Characters: Reader, Dean, John, Sam, asshole frat boys
Word Count: 1,762
Warnings: Hustling, grabby hands, asshole drunk frat boys, the feeling of being violated and uncomfortable of an older man’s hands on you, dean fluff at the end
Author’s Note: In this, the reader and Dean are 17 years old and Sam is 13.
“John, I’m not sure about this. This seems wrong.” You said, biting your lip hard. You looked at him and then at Dean who was across the bar and grill with his brother. John had brought you to a family bar and grill but he was on a mission.
Dean already knew this routine, that is why he was keeping his brother busy. John was teaching you how to hustle men in the game of pool. You knew how to play, thanks to Dean but you just didn’t know how to make yourself come across as innocent enough for much older men to underestimate you. You weren’t a confident girl as it was but John was persistent about this matter.
Hustling is how John made his money. Well, that and credit card fraud that he somehow never gets caught at.
“Y/N, sweetheart, you can do this. What is wrong, is those men who hustle other people. No one can do anything about it but you can. It’s okay.” John said from behind you. He handed you the pool cue and you crabbed it, biting your lip.
The bar was pretty empty for a Tuesday night which was good because that gave John a more open opportunity to teach you something other people wouldn’t like.
“Okay, fine, what do I do?” You looked back at John for help.
“First, the guys at the bar will most likely be drunk so their inhibitions are down. You have to act like you don’t know what you’re doing but in fact, it’s the complete opposite. You know how to play pool well and when they're drunk, their pool game will be off.
“Second, I know it will be uncomfortable at first, but, sweetheart, they will touch you. Don’t worry, because you’ll always be with me or Dean and you know we won’t let anything happen to you. Do you understand that?” John said, looking at you.
“Touch me how?” You asked, worry filling your eyes. You looked over at Dean since he made you feel safe and he caught your eyes. He smiled and nodded, giving you a wordless encouragement.
“Your ass for one thing. They’ll try and get you to come home with them. But that’s part of your routine. I know this sounds scary but it’s not. Would I let anything happen to you?” John said, asking a serious question.
“No, you wouldn’t.” John may have brought you into this life but he has never put your life on the line when it came to anything. Not yours, not Dean’s, not Sam’s. You trusted John and you nodded, determined to get this right.
“That’s my girl. Now, I won’t touch you but pretend that I am one of those men hustling other people.” John said, getting into character. You nodded and took a deep breath, getting into yours. You knew how to act. Years of watching TV have done that to you. Years of never leaving the motel room, you could only do so much to entertain yourself.
You went through everything, John’s helpful pointers and tips including his praises and words of encouragement were what got you through. You put up your pool cue when you were done.
“That was good, Y/N,” John said with a smile.
“Thanks, John.” You said with a smile. The bar’s door opened and you watched as a group of college frat boys came in, hooting and howling, going straight for the bar. You watched as one of them caught your eyes and winked at you.
“Okay, Y/N, this is your chance. Do you think you can do this one on your own?” John whispered into your ear.
“I think so?” You said, not confident at all.
“Let’s go sit by the boys. Let them have the pool table for a few games. Then you make your appearance.” John said, leading you over to where Dean and Sam were.
“Are we done here?” Sam asked, sighing. This wasn’t his scene at all and granted, he was only 13 years old but till.
“Almost, Sam.” John said, sipping his warm beer.
“Dad, are you thinking of sending her out there? By herself?” Dean said, getting protective of you.
“She’ll be fine, Dean. We are right here.” John said.
“Ask her that, she’s shaking.” Dean got up and walked to your side and put an arm around your shoulder.
“I’ll be fine, Dean.” You said, looking into his eyes. He sighed and nodded, not letting go of you.
“Alright, Y/N, get ready.” John said. You looked over at the pool table and saw some of the boys laughing with drinks in their hands as a poor man gave them their money. That sight alone was what made you get up. No one should be treating other people like that.
You looked at Dean and John with a nod and took a deep breath and walked over to them, seeming shy and distant which wasn’t a total act.
“Can I play?” You asked in a small voice.
“Are you sure, sweetheart? We wouldn’t want to break your pretty little heart.” The leader of the group smirked and walked closer to you. You took out the wad of cash John gave you to use. You had a job to do and you couldn’t afford to lose it.
“I have money.” You said, looking at the leader. You were much shorter than most of them and they smirked, knowing they would be able to beat you.
“Fine, you can go first.” The leader said, pulling out an equivalent wad of cash. You walked over to the table and placed the money down, the other man did the same thing.
“What’s your name, sweetheart?” One of the other men said, drinking his beer.
“Y/N.” You said shyly, grabbing a pool cue.
“Cute. I’m Pete and these are my friends, Slader, Flash, Blaze, and Mike,” The leader said, grabbing a cue. “What school do you go to?”
“Just the local high school. I’m a senior. I’m almost done with high school.” You said, preparing the balls.
“Ooo fresh meat.” You heard one of the guys say to another. You gulped, not knowing you could really do this and you looked at Dean from across the bar and he nodded at you. One look in his eyes seemed to calm your nerves.
“Don’t listen to them. Just break.” Pete said, watching your ass. You saw Dean get angry and you knew what Pete was doing. You bent down and lined your shot up but jumped when you felt a hand slap your ass.
“Sorry, my hand slipped.” Pete said with a smirk. Yeah, you definitely were going to beat their sorry asses. But you had an act to uphold. You shot the cue ball but missed and it wasn’t your turn anymore. Pete’s friends' snickers but didn’t say anything as you let Pete take his turn.
He made in a few stripped balls and then it was your turn again. This went on until there were more solid balls than stripped balls. Pete thought he was winning and you knew that you had to step up. You pretended to think about your move and once you got it, you bent down but froze a bit when you felt a pair of lips at your ear.
“Why don’t you, after this game, come back to our dorm? We could have a lot of fun.” Pete said, his hands going to your waist. It was a lie to say you weren’t uncomfortable but you hated how these men were. You had to put them in their place.
“Maybe. If you win, I’ll go back with you.” You said, taking your shot, managing not to hit him in the stomach. You made the solid ball and you got up to move around the table and bent over to take another shot.
“And if you win?” Pete said, smirking as he leaned on his pool cue.
“You stop hustling innocent people and get a life.” You said, taking your game up a notch and made your shot, hitting in two balls at once. Pete’s face fell when he realized what your game was. You smirked and made the rest of the shots, hitting the eight-numbered ball.
You stood up and set your cue stick on the table, walking over to the money and grabbing your stack and his. You placed them in your bra and turned to walk away but Pete grabbed your arm harshly.
“You think you can hustle me and get away with it? That’s my money bitch.” Pete said, pulling you into him. Your one cry for help that came out of your mouth was enough for John and Dean to be at your side.
“Leave her alone. She won that money fair and square and you know it.” John said, removing Pete’s hand from you. Dean put an arm around you and pulled you into him protectively.
“Where’s Sam?” You whispered, worried for the younger Winchester.
“Getting the car started.” Dean whispered back.
“She hustled me!” Pete said, getting in John’s face but everyone here knew that John against Pete was no contest. John would beat him to a pulp before Pete could get a move-out.
“Just like you hustled other people, right?” John said, glaring at him.
“Hey, Pete, let’s just go.” Mike said, putting a hand on his friend’s shoulder. Apparently, Mike was the smarter of the bunch. Pete glared at John before looking at you.
“Watch your back, sweetheart.” Pete threatened. You didn’t worry about it because you wouldn’t be back in this town ever again, or at least, not for a while. Dean walked you out of the bar and when you, Dean, and John were safe in the car, you threw the money at John with tears in your eyes.
“I don’t ever want to do that again, John.” You said, feeling violated.
“Sammy, switch with me.” Dean said, getting out of the car. Sam got in the front without question and Dean got in the backseat with you. He pulled you into his arms and you placed your head on his chest.
“I’m sorry, Y/N.” John said with a sigh and he took off back to the motel to pack up.
“I feel so violated.” You whispered to Dean.
“I got you. You’re okay.” Dean whispered back, rubbing your back soothingly. He ran his fingers through your hair and suddenly, all that went away. Dean was with you and you were safe in his arms.
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