The Long and Winding Road (amypond45) wrote,
The Long and Winding Road

MASTERPOST: Heartache Tonight - (Jared/Dean, NC-17)

Title: Heartache Tonight
Author: amypond45
Pairing: Jared Padalecki/Dean Winchester
Rating: NC-17
Word Count: 4.5K
Warnings/Tags: bottom!Dean, virgin!Dean, POV: Dean, pining, unrequited wincest, SPN/RPF crossover
Summary: It’s been two months since Sam left for college. On a lonely back road, Dean finds a kid who looks like him, heading towards California. It’s a bad idea.

A/N: The timing is a little off, but this story assumes Jared and Sam are the same age and each left his family in the summer of 2001 at the age of 18, Sam to go to Palo Alto, Jared to go to Los Angeles. Many, many thanks to onlythefireborn for the quick and helpful beta.

Read It On AO3


Dean finds the kid walking in the rain just before midnight.

He’s just left a bar in Seaside, and he’s tipsy, but definitely not drunk. The road is dark and slick with rain, so when the figure appears in the Impala’s headlights, at first Dean rolls right past it. The kid’s wearing a hoodie, shoulders hunched against the rain, walking with his back to traffic, barely on the shoulder. Dean has to swerve to avoid running into him.


Good thing he didn’t have that last beer. Dean glances into the rearview mirror -- just for a moment he could swear he sees Sam.

Which is impossible, of course. Sam’s in Palo Alto, deep into his first semester at Stanford. Dean’s already checked to be sure he made it, got settled in, seemed to be adjusting just fine to civilian life.

Just the way Dean had hoped -- and feared -- that he would.

Sam never knew Dean was there, of course. After the way Sam left, his father’s words echoing long after Sam slammed the front door, Dean assumes Sam doesn’t want to see him. But Dean can’t not check on the kid, however secretly. Sam’s his responsibility. Keeping Sam safe is Dean’s reason for living.

Dean’s on his way back to Palo Alto now, right after he does this job in Lincoln City. It’s a routine haunting in a wax museum tourist attraction, so Dean expects to get it done and be back on the road in less than twenty-four hours. Fifth job this month. Easy- peasy.

Every time he puts another ghost to rest or finishes off another werewolf or chupacabra, Dean feels better, if only briefly. Killing monsters takes his mind off his grief, fills the hole in his heart. The adrenaline feels like the rush he used to get whenever Sam smiled at him.

Dean keeps himself going, hoping for the day that Sam will come back to him. He doesn’t let himself think that Sam might not want to come back -- that after he gets a taste for civilian life, he might choose to stay. Dean doesn’t consider that. He can’t. If he started thinking that way, he might as well drive off the road and over a cliff and straight into the Pacific Ocean tonight. Right now.

Which he can’t do, because there’s a kid in his rearview mirror who looks like Sam.

He watches as the kid looks up, realizes Dean has stopped. He’s hugging himself for warmth, hood pulled low around his face. Dean leans across the seat and rolls down the passenger window as the kid jogs up and bends down, pushing his hood back so Dean can get a good look at him.

He definitely looks like Sam. Dean’s heart clenches.

“You need a ride?” he asks.

“Yeah! Thanks!”

The kid doesn’t hesitate, which breaks Dean’s heart a little. After all, it’s not exactly safe, getting into a stranger’s car on a dark, lonely road in the middle of the night. Nevertheless, the kid opens the door, slides into the car with a grateful smile, dimples and white teeth flashing. He’s soaked, so Dean cranks the heat as he pulls back onto the road.

“Your car break down?”

“What? No.” The kid shakes his head, sending droplets of water everywhere. “I missed the bus, so I just thought I’d walk.”

“Where’s your stuff?”

“On the bus,” the kid says. His teeth are chattering. He rubs his arms and hunches forward on the seat, holding his hands over the heating vents for warmth. His long, slender fingers are red with cold. They look just like Sam’s. “I was in the bathroom, and they just took off.”

“Where’re you headed?”

“Los Angeles.” He even sounds like Sam, high and soft, with a twang that reminds Dean of home. He fills up the seat just the way Sam does, too -- long, coltish legs bent open in the footwell. He’s tall, gangly, skinny. Too dim to get a good look at his face, but his profile’s sharp and angular. High cheekbones, straight, pointed nose with a little upturn at the end. Like Sam’s.

“Yeah?” Dean tries to keep his eyes on the road, tries not to stare. “What’s in Los Angeles?”

The kid grins, huffs out a breath, and puffs up his chest.

“Motion picture industry,” he says. “I’m an actor.”

“Oh yeah?” Dean’s interest is piqued. “You been in anything I might have seen?”

“Nah.” The kid sounds sheepish. “Just high school plays back home. I’m auditioning for stuff right now.”

“Oh.” Dean nods. “Where’s home?”

“San Antonio,” the kid answers. “Texas.”

Dean nods. “Explains the accent.”

He feels the kid’s eyes on him, considering. “What about you?”

“I’m from all over,” Dean says. “Tonight I’m headed to Lincoln City. Got a job there. Then I’ll be going south again, out of this rain.”

“I hear you,” the kid laughs. “Everybody back home said I should come up here to see the coastline, but it’s cold, man! Rains all the time. I’ll be glad to get back to L.A. and find the sun again.”

Dean nods, darting glances at the kid’s dimples, at the way his eyes light up when he smiles, even in the dim light from the dashboard.

“What’s your name?” he asks, then adds quickly, “so I’ll know who I met after you get famous.”

“Jared,” the kid says, still smiling. “Jared Padalecki.”

“Nice to meet you, Jared,” Dean says, sticking his hand out. “I’m Dean. Dean Winchester.”

He surprises himself by giving the kid his real name, something he rarely does. But there’s something about Jared that makes Dean trust him, probably against his better judgment.

Normally, Dean would figure this was too good to be true. He’d plan to test the kid, see if he was some kind of monster. Shapeshifter, maybe. Telepath. Witch. After all, what are the odds of running into a hitchhiker who looks like the brother Dean’s missing so much?

Maybe he’s being reckless, but part of him just doesn’t care. The part that misses Sam like a hole ripped open in his chest, like a raw wound that won’t heal, no matter how many monsters he kills or how much whisky he drinks. He’s willing to take the risk, just to pretend Sam’s with him again. He doesn’t give a damn if there’s something suspicious going on.

For the next hour they ride in companionable silence. Dean puts on Zeppelin IV, lets himself pretend Sam’s sitting next to him. The kid — Jared — falls asleep against the window, just the way Sam used to do. Dean glances over at him from time to time, missing his brother, protective of this young man who reminds him of Sam. In sleep, Jared seems impossibly young, bringing out all of Dean’s big brother instincts. It makes him sick to think of what might have happened to him, out there on the road alone, if Dean hadn’t come along when he did.

It’s after one o’clock in the morning when Dean pulls up to the bus station in Lincoln City. He walks with Jared into the station, but the ticket office is closed, the last bus of the night already gone. The next one isn’t due to leave until 6:30, later that morning. The station is deserted.

“Thanks for the ride,” Jared says, hunched over, his hands dug deep into the pockets of his jeans. Under the lights of the station waiting room, he looks even more like Sam than ever. Same height, same build. He’s even got little moles like Sam’s on his cheek and chin. Dean wants to brush the hair back from his forehead, to see if Jared’s got a mole there, too.

Dean can’t just leave him here. It’s not safe.

“Yeah, come on,” he says, gesturing back toward the car. “Let’s find a diner. I’ll buy you some breakfast. Dinner. Whatever.”

Jared hesitates, blinking nervously.

“You must be hungry, after all that walking,” Dean goes on. “Besides, it’s another five hours until this place opens. You can’t just stay here.”

“It’s okay,” Jared says. “Really. I don’t mind.”

Dean frowns and rubs the back of his neck. “Damn, you remind me of my kid brother,” he says. “So stubborn. Especially when he’s cold and hungry.”

Jared grins, ducks his head, and blushes. It’s adorable.

“You’ve got a brother?” he says, voice soft. “Me, too.”

“Yeah?” Dean huffs out a laugh. “Is he a major pain in the ass? Does he do stupid stuff like running out on you when you need him?”

As soon as the words are out, Dean wishes he could take them back. He doesn’t need to confess his sob story to this stranger. He doesn’t need to show off what a loser he is.

But Jared doesn’t seem to notice. He shakes his shaggy head and scuffs his toe, blushes and grins like he’s enjoying the conversation.

“My brother’s a superstar,” Jared says. “He’s perfect. Everybody loves him. When I was little, I wanted to be just like him, but now I know better. I’m just the family fuck-up.”

He bites his lip and looks up at Dean from under his bangs. It’s unbearably cute. Dean’s heart swoops right down into his belly, then back up into his throat, threatening to choke him.

“So now you’re going to Hollywood to be a star in your own right,” Dean says, encouraging despite himself. He can’t help it. Everything about this kid makes Dean want to protect him, take care of him, give him some armor against a cruel world he’s only just beginning to experience firsthand. “Now how about some greasy diner food, huh? Burger and fries? Bacon and hashbrowns?”

Jared nods, grinning and blushing, shuffling beside Dean back to the car. Their arms brush, and Jared doesn’t pull away. Dean lets himself imagine that the kid’s enjoying his company, that it’s not just the promise of free food that makes him accept Dean’s offer.

Dean doesn’t think too hard about how much he enjoys Jared’s company. It’s too obvious.

Susie’s Diner is right next door to the Motel 6 where Dean already booked a room, so he buys himself a beer while he watches Jared eat. It’s only a couple of blocks from the bus station, so if worse comes to worst, Jared can walk over to sleep there.

Dean’s hoping he won’t.

Jared talks and Dean listens, watching the kid’s eyes sparkle, his big hands move as he gestures while he eats. He tells Dean about the talent scout who saw his latest play in Texas and offered to help him if he made it to Los Angeles. His energy and enthusiasm are contagious, and Dean can see what the talent scout saw in him. Jared’s a winning combination of southern charm and youthful innocence. When he talks about his passion for acting, he’s beyond attractive. It’s downright sexy.

When Jared reaches across the table to grab Dean’s beer, and takes a long swallow, Dean’s not even surprised. Entranced, definitely. Jared’s long throat muscles move enticingly as he swallows, and the grin he gives Dean when he puts down the empty bottle is mischievous. Playful.

“You’re really gorgeous,” he says, as he wipes his mouth with the back of his hand. He holds Dean’s gaze for a moment before his eyes drop to Dean’s mouth. “I really want to kiss you.”

A jolt of lust flares through Dean before he can stop it. He wants it, too. He grins as he lowers his eyes, shakes his head.

“Man, I’m pretty sure that’s illegal in all fifty states.” He doesn’t mean the underage drinking.

“I’m eighteen,” Jared says. “And I’m offering, not selling.”

It’s Dean’s turn to blush. He huffs out a nervous chuckle, rubs the back of his neck. He’s more than a little turned on by this boy who reminds him of Sam. He knows it should bother him. It should sicken him. And it does. Wanting Sam’s look-alike fills Dean with self-loathing. But he can’t help it.

Dean’s not sure what he’s doing when he leads Jared back to the car. They barely look at each other as Dean drives across the parking lot to the motel office, checks in with the sleepy clerk, and drives down to the end of the building. Watching Jared in his peripheral vision, it’s like Sam’s sitting there next to him.

But when he gets out of the car, Jared bumps into him, lets his hand slide over Dean’s ass.

Jared’s bold and sassy, knows how to get what he wants, and right now it’s clear that he wants Dean. Dean’s hard in his jeans just thinking about it, which is wrong in so many ways. Mostly because he still wishes Jared was Sam.

But Sam wouldn’t be angling to have sex with him, and Dean wouldn’t ask for it.

Turns out, Dean’s the monster here. This poor kid never realized what kind of perv picked him up tonight. He’s pretty sure Jared would run screaming if he knew. He’s pretty sure Dean doesn’t look a thing like Jared’s brother.

Dean’s heart pounds. His palms sweat. His hands shake as he gets the door unlocked. Jared pushes up behind him, hands on his ass, his hips, his waist.

Inside the room, Jared shoves Dean against the closed door and kisses him, wet and sloppy, more than a little desperate. Jared tastes like bacon and beer. His hands are huge, they’re everywhere, pushing up under Dean’s shirts, making Dean moan.

“Couldn’t believe it when you stopped for me,” Jared breathes against Dean’s throat. “Couldn’t believe my luck.”

Dean gasps, tries not to think too much about how Jared sounds like Sam, how his hands and his body feel the way Dean imagines Sam’s would.

“And the way you kept looking at me,” Jared goes on, sucking Dean’s earlobe, licking along the shell of his ear. “Like you were just waiting for me to do this.”

“I don’t know what you’re talking about.” Dean throws his head back with a strangled cry as Jared’s big hand rubs over his erection. “I wasn’t looking at you like -- anything.”

“Yes, you were,” Jared pants, sucking kisses down the column of Dean’s throat as he squeezes his dick. “You kept looking at me like you wanted to eat me up.”

And before Dean can stop him, Jared slides to his knees, tugging roughly on Dean’s jeans, fumbling with his belt.

“Fuck,” Dean moans as Jared opens his jeans, pushes his boxers down, and slides long fingers around Dean’s dick.

Dean’s gonna come just from the thought of Sam sucking his dick. That should bother him. But when Jared gets his wet, hot mouth on his cock Dean loses all ability to think.

He forgets how to think at all.

“Fuck!” Dean squeezes his eyes shut, tries to think about dead puppies, anything to avoid the sight of not-Sam on his knees with Dean’s cock in his mouth, but it’s no use. He comes like a rocket, like it’s been forever since he had sex. Like this was the hottest thing that’s ever happened to him. Like he just couldn’t help himself.

Which, yeah.

It’s not like he’s never fantasized about Sam. He’s sick in the head, after all.

But to pick up some random dude on the highway just because he looked like Sam and do this... Dean’s pretty sure that makes him a whole new level of freak.

“Sorry,” he mutters, too late. “Sorry, man. I guess it’s been a while.”

Dean slumps against the door, his legs weak and trembling. He fumbles weakly with his jeans, but Jared’s big hands close over his, stopping him.

“I’m not done with you yet,” he purrs, planting a kiss on Dean’s thigh before rising to his feet. He pushes Dean against the door again and kisses him, deep and dirty, letting Dean taste himself, letting Dean know Jared took it all, swallowed his entire load like a pro.

Which is a distinct possibility, Dean thinks dazedly as he lets Jared undress him and manhandle him to the bed. Acting is the world’s second oldest profession, after all. Jared’s probably very good at that, too.

When Dean’s completely undressed, Jared gets up to pull off his own clothes, staring down at Dean the entire time. The kid’s body has more muscle than Dean would’ve guessed. He’s long and lean and toned, with powerful arms and shoulders. He looks like he could carry Dean if he had to, probably without much effort.

Dean recognizes other moles that are identical to his brother’s. Seeing them sends a little shiver of lust up his spine, makes his eyes flutter closed.

He’ll never put this behind him, the night he fucked a stranger because he reminded him of Sam. It’s part of him now. The monstrous, pathetic part of him that he’ll never live down.

No wonder Sam left. Sam must have been able to tell, just like Jared could.

Jared smiles, dimples showing and white teeth shining in the near-darkness of the room.

“Like what you see?” he asks, voice hoarse and rough. “God, you’re gorgeous all over.” He takes his erection in his hand and strokes it. “I could get off just looking at you.”

“Fuck me,” Dean pleads, hating how whiny he sounds, wanting Jared to use him. To punish him. Knowing he deserves to be punished for lusting after his brother and making Jared complicit in his perversion. He spreads his legs, reaches down to pull one knee back as he runs his other hand over his chest, tugs on a nipple. “Do it.”

“Jesus,” Jared breathes, stroking himself faster as he watches Dean touch himself. “Okay. Okay. Hold on a minute.”

Jared scrambles for his jeans, pulls a condom out of the pocket, along with a small tube.

“Guess you came prepared, huh?” It’s Dean’s turn to smirk.

“I’m from Texas,” Jared says, rolling his eyes. “I’m always prepared.”

Dean doesn’t ask what Jared means. Texas is a conservative state. Life can’t be easy for a gay boy growing up there. Jared’s probably been in his share of fights, maybe had the shit kicked out of him a couple of times just for being an actor, never mind gay.

The thought of this beautiful boy beaten and bruised just because his choice of sexual partners isn’t “normal” makes Dean want to hit somebody.

“Come here,” he orders, and Jared obeys.

“Don’t you want to turn around?” he asks hesitantly as he climbs up between Dean’s spread legs. “It’ll be easier that way. I’m kind of big.”

“Come here,” Dean says again.

Jared leans down, and Dean brushes the hair back from his forehead. Sees the mole exactly where he expected.

Dean’s hands shake as he cradles Jared’s face. They kiss long and deep, until Dean’s lips feel bruised and swollen. He gasps as Jared’s finger slips inside him, crooks until he finds the spot that makes Dean give a choked cry.

“Look at you,” Jared breathes, pushes another finger in alongside the first. “So open and willing. Like you were made for this.”

“It’s — it’s my first time,” Dean gasps, voice hitching. He doesn’t know why it’s so important for Jared to know. All he sees is Sam’s face hovering over him now, watching his responses.

“Oh my God.”

Dean wants to bottle the look of wonder and adoration on the kid’s face, keep it inside him forever. Jared leans down to kiss him, working him open with three fingers now, slow and careful. Reverent.

Sam used to look at him that way, when he was little. Like he was Sam’s whole world.

“Ah!” Dean cries out as Jared hits that sparky place inside him again. He squeezes his eyes shut to keep from coming.

“Good, isn’t it?” Jared purrs, stroking the spot over and over.

“I’m gonna blow — Wanna come on your dick, man! Come on!” Dean can barely speak, but he knows what he wants. He reaches down between them and grabs Jared’s slicked-up cock. He pushes Jared’s hand away and positions his cock at the entrance to Dean’s hole.

Jared pulls back, gasping. “You sure?”


Jared props himself up on one arm, guiding his cock with the other, and Dean braces himself for the burn. Welcomes it. As Jared breaches him, Dean gasps.

“Okay?” Jared hesitates, watching Dean’s face.

“Yeah. Don’t stop. Just do it!”

Dean arches up as Jared slides home, making them both groan, making tears leak from Dean’s eyes. He’s never done this, although he’s been fingered plenty of times. Sammy needed to eat, after all. He’s had more thick fingers up his ass than he wants to think about.

But never this. This he’s doing for the first time with a guy who looks so much like Sam it makes Dean cry.

“Hey, you okay?” Jared brushes Dean’s cheek with the tips of his fingers.

Dean nods, eyes squeezed shut as more tears leak out. “Yeah, I’m good. Come on, Jared. Give it to me.”

Jared pulls out halfway, then slams home again. Dean cries out, clutches Jared when he tries to pull out again.

“I’m hurting you...”

“No, no, it’s good,” Dean gasps. “Don’t stop!”

Jared slams into him again, and Dean bites back another cry. He tries to breathe through the burn, but all the air gets punched out of his lungs with every thrust. It hurts to move. He’s been impaled on a baseball bat. His world narrows down to the experience of being filled beyond capacity, to being repeatedly split in half.

Then Jared hits the place inside him that sends sparks sizzling up his spine, leaving a rush of sensation that’s almost pleasurable. He gasps in shock, and his eyes fly open.

“Yeah, that’s it.” Jared’s grinning face hovers over him, reading his expression. “That’s good, isn’t it?”

Jared leans down to kiss him, and now every thrust makes Dean’s spine tingle. It still hurts, but now the discomfort is tinged with little electric shocks. Dean would be lying if he said it didn’t feel good.

Jared knows. Jared finds the right angle and hits that spot inside Dean over and over, holding him in place with his giant hands. He grabs Dean’s wrist, hooks Dean’s knee over his shoulder, spreading him impossibly wide as he fucks into him, relentless.

Dean’s cock has hardened again, and Jared grabs it, clumsy and awkward but somehow just right. Dean throws his head back and keens as he comes again, eyes squeezed shut.

“Sam!” The word escapes Dean’s lips on a sigh. A prayer.

Jared groans as his own orgasm hits him, thrusts short and shallow as he works himself through it.

Dean’s eyes slide open, and he watches as Jared comes down from his high. Sweat plasters his hair to his forehead, his mouth soft and pink. Tears dampen his eyelashes.

This is what Sam looks like when he comes. Dean will hold onto this moment till the day he dies.

Jared opens his eyes, realizes he’s still got Dean bent in half, shifts to lie next to him on the bed. He hisses as his dick slips free, huffs out a laugh.


Dean tries to smile, but his chest aches. He’s crying again.

Jared reaches over, swipes his thumb down Dean’s cheek. “You okay?”

“I’m fine,” Dean lies. “That was awesome.”

Jared gazes at him another moment. “Can I ask you something?”


“Who’s Sam?” Jared asks, soft and careful, like he already knows the answer.

Dean blinks, heat rushing to his cheeks. “I don’t know what you’re talking about.”

Jared smiles, bashful and hesitant, and it’s adorable after his boldness and sass. Dean’s charmed all over again.

“You said his name, when you came,” Jared says. “I figure he must be somebody pretty special.”

It’s Dean’s turn to reach out. He tucks Jared’s sweat-damp hair behind his ear, leaves his hand on Jared’s cheek for a moment.

“He’s somebody I lost,” Dean admits finally. “He left.”

“Man, if I had somebody like you, there’d be no way I could ever leave,” Jared breathes, his sincerity as adorable as his earlier bashfulness. His earlier boldness.

Dean could fall in love with this kid.

Except his heart already belongs to somebody else.

Dean sighs, pulls his hand away. “Yeah, well, you don’t know me.”

“I’d like to,” Jared says, hopeful. Like a puppy that’s never been kicked.

Jared’s innocence is contagious, beyond attractive. He’s like Sam before Sam found out how dangerous their lives were.

And just like Dean wishes he could have protected Sam from ever finding out what they do, he knows he can’t let this boy find out, ever. He can’t ever get that close to anyone. It’s too dangerous.

“Let’s get some sleep, okay?” Dean says, trying to be kind, making an honest effort to let Jared down gently because he deserves nothing less.

He cleans up in the bathroom, then slips back into bed behind Jared, spooning him. The kid’s already asleep, but he scoots back into Dean’s lap, snuggles his arm against his chest and tangles their fingers together. Dean places a soft kiss on Jared’s spine, gets as comfortable as he can, and lets himself fall asleep pretending Sam’s here in his arms.

It’s the best night of sleep he’s had since the night before Sam left.

They get up at first light, shower, and go back to the diner for breakfast, not talking about the future by silent agreement. Dean’s grateful for that.

Jared keeps staring, and when Dean finally calls him on it, he says, “I never want to forget how you look right now.”

“Sap,” Dean mutters, ducks his head, and gives a little secret smile just for Jared to see.

Jared brushes his foot against Dean’s under the table and blushes. He pushes up behind Dean as they leave the diner and cross the parking lot to the car.

“Come on,” Dean mutters. “I’ll drive you to the station, make sure you get on your bus.”

In the car, Jared reaches across the seat, leaves his hand just touching Dean’s thigh, and Dean allows it. They sit for a moment in the station parking lot, watching as a bus pulls in.

“That’s probably your bus,” Dean comments. “Good timing.”

Jared nods. “If you’re ever in Los Angeles...”

“Hey, I’m gonna keep an eye out for you on my TV screen,” Dean says. “You’ll be starring in your own show in no time.”

Jared blushes. “I don’t know about that,” he says.

He looks up, eyes and lips soft, and Dean knows he’s hoping for a kiss, hoping for some kind of promise. Dean covers Jared’s hand with his, threads their fingers together, and squeezes. It’s the best he can do without crying.

“Come on, I’ll walk you in,” Dean says, reaching for the door handle.

Dean watches as Jared gets on the bus, finds a seat, gives him a little wave. He’s got Jared’s number on a diner napkin in his pocket, but he knows he won’t hold onto it.

When he gets back in the car, he opens his flip phone and scrolls through the numbers. He dials Sam’s number, although he knows Sam won’t pick up. He’s hoping it’s a game they’re playing. Dean’s sure Sam knows it’s him.

But for Dean, it’s a lifeline. And after last night, he’s less sure than ever that Sam will pick up.

He’s pretty sure Sam knows. Pretty sure Sam can tell.

Sam’s better off without Dean anyway.
Tags: bottom!dean, de-aged dean, jared padalecki, pining!dean, pov dean, rating: nc-17, sunday morning porn club

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