Dean lived a pretty quiet life in a small house in Kansas, along with his brother Sam. He never told anyone about his actual job, not even his brother. Casually bringing up that he was an assassin wasn't exactly his idea of getting the neighbors to like him. Whenever the topic of careers did come up, he just lied and told them he's a freelance writer who's working on a novel about gardening, which he knew nothing about.
As much as Sam wanted to question it, he kept quiet and didn't talk back when checks up to thousands of dollars came rolling in the mail. But the day a check for $100,000 came in the mail was when Sam just had to bring it up.
"Dean, why did we get 100 grand in the mail?" Sam asked as he barged into Dean's room, noticing his brother packing clothes into a duffel bag.
Dean just shrugged, "I don't know. Maybe some rich people decided to be generous all the sudden."
"Dean, even you know that's a damn lie. What's really going on? And where are you going now?" Sam persisted.
Dean stopped from shoving clothes in the bag and looked his brother in the eye, "You wouldn't understand. Trust me, I'll explain this when it's all over."
"When what's all over?" Sam asked, his voice starting to raise in annoyance. Dean zipped up his bag and stood up, approaching Sam.
"Excuse me," Dean eyed Sam, hoping he'd let him pass.
"No. Tell me what's going on and I'll let you go," Sam said, crossing his arms.
"Sammy, I'm going to be late. Move please," Dean pleaded.
Sam sighed and moved aside, letting him through. "You better explain everything when you get back. I'm tired of lying to our neighbors all the time."
"I will Sammy. I promise," Dean said with a nod before he walked out.
~Time Skip~
What Dean didn't till Sam was that he was off on another job, this time to kill a politician. The prize was 80 grand. A little less than his last job, but still decent. Dean was known for picking the difficult jobs. It gave him a sense of thrill and adrenaline. Yes, it was risky, but the pay was amazing.
He did his usual routine, rigging the security cams, getting a copy of the target's room key and so on. As he approached the hotel door, a 'Do Not Disturb' sign was posted on the door. "Weird," Dean muttered, knowing that the guy wasn't supposed to be in his room till 9.
As he opened the door slowly, dressed in his bellhop costume, he was startled by the sight. His target laid limp on his bed with an open bottle of pills in one hand. His shirt was slightly unbuttoned and his tie had been untied.
Dean quickly put on his gloves and walked over to check the man's pulse. He placed his two fingers at the corner where his jaw and neck met and felt no pulse. This guy was already long gone.
"It's you again. Long time no see," a familiar female voice spoke from behind him. Dean sharply turned around, spotting the same woman he had seen from when he killed that senate.
"(Y/N), right?" He asked with a smirk, glancing you up and down. You wore a tight black dress and your hair was a tousled mess.
"How'd you do it?" Dean asked, taking off his gloves.
You pointed to the two glasses of wine that rested on the night stand beside the bed. "Karma's a bitch," you grinned deviously.
"Sure it's karma?" He raised a brow, "Cause I'm starting to think it's fate."
"You should go before I add you to my hit list," you warned as you approached him, just inches apart.
"What makes you think I don't want to be kissed by death?" Dean smiled as he leaned even closer, almost whispering. You bit your lips nervously, glancing up at his green eyes which surprisingly weren't looking into your eyes but instead gazing at your lips.
"Any last words?" You whispered against his hot breath.
"Kiss me," he ordered and wrapped your arms around his neck, pressing your lips softly into his.
He slowly brought his hands to the edges of your waist, grazing them up and down, which caused you to quiver under his hold.
Suddenly, an alarm rang loudly, coming from your phone, which caused you to abruptly pull away from the intense kiss. You quickly looked down at your clock and sighed in anger, "Crap, I was supposed to already have the evidence cleaned up by now."
"You set alarms for yourself?" Dean asked, chuckling slightly as he asked.
"Yes. Two hours for set up and preparation. Thirty or less for the kill, depending on the technique I choose. Then an hour for clean up," you quickly explained, turning to walk away until he grabbed you by the wrist.
Dean took the phone from you and set an alarm for an hour later. "What'd you that for?" You furrowed your eyebrows.
"What do you think?" He winked.
You titled your head then suddenly it ticked. "Ew no. There's a dead guy in here. You're hot but I'm not that desperate," you cringed, "Just help me clean up and I'll give you one-fourth of my earnings."