Three cars came barreling down the gravel road, rapidly approaching the gates that separated Camp Chitaqua from the dangerous ruins of what used to be America before the virus hit.
As the cars came to a stop the driver side door of the truck nearest the gate swung open and a certain bowlegged man stepped out, slamming the door irritably behind him. Complaints could be heard coming from somewhere behind the man. "Watch it! You idgits tryin' to kill me?" Bobby Singer yelled as the men who were lowering his wheelchair-with him in it- from the back of the truck, nearly dumping him from the chair in the process. The gravel crunched as the wheelchair met and its owner angrily wheeled themselves away, running over toes as they did so. "Dean! Wait up!" Bobby called after the man in the old leather coat. As the older man approached, Dean made a point not to make eye contact with him, it was too difficult to even look at him right now, knowing what he must do.
The supply run they had gone on had not run as smoothly as they had hoped. Croatoans had surprised them as they were stuffing various items into sacks. Bobby was still a good fighter despite his disability, but in the end he was outnumbered. Fortunately, Dean had heard his distress and came to his aid, but not before one of the rabid monsters had sunk its rotting teeth into the arm of the old drunk. Bobby had kept insisting the bite hadn't pierced through his coat, but Dean knew the signs. There was nothing he could do about it either, other than put a bullet through the skull of the one man who ever treated Dean as anything other than a hunter.
Tears streamed down his freckled cheeks as he stood behind Bobby, waiting for the gate to be opened. He sucked in a deep breath as he placed the gun against the back of the wheelchair, aiming it straight for his heart, so at least he'd go quickly. He made eye contact with Chuck through the gate, who nodded sadly, instantly understanding. Of course he knew; he had probably seen it already.
Just as the gate began to open and the men began to shift on their feet in anticipation, Dean pulled the trigger. Bobby instantly slumped over, nearly falling from his chair. Overcome with emotion, Dean wiped his cheeks and made his way to his cabin without a word to anyone, not even Cas, who tried desperately to get Dean to stop for a moment. But Dean just slammed the door in the face of the only person he had left, and collapsed into his bed, letting the tears fall freely.
Later that night, Dean reemerged from his cabin with an old duffel bag from his hunting days. He headed silently over to the small cabin where he knew Cas was sleeping since he had kicked him out of their cabin. "Uh," Dean began quietly, "Bobby always insisted on a hunter's funeral." He shook out, indicating the duffel. Cas just simply nodded his head. Together they walked to where Bobby's body was still slumped over in the chair, mostly because no one dared to touch it, knowing how Dean would react. The fallen Angel helped the broken hunter prepare the funeral and watched silently as Dean pressed the match to a piece of wood, the flames licking up the sides of the wood as soon as it caught fire. Without a word, he walked back to Castiel's side, who grabbed his hand in one of his own and wrapped the other around his waist in an attempt to console him. Dean, who usually pushed away any kind of affection since Sam left, made no move to escape Cas' gestures. They stood there together, watching the fire die down until there was nothing but a few embers glowing.
A lot changed after that night. Dean became detached and cold towards everyone and showed no emotions other than anger and pure determination. He eventually ended up pushing Castiel away too, who moved to a different cabin and began experimenting with certain drugs and even holding orgies for the residents of the camp. Dean held no place in his heart for love anymore, and when Past Him showed up two years later he was already too far gone to even be saved by himself. He sacrificed his friends –and shortly after, himself- for revenge he never got.