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Sam leaned over the hood of the car, tossing a grocery bag at Dean through the driver's window before getting in. The Gas-n-Sip they had stopped at was no more interesting than the last one, but it meant that they were halfway to Illinois, where a sudden rash of deaths in the woods most likely meant that there was a case for the brothers involving a Wendigo. It had been a few months since the brothers took down a Wendigo, and Sam was hoping it would go more smoothly than it did the time before.
In the meantime, there was nothing more exciting to do than eat bad road food and listen to the old cassettes that Dean stored in the glove box.
"Got you everything you asked for," Sam sighed, opening his granola bar and getting comfortable in his seat. "Took forever to get the pie, they had to get some from the back."
Dean grinned, pulling the pie out of the bag and whooping quietly.
"What a good boy, Sammy, finally using that big brain for something useful," Dean leered at him, evidently expecting Sam to roll his eyes and glare at him.
Instead, Sam was silent, and pressed his lips into a thin line as he looked down at his shoes. Dean seemed put-out at the lack of a reaction, and turned the key in the ignition. Dean missed the faint flush on Sam's cheeks, and how he shifted in his seat afterwards.
It kept happening. When Sam slid his credit card across the counter to pay at a restaurant, Dean smiled, and said "That's a good boy." It never mattered that neither of their credit cards were actually sourced from money they earned. When Sam took a turn driving the Impala on a long trip, and didn't crash the car, Dean praised him, said he did good, and took the keys from him with a smile.
It happened with the littlest things, and it was throwing Sam incredibly off guard. Dean never used to compliment him regularly, and it was never with the kind of sweet, relatively patronizing words he tended to use as of late.
And, without fail, Sam got hard almost instantly, a pink flush spreading across his face and making him adjust himself in his jeans. It was the worst when they were in the car, and there was nowhere for Sam to hide.
So far, Dean hadn't taken much notice of Sam's reaction to his praise. If he did, he wrote it off as just one of Sam's quirks. As far as Sam knew, he hadn't realized he was unintentionally turning his little brother on.
Sam had pondered the psychology behind it during one late-night lore dive. He figured it was probably due to the fact that their dad never praised him for anything or said he did good growing up, and that Dean had pretty much subbed in as both his mother and father since they were both kids. Some of the wires were definitely crossed there, with Sam feeling the need to at least make Dean proud, if he couldn't make his dad proud.
Something about Dean's praise felt real, really real, and made Sam get all hot and flushed. He hadn't figured out how to hide his reactions yet, and he had been incredibly lucky so far that Dean hadn't noticed. For all that he seemed, Dean really was remarkably perceptive, and wouldn't take long to catch on once he recognized the real reason behind Sam's seemingly uncomfortable reaction.
He also wondered where Dean's sudden praise was coming from. Sam didn't think he was doing anything different from how he had been in the past few years, yet suddenly Dean was casually telling him he did well over the smallest favors.
Anyways, Sam wasn't complaining, not really. He just hoped Dean would stay clueless until he mastered his poker face.
—
Back at the hotel, Dean was lounging on the hideously patterned bedspread, making grabby hands at the remote on the desk. As Sam closed the door behind him, he tossed the remote to Dean without thinking twice.
"Good boy, Sammy," Dean said with a grin, pressing the buttons and starting to flick through channels. "C'mon, sit with me, let's watch Chopped or something."
Sam halted in his beeline for the bathroom, biting his lip and hesitantly crossing the room to sit next to Dean. His ears were red from Dean's comment, and a rosy pink color was dusted across his cheeks. Sam sat cross legged, folding his long legs to fit on the small bed.
He could feel warmth radiating from Dean's body, the two of them practically only half a foot away from each other. Sam prayed that Dean wouldn't look at him, but his prayers went unanswered as Dean glanced at him, his eyes flicking to the tv and then back to sam with a curious look as he took in the flush on Sam's face and his conflicted expression.
"Dude, are you okay?" Dean said with a frown, reaching out to feel Sam's forehead for any sign of a fever. "You're all red."
Mortified, Sam stuttered as he tried to think of an excuse. "Yeah, uh... it's just hot in here, that's all."
It wasn't even 75 degrees in the hotel room, but Dean wasn't going to start an argument with Sam by disagreeing, so he nodded peaceably.
"You've been working too hard. You've done so well researching the lore lately, Sam. You, we, deserve a break."
Sam blushed even harder at Dean's words, shifting on the bed. His fingers clenched where they were resting on his thigh, which didn't escape Dean's notice.
"Are you sure you're alright?" Dean said worriedly, grabbing Sam's hand, which made Sam startle. He felt Sam's pulse with two fingers, which was pounding wildly.
"I'm fine, Dean, seriously. Let's just watch whatever dumb show is on right now."
Acquiescing, Dean changed the channel to the Great British Bake-Off and resolved to think about what was wrong with Sam later. Sam sighed gratefully and settled on the bed, grabbing a pillow and putting it on his lap.
Sam had shifted closer to Dean as the show was playing, and strands of his long brown hair were tickling the side of Dean's face. It was making Dean's nose itchy.
"You should put your pretty hair in a ponytail if you won't cut it shorter, it's making me want to sneeze," Dean said, brushing the strands out of his face. Expecting a response, he looked at Sam, but the other man just looked back at him bashfully.
"You think my hair is pretty?" Sam asked Dean hesitantly.
"'Course it is, it's so long and shiny," Dean said, gesturing to Sam's hair, "Just think you should cut it so monsters can't pull on it during a fight, y'know?"
"Thanks, Dean," Sam said with a smile, and he shifted his leg higher so his hard-on wasn't visible to Dean's side of the bed.
—
"Can you put the pump back for me, Sammy?" Dean said from the driver's seat. "Good boy."
Sam nodded rapidly and got out of the car to do it, sitting back down awkwardly once he was done and shifting in his seat uncomfortably.
There was a moment of awkward silence as Sam stared at the floor, and Dean looked at Sam appraisingly.
"Sam, are you turned on right now?" Dean asked, disbelief in his voice. Sam jumped, and moved his hand to cover his crotch, which was sporting a sizable bulge.
"No, man, stop it!" Sam groaned, scrunching his nose and steadfastly refusing to look at Dean.
There was a glint in Dean's eye that said he wouldn't back down until he got to the bottom of what was getting Sam all hot and bothered.
"What did it, huh? Was it the girl that checked us out in the gas station? I didn't know you went for gingers."
"No, it wasn't," Sam snapped, looking out the window. His hand was still protectively hovering over his crotch, and Dean couldn't keep the smile off his face.
"Alright, but I'll make you tell me before we go to bed tonight, I swear."
Sam bit his lip at Dean's words and said nothing.
—
"Are you sure it wasn't the girl in the gas station?"
"Yes," Sam huffed, typing on his laptop.
"Was it the guy?" Dean said tentatively.
"No, Dean, it wasn't anyone in the gas station."
Dean hummed, tapping his foot against the bottom of the bed.
"Was it something I said?"
Sam jerked up in his seat, and instantly regretted it when Dean's face lit up.
"Now we're getting somewhere! C'mon, don't be shy, tell me what got Samantha all hot and bothered."
"Shut up man, it was nothing."
"Please?" Dean wheedled. "Promise I won't laugh. Was it when I asked you to finish pumping the gas?"
Sam groaned, and put his head in his hands. "Something like that, yeah."
"What else did I say?" Dean frowned for a moment, thinking hard. Then, a look of recognition dawned on his face.
I can work with this, Dean thought to himself.
"Hey, can you pass me the glass of water on the table?"
Sam nodded, and handed it over with a faint sense of unease.
After taking it, Dean leaned in, until he was just a few inches away from Sam's face. Sam stared back at him.
"Good boy," Dean whispered.
Sam couldn't hide the tiny sound that spilled out of his mouth. Instantly, his face flushed pink, and he knew he had been caught.
Dean looked like he was thinking hard, looking at Sam with a glean in his eyes.
"C'mere, Sammy. Not gonna get mad at you, I promise."
Sam had no idea where this was going, but couldn't think of a better idea than going along with whatever Dean said. Sam got up from his seat, and hesitantly sat down on the bed next to Dean.
"Not there, baby, here." Dean patted the space in front of his lap, and Sam, pink-cheeked and biting his lip, slid down to kneel in front of Dean on the carpet.
"Such a good boy," Dean said, reaching out to cup the side of Sam's face and brushing away the strands of hair that were stuck there.
"You're so beautiful, you know that? I've been thinking lately... I don't tell you that you did well as much as I should. You're so good, Sammy."
Sam moaned quietly, tilting into Dean's hand. He looked up at Dean through his long eyelashes, hazel eyes looking imploringly into Dean's own.
"Want to make you feel good like I did earlier, but on purpose this time, baby," Dean said, gently running his fingers through Sam's hair. He tugged on one section, and was rewarded by a soft gasp from Sam as his mouth formed a pretty 'o' shape.
"You like that?" Dean asked with a little smile, tugging on his hair more firmly. Sam was panting, and nodded shyly.
"Come up here." Dean patted his lap this time, and in a few seconds Sam was sitting in Dean's lap, his thighs spread wide over Dean's and hands tentatively sitting in his own lap. Dean reached out for one, and guided Sam's hand to his shirt.
Sam leaned in frantically and caught Dean's bottom lip with his teeth, giving it a quick bite before soothing the indent and licking into Dean's mouth. Sam's hand gripped tightly at the fabric of Dean's shirt as they kissed, Dean groaning in appreciation.
Dean broke away to take a breath, and Sam whined at the loss. Dean's eyebrows were raised, surprised.
"Where'd you learn to kiss like that?"
"Stanford," Sam said haltingly, hips twitching up from where he was sitting on top of Dean. Dean laughed, and rubbed the calloused tip of his finger back and forth across the delicate, heated skin of Sam's waist, right above the waistband of his jeans. The teasing touch went straight to Sam's crotch, heat spreading all the way to his toes and making Sam arch his back.
"Stop teasing, Dean, please," Sam begged, grinding down against Dean's matching bulge. They both groaned at the contact.
"Tell you what, let's put your pretty mouth to use, Sammy."
Dean pressed down on Sam's shoulders, guiding him down until he was situated in between Dean's thighs. Immediately, Sam leaned in, nuzzling Dean's crotch and pressing his nose into the space where Dean's thigh met his torso. Sam kissed his denim-covered bulge softly, then opened his mouth, laving wet kisses on his crotch until there was a large wet spot. Dean groaned, running his hand through Sam's hair and gripping it tightly.
Once Sam deemed him sufficiently hard, he unzipped Dean's pants and pulled them down along with his boxers. Dean's cock sprung free, and Sam's mouth watered. Without a delay, Sam captured the bobbing head with his mouth, giving it kitten licks until the head was weeping with precome. After that, he slid it into his mouth, using his hands to jerk off the base of Dean's cock.
"You're doing so well, baby, taking it just like that. You've got the prettiest lips for cock sucking, you know that? Such a sweet smile, and gorgeous pink lips, just makes me wanna see that mouth stuffed full of my cock. Been trying so hard not to think about it, when it turns out you were interested all along. Funny how things worked out."
Sam moaned around Dean's cock at the filth spilling from Dean's mouth, and slid his mouth further down on Dean's dick until Sam's nose was brushing the hair at the base of his cock. Drool was leaking from the corner of Sam's mouth, which was stretched wide around Dean as he eagerly sucked down his cock. Sam swirled his tongue around Dean's head as he pulled off, then went back down.
"God, I wish we could've been doing this earlier. If I knew some sweet words were all it would take to have you begging me to take you apart, I would've done this years ago."
Sam felt his dick twitch in his pants, and groaned desperately. The thought of Dean wanting him back this whole time was turning him on so badly he could barely think straight. That, combined with his praise, was making Sam dizzy.
Dean cupped Sam's face and pulled him off of his dick with a pop, Sam whining quietly at the loss.
"Shh, baby, I'm gonna come if you keep doing that. Lie down next to me."
Sam scrambled up on the bed, spreading his legs. His chest was heaving as he panted, looking up at Dean. Dean, although he seemed annoyingly in control of himself compared to Sam, was flushed as well, pink dusting the freckles that were spattered across his cheeks. His eyes looked darker than they usually did as he took in Sam's splayed out figure.
"Do you have lube?" Dean asked, fingers skimming across Sam's tummy and landing on his happy trail, playing with the soft trail of hair visible where his shirt had ridden up. Sam nodded. "Inside pocket on the left side of my bag," Sam said quietly. "There's some other stuff in there too."
Dean got up and rummaged through the bag until he found the pocket, where he pulled out the lube, as well as something dark and shiny. Dean looked at it with a smirk, and brought it back to the bed with him.
"Hands by your head, Sammy, and keep 'em there," Dean said. Sam nodded, and moved his arms, exposing the soft flesh of his tummy again.
"That's my good boy. Let's get you out of those pants."
Sam's breath was coming in staccato bursts as Dean unbuttoned his jeans and slid them down, taking his boxers with them. Immediately, Sam's cock sprung out of its confines, standing up proudly. The head was pink, and wet with precome, some dripping down his shaft. Little Sam was as big as the rest of him, Dean thought to himself with a chuckle. A soft smattering of light brown hair led to his dick, which stood at 8, maybe even 8 and a half inches, curving slightly to the left.
Sam spread his legs once they were freed, and Dean tsked at him even as he curled his hand around Sam's dick, stroking slowly.
"So eager, baby. Who knew it would take this little to get my good boy to open up for me?"
Sam whined sweetly, pressing his hands back into the mattress above his head as Dean jerked him off with fluttering, barely there caresses. The flush on his cheeks had spread down his chest.
"Dean, please," Sam said, tilting his head towards the lube.
"What do you want, pet?"
Dean definitely knew, but he wanted to hear Sam say it anyways. Sam groaned in embarrassment, the words pouring out of his mouth like he couldn't help himself.
"Want you to open me up Dean, c'mon, please, I've been good," Sam said in a rush, hips tilting up towards Dean's hand.
Dean smirked at his eagerness, and rubbed Sam's tip with his thumb until precome dripped steadily from it, Sam thrashing underneath him from the intense stimulation.
"Ah, ah, please," Sam whined, eyes screwed tightly shut. He was close already, and Dean took pity on him, taking his hand off of Sam's dick and reaching for the lube instead, keeping the other object he found in the palm of his hand.
Dean uncapped the lube and poured some on two of his fingers, tracing a line down Sam's dick and past his balls, pressing on his perineum just to make Sam jump with a startled moan.
Dean used his clean hand to push Sam's thighs upwards and apart until they were in the air, giving him a clear view of Sam's hole. Dean paused to take a good look, and Sam, embarrassed at Dean's intense scrutiny, tried to close his legs, to which Dean tutted and held them open.
"Don't be getting shy now, Sammy, we're getting to the good part. Your hole is begging for me to put something in it, with the way it's fluttering at me."
Dean rubbed his rim gently, just barely dipping a finger inside and then going back to rubbing the outside of his hole. Sam's thighs were twitching weakly.
"Dean, please," Sam said, hands clenching at the mattress where Dean had told him to keep them. He wanted nothing more than to grab Dean's hand and slide one of his thick fingers inside of him, which was probably exactly why Dean told him to keep his hands above his head.
"Shh, you're doing perfect, Sam. Just a little more for me."
Dean teased him for another few minutes, before taking pity on him and pressing one finger into Sam. Sam groaned as his hole gave way, feeling the intrusion as Dean's finger pressed against his insides, seeking out something specific. Finally, he crooked his finger against Sam's prostate, rubbing it, and Sam shouted, cock spurting precome against his stomach. Another finger joined the first one, both of them alternating between caressing his walls and stimulating his prostate.
As Dean played with him, Sam's eyes grew glassier, filling with pleasured tears. Dean noted with satisfaction that Sam was already thoroughly debauched from just two fingers.
"Alright, I think you're ready, Sammy."
Sam looked confused as Dean's words registered a few seconds later, and he looked at Dean, but he couldn't see what Dean's hands were doing from where he was lying. He felt something smooth and hard press against his hole, unyielding as it forced his hole to open for it. Sam bit his lip as Dean slid the object further inside him, filling him up pleasantly.
"What... what is it?" Sam asked, hips twitching at the full feeling.
"Oh, you'll see soon, baby."
He heard a clicking sound, and suddenly, Sam felt like he was on fire as the object started vibrating intensely.
Of course. Dean had found his vibrator.
"Ah, ah!" Sam moaned, his thighs spreading further apart like he couldn't help himself. Inside of him, vibrations were filling his hole and felt like they were spreading through his whole body, arousal making his toes curl and causing shivers to run down his spine.
Dean slid the vibrator a little bit further into Sam, and reveled in the hiccuping moans filling the air. Dean petted Sam's head, brushing his hair away from Sam's forehead where it was falling into his eyes.
"Such a pretty boy, Sammy, taking it all just like that for me. I love watching your little hole just swallow up everything I give it," Dean crooned in Sam's ear as he tilted the base of the vibrator so it would press on Sam's prostate.
Sam gasped and whined desperately, thighs shaking as his prostate was relentlessly stimulated by the vibrator. By now, a pool of milky precome had formed right under Sam's dick where it was standing up above his tummy, pooling underneath his dick and dripping down between his thighs.
Dean swiped his finger through it, and after collecting a generous sample of precome, rubbed his finger around Sam's rim, tracing where the vibrator was holding his hole open.
Sam's eyes were unfocused and glassy, and his mouth was perpetually open, letting out 'ah's and moans as Dean took him apart.
"Does that feel good, Sammy? Your hole says yes," Dean said in a sing-song voice, holding the vibrator at an angle so he could slide his finger in beside it. Sam's hole sucked it in greedily, and Sam moaned desperately at the added sensation of Dean's thick and calloused finger thrusting inside of him alongside the vibrator.
Dean crooked his finger just right, and he felt it against the tip of his index finger — the spongy surface of Sam's prostate. Making sure the vibrator stayed where it was, Dean stroked the pad of his finger firmly over Sam's prostate, massaging the surface without stopping. Sam was gasping for breath, writhing against Dean's hand, and his dick was turning a dark red from the treatment he was getting, looking as if it would spill over at any moment.
"Ah, Dean, please, can I come?" Sam got out between moans. "I've been good, right?"
Dean nodded in agreement, pressing a gentle kiss to Sam's mouth even as he kept up the overwhelming stimulation to Sam's hole.
"You've been so good, baby boy. You're perfect. Come for me."
As soon as Dean finished his sentence, Sam threw his head back with a whine and came, splashes of come streaking his own tummy and some of Dean's shirt. Dean left the vibrator in as Sam came, milking his orgasm until tears formed at the corners of Sam's eyes and he was gasping for breath. Finally having pity on him, Dean clicked the button off and slid it out of Sam.
Breathing heavily, Sam collapsed back into the pillows, grasping at Dean's clean hand with his own and lacing their fingers. Dean used his other hand to grab Sam's shirt and wipe them both down with it, cleaning up most of the mess. Sam was too fucked out to complain, which was truly a feat.
After a few minutes, Sam suddenly looked contrite.
"What about you, Dean? Let me..."
Dean stopped him, smiling sheepishly and gesturing to his pants, where a dark spot was visible.
"Not necessary, Sammy."
"Oh," Sam said with a pleased smile. "C'mere then."
He pulled Dean's arm until Dean was lying beside him, and Sam rested his head on Dean's chest.
"That was incredible, Sam. I didn't know you had it in you."
Dean twirled a strand of Sam's hair in his fingers. Sam looked up at him and laughed.
"I might be wilder than you think. I did go to college, after all," Sam said cheekily.
Dean smirked.
"I can't wait to hold you to that."