How It Should've Happened

It's All About Context

Dean was sick of reading the same things about Pestilence over and over. "Sickness", "destruction", "chaos", "apocalypse". He knew all of that already, what he needed was how to find him. He looked to Sam who was mid summoning spell. "He's going to be pissed you summoned him." Dean mumbled. 

"Yeah well we don't exactly have his cell number." Sam countered. 

"Hello boys." They heard and Dean didn't even look up from his book. 

"Crowley." Sam looked squarely at the demon. 

"Moose! So nice to see you. Love what you're doing with your hair." This time, Dean beat Sam to the eye roll. 

"We're looking for Pestilence Crowley, skip the small talk. Any leads?" Dean said twirling his demon knife absently. 

"I have a thought, but your timing is rather impeccable honestly because to get a real lead I just need the two of you." Crowley smirked and held out his hands gesturing to the devils trap below him. "Let's skip the foreplay and get right to the good stuff eh boys?" Sam sighed and scratched some of the paint from the devils trap away. "Don't strain yourself Samantha." He said as walked past Sam. "Now I've got a lead on a sort of, handler for the horsemen, a stable boy if you will, I'm just going to take a quick trip into one of your minds and replay your encounters with the horsemen for more clues. I'll have to sift through a few memories. Now seeing as when Sam died last he went to heaven, I'd like to avoid his mind, no demon has ever laid eyes on heaven and there's a reason for that. Squirrel I guess I'll be taking a jump into the deep end of your mind then?" Dean felt his face scrunch into anger. 

"No." He said aggressively. 

"Dean..." Sam said reluctantly. 

"You're not considering this! He's a demon Sam!" Dean said angrily. 

"I'm the most helpful demon you got." Crowley interjected sarcastically. 

"I'll be watching the whole time, if he tries anything, I'll stab him in his face." Sam looked pointedly at Crowley who made a kissy face in return. Dean sat down and glared at the demon. 

"I'll take that as a yes then." Before Dean could respond the demon put a hand on his forehead and everything went dark.

Dean heard Crowley's voice before he saw him. "I was right, it is a mess up here. Should've put money on it." He heard echoing in the dark. Suddenly he was looking at Crowley and they were standing in the library of Bobby's house. It was dark out. 

"Crowley what's going on?" Dean said, grabbing the demon by his jacket. 

"Would you relax? We're in one of your memories. I don't think it's the correct one but we have to see this because it's what you're thinking about in your sleep." Crowley pulled away and went to look around. "You're cute when you can't sleep Winchester." He said sarcastically. "Is that Feathers over there? Would you look at those wings!" Dean suddenly knew what memory they were in and watched as he saw himself get off the couch and walk carefully over to Cas. Crowley fell silent, watching intently. They watched as Dean stroked the angel's wings and Cas reacted. Dean blushed fiercely when he heard the Enochian, knowing now what it meant. Then Cas shuffled awake and Dean cringed as he watched himself stumble back to bed. Then the room faded back to black. Crowley gave Dean a smirk and a light shove, "That's kinky, Squirrel. I wonder what else you have floating around." He waved his arm and suddenly the memories of his battle with the horsemen War and Famine came back to him as if on fast forward and it took but a moment for Crowley to absorb. "Let's explore shall we?" Crowley walked off and Dean followed, trying to stop him. 

"You can't just traipse around in my memories." Dean yelled trying to catch him. Suddenly he was in a barn filled with weapons and covered in sigils. He looked around and saw himself. He saw Bobby laying on the ground, unconscious. Finally his eyes landed on Cas, standing just a bit too close to his past self. He knew where he was suddenly.

"Good things do happen Dean." Castiel said. He saw himself shift and his face harden. 

"Not in my experience." He said suspiciously. 

"What's the matter?" Castiel asked before pausing. "You don't think you deserve to be saved." He said softly. The memory faded back to darkness and Dean saw Crowley standing a few feet away, watching, and smirking. 

"He does make quite the first impression." He said before backing away. Dean made to go after him before he started hearing voices. His voice. Cas's voice. Sam's voice.

"I'm the one who gripped you right and raised you from perdition."

"I'm not here to perch on your shoulder."

"You should show me some respect."

"Our orders were to do whatever you told us to."

"I'm not a hammer as you say, I have questions, I have doubts."

"You made an exception for me."

"You're different."

"I want to talk to Cas, alone."

"I serve heaven, not man. And I certainly don't serve you."

"Man, you're a dick these days."

"I'll go with you."

"If there was ever something worth dying for, this is it."

"I'll be in touch."

"Hello Dean."

"Cas we've talked about this. Personal space."

"You're the only one who will help me."

"It's been a long time since I laughed so hard."

"What he said."

"It's kind of funny talking to a messenger of God on a cell phone. Kinda like watching a hell's angel ride a moped."

"This isn't funny Dean, the voice says I'm almost out of minutes!"

"Pretty nice timing Cas."

"Don't ever change."

"What's the deal with you and Cas?"

"Nothing is up with Cas."

"They're just freckles Cas, nothing special."

"Well I like them."

"Damn they're pretty."

"Please keep pleasuring me, ankem."

"An Enochian term of endearment, like sweetheart or lover."

The memories screamed through Dean's head all at once and at the end he could hear Crowley laughing loudly before everything went black again.