Dean's past was pretty much the same until he was seventeen. They had finished up with a hunt and John let him drive home in the Impala, while Sam and him drove John's truck. John was trying to teach fourteen year old Sam to drive. After John took the wheel again, they started to head off toward town again, so they could go to the hotel and go to bed.
John was too busy talking to Dean on the phone to notice the Demon in the truck coming at them. Dean jumped out of the car after, calling 911 on the way. He wasn't crying yet. It seemed like an eternity before he got to the car. He checked on John. He wasn't breathing at all. He heard a gasp from the passengers seat and immediately ran around. Sam was bleeding badly, reaching out for Dean. He immediately pulled him into his arms, actually ripping off his own shirt to cover the large wound on his stomach.
"It'll be okay, Sammy. They're on their way.. You'll be okay." He found himself murmuring, looking down at Sam, brushing his free hand through Sam's hair, pulling it back out of his face. "They'll get you fixed up and everything will be fine. You'll be fine, Sammy."
Sam's breathing was labored and his gaze becoming unfocused as he stared up at him. He gasped out Dean's name, a bloody hand moving to the side of his face, leaving a smear of Sam's blood. His eyes started to shut a bit.
"Sammy, stay with me, please! Don't close your eyes. Stay with me!" He begged, tears falling from his eyes now, splashing down onto Sam's face. "Don't leave me, Sammy. I'm supposed to take care of you. Please, Sammy."
He could hear the ambulance coming as Sam's eyes opened again, focused on Dean's face. "D-don't l-leave me." Sam whimpered out.
Dean shook his head, keeping eye contact. "I'll never leave you, Sammy. You're my pain in the ass little brother.. I'm never going to leave." He said, his voice choking up.
"'s okay, D-dean." Sam said, his voice very weak, though he managed a smile on his face, even if it was very small. "'ll be okay, Jerk."
Dean returned the smile with a shaky one of his own. "You'd better be, Bitch.. You're all I have."
The ambulance was there now, paramedics rushing over just as Sam's eyes fluttered closed, his hand falling away. Dean let out a loud sob, staring down at him still. "Sammy, open your eyes. Please Sam.. I need you, please don't leave me."
The paramedics helped Dean pull Sam out of the car, putting him on the stretcher. They didn't even ask Dean to let him go. He was sobbing, curled up on the stretcher next to his little brother, still murmuring that everything would be okay. That he'd be fine. They put the both of them in the ambulance. He barely got a glimpse of them covering John with a sheet on the other stretching before loading it into the second ambulance before the doors were shut.
A few hours later, the doctors walked into the room they had put Dean in. Even though they had taken Sam away, he was still curled into a ball, covered in Sam's blood, while murmuring that everything was going to be fine.
Two of the doctors got him sat up on the bed, another one carefully shuffling with the papers in his hand. "Son.. We have some bad news." He said, his voice soft, compassionate.
Dean just stared at him, his face completely blank. "Where's my brother." His voice was barely a whisper.
"We did everything we could.. Both him and your father were killed." He said slowly. "We need to get some emergency contact information from you.. To get the next of kin to be able to take you in."
"I don't have a next of kin.." His voice lost every hint of emotion. "I don't have anyone else.. Only dad and Sam."
He wouldn't talk anymore, no matter what. They gave him a few pills to take, then left him alone. Dean slipped out of the hospital wan walked to the Impala, getting a few things before breaking into the hospital morgue, taking both John and Sam's bodies. He started driving, not stopping until he got to Bobby's.
He explained what had happened to him in a dead voice. Bobby helped him clean them both up, wrapping them tightly in white bed sheets They went up into the mountains close by, setting up two pyres. They started John's first, Dean insisting that he did it. He covered his fathers body with salt, then pouring half of the jug of fluid Bobby had given him. "I'm sorry, Daddy.. I tried to protect him.." He said, his voice still dead. "I'm sorry.." He lit the match throwing it onto the pyre. He watched it flare up, then watched as flames licked over his form.
He shakily turned toward Sam. He picked up the salt, walking close to him. This was his baby brother.. He looked peaceful, like he was just sleeping. If it weren't for how pale he was, Dean would've been able to convince himself he was. He slowly, carefully spread the salt over him, tears streaking his face again. "I promised you'd be fine.." He whispered, spreading the rest of the fluid over him. "I'm so sorry, Sammy.. I didn't mean to fail you." His hands were shaking too badly to light the match, so Bobby stepped, in, lighting it and holding it out to him, knowing Dean would want to do it.
He looked up at Bobby for a second before looking back at his baby brother. He had to force himself to throw the match down onto the thing. He collapsed down onto his knees as the flames rose, letting out a choked sob. Bobby sat down next to him, his hand on Dean's shoulder. He'd never tell anyone, and neither would Bobby, but he turned and started to sob on his shoulder.
He stayed with Bobby until his eighteenth birthday, helping him as much as he could and crying himself to sleep every night.