Attempt #3

Sam

"Cas, what the Hell?!"

Sam woke to find Dean trapped under a sleeping Cas, who was peacefully laying on Dean's lap. Sam let out a small 'aww', earning a death glare from his older brother.

"Come on, Dean, just leave him alone," Sam said, "he's probably tired from switching genders,"

Dean frowned and looked down at the slumbering Angel. He sighed and nodded his head, oblivious to Sam's look of realization.

If I manage to keep Cas asleep, maybe Dean will realize how cute he looks.

Sam excused himself, saying he had to go for a walk. He went outside and walked around the motel, stopping behind it. He sighed and looked around. "Hey Gabe, I need your help,"

Gabriel appeared in front of him, a smug smile on his face. "This is war, Sammy. You don't ask your opponent for help,"

Sam rolled his eyes. "Okay, first of all, this is nowhere close to war," Sam said, "secondly, I want to make a deal with you,"

"A deal? Deals are for demons, Sam," Gabe chuckled, "but I suppose I'll hear you out..."

Sam proposed his deal. A sleeping Cas for all the candy Gabe wanted. It was almost scary how fast Gabriel had agreed to these terms. He snapped his fingers, and they were instantly in a candy store.

"Did you do it?" Sam asked a distracted Gabe.

"Yeah, yeah of course,"

"Go nuts then,"

Gabriel grinned and grabbed at least one of everything in the store. He had at least four baskets full of candy. It was safe to say he and Sam had officially become their favourite costumers. When they walked out of the door, Gabriel giddily hanging on to his very large plastic bag filled with candy, they were back at the motel. Gabriel smiled and handed Sam a heart-shaped lollipop before disappearing.

When Sam got back to the room, he was surprised to find Dean staring down at Cas with a soft expression on his face. He cleared his throat to announce his presence, causing Dean to jump and Cas to groan in his sleep. Dean glared at Sam. "You almost woke him up," he whispered harshly.

"Sorry," Sam whispered back. He quietly sat on the edge of his bed and got out his laptop, pretending that he wasn't watching how Dean reacted with Cas. Sam couldn't help but smile, for whenever Dean tried to move, Cas would whine and grumble in his sleep. Dean wouldn't freak out or anything. He would simply move back to the position he was in and murmur something to the Angel in reassurance.

"He looks really peaceful, doesn't he?" Sam asked quietly.

Dean didn't reply. He merely grunted as if he didn't know what Sam was talking about. But Sam caught a small smile on his face. A tender glance down at the Angel. Sam shook his head. His brother was so smitten. It was a shame he hadn't realized it yet. It was also a shame that Sam knew he wouldn't be the one to help him realize it. He was pretty much losing this challenge. He had help from Gabriel on two different occasions. The Arch-Angel was going to win. Sam sighed. It wasn't like it was a bad thing. He really wanted Dean and Castiel to be together, and to be completely honest, he didn't think having to kiss Gabriel was that bad.

"Alright Cas, I gotta move you for a bit,"

Sam was pulled out of his thoughts when he heard Dean softly speak to the Angel on his lap. Sam smiled as Dean gently moved Cas and got up. After gently putting Cas back down on the sofa, he went into the bathroom and shut the door. Everything seemed perfectly fine until Cas started talking in a different language. Sam tilted his head. It must be Enochian. That's when things seemed...off. There was suddenly a kitten in the middle of the room. It meowed and padded over to Sam, looking up at him expectantly. Curious, Sam picked it up and put it on his lap.

Cas said something else, and suddenly, there was a large, fuzzy bumblebee flying around the room. Sam looked at it wearily, not trusting it. He glanced over at the door. "Dean!" He yelled.

Dean opened the door and instantly shut it again at the sight of the large bee. "What the hell is going on, Sam?!" He yelled from behind the door.

Castiel spoke again, making a fuzzy baby bunny appear. It looked at Sam and wriggled it's nose. Sam looked back at the door. "It's Castiel. He seems to be...er...sleep-creating...?"

"What the hell is that supposed to mean?"

"It means, he's creating cute creatures while he's sleeping," Sam glanced at the bee again, who was moving towards the window. "Well, at least things he thinks are cute,"

"What do we do?" Dean asked, cracking the door open.

"I don't know," Sam said. He thought about it. Maybe if Dean sat with him again? "Dean, go sit with his head on your lap again,"

"What, wh-"

"Just do it!"

Grumbling, Dean quietly walked over and gently lifted Cas. He took his earlier position. Cas's head resting comfortably on his lap and Dean's hand at his hair. Much to their relief, the creations had stopped. Sam opened the window to let the bee out. He looked over helplessly at the bunny and the cat. What were they going to do with them?

He decided he would have to give Gabriel another call.

Sighing, he stood and left the room again, the kitten in his arms. It seemed to grow on him, and knowing Cas, he would want to keep the kitten too. He stood outside of the motel and looked up at the sky. "Gabe. Get your ass over here,"

"Ooo, someone's a little feisty!"

Sam gave Gabriel the best glare he could muster, causing the Angel to take a step backwards. "W-what's up, Sammy-o?"

"You know what's up," Sam replied, rolling his eyes. "Wake Cas up. This is going nowhere,"

"I'm making him show you things in his dreams," Gabriel said, "sooner or later, he's going to dream up a Dean,"

"I don't care, Gabe," Sam said, "just wake him up and get rid of his large bumblebee and that adorable bunny,"

"What about the c-"

"We're keeping the cat!"

Gabriel held his hands up in defense. "Okay, okay," he snapped his fingers and disappeared. Sam sighed in relief and looked down at the kitten, who meowed up at him. When Sam returned to the room, he was beyond relieved to find the bunny gone. Castiel however, was still asleep. Or wait...

Sam squinted in amusement. Castiel was obviously faking his slumbering state at the moment. Sam was surprised Dean hadn't noticed, but then again, his older brother was too caught up in playing with Cas's hair. Sam chuckled, going back over to the bed. He put the kitten back down and smiled as it walked over and meowed at Dean.

Suddenly, Castiel was sitting upright and gasping.

"Cas?" Dean asked, panic in his voice. "What's..." He stopped speaking when Cas picked up the kitten and put it in his lap.

"It's so adorable, Dean! Don't you think?" Cas asked, holding up the kitten and looking at Dean with wide eyes.

Sam could tell Dean didn't care to much for the cat, so he coughed and sent Dean a look that said just agree with him!

"Er...y-yeah, Cas. He's a cutie," Dean agreed, practically melting at the sight of Castiel's bright, happy smile.

Sam shook his head. He hoped this contest was over soon. As much as he hated to admit it, Sam would actually enjoy it if they acted all lovey-dovey towards each other. He just wondered what Gabriel had planned next, and hoped that it would be enough to win.

Gabriel

After helping Sam out, Gabriel really had to think of a good, solid plan. A plan that no one would see coming. A plan so great, he would win this contest and finally get to make ou - er - kiss Sam.

Unfortunately, Gabriel didn't have such a plan.

So, the trickster decided whatever he thought up first would be his grand plan. Aha! A musical! Only, Dean was the only one in it. Dean would be the only one to burst into songs that represented his feelings. It would be a pretty depressing musical, but it would also be fun.

Stuffing a chocolate bar in his mouth, Gabriel clapped his hands and disappeared, reappearing in the motel the Winchesters were staying at. The first thing he noticed was that Cas and Sam were gone. He frowned and cocked his ear, hearing voices down the hall outside of the room. When he appeared in the hallway, he saw Cas and Sam talking.

"I know what you and Gabriel are doing, and I'm grateful for your help," Castiel said.

"Aww, thanks kiddo!" Gabriel ruffled Castiel's hair, earning a punch in the face.

"Sorry, it's a reflex," Cas apologized to his brother, who was rubbing his face with a sour expression.

"What are you doing here, Gabe?" Sam asked, sending him bitchface #467.

Gabriel smiled. "Conducting my next plan," he said. He turned to Cas. "You just have to make sure you're with him at all times. He's going to express his feelings with song, so eventually he'll sing a song about you!"

Castiel looked extremely confused, but he seemed to agree anyway. "I will see what I can do,"

"Excellent! Have fun!" With that, Gabriel turned himself invisible again and went to go check on Dean.

Perfect. He was already singing a song about beer.

This was going to be fun.

It was strange. Very strange. Dean had just got up to get a beer, when all of a sudden he was singing about why he drinks beer.

Dean Winchester does not sing.

He kept telling himself that, but every time he did another line of song would leave him.

Suddenly, just as his beer song had ended, Sam and Cas entered the room. "Oh thank god!" Dean exclaimed. "You need to help me! I've turned into a walking musical number here!"

Sam and Cas exchanged glances before starting to laugh at him.

"This isn't funny!" Dean yelled.

"Sorry man, but you singing in general is hilarious," Sam chuckled.

"Do you think I chose this?" Dean started singing again. He clapped a hand over his mouth to try to stop it, but Dean and Cas could still hear what he was singing. Something about how he didn't choose to sing, which then turned into how he didn't choose this life. It was like a Disney song, only more depressing...and...wait, did he hear musical accompaniment?

Sam burst out laughing as depressing piano played from an unknown source. Even Castiel smiled in amusement, but he tried to restrain it. The music changed as he looked at Cas. A ballad-like guitar strummed in the background. Castiel squinted at him, that small, amused smile seeming to widen.

"Oh come, on!" Dean exclaimed, looking up at the ceiling. He looked back down and at Cas. He clenched his jaw, trying to stop the next song, but he couldn't. For some reason he felt compelled to sing.

"When I look at you, I feel a little blue, because you don't know what I do,"

Castiel's brilliant blue eyes widened considerably. He had confusion with a hint of nervousness in his gaze.

"You see, I don't like to talk about my feelings, but I know I should at least tell you,"

Sam gasped and held his hand over his mouth. This was it. This was a confession of undying love.

"You're the best Angel I have ever met. You're the best friend I have ever had. I know it sounds cheesy, but it's true. We're the best of friends, me and you,"

Castiel looked as disappointed as Sam felt, but the Angel managed a tight smile and a soft thank you. Sam sighed almost sadly and tuned out the rest of Dean's song. He kept glancing at Castiel, making sure the Angel was okay. Sam felt bad for the Angel. He must've thought the same thing Sam had. To find out Dean only thought of them as 'best friends' must have been a pretty hard blow.

When Dean was done, he made them all swear never to mention anything about this ever again. Sam huffed and stood. "I'm going to go salt and burn this ghost's bones. It's almost dark,"

"I'll go as well," Castiel said awkwardly, "Dean, I'm sorry but you should stay here. I don't think the ghost would appreciate your singing,"

Dean huffed and sat down on the bed, grudgingly agreeing. Before Sam could even open the door, they disappeared from the room, leaving Dean alone to sing to himself.

Castiel distracted the spirit while Sam salted its bones and poured gasoline on it. In mere seconds, the ghost was gone, burned up and evaporated. Cas helped Sam refill the grave when the fire died, talking to him the whole time.

"Why did Dean only say that I was his friend?" Castiel asked when the grave was filled. "I already know that we are friends,"

"I don't know Cas," Sam replied honestly.

"I don't understand," Cas said, flying them to their hallway of the motel. "Are you certain he feels the same w-"

Sam waited for him to go on, but when he looked ahead, he knew why Cas had stopped. Dean was standing in the doorway, clearly flirting with a short blonde girl. He brushed a stray hair out of her face and laughed with her over something. Sam looked over at Cas, wincing. "You okay?" he asked softly.

Castiel's eyes were filled with tears. "I have to go," his voice wavered, and before Sam could stop him, he had swiftly walked passed the girl Dean was flirting with, gently grazed her temple with his index finger, and disappeared. The girl fainted and Dean caught her before she hit the ground. She was awake a few moments after that, and accused Dean of trying to kidnap her.

Dean grumbled in annoyance when the two brothers were finally in the room together. "I was about to get laid tonight, Sammy!"

"I don't really care, Dean," Sam glared at him.

"What's up with you?" Dean asked, "and what was up with Cas? He just...disappeared..."

"He wanted some time alone," Sam replied tensely, "or rather, time away from you. Goodnight,"

Dean felt hurt. Why would Cas want time away from him? He shook his head and decided to head to bed himself.

But for some reason, there was a burning sensation of guilt in his chest. "What did I do, Cas?" he asked.

Dean expected the Angel to appear at his bed and tell him what troubled him. But there was nothing. Dean sighed and turned, falling asleep a few moments later.

Little did he know, a very angry Gabriel was watching him, a red eyed Castiel wrapped up in his golden wings.

I'm really sorry I turned it from fun to feelsy _;