A/N: This one is as per Panda13216's request-a short one shot of Sam taking care of whump!Cas and whump!Dean.
I thought a lot about when to set this one and decided to set it in Season 5 Episode 3-Free to be you and me.
Sam opened the door to his motel room, still thinking about Lindsay and the dinner he'd just had with her. But it didn't take too long for his instincts to kick in. He wasn't alone; there was somebody in here with him.
Sam pointed his gun at the intruder and turned on the lights. He was so shocked to see Dean and Castiel that he almost dropped his gun.
"What are you guys doing over here?" He asked in a shocked tone and noticed a little too late that his brother and the angel weren't exactly in the best of conditions.
"Heya Sammy!" Dean said, clearly drunk. He stood up and stumbled a little bit when he walked towards Sam.
"Hey, whoa, whoa, whoa. Dean, take it easy," Sam said as he sat Dean down again.
"Hello Sam," the angel greeted, also sounding a little out of it.
"Hey Cas," Sam replied, "What happened to you guys?"
Before Castiel could even try to reply, Dean put a hand on Sam's shoulder and patted it, "Sammy, have I ever told you that you are the best little brother anyone could ever have?"
Even though Sam knew that Dean was drunk and was probably saying the most random things, he still felt tears welling up in his eyes. "No Dean you haven't." And I haven't been much of a good brother to you lately either.
"Well, I'm telling you now," Dean said, putting both his arms around Sam in a hug, "You're awesome!"
Sam could feel his shoulders tensing as he took Dean to his bed. Dean fell onto the bed heavily and closed his eyes.
"How did you guys get hurt?" Sam asked the angel who was still sitting on the edge of the couch, looking at the wall opposite him.
"The security guards beat us up," Cas muttered.
"The guards…why?" Sam looked at Cas, straight up confused.
"Because I told Chastity that her father did not run away because of her. It was not her fault." Castiel spoke in a matter-of-factly way.
"What?!" Sam had no idea what the angel was saying, which meant that the angel had to have been just as drunk as Dean was. "You know what Cas, we'll talk about this tomorrow. I think you need to get some rest right now."
"You are right," the angel replied as he got comfortable on the couch. Sam noticed the blood on his trench coat and on Dean's flannel but figured that the angel must've healed them both.
He shook his head as he saw Castiel closing his eyes, and got ready to sleep on the floor. Just then, he heard Dean calling out his name and felt his heart ripping to pieces. He'd never thought that he'd get to see Dean again, let alone hear him calling out his name. So he went near Dean's bed, "What is it Dean?"
"Have I ever told you how proud I am of us?" Dean asked the one question, said the one thing Sam had thought he'd never say again.
"No Dean you haven't."
Years later when Metatron slid the angel blade into Dean's chest with the Mark of Cain on his arm, he still remembered the events of that night and realised something. Castiel could have zapped them to any place at all, but he had specifically gone to Sam's apartment because he knew how stubborn the Winchesters were.
So as he spent his last few moments with his brother, he remembered that night and said, "I'm proud of us."
A/N: In my defence, I started off doing exactly what was mentioned in the request but I guess I went a little off the track. So Panda13216 does this count or should I do it properly in the next chapter?