"NO WAY." Dean said, not believing this. Castiel shrugged.

"It's true." He insisted.

"You've NEVER had a sleepover?"

"Not with a boy, no."

".....Wait, you've have sleepovers with girls?"

"Oh yeah. Charlie's slept over dozens of times, and now she just lives with us." Dean blinked.

"Dude, I was never allowed to have sleepovers with girls." Cas frowned.

"Really? Why?"

"My mom always thought we'd end up kissing or something. Did your dad never think of that?" Cas thought for a moment.

"I'm pretty sure he got it confirmed that I was gay at age four, so no, I don't think he ever considered that possibility."

"Your dad is awesome."

"I know." Castiel nodded. "And you're totally sleeping over."

"Hell yeah."

*****

"IF CASSIE GETS A WINCHESTER SLEEPOVER THEN I GET A WINCHESTER SLEEPOVER!" Gabriel announced. 

"No," Chuck offered.

"What? WHY!" Gabriel demanded.

"Because I trust Cassie to behave, and you cannot be trusted to do that." Chuck declared.

"I'll behave!"

"Bitch please," Luci commented. "You don't behave when it's just us, let alone when we have guests over."

"Pleaaaaaseeeee?" Gabriel begged. "I promise we'll be good!" Chuck studied him for a moment.

".....One night." He relented and Gabriel cheered.

******

So Sam and Dean Winchester came over for a sleepover. The boys split off, Gabriel and Sam controlling the living room while Dean and Castiel took over Cas's room, leaving the rest of the siblings to fend for themselves.

And seeing as they weren't using the TV, Anna decided to try and catch up on her shows while Sam and Gabe hung out.

Big mistake.

"Hey Sam?" Gabriel questioned. "Am I in your friend zone?"

"No," Sam offered.

"Are you sure, because despite my best efforts, we haven't boned yet."

"I'm sure." Sam said. "You see, in order to be in my friend zone, I would first have to consider you my friend."

"Ouch."

"Yep."

"Wow," Anna commented, glancing at them. "And here I thought Gabriel WASN'T a virgin."

"Says the whore," Gabe declared. 

"Balthazar's the whore, remember?"

"No, Balthazar is a classy slut who breeds with the mouth of a goat. YOU SIR, are a WHORE."

"I'm not a sir."

"Just an expression."

"Does Balthazar ever get offended that you call him a slut?" Sam asked.

"The human told us he identifies as a whore," Gabriel insisted. "I don't think he minds."

*****

"What do we do now?" Cas asked, as he and Dean lounged on Cas's bed.

"We could play Never Have I Ever." Dean suggested.

"Okay."

"Never have I ever..... had a sister."

"Oh come on. Never Have I Ever moved."

"Ugh. Never have I ever stabbed someone."

"Then we're equal there, unlike some of my siblings. Never have I ever bought a playboy magazine."

"Damn you bi thoughts. Never Have I ever read all the Harry Potter books."

"How have you lived? Never Have I ever been in a police station." Dean dropped one.

"Never Have I Ever-"

"Woah, woah, back up. What were you in a police station for?"

"Um," Dean squirmed. "It's a long story and I'd rather not get into it if that's okay."

"Okaaaay," Cas looked at him curiously, but didn't press.

"Never Have I Ever been arrested."

"Well that's comforting. Never Have I ever been kissed."

"Wait what?" Dean raised his eyebrows. "Are you serious?"

"Yeah," Cas shrugged. "Never been kissed."

"Like, NEVER?"

"Nope."

"Not even the awkward second grade kiss on the playground?"

"Nada."

"HOW?" Cas shrugged again.

"I dunno. Just never happened."

"But you're so hot," Dean whispered.

"What?"

"Nothing." Dean stared at him for a moment. "I just- I can't let that slide!" Cas raised an eyebrow.

"So I can't pry into why you were at a police station, but you get to pry into why I've never been kissed?"

"It's not that I want to pry," Dean began. "I just... kinda feel like I should fix that."

"Fix it."

"Yeah,"

"How are you gonna fix it?"

"I could kiss you." Cas froze, his face slowly going red.

"Well. That. I- well- I, uh- that-" Cas stammered, not really having a proper response to that one. Of course he would want Dean to kiss him. Why the hell wouldn't he? Dean was amazing, and also completely hot. What more did he need? 

Dean half smiled at him and leaned toward him. Cas jumped back, unsure and thrown way off guard.

"What are you doing?" He asked warily. Dean smirked.

"Just trust me," Dean insisted. 

"Okay," Cas didn't move away this time as Dean got closer, studying his face. Cas half thought that his heart might just jump right out of his chest and punch Dean right then and there, but that didn't happen.

Instead, Dean cupped Cas's face in his hands, leaned in, and kissed him, shutting his eyes as he did so.

Cas melted into the kiss, inhaling sharply as he shut his eyes. It was a completely different feeling than what he had expected, but it was nice. Amazing, really. Dean's lips tasted like cherry pie and coca-cola, and for some reason, Cas didn't ever want to stop kissing him.

But Dean pulled away eventually, removing his lips and his hands from Cas's face. Cas's eyes flew open, only to see Dean watching him with a goofy grin plastered on his face.

"There," He commented. "Now you can't say you've never been kissed." Cas nodded dumbly.

"That was, uh," Cas fumbled for words, his lips still buzzing. "I liked that." Dean grinned wider.

"Most people do,"

"....We should do that again."

"Subtle, Cas."

"Would you prefer this?" Cas leaned in, quickly kissing Dean. Dean kissed him back, and the pair proceeded to make out on Cas's bed.

Or, they made out until the door burst open and someone let out a scream.

"OH MY GOD, PEOPLE," Balthazar declared. "WE HAVE ONE RULE!" Cas and Dean jumped back. Castiel knew he should be a little regretful that he'd been caught, but he didn't even feel the slightest shame. Dean was a great kisser.

"Sorry Balthazar," He mumbled, blushing.

"ONE RULE," Balthazar repeated. "WHAT IS THE RULE, CASSIE. MY ONLY RULE."

"Don't fuck in the house," Cas muttered.

"DON'T FUCK IN THE HOUSE!" 

"We weren't going to-"

"Bullshit! I know where that was going!" Balthazar whipped towards Dean. "And if you force my little brother to do anything he's not comfortable with,"

"OKAY BALTHAZAR, TIME TO LEAVE!" Cas bellowed, shoving his sibling out of the room and slamming the door.

"Oi! I still need my jacket, you gay fucks!"

"He's a wonderful sibling, isn't he?" Dean commented, as Cas located Balthazar's jacket, threw it in the hallway and slammed the door again.

"Just wonderful," Cas grimaced.

*****

After dinner Chuck receded into his room in an attempt to get some work done, which meant that the Winchesters were abandoned to the whims of the Novak kids, who had promptly raided the entire house for snacks and circled up in the living room, wordlessly passing bags of candy and popcorn back and forth.

"We should do something," Gabriel suggested. 

"Like what?" Hannah asked. "Braid each other's hair?"

"Only if I get to braid Sam's."

"Hey!" Sam said. "My hair is not THAT long-"

"Yes it is," Dean agreed.

"Is not!"

"There's a reason he calls you Sampunzel, but if you just give me five minutes with the clippers-"

"You're not cutting my hair, Dean."

"Oooohhhh, is it hair salon time?" Balthazar asked, ready to go raid the bathroom for Anna's hair products.

"NO." The rest of the Novaks said at once. They all remembered what had happened last time Balthazar and Hannah had played hair stylist. Anna had worn a wig for a month and Michael still had the scars.

"We could play Truth or Dare unless you guys are chicken." Lucifer suggested. Dean grinned.

"Bring it on." He said.

"Fine, Winchester. Truth or Dare?"

"Dare."

"I dare you to order me a pizza." Dean gasped.

"I HAVE BEEN BLIND TO THE POSSIBILITIES."

"That's what I'm here for. Learn from me." Lucifer said.

"Oh no no no," Cas insisted. "My Winchester is not gonna become your apprentice."

"Of course not, Cassie, Gabe's already my apprentice."

"And I learn well from my master," Gabriel said ominously, bowing.

A few hours into Truth or Dare later, things had kicked up a new notches, as expected.

"Dare." Michael said.

"Alright," Hannah began deviously. "I dare you to call Lucifer's girlfriend and confess your undying love for her." They all gasped.

"You're evil," Michael said. "And she'd never believe it."

"Then it should be easy to do." Michael glanced over at Satan, awaiting approval. Lucifer thought for a moment and then nodded.

"Do it," He said. "But put it on speaker, I'm curious what her reaction will be." 

So Michael called Chloe and put her on speaker and the rest of the group waited in silence.

"Hello?" Chloe's voice rang out through the room.

"Hello Chloe," Michael started.

"Michael, do you have any idea what time it is?"

"Uh....Past 11?"

"Yes, so this better be important."

"It is."

"Is Luci okay?" Lucifer grinned smugly and Hannah clamped a hand over her mouth to prevent a fangirl screech.

"He's fine, I actually just wanted to talk to you. I have to tell you something very important," Michael said seriously.

"What is it?"

"Chloe..." He sighed dramatically and made a pained expression that had everyone struggling not to laugh. "I know you're with Lucifer, you always have been, and I'm sure you love him dearly, but- I love you too, Chloe. I always have." 

Dead silence greeted him, and they all stared at the phone intently.

"Uh...." Chloe started. "Well...then....This is....awkward..."

"It doesn't have to be, my love," Michael continued, and Balthazar let out a tiny squeak and covered his mouth with his hands as the others glared at him.

"Michael....how do I put this....Well I mean for starters, I thought you were gay-" Anna got up and left the house, unable to contain herself any longer.

"No," Michael insisted. "Nope. Not gay."

"And more importantly, I'm with Lucifer. I love him."

"But doesn't that get old after awhile?" Michael asked. "I mean you've been with him FOREVER. Surely you must be sick of the Satan jokes by now. I mean, he's my twin and even I get tired of him sometimes. He can just be so annoying, but I would never be like that to y-"

"Okay, I'm gonna stop you right there, cause FIRST OF ALL, don't you DARE insult my boyfriend, he is the King of Hell and that makes me his queen and I'm damn proud of that. I will never get sick of those jokes because if he thinks he's Satan, then that makes me Queen of Hell and he treats me like it, so don't say you could be better than him cause you can't. Nobody's a better boyfriend than my Luci. And he's annoying in a cute way AND he's hotter than you, so sorry Michael, but whatever little crush on me you have, you should kill, cause I'm NEVER gonna leave your brother for you, sorry buddy." Chloe hung up the phone and they all started at it for a moment.

And then they burst out laughing.

"I feel like I should be offended," Michael started.

"Damn, I love that girl," Lucifer grinned. 

"THIS IS WHY I SHIP IT," Hannah yelled, punctuating each word with a loud clap.

"Dude, you better marry her someday," Dean insisted.

"Oh believe me," Lucifer agreed. "I will."

"If she doesn't leave you for one of us," Balthazar said. "Cause like, we know that she's not into Mikey, but I'm available soooo"

"Balthazar, you even think about making a move on my girl and I'll break one of your arms."

"Just one? That seems like a light threat coming from you."

"I'll only break the one because Chloe will have already broken the rest of your limbs."

"Fair enough."

*****

Much later that night, after the rest of the house had decided to go to bed, (Well, sort of. Lucifer had gone to Chloe's, and Dean and Cas were likely still awake upstairs, but everyone else had probably gone to sleep) Sam and Gabriel lay awake on the couches in the living room.

"Gabe," Sam whispered, not wanting to disturb the silence of the house. "What time is it?"

"Hold on, I'll check," Gabriel insisted. He half dove under the couch, emerging with a recorder. He blasted into the instrument loudly until there was a crash from upstairs.

"WHO THE FUCK IS PLAYING THE RECORDER AT 2 AM?!?!!" Anna yelled.

"It's 2 am," Gabe relayed. 

An hour later, they were still awake.

"Hey Sammoose," Gabriel whispered.

"Yeah?"

"What language do they speak at the center of the earth?"

"Gabe, it's like 3 in the morning."

"Core-ean."

"If there is a god, please help me."

"My dad's god," As if on cue, Chuck trudged into the room. 

"Who dares call upon my name?" He asked.

"I'm deeply concerned right now," Sam retorted.

"Don't question the ways of the Novak house, Sammich," Gabriel advised.

An hour later....

"Sam?"

"There's no such thing as sleep in this house, is there?"

"Nope. Besides, we have something much more important to talk about."

"And what's that."

"You should be my boyfriend."

"....Why the HELL would I be your boyfriend?"

"Okay, A) Don't say the H-E-double hockey sticks word at this hour or you'll disturb Satan. B) I am probably the greatest boyfriend in the world,"

"I beg to differ, I've seen a lot of TV. There's better boyfriends than you." 

"Like WHO?"

"I dunno. Joey Tribbiani sounds pretty good right now."

"So you'll date JOEY FROM FRIENDS, but not ME?"

"I see no reason to date you! You've never even asked me out!"

"Yes I have! Several times! You're just oblivious!"

"Whatever."

"Okay, look. The benefits of dating me would be just that. You'd be dating ME."

"And?"

"And I could go on, but I think I've made my point."

"....Wow."

"Is that a yes?"

"NO."

"Is it a No?"

"....." Gabriel grinned at Sam's silence. No news was good news, after all.

"Mischief Managed."

"You're not a Marauder, what the fuck did you do now?"

"You'll understand when we're married."

"My GOD, you're narcissistic."

"I don't know what that means, so I'm just going to take it as a compliment."

"You're two years older than me. How do you NOT know what narcissistic means?"

"Buddy, if it ain't in a comic book, I ain't gonna read it and figure out what it means."

"See this is why I can't be your boyfriend."

"Why? Because I don't know what narcissistic means? I CAN LEARN, SAMUEL, I SWEAR!"

"No, because we're completely different people, Gabriel. It would never work." Gabe flopped over to stare at him.

"If it would never work, then there's no harm in trying, right?" Sam blinked.

"Well....I guess..."

"Exactly. And besides, you'd be dating a Junior as a Freshman. That's gonna give you major points forever. I'd only be helping you."

"If you say so,"

"Oh, I do say so."

"Fine."

"Fine what?"

"FINE, I'll be your boyfriend." Gabe grinned cheekily.

"Now was that so hard?"