The first time Dean and Castiel kissed was an accident.
Or maybe it wasn't, Dean's not really sure.
It happened during the year they were preparing for the first impending apocalypse, and Cas' grace was depleting after every use. There was one day when he teleported to Bobby's to deliver news; upon his arrival, however, he promptly passed out in the middle of the floor, completely unconscious from overuse of grace. Dean volunteered to carry the sleeping angel to a bed, so he picked him up bridal-style (no small task, considering the guy felt like six feet of muscle and dead weight) and lugged him to a vacant room.
When he carefully dropped Cas on the bed, a soft snore escaped the seraph’s mouth as he shuffled around to get comfortable. And, even though the fact alone that Cas was sleeping was majorly bad, there was just something really... innocent about him currently. His face was smoothed over, and he wasn't stressed about the looming apocalypse or the fact that he was becoming human.
Dean didn't think. He just bent down and pressed a tender kiss to the angel's forehead before leaving the room.
It wasn't until an hour later that he fully grasped what he had done, but he couldn't bring it to himself to be sorry.
The second time they kissed was more of a mistake than an accident.
It was after Sam fell in the cage with Lucifer and Dean was living with Lisa. Cas kept a watchful eye on the ex-hunter. It felt almost scandalous, like a dirty little secret, watching over Dean like this. It was a reprieve for Cas to do it; in the very midst of what was rapidly becoming a massive heavenly civil war, it was pleasant to take a moment or two to just leave, to go and watch Dean - his charge, the Righteous Man - live his life, safe, away from hunting, away from war.
The angel would be lying if he said that seeing Dean so domestic didn't make him... feel, experience some kind of something that felt like a physical wound, despite the fact that his vessel was in perfect shape.
He was fairly confident that angels weren't equipped to experience these kinds of emotions.
One night a few months after everything went down was when it happened. Lisa was away on business, and Ben spent the night at a friend's house. It was the first night that Dean was alone in their home.
Cas observed silently as Dean picked up a bottle and didn't put it down until it was empty. Then he grabbed another. It wasn't long before he was too drunk to even stand properly.
From nowhere Cas felt an intense bout of longing emanating from the ex-hunter, certainly not an unusual feeling but absolutely the strongest since the apocalypse. It was at this moment that Dean stood, wavering on the spot, and took a step. His body apparently wasn't too appreciative of this movement, for he immediately toppled over. He hit the ground in a heap, the bottle in his hand smashing into pointed shards.
Dean picked up his hand to inspect it, and Cas saw a deep red gash.
Without a thought - of the fact that he wasn't supposed to be there, or that Dean might be angry to see him - Cas made himself visible to the injured man and flew him to his bed.
"Cas, 's that really you?" Dean slurred, apparently not sure if the angel was real or a figment of his imagination.
Castiel sighed and grabbed Dean's bleeding hand, holding it gingerly and almost intimately between his own, and sent a healing surge of grace to it.
"Is you. Cas," Dean said roughly. As Cas was leaning over him, trying rather unsuccessfully to maneuver him under the sheets, Dean grabbed his blue tie with his healed hand, yanking Cas, who was caught off guard, down to him, where Dean crushed their lips together in something far too uncoordinated and drunken to be called a kiss. If simply being here was crossing a line, then this... this was blatantly ignoring the existence of any such line. Cas knew this was wrong in every sense of the word, but he couldn't find it in himself to care too much, not when Dean was trying to kiss him as hungrily and needy as he was. But then the movement slowed down, and when Cas finally pulled back, Dean was snoring.
Cas knew the drunken man wouldn't remember this in the morning. He cleaned the broken glass up before he left.
The third time was for a case.
After Leviathan, after Purgatory, after the Fall, after Cas used up stolen grace and subsequently found his own again, after Dean became a demon. There's always something bad happening, an issue that required attention. And, sure, nothing was perfect now - they had unleashed the Darkness, after all, and had no idea what to do about that - but, individually, after Cas was cured of the attack dog spell, they were all (physically, at least) alright.
During this time there were still a number of smaller cases to take. While Sam stayed at the bunker doing research ("There has to be something we can do, guys"), Dean and Cas went to Illinois in search of a cursed object, which eventually led them to an auction held at a luxurious mansion in the country.
"I just can't believe people live in here," Dean said wondrously to Cas, taking in the chandeliers and staircases and how big and intricate everything was on the way to the room holding the auction.
"Some would likely say the same about the bunker," Cas reasoned.
It only took sitting through approximately five minutes of the auction for the two to realize that the best way to find their cursed object was to locate the holding room for this expensive merchandise. This also was not difficult since they followed the woman collecting the goods from the room to take to the auction. With a small burst of grace Cas unlocked the door and they stepped inside, where immediately the angel felt the power of the cursed object. Carefully Dean placed it - a ring of all things - in a warded box, and just that quickly, their job had been accomplished.
But they were still in the room where they couldn't get caught.
And they heard footsteps.
Dean knew they needed to hide somewhere, or do something that would make it look like they weren't stealing a priceless artifact, but there really weren't any good hiding places for two six-feet-tall men in this room. So of course the next best option to hide was in plain sight.
Within the span of a half second, Dean thought, Maybe we can look like two people who snuck off for some privacy, and he grabbed Castiel and began kissing him.
In the span of another half second the hunter had time to panic that this was the absolute worst thing I could've done, he isn't even moving, before suddenly Cas shoved him bodily against the nearest wall and was kissing back with everything he had.
And holy hell that was a lot.
It was a desperate kiss, needy, and this might be the best damn kiss I've ever had, and the pizza man did a damn fine job here, and he tastes like honey wow that's good to know, and this is so hot his body pressed against mine, and I'm getting hard just from this kiss I hope he doesn't notice, and wait are the footsteps getting closer, and -
"How did you two get in here?" a woman exclaimed.
Dean no longer had an armful of angel, which was pretty unfortunate considering all of his senses were urging him to grab him again and kiss him. They were both breathless, and Dean noticed with satisfaction that Cas' lips were red and swollen and his pupils nearly swallowed the dazzling blue surrounding them.
"We wanted some, uh, alone time," Cas was saying, which was great because Dean currently had zero brain cells available to think about why exactly they were kissing and what they were doing in that room to begin with. "It was unlocked. We just came in. We weren't paying too much attention to our surroundings."
She was glancing back and forth between the two of them. Maybe it was the frantic way they were kissing that had her convinced, or maybe it was the fact that Dean hadn't stopped staring heatedly at Cas yet, but then she was nodding her head and saying, "I think it's time for you boys to leave, and maybe go get another room."
She ushered them out, and they left willingly, cursed object in tow.
But they never talked about that kiss that left them both wanting more. Then everything happened with Amara, and Lucifer possessed Cas, and there was never a moment for just the two of them.
The fourth time was kind of on purpose.
It was two days after Cas narrowly escaped death in Ramiel's barn, and Dean was acting... strange. Well, strange in the fact that he had this determined look in his eye the previous night shortly after dinner, then promptly disappeared into his room; now, it was well past lunch, and Cas still hadn't seen the older hunter, and, as it turned out, neither had Sam. The angel was becoming slightly concerned. Was he ill? Did he leave without Cas knowing? No - the Impala was still in the garage, so Dean was still there. Was everything alright?
Just as he was about to go knock on his door, Dean appeared, hiding something behind his back. He came to stand directly in front of the angel, but didn't make eye contact; with the hand not hidden behind his back, Dean repeatedly rubbed the back of his neck. Cas recognized these habits as signs that he was nervous, but what is there to be nervous about? Is this about what I said in the barn?
He cleared his throat, intently staring at his shoes. "Cas - I - um - dammit, I thought I'd know what to say." Dean took a deep breath, his forest eyes met Cas', and the angel was reminded once again how beautiful this human was. "Look, man, I've been doing a lot of thinking since - since what happened, ya know. And - and I made you something."
And from behind his back he revealed a cassette tape. Deans Top 13 Zepp Tra xx.
He's giving me a mixtape.
Cas was momentarily too stunned to say or do anything - he was pop culture savvy now, he knew the connotations of being given a mixtape - and, apparently, he took too long to respond, because then Dean was shaking his head and saying, "You know what? This was a stupid idea, I'm sorry, I -"
"Dean," he interrupted, closing both of his hands around Dean's holding the mixtape, "thank you." And he leaned forward and placed a firm, tender kiss to Dean's bristly cheek, feeling the roughness against his own lips. He pulled back slightly, still technically holding hands, and they simply gazed at each other with looks that could only be described as loving.
Maybe it was actually going to lead to something this time, but they'd never find out, because in the next instant Dean's phone shrilled loudly, shattering whatever moment was happening between them.
Cas accepted the mixtape; but it wasn't long before he was off on his own again, on a quest to find the nephilim.
The fifth time was definitely on purpose.
Things were quiet for once. Sure, they were still in the process of training a hella powerful half-angel kid; there was the (probably) very real threat of alternate Michael destroying them all; Asmodeous, though wounded in a rescue mission, was still alive; and a 90% human Lucifer was in chains in the bunker’s dungeon.
But Sam and Dean survived Jurassic hell world, Jack rescued Mary from the alternate universe, and all together they freed Castiel, kidnapped Lucifer, and injured Asmodeous. So, for now, Team Free Will 2.0 - and Mary - were all alive and in the bunker, and nothing earth-ending was happening (yet).
Cas could've died, again, (and so could Dean, for that matter; they literally all could have), and he hadn't even recovered from the seraph's last death. So Dean decided that he wasn't going to wait anymore. If he wanted this, then he'd have to take it. (Or, rather, make sure Cas wanted it too.)
Cas was asleep when Dean found him, arms splayed on the table in the library and head laying close to his open laptop, sleeping like its user. The fact that he even is asleep (especially since it seems that he fell asleep accidentally) concerned Dean to no end; the angel hadn't talked about his most recent time in confinement, so Dean's pretty sure that that demon did something to him. Dean swore right then that he'd kill that evil Colonel Sanders next time he saw him.
"Cas," he said softly, taking a seat and gently shaking the angel's shoulder. "Cas, wake up."
And, well. In the amount of time it took Dean to blink, he felt the cold press of an angel blade against his neck, held by a bleary-eyed celestial being. "Oh, it's you," he said, deep voice made rougher with sleep. He replaced the blade in his coat.
(And he claimed that Dean was the angry sleeper.)
"You're sleeping now?"
"I healed a few more of Mary's wounds earlier," he explained, "and it must've exhausted me more than I anticipated."
Dean's heart was breaking a little bit. "Cas -"
"I'm fine, Dean," Cas assured, smiling slightly. "No need to worry."
The sight of sleepy Cas, smiling, with his trademark ruffled hair filled the hunter head to toe with an intense feeling of love.
"Are you - are you still tired? Do you need to recharge a bit more?" Cas hesitated before eventually nodding. Wordlessly Dean stood and nervously extended a hand to Cas, which he took immediately. Dean led Cas inside his room and closed the door. Alone, and more or less safe for once, they gravitated toward each other. Dean couldn't say for sure which one initiated it, just that now they were holding each other and kissing like it was the most natural thing in the world.
(And maybe it was.)
This kiss wasn't at all like the one they shared at that auction. This one was slow and filled with unspoken words: I love you, and you're mine, and we're going to make this work no matter the risk, and I'm never letting you go again, and I want you, and I need you, and this is our profound bond, and finally.
They separated, both smiling at each other with looks so tender, and Dean removed Cas' trench coat, suit jacket, and tie before pulling him to the bed where they both took off their shoes. Dean laid first, then pulled Cas on top of him, both holding each other as tightly and closely as their position would allow. Cas pressed one last sweet kiss to Dean's neck, and it wasn't long before they both were asleep.
The first time Sam saw them was the next morning.
Of course, as a person with eyes, he's known for years that Dean and Cas were hella gay for each other and pined more than a forest, but he just recently accepted that, though they've been married for years now, neither of them were ever going to admit it.
Sam wanted his usual cup of coffee that morning, but he paused in the doorway to the kitchen, hardly believing the sight in front of him.
Cas was standing at the counter, only in his dress shirt and slacks and with a pretty intense bed head, drinking coffee from a mug. Dean, similarly sleep ruffled, came up behind him, wrapped his arms around the angel's waist, placed a kiss on his cheek, and rested his chin on Cas' shoulder. Cas took one last sip from his mug before setting it down on the counter. He then turned around in Dean's arms and kissed him square on the lips.
Now, Sam's a smart man; he knew this was a private moment, not meant for a little brother's eyes. But he just couldn't not watch, especially after he's waited so long for them to get their act together.
Then, in a swift movement, Cas turned them both around and hoisted Dean up on the countertop by his thighs. Suddenly something that seemed so sweet turned desperate, and then hands started roaming and tugging at clothing -
Yep, this was Sam's cue to leave, which he couldn't do fast enough, especially after hearing someone moan. Time to go buy some bleach, for both that countertop and his own brain.