A Game of Pool

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Dean Winchester x Reader

Synopsis: You're a hunter who has heard of the famous Winchester brothers. What do you do one night they step into the same bar you're trying to hustle a game of pool in? You try to hustle Dean. But the prize might end up being more than money.


"Hey sweet cheeks, how about I buy you a drink?" The man next to you asked, standing close enough you were overwhelmed by the overpowering scent of his clingy cologne.

"No thanks. Not interested." You muttered, not even looking over at him.

You heard him mutter "Bitch" as he walked away, but you could care less. You were busy scoping the place out, waiting for the perfect group of guys to start playing pool so you could make some spending money.

Your job didn't pay the rent, not that you stayed anywhere long enough to put down roots. You were constantly traveling the road in your 55 Bel Air, looking for jobs. Not any type of job, but hunting monsters. Because that's all you knew. You had grown up with hunters for parents, and when they were killed off, it was just natural to keep following along in their footsteps.

One of the pool tables opened up, and you decided to make your way over there, your beer in your hand. Maybe if you started a game by yourself, someone would feel sorry for you, and try to join in. Then you could fleece them for a couple hundred, and be on your way, to the next town, and the next job. It was a lonely life, but you had gotten used to it.

Grabbing one of the pool sticks, you made sure your cleavage was low enough to attract attention, and biting your lip, you walked around the table, pretending to look nervous, and unsure. It worked, because before you knew it you had someone tapping you on your shoulder.

"Excuse me Ma'am, do you need someone to play with?" A deep voice asked from behind you, a hint of a double entendre to his voice. Knowing you had reeled in a sucker, you turned to face him, turning your facial expression into one that portrayed shyness, and nervousness.

Before you could reply, you glanced up at the man, and froze. He was tall, tall enough that you would get a kink in your neck from looking at him too long. His face was sculpted like those old Grecian statues your Mom had made you read about. There was a slight scuff to his face, like a five o'clock shadow. But it was his eyes that had you mesmerized. You had always been a sucker for green eyes, and these took the cake. They were a deep, almost candy apple green, with tiny flecks of gold mixed in, just enough to make the green really pop.

"Yeah, I was hoping someone would show me how to play." You stuttered, completely thrown out of wack by this gorgeous man in front of you.

"Well, I know a thing or two about pool. How about we play a game?" He asked, and you nodded. He went on to show you how to grab the right pool stick, and how to hold it. You almost shivered as his hand swept across yours. When he placed his hand on your hip, moving you so you were standing right, you tensed up, the touch sending a spark through your entire body.

"There. You know the basics. Ready to try a game?" He asked, and you nodded, watching as he bit his plump lower lip as he racked the balls. "Here, you go first." He told you, and you lined up your pole, your shot going to the right and barely hitting any of the balls that had been lined in a triangle.

"Oops." You muttered, and Dean chuckled at you, the sound heading straight to your stomach, creating butterflies. You had never been this attracted to a man from the get go, and you were hoping your stupid emotions wouldn't get in the way of bringing money home tonight.

The two of you played through the first game, Dean winning easily. He was talented, and you knew you were going to have your hands full if you wanted to win the second.

"There you go. That's how you play pool." He told you, taking a swig of his beer before he turned to put his pole away.

"Wait!" You said to him, and he turned, an eyebrow cocked. "Can we play one more?" You pleaded.

"Fine. One more." He answered, smiling back at you.

Running your hand up and down the pool stick, you caught his eyes shifting to it, and you knew you had him caught. "How about we make it interesting. I know you're going to fleece me anyways. But how about we put some money on the game."

His eyebrows narrowed then, and he stared at you quietly for a moment, before shaking whatever negative thought that was in his head away. "Sure thing sweetheart. How much?"

You didn't want to be too obvious. "How about fifty each?" You asked shyly.

He nodded. "Make it an even hundred and we have a deal."

You held your hand out, wanting to shake on the deal. He grasped your hand, and held it. You knew he felt the electricity from the touch, his eyes darkened to a forest green, and he licked his lip.

The game started much as the first one did. Dean let you go first, and you purposefully hit to the side. Dean of course sunk a couple of balls on his first shot. You then stepped up to the plate, sinking a couple yourself.

When you caught him staring at you, you shrugged. "Beginner's luck?" You guessed.

The last part of the game was neck and neck. You weren't sure if he was being easy on you, but you had to struggle to hold your own against him. It was coming down to the last shot, and it was your turn to try to sink the eight ball. Bending over, you felt eyes on your rear end as you lined up the shot. Taking a deep breath, you aimed, and hit, squealing when it went sliding into the hole.

"oh My God! I did it!" You squealed, jumping up and down, making your act seem more realistic.

"Yeah you did." He said, and he didn't even seem grumpy that he lost.

Throwing caution to the wind, you threw yourself into his arms, giving him a quick peck on the lips before pulling back. You raised your hand to your lips, the feeling of his warm, plump lips against yours was almost too much to handle.

Pulling his wallet out, he grabbed a hundred dollar bill and handed it to you. "You won that fair and square." He told you.

"Thank you." You answered, and he turned to walk away. Now wanting to part from him yet, you quickly wrote your number down on a napkin.

"Wait!" You yelled after him, and he stopped.

"I never did catch your name." You told him.

"It's Dean." He answered, winking at you.

You stood there in shock. "Dean? As in Dean Winchester?"

He seemed taken aback by the fact you knew his name. "How the hell do you know that?" He asked, coming back towards you so the two of you weren't yelling across the room.

"Because your daddy and my daddy hunted together a couple of times. My name is Y/N. Y/N Y/L/N."

"Y/N?" He repeated.

"Yep. And if you ever want to get together again. To play pool, or just to play, here's my number." You told him, pressing the paper into his palm before pressing a kiss against his cheek and walking out the door.

You kind of wished you had stayed behind, but you had a feeling you would be hearing from Dean, quickly. And you couldn't wait!

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