5 Times Dean and Castiel's Relationship Changed Unexpectedly (and 1 time it was completely expected)

A/N: This started as a drabble for a friend on tumblr and turned into a story! Ain't it funny how life works? I have horrible writers block with the WIP I have going, so I hope this will make up for the lack of updates. Beta'd by Lissie, of course. She's my spirit animal, and I love her for reading this through!

1.Dean had known Castiel for three months. Three months of having to wrap his head around the fact that not only were there Angels, but there was an actual devil. And if they didn't move quickly they'd be meeting him in the flesh.

It had been thee months of demons, and time travel, and Sam's freaky powers. Three months of Castiel's popping in and out of their lives. Often bringing bad news, often bringing pain. Hardship. More pain. And in all that time, Dean had hated him. He'd hated him and the responsibility he represented. And he thought that's how it was going to be with them. Until they saved the world or died trying, he'd forever resent his guardian angel.

And then it was Christmas. Sam and Dean had found a shitty hotel outside of some dump town and celebrated the same way they had the two years prior: gas station gifts and alcoholic eggnog. The tree in the corner looked like it'd been taken straight out of Charlie Brown's Christmas special, and the sandwiches they'd purchased were made on stale bread. But they couldn't have asked for more. Dean was smiling a genuine smile for the first time in awhile, and Sam was laughing at something on the TV when Castiel appeared. "Fuck me," Dean murmured, the Angel standing between them and the TV.

Castiel's head tilted, his eyes unblinking as he looked down at the Winchesters. Dean sighs softly, putting down his eggnog and looking up at him. "We don't even get a break for the holidays, huh?"

Castiel narrowed his eyes and shook his head. "I don't know that demons recognize Christmas as a holiday, Dean."

Rolling his eyes, Dean settled back into the couch. "Well," his eyebrows lift impatiently. "What is it this time? Another seal?"

"No, I'm here strictly to give you these," Cas set down the two paper bags on the table in front of them. Had he been holding those the whole time?

"What are they?" He heard Sam ask as he reached for the one in front of him.

"I know that it is customary for you, as humans, to give gifts on this day. Even though Jesus was not born in December…" he muses.

Dean blinks rapidly, looking at the bag and then back up at the angel. "Cas…did you get us Christmas presents?"

Castiel nods, his face unmoving. "Yes."

Dean looks over at his brother, who's pulling out a book from the bag he was given. "Castiel, you didn't…" he flips through the book. "Is this Moby Dick?"

The angel nods, "You'd said that you enjoyed books and wished that you hadn't lost them when your apartment burnt down."

"That's…wow, Cas. Thanks." Sam smiled a little, his hands running down the spine of the hardback.

Dean grabbed his bag and opened it, his eyes moving from the contents to Castiel. "You got me a record?" He asks in shock, pulling out the AC/DC record from the bag.

Castiel looked from Dean to Sam, his face finally showing a bit of confusing. "This is customary, correct? To give gifts to friends and family?"

Dean blinks again, swallowing thickly and nodding. "Yeah but…we didn't…I mean, I didn't know that…" He looks up and sighs. The only way to talk to Castiel was to be frank. That much he'd learned. "I didn't get you anything. I didn't know angel's had friends."

Castiel shrugged, the confusion replaced with his usual, tired expression. "I am coming to the conclusion that I am not like most angels."

Dean nods, looking back down at his gift. "Yeah," he agrees softly. "I don't think you are."

2. The next two months proceed in this new territory. This friendship that Dean hadn't expected. Nothing really changed, Castiel still infuriated him most of the time. But knowing that Castiel considered the Winchesters his friend helped Dean not to question his motives constantly. He still questioned them. Cas was a freaking angel, after all. But it wasn't a constant weight on his shoulders anymore, and he was grateful. Lord knows that he had enough weight there as it was.

It was a week after they had run into that siren. That fucking siren. Dean was still seething with rage. He hated having his brother used against him, he hated when his feelings were taken advantage of, and he really fucking hated being made someone's bitch. Even if they did win in the end.

Things with Dean and Sam were still a little awkward. They didn't talk much and when they did, it was mostly pleasantries. Neither of them were really angry and they'd both agreed to put the stuff they had said to each other that night aside, that it didn't count because they weren't in their right heads. But when words are said, you can't pluck them out of the air before someone hears them. They hang there, a constant reminder. And Dean and Sam both knew that they couldn't take them back.

So that's why he found himself in a bar. A bar on a Tuesday night surrounded by aging men with beer bellies and loose women whose self-esteem had hit rock bottom five years ago. He sat at the bar and drank his beer in silence, always preferred pity parties for one. So when he looked to his left and Castiel was sitting in the stool bar that had been empty two seconds ago, he jumped a little.

"Jesus Christ, Cas."

Castiel blinked at his reaction, his face unmoving. It was always unmoving. "I would really appreciate it if you would refrain from blasphemy while in my presence."

"Yeah? Well I'd prefer it if you'd start warning me that you're in my fucking presence. Then it wouldn't happen so much," Dean grunts.

Castiel nods swiftly, turning and looking at the wall of drinks behind the bar. "I heard about the siren."

Dean closes his eyes, sighing as he brings his beer to his lips. "Yeah, those things are just awesome."

Castiel's eyes go to the beer Dean is finishing and then to the bartenders. He makes a small gesture, holding up two fingers, and the bartender nods. "I am sorry that it caused you and your brother so much stress. I would have helped if I'd known."

Dean looks over at the angel, trying to hide the half smile on his lips. "You would've, wouldn't you?" He asks. Before he really realizes what he's doing, he reaches out and gives Castiel's back a firm tap with his palm. "Thanks."

Castiel meets his gaze and nods then looks up at the approaching bartender. He sets two beers in front of Castiel and goes over to another waiting customer. Castiel reaches up and grabs the beers by the neck, holding one up in front of Dean. Dean looks from the Angel to the beer before reaching out for it. Their fingers slide together and then apart as the beer passes from one hand to another, and Dean takes a long drink of his beer.

They sit, in silence. Because Castiel doesn't really know what to do or say, and thinks that maybe Dean just needs company. So they sit, and drink. And at the end of the night Dean shakes Castiel's hand.

3. Castiel had stopped making eye contact with Dean after the Alistair incident. The angel felt the Winchester's resolve fading; he could practically see the self-loathing dripping from his skin, and it was too painful to look at. Dean just moped around, drank, and watched re-runs of cheesy soap operas now. Sam was practically hunting on his own now, and Castiel popped in frequently to try and fill the void Dean was leaving.

Of course, after Zachariah's little stunt it was awkward for a whole other reason. It was Dean's shame that did it this time. His embarrassment for being so vulnerable in front of the angel. Castiel had told him, after he came back from playing businessman, that it was not an issue. "I'm not here to judge you, Dean." He assured the hunter.

And yet, he felt judged. He felt weaker in the angel's eyes, and for some reason that bugged the shit out of him. So, he went on a killing spree. Anything evil and with a pulse was game. He barely slept, spending most nights on the computer doing research on the monster of the week. And Lilith. Always Lilith. That's what he was doing at 2 in the morning when Castiel popped into the room. Sam was asleep in his bed, the TV flickering dimly in front of him. "Hey Cas."

Dean had gotten pretty good and sensing when the angel appears. It's actually becoming some what of a sixth sense, thank you very much. He looked up to see a worried face looking back down at him. That's something he might never get use to, the sudden emoting of the angel. He had been so use to the unmoving face of Castiel's vessel. But after Alistair though, it seemed like every little emotion Castiel felt was displayed, like a neon sign, on his face. "Dean."

The angel was leaning against the tiny excuse for a kitchen that the motel room came with, and his eyes watched as Dean scrolled through the information on his computer. His eyes slowly went from the screen to Castiel's face, his eyebrows arching in curiosity and a hint of frustration. "Something I can do for you?"

Cas blinked, his gaze going to the hunters face. He's silent for a little, Dean watching the wheels turn in his head. "You're worrisome."

Dean frowned, pushing back into his chair and folding his arms across his chest. "I am? How so?"

The angel moved to the chair across from Dean, straddling it. "I do not know if all humans are like this. The self-awareness, and desire to prove ones self. You have proven to not be like most humans."

Dean blinked, opening his mouth to respond only to shut it as Castiel continued. "I understand your new drive to defeat Lilith. I can appreciate the desire to finish this. However, if you keep going at the rate you are going…you are not going to be good to me when you are actually needed to fight."

Dean leaned forward, his eyes narrowing. "Bullshit, Cas. I'm always ready for a fight."

Castiel nodded. "Yes you are. You are always physically ready for a fight. But you're mental state needs to be sharp too. I fear you are over working. I fear that in an act of desperation to find focus, you've lost it."

The hunter gaped at the angel, his jaw slack. "You're saying I'm too devoted? First I wasn't committed enough, and now I'm throwing too much effort into it? What exactly do you want from me here, Castiel?"

He was unable to deny the way Castiel winced at his name. When they fought he never shortened it, and it had grown to be a bit painful to hear. The angel cleared his throat. "I want you to be 100 percent ready for whatever is coming. I am all for you learning all you can. But I do not think it requires you to skip sleep, or kill anything that moves." He said firmly. "As a friend, I'd prefer not to see you die after all of this, Dean."

The anger in Dean's face broke at that, and he leaned back in his chair with a huff. He looked at his computer screen and his notes, then down at his watch. With a heavy sigh, he reached out and closed his laptop. "Yeah, okay."

Castiel stood, and Dean swore he saw a trace of satisfaction in his eyes. "I appreciate you listening to me."

Dean stood as well, figuring he'll go to bed once the angel mojos out of here. "Yeah well, if I hadn't, I'm pretty sure you would've kept harping until I did."

Castiel stood for a moment, his eyes dimming as he mulls something over in his head. Then, without warning or invite, he came around the table and wrapped his arms around Dean. "What…"

Dean stood there frozen, his hands pressed firmly to his side and his eyes wide. He thinks maybe if he stays still that the angel will get the hint, but he doesn't. Reluctantly, he raises his hands to place awkwardly on Castiel's back. But he found an odd since of comfort wash over him, and instead he melted into the hug. When the angel pulled away, Dean looked at him in amusement. "What was that?"

Castiel frowned. "It is custom to hug after an important discussion such as that one, correct? It reaffirms the knowledge that we are on each other's team."

Dean smiled a little at that, patting Cas on the shoulder. "Yeah. Yeah, we're on the same team."

4. Humanity is a funny thing. Watching an angel start to mirror humanity is an even funnier thing. Dean's pretty sure that's why he was so mad at Castiel when he learned the angel's plan for the seals. He'd been so convinced, so sure that Castiel was starting to show signs of humanity, that when he learned that he was just following orders, it hurt. It hurt more than he'd admit out loud. Betrayal left a bitter taste in his mouth though, and he needed to get rid of it.

So when Castiel chose to help him, when he defied heaven in order to get Dean to his brother, he was filled with an emotion far more powerful than betrayal. He didn't have a name for it, and if he did, he wasn't going to say it out loud. But suddenly the angel was in focus. Dean saw him crystal clear. And even though he was scared of the apocalypse, and of what Sam was becoming…this almost scared him more.

Then the box was open, Lucifer was free, his brother was a shadow of himself, and Dean just wanted to see Castiel. To hug him, because he can do that now. He wanted to hug him and thank him for coming through in the end, when most didn't. The idea that he might've been a casualty, that he might not have made it didn't even enter his mind. "You're sure? I mean maybe he just vanished into the light or something."

Dean was grasping at straws, and Chuck was killing his hope. "Oh, no. He, like, exploded. Like a water balloon of chunky soup."

Dean winced, his eyes turning to the floor. Sam was saying something to Chuck, but all Dean heard was his heart bounding in his chest. He needed to stay calm. He needed to focus and breath. Don't forget to breath. The apocalypse was still in full swing, Zachariah was still a douchebag, and Castiel was still dead. So he kept going. He does research and fights. Because even if everything was slipping away, his sense of responsibility over humanity kept him going.

The blows kept coming full force. Bobby's possessed and then seriously injured, and that sword. Michal's sword. It isn't an actual sword. It's him. He's it. He's a vessel. And he almost had to laugh. He's so overwhelmed and bogged down and he wants Castiel to come back, he almost has to laugh to stay sane. Of course he refuses. Of course he tells Zachariah to go fuck himself. And of course Zachariah inflicts pain. He's writhing on the floor with his brother, spitting out blood and almost relieved at the possibility that it might end. Even if it's at the hands of this unbelievable tool. And when there is bright light, he almost thinks it's heaven. That he is dying. But he can hear voices and his eyes snap open at the familiar gravel tone that belongs to the angel of Thursday. And then Zachariah is gone and so is his pain, and he gets on his feet slowly. Castiel's hand is on his elbow to steady him and Dean's hand latches to his forearm automatically. "You're alive," He breathes.

Castiel smiled a little as their eyes meet. "I am."

And that's it, Dean closes the distance and they are connected. His lips pressed firmly and desperately to Castiel, the angel going still against him. He pulled back after a moment, his face slightly flushed. "Sorry."

Castiel blinks, his wheels turning like they did when he's contemplating humanity. His blue eyes meet Dean's gaze again. "I did not do that right." He finally stated. "Do it again."

Dean's eyebrows rose in shock and amusement. "You want me to kiss you again?"

"Yes," his answer was immediate, and his grip on Dean's elbow tightend a little.

Dean licked his lips, taking in a shaky breath before leaning forward and capturing Castiel's lips in another kiss. This time Castiel's lips latched onto his, and he felt Castiel pulling him closer by his elbow. He sighed softly as their lips moved against each other's, his whole body on fire. When they disconnected Dean was breathless, panting softly as he watched Castiel process what just happened. The angel stood still for a moment before his lips turn up in a small smile. "I think I enjoy that form of contact more than the hugs. We should do this instead."

Dean wasn't going to argue.

5. As good as it felt to kiss an angel, Dean couldn't have picked the worst time to do it. They shared three more before shit really hit the fan, two of which were interrupted by Bobby. The third was after Dean gave Castiel his pendant. Their words were heated and biting, both suffering from the weight of responsibility and abandonment by the ones they loved most. As soon as his hand was in Castiel's to give him the pendant, their fingers clasped together. Dean yanked Cas forward urgently, their lips meeting in half open gasps of excitement and anger. Bobby and Sam sort of averted their eyes as the angel and hunter pressed into each other and devoured each other's lips greedily. They parted after a moment, baited breath and swollen lips. And then Castiel is gone and Dean doesn't see him again for three weeks.

By then Sam is gone. Dean is alone. Hunting, drinking, and women fill his time. When Castiel appears to him again he's a bit hung-over and very bitter. "How's the search for Daddy going?"

Castiel averted his eyes, clearing his throat. "That's why I'm here," his eyes landed on Dean's. "I need your help."

And that's how he found himself here, in a run down old house with an angel who seemed to have either a death wish or was already running on desperation. He couldn't tell which, but one thing was for sure; Castiel doesn't plan on walking away from this. The idea of death didn'tt scare Dean. It couldn't really, when you have a job like his. For some reason though, the idea of Castiel's death was very unsettling. He stood silently in the dark room with the one thing in his life that'd been somewhat consistent and he didn't want that to die. His eyes stared into the back of Castiel's head as he thought, and he couldn't stop himself from asking: "Last night on earth. What…uh…what are your plans?"

Castiel looked over at Dean from his seat, his expression one of tired defeat. "I just thought I'd sit here quietly."

"Dude, come on. Anything? Hm? Booze? Women?" Castiel shifted uncomfortably, his eyes falling back to the wall opposite him. Dean leaned forward a little to study the angels face, his eyes squinting in concentration. "You have been with a woman before, right? Or an angel, at least?"

Cas shifted again, and Dean gaped. "You mean to tell me you've never been up there doing a little cloud seeding?"

Sighing in frustration, Castiel's eyes finally came up to meet Deans. "Look, I've never had the occasion, okay?"

Dean stood up straight, blinking at the idea of Castiel dying without experiencing a connection like that. It was utterly human, sex, and Castiel had been heading toward humanity with such rapid acceptance that Dean felt a little sad at the idea of him missing out on this. His eyes go back to the angel's face and his mind makes the decision for him. He shook his head, moving to stand in front of Castiel. "No, I'm not going to let that happen."

Castiel looks at him in genuine confusion. "Let what happen?"

"I'm not going to let you die a virgin."

Cas' shoulders slump, his eyes rolling. "Dean I do not wish to go look for women with you."

Dean shook his head, letting his body move before he can over think anything. He sunk to his knees in front of Castiel, his hands landing on the angel's knees. "No, no. That's not what I was suggesting."

Castiel's eyes searched Dean's face, blinking rapidly. "Dean," he warned.

"Just…" Dean interrupted him, squeezing Castiel's knees. "Just let me do this for you, okay? Let me give you the rest of your humanity. Please?"

Cas sucked in a sharp breath, his hands gripping the edge of his seat. After a moment of unblinking eye contact, Castiel nodded and Dean surged forward to capture his lips in a kiss. In the end, Castiel doesn't die. But if he had, he wouldn't have gone out a virgin.

6. It turned out having sex with an angel was rarely a one-time occurrence. At least that's the case for Dean Winchester and his angel. After their first night before confronting Raphael, they both tried going back to just kissing. Kissing wasn't as scary, or intimate, or raw. Sam was back, and they were hunting the devil full force. Both Castiel and Dean thought that the denial they had chosen was going to be easy. Who had time to fuck during the apocalypse?

Turned out, they did. They had gone two months without bringing it up at all, but then Jo and Ellen were gone, going out in a blaze of glory, and for what? "The cause?" Dean was angry at "the cause." He was angry and Cas was frustrated that he couldn't help. He wasn't any closer to finding God and the pity party they were having turned into sex: quick and rough in the back of the Impala after a hunt, and after that they couldn't stop.

Sex after Anna's attempt at killing Sam and Dean's parents, sex after Famine, sex after Dean returns from heaven, drunken sex after that whore (literally). If asked, they'd both say it was out of convenience and comfort. Nothing more. Their loss of hope was almost parallel, and with Castiel's rapid turn from angel to something resembling a human, it made sense for them to be there for each other in that way. Who else would understand your stress about the apocalypse than the guy fighting with you?

It wasn't until Dean hit rock bottom that either of them acknowledged what it really was. Castiel hit him over and over in that alleyway, and all Dean saw was the pain in the angel's eyes. The hurt and betrayal in his voice. That was more devastating than the beating. And then Castiel had to go and play hero, potentially sacrifice himself for the fucking cause, and Dean didn't know what to do with himself. This might be the last time he saw the angel, so he did what came natural. Before Castiel entered the warehouse, Dean pulled Cas into him and kisses him. "I know you're disappointed in me," He mumbled softly into his lips. "But just…come back. Okay? Please."

The angel blinked at how vulnerable Dean sounded, and nodded mutely. And then he was gone for a month.

When Dean answers his cell phone and hears the familiar gravel of Castiel's voice, he melts into his seat. "Cas, Jesus."

"Hello to you too."

He wanted to sob. He wanted to say how sorry he was, how fucked up their relationship had been. He wanted to hug him, and kiss him. He wanted to feel his body pressed against him again. He wanted so much at once and he's so wrapped up in his thoughts that it takes Castiel's voice to snap him out of it. "Dean? Are you there?"

"I love you." He sighed. It falls out of his mouth without thought.

Sam and Bobby were watching him, mouths open in surprise. But Dean sat comfortably. He didn't regret it, he didn't take it back, and he didn't care if Castiel sid it too. He just needed it out there. After all the shit that'd happened since Castiel first showed up, after all the close calls and resurrections, he needed to say it. Because one of them could die and not come back, because the world was ending, and because Castiel had blue eyes and messy hair and a lazy smile he only gave to Dean after they'd have sex.

"I love you too," Castiel responded, voice soft and sure.

Dean's eyes closed and he let out a small, content sigh. The world may be ending; he might die tomorrow. But right now in this moment, for the first time in years, Dean was content.