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

Remember to Always Think Twice

Title: Remember to Always Think Twice
Author: amypond45
Pairing: Sam/Dean
Rating: NC-17
Warnings/Tags: post-series first-time, Heaven!Fic, post-finale, wincest, humor
Summary: Some things get left until the work gets done. This is one of those things. Set just after the finale, in Heaven.

A/N: Please excuse the lack of beta for this — the pandemic has really been doing a number on my mental health, as I’m sure many of you can relate to! Hope you enjoy despite any typos or mistakes!

Now with art by tx_devilorangel! Be sure to visit their art post HERE or on A03 to leave some love!


“There’s only one bed.”

Dean stands in the doorway of the bedroom, staring at the offending object sitting squarely in the middle of the floor.

“Huh.” Sam moves up behind him, looks over his shoulder, and shrugs. “At least it’s a king.”

“Yeah, but this is Heaven, Sam,” Dean complains. “Everything’s supposed to be perfect.”

“So sleep on the couch.”

Sam’s lack of concern at this odd turn of events is truly irksome. Dean’s offended.

“I’m not sleeping on the couch,” he gripes, turning to glare up at his little brother. “Heaven, remember?”

Sam shrugs again. “So maybe we don’t need to sleep anyway,” he suggests. “It’s Heaven, right? We’re dead.”

“So why is there a bed here at all, if we don’t sleep?”

But Sam’s already gone, checking out the bookshelves in the main room, the nerd.

After meeting up on the bridge, they got in the car and drove, catching up on Sam’s life and Dean’s short time in Heaven so far. When Dean mentioned the Roadhouse and all the people who were probably waiting to greet them, Sam asked for a little more time alone first, just the two of them.

“It’s been thirty years for me,” he explained, and Dean understood. Sam’s missed him. Sam’s lived a whole lifetime without him. He’s just left his son, back on Earth. Sam needs time to adjust.

The house is theirs, of course. It’s fully stocked, with running water, electricity, and a fireplace. It reminds Dean a little of a house they once stayed in with their dad, right next to a lake with a boat dock and a couple of canoes. Sam chops wood while Dean grills steaks. He makes a salad for Sam.

“You know you don’t need to eat the green stuff up here,” he reminds his brother when they sit down to eat. “It’s not like it’ll keep you healthy.”

Sam smiles and chows down. The fire Sam built blazes cheerfully. They take turns showering after supper, Sam to clean off the sweat from his axe-swinging session, Dean to wash off the dust from his drive.

“The water pressure’s amazing!” Dean exclaims when he returns to the main room after his shower. Sam’s on the couch with a book, bare feet up on the coffee table, ankles crossed. Dean plops down next to him in a t-shirt and jeans, also barefoot. He’s got a whiskey bottle and a couple of glasses, pours a drink for Sam and hands it to him before pouring his own.

“Probably can’t get buzzed,” Dean muses as he sips. “But this tastes like that bottle we shared that night in Nebraska, after the Wendigo thing. Remember?”

Sam nods. “That’s the first time I remember feeling like we were really partners. Like we made a good team.”

“We did.” Dean nods. “We had a helluva ride.”

Sam raises his glass. “To us.”

Dean raises his glass, takes a sip. “Yeah. Hard to believe it’s really over.”

“Nobody to save, nothing to kill,” Sam agrees.

Dean shakes his head. “Can you believe it? We had to die just to get some time off.”

You had to die,” Sam reminds him. “I spent over thirty years grieving. Missing you.”

Dean winces. “Yeah. Sorry about that.”

Sam shakes his head. “It wasn’t all bad,” he assures his brother. He looks down at Dean’s hand, resting on the couch between them, covers it with his own. “Anyway, we’re here now. Together.”

In the old days, Dean would’ve pulled his hand away. In the old old days, he would’ve insisted on “no chick-flick moments.” He would’ve teased Sam for being a girl.

Now, he turns his hand over and tangles their fingers together. He gives in to the low-level erotic energy that’s always buzzed and thrummed between them, just below the surface.

What the hell, right? What’ve they got to lose now?

“Remember that time you walked in on me and Mindy Hastings?” Dean muses, smirking. “The look on your face.”

Sam rolls his eyes. “I was fifteen, Dean.”

“Old enough for an education.” Dean chuckles and takes another sip of his whiskey.

“You were an asshole back then,” Sam says, huffing out a disgusted breath. He keeps his hand where it is, though, so Dean takes that as a good sign.

“Stacy Peterson,” Dean goes on. “The one who kept trying to get you to join us.”

Sam shakes his head. “I hated you back then. All the teasing. That was a big part of why I left.”

Dean nods. “I wondered about that,” he admits. “Figured I was probably pushing a little too hard.”

Sam looks down at their clasped hands. “I never stopped wanting that. Even after everything that happened later.”

“Me, neither,” Dean admits. He’s surprised at himself, being so open with Sam about his deepest secret.

But maybe it isn’t such a secret after all. Maybe Sam’s known all along.

Sam’s multi-colored eyes gaze at him with a soulful, heated expression. When Sam’s eyes drop to Dean’s mouth, Dean tries not to hold his breath.

“We got all the time in the world now, Sammy,” he reminds his brother. “No reason to rush into anything.”

Sam smirks, giving his head a little shake. “You’re such a jerk. You know how long I’ve waited?”

“I got some idea, yeah.”

Their first kiss isn’t ideal. It’s even a little awkward. They’re sitting side-by-side on the couch, and when Sam leans in, Dean closes his eyes and turns away on instinct, so Sam’s lips catch the corner of Dean’s mouth and his cheek, mostly.

“Sorry.” Dean mutters. He opens his eyes to see Sam giving him that exasperated bitchface he loves so much.

“Hold still,” Sam commands. He takes Dean’s whiskey glass and puts it down next to his on the table. Then he drops Dean’s hand so he can take his head between his hands, hold it where he wants as he leans in again.

This time, the kiss works. It feels natural, like something they’ve been doing all their lives. There’s no sudden rush of guilt or shame, no worrying that Sam won’t love him anymore, now that he knows what a pervert Dean is. No fear that Sam might leave him.

It’s just them being them. The most normal thing in the world.

“Too bad we wasted all those years,” Dean says when Sam finally lets him up for air. “We could’ve been having so much awesome sex.”

Sam smiles, predatory. “Like you said, we’ve got all the time in the world.”

He leans in for another kiss and Dean opens up for him, lets Sam push him back on the couch so Sam can climb on top of him, straddling Dean’s hips.

“Can you take this off?” Sam tugs at Dean’s t-shirt and sits back to let Dean take it off.

Sam’s still wearing the purple whippet t-shirt he arrived in, but when Dean reaches for the hem, Sam obliges by pulling it off. Dean opens his hand, lays it flat against Sam’s chest, over his heart.

“My beautiful baby brother.”

“You’re such a pervert,” Sam teases, eyes blown dark with need as he leans down for another kiss.

“Takes one to know one,” Dean chuckles as Sam’s mouth travels down his neck to his chest. Sam slides down between Dean’s legs like he belongs there. When his tongue laves over one of Dean’s nipples, he gasps, grabs a handful of Sam’s hair, and tips his head back.

“Now I know why there’s only one bed,” Sam purrs as he sucks Dean’s nipple into his mouth.

“You don’t think Jack’s watching, do you?” Dean’s not sure if he should be horrified or turned on at the prospect. Maybe both. He really is a pervert.

“Would it matter if he was?” Sam bites Dean’s nipple lightly and Dean bucks up with a moan.

“Oh God!”

“Not anymore. Just Jack,” Sam answers, grinning evilly as he scoots down, tugs on Dean’s jeans. “Off.”

Dean unzips his jeans and lifts his ass so Sam can pull them off, along with his boxers. As soon as Dean’s naked, Sam doesn’t waste time. He grabs Dean’s cock as soon as it bobs free and swallows it down.

“Fuck!” Dean’s eyes squeeze shut against the sight of his brother, kneeling between his legs, half on, half off the couch as he sucks his cock. He shoves a hand into Sam’s hair. “I’m gonna come, Sam!”

Sam sucks harder, working the base of Dean’s cock with his hand, and it’s over pretty damn quick. The combination of the long wait, the years of pining, the dirty-wrong-bad kinkiness of the incest taboo, and the fact that Sam seems to be getting off on sucking Dean’s cock is just too much.

Sam swallows every drop, leaving Dean wrung out and sleepy. He lies loose-limbed and relaxed as he comes down, barely able to raise his hand from Sam’s head. When he finally opens his eyes, Sam’s looking up at him, giving kitten licks to his sensitive dick, obviously still horny as hell, the bitch.

“My turn,” he announces. “But I want to spread out on the bed.” His voice is scratchy and raw, and Dean’s dick twitches thinking about why that is.

“Sure thing, princess.”

Sam scoffs. “Right. I’m the one who lived to the ripe old age of eighty-four, and you’re calling me princess.”

“Damn straight.” Dean grins.

The sight of Sam spread out naked on the bed makes Dean’s dick perk up. Sam’s all long, lean muscle and soft skin, and Dean can’t get enough. He crawls up and straddles Sam’s hips, kisses him deep and dirty, tasting himself in Sam’s warm, wet mouth. He grabs Sam’s wrists and pins his arms up over his head, then kisses down the insides of his arms, to the dark, musky place where they meet his shoulders.


“Don’t worry. We’ll get there,” Dean murmurs against the soft skin of Sam’s collarbone. “We’re just getting started here.”

He kisses down Sam’s chest, sucks on his nipples one at a time as he caresses the delicate skin of Sam’s sides. The contrast between Sam’s soft skin and his hard muscles drives Dean to distraction. Sam’s long, lean body feels familiar and strange at the same time, his stubbled chin and the masculine scent of him unlike anything Dean’s experienced before. He’s not a prude, but his desire for Sam has always been wrapped up with his love for him, indistinguishable. Dean’s not into guys. He might have sucked a dick or two for money when he was a kid, but he didn’t like it, and it sure as hell didn’t make him want to do it again.

But Sam is Sam. He’s the most important person in Dean’s entire existence, alive or dead. Dean’s pretty sure he could’ve gone on forever not having Sam this way, but he’s damn grateful he didn’t have to.

When he gets to Sam’s dick, he takes his time, kisses the insides of Sam’s thighs, sucks on the juncture of his thigh and groin. Sam writhes helplessly under Dean’s mouth and hands. His hands flutter around Dean’s head, finally grab hold of Dean’s hair as he takes Sam’s generous cock in his hand.

Not to be outdone, Dean does his best to swallow Sam down as Sam had done for him earlier. But Sam’s huge. Dean splutters and chokes as Sam spurts precome down his throat, moans and thrusts uncontrollably until Dean’s throat is bruised, his jaw beyond sore.

But there’s no way he’s not giving a better blowjob than Sam gave him. He’s an awesome big brother, after all. He’s never had a lover he didn’t leave wanting more, and he’s not about to start with Sam, eternity in Heaven or not.

“Fuck fuck fuck!”

Sam lets him know he’s about to come by clutching Dean’s hair painfully, bucking up and going rigid the moment before he comes down Dean’s throat.

Dean swallows it all down like a champ, keeps sucking on the head till he’s got everything Sam can give him.

“That’s my boy,” he murmurs when he finally pulls off. He rests his cheek on Sam’s thigh, strokes the other one tenderly. His throat and jaw are sore, but he feels good. Satisfied. Complete.

“No work to do,” he murmurs, kissing Sam’s thigh as he gaze up his long body. Sam’s eyes are closed, but his brow stirs. He turns his head, looks down at Dean through heavily-lidded eyes. “We can do this all day. Forever.”

Sam shifts, lets out a laugh. “Yeah.”

Dean watches Sam’s dimples disappear as a frown creases his forehead.

“What?” Dean asks. He pulls himself up alongside Sam on the bed, props up on one elbow. “What’s wrong with that?”

Sam cracks an eye, rolls it. “I was just wondering how we’re able to do this in the first place,” he says. “I mean, we’re just souls now, right?”

Dean thinks about that for a second. “Yeah, I guess so.”

“So how come we have dicks?”

Dean brightens. “So that we can do this. Are you kidding me? How could it be Heaven without sex?”

Sam chuckles. “Yeah, but if you think about it, we shouldn’t need it. Like we don’t need to eat, or sleep, or breathe.”

Dean shrugs. “Jack is a benevolent god.”

“So you’re saying it’s all an illusion,” Sam goes on. “We just think we want to have sex. We’re not really having it.”

Dean frowns, flops over on his back, stares at the ceiling.

“What difference does it make?” he muses. “We both wanted it, back on Earth. So now we get to have it. After everything we went through, this is our reward. You know, like when you’re a kid and your parents make you sit on Santa’s lap, and you do it even though you hate it, but afterwards you get a candy cane.”

He can feel Sam’s eyes on him even before he glances over, sees those big hazel orbs all wide with surprise.

“Mom and Dad made you sit on Santa’s lap even though you hated it?”

“Of course they did! Everybody’s parents make them do that!” Dean shakes his head. “Look, that wasn’t even my point. I just think, now that there’s no work to do, no more monsters to kill, we’re finally free to do things we never would have done when we were alive, that’s all.”

Sam looks thoughtful. “Yeah. I guess. Maybe.”

At that moment, they hear the vibrating buzz of a cell phone.

Dean looks around, thinking maybe it’s his.

Sam’s eyes grow round. “What the hell?”

Then it occurs to Dean that they shouldn’t have cell phones in Heaven. There shouldn’t be cell service here at all.

“So I’m guessing there are no cell phones in the future.”

Sam stares at him. “No. I mean, we all have implants. Had. We all had implants.”

Sam’s out of bed, walking into the other room before Dean can react. By the time he gets up to follow, Sam already has the phone in his hand. He’s talking in a low tone, short, clipped answers to whoever’s calling.

Dean stands waiting in the bedroom doorway until Sam ends the call, turns to face him. The expression on his face is a mixture of surprise and deep concern.

“It’s Dean,” he says, then blinks. “My son, Dean. He needs our help.”

Dean’s eyebrows go up. “Okay. What can we do?”

“He says he can summon us back to Earth. And he needs to do it now.”

Dean doesn’t need to be asked twice. This — This is familiar. It makes sense. It’s what he does.

“Okay,” he nods, crossing the room swiftly to grab his clothes off the floor, tossing Sam’s to him as he starts pulling them on. “Let’s go.

“We’ve got work to do.”

( be continued...)

Tags: first time, wincest

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