Dean was the one who got them together. Though Dean had no clue of this fact. While Dean's foray into heavy drinking often came with a slurred observation or two, it didn't start getting embarrassing and awkward for Sam until Castiel started actually spending time with them outside of battling a monster or angel.
Well, okay, Dean always embarrassed him. But this was turning Sam into a red tomato, while he did more nervous chuckling than getting a word out.
So, it was all on Dean's shoulders. The innuendos. The slow smirk when Sam smiled at Castiel. The ridiculous giggling when Castiel looked mildly confused, but clearly not comfortable enough to actually ask what was going on.
Then came the day Sam had a strained shoulder and Castiel appeared with Dean, who somehow had kept hold of his large bottle of Jim Bean during flight and was in the goofy place between drunk and hugging the toilet. Sam sat there, shirtless and trying to massage his own shoulder awkwardly, thinking maybe the apocalypse was freaking Dean out more than he was showing. Which said a lot.
"Uhh, hi," Sam greeted, already feeling a blush building from the way Castiel was looking at him.
"Sammy," Dean sang, stumbling to his own bed. "I brought you a present. Cas, take off that coat and show him some skin."
"He's only been drinking, right?" Sam asked nervously. Dean didn't do drugs, but he also didn't question a drink from a girl with nice cleavage.
"I believe so." Castiel glanced at Dean, who was humming '8 Days a Week' to the ceiling. Castiel shook his head almost fondly before turning back to Sam. "Are you still in pain, Sam?"
"I'm fine," Sam said quickly. When Castiel frowned at him, clearly disappointed in Sam for not being honest, Sam sighed. "It's just this muscle. It keeps tensing up."
Castiel took a step closer to him, hand reaching out.
"No," Sam said, leaning back. "You don't need to use your mojo for this, Cas."
Castiel tilted his head adorably.
"Massage oil, you need massage oil," Dean mumbled, obviously on the verge of sleep as he rolled onto his stomach. "Just don't make Sam make sex noises in front of me." There was awkward silence, before Dean's head shot up and, in a clear feat of the mostly sleeping, hiccupped before saying, "Bet Cas is a top."
Sam realized his mouth was open in horror as Dean's snores echoed through the room. He couldn't look at Castiel. Not when his brother just talked about sex with the angel like it was a normal thing, because angels having sex happened all the time. Dear god, Sam hoped like hell Dean didn't remember this in the morning.
Sam squeezed his eyes shut and tried to not picture it. He usually managed to keep his imagination in check, never going past gentle kissing, but now Dean's words were circling his brain. 'Bet Cas is a top.' Sam bit his lip, because no. Not when Castiel was standing right there.
Then he felt the bed dip behind him and a soothingly cool hand rested on his pained shoulder. Sam jumped and looked back at him questioningly. Castiel, with those ridiculous eyes, blinked at him before beginning to massage the tense muscle, cause a grunt to escape Sam.
"Sam," Castiel said, tone deep and curious, "What does Dean mean when he speaks like that?"
"He's just being vulgar and teasing me, so don't worry about it," Sam mumbled, turning red.
Castiel's nimble fingers dug into what must have been an angry knot. Sam made a small noise. Castiel was silent a moment. "I wish to understand. Some of what you say makes no sense to me. I feel like I'm missing out on something. Dean appears to be making fun of us."
"Not you, just me," Sam replied with a sigh. He twisted around, ignoring that Castiel's knee now pressed against his thigh. "You should just ignore him. Just, please."
Castiel wasn't blinking, just staring with slightly narrowed eyes. Sam watched, mouth curling upward, as Castiel's head slowly tilted, a clear sign he was trying to understand yet another strange bit of human behavior.
Sam didn't have the heart to leave him confused. "Dean heard me talking in my sleep about you one night and seems determined to not let it go. So, it's not against you, he just likes making me uncomfortable."
"Was it a bad dream? I may have followed Uriel's view on you at first, but I no longer believe such things. I would never hurt you."
Sam was pretty sure his face was redder than it had ever been before. There was a grin trying to take over and he ducked his head down to hide it. "It was a good dream, Cas. A very good dream. Too good, actually."
"Why?"
"Because those dreams will never happen," Sam said bluntly, trying to shrug it off. "And…you're my friend. I shouldn't think of you like that."
"Like what?" Castiel asked. Sam shook his head because no way was he going to talk about his massive crush to the guy he was actively crushing on. No way. Castiel was starting to look frustrated. "Fine. I'll ask someone else."
Then with a rustle of feathers, Castiel was gone and Sam heard Dean's voice across the room, "Moron."
It was a while before Sam heard those wings again. For once it had been Sam driving them hard, hunt after hunt so he could lose himself in something he was good at. Instead of communicating with an angel. But soon, the fluttering hit his ears and Sam stiffened where he was reading mythology archives online, because Dean wasn't here to provide a distraction.
When Sam looked over Castiel looked different. He had a relaxed smile on his face as he fully faced Sam, like a guy that had had a good long think. "Hello, Sam."
"Hello, Castiel," Sam replied. "Dean's not here. He's—"
"I'm here to see you," Castiel interrupted. "When I left I was very confused. I ended up in Denver, Colorado. They were having a parade and I met some lovely people."
Sam's mind skimmed to what could be happening in later June there. Then he saw a flash of rainbow colors on Castiel's wrist as the angel reached up to run his fingers through his hair, a human trait that the angel didn't have before, and realized what that wristband meant. Sam nearly choked. "You spent a weekend at Denver's Gay Pride? I'm afraid to ask what happened."
And he really was. Castiel was practically innocent, minus the angel warrior thing. Who knew what a suave guy armed with alcohol and… something else that could have done harm to Castiel. Sam knew his thoughts were all over the place, but Sam could help it. It was Castiel. Angel of the Lord and total cutie, not to mention clueless.
"I met these teenagers who explained many things to me. They were not the sinful beings some of my brothers claim they are." Castiel stepped closer to Sam. "They explained what Dean's been saying to us. They told me what you meant concerning your dream."
Sam pushed his laptop away and dropped his head onto his forearms. It was a blessing Dean wasn't here.
"They wanted me to tell you that if you hurt me, they will strip your ass. I'm not sure what that means exactly, but—"
"Okay, Castiel." Sam looked up at the angel and drew in a breath. "I get it, but you haven't said what you think of this."
Castiel strode forward and dropped to one knee. He looked up at Sam with an expression that was far too open for an angel that swan dived into hell. And he was looking at Sam like that. Sam couldn't breathe as Castiel leaned upward, clearly to bring their faces more equal. Sam opened his mouth to speak, not even sure what he would say, before he couldn't speak at all.
Because Castiel, angel of the Lord, had their lips pressed together. Castiel made a surprised sound, like he wasn't expecting how it felt, and pressed in closer. Sam grabbed the lapels of his trench coat as Castiel's hands rested on his thighs. And it was amazing and Castiel kept making surprised and happy sounds and Sam was going to burst from how happy he was himself.
Soon, they had to pull apart for Sam to breathe. Castiel reached up and trailed his fingertips along Sam's cheek. "Dean was so bright and strong. He still is. His soul is one of the strongest I've seen. But you, Sam…what was done to you should have made you walk away, turn cold. You, Sam, have the strongest heart."