Confessions - Dean Winchester

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"Hey, wanna head to a bar?" asked Dean propping himself on the doorframe to Y/n's room.

Y/n looked up from a book he was reading, he got up from the bed and put it on a shelf. "Why what's up?" he leaned his back on the desk.

"I...gotta talk to you about something" Dean looked down for a second

"Alright be there in a moment"

Dean shot his head up, "Really?—" he cleared his throat "Alright". He walked away from the room, his heart pounding. How was he so nervous about this? He'd done it to so many people now but for some reason, Y/n scared—no, frightened him.

Since he had everything ready, or so he thought, he waited in his Baby. He tried calming himself but it only made him shake more, that's why he needed a few drinks before he went on with his plans.

He practically jumped out of the car if the roof wasn't there when Y/n knocked on the driver seat's window. Dean rubbed his head while Y/n snickered, opening the passenger seat's door.

"You alright bud?" Y/n asked grinning

Dean rubbed his head, nodding while mentally kicking himself.


They got to the bar around 8 and went inside, Y/n leading the way. They both ordered a drink and got a table somewhere in the corner.

Y/n sighed happily after a drink of his beer, "We never get time to do this these days anymore huh" he said smiling

Dean couldn't help but stare, which the other soon noticed after a few minutes of rambling about the past.

"Hey, are you listening?"

Dean snapped out of it, "Huh, what'd ya say?"

"Don't tell me you're already drunk Mr. Winchester, we just started" teased Y/n

" I assure you Mr. Singer, I can handle my liquor. Unlike someone I know" Dean teased back

"Wanna bet on that?" Y/n smirked

Dean forgetting something, the two had an alcohol drinking contest.

Well it seemed like that but through out the game the two kept bringing up stories from the past.

"Okay okay— Y/n rubbed his watery eyes from laughing — remember that time you had the yellow fever and a cat in a locker freaking scared you so bad you practically jumped on me and we both fell?!"

Dean laughed before taking a swig of his beer, "Then you got it and got scared of Sam opening the door that you pissed yourself"

A few hours passed by with the two just telling past stories and laughing their assess off.

Around 1, the owner of the bar walked up to them.

"Guys, we're closing soon. Can we call you a cab?" The guy said.

Dean snapped out from just staring at the half-asleep Y/n and looked at the owner.

"Nah. We're—we're good. Come on Y-Y/n, let's head back"

When Y/n didn't stand up, Dean put his arms over his shoulder and hoisted him up. "C'mon wake up, you're heavy as hell" Dean laughed

The owner looked at the two as Dean practically dragged Y/n out of the bar. He looked at his employee, "You think they'll be fine?"

The woman looked at her, "Probably not" then she shrugged.

The two watched Dean put Y/n in the passenger seat and then stumble to the driver's seat and got in.

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