Supernatural fic: School's Out (Dean/Cas NC-17 AU)

[the_diggler]

Title: School's Out
Rating: NC-17
Pairing/Characters: Dean/Castiel, mentions of Dean/Lisa, Dean/Anna, some Castiel/Meg, and the orgy harem ;)
Genre: AU, first!time (bottom!Cas) sex with lots of angst, some humor, and a dash of fluff.
Spoilers/Warnings: underage alcohol and drug use, AU references to all seasons I guess, and it may be a little OOC but I like romantic!Dean dammit. Also unbeta'd. I could work on it more but I'm sick of looking at it lol.
Word Count: around 7,735.
Summary: It's Grad Night, and Dean wants Cas to have some fun before his best friend goes away to college. But watching Castiel on a mission to lose his virginity is harder on Dean than he ever thought it would be.
Author’s Notes: So here’s the sequel to High School Hero, but it’s not really necessary to read that fic before this one. I haven’t written NC-17 in a long time, and it’s my first for Dean/Cas, so maybe that’s why it’s so long and why I struggled with it so much! So I just want to say thanks to my cheerleaders on this, especially head cheerleader luvsbitca, you’ve all been so supportive! Also want to mention Gedry here, whose beautiful fics I discovered just when I was writing this and helped me channel all this angst <3
Disclaimer: Supernatural ain’t mine. And there's a reference to the movie Almost Famous in here that I just couldn't resist putting in XD



~

Dean Winchester was a total loser. He knew that now, standing in the middle of a raging house party with no one to talk to, and where even the girls wouldn’t give him the time of day. Or night. Whatever. He supposed it was inevitable… Ever since Castiel Novak had shown up on the first day of Senior year.

He’d let all his past acquaintances slide when Cas came into his life, the other boy leaving such an impression on Dean the first day of school, that he’d gone out of his way to make sure he’d spent as much time with Cas over the next year as possible. Even though Cas was unusually serious and freakishly smart, and therefore almost the complete opposite to him in a lot of ways, Dean found himself enjoying Castiel’s company in a way he’d never experienced with any other of his peers before.

Castiel had been the friend to Dean that he never knew he’d wanted. From day one, Cas had been attentive and supportive of everything Dean said or did, while still managing to call Dean on his crap. Cas never got offended when Dean teased him or called him a nerd, and more than once he had come to Dean’s aid when Dean got himself into trouble. When the football captain had swung at Dean for messing around with his girlfriend, Cas had cracked the guy on the jaw before Dean even got a returning swing in. When Dean got detention for being caught in the janitor’s closet doing some heavy, bendy petting with Lisa Braeden, Cas had looked after Dean’s little brother Sam in the library afterschool everyday, so they could all still drive home together. Cas had even patiently helped Dean study for the classes he’d struggled with, which was pretty much all of them, until eventually there wasn’t a weekend that went by without them sleeping over at one or the other’s house.

And where was his best and only friend now? Off somewhere on the Cas-finally-loses-his-virginity mission.

“Dean, why are you so insistent that I come to this party?” Cas had asked earlier that night.

“Dude. It’s Grad night. High School is officially over! What better reason to celebrate? And we are SO getting you laid,” Dean had replied. “And don’t give me that ‘never had the occasion’ crap, what better occasion than tonight?”

Castiel had blushed and sputtered, denying any remote chance of that occurring, but as soon as they’d stepped through the door to Crowley’s house, Meg Masters had stumbled up to them with a drunken swagger

“Dean!” she’d exclaimed, beer spilling out of the plastic cup in her hand. “And Caaasss!” she’d slurred upon seeing him, her eyes alighting with a leer. And then she’d trudged right up to Castiel, and planted her lips on his mouth.

Dean’s eyes had gone wide in shock. For a second he’d believed that getting Cas laid was going to be easier than he thought.

Then when Meg finally pulled away, Castiel had simply blinked at her for a second, before pushing her against the opposite wall of the hall, and going for it.

A lurching feeling had risen up in Dean’s stomach at that, and he’d suddenly realised it wasn’t going to be easy at all.

“Enjoy,” he’d muttered, before stalking off to find the beer.

~

If anyone had asked Dean when he’d fallen for his best friend, he would have said it was the first day they met. But that wouldn’t have been the whole story. Sure, Dean had been instantly drawn to Castiel, the other boy having an unsettling effect on him that could have easily been labelled as attraction. But the pieces didn’t really click into place until months later.

He was having sex with Anna Milton in the backseat of his car, when she’d looked at him with her big doe-eyes and tilted her head in a way so similar to Castiel, that everything had suddenly felt so completely wrong. He’d tried to ignore it at first, but everytime he looked at her after that all he could see was Cas’ blue eyes in his head, and when he came he’d had to bite his lip so hard against crying out Cas’ name that it bled.

He’d tried a few times again after that, with a few other girls, but every time the result was the same. He wanted Castiel. And every time it got harder and harder to fake his way through each encounter. So eventually he just gave it up. And even though his reputation was still fodder for cafeteria gossip, the girls had pretty much gotten the picture and left him alone.

In a way, Dean was grateful, because that meant he could spend more time with Cas.

Dean never did anything about it, though. Castiel had never given Dean any indication that he might feel the same way, let alone be attracted to guys, and even though Dean knew they would go their separate ways at the end of the year anyway, he didn’t want to lose his best friend just yet. He needed Cas too much. He wouldn’t have graduated without Cas’ help. Hell, he might not have even showed up to school in the first place. But Cas’ company gave him something to look forward to every day. And he couldn’t lose that. So instead, he decided he could put his own desires on the backburner, in favor of being as good a friend to Cas as Castiel had been to him.

Hence, the mission. He hadn’t really thought through what he’d been saying at the time, hadn’t really thought about how it would affect him if Cas really did find some girl to go and finally make merry with. He’d just gotten so used to playing the role of best friend that the words had just come out of his mouth, wanting Castiel to have the fun he deserved.

And he had no right to be standing here regretting it. Castiel was going off to college across the country soon, while Dean was going to stay home and start working at his Uncle Bobby’s garage. So yeah, sooner or later, Cas was going to find a girl, maybe eventually one to settle down with… and Dean would just have to try to be happy for his friend from a distance.

~

Dean scrubbed a hand over his face as he stepped outside onto the back-lawn, desperately in need of some air. But when his bleary eyes focused, he froze in surprise.

Cas was right there, sitting outside on the grass

Surrounded by a circle of girls.

As Dean walked up to the small group, he could hear his friend spouting poetry or philosophy or something, and by the looks on the girls faces, they were just eating it up.

For a second Dean wondered if that’s how he looked when Castiel occasionally read out some passage or poem while helping him with Mr. Alastair’s English Lit class. Those moments were the only time the subject hadn’t felt like absolute torture to Dean, and he’d eventually found subtle ways to get Castiel to read things to him more often during their many study sessions, unable to get enough of the sound of Cas’ still deepening voice rumbling over the words.

Castiel looked up as Dean approached, and gave Dean an unusually wide smile.

“Excuse me, ladies. I think I need to confer with my friend for a minute,” Cas murmured, throwing a playful wink Dean’s way. Dean reeled in midstep at that, surprise fluttering in his chest, but he quickly chalked it up to whatever Cas must’ve been drinking and shook it off.

“Hey,” Dean frowned in confusion, “What happened to Meg?”

Castiel laughed. “She passed out on me, Dean,” he replied, his face crinkling up in amusement and his hand going to his mouth as he tried to hold down snickers.

Dean’s brows furrowed as he took in the puffy look around Castiel’s eyes.

“What… are you stoned?” Dean exclaimed.

“Well, I wasn’t sure if it was doing anything, but now… I think I’m starting to feel something,” Castiel replied thoughtfully.

“Huh,” Dean huffed out, unsure whether to be worried or amused.

Cas’ reddened eyes lolled back to the group of girls.

“Okay, well, I guess I’ll just let you get back to it then,” Dean muttered, turning away.

“Dean, join us,” Castiel said, placing a hand on Dean’s arm and stopping him. Dean looked down at Cas’ hand, feeling the warmth of it through his jacket, then glanced over at the circle of waiting girls. With a sigh, he pulled away. He did not want to watch this.

“Thanks, Cas, but I’m working on something inside,” he said, plastering a suggestive grin on his face and hoping Cas would believe the lie. Castiel frowned a little, but he nodded, turning to head back to the girls, and taking a deep, steadying breath, Dean headed back inside.

Half an hour later though, Dean found himself keeping an eye on Cas anyway, throwing glances out the window every few seconds as he drowned himself in his beer.

~

Dean splashed water over his face and sighed, staring at his miserable reflection in the mirror and ignoring the banging on the door from the couple outside who wanted to “use” the bathroom. He’d officially had enough of this party. He’d had enough beer to take down a Football player and he wasn’t even tipsy, he was sick of Becky Rosen trying to corner him every five minutes trying to get him to sign her yearbook, and the sight of his classmates having a good time and hooking up everywhere was grating his nerves in ways he couldn’t deal with anymore. The only time he’d almost smiled for real was when he caught sight of Bela Talbot discretely pocketing some of Crowley’s silver. But yeah, that was a big almost.

He resolved to check up on Cas one last time, and then he was leaving. Mission or not, Cas seemed to be having a pretty good time anyway, and that was the best Dean could’ve hoped for.

But Castiel was nowhere to be found. Not outside, or inside, and Dean had just begun to get a sinking feeling that Cas had finally scored… when he saw everyone outside starting to look up, pointing at something at the sky. With a feeling of dread in his gut Dean pushed his way outside, looking up at what had everyone’s attention… and there was Cas, standing on the edge of the roof, his arms stretched out wide and his trenchcoat flapping in the air like wings.

“I AM A GOLDEN GOD!” Cas shouted out into the night sky.

Dean cursed as everyone broke into cheers around him, and he immediately started pushing his way through the crowd to the trellis on the side of the house. As he climbed up to the roof he could only pray Cas didn’t do something stupid like jump off into the swimming pool or something… but when he finally got to the top Cas was still there, teetering on the brink.

Just as Castiel lost his balance and lurched over the edge, Dean got to him, pulling him back in the nick of time and wrapping his arms around him.

“Dean! How did you get here?” Castiel blinked owlishly as Dean held him up. Dean snorted in exasperation.

“I’m Batman,” he deadpanned.

Cas barked out a short laugh, before his face suddenly went blank. He blinked at Dean once, twice, then keeled over and started hurling all over Dean’s shoes.

Dean cringed as he held on to Castiel, looking away and breathing through his mouth in an attempt to avoid the smell... but it was unescapable.

“Have you been drinking absinthe?!”

Castiel moaned miserably.

“Come on, Cas. I’m taking you home,” Dean growled.

“But what about the mission?” Cas protested weakly.

“Dude, you’ve been off-mission for a while now.”

“That’s just how I roll,” Cas laughed. Dean sighed, guiding Castiel back to the trellis and carefully helping him climb back down the side of the house.

~

Once they finally got back to Castiel’s house, Dean made sure Cas ate something and drank plenty of water, before practically throwing him into the shower to sober up a little. When Cas eventually emerged from the bathroom he was at least walking straight again, but even though he was still more than a little tipsy he seemed more tired than anything, collapsing on his bed and tugging vainly at his blanket in an effort to cover himself. Dean snorted in fond exasperation, helping Cas pull up the sheets and tucking them around his body, before heading to the shower himself.

By the time Dean was done, Castiel was already asleep, and Dean smiled a little as he took in the sight of his sleeping friend. Cas looked so vulnerable in his bed, curled into a ball under the sheets, his normal bulky trenchcoat no longer belying his small frame, and his face relaxed into an innocence that was so unlike his normally serious countenance. Dean knew he was being kind of creepy, but he couldn’t give a damn. It wasn’t the first time he’d watched Castiel in his sleep, and he was going to miss being able to see his friend like this when Cas left.

Dean sighed wearily, sitting down on the edge of the bed as gently as he could. Cas didn’t stir, so, feeling brave, Dean risked running his hand through the mess of Castiel’s dark hair, his fingers lingering as long as they could through Cas’ unruly locks.

Castiel’s eyes began to blink open, and Dean hastily drew his hand away, flushing uncomfortably. Cas regarded him silently for a long moment, then slowly pushed himself up, backing up to lean against the headboard.

“How you doing?” Dean asked, “Feeling better?”

Castiel gave him a small nod. “Thank you for looking after me, Dean,” he said, his voice still scratchy from the earlier abuse on his throat.

Dean swallowed hard, the gravelly texture Cas’ voice had taken on, coupled with the sight of Cas sitting on his bed with the sheets pooled around him, bathed in the soft glow of the bedside lamp… it did things to Dean he’d thought he’d gotten good at suppressing by now.

Dean tore his eyes away, clenching his fists in want.

“Dean?” Castiel asked in concern, and Dean’s breath hitched in his throat as that voice assaulted him again. He took in a deep gulp of air, steadying himself.

“Look, Cas, you gotta promise me something okay?” he said, eyes trained on the floor, “You gotta be more careful when you go to college. They’re gonna party harder, drink harder, the drugs will be harder… You gotta watch yourself. Something could happen to you… and I’m not gonna be there,” he choked off.

Castiel remained silent.

“At least the women will be easier,” Dean huffed out a laugh that he hoped didn’t sound too bitter. “Judging from tonight, they’ll probably be throwing themselves at you,” he finished quietly.

“They can throw themselves at me all they want, they’ll never get anywhere,” Cas replied softly.

Dean whipped around to look at Cas at that, and his chest constricted at the sadness he saw in the other boy’s eyes.

“Don’t sell yourself short, Cas. I’m sure when the right girl comes along you’ll know what to do,” Dean said, trying to placate his friend.

“Dean…” Castiel hesitated, biting his lip. “… I’m not interested in girls.”

The air rushed out of Dean’s lungs.

“Oh,” he said stupidly.

Castiel looked down, his eyebrows furrowing together in a small movement that Dean couldn't read.

“Okay, Cas,” Dean breathed. “Then you gotta promise me to be even more careful.”

“What?” Castiel looked back up at him in confusion.

“Look, I know you’re usually more than capable of taking care of yourself. But just… don’t go get drunk or high or something and let some guy you don’t even know take advantage of you. From what I know about this stuff, you could get really hurt,” Dean explained. “Wait for someone… who you can trust to take care of you. Who will… respect you the way you deserve,” Dean finished haltingly, looking away.

Castiel was silent again for a long moment, then

“…I trust you Dean,” came the reply, so soft that Dean barely heard it in the dead silence of the room. Slowly he turned to look back at Castiel, his fists clenching again as his pulse began rushing in his ears.

“What?” Dean rasped, his voice barely a whisper.

Castiel sat up, curling his knees under him as he pushed the sheets away and leaned forward, close enough that Dean could still smell the absinthe and beer through the mint of Castiel’s toothpaste.

“Dean,” Castiel began. “I don’t want to lose my virginity to… some guy I don’t even know,” he said, repeating Dean’s words. “I know you. I trust you. And you have… experience…”

“Cas…” Dean cut him off, “Are you asking me to… take your virginity?” he huffed out in disbelief.

Castiel gave him a weak smile. “Gotta complete the mission, right?”

“You’re drunk,” Dean growled, standing up off the bed. “And probably still high.”

“Dean, I’m sorry,” Castiel stood up, rushing to his side. “I was out of line, please don’t be upset with me!” he apologized. And when Dean turned to look at his friend he nearly reeled back from the worried anguish on Cas’ face.

“It’s not that, Cas,” Dean explained as soothingly as he could. “It’s just… you probably don’t really know what you’re saying right now, and you might regret it in the morning.”

“No, Dean,” Castiel replied softly, “I’ve thought about this before tonight.”

“You’ve… thought about this?” Dean echoed, stunned.

Cas looked down at his feet, nodding his head almost imperceptibly. Dean had to take a step back, walking over to the bed to sit down, overwhelmed by the implication of Castiel’s admission. But before he could feel any hope that Castiel might actually feel the same way he did, another, more rational explanation came to him.

“Of course you’ve thought about it.” Dean huffed out a bitter laugh. “You think everything through, don’t you,” he finished flatly.

It didn’t mean anything. Dean was just… the logical solution to a problem.

Castiel shuffled towards the bed, sitting down beside him.

“Dean, if the idea of being with another guy isn’t impossible for you, then… could you please consider doing this for me?” Castiel asked softly.

And that’s when Dean’s resolve finally began to crumble.

Castiel had never asked Dean for anything. And yet Cas had done so much for Dean over the past year, Dean could barely even comprehend how much he owed him. Even though Cas didn’t understand just how much he was asking of Dean, how much it would kill Dean to finally cross that line with him, only to have to let him go afterwards… Cas had every right to ask it of him.

Dean took in a deep breath, raising his eyes towards the ceiling in frustration. “Cas, I’ve never been with a guy before. I could hurt you,” he whispered.

The sheets shifted beside him as Castiel moved closer. “I know, Dean. But it’s alright. I have no doubt in my mind that you’d do your best to… be careful with me,” Castiel murmured, breath ghosting against Dean’s neck.

“Cas--” Dean choked out in desperation.

“Dean…” Castiel replied, voice soft and pleading. And when Dean felt Castiel’s fingers hesitantly touch his shoulder, his resolve finally broke.

With an anguished groan Dean turned, crushing his lips to Castiel’s mouth as he fisted his hand into the back of the other boy’s hair. Castiel stiffened in shock, gasping in surprise, and Dean took the opportunity to push his tongue into the other boy’s open mouth, laving at Castiel’s tongue hungrily. Somewhere in the back of his mind Dean knew he should be taking it slow, easing his way into this more gently, but he still had the image of Castiel pushing Meg Masters up against a wall seared into his memory, and he desperately wanted to erase it.

And then suddenly Castiel started responding, pushing back against Dean’s lips with equal ferocity, moaning as he wrapped his arms around Dean’s neck and all but climbing into Dean’s lap.

Dean groaned again, pulling Castiel across and hugging the other boy’s lean frame more tightly against his own. His hand found the edge of Castiel’s shirt, and slipping it underneath, he slid his palm up the other boy’s spine. Cas gasped at the contact on his skin, and he arched his spine in pleasure, pressing himself into Dean’s lap with the movement.

“Cas…” Dean clenched out at the pressure against his crotch, burying his face into Castiel’s neck. Nipping and sucking needily at Cas’ throat, he trailed a wet path back to the other boy’s mouth, and Cas’ lips readily met his own again, devouring them with a moan.

It had been too long for Dean, too long since he’d been pressed against another body this way. And now that he had who he’d wanted for so long in his arms, Dean found himself hardening almost embarrassingly fast. But if it had been that long for Dean, it must have been even worse for Castiel, who had never been with anyone, and was hardening against him just as quickly.

As soon as Dean felt it, he slid his hands down to grab at Castiel’s ass, pulling him in even closer and pressing their lengths together. Groaning, Cas began to roll his hips, clutching at Dean’s shoulders as he slowly rubbed himself against Dean’s crotch.

“Shit, Cas!” Dean gasped. Castiel didn’t stop, staring back at Dean with blown pupils and breathing heavily through parted, kiss-bruised lips. Dean didn’t know where to look as his breaths raggedly chased after Castiel’s, all he knew was that he didn’t want to stop looking, and he wanted more.

Grabbing on tight, Dean flipped Cas around onto the bed, crushing his lips down again. Castiel moaned back up into Dean’s mouth, legs wrapping around Dean’s hips in response and pulling him in. Dean settled in between Castiel’s thighs all too easily, dipping his face into the other boy’s neck and pressing frantic kisses into the skin there, his hands scrambling to find the end of Cas’ shirt, in search of skin again. Castiel gasped when Dean found it, and Dean slid his hand so far up Cas’ torso that the shirt hitched all the way up the other boy’s chest.

And then Cas’ hands were scrambling at Dean’s shirt in return, tugging at it with urgency until Dean finally had to pull away, just enough to yank it off. Castiel didn’t miss a beat, taking the opportunity to lift his own shirt off the rest of the way and throw it to the floor. For the barest second they just looked at each other, breathless and wanting, and then Dean found himself diving in again, locking his lips onto Castiel’s.

As the skin of their naked chests made contact, Castiel released a loud, throaty gasp, and Dean suddenly remembered how good it was the first time he’d pressed himself against another person’s bared flesh, how utterly intimate it had felt. Only this time it was all the more sweet, as it was Cas pressed up against him, and Dean was the one to give him this first. And then Castiel’s hands began to roam, sliding up Dean’s back and exploring his shoulderblades, before travelling down his spine again, and Dean arched his back and keened, like it was the first time someone had touched him.

But Cas’ hands kept travelling, reaching down to grab Dean’s ass and pull Dean against him again. Dean gasped out loud, unable to do anything but watch Cas in amazement as the other boy once again began rocking against him.

“Dean…” Cas gritted his teeth against the groan, head dropping back against the pillow as he shut his eyes against the maddening friction. And the way Cas’ voice sounded around his name, it made Dean’s entire body shudder in response.

Sliding a shaky hand up Castiel’s chest, Dean brushed a thumb against one of the other boy’s peaked nipples, and Cas’ eyes flew open again, gasping as he pushed up into the touch. As Dean continued caressing the rosy nub with his thumb, Castiel’s hips began rubbing harder, legs wrapping around Dean’s hips even tighter. Then with a strength that always surprised Dean, Castiel flipped them over, pinning Dean beneath him as his lips crashed down upon Dean’s once more.

But before Dean even had a chance to respond, Castiel had pulled away again, pressing quick, frantic kisses all over Dean’s face and neck. Surprised and not knowing what to do, Dean’s hands hovered uncertainly around Castiel’s shoulders, until he finally settled them on Cas’ back, rubbing soothing circles into the other boy’s skin in an attempt to calm his friend’s passionate outburst. It seemed to work, Castiel finally calming down a little and slowing his pace, his lips now lingering on Dean’s skin a little longer with every kiss.

Then eventually Cas began to suck at him with every press, tongue tracing lazy circles into his skin, trailing a path downwards until it found one of his nipples. Dean gasped, arching his back as Castiel’s warm mouth sucked against the nub of flesh, his fingers weaving into the back of Castiel’s hair as the other boy bit and teased and laved with his tongue in apology.

And then Cas’ lips made a trail down Dean’s stomach, and Dean’s breathing sped up in anticipation. Castiel looked up at him in silent request as his fingers dipped into the waistband of Dean’s trackpants, and Dean nodded. And then Dean was naked, bared, glistening and aching with need.

Sliding his palms slowly up the insides of Dean’s thighs, Castiel gently spread them apart, settling himself between them. Then, tentatively, Cas brushed his fingers up Dean’s length, and Dean released a strangled gasp at the touch. Castiel’s fingers continued to trace his aroused flesh, and Dean squirmed, clenching his fists into the bedsheets and trying to be patient as he let the other boy explore.

When Cas finally flicked his tongue against the tip of Dean’s erection, Dean’s hips reared up in response. He’d never been so sensitive in his entire life. And then Cas boldly licked up his entire length, and Dean nearly sobbed, his entire body shuddering at the wet caress. Finally Cas’ hands went to Dean’s hips, holding him down, and Castiel’s mouth closed around the tip of his erection, sucking and licking at it with his tongue. Dean keened and moaned as his hips writhed in response, desperately needing more. He would’ve pushed himself right up into Cas’ mouth, but was grateful for the other boy’s hands holding him down. And then finally Cas took him in, all the way, and Dean had to shove a fist in his mouth as he cried out.

Slowly, Cas began a rhythm, up and down Dean’s cock with his lips, and it was all Dean could do to not cry out with every bob of Cas’ head. And then Cas released Dean’s hips, hands exploring the insides of Dean’s thighs and the heavy flesh in between, and Dean nearly melted into the bed. It was amazing, and Dean couldn’t tear his eyes away from the boy between his legs, unable to believe it was finally Cas doing this to him, making him feel like this was his first time, yet again.

And like his first time, all too soon Dean felt himself close to the edge. But it was too fast, and this wasn’t what he wanted, so using all the willpower he could muster, he reached down to push Cas away.

“Cas, wait!” he moaned weakly.

Cas looked up at him, confusion on his face.

“What is it, Dean?”

“Just… c’mere,” he said, sitting up and pulling Cas into his lap.

“Was that not good?” Castiel frowned worriedly.

“No! I mean, yes, Cas. It was good,” Dean rushed to assure him. “It was great,” he panted, pressing his forehead to Castiel’s.

“A little too great, if you know what I mean?” Dean huffed out a laugh.

Castiel breathed out a small laugh of his own.

Dean pulled away enough to look into Castiel’s eyes, searching their pupil blown depths as they gazed back at him patiently.

“Can we just… slow down a little?” he asked softly.

Castiel nodded, giving him a small smile. Dean returned the smile, caressing the back of his fingers down Castiel’s cheek and softly brushing his thumb brushing over Cas’ kiss-swollen lip. Pulling Castiel closer he manoeuvred the other boy down underneath him again.

This time when Dean leaned down to kiss Castiel it was soft, and slow, and he took his time learning the shape of Castiel’s lips against his, exploring the feel of the other boy’s tongue as it meshed with his own.

Castiel made pleased noises somewhere in the depths of his throat, his hands languidly roaming over Dean’s back and gently pulling Dean in a little closer. Dean couldn’t stop himself from pressing against him, slowly rubbing his arousal into the dip of Castiel’s hip as he responded with his own murmurs of pleasure. Sliding his hand downwards, he cupped Castiel’s erection against his palm, and Cas keened, clenching his eyes shut at the pressure and pushing up into Dean’s hand. Dean slowly rubbed the length through Castiel’s pants, matching the pace of his own hips, and Castiel moved with him, meeting the rhythm.

Then Dean slid his hand inside Castiel’s pants, and wrapped his fingers around the other boy’s hardness. Castiel gasped out loud at the touch on his heated flesh, and his hands gripped at Dean’s shoulders tightly. Dean began stroking, slowly, rubbing his thumb over the leaking head, and Castiel’s entire body shuddered in response.

“Dean…” Castiel whimpered, turning his face away, his eyes still squeezed shut against the sensations overwhelming him.

Dean pulled away, taking his hand out of Castiel’s pants to push them off. As he threw the pants to the floor he settled himself in between Cas’ legs, pushing them apart as his thumbs stroked the insides of Castiel’s thighs. Cas was so beautiful like this, spread out before Dean and staring back at him with such a burning ache in his big blue eyes… that Dean suddenly felt nervous. He’d never done this to another guy before. Sure he’d had a lot of experience with girls doing this to him, but this was completely different.

But then, this was Cas. And that very thought was enough for Dean to want to plant his lips all over his body. Cradling Cas’ length carefully with his hands, he closed his mouth around the tip, sucking on it gently and licking at it experimentally with his tongue. The action drew out a quiet groan from the other boy, and encouraged, Dean slid his lips down farther, taking Cas’ entire length in. Castiel hissed, hips arching up into Dean’s mouth, and Dean had to hold him down, his thumbs moving in soothing circles against Cas’ skin as he began to move his mouth slowly up and down Castiel’s cock.

Any doubts Dean might have had about this being weird flew out the window. He couldn’t get enough of Castiel whimpering and shuddering under his hands, the heavy feel of the other boy’s hardness against his lips, and the heady smell of soap and something so undeniably Cas… that Dean found himself rocking into the sheets, unbelievably aroused as well. He used every bit of experience he had, trying out all the tricks that he’d enjoyed himself, and was rewarded every time with gasps of pleasure, bucking hips, and small tightening spasms in the warm hands around his wrists.

And then Castiel let him go, one hand going into his hair and stroking through it tenderly, before those fingers softly brushed down the side of his face. Dean opened his eyes at the caress, and Cas was looking at him so intently that Dean felt a flush begin to burn up his neck that had nothing to do with how aroused he was.

“Cas?” he whispered uncertainly.

Castiel swallowed hard, then finally turned away, reaching over to open the bedside drawer, and pulling out a condom and bottle of lube.

Anxiety fluttered in Dean’s chest again. This was it.

Dean climbed up the bed, taking the lube from Cas with shaky fingers.

“Cas… you sure about this?”

“Yes!” Cas breathed before Dean had even finished speaking.

“Okay,” Dean nodded. Swallowing the lump of nervousness in his throat, Dean opened the bottle of lube, covering his fingers.

When his fingers were liberally drenched with the fluid, he settled himself on top of Castiel more comfortably, reaching down between the other boy’s legs. Castiel’s breath hitched in his throat as Dean brushed against him, and he parted his legs a little wider. Then Dean pushed in, and Castiel breathed something like a sigh of relief underneath him. Dean pushed in another finger, and when he was met with surprisingly less resistance than he expected, he had to wonder if Castiel had done this to himself before. His mind blanked out a little at that thought, overwhelmed by the mental image, and he must’ve pushed a little too hard in response because Cas suddenly let out a loud gasp beneath him. Dean cursed internally as he came back to what he was doing. The sound Cas had made hadn’t sounded pained at all, but Dean went back to being cautious anyway. Very slowly, he pushed in a third finger, and Castiel let out a low, wrecked groan, clutching at Dean as his hips trembled.

“Shhh, just relax, Cas,” Dean soothed the other boy, thrusting his fingers slowly and carefully as he stretched Castiel out.

Castiel nodded, biting his lip as he turned away and squeezed his eyes shut, trying to calm himself. Eventually Castiel began to relax, and Dean pushed in further, flexing his fingers and exploring. Castiel’s breath hitched again when Dean caressed a particular spot, and encouraged, Dean pressed harder.

“Dean!” Castiel gasped, his eyes flying open.

“Okay, Cas, okay,” Dean whispered, pulling his fingers out slowly. He reached for the condom, tearing it open with his teeth and rolling it on. He was pleased to find it was the kind with extra lube on it, but just to be safe, he grabbed the bottle and applied more.

Castiel didn’t take his eyes off him as Dean moved down to position himself, and Dean found himself struggling to breathe a little at the enormity of what they were about to do. Cas seemed to sense his nervousness though, reaching up to cup Dean’s cheek with his hand and caress it softly with his thumb. Dean almost huffed out a laugh at the thoughtfulness of the gesture, because, well, wasn’t Cas supposed to be the nervous one here? He gave the other boy a soft smile in response, leaning down to kiss him again.

Pressing his forehead to Castiel’s, he pushed himself a little way in. Cas gasped and panted underneath him, but again he didn’t meet as much resistance as he thought he would, so he pushed in further, slowly but firmly seating himself inside the other boy. Castiel was so warm around him, fitting around him snug and just right, Dean had to pause, steadying his ragged breaths.

“Oh, God, Dean. You’re inside me!” Castiel gasped, “You’re really inside me!”

“Shhh, it’s okay Cas, I’ve got you,” he murmured.

Dean felt the other boy nod a little, and heard him trying to calm his own rapid breathing. When Dean felt Cas had relaxed enough again, he pulled back, and slowly began to thrust.

At first all Castiel could do was clutch at Dean’s shoulders, anxious and overwhelmed, but eventually Cas’ hips began to move, shakily matching Dean’s movements. Then Dean sped up his pace a little, and Castiel met his rhythm with growing confidence, wrapping his legs tighter around Dean’s waist.

Dean settled into the embrace, planting lingering kisses on Cas’ mouth, and the other boy released his grip on Dean’s shoulders, hands cupping Dean’s cheeks as his lips met Dean’s, stroking Dean’s face and neck with trembling fingers.

Dean shifted his hips, aiming for that spot he had found earlier, and after a few tries he found it. Castiel released a strangled groan, and Dean kept pushing against that angle, thrusting deeper with his hips, and Castiel’s hands went to his back, urging him on as his mouth latched onto Dean’s.

All too soon they could barely even kiss each other, unable to do anything other than gasp and moan against the drag of each other’s lips. It was all too good, happening too fast, and although every fibre in his body wanted to rush forward to it’s conclusion, instead Dean slowed his pace again. He wanted this to be good for Cas, wanted Cas to get as much out of it as he was. Because this right here, was the best he’d ever had.

And probably the best he would ever have.

So Dean kept at his maddeningly slow pace, for longer than he had ever lasted before, until Castiel was trembling beneath him, his entire body shaking weakly and barely able to meet Dean’s thrusts anymore. And even though Dean could’ve come every time Cas whimpered his name, he held back, thrusting slow and steady and needing this to last forever. Needing to remember every detail forever. And needing Castiel to remember it as well, to remember Dean for the rest of his life. Because Dean knew he would never forget this for as long as he lived.

“Dean! I can’t-- I need… Dean, please!” Castiel whimpered helplessly beneath him, shutting his eyes tight as the wet streak of a tear rolled down the side of his face.

Dean couldn’t drag this out any longer.

He reached down in between their bodies, grasping Cas’ length in his hand and giving it a couple of firm strokes, and Cas let out a strangled sob, climax spilling over Dean’s hand as Cas’ body clenched and throbbed around him.

It was enough to drive Dean over the edge as well, face buried in Castiel’s neck, crying out Castiel’s name into his skin.

~

Dean carefully pulled himself out, unable to look the other boy in the eye as Castiel hissed at the loss of contact.

He got out of bed straight away and went to the bathroom, flushing the condom down the toilet and cleaning himself off. For the second time that night he found himself leaning over a sink, splashing water on his face and heaving a weary sigh. Only this time, he couldn’t even bring himself to look at his reflection, not wanting to see what it held.

He found a small washcloth and brought it back to the bedroom, sliding back into the bed and gently cleaning Castiel off.

"Thank you, Dean," Cas whispered, and Dean nodded mutely in response, still unable to meet Castiel's gaze.

The other boy fell asleep beside him almost immediately, utterly exhausted, but Dean stayed awake, watching his friend until the sun began to rise, stroking his fingers through Cas’ hair and whispering all the things he’d ever wanted to tell the other boy, pretending that Cas said them all back.

And if the pillow was a little wet when Dean left, well, he was sure it would be dry by the time Cas woke up.

~

Cas called him the next day, but he ignored it. Cas sent him messages, asking him where he was, if he was okay, if they were okay… but he didn’t reply.

For weeks, Cas kept trying to reach him… but Dean never once answered.

Castiel had utterly ruined him.

Dean had wanted to remember every detail of that night… and he did. Too well.

It haunted him. Followed him everywhere. Day and night.

How the hell was he supposed to move on from this?

How the hell was he supposed to go back to being friends?

And how the hell was he supposed to say goodbye?

~

Dean lay curled up in his bed, staring blankly out the window and trying to remember to breathe every once in a while.

It was the day of Cas’ flight.

Cas was leaving.

And every time Dean remembered that, he had to swallow down the lump that threatened to spill up his throat into screams.

His hands twitched uselessly beside him, wanting nothing more than to grab Castiel in his hands and never let go.

But Cas was leaving.

And then his hands itched to curl into fists and beat at something until they were bloody and raw.

But instead, he just tried to remember to breathe every once in a while.

~

Dean’s phone rang.

But he knew who it was.

He almost didn’t hear the phone beep, alerting him he had a voicemail. But sometime after, his hand reached out, of its own accord, and picked up the phone.

Drawing in a shaky breath, he began to listen.

“Dean,” Castiel’s voice came through the speaker, still scratchy and deep like it had been that night, and Dean’s eyes clenched shut as his chest constricted.

“I’m at the airport, waiting for my plane, so I thought I’d try to get through to you one last time.” Castiel drew in a shaky breath. “I sorry, Dean. I’m sorry things changed between us. I already miss you so much…” Castiel said, his breath hitching. “I didn’t know it would be this hard… But I just… I just wanted to have you one time… Just once before I had to leave. Dean, I’ve been in love with you since I first saw you leaning against your locker door--” Castiel choked off. “I’m sorry, I shouldn’t have said that,” Castiel said in a rush. “I’m sorry I was so selfish, Dean. I just… I just hope you don’t hate me too much. I know it’s probably too much to ask, but I hope that someday, maybe we could even be friends again.” Another deep breath, and then, “Goodbye, Dean.”

Dean was barely breathing by the time the message ended.

And before he knew it he was throwing himself into his car, breaking a bunch of road rules, and desperately praying he would get to the airport in time.

Castiel loved him.

Cas loved him!

Cas had been in love with him… for as long as he’d been in love with Cas!

And it all made sense now, as memories of the past year they’d spent together flashed through his head, every action and reaction replayed… every word, every small smile, every soft touch… and oh god, that night… every moment must have been as achingly perfect and as painful for Cas as it had been for him

And now Cas was leaving, thinking Dean hated him. Cas was going off to college and was probably going to let some other guy put his hands all over him… and that? That was just not going to happen. There was no way Dean was going to let Castiel go without telling him how he felt.

He ran through the airport as fast as he could, his heart leaping through his chest as he pushed his way through security checks and idling travellers to get to Castiel’s departure gate. He was almost beginning to think he was too late… When finally he saw the slumped back of a trenchcoat, disappearing around the corner of the connecting hall to the plane.

“Cas!” he called out, running into the corridor and ignoring the surprised protests of the gate attendant.

“Dean?” Cas came back around the corner, confusion crossing his features.

Dean ran right up to the other boy, grabbed Castiel by the lapels, and crushed his lips to Cas’ mouth.

Castiel squeaked in surprise, before he melted into the kiss, dropping his bag and wrapping his arms around Dean’s neck, and kissing him back for all he was worth.

Dean finally had to pull away for air, pressing his forehead to Castiel’s.

“Cas,” Dean rasped, “I love you, too. I’ve been in love with you since I saw your stupid big blue eyes on me the first day of school.”

“Dean,” Castiel exclaimed breathlessly, eyes wide with shock and hope as he pulled back to search Dean’s face, and softening at what he saw there.

And then the gate attendant cleared her throat behind them, politely but pointedly.

Castiel choked out a pained noise, clenching his fists into the back of Dean’s shirt as he pressed his forehead to Dean’s again.

All that time they’d wasted. And now Castiel had to leave.

Dean’s hands let go of Castiel’s coat, moving up to cup Cas’ face and caressing the other boy’s cheeks softly with his thumbs.

“Wait for me, Cas,” he whispered. “I’m gonna come to you. As soon as I get together enough cash, I’ll make my way to you. I wanna be with you, Cas.”

“Dean,” Cas breathed, his voice shaky and overwhelmed, “Of course I’ll wait!” he promised. Then Cas let out a small snort. “I’ve waited this long haven’t I?”

Dean huffed out a laugh.

“But, Dean,” Castiel murmured, serious now, “That doesn’t mean that I don’t want you to hurry.”

Dean nodded, grinning as he pulled Cas in for another kiss, this time gentle, and full of promise.

“I’m sorry, sir, but you really have to go,” the gate attendant interrupted softly. Dean wrenched his lips away.

“Okay,” Dean breathed, stroking Castiel’s face one last time. Finally he pulled away. “Okay,” he said again to the gate attendant, before looking back at the other boy.

“See you soon, Cas,” Dean murmured, reluctantly backing away. Castiel gave him a soft, but sure smile.

“Soon.”

POSTSCRIPT

10 years later, Dean Winchester was running his own garage, Castiel Novak was running Dean’s books… And when Dean went to his High School reunion with Cas by his side, he felt like a winner.

~ fin

Bonus! Check out the epilogue here :)