These requests are originally from my Tumblr (@carryonourwaywardoneshots). If you prefer to read one shots on Tumblr, you can go ahead and check it out :) As it says in the title, requests are accepted and loved. I will try to do them as much as I c...
I'm so sorry for posting this REAALLLYYYY late, so here it is. Don't forget to vote if you like it, I really appreciate it. Ghost readers are the worst.
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Ever since she began hunting with the Winchesters, she was going out to random bars with the oldest, Dean. Dean didn't mind having a drinking buddy for a change and (Y/N) didn't mind that Dean flirted with anything that walks when he was drunk. Of course, they had no attraction to each other whatsoever, it was still hilarious to hear the pickup lines Dean could come up with when he was completely hammered.
One time, around November, the two were at a bar connected to the motel together. For being a small bar, this thing was almost filled up to the brim with travelers, lonely men, and just people looking for a drink. It was loud but not the loudest bar that the pair had been to. Dean and (Y/N) were seated at the counter on stools, challenging each other to whiskey shots that Dean didn't think (Y/N) could handle. "I'm going to make a bet right now," (Y/N) began, picking up her first shot and holding it near her mouth, "If I can get all five of these done before you, you have to let me drive 'Baby' to the next hunt when we're done with this one."
Dean smirked, thinking she wouldn't be able to. Every time they went to the bar, (Y/N) usual ordered "chick drinks", as he put it. There was no way she would be able to handle whiskey shots, let alone five straight. With a chuckle, Dean picked up one of his shot glasses and mirrored it to (Y/N)'s. "Deal." Was the last word before they downed their glasses, (Y/N) slamming hers down first and reaching for the second one. Not even a second later, Dean slammed down his and grabbed his second. Of course, (Y/N) shot that one faster than the first, ignoring the burning feeling traveling down her first.
As she moved onto her third and then fourth, Dean stared at her as he moved on to his third, definitely slower than her. Picking up her last and final shot, she downed it and slammed it on the table, meeting her eyes with Dean's who just finished his fourth. "God d-," Dean hickuped and covered his mouth, "God damn, woman. You hustled me!"
(Y/N) smirked, taking pride in her work. "The only reason I've been getting 'chick drinks' was so I could finally trick your ass." Her words were slurred, leaning on the counter for support. Rolling his eyes, he took his final shot and laughed, "Well you did and it won't happen again, I promise you that." (Y/N) smiled, before placing her hand on Dean's shoulder, "Okay, Winchester. I think we've had enough, let's head back to the motel before we get completely hammered." Just as she twirled around in her seat, a tall, handsome man walked up behind her, a sweet smile on his face. "Hey there." She raised her eyebrows, trying to make it seem like she wasn't as drunk as she really was.
"Hey, I saw you across the bar take those whiskey shots like water. That was... incredible." He sat next to her in the stool, looking to Dean and smiling at him. "I'm Troy, by the way." He held his hand out to the both of them and they shook it one by one. "I'm (Y/N) and this is my friend, Dean." He brushed aside his dark hair revealing a set of deep brown eyes, ones you could get lost in if you looked for too long. "Nice to meet you, (Y/N)." He gave a little side smile before he began again, "Mind if I buy you a drink?" As nice as it sounded, (Y/N) shook her head and turned towards Dean. "I think I've had enough to drink for a while." She chuckled, Dean smirking once he realized this guy was trying to pick her up.
