Takes place in the second half of season six, (a place I love) after Sam gets his soul back. Dean gets thoughtful, almost philosophical.
Dean looked over at his brother as he'd done innumerable times during the past four hundred miles.
Sam was deep in sleep, his breathing low and regular, his head abandoned bonelessly against the Impala's window, his ever more abundant mop of hair, although no longer worn in his once youthful bangs, acting as a pillow.
To Dean he still looked like little twelve-year old Sammy, and the big brother in him was conscious of the fact that it would always be so, even if they ended up as ever-bickering eighty-year olds that passed their time sitting in a park reminiscing about days gone by.
"Friggin' unlikely," Dean reminded himself curtly.
He loved to be behind the wheel of his Baby; relishing the freedom to go anywhere, do anything, be anyone; but he had the absolute certainty that such pleasures without his brother by his side, would be null and void.
He knew because he'd already experienced it first-hand.
The year with Lisa, though for the most she'd been understanding and patient, had been a year of torture, and he hadn't even been physically capable of bringing himself to drive the Impala without Sam.
His emotions engulfed him as he remembered how he'd felt when he'd first glimpsed his brother sitting in front of him in the Campbell's hide-out.
He'd been re-born in that split-second; a new Dean Winchester rising from the ashes of the old; a phoenix; the first breaths of his new existence coming strong and even at the mere sight of Sam, and like a child just learning to walk he'd slowly made his way towards him, alleviating the suffering of the past year with the embrace of his brother's living breathing body. Sam's body. He hadn't known then the literal truth of those words, but even soulless, it was Sam!
His mouth twisted up ironically; their upbringing had moulded them into such a state of co-dependence that the mere sight and nearness of the other gave them the strength and will to live on and fight.
In the warehouse, Gabriel had blathered about Destiny, and Cain and Abel, If Cain had loved Abel the way he loved Sam, the sin of fratricide would have had to wait for someone else to invent it.
Much as he loved his Baby, he loved Sam more. He could envisage a life without her, but not without Sam, never without Sammy.
He knew that now. They had been through so much together, made so many mistakes, distrusted and hurt one another, but he oft-times wondered if everything that had happened had been designed to bring them to this point; to the absolute trust they had now in each other.
He had gotten his little's brother's soul back from the Cage against the advice of many.
The one whose opinion had surprised the most however was Castiel's.
How could the angel even consider advising him to leave Sam's soul in eternal agony when there was even a minimum chance of getting him out? Even if his brother came back too broken to do more than lie in a psych ward, anything was better than suffering in Hell. He shook his head in confusion at the angel's attitude.
Ironic, he thought that the one to save Sam was Death, the most improbable of all the supernatural douche-bags to ask for help, and yet he had been the most understanding; though he still scared the shit out of him.
Sammy had clowns, Dean had Death!
Well, now they could all piss off.
He had Sam back, albeit with a shaky wall holding in his Cage memories, but Dean knew that his brother was strong, and they would battle their way through whatever happened.
He'd been Hell's unwilling guest himself and though he'd learned to push down the memories, he knew they were still there, ready to pounce on him like some rabid dog eager to rip him asunder.
"Hey," a drowsy voice broke into his thoughts, "Can't a guy get to sleep in peace around here, Jerk?"
"Whaaat! I didn't say a word, Bitch," Dean retorted surprised "I haven't opened my mouth, not even to sing, since you and your princely ass fell asleep hundreds of miles ago!"
"You were thinking too loud, man," Sam continued sluggishly. "I could hear you from here."
"Well, this tops it all. You starting to read my mind now, Sasquatch?" Dean asked disgruntled.
"Heaven forbid. I'd have to run off and hide at some of the stuff I'd see in there," Sam mouthed disgustedly. "Naa, I've been awake for the last few minutes and the expression on your face was your "Dean Winchester is deep in philosophical thought" look."
"Well Sam you learn something new every day. This I had yet to hear coming from your geeky lips. 'Philosophical thought' indeed! You are so way out man!" Dean replied smirking. "I was thinking of Mindy and Cindy the two hot chicks I had a fling with the other night, and wow did they know how to swing it, back and forth up and… "
"Dean, shut up! I'm well aware of your "I'm thinking about hot chicks face" and that wasn't it," Sam interrupted sleepily as his eyes started to close again, thanks to the lulling hum of the Impala. "There's nothing I don't know about you Dean, so you're just gonna have to live with it," he finished off pompously before sleep overtook him.
Dean waited until his brother was well under again before exhibiting a full on smile. " Philosophical thought." Right!
His philosophy was simple; he and Sammy together against all the crap that existence threw at them! No more, no less.