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Dean Winchester Wins Everything, Even Gay Chicken

Summary:

Dean Winchester never backs down from a competition or a bet. So, when Castiel kisses Dean in the car, the two start a competition with no clear guidelines or winner. They go back and forth, each exchanging affection with one goal: to fluster the other as much as possible. Dean is determined to win, even if it means that he spends the majority of his day thinking about kissing his best friend. But as the competition continues, it becomes harder and harder for Dean to ignore the truths he's been shoving aside for so long.

But Dean Winchester wins everything. ESPECIALLY gay chicken.

Notes:

I decided to make this a two-chapter fic because this chapter is already 4k words and I wanted to post it. If you can't tell, I'm not fantastic at writing fluff, but I am literally so in love with these two and their dynamic that I wanted to explore what it would be like to have them skirt around their feelings. If you want to listen to the song that they hear while dancing, you can just listen here:
https://www.youtube.com/watch?v=VJcGi4-n_Yw&ab_channel=OldiesZone
It's definitely a popular one for Destiel fics, but I adore it and think the song is just perfect. Things are going to get a little angsty for the second chapter (because I'm an angst writer, it's what I do!) but I think it'll be good and I'm excited to finish it :)

Chapter 1: Earth Angel (Will You Be Mine)

Chapter Text

If there was one thing that Dean knew about himself, it was that he never backed down from a challenge. He’d managed to make a fool of himself many a time from taking a stupid bet and refusing to back down. Did he manage to often save his life and the lives of the people he loved as well as the world, once or twice because of it? Yeah, yeah it did. Did it also mean that there was a picture of him out in the world wearing a chicken suit while seated in a fancy restaurant?

Not that he’d ever tell you.

So when the challenge had started between him and Castiel, Dean sure as hell wasn’t going to back down. He wasn’t going to give in, no matter what happened. 

It had started innocently enough; Dean and Cas had been doing a stakeout to uncover a vampire nest while Sam recovered from the flu in a motel room several miles away. It had been a slow, uneventful week full of dead ends and dead bodies. But Dean had a good feeling about that night, about that stakeout. He felt, for certain, that something important was going to happen.

And so he and Cas had sat in the car, idly talking, waiting for the vampire to show himself so they could follow him to the rest of his group. It was comfortable if not domestic and the weight of sleep was clearly starting to take a toll on both of them.

It wasn’t until Cas had stopped mid sentence to say “There. I see him.” that Dean had swung his head to stare out the window to stare at the vampire.

Who had seen both of them staring directly at him.

They watched the vampire tense, holding eye contact for what felt like forever, before Cas hissed “Dean, he sees us!” and the vampire took a slow step towards their car, hands beginning to curl.

Without any warning or notice, Cas’ hand shot through the air, cupped Dean’s cheek, and turned his head to pull him in for a kiss.

At first, Dean had been absolutely surprised and had tensed up. But then Cas’ hand softened against his cheek and Cas’ other hand crawled to rest on his knee and suddenly Dean was resting his hand on Cas’ shoulder and the other on his cheek and he absolutely melted into it. It felt perfect, like the stars were exploding in a kaleidoscope of colors and shapes and every neuron in his brain was firing at once. He feels an eruption of adrenaline shoot across his skin, leaving goosebumps on every single square inch. 

And then, suddenly, Cas was gone, calling something over his shoulder as he tore out of the car and slammed the door behind him. He left Dean there, stunned and dazed and breathless, his heart beating faster than it had ever beaten before and his hands shaky and his mouth tingling and his fingertips numb. 

Dean only needed a few moments to haphazardly stumble from the car and run to catch up with Castiel, but the shake in his legs and the anxious, fluttery feeling underneath his skin never died down. Even after they had taken care of the nest of vamps and had returned to the car, Dean felt different sitting in the driver seat. The leather underneath him felt different, somehow, like Cas kissing him had somehow rearranged the molecules to make the seat more comfortable. 

They had driven halfway back to the motel when Dean decided to cut through the dead air. 

“So… you kissed me.” Dean said lamely. How else was he meant to start this conversation?

“What an astute observation, Dean.” Cas says in the monotone voice that anyone else would read as dismissive but Dean knows to be playful. 

“Why did you kiss me?” Dean itches with anticipation and a healthy dose of terror.

“The vampire was coming towards us.” Cas says, and Dean can hear the nonchalant shrug. “People get embarrassed by grandiose public displays of affection. Vampires included, evidently. I made a split-second decision because I panicked. I apologize.”

“Well, at least you were right.” Dean said, slightly disappointed. Of course Cas hadn’t kissed him because he legitimately wanted to, he kissed him because it had logically been the best way to handle the situation.

“Why, did you have something you wanted to say about it?” Cas said, the teasing tone under his voice.

“I would rate it a solid four.” Dean sniffed, pretending to be uptight about it. “You have plenty of work to do on your form.”

“Well, then I suppose you’ll have to show me.” Cas shot back with the same amount of flirty coyness that made Dean’s stomach cartwheel. 

They always did this. The little half-flirting dance around each other in which they would come so near to what they both wanted but would refuse to take the final step into the deep end. It was so infuriating yet so safe that neither Cas or Dean felt that they would ever escape it. It was like a permanent limbo for their relationship. Mostly friends and almost something more, but doomed to never be able to find out what lay beyond it.

“You do know that this means that now I’ll have to get you back, right?” Dean says, raising an eyebrow even though Cas can’t see him in the dark. 

“‘Get me back’?” Cas scoffs. “What does that even mean?” 

“Oh, you’ll see.” Dean says mischievously. 

They dropped it after that. Cas didn’t push it and Dean didn’t want to give way to the fact that he was legitimately serious. He couldn’t tell if Cas had meant anything with that kiss. Kisses often didn’t mean much to people, and to Cas, who was newly human and still grasping the concept of a toaster, it would make sense that he couldn’t understand how his action could be interpreted. But regardless, Dean wanted to do something that would make Cas as flustered and as in shock as he had been. Not in a revenge type of way, but also totally in a revenge type of way.

Turns out, he hadn’t had to wait very long to have the perfect opportunity to get back at Cas. 

After a case had gone particularly well, the trio had stopped by a bar in the town they had recently saved from a banshee on their way back to the bunker. Dean had been itching throughout the entire case to enact his plan, and as soon as Sam had excused himself to the bathroom, Dean took the opportunity to strike. 

He had scurried off to the bar to grab them some more beers while Cas stayed behind to “guard the table”. Really, though, he had only managed to attract the attention of a young, pretty waitress, who currently had Cas huddled as far as possible from her in the corner of their booth. From the way she tossed her hair and reached out to touch Cas when she laughed, Dean could tell that she was totally flirting with Cas. 

Bingo.

Dean did his best not to almost sprint across the bar, slipping past the waitress and into the booth seat in one fluid motion. He set down the beers and then grabbed Cas by the tie, roughly pulling Cas in for a kiss. He pulled away a second later, not giving Cas any time to get used to the embrace, before he turned back to look at the slack-jawed waitress, who muttered a string of apologies before she ducked away back into the kitchen.

“What-” Cas starts and when Dean looks back with a smirk, he sees the same bewildered expression on Cas’ face that Dean must have had when Cas kissed him in the car. Grinning, Dean had leaned in so close that he could see his breath moving the hair on the back of Cas’ neck. One of his hands gently rested on Cas’ knee, rubbing circles with his thumb. In as low of a voice as he could muster, he whispered: “Checkmate. Your move.” before pulling away, winking, and heading out to the car. He got to the doorway before looking back, gleefully seeing Cas with his eyes wide and his mouth slightly open. 

If only Dean had known what that one little competitive move would snowball into.

 

He hadn’t really expected Cas to continue the little “game”. He didn’t really think that Cas was chicken, more that he wasn’t really all that interested. Dean had slept easy, knowing that he had won yet another competition. 

But then they were working a case in California. A suspicious set of murders inside an apartment complex that seemed to point to a ghost. Dean and Cas had been sent in to pose as people interested in renting the apartment below the one in which the murder had taken place as a way of gathering intel. 

The realtor had been the regular type; too cheery, words dripping in fake positivity, and a big smile that either meant plastic surgery or the strongest cheek muscles known to mankind. Dean was going to guess the former. 

But when she had asked them what made them want to move to the area, Cas enacted his next move. One arm snaked around Dean’s hips, pulling the sides of their bodies flush together and his hand drifting down low enough to make Dean’s heart leap and skin crackle with electricity. Okay, fine. Cas wanted to play that way, then Dean could handle that. He wouldn’t give Cas the satisfaction of seeing Dean get flustered over simply brushing over his hips. 

Then Cas had followed it with the most doe-eyed, loving look at Dean before turning to the realtor and promptly saying: “My boyfriend and I are finally ready to move in together. We’re so excited for this step in our lives.” Before tossing another one of those sappy looks in Dean’s direction.

Dean was a strong guy. He could withstand torture, Hell, Purgatory, even airplanes. But hearing Cas call Dean his boyfriend so easily, like he had said it a million times, followed by a look straight out of a shitty rom com makes Dean’s knees buckle and the room start to sway a bit. If this were a cartoon, there most definitely would have been tiny cartoon hearts floating around Dean’s head and in his eyes.

Clearing his throat, Dean fought down the pink blush that crossed his cheeks and nodded along with what Cas and realtor were discussing, despite only being able to hear his own quickened heartbeat in his ears. After Cas finally released the iron-grip he had on Dean’s hips, he made sure to snatch Dean’s hand and entwine their fingers as the realtor gave them the final walk-through of the apartment.

Touche, Cas. 

But that meant that the game was on and Cas was playing to win. Dean couldn’t let him do that. Not once did Dean slow down to question anything he was doing. Why would he have to? It was just a silly competition, right? There were definitely no hidden feelings behind any of this nor any secretive motivation. That would be crazy and Dean had a handle on things. 

And if winning the competition meant that he spent the majority of the day thinking about kissing his best friend, well, then so be it.

He got Cas back when they were working a case in a city a few towns over from where they’d been before. After catching a glimpse at the FBI badge that Cas had intended to use, Dean had grabbed his with the same last name. Perfect. From there, they had gone inside to meet with the coroner, a quiet lady with long brown hair and a kind smile. They had flashed their badges and Dean had sweetly said: 

“Agents Watson and Watson. Could we please have all records pertaining to Mr. Dickey’s death?” which had turned Cas’ head a little bit.

The coroner had grinned and looked between the two of them, beginning to lead them to where the files are kept. 

“Agents Watson and Watson, huh?” She had said as she walked. “Any relation?”

“Marriage.” Dean says with a grin, throwing a look at Cas. “We were married a few months ago and I’ve never been happier.” Cas’ eyes widen slightly, enough that is almost imperceivable to the coroner, but Dean can tell that it got to him. He even runs his hand up and down Cas’ back as they walk and he can feel Cas tense underneath him, radiating with flustered energy.

“You two are a cute couple.” She handed Dean a file with a nod and a smile. “Glad to know you are both working so diligently on our case.” With that, she had left, and Dean and Cas said nothing about what had happened.

They ended up ganking the monster that had been siphoning blood from hospital patients and that was that. They were on the road again, heading back to the bunker to meet up with Sam. 

From then on, almost every case they worked turned into a competition for who could get the other to chicken out. 

Cas got Dean back by sitting on his lap in a diner and leaning his head back against Dean’s shoulder.

Dean got him back by resting his head on Cas’ lap on the couch while they went over files and watched a movie.

Cas got Dean back by hugging Dean from behind while Dean made breakfast one morning.

And during this entire ordeal, Dean had shoved down all the rising feelings. The adrenaline under his skin was because of the thrill of the competition, not because of the way Cas’ skin felt against his. The fluttering of his stomach whenever he made eye contact with Cas was because of their faked rivalry, not because Dean felt like he was the only person in the world when Cas looked at him. The way his heart leapt when Cas used words like “my boyfriend”, “my love”, “my fiancé”, to describe Dean was because they took him by surprise, not because they felt so right and like the missing piece of the puzzle Dean and Cas had created. He refused to acknowledge what all those feelings truly meant because that meant that Dean had to come to terms with the fact that this wasn’t just for fun. And that was much scarier. That meant denial and pain and having to keep yet another secret from Cas. And so, if he just didn’t address it, if he lied to himself about what these things really mean, then Dean could just avoid it all together.

Until it was his turn to get Cas back and suddenly, everything changed.

Sam was in his bedroom taking a nap and Dean and Cas were sitting in the library, once again poring over old files and dusty books. The record player sat in the corner, playing a playlist of songs that seemed to fade into the ambience of the room. The hazy glow of the lights illuminated the room and a fuzzy, warm feeling held thick in the air. Whether from the bit of alcohol the two had already had or just from the way the room normally was, it always seemed to tug your guard down and make everything more fun.

The song on the record switched and suddenly a piano and melodic voices filled the room, singing rhythmic “oh”s to open the song. Dean was on his feet in an instant, hovering over Cas’ table with his hand outstretched. When Cas looks up, he sees Dean, illuminated in the warm glow of the bunker’s lights.

“Care to dance with me?” Dean asks. Usually, Cas can tell when is trying to ‘get back at him’. There’s a lilt to his voice, a twinkle in his eyes. But this? This is just Dean. And whether it’s a part of their little game or not, Cas reaches his hand out and lets Dean lead him to the wide space in front of a bookshelf. 

“Have you done this before?” Dean’s voice is soft and Cas shakes his head no. Immediately, Dean’s hand snakes around Cas’ waist, tugging him in so that their hips are flush and their chests are centimeters apart. He guides one of Cas’ hands up behind his back and pulls the other one into his free hand, which Dean holds out a small distance away from them. Dean rocks them gently back and forth, their bodies fitting together so perfectly that Cas almost blocks out the music entirely.

Earth Angel, Earth Angel, will you be mine?

Cas snaps to attention immediately. It makes sense why Dean would pick this song to dance to. Did he recognize it? Is that why he pulled Cas up to dance? Did that mean Dean regularly listened to love songs, enough to recognize a love song about an angel?

“You’re so tense.” Dean breathes. “Relax. I’ve got you.” And those words, the promise of the embrace, of Dean around Cas, causes Cas to release a breath and sink into Dean. Without any concept of what is correct or what is wrong, Cas rests his head on Dean’s shoulder nuzzling into the point where his neck meets his torso.

“My darling dear, love you all the time.” Dean mumbles the lyrics under his breath and Cas can feel the vibration in Dean’s chest, emanating out and pooling in Cas’. The room is warm and Dean holds Cas securely. Warmth floods every single part of Cas, spreading from his toes to his fingertips. It clouds his head and makes him a bit unsteady on his feet. Or, at least, it would, had Dean not been holding Cas so securely. 

“I’m just a fool, a fool in love with you.” Dean continues to sing along, the hand that is holding Cas’ rubbing Cas’ hands with his thumb. 

“I fell for you, and I knew the visions of your loveliness.” Dean moves them around the room, swaying and spinning until they’ve danced across almost every open inch of floor.

“I hoped and I pray that someday I’ll be the vision of your happiness.” Dean’s hands shift and suddenly he’s slowly spinning Cas around, pushing him out and twirling him in one fluid motion before he’s tucking Cas back into his body again, encouraging Cas to rest his head on Dean’s shoulder once more.

“Dean.” Cas’ voice chokes in his throat. What could he even say? How could he even put this feeling into words? This deep, burning, bubbly, intoxicating warmth that spreads from the inside out and clouds his mind with pure happiness. 

“You know, have I ever told you my favorite thing about music?” Dean asks softly, pulling Cas away gently so they can look at each other. God, in this light, Cas almost has a halo around him. Despite being human now, Cas looks ethereal. He looks strong, powerful. He looks more beautiful than Dean has ever seen him. A flash of confidence, perhaps misplaced, suddenly courses through Dean.

“No, I don’t think so.” Cas mumbles, his eyes locked on Dean’s.

“If there’s something you want to say, and you… you don’t have the guts to say it.” Dean says, swaying still. “Music can say it for you.”

“That is the beauty of art.” Cas agrees. “I have found many songs like that.”

“God, you’re beautiful, Cas.” Dean says suddenly, biting his lip slightly. 

“No. I don’t have my grace.” Cas begins to look away, ashamed, but Dean’s hand catches his chin and turns him back to look at Dean.

“You don’t need it. You’re perfect.” Dean leans forward, pressing a soft and gentle kiss to Cas’ forehead. Cas can almost swear he hears Dean tack on a quiet “my Earth Angel” to the end of the sentence. 

“Dean.” Cas says, pulling back slightly so that he can look Dean full in the face. “There’s something I need to tell you.”

“I’m all yours, Cas.” Dean says softly. 

Cas wants to tell Dean that he doesn’t want to keep playing this game. He wants to tell Dean about the extent of his feelings and the way that he feels when Dean walks into a room. He wants to tell Dean that he can’t stop thinking about him and how amazing it feels to have spent all this time with him. He wants to tell Dean that he doesn’t want this game to just be a game. He wants it to be their reality, all the time.

He wants to tell Dean that he is in love with him and has been from the beginning.

Instead, he catches movement out of the corner of his eye, and sees Sam standing in the doorway, watching them. Dean’s head turns to follow where Cas is looking and he immediately steps back, leaving Cas alone and cold. 

“Sam.” Dean’s voice changes, no longer the same soft, quiet voice he’d used with Cas. Now, it's back to the regular gruff, business-like voice. 

“Dean. A word?” Sam asks, gesturing for Cas to head out. With a thin-lipped smile, Cas rests a hand on Dean’s shoulder as he walks from the library, hanging onto the last few measures of the song as he heads down the hallway and into his bedroom.

“Creep much?” Dean grumbles as soon as he’s sure Cas is out of earshot.

“You can’t keep doing this, Dean.” Sam sighs, leaning against the doorframe.

“Doing what, Sam?” Dean shoots back. He’s too defensive, but he’s embarrassed that Sam caught him and Cas in the middle of dancing. It was supposed to be a private moment, but Sam had to come along and ruin it.

“Leading him on. Using him. I don’t know what it is. But it’s not okay.” Sam says.

“You don’t know anything, Sam.” Dean scoffs.

“I know that Cas doesn’t understand this stuff.” Sam speaks with the same, level tone that he always uses when he’s trying to talk Dean down from an outburst. “He doesn’t understand that it doesn’t mean anything to you.”

“What if it does mean something to me, Sam?” Dean cries, throwing his hands down. “What if I’ve been in love with Cas from the beginning and I just don’t know how to explain it or even put it into words? We lose everything. Everyone. We’re black holes for this kind of stuff. To even allow myself to think that I could have that? I’m not stupid. I know how it always ends.”

“You’re in love with Cas?” Sam says, a small smile crossing his face.

“Obviously.” Dean rolls his eyes before his breath catches in his chest. He’d never said it out loud before. Oh. 

Oh, God.

“Dean, that’s…” Sam grins ear to ear as he approaches Dean. “That’s amazing!” 

“No, Sam, it’s not.” Dean stands up, dodging Sam’s attempt to clap him on the shoulder. “It’s not a good thing at all.”

“What do you mean?” Sam’s face falls. “This is what you’ve always wanted, Dean! This is your chance to lead a normal life, to get the family and the love that-”

“Like I said, Sam.” Dean says coldly. “We don’t get this. We don’t get love. We don’t get families. Look at any hunter who’s ever had a family. Rufus. Jodi. Bobby. Dad.”

“That doesn’t matter, Dean, they weren’t-”

“I can’t lose him, Sam.” Dean’s voice breaks as he looks up at Sam. 

“Dean-”

“I can’t lose him again. I’ve lost him so many times already.” Dean’s eyes are misty and a weight fills Sam’s chest. With Cas human now, the stakes are so much higher. It makes the possibility of losing Castiel so much more plausible. Sam understands Dean's hesitation.

“Look, if… if me leaving Cas alone means that he won’t die some horrible, gruesome death, then that’s what I’ll have to do.” Dean sighs, swiping angrily at his eyes and standing up.

“That didn’t look like ‘leaving him alone’.” Sam points out, following Dean as he walks through the bunker. “Where are you going?”

“For a drive.” Dean says. “I need to clear my head.” He gets to the door before he looks back, staring at Sam.

“Do me a favor, Sam. Tell Cas that he won. He’ll know what it means.” 

And with that, Dean is gone through the door, once again running from his problems with only his car radio and a trunk full of guns to solve them.