Title: The Trenchcoat Avenger of Truman High

Author: rons_pigwidgeon

Pairing: Dean Winchester/Castiel

Rating: NC17

Warnings: Masturbation, Underage Drinking, Phone Sex, Anal Fingering, Anal Plug, Sex Toys, Blow Jobs in a Car, Car Sex, Sex in the Impala, Bathroom Sex, Hand Jobs

Chapter Summary: Dean and Sam take Castiel on a road trip to Seattle. On the way, he is introduced to such exotic wonders as Bobby Singer's house (and Bobby Singer himself), hustling pool in biker bars, cheap motel rooms, and drunken sex in the Impala.

Author's Note: Unbetaed chapter for now. If you see any grammar/spelling issues, please let me know, and expect a re-post with edits sometime soon.

Please note that additional tags have been added to the story's description.

The apartment is only slightly less swanky than the dorm was, but Dean doesn't really plan on seeing much of it. Sam is looking at it like he can't believe what he's seeing. "Cas lives here?"

"Apparently. He moved in a couple weeks ago, says he doesn't want to move all his stuff back to Ohio just to come back again in the fall."

"This is… really nice. Do you think it looks this nice inside?"

"Probably. Let's find out." He heads up to the front door, but pauses before reaching for the bell to turn to Sam. "Remember, Cas doesn't know anything about hunting. We cannot say anything to him, and under no circumstances does he get anywhere near the trunk, got it?"

Sam rolls his eyes. "Of course, Dean. Do I look stupid?"

Dean shrugs and rings the bell with Linn-Mathews on it.

"Hello?" Avery's voice crackles through the call box.

"Hey, Avery, it's Dean."

"Hey, hottie. Here to whisk Cas away for a few weeks of hot sweaty man-sex?"

Dean glares at the speaker. "Can you just buzz us in, damnit?" The buzzer sounds amid peals of laughter. Dean jerks the door open and goes inside, waiting for Sam and leading him up the stairs to the apartment number Cas gave him. The door opens before they can knock, and Cas is standing there in plaid shorts and a v-neck t-shirt that makes him look both very gay and very hot. Dean has to push the urge to kiss him hello down deep in his gut. "Hey, Cas."

"Hello, Dean. Hello, Sam." He reaches up to hug Dean, arms slinking up around his neck as he pulls him in. Dean doesn't think it's his imagination that Cas doesn't have to reach quite as high anymore, and his shoulders feel a little broader under Dean's hands. Dean really, really wants to kiss him, but he manages to quell the urge with a quick kiss to Cas' throat that hopefully Sammy can't see.

"Kiss him and get it over with. Jesus, we all know you're fucking. Might as well get a free show out of it," comes Avery's voice from behind Cas. Dean looks past Cas to find her leaning against the door jam in the lowest-cut top he's ever seen outside a bar and short shorts that would make the Spice Girls blush, smirking at him.

"Christ, Avery, could you not be crazy for like two seconds? You're going to scar my little brother for life," Dean grumbles as Cas lets him go to pull said brother into a decidedly more platonic hug of his own. Sam's eyes look like a bug's they're so big, but Cas pats his back and glares back at Avery.

"Please ignore my friend, Sam. She is not often permitted in company for obvious reasons."

"Are you guys really…?" Sam manages. He still looks like someone pulled the bottom out of his world.

"Don't worry about it, Sammy. She's just teasing." Dean ruffles Sam's hair and pulls him in to give him a noogie that manages to distract him enough to drop it, whining at Dean about not playing fair. Dean knows they'll have to talk about it later, but for now, they're fine. "Got your bag, Cas? We were hoping to get to South Dakota by tonight."

"Are we going to Mount Rushmore? I've always wanted to see it," Cas asks as he steps back into the apartment, nudging Avery out of the way. She's eying Dean like he might do for dinner. Dean rolls his eyes at her.

"Sure, whatever you want. Sammy and I have pretty much seen all of it before, haven't we, Sammy?"

Sam pushes him for the nickname but nods, smiling. "It'll be fun to see it with you, though, Cas. We never really get to go places just for fun."

"All that driving around and you've never gotten to enjoy anything you've seen?" Avery asks.

Dean and Sam pass a look to each other and shake their heads. "Dad's always got a job to do," Sam offers as Cas steps back into the hall with a rolling suitcase that's as violently colored plaid as his shorts. Dean tries not to make a face.

"What's your dad do?" Avery asks, leaning her head against the door jam.

"He's a mechanic," Sam says. Dean catches him glancing down at her breasts and smirks to himself.

"And he drives all over the country doing that?" She's too damn smart for her own good, and Dean remembers why he sometimes doesn't like her.

Cas saves them by kissing her cheek, and saying, "We should go. I'll be back in a few weeks. Don't have sex on my bed."

"I make no promises, Novak," she grins before glaring at Dean. "You take care of that little nerd for me. If he doesn't come back in one piece, we're going to have words, got it?"

"Don't worry, he's safe as houses with me. See you in a few weeks."

"Don't do anything I wouldn't do!" she calls after them as they retreat down the hall.

"That doesn't leave much!" Cas calls back, grinning at her over his shoulder.

"Damn straight! Remember, condoms are your friend!"

"AVERY!" They hear her giggling maniacally as they descend to the ground floor and out of the building.

"She's interesting," Sam says, still making a face from the condoms comment.

"Sam, put Cas' bag in the trunk," Dean says, unlocking the passenger door for Cas. Sam takes the suitcase and the keys thrown to him, eying the open door. Dean's going to hear about not letting him ride shotgun later, but he doesn't care, because he's got Cas pressed up against the car and is kissing him as soon as the trunk blocks Sam's view. Cas mmms against his lips and squeezes his arm before he gets in, just as the trunk slams shut and Sam tosses the keys back to Dean. Dean circles the car, still licking the taste of Cas from his lips. He tastes like milk and Apple Jacks and that damn apple shampoo he uses is going to drive Dean crazy someday. Dean slides into the driver's seat and turns the car on. Sammy's leaning over the divider with his chin on his hands, telling Cas about something Dean didn't catch.

"All right, Sam, what's the rule?"

"Driver picks the music, shotgun shuts his pie hole," Sam replies, making a bitchface at Dean in the rear-view mirror.

"That's right. Are we ready?"

"Yes, I believe so," Cas answers, smiling over at Dean. He looks a little mussed and golden in the sunshine and it leaves warm things in Dean's belly. He grins back at him and turns the car on, letting the sound of 'Thunderstruck' fill the interior up as he pulls out of his spot and they head west.

They're half-way to Bobby's when Sam finally asks the question Dean was hoping he wouldn't. So far, Cas has been telling them about school and his friends and how much he likes Chicago, while Sam asks questions and Dean cracks the occasional joke, but they've hit a lull in conversation, and Sam it seems wants to fill it in the most awkward way possible.

"So, are you guys really having sex?"

Dean has to fight not to swerve the car into the next lane in shock, and Cas laughs so hard he starts choking. "Jesus, Sammy! What the hell?"

"Well, I was wondering. Avery said you were, and she doesn't seem like a liar. And I'm not stupid. I've seen you kissing before."

"When have you ever seen us kiss?" Dean asks, slightly panicked. This was a conversation he was really hoping not to have.

"Just before we left Truman, and then again when I was putting Cas' suitcase away I saw you push him against the car."

"I was just teasing him."

"I know what kissing sounds like, Dean."

"You're right, Sam, we were kissing. And we have had sex… of a sort, before." Cas turns in his seat, all earnest and serious, to look Sam straight in the eyes. "But I promise you that we will not touch each other in that way while on this trip if that makes you uncomfortable."

Dean glances in the rear-view to see Sammy's face and finds relief there. "Thanks, Cas. It doesn't bother me, I just wanted to know. Just… not while I'm in the room, okay?" He pauses, then looks at Dean through the mirror. "Does Dad know?"

Dean clenches his fingers around the steering wheel. "No, and we are not telling him, understand? He doesn't need to know."

"What about Uncle Bobby? Aren't we sleeping at his house tonight?"

"Yeah, I don't know, what do you think?"

"Bobby Singer, your father's friend?" Cas asks, turning towards Dean so he can speak to them both at the same time.

"Yeah, he lives outside Sioux Falls. I called him yesterday to tell him we were going through South Dakota, and he wants us to stay with him tonight. He wants to meet you, but I didn't tell him about… us." Dean hesitates, glancing sideways at Cas. They've never actually talked about what they're doing with this, and Dean's not sure he wants to talk about it now.

"I don't think he'll care. Uncle Bobby loves you. I think he wants you to be happy, no matter what," Sam says, all sincerity and puppies.

"You think he'll tell Dad?"

"No. Remember that time he let us skip the shooting range and took us to a baseball game instead? He never told Dad about that."

"You're right. I guess we can play it by ear, then. Cas?"

"I think that sounds like a good plan. I'm excited to meet this man. You speak very highly of him."

Dean smiles. "Yeah, Bobby's pretty awesome." He launches into a story about Bobby that has Cas laughing and sparks a different story out of Sam. By the time they pass from Iowa to South Dakota, they've been telling him edited stories about Bobby for six hours. Cas is laughing over the story of Bobby trying to make gingerbread cookies and nearly starting a grease fire when they pull up to the house.

"But, why was there even any grease involved? You don't fry gingerbread cookies."

"Please try to tell Bobby that. I'd love to see his face," Sam says, laughing in the back seat.

"You can tell him now; we're here," Dean says, parking the car in front of the house. They haven't even gotten out of the car before the front door opens and Bobby comes out, looking cranky as ever, but still mostly happy to see them.

"Well, look what the cat dragged in. And you brought a stray with you this time, didja? He better not have fleas."

Dean rolls his eyes at Cas over the hood to show him Bobby is joking. Cas looks serious and shadowed under the flood lights. Sammy laughs and runs to give Bobby a hug. "Hey, Uncle Bobby, it's good to see you," he says into Bobby's shirt. He's still half-a-head shorter than Bobby and currently looks more like an eight-year-old than a fifteen-year-old. Dean has to resist the urge to roll his eyes. He catches Cas around the neck as they round the car, and Cas gives him an annoyed look but lets him drag him over to Bobby anyway.

"Hey Bobby, this is Castiel Novak. Cas, this is Bobby."

Cas slides out from under Dean's arm and holds his hand out. "Hello, sir, it's a pleasure to meet you. Dean and Sam have been telling me excellent things about you for the last several hours."

Bobby shakes his hand and shoots a look at Dean. "Yeah, I'm sure they've been telling you all kinds of stories. You hungry? It's a long drive from Chicago."

"We stopped for dinner a few hours ago, thank you."

"Well, let's get inside, and you can tell me about yourself, Cas. Dean says you go to some fancy college in Chicago."

Castiel smiles at Bobby and lets him lead him into the house, Sam following after. "The University of Chicago. I'm studying Linguistics. It's quite thrilling. Dean says you are quite the linguist yourself…" Dean loses track of what they're saying while he goes back to get their bags out of the car. By the time he gets inside, they're all settled in the family room, and Sam's talking about his perfect report card like it's his first girlfriend or something. Bobby's in his recliner, beer in hand, Sam and Cas are on the couch, Sam with a coke, Cas with a beer he still looks confused that Bobby served him. There's another beer sitting next to Cas' and Dean guesses it's his. He crowds Cas over on the couch and grabs his beer.

"There are quite a few weapons around," Cas murmurs to Dean.

Dean puts an arm over the back of the couch, fluffing Cas' hair as he does, and takes a gulp of beer. "Bobby likes to hunt on the weekends. Just assume it's all loaded and you'll be fine."

"Listen to him, Cas. I like hunting, and I don't like to unload. Don't touch any of it unless you know what to do with it," Bobby confirms.

Cas nods, still looking around the room. "You have an interesting book collection, Bobby. May I?" He moves to stand, and Bobby lets him after hesitating a moment, giving Dean a look as he gets up that Dean hopes Cas didn't see. He knows Bobby's going to want to talk to him later. Thank god he's already spun a tale to Cas about how Bobby was a PhD candidate in the occult before his wife died. Cas had sort of bought it in the car. Dean's hoping Bobby can figure the story out without a pow-wow, in case Cas asks—which he will because Cas always asks.

Cas starts looking through Bobby's books, pulling one out in a language Dean can't even begin to identify. "So, wanna watch a movie?" he asks, looking to Bobby. Bobby gives him the facial equivalent of Idjit and gets up to wheel the tv in from the bedroom.

Cas is all limbs, curled around Dean like a goddamn tentacle monster. Dean opens his eyes and winces, not quite ready to be awake yet. He glances up and sees Bobby sitting at his chair, feet propped up on the desk, watching Dean over his coffee mug. Shit.

"Somethin' you wanna tell me about Cas?"

Dean groans, "No," and buries his face in his pillow.

"Wrong answer."

He sighs and starts gently prying Cas off him, trying not to wake him. Cas mumbles in his sleep and turns over, pushing back into Dean. Dean takes the opportunity to slip off the sofa bed, and stretches. "Can I get coffee first?"

"Coffee won't make this conversation go away, boy."

"No, but it's too early for alcohol, and I'm gonna need something to get me through." He turns and goes into the kitchen. It takes him way longer than it should to pour a cup of coffee, he knows, but he doesn't care. He downs the first one like it's a shot of whiskey, ignoring that he's almost scalded his throat, and pours another cup before finally trudging back to the living room. Bobby's drinking his coffee like he's got all the time in the world. Cas has stretched out on the sofa bed and hasn't left much room if Dean wants to crawl back in. One look at Bobby and he knows that won't be happening. He circles the desk and leans against it next to Bobby's feet.

"Well?"

"Cas is… Cas and I… we sort of have a… thing, I guess."

"You don't say. I'm guessing your daddy don't know."

"He… he thought we were, but I convinced him we weren't. He wasn't exactly… happy, about the whole… guy thing."

"And the fact that Cas isn't a hunter and doesn't know anything about hunting wouldn't have anything to do with that."

"I've never had a… thing… with someone who did."

"Cas is smart. He's gonna figure something out. Just a matter of time."

"So, he figures it out. So what? There are plenty of people we save who find out about it. We let them have a pass. Why can't Cas?"

"It's not safe, Dean."

"Yeah, well, he's safe with me. So, are you okay with this or…?"

Bobby scoffs at him. "Boy, I don't care who you roll around with. Just don't be doin' it in my house, got it?"

"Yeah, Bobby, I got it. Thanks."

Bobby pats him on the shoulder and gets up to walk into the kitchen. "Breakfast'll be up in a minute. Wake Sleeping Beauty, will ya?" He turns his back on the room and starts padding around in the kitchen. Dean turns to look at Cas, sprawled out. He still looks hot, even drooling on Dean's pillow—especially drooling on Dean's pillow. Dean circles the desk again and settles back in the bed, stealing the pillow Cas isn't laying on and propping himself up so he can drink his coffee while Cas once more wraps himself around Dean's legs, using his thigh as a headrest instead of the drool-covered pillow. He makes a muffled pleased sound and burrows closer.

"I smell coffee," he rasps.

Dean swirls his cup near Cas' face before taking a drink. "Bobby's making breakfast."

"I heard him. He's right, you know. I will figure it out."

Dean freezes, shutting his eyes and clenching his jaw. "Leave it, babe. Believe me, you don't want to know."

"Bobby has an interesting book collection."

"Cas."

Cas starts to sit up, stretching his back and yawning wide. He looks at Dean seriously when he's finally sitting. It's not the sort of serious Dean really wants leveled on him. "Why do you hide from me? There's nothing you could tell me that would push me away."

"I'm a serial killer, Cas," Dean deadpans before the scary enormity of what Cas has just told him threatens to choke him.

Cas rolls his eyes. "No, you're not. You aren't a psychopath. You don't fit the profile."

Dean smirks over his coffee and pushes the other thoughts away. "I'm kind of a psychopath."

"Dean."

Dean rolls his eyes at the look Cas is giving him and leans over to kiss him. "Relax, dude, I'm not really a serial killer or a psychopath. But that's all you get. Don't go poking."

"But you poke me all the time."

"You're fun to poke." Dean pokes him in the side with a sly smile, liking the look of annoyed amusement that Cas' face turns into before Dean's dipping to kiss him again. Cas kisses back, curling fingers into his hair and pulling him closer. A pan gets knocked a little too loudly in the kitchen, and Dean pulls away, glancing at Bobby giving him the evil eye from the kitchen. No sex in the house, right, that probably means no making out where Bobby can see it either. He pecks Cas once more and doesn't complain when Cas steals his coffee cup and drinks the rest of it down.

"Are you a demon-worshiper?"

"What did I say about poking?" Dean pinches the bridge of his nose and takes a deep breath. He shouldn't have let Cas look at Bobby's book collection. Sam's asleep in the back, thank god.

"I want to know you, Dean. You tell me so many things about your family life, but nothing about what you and your father do for a living. I'm sorry if I'm being invasive, but I want to know everything about you. You know everything about me, don't you?" Cas' fingers creep over his thigh and squeeze.

"Cas, this is… I'm not allowed to talk about this. It's for your own safety. Could you just drop it, please?"

Cas is quiet for a minute, and Dean hopes that maybe he'll listen this time. Of course, he knows better. Cas is more persistent than a dog after a bone when he wants something. "Are you in the mob? Is that why your father gave you his car when you turned eighteen? Did you officially join the Family?"

"You caught me. Just call me Vito."

"No, that can't be right. You can't be a hero working for the mob, not matter how you contort your motivations. You also wouldn't be moving all over the place. And it doesn't explain all the hunting references or those occultist books of Bobby's."

Dean stares at the dark road ahead of him, hoping Cas will get tired and change the subject. He is surprised when he hears the click of Cas' seatbelt being released, and Cas curls into Dean's side, resting his head on Dean's shoulder. Dean lifts his arm over Cas and wraps it around his shoulders.

"Neil can't stop talking about how much he likes the ID you made him," Cas says quietly into his chest.

Dean fluffs his hair, grinning. "Is he buying all kinds of booze now?"

"Yes. The fridge has an entire shelf dedicated exclusively to Miller Light. It's disturbing."

"Happy to be an enabler."

Cas pinches his side, but doesn't say anything further. A few minutes later Dean hears soft snuffling noises and looks down to find him asleep. He smiles to himself and keeps driving.

Dean likes watching Cas in dive bars. They're at a tiny bar on the outskirts of Spokane. Cas is perched on the very edge of his stool, glancing uncomfortably at the other patrons. The only time he doesn't look uncomfortable is while he devours his burger. Dean glances at Sam and smirks at him. Sam just smiles and eats another fry. "Drink your beer, Cas." Dean says, pushing Cas' beer closer to him.

"Do they have a straw?"

"Babe, drink it. It's not poison, I promise."

Cas glares, but takes a drink, and then another. It isn't long before he's loosening up. Dean buys him another beer. He's giggling by the time it's empty and leaning into Dean, smiling at Sam like a sappy puppy. "You're brother's trying to get me drunk."

"Looks like he's doing more than trying," Sam responds, smirking over his coke.

"I think you're right."

"Wanna play some pool now that you don't care about the germs in this place?" Dean asks.

"Cas knows how to play pool?"

"Of course. Dean taught me the last time I saw him," Cas tells Sam, standing up. Dean follows, mostly because of the wobbling.

"You know… how would you feel about playing a stranger? For money?" Dean asks, remembering how good Cas was the last time.

"But I want to play against you. I can't touch you inappropriately if I'm playing against a stranger," Cas says, running his hand up Dean's chest in a caress.

Dean chuckles, catching Cas' hand and turning him around, pulling his back close to Dean's chest by that same hand. "Sam, meet drunk-and-handsy-Cas . Drunk-and-handsy-Cas, meet my little brother."

"Hell-ohh," Cas says, drawing out the O in an exaggerated slur as he waves at Sam with a goofy smile. Sam just laughs and shakes his head.

"Come on, let's find a victim for your adorable charms." Dean directs Cas towards the pool tables.

"I am not adorable."

"You are so adorable." Dean parks Cas in front of an empty table and pats his shoulder. "Okay, I'm going to go get us another round. I want you to look innocent and start asking the guys around here to play you. Tell them you're friends say you're so bad they don't want to play you. And if you find someone before I get back, play to lose."

"What, why? I'm good at pool, Dean. You even said so."

"I know, dude, that's why I told you to suck. You'll suck the first round, then ask for a re-match and bet the guy a hundred bucks you can beat him. And then do."

Cas squints at him, grabbing onto his shirt front and leaning into his personal space a little bit more than he probably should in a bar full of drunk bikers. "Are we hustling pool?"

"Yes, we most certainly are."

"I'm not comfortable lying to strangers, Dean."

"I'll suck you off when we get back to the hotel, after Sammy goes to sleep."

Cas scoffs at him. "You were going to do that anyway."

"Oh, I was, was I?"

"Yes, while fucking me with your fingers."

All the blood in his head makes a hasty charge to his lower extremity, and he has to hold onto the pool table to keep upright in the rush. "Jesus, Cas, talk like that any more and I'm gonna have to drag you to the bathroom and have my way with you now."

"Mmm, I wouldn't object."

Dean groans and gnashes his teeth together to stop the urge to lift Cas onto the pool table and take him right there. "I'm going to get us another beer. You find someone to play pool with. I'll be back in a minute." Dean walks away, heading back to the bar. He can still hear Cas for a few feet, already walking up to the nearest biker.

"Hello, sir, I was wondering if you might like to play a game of pool against me? My friends refuse to play with me because they say I'm terrible, but I really want to play a few rounds."

Dean hears the biker's deep laugh just as he reaches the bar. When he comes back with two beers and another coke for Sammy, who has gravitated to the pool table to watch, Cas is leant over the table, failing to hit the ball for the second time. The guy he's playing against is taller than Dean, packed tight with muscle, and covered in tattoos of pin-up girls and Harley Davidson symbols. Dean pulls a stool up next to Sam's and parks himself, handing Sam his drink.

"Is Cas really any good at pool?" Sam asks in a whisper.

"Better than Vinnie Markowitz."

"Wow. This should be fun."

"Yep." They settle in to watch. After Cas loses his first game horribly, he offers the bet and saunters over to Dean while the other guy sets the table up. He's grinning stupidly as he steps between Dean's spread knees and takes possession of his beer.

"Am I doing well?"

"Awesome, babe; you're doing just what you're supposed to. Kicks his ass this round, and we'll be up a hundred bucks."

"And then you'll suck me off?" Cas asks, blinking up at Dean with innocent eyes.

Dean should probably be less shocked by the statement than he is; it's not like Cas exactly has a filter while drunk. Dean hears Sam's gasp of indignation beside him. "Cas, watch it! Sensitive ears here."

Cas looks at Sam like he's never seen him before. "I'm sorry, Sam. I forgot you were there. If I win this game, your brother is going to suck me off in the car while you're asleep." He grins a happy, drunken grin and takes a deep drink from his beer.

Sam is coughing now, sounding like he's going to hack up a lung any second.

"Cas, language! Poor Sammy doesn't need to hear about what we do when he's not around."

"But I didn't curse, Dean."

Dean shakes his head, trying not to laugh at the earnest look Cas is giving him. He ruffles Cas' hair and nudges him backwards. "Go play pool before you traumatize Sammy for life. Your friend looks like he's ready for you anyway."

"Okay, but you owe me."

"Don't worry, I always pay my debts."

"I'll hold you to that." Cas gives him a hard look before sauntering back over to the pool table just in time to take his first shot. He sinks his first ball without even blinking at it. The biker looks shocked, as does Sam, who looks from Cas to Dean and back again.

"Did he just…" Sam whispers in awe.

"That's my boy," Dean murmurs, grinning into his glass. "Makes up for the childhood trauma, doesn't it?" An hour later, Cas has an extra four hundred in his pocket from two rematches, and Dean's leading him out under his arm, Sam trailing in their wake.

Cas is grinning ear-to-ear. "That was amazing! Did you see his face when I sunk that last eight ball? I thought he was going to have a heart attack!" he exclaims, all but bouncing on his toes in excitement.

"It was awesome, man! I only wish we could have you around more often. We'd be rolling in it." Dean grins back, pressing a sweaty kiss to Cas' temple. The heated look Cas shoots him keeps him pleasantly warm as they reach the motel.

"That was really cool, Cas! I've never seen someone play that well before, and this was only your second time, right?"

"Third, I played with my college friends a month or so ago. Kicked their asses, too."

"You should play professionally."

"He just did," Dean reminds him, fishing in Cas' pocket for the cash and waving it in Sam's face. Cas snatches the money back and stuffs it back in his pocket.

"My money, thank you."

"Our money. I told you what to do, and we need it to pay for the motels on the way back."

"Can we do it again?"

"I thought you didn't like lying to people," Dean teases, smirking.

Cas pulls the key from his other pocket and unlocks the motel room door for them. "I don't, but I also don't like being underestimated. I don't mind taking advantage of people when they think they can take advantage of me."

"No offense, Cas, but you do look like someone who would suck at pool. You can't really blame them for underestimating you," Sam says, making a beeline to his bed and pulling pajamas from his duffel.

Cas looks down at himself and then up at Sam, turning his head sideways in confusion. "Why do I look like someone who would not excel at pool? I am highly intelligent and have studied physics extensively."

"Yeah, but they're bikers. They don't know any of that. You're short and you look like you're my age. And you wobble when you're drunk. Easy pickings as far as they're concerned."

"Which is why we kick their asses and take their money, right Sammy?" Dean says, patting Sam on the back on the way to the bathroom.

"Right," Sam replies as he starts getting undressed and into his pajamas. "Don't take too long. I want to brush my teeth."

"Out in a second," Dean says as he closes the door. By the time he comes back out, Sam's in his pajamas and waiting with his toothbrush and toothpaste at the door. Cas is staring at his open suitcase like he can't decide what to do with it. Sam slides into the bathroom past Dean and shuts the door like he needs privacy to brush his fucking teeth, but whatever.

Dean takes the opportunity to sidle up behind Cas and pull him close, kissing the side of his neck. "Get dressed like you're going to bed. We'll sneak out to the car as soon as Sam's asleep," he breathes into Cas' ear, licking the outer ridge.

Cas makes a little whining noise and drops his head to the side to give him more access, his hands coming up to twine with Dean's across his waist. "Why do we need to sneak? Sam knows we're going to the car to have sex."

"Right, 'cause us just leaving for the car with a goodnight and a don't-wait-up wouldn't be awkward as hell."

"I don't think so. He knows what's happening. He's old enough to understand, and he's already said it doesn't bother him as long as we don't do it in front of him. How do you normally address leaving him to hook up with someone?"

"Call him and tell him not to wait up. But those are strangers. This is different."

"I don't think it is."

"You're too logical. Fine, get in your pajamas anyway. I don't want to wake him up when we come back in trying to get ready for bed."

"You just want to see me naked with the lights on," Cas scoffs, making a face at Dean over his shoulder.

"Mmm, you caught me. I can't resist that tight little ass of yours." He swoops in to steal a kiss before Cas can yell at him for vulgar language or something. Cas hums into his mouth as he turns around, raising up on his toes to meet Dean's mouth. Dean takes the opportunity to squeeze Cas' ass through his shorts, pulling him in close. Cas starts giggling, pulling away when he can't stop and falling into Dean's chest. He's still giggling as the bathroom door opens, and Sam comes out, looking very confused.

"You two okay?"

"I think Cas might be a lot drunker than he appears," Dean tries to explain.

"No, I'm fine, I promise," Cas assures, still giggling as he wiggles out of Dean's arms and pulls pajamas out of his suitcase. He stumbles on the way to the bathroom, busting out in more giggles.

"Yeah, you look fine. Need any help in there?"

"You would just loooove to help me, Winchester."

"Of course I would, babe." Dean goes to follow only to have the door shut in his face. Sam's laughing at him when he turns around. He glares at his little brother and roughs his hair up while pushing him towards his bed. "Yeah, yeah, go to bed."

"God, you're such a jerk," Sam shouts, pushing him away.

"Bitch," Dean snaps back. Sammy just grins at him and crawls in bed, shaking his head. He grabs his book and opens it like he's going to be up reading for a while and has no intention of going to sleep any time soon. Dean goes to his duffel and starts changing, eying Sammy over the bed. He doesn't think Drunky McGrabby-Hands is going to be able to keep things chaste if they have to get in bed together and wait Sammy out.

This is gonna be awkward. "If I tell you Cas and I are gonna go have sex in the car, are you gonna be a man about it?"

Sam makes the bitch face to end all bitch faces. "Dean, seriously? Can't you just say you're going to get ice together like normal people?"

"Yep, that's what we're gonna do. In our pajamas. For at least half an hour, probably longer considering how drunk Cas is."

Sam continues to bitch-face. "Great, now I have that image stuck in my head. I hate you."

"Back atcha," Dean says with a wink just as the bathroom door opens and Cas comes out in his Leave-It-to-Beaver pajamas. "Ready?"

Cas frowns, glancing at Sam. Dean just shrugs. Cas deposits his folded clothes on top of his suitcase, and meets Dean by the bed. "I'm ready for bed, yes."

"Awesome. Night, Sammy," Dean says, wrapping his arm around Cas' shoulder and turning him towards the door.

"Night guys. Enjoy getting your… ice," Sam answers, faking a smile. Dean has to resist the urge to laugh.

"Ice?" Cas asks, looking up at Dean with big blue eyes.

"Just say goodnight, Cas."

"Good night, Sam. Sleep well. We'll try not to wake you when we come back with the… ice."

"Thanks, Cas. Good night."

Dean doesn't waste anymore time pulling Cas onto the sidewalk, palming the keys on the way out. "But Dean, you forgot the ice bucket…"

"We're not getting ice, Cas."

"But Sam said…"

Dean just shakes his head and opens the car door. "Don't worry about Sam, babe. Don't you want your reward for kicking so much ass at pool?"

Cas stops looking back at the door and focuses on Dean. "My reward? You mean do I want you to suck me off while you finger me until I come? Yes, I would like that very much."

Dean groans and drops his head forward onto Cas' shoulder, smiling as Cas presses kisses to his neck. "That mouth of yours is going to kill me one day…" Cas giggles, licking under his chin. Dean never would have expected a year's worth of phone sex to be worth it, but damn.

"I like it when you turn pink."

Dean glares down at him, gently pushing him towards the open door. "I do not turn pink, asshole. Do you want a blowjob or not?"

"Of course, Dean." He turns and crawls into the backseat, wiggling his adorable pinstriped ass as he does.

Dean slaps his wiggling ass, laughing at the glare he gets in return as he climbs in after Cas. "Couldn't help it. Your cute little ass was begging for a slap."

"You will come to regret it, Winchester."

Dean crowds him back against the seat and nips at his lip. "Do you know how hot you are when you call me Winchester?"

"Why are you still talking? There are better uses for your mouth right now."

"Damn, Cas." Dean pushes Cas' pajamas top up high enough to lean down and lap at a nipple. Cas arches into his mouth, clenching fingers into Dean's hair to hold him against his chest. Dean nips at the little nub, humming as Cas hisses and pulls his hair. He bites harder, tugging a little, and Cas curses and shoves his head further down his chest.

"I'm not interested in foreplay. Suck my cock already," Cas growls, pulling harder at Dean's hair. There's no arguing with that; Dean's hands are already working Cas' pajamas pants down while he flicks his tongue at the head of Cas' dick. The pre-come is still slimy, but he likes the taste of it better this time. He settles his elbows around Cas' hips and licks up his shaft. Cas shifts his hips closer, humming. Dean smiles, watching Cas' face melt with pleasure as he sucks the head into his mouth. He closes his eyes as he starts sucking Cas down, concentrating on the taste of him.

Cas makes an impatient noise and shoves him up into a crouch, pulling at his t-shirt. "Take this stupid thing off. I want to feel you." He has the shirt off in another few seconds and pushes Dean's head back down. Dean chuckles to himself as he gets back to work, not wasting time in sucking Cas back down. Cas takes one of Dean's hands into his and brings Dean's first two fingers into his mouth, sucking on them and coating them with his saliva. When they're nice and wet, he pushes them down. "Inside me, now," he rasps, tilting his head back so all Dean can see is his chin.

"No 'please'?" Dean asks, trailing wet, sloppy open-mouthed kisses up Cas' shaft. He drags the two wet fingertips over the clenching skin of Cas' pucker, teasing it.

Cas' fingernails dig into his hairline. "Fuck off and fuck me." Dean grins to himself and gently prods the first finger in, nice and slow. It slides with more ease than he'd thought it would, and he gets a momentary image of Cas naked and stuffed full with his plug. He groans and pushes the finger all the way in to the third knuckle, and Cas makes a loud keening noise and arches his hips into Dean's hand. Dean crooks the finger, curious. It had felt good to him when Keri did it. Apparently, it was universal because Cas calls out his name and digs his nails harder into Dean's scalp. "Just like that, yeah… Fuck, Dean…"

Dean likes hearing his name spill out of Cas' mouth in that dirty, needy way. He pushes a second finger in along with the first, having to work a little more to get them both in before he can bend them slightly to stroke at the little bump he can feel just inside. He suspects the bump might be Cas' prostate, and the way Cas is practically crying above him convinces him it is. He teases it mercilessly, driving Cas closer and closer to orgasm, until Cas is a trembling mess underneath him, shooting string after string of cum into Dean's mouth.

Dean slurps at the messy head of Cas' cock, sucking down hard on the shaft and listening as Cas cries out above him. Cas' bare feet have curled over his shoulder blades and his toes clench at Dean's skin. His chest is heaving from the effort to breathe. He looks like a filthy mess, and Dean wants to eat him. Slowly, he pulls his fingers out, wiping them on the dirty rag shoved under the seat. He does his best to lick Cas clean of his cum while Cas' breathing slowly evens out. Eventually, Cas sits up, watching him with a look of wonder. Dean shifts uncomfortably on his knees, the hard floor of the Impala cutting into his skin.

"You like that?" Dean asks, smirking because he's already sure of the answer. Cas doesn't give one, just pulls Dean closer and kisses him breathless. He hand travels down Dean's bare chest and abdomen, starts plucking at the drawstring of his sweatpants. It's a relief when Cas finally frees his erection from the confines of his boxer-briefs. Cas' fingers are hot and tight around him, stroking with purpose. Dean's a little far gone to care that it's a chafing, until he does and has to pull away for a second. "Hold on," he mumbles, spitting in his hand and taking over Cas' stroking for a few second.

Cas wrinkles his nose and buries his face in Dean's shoulder. "That is unsanitary," he says as he reaches for Dean's dick again.

"Dude, I just had my fingers up your ass. You're really gonna get a little squeamish about spit?" Dean asks, chuckling. He nuzzles into Cas' hairline, smiling, his breath catching a little as Cas squeezes him hard.

"I should have gotten the lubricant from my suitcase," Cas answers.

"You brought lube with you?"

"Of course I did. I knew we'd be having sex."

"Oh you did, did you? A little presumptuous, don't you think?" Dean teases. Cas huffs a laugh and lifts his mouth to Dean's again, pushing him onto his back on the bench seat and straddling him. Cas' fingers speed up, stroking him faster with each gasp he lets out between kisses. His rough fingers feel amazing against Dean's over-sensitized skin. "Fuck, babe," Dean moans, clenching his finger against the seat. Cas pulls away from his lips with a wicked grin and crouches low over Dean's stomach, flicking his tongue over Dean's throbbing head. Dean cries out, unable to hold back his orgasm any longer with the feel of Cas' tongue on him and the sight of his scrappy dark hair bowed over him. Cas lifts his face out of dodge, smirking as he watches Dean's come shoot out over his stomach with a look of pure satisfaction.

He sits back on his heels between Dean's spread knees when Dean's finished, practically preening with how pleased he is with himself. Dean can't help but laugh at his expression. "Proud of yourself?" he rasps out, wiping the sweat from his forehead in an attempt to calm his trembling hands.

Cas nods, grinning, before he leans over to kiss Dean again. "I made you come with my own hands and got to watch you do it. I couldn't be prouder. You were beautiful," he says, voice a little rough with awe. Dean pulls him down for a deep, dirty kiss, tempted to flip him over and take him right there. If it weren't for the lack of lube, he might have really been tempted, but Cas deserves more than a quick half-drunk fuck in the back seat of the Impala for losing his v-card. He settles for kissing Cas until he's loose-limbed and giggly again, smiling down at Dean like a goof.

"Alright, sexy, I think it's time for bed. We stay in here any longer, and I'm gonna get leg cramps," Dean says, smacking Cas gently on the ass again. Cas grumbles, but reluctantly pulls his clothes back on and crawls out of the back seat. Dean follows suit, and they open the motel room door slowly, only to find Sammy slumped against his pillows, book fallen open on his lap, just beginning to snore. Dean rolls his eyes and goes over to move the book away and turn the light off. He goes into the bathroom to quickly clean the drying come off his stomach, and is crawling into bed with Cas a minute later. Cas doesn't waste time snuggling into Dean's side with a happy sigh. Dean drifts with thoughts of spending every night snuggled up with Cas, and for the first time in a long time, he thinks maybe it wouldn't be so bad to quit hunting and settle down somewhere. He drops off with a smile on his face, squeezing Cas gently in his sleep.

Cas has asked Dean if he could drive the Impala every day of their trip. Every day, Dean's response has been the same: "Sorry, babe, but no one gets to drive Baby but me." The morning after they leave Yellowstone on their way back from Seattle, Cas corners Dean in the bathroom with a coy smile he's only ever shown Dean while drunk and pushes Dean down onto the closed toilet bowl lid. Dean looks up at him with raised eyebrows, waiting to find out what Cas is planning.

"I want to drive the Impala today," Cas informs him, straddling his lap.

Dean shakes his head. "I already told you, Cas…"

"Dean, you are being unreasonable. You know that I am a more than capable driver, and under much worse circumstances than driving the Impala in the middle of summer. Do you realize that I have to keep cat litter in the back of my car during the winter so that it does not fishtail when it snows? Or that it requires a feet of strength just to turn the wheel more than 20°?"

"I get it, I do, but I don't trust anyone to drive Baby but me."

"Are you saying you don't trust me with your car, Dean?" Cas trails his fingers over Dean's shoulders, down his chest.

"No, I just…" The lower Cas' hands get, the harder it is for Dean to think straight.

"You trust me with this, don't you?" Cas asks, his voice going as low as his hands, cupping Dean's half-hard dick through his boxers. Dean grabs onto Cas' thigh, trying to hold back a groan. Cas is persistent, starting to stroke him through his underwear. "You do trust me to take care of you, don't you, Dean?"

"Jesus, Cas…" Dean mutters, dropping his head back against the wall, eyes drifting to the ceiling. Cas' fingers aren't letting up, just getting stronger and faster. Dean's caught so off guard, he doesn't have the wherewithal to try to hold out for a respectable length of time. He's clenching his bottom lip between his teeth to keep from calling out as he comes.

When Dean opens his eyes again, Cas is practically preening like a fucking peacock. "So? Can I drive?"

Dean chuckles, shaking his head a little. "You sly bastard… You do anything to hurt Her, you're gonna owe me big," he finally capitulates.

Cas leans closer with a grin to kiss him, wrapping his arms around Dean's neck. "Thank you, Dean. Just think how sexy I'm going to look driving Her."

Dean groans against Cas' lips. "I swear to god, you're gonna kill me…"

"Don't worry. I'll make sure you die happy," Cas answers, kissing him again. They only stop making out when Sam bangs on the bathroom door.

"I don't want to know what you're doing in there, but it's 10:30. Can you hurry up so we can check out before we get charged another day?" Cas gets off of Dean's lap with a final peck to his lips. He has a smug smile on his face for the rest of the day. Sam looks shocked when Cas fishes the keys out of Dean's jeans pocket without asking and gets into the driver's seat of the Impala. Dean doesn't say anything, but he's already regretting giving in. Cas is going to be an impossible tyrant all day, he can just tell.

"You're letting Cas drive the Impala?" Sam asks from the back seat, sounding incredulous.

"Drop it, Sammy."

Cas pops the Metallica tape out of the player with possibly the most satisfied look Dean has ever seen on a person—including the first time he made Cas come—and places the tape on Dean's lap. He produces another one from places unknown and pushes it in and hits PLAY. The most obnoxious emo music Dean has ever been subjected to drifts out of the speakers. He groans, squeezing his eyes closed. "Damnit, Cas."

"Sam, can you remind Dean what the rule in this car is, please?" Cas says as he buckles his seat-belt and pulls the car out of Park.

"Driver picks the music, shotgun shuts his cake-hole," Sam answers, grinning like an idiot.

"I am so gonna get you back for this."

"Don't talk to me while I'm driving, Dean. You might break my concentration." Dean shoots him a glare, but Cas is too busy smirking smugly again to notice.

Pulling back up to the apartment building this time around is not as pleasant as the first visit. They're dropping Cas off, and Dean's not sure when he'll be able to get back to Chicago again. He finds a parking space half-a-block away, but is reluctant to get out. Cas turns in his seat and smiles. "This is my stop, I suppose."

"I'll get your bag for you," Sam says, reaching over the back seat to pull the keys out of the ignition. Dean's grateful for the extra privacy; as soon as Sam's out of the car, Cas is sliding across the seat to kiss him.

"I'm going to miss you," Cas says as he pulls away, eyes locking onto Dean's.

"Yeah, uh… me, too."

"Get back here as soon as you can."

"I'll try, but I can't promise anything. I'm gonna make sure it isn't as long as last time, though."

Castiel's quiet 'good' is accompanied by soft fingers rucking up his t-shirt as Cas crowds closer again for another kiss. The trunk is shut with a loud BANG, but Dean holds Cas in place for another few seconds of their kiss, reluctant to let him get out of the car. He does soon enough, getting out himself so he doesn't have to watch Cas slide along the upholstery of the Impala for the last time in what will probably be a long time.

Sam is waiting for them on the curb, the plaid suitcase parked next to him.

"Are you sure you don't want to come in for a while, eat dinner maybe?" Cas asks, turning from pulling up the handle on his suitcase.

"Nah, we've gotta get back, or Dad'll be wondering. Next time, though." Cas nods, his expression turning serious. Dean looks at him for probably longer than normal, soaking in every awkward, sexy inch of him. "Sam, turn around for a minute." Dean hears grumbling, accompanied by shuffling feet. Cas grins, leaning into Dean's hands cupping his face as they kiss, melting into each other. Dean wants to memorize the taste of him, the slide of his tongue against Dean's. Cas stands on tip-toe and buries his hands in Dean's hair, tugging it as he nibbles on Dean's lip before licking back into his mouth.

Eventually, Sam clearing his throat forces them to pull away. Cas is still smiling as Dean pecks his lips one final time. "I'll see you soon, okay?"

"Yes, you will. Call me when you get to your motel."

"Yeah, of course. Don't let Neil get you so drunk you get handsy, okay? I won't be around to grope."

"And I might have to find someone else? I'll think about it." He turns to Sam, smiling. "It was nice to spend time with you, Sam. I hope I see you again soon. You have my email address and my cell number?" Sam nods. "Don't hesitate to text or email me if you need anything."

"We don't have texting yet, but I'll email you. Thanks, Cas. It was good to see you, too." They shake hands. Dean makes a mental note to figure out what texting is finally. Sam gets back into the Impala, in the passenger seat this time. Cas looks up at Dean again. Dean looks back. A wolf-whistle sounds three floors up and they both look to see Avery and Neil leant out the apartment window, grinning and waving. Cas rolls his eyes and pulls Dean in for a final kiss.

"Goodbye, Dean."

"Bye, Cas." Dean waves to Avery and Neil and walks around the car to get in on the driver's side. Sam is already nose-deep in his book. Dean waits until Cas is inside the apartment before he pulls away from the curb.