Author's Note: This fic is dedicated to my big sis, Val, who requested Dean-angst. I hope you enjoy, sweetie! :)

What Hurts The Most

Dean sat in the corner of the motel room he, Sam, and John were staying at, cleaning out a rifle he held in his hands. For a 22-year-old he was a rather skilled hunter and felt as if he could handle just about anything. Quite possibly with the exception of his family breaking apart right before his eyes. He'd survived his mother's death, and felt very strongly that John was doing everything in his willpower to protect his sons.

Dean loved his father very much, couldn't imagine doing anything else but what John asked of him. Perhaps protecting Sam. Sammy. The kid was severely headstrong and stubborn for an 18-year-old. But he knew exactly what he wanted out of life. So Dean really shouldn't have been surprised when things finally came to blows between John and Sam that afternoon.

"Sam, what the hell is this!?" John demanded, waving around an envelope, which seemed to be pretty big and full of papers. Dean's eyes quickly met Sam's across the room. His younger brother sat buried behind his copy of Slaughterhouse Five for the millionth time. But Dean knew this time it was just a diversionary tactic. Delaying the inevitable. Dean felt his throat go raw and his heart rate speed up, and he wasn't even the one on trial here. He wasn't prepared for Sam to leave, wasn't sure how to deal with this. Not yet. Not ever.

"Sammy," he choked out in an inaudible whisper.

"It's my acceptance letter to Stanford," Sam replied, glancing up at John briefly before focusing on his book again.

"Why didn't you tell us you were applying to college?" John asked softly, yet sternly. Dean's head snapped up at being dragged into the argument. Oh, God. Sammy, no! He pleaded silently.

"Dean knew about it. But I didn't tell you because I knew you'd react this way."

"What do you mean, Sam?"

"You don't want me to go to college. You want me to stay here and be a good little soldier who follows your orders, just like Dean. But guess what, Dad? I'm not Dean. And I don't give a rat's ass what you think. I'm going to college," Sam growled, finally getting to his feet. He grabbed his suitcase, which he hadn't even bothered to unpack, and made his way to the door.

"Sam, if you go, you stay gone. You hear me!?" John bellowed, watching as Sam glared at him a final time before leaving, making sure to slam the door behind him.

Dean swallowed hard, quickly getting to his feet. He'd deal with his father later. He just couldn't let Sam leave like this. As much as he'd hate to admit it to Sam aloud, he needed his little brother. He climbed into the Impala and took off in the direction of the bus station. He soon found Sam walking along the side of the road. Seeing Dean, Sam walked faster. Letting out a snort, Dean rolled the passenger window down. Defiant tell the very end, huh? Well, good for you, smartass.

"Get in the car, Sam."

"No."

"Dammit, Sam, get in the car!"

Sam let out a sigh of annoyance, stopped and climbed into the Impala. He turned toward Dean, glaring intensely at him.

"Happy?" he snapped.

"Immensely," Dean grumbled. They drove in silence all the way to the bus station. Once there, Sam immediately clambered out of the Impala almost tripping over his feet. "Thanks," he grunted.

"Sam, I…"

"Don't, Dean. All right? We both know I need to do this. There is no way in hell I'm going back there to try to reason with him. He doesn't understand me. Why I need to do this. You could come with me," Sam suggested. Dean smiled half-heartedly.

"No, I can't, Sam," he said, rubbing at the back of his neck.

Sam sighed heavily and nodded his understanding. Dean watched as his brother boarded the bus and then headed to the car. Once he slid into the driver's seat he felt his hands begin to shake uncontrollably. He refused to cry. This was about something that made Sam happy. Sam needed this, needed to get away. And Dean wanted his younger brother to be happy. He really did. It didn't matter what he wanted at this point. That he felt as if the life he had known was crumbling down around him.

"Knock it off with this emo shit already, Winchester," he growled to himself. He started the car, leaving the bus station and thoughts of Sam behind him.

The next morning Dean lay in bed for several minutes, staring at the ceiling. Sam was gone. And Dean felt numb. Slowly getting to his feet, he headed to the shower. The warm water gently massaged his tense, knotted muscles that had formed the previous day due to stress in letting Sam leave. Taking a deep breath, Dean felt himself begin to shake like he had after saying goodbye to Sam. He lowered himself to the floor of the shower, not caring that water invaded his ears and nose. He just wanted the pain to go away. To leave, the way Sam had. Once the water had turned ice-cold he stood sluggishly, shutting off the shower. Stepping out of the tub, he grabbed a towel and dried himself off, a few minutes later leaving the bathroom, not even aware that he had gotten dressed.

He had no clue where his dad was, and frankly, he didn't give a shit at the moment. The bed he had vacated looked messy, warm and inviting. He ached to crawl beneath the covers and pray for a do-over. His brother couldn't have left. Abandoned him. Jesus. He was acting like a chick. He needed a drink.

Several hours later, after driving aimlessly, and stopping periodically to stare at the name Sam emblazoned on his cell phone, Dean found himself in a bar. Getting completely wasted. At one point during the evening, while feeling up a girl named Stephanie, he glanced toward the door and was shocked to see his father standing in the doorway. Enraged, John marched toward his eldest son, and roughly pulled Dean toward him. He flinched as he inhaled the stench of alcohol permeating from Dean's mouth.

"What the hell, Dean!? I've called you and called you. Why didn't you answer your phone!?"

"Because I thought it was Stanford demanding that we pick Sam up. That they've made a terrible mistake letting a, a Winchester into their snobby, stuck-up version of the Ritz," Dean hiccupped, before collapsing into a fit of giggles. John stared at Dean sadly. What Dean had said didn't make a lot of sense in some respects, but at the same time it did because he knew how close his boys were and that this separation must be killing Dean. Sighing heavily, he grabbed onto Dean's arm and took him outside. Once there, he helped Dean into the passenger seat of the Impala. Luckily the bar was only a few blocks from their motel so he could come back for his truck later. Reaching the motel, he helped his son into bed and watched as Dean fell into a drunken sleep.

Dean awoke to the sun shining brightly into the motel room. Groaning, he flung the covers over his head. He suddenly remembered why he avoided getting drunk. Drinking in moderation? Getting a nice buzz? Sure, good times. But hangovers were a bitch. A few minutes later he dragged himself out of bed and managed to get to the bathroom before he hurled on the carpet. Wrapping himself around the white porcelain of the toilet, he lost himself for several minutes as he brought everything back up from the night before. Once his vision wasn't so blurry and he didn't feel as nauseated he noticed a piece of paper on the bathroom counter. It was a note from his dad.

Once you've sobered up, meet me in Greensborough, Massachusetts. I've found us a job to do. Dean, you have to know that Sam leaving wasn't your fault. He loves you. He just really needs to be away from us for a while, to experience things on his own. Give him a little time and space. He'll get in touch when he's ready. -DAD

Leaning against the sink, Dean crumpled up the note in his fist as he finally let a sob rip through his gut and out his throat. The tears came fast and hard and he didn't even bother to stop them. After several minutes had passed and the tears had subsided, Dean palmed at his eyes and exited the bathroom. Grabbing his jacket and two duffel bags, one full of clothes, the other with weaponry, Dean went outside and climbed into the Impala. Turning up Rush's Freewill, he left the parking lot and soon found himself lost in the back roads of America. He smiled faintly to himself, realizing that it was more than time to move on. He had the right equipment, now all he had to do was find and kill as many evil sons of bitches as he possibly could.

THE END