet.

Notes:

Just as a heads up this is the first thing i am posting EVER so be nice lol. Also, the OC is significantly younger then Dean, like at least 6 or 7 years in my head. ENJOY

Work Text:

It was a hot summer day in July. Andy and the boys were in a small town in Nevada that was having a ghost problem. They were quickly able to wrap up the case and were looking for a place to eat.

It had been 9 months since Andy had joined the boys on the road and about 5 since she and Dean had started dating and their relationship had been interesting to say the least. She would make fun of him for being old and dorky, taunt him about being a neat freak, and, after uncovering the Supernatural books, the leaked bonus chapters about angels, and finding out that there was fanfiction about the boys, Andy was a firm shipper of Destiel, mostly because it annoyed the crap out of Dean.

Dean always got her back for it though. He would make fun of her height and her nerdiness, make constant remarks about how dumb she was for a smart person, and play Pink Floyd in the car for hours. Andy has always hated Pink Floyd and would make sure to be extra obnoxious to Dean when she got her pay back.
Sam always got a kick out of their games.

Needless to say, they loved pushing each other’s buttons. At the end of the day though, Sam was glad they found each other. Andy had this energy about her that infected those around her and her constant optimism was good for Dean. She made him laugh and smile, she brought out the silly him and Sam loved seeing his brother this happy. Sam knew Dean deserved to be happy.

“Oh! Look! Giant bacon Burger! Go back, we’re eating there!” Andy bossed Dean from the back seat. Though she technically had girlfriend rights over the passenger seat Andy liked being able sprawl all her crap around in the back seat, Sam never mentioned it but she knew he was appreciative of it.

Dean made a U-turn and they went into the dinner. A hostess greeted them and quickly led them to a booth. Andy sat on the inside next to Dean and Sam sat across from them. Her eye was quickly caught by the bacon burger challenge.

“Hey Dean, wanna make a bet?” She asked her boyfriend wish a mischievous gleam in her eyes. His eyes looked down at her menu and he knew what she was thinking.

“Oh sweetheart, you think you can best me at eating a burger?” he smirked at her. Andy loved that smirk.

“Well then there’s nothing to be afraid of, unless, you know, you’re feeling like a little bitch today” she taunted

“You two are children” Sam muttered from behind his menu a small smile playing on his lips.

“Alright, name the stakes” Dean agreed

“Well, when I win, I get to drive the impala for as long as I want on the way back to the bunker” she stated

“No” he responded

“Why not? You scared you might lose?” she made a face at him

He glared at her “I don’t make bets involving baby”

“Oh please, if you can trust me with your life, I think you can manage to trust me with your car” she said

“Nope”

“Come on!” She begged

He sighed and rolled his eyes at her “Fine, but when I win, I want a home-made pie every day until the next case” He demanded

“Ok that’s-“

“Oh I’m not done” he cut her off. It was Andy’s turn to roll her eyes at him “As well as that, when I win, I also get whatever I want in bed for a week”

“And I’m done with this conversation” Said Sam. Andy laughed

“Fine, you’re on.” She said “But are you sure you can keep up with my sexual stamina, old man?” she added. And Dean stuck his tongue out at her.

“No really, can we be done with this conversation” Sam stated as he put down his menu. Lucky for him the waitress came over and the three of them put their orders in.
As they waited for their food Andy and the boys were talking about nonsensical things. It took about 20 minutes but Andy and Dean were more than excited when their burgers arrived. As usual, Sam picked the healthy option and got a wrap with a side of fruit instead of fries.

Dean turned over to his girlfriend “First to finish wins?”

“Fries included” Added Andy. The two of them took their positions and stared at Sam.

It took him a second but he knew what they wanted from him. He sighed and shook his head with a small smile “Read. Set. Go” and off they went.
Now, usually Dean is really good at shoving food into his mouth quickly. Andy had only beaten him a handful of times in these kinds of bets, and she had never even dared to make a burger bet since that was Dean’s favorite, but she desperately wanted to drive the impala so motivation was on her side.

Nearly 3 minutes later, two fists are thrown in the air. Sam looks up from his food to see Andy with the biggest smile he’s ever seen and he couldn’t help but laugh at the sadness and astonishment on Dean’s face as he realized he lost by 4 fries.

“HAHA! I win! I win! I win!” she sang and did a little dance in the booth

“No fair, you cheated, you had to have cheated!” Dean protested

“Yeah, I shoved the fries down my second throat as I ate the burger” she sarcastically rolled her eyes at dean. He was a sore loser, but then again, so was she. “You’re just mad because you’re bad” she added with an obnoxious hair flip just to spite him.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Dean looked miserable in the back seat of the impala.

Andy pulled something out of her backpack and Sam instantly knew why she wanted to drive. It was a cassette tape. The kind that had an auxiliary cord coming out of it so that you could play music from your phone/ipod/mp3 player in cars that only had cassette players. She flashed Dean one of her signature grins, the kind that meant she had been plotting this for weeks.

“What is that?” he asked. But he already knew what it was.

“Oh this? This is called pay back, babe. And I promise you it’s gonna be a bitch” she promised “You see, I’ve been waiting a long time to get to hear my songs in the car-“

“Your songs are crap” he interrupted

She turned to Sam “Hey Sam, remind me again, what are the house rules?”

“Oh, I think they were ‘Driver picks the music and shotgun shuts its cakehole’ so I guess that means back seat must have even less of a say” he responded. Dean was gonna kill him for playing on Andy’s side but he didn’t care because he knew what she was planning. He had forgotten about it since she started this up weeks ago but as soon as she pulled out the cassette tape, he knew this was going to be priceless.

“I hate both of you” Dean muttered from the back seat

“Oh cry me a river” Andy said unlocking her phone. “You know what, since I’m super nice, I’ll even let you choose what playlist you wanna hear first” she said sweetly.

“Classic rock” He said

Andy laughed “That’s real cute Dean but you can pick from ‘Songs About Destiel’, ‘Songs That Will Make Dean’s Ears Bleed’, or ‘The Musical Playlist of Musicals’. And keep in mind that there is a lot of overlap between the playlists”

Dean’s jaw dropped a bit and Andy’s hardly gave him any time to respond.

“Destiel it is!” She said as selected the playlist. She threw the car in reverse and backed out of the parking lot

“You’re an evil bitch, you know that right?” dean said, not at all pleased from the back

“Oh please, you know you love me” She winked at him and flashed a smile and they began their long journey back home.