Set sometime after John Winchester's death (early Season 2). Canon extension.
"Are we gonna have this conversation, or are we gonna continue to pretend like nothing's wrong?" Sam asked angrily, slamming shut the door of the motel. It was late night and they were entering their motel room after a long hunt.
"Sam... I," Dean shook his head, exasperated, rubbing his forehead with his palm "Look, what do you want me to say here, man?"he shrugged, "Dad's gone, he's not coming back, and that sucks... but I'm dealing with it, man, and all we can do now is keep at it, let's keep killing these evil sons of bitches, alright?"
He looked at Sam, pleading almost. Sam kept his eyes to the floor, trying not to tear up. He let out a sigh and shook his head.
"Dean, this is Dad we're talking about. How can you just... move on from something like that?" Sam knew Dean, and it was clear he was trying to bury everything so deep, and it was exasperating to see his brother go through the motions of pretending things were fine when clearly everything was spiralling out of control. Why wouldn't Dean just talk to him for once!
"Okay..., Sammy" Dean's voice tender and tired now. He held Sam's shoulder "Tell me, what do you want to do?"
After a pause, Dean smiled slightly "Hey, we can try couples yoga, maybe draw a feelings circle and sit around, sharing and caring? And then, we can do the whole six stages of grief thing- or wait, is it seven?" He let out a short laugh "Is that what you wanna do Sammy?"
"Shut up, Dean!" Sam retorted, a small annoyed smile on his face, slapping Dean's hand away. Dean relaxed, seeing that Sam was cheering up a bit. "You know that's not what I meant". Sam saw that this conversation was going nowhere, and he saw how tired Dean looked, so he decided to drop it. "Alright Dean, let's just go to bed. Got to start early tomorrow. Bobby said he has a case for us."
"Aww, just when I thought we could braid our hair and paint each other's nails" smirked Dean.
"Jerk" Sam shook his head, smiling.
"Bitch" Dean promptly retorted ruffling up Sam's hair in the process.
"Go away!" Sam smacked Dean's hand in mock annoyance and turned off the light, slumping into his bed.
Dean turned away and let out a sigh. He felt around for the quarter whisky bottle he'd left on his night stand and took a long swig of it, and enjoyed the sensation as the neat whisky burned down his throat and chest. Another long swig and Dean began to feel a slight buzz. He let out another short satisfied sigh as he rested his head on his pillow.
He looked over at Sam, now asleep.
"Watch out for Sam, Dean!" John's last words to Dean reverberated in his head.
"Dean, you got to watch out for Sammy... you got to save him Dean" the words pounded in Dean's head.
"Save him? What do you mean Dad?" he had asked.
"Just listen, Dean! You got to save Sam... and if you can't, Dean... if you can't save Sam... you're gonna have to kill him, Dean. If it comes to that, you GOT... to kill Sam. Promise me".
Dean had no words, as he looked at his Dad, scared. He had just woken up from almost dying and now Dad was saying he might have to kill Sam? What was happening? He remembered his dad's forced smile through teary eyes. He hated himself that he wasn't able to say anything, completely tongue tied, everything in his head swirling. He should've understood then what Dad was planning to do, how could he be so stupid?! Why didn't he follow Dad? Why didn't he say anything? How could he let Dad die like that?!
Dean realised his eyes were tearing up. He cupped his eyes with the palms of his hands and bit down hard on his lower lip to stop himself for crying.
Truth is, he was terrified, and riddled with guilt about his Dad's death. In his gut, he knew Dad had done something... something bad to bring Dean back from the dead, and that something had cost Dad his life! AND the Colt! The only shot at killing yellow eyes! What was Dad thinking?! How could he do that! Dean was so disgusted with himself. He couldn't shake off the feeling that he shouldn't be here, and that if his Dad hadn't died trying to save him, he would be alive, Dad and Sam would have the Colt, and maybe even killed that yellow eyed son of a bitch by now!
A tiny sob escaped Dean's mouth. He quickly turned to look at Sam, and was relieved to see that he was asleep and hadn't heard him. Dean breathed slow, fist over his lips, trying to steady himself. He reached out again towards the whisky next to his bedside and brought it to his lips. Empty! Dammit.
This is Dad he's talking about, Dean tried to steady himself. Dad would've thought his decision through. There must be a reason he'd do something like this. Maybe it had to be Dean? He felt a pit in his stomach. He feared he wasn't strong enough to do what his Dad had planned for him, for what Dad had sacrificed himself for! They had no leads on the Colt or yellow eyes. Dean was trying to look out for Sam, continue hunting and keep on fighting, but it was getting harder and harder. John's words kept ringing in his brain. He couldn't fall asleep unless hammered anymore, and Sam was having more frequent freako visions and Dean was having a harder and harder time pretending like it was all okay, and like he knew what to do. He understood why Sammy kept asking to talk about Dad, Sam was hurting, he wasnt able to bring himself to talk to Sam about any of it, and Sam could probably tell that Dean wasn't keeping it together very well. But what could Dean tell him? That Dad was gone, it was probably his fault, and the last thing Dad had said was that he might have to kill Sam!? Dad would've known what to do. He'd be strong enough to handle something like this! The pit in Dean's stomach was knotting itself up.
Dean jerked himself up from bed. He wished the pounding voices in his brained would just shut up for a minute.
He glanced at Sam again, Sam was okay. He was okay, and they'd go hunting tomorrow together. He hung his head down and shook his head slightly, a small smile on his face. Quit sitting around and feeling sorry for yourself, you fool!
He got up and quietly closed the door of the motel room in search for more booze.