Day 1, Dec. 28: You are the cute server from the bar, and I keep on drinking so you could refill my glass?
Pairing: Dean x Reader
You glanced over at the green eyed man who sat at the end of bar. He had been there for just under two hours, and had had a constant stream of alcohol, but he didn’t seem to have gotten drunk yet. Maybe a little tipsy, but you could tell that he was no stranger to nights like these. He was cute too, hell he was damn sexy if you were going to be honest. He had a slight stubble, and while you normally preferred more clean shaven man, you kinda digged it.
You turned your eyes away from the handsome stranger to watch a man walk out with a girl on his arm. It was getting closer and closer to closing time, and more and more people were beginning to leave the bar. You walked over to the jukebox and flipped through it, as you liked to DJ the music if nobody else had anything they wanted to listen to.You found the song you wanted and put it on, unaware that the man at the end of the bar was watching you.
You were good looking, there was no denying that, and while Dean hadn’t come to hook up with a random girl tonight he still found himself watching you as you moved around the place. You came back behind the counter and cleaned a glass, immersing yourself in the song. It was cute. Dean almost thought about not saying anything, and just watching you, but he just couldn’t keep his mouth shut.”Semisonic?” He asked.
You looked over at the man in the corner with a half smile on your face. “Is there a problem with that?” You asked, making your way over to him with the drink he had been having for the last hour in your hand.
To be honest Dean didn’t mind the song, it was good for a 90s alternative rock song, but the fact that you were listening to 90s music meant that you were a bit too young for him. Or so he assumed. You noticed Dean looking at his empty glass, and you held up the bottle of alcohol.”You want another?”
“Would you?” Dean held the glass out to you, and poured some more into the glass. You were used to men, having worked at various bars since you had gotten out of college, and you tended to know what they were thinking a lot of the time because of that, and you knew what this man in front of you was thinking.
”I’m 31, by the way.” Dean lifted his eyebrows as your comment, but you were already walking away. His eyes followed you, or rather your butt, as you told an old man that he had had enough. It was obvious that he was a regular, but once he left it was just the two of you in the bar. Dean finished his glass, and the clink of the empty cup on the bar had you walking over once more.
“So is this supposed to be a sign then? You want me to leave?” Dean asked, a slight smirk forming on his gorgeous lips.
You smiled and looked at the clock,”I’m not kicking you out just yet,” you informed him.
“Good then can I have another?” You obliged, before putting the bottle away, letting the man know that it was the last drink he could have.”Do I have to leave after I finished this?”
You looked over at Dean and bit your lip. You had vowed to yourself that you would never hook up with a guy who came to the bar, nor would you grow feelings for a guy who came to your bar. But damn, even the hot boys weren’t this hot, and this man didn’t seem to be an alcoholic, at least not in the common sense like most of the men who came here. You found yourself answering his question before thinking,”No, you can stay longer if you’d like.”
You felt your cheeks heat up, and the man chuckled,”Your cute, you know?” Yo let out a dry laugh, and busied yourself with organizing all the bottles and glasses.”You seem hesitant.”
This man had you pegged, just like you had him pegged. You could tell that he liked you, for more than sex, and you guys hadn’t said more than a few sentences to each other. You could tell that he had a hard life, maybe he had been in the army, but he didn’t seem the type, He had killed before, you could see it in his eyes. He was also caring though. He wasn’t a bad man.
Dean could tell that you wanted to talk to him, but you were slightly afraid, it was clear you had the hots for him. You were a good girl, not the usual slutty bartender stereotype, and Dean liked that. He felt himself wanting to get to know you. “Why are you nervous?”
You turned around with a smile on your face,”Okay, Sherlock. You’ve got me,” and you were a geek too,perfect,”I don’t normally like to talk to…to guys who I find attractive that have spent the whole night drinking beer at the bar. It’s a small town, usually anyone who comes here is an alcoholic, but it doesn’t seem that it’s that way with you.”
Dean smiled and nodded, finishing his drink, “I understand. Wanna get me another?” You laughed and Dean smiled. “Listen, umm, I have a brother, he’s probably texted me a hundred times already, but I turned my phone off. It was nice talking to you though.”
You frowned but nodded, you felt slightly let down, you thought- it was silly- but you thought maybe you might have something with him. It was really stupid though, wasn’t it? Even so you found yourself asking if he wanted to meet again sometime.
“Sorry sweetheart, I’m leaving first thing tomorrow, I’m here on a, um, a business trip.” The man seemed sorry too, really and truly.”It’s Dean, by the way.”
“(y/n),” You gave a small smile and a wave which the man, Dean returned, before heading out. At least you knew his name. You went back to doing your closing up routine, singing along to the song, as it was on repeat.”Closing time, every new beginning comes from some other beginning’s end.”
You looked out the window, and noticed the lights of the car that must belong to Dean were still in the window. He hadn’t left yet. You bit your lip, before taking off your apron and making your hasty way out the door. Maybe you could still catch him.
And you did. Dean was making his way back to the bar, and you met in the middle, your lips touching together, Dean’s fingers going up to your hair, your hands wrapping around his neck. “Maybe I could stay a little longer.”
I know who I want to take me home.I know who I want to take me home.I know who I want to take me home. Take me home.
“Jack was ex-military. The Air Force to be exact. Tall and stocky with a full bushy beard and glasses, he didn’t look at all like a criminal. He cleaned up nicely when he wasn’t with the crew; often wearing a nice dress shirt and tie, along with an expensive watch. But when he was with the Fake AH Crew, he resorted to a much more casual hawaiian shirt and shorts. The others always gave him hell for it, but none of them could deny that what he lacked in fashion sense, he made up for in criminal skill. He was the pro pilot and getaway driver, a man able to expertly lead a double life with his outwardly sweet-looking nature. His pretty Australian wife had no clue on what he was up to during his business trips. The man tried to keep it that way, because he swore that if she did, she’d leave him for sure…”
once when i was 7 i ate some cereal and instead of drinking the leftover milk i dumped it out and my dad saw and he had me go to my room and get $5 and he burned it in the sink to teach me a lesson about being wasteful and that’s everything you need to know about my dad