Series Rewrite- Background Stories

John Teaches You To Hustle

Author's Note: In this, the reader and Dean are 17 years old and Sam is 13.

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"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 grabbed 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 you at John for help.

"First, the guys at the bar will most likely will 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 their 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 has 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.