Dean revved the engine and pulled away from Bobby's house. He watched with guilt filled eyes as you stood with your arms wrapped around your middle. He tried taking a mental picture of you, of your Y/H/C hair flowing in the light breeze, how your Y/E/C eyes shined in the mid afternoon sunlight. Leaving you was one of the hardest decisions he'd ever made. Seeing the sadness and disappointment in your eyes made his heart clench in his chest. But he couldn't ignore the feelings bubbling within him, feelings that were completely foreign and shook him to the core.
This was the best thing to do to keep you safe. To keep you from falling for him and then having your heart crushed when he's pulled away from you. You already lost Carter, the pixie like girl who was more of a sister than a friend to you. You couldn't lose him too.
"It's for the best, Dean," Sam said. The youngest Winchester brother watched as his elder brother gripped the steering wheel tightly and tried to keep his emotions at bay. He felt for him. Dean had never had feelings for someone like he had for you. Ever since they were teenagers, Sam knew Dean had liked you as more than a friend. It was in the way he looked at you. The way he acted around you. The way he talked about you.
But as he got older and as you got older, that teen crush turned into something deeper. Something that Dean never thought he would feel for someone. The worst part about it was that he was never going to get the chance to act on it. That he'd never get the chance to call you his. It broke his heart to know he must have broken yours. It broke his heart to know he would never see you again. He had a little less than three months left and all he wanted to do was spend them with you. But he wouldn't die knowing he had led you on to his death. He wouldn't hurt you more than he already has.
Over the next couple months, it was a blur of the brothers drowning themselves in cases and looking for ways to save Dean from the inevitable. Dean would think of you everyday, his guilt for leaving and lying to you eating away at him. He ignored the text messages and phone calls from you. He talked to Bobby and would hang up when he began talking about you. Anything and everything reminded him of you. The waitress at the diner he ate at the night before, the floral scent when he took a shortcut through a park to get to the coffee shop across the way, even the damn flannel a stranger was wearing, the colors the same as your eyes.
He tried everything to try to forget you. He'd fuck anyone who threw themselves his way, he gotten rid of anything you'd ever gotten him. His heart was screaming at him, horribly craving the care you'd give him. But he still couldn't do it to you.
But eventually the phone calls and messages stopped. He knew you had given up. And with the help of the bar skanks and hard liquor, he had too.
And then he saw you. You were walking down the sidewalk in a small town in Tennessee. He knew you must have been there for the same reason he and Sam was, the vengeful spirit at a local hospital. He was in the impala, listening to a cassette and drumming his fingers on the wheel when he saw a Y/H/C haired woman turn the corner. His breath caught in his throat when the sudden emotions he spent so long trying to bury with girls and alcohol came bubbling to the surface. It was in the way you carried yourself, the slight sway in your hips and the way your shoulders were straight and confident that made him weak in the knees. If he were standing, he would have buckled to the ground. You hadn't seen him, having gone into a sandwich shop.
He was so tempted to run in after you. To grab you and crush you to him in a bone crushing hug. He debated with himself for almost ten minutes before you walked back out with a bag in your hand. You turned your back on him and walked back down the sidewalk. He watched with a torn head, follow after you or stay true to his promise to himself. But before he could act on either option, you turned down the street and disappeared around the corner.
Dean peeled away from his spot faster than you could say "dumbass."
Two weeks away from the day he was supposed to bite the dust. He was lounging in he and Sam's motel room when he heard your voice. He'd know your voice anywhere. And it sounded pissed. The sound of a door slamming got him up out of his position on the bed and walking over to the wall. He pressed his ear against it, trying desperately to hear what you were saying.
"You never stand up for me!" You yelled. He heard scuffling and then a groan.
"Yes I do!" Another voice said. It was a woman's, one Dean had never heard before.
"Then why didn't you tonight? You heard what he said to me, Daisy." Dean raised an eyebrow. Who said what to you?
"Yeah but you've got to admit, Y/N. He's right," Daisy said.
"Are you fucking kidding me?" You seethed. That was cold. Dean immediately hated this Daisy and he didn't even know her. "Get out."
"What?" Daisy asked.
"I said get out. I don't care where you go or what you do. Just get out," You said.
"Fine," Daisy said. The sound of the door opening and closing confirmed that you were alone. Dean listened as the creak of the old motel bed indicated you had laid upon it. The soft sound of your cries made his heart drop. Some bastard had hurt you. And your friend had taken his side.
Dean wanted so badly to go over there and comfort you. To shower you with affection and loving words. But he couldn't. He'd be gone in two weeks and that'd be cruel.
So when Sam returned from the diner with the impala and boxes containing burgers, Dean told him to pack up and they left. They drove for hours until they reached another motel. Dean's heart was so full of guilt, he drank until he passed out at the bar and had to have Sam pick him up and carry him out.
Five hours until Dean was due to pay the price for his deal. The hallucinations had started and he grew more anxious with each passing moment. They had Ruby's knife and Lilith's whereabouts, but he was still skeptical.
It was when he killed the demon possessing the cop that he knew they were headed toward one hell of a fight. If he already had demons on his tail, what would they be heading into?
When they found that Lilith was no longer in the fair haired little girl, Dean knew he was out of luck. Sam was frantic, begging with Ruby for any way to help him.
"I'm not going to let you go to hell, Dean!" Sam cried when Dean had pulled him away from the demon. His eyes were already filling with tears as he saw the serious expression on his older brother's face.
"Yes you are," Dean said.
"What am I supposed to do?" Sam asked. He felt defeated. He couldn't imagine life without Dean.
"Keep fighting," Dean said. "Take care of my wheels."
The clock chimed, indicating it was midnight. Both of the brothers turned to it in fear, knowing Dean would be dragged to hell at any given moment.
"Sorry, Dean," Ruby said. Dean looked over at the demon with a questioning expression. The two never had gotten along, but she seemed sincere. "I wouldn't wish this on my worst enemy."
The sudden howling and growls of hell's own bounty hunter filled Dean's ears. His eyes snapped over to the vicious hound, Ruby also spotting it. The three dashed into the nearest room with the hellhound hot on their tails. Dean covered the doors and windows with the dust.
It was when Ruby asked for the knife that Dean realized she wasn't... Ruby.
"Where's Ruby?" Sam asked. The brothers struggled against Lilith's hold.
"I sent her away," She had said. She had sauntered over to Sam, Dean watching and desperately trying to break free.
"So this is your big plan? Drag me to hell, kill Sam and become queen bitch?" Dean said.
"I don't have to answer to puppy chow," Lilith replied. She smirked and opened the door, the dust moving out of the way. "Sick him, boy."
Dean watched in horror as the hellhound sprinted into the room. He screamed as its claws dug into his flesh. Sam yelled for Lilith to stop, crying for his brother who was being ripped to shreds. With each bite and tear of Dean's flesh the hound made, Dean found it harder and harder to fight.
When Lilith smoked out of the blonde, Sam immediately went over to his brother. His leaf green eyes were wide and staring, not focused on anything just... there. Sam sobbed and held his brother close to him, saying his name over and over, wishing it were all a nightmare. But no, it was all very real. Dean was in hell, and Sam couldn't help but feel responsible.
So Sam held his brother, who's bloody and torn skin was already beginning to turn cool to the touch. He cried and screamed profanities into the air, angry at the world for taking his brother. His brother was dead. And he never felt so alone.
Dear Diary,
He's dead.