Dean x Reader One Shots

Dead Eye (Angst) (Imagine being an assassin sent to kill Dean)

Summary: Imagine Dean finding out that you're an assassin sent to kill him.

Word Count: 3,234

Your time was running out; you'd asked for two extension weeks and the last of those two was about over and you only had a single kill to show for it. The younger one was easy, he was nothing more than a distance shot-and-hop after the two brothers got into a fight, and you were doing well to distract the older one while his stubbornness did most of the work for you. It was convenient, the fact that the Winchesters got into a fight on the exact day you took out Sam and you knew that if that hadn't happened, you likely would have been found out by now.

But after a full two weeks of fighting, you knew Dean was likely about to give in and call his brother. It was so like him–you already knew after the two weeks of mixed sleeping and playing therapist for the man–to be unwilling to swallow his pride and call his brother when he needed him.

Not that it was even a pride issue, but regardless. You had Dean Winchester damn near figured out because he wasn't much different from any of your other targets.

But what did set him apart from your other targets was the fact that he was standing in front of you right now, a gun pointed at you with his flexed arms just behind it, a scowl on his face and dead eyes staring right back at you.

"So what, then?" His face was entirely still aside from his moving lips, his eyes dead while they stared on at you through the dimly lit room. "That was your whole game?"

You rolled your eyes, cleared your throat, and crossed your legs in the chair before setting you arms on the arm wrests and pointing a lazy finger at the man. "Stop being melodramatic, it's nothing personal."

"Oh, it's not personal?" Dean slightly narrowed his eyes while he said that. "Wanting to kill me isn't personal? In what fucked up, mathematical universe does that equation add up?"

"Why don't you put the gun down, Dean, we can talk about this."

"You certainly weren't game to talk about this when you were slipping rat poison into my coffee."

"It was Xanax, now you just sound paranoid."

A look of confusion passed Dean's face and disappeared so quickly that you almost missed it, but finally he asked, "Anxiety medication?"

In all honesty you'd been hoping for him to drink the coffee laced with Xanax and then carry on his usual alcohol routine; the combination would make his heart rate and respiration drop just enough for him to likely lose consciousness, which was when you'd swoop in and put him in his car, which would happen to drive off a bridge. Easy enough, simple enough, and given that most medical examiners were lazy when it came to things like that, it likely would have been ruled a suicide. Clean, effective, not the first time you'd done it.

"Maybe if you were a pharmacist you wouldn't be in this situation."

"You're really joking around right now?" Dean took a step closer to you, closing the gap between the two of you until it was only five feet; he was tall, seemingly even more so now that he was standing while you sat on the chair and looked up at him, but your heart rate was steady, your breathing relaxed. "I've got a gun on you and you're mocking me?"

"You act like this is the first time I've had a gun on me."

"So are you entirely heartless or is this just an act?"

"Depends," you shifted your weight to allow yourself to cross your legs the opposite way, all the while keeping your eyes on Dean's. "Which one is more likely to work?"