One week after Sam's swan dive into the Pit, Dean woke up with a start. He didn't remember last night. Or the night before. Or the one before that. He'd drunk himself halfway to oblivion since six hours after the jump, and he had to congratulate himself on waiting that long. The sound of crunching glass brought him into the present – waking up in an alley behind a no-name liquor store in Texas, and the store clerk tossing bags full of empty bottles into the Dumpster a few feet away. Dean wiped his eyes to clear some of the fuzziness, and decided it was not the time to face the world sober just yet. He didn't realize until he got to the register with the bottle of Jack that he'd burned through all his cash, and for some reason or other (he really couldn't remember) all his scammed credit cards were gone. Dean left the whiskey on the counter and walked back outside… But only five yards from the door his pride gave way to his desperation and his hangover. "Hey, you got any change?" he asked the first guy to walk by.
"Get a job, shitbag."
Dean opened his mouth, and closed it, and hung his head in disgust.
He'd beaten the Devil at his own game, he'd faced his crazy with a smile on his face… But Sam couldn't tell Amelia the truth. It was getting harder to cover up; he always did talk in is sleep, and he still had their pictures tucked away in a box on the top shelf of the closet he shared with Amelia. It wasn't that Sam didn't love Amelia, didn't love every minute of the life they'd built together, didn't feel terrible keeping secrets like this from her, but talking about Jess was still too painful even after all these years (or maybe because of them). "Sam, what's this?" Amelia entered the dining room, holding a shirt that clearly didn't belong to either of them – a girl's tee shirt, with the neck and half the midriff cut off, with a pair of Smurfs on it. Jess's favorite pajama shirt.
"Uhm… I don't know. Maybe Chrissy next door snuck her laundry in ours again?" Sam held his breath until Amelia gave a thoughtful nod and left, apparently satisfied with the answer. Someday, he was going to be in so much trouble.
In retrospect, this was probably a stupid idea. If all you do is make a ton of noise while flashing a little knife around, everyone is just going to start scrambling for a bigger weapon. But hindsight is always 20/20, and only now did Cas realize that a quiet, kind rebellion of understanding would have made free will in Heaven more permanent and less deadly. It was entirely possible that he would have been killed before it could be completed, but in the past few years he'd learned that ideas are harder to kill than angels. Maybe it would have been better that way – Cas looked down at the souls of forsaken monsters that were pushing against his vessel, the souls that were supposed to be his ultimate weapon, and thinks that maybe the things he tried to see through to the end were the things that went wrong the most. But then he heard Sam praying to him, offering to help, and he thought maybe he didn't have to mess this up anymore, maybe he had a way out…
In retrospect, he should have known better.