Work Text:
It caught him by surprise. They weren’t big on PDA. Not when they were out and about. They were brothers after all. So, it startled him when a big, warm hand settled on his thigh while they were in the middle of nowhere driving off to nowhere in particular.
Unexpected or not, unprompted or not, Dean lit up from his brother’s hand on him, like always. It was automatic. His body buzzed. A hum passing down his spine straight to his core. His body warming to Sammy like he was Dean’s own personal sun. Dimples and all.
Sam didn’t say a word. So Dean, being the awesome older brother he was, respected the silence with a smile on his face. He turned up the music and just drove. Life in this moment was good. Blue skies above, the road straight ahead, Baby purring under him, and Sammy riding shotgun. What more could a guy ask for?
For awhile they rode like that, but then his brother’s hand started drifting up his thigh to less family-friendly places. Higher and higher. Places that were too intimate to be anything but come-ons. Massaging his inner thigh. Dean smirked, nodding his head as he caught Sam’s eye and served him a knowing brow wriggle. He licked his lips.
Sammy always looked good sitting next to him. Whether he was in a fed suit or flannels. Bloody from a fight or spruced up for the job. It almost didn’t matter as long as he was there, alive. He looked even better with that certain glint in his eyes.
Dean’s gaze switched back to the road and he lowered the volume on the radio anticipating some talk. Sam loved to talk. Or at least, he loved making Dean talk. Either way, with the heat Sammy was sending his direction just from his eyes? Dean shivered inside, his motor warming up.
But Sammy didn’t make a peep before getting things started for real. His giant hand landed square on Dean’s crotch and he gave his pussy a squeeze like he owned it. Dean sharply breathed in through his nose. A fire burst to life inside him, his libido very much revving to a hundred in the blink of an eye. His pussy throbbed and Dean chuckled, grinning from ear to ear.
This was all very straight fucking forward for Sammy. Right to the point. No wasting time talking about feelings, no annoying questions. Just Sammy taking control. It made his pussy tingle.
“Dude…” The bastard had the gaul to shrug like he wasn’t doing anything. Oh so innocent. The little shit. A smirk hiding in the corner of that delectable mouth of his. Dean draped his arm on the seat back and let Sammy have his fun. Just having Sam’s paw cupping him over and over through his jeans was a fucking treat!
He started getting wet real quick.
Dean blushed. He had always been a little too easy. Even before he got on T. When people thought he was a chick they had always thrown out words like ‘cheap slut’ and ‘whore’. But damn when he became a man and started chasing tail like all the other guys, suddenly his horny ways were something to take pride in. His womanizing proof of his transition. His acceptance in the boys club.
At this moment though, he didn’t mind being easy. He didn’t care if this made him a man-slut or not. Sammy started groping him and he spread his legs wider. No questions asked. How could he do anything else? After everything they’d been through? After he knew what life without Sam was actually like?
No, sir. He had to gulp these good times down like shitty beer at a frat party until he drowned in them. Nobody knew when the shit would hit the fan, but with their lives it was basically a guarantee that it would. So Dean opened his legs wide in the cramped space of the bucket seat and let his baby brother do as he liked while he gently rocked his hips up. Rubbing up on Sammy’s hand like a cat against a pole.
The meat of Sam’s wide palm ground down on his engorged t-dick while those long fingers alternately cupped his pussy or drummed against his lips like he was tapping out Morse code. G E T W E T F O R M E STOP G E T W E T F O R M E STOP G E T W E T F O R M E….
Dean could feel the heat building in his core, his wetness starting to trickle out. He couldn’t help but hump his brother’s strong and very welcome grip. “Sammy…” he sighed. His eyes flicked back and forth between his little brother and the road over and over. Waiting for the next step. The next sexy-time shoe to drop.
“You good, Dean?” Sam asked with a straight face. Like he wasn’t openly toying with his older brother’s pussy while they were out on the road where conceivably anyone could see.
With a witty retort at the ready, Dean opened his mouth only for Sam to press his fingers down firmly into the seam of his pants. Right where Dean was needing him. He groaned. The big brain words flying straight out of his head in an instant.
“Smartass,” he panted, instead. His hips squirming uncontrollably. He swatted his brother’s nearby shoulder and grinned as Sam smiled back. Bright and easy. One of his genuine smiles that made his dimples pop out and his cheeks go all adorably pink. How could he be mad about that?
It made his heart melt into goo seeing Sammy so at ease. So carefree. So happy. Here with him. His Sammy in a good mood. A fun, sexy time mood. It was a thing of beauty and he might never get enough of it.
Dean patted his brother on the chest to get the message across that he was very much into this. While there his hand gave Sam’s pec a playful squeeze and his little brother’s chest popped under his palm. The movement of the muscle visible even through Sam’s shirts.
Sammy had a set of man tits on him that just didn’t quit. Thick pads of hard won muscle that suited him. They were certainly bigger than Dean’s tits had ever been. Plus they were lots of fun to grab and play just like a chicks.
Under his breath, Sam snorted and swatted Dean’s arm away from him. “Come on, Sammy,” Dean cajoled. “Turn about’s fair play and all that crap.”
Amused and trying to pretend not to be, Sam withdrew his hand. Dean groaned a little too loudly, his pussy dripping now and a lot chillier without his baby brother’s body heat. Sam shook his head, chuckling softly as he freed the tail end of Dean’s belt then singlehandedly undid the buckle in one fluid motion.
It was a display of self assured, competent manhood that made Dean’s whole body zing with arousal. He’d been known to pull the same stunt himself with chicks he bagged, but it was undeniably hotter being on the receiving end. Watching his little brother pull those same strings. “Oh, hell yeah, Sammy,” he crowed. His chest puffing up with fraternal pride.
“Dude, shut up,” Sam muttered while fighting down a grin. In seconds, the button and zipper of Dean’s jeans were dealt with and he was sitting in the front seat of his car with his pants undone like a blue collar dad on TV. Fresh home from work, manspread all over the family couch. All he needed was a beer in his hand and a hand down his—
Yep! That was Sam’s huge hand trying to worm under his clothes to get at him. Those blunt fingers digging to and fro to get at his pussy. He was proper wet now, his boxer briefs clinging to his skin. Then Sammy got there and Dean moaned, full throated, feeling his little brother’s gentle but insistent fingers. They got under his trousers and traced the contours of his lips through the thin, damp cotton of his underwear. It made his whole body shudder in the best way.
“Holy shit!” Dean’s arm jerked back to the wheel to take full control of the car again. His ten and two had gotten sloppy there from all the sexy vibes. He’d forgotten for a second what a fucking menace Sammy could be.
“You’re so wet,” Sam remarked like he had no idea what he was doing. What his wicked right hand was doing. Sammy teased his t-dick, lightly stroking along the short length of his engorged member in such a way that had Dean sucking in air loudly through his flushed cheeks and slack jaw. He blinked hard and growled a couple times to keep his focus on the road while his brother kept up his naughty distraction. “What’s got you so excited, Dee?”
“Cocky bastard,” Dean mumbled along with some other choice expletives. Unphased, Sam laughed like he was having the time of his life. Dean fought down a reciprocal smile, but the corner of his mouth tilted upward nonetheless. He moaned, low and quiet, as Sam’s fingers went spelunking under the elastic waistband of his boxer briefs.
Dean stuttered over a moan, his knuckles briefly going white on the steering wheel. The vinyl crinkled under his tightened grip. His stomach quivered. His bowed thighs squeezing together—or trying to at least as two of Sam’s calloused fingers tapped his wet pussy then slid right in. Hitting that sweet, sweet curve.
“Fuck! Sammy!” Baby swerved for just a second before Dean righted her, his face burning hot. He could feel his brother’s eyes on him. Intense and hungry like an embrace. He had to fight to keep his gaze away. To stay focused on the black pavement instead of his naughty little brother or he’d burst into flames.
Then Sammy really started moving. Hitting every pleasure button he could find in Dean’s hot, tight cunt.
“Sonofabitch,” Dean huffed, arching into his brother’s hand again, skin against skin. It was electric. His eyelids fluttered shut in a flurry of pleasure and he had to bite his lip from letting out some truly embarrassing noises.
“You should keep your eyes on the road, Dean,” Sam tutted, sounding like a disapproving school mom.
“And you should keep your weird, freaky hands to your-fucking-self,” Dean shot back. He swallowed hard and forced his head down. Glaring at the road rather than ogling his brother’s flippant expression.
“Do you want me to—“
“No!” In a flash, Dean slammed his legs shut. His left hand shot away from the wheel and latched onto his brother’s thick wrist to make sure Sammy stayed put. If he could drive while he was bleeding out, then he could absolutely do it while getting finger blasted by his younger brother. He moaned, pointedly arching into his brother’s blunt fingers, clutching at them, pulling them deeper with his walls. He wanted Sammy in him as far as those ridiculous giant fingers could reach. “I ain’t no quitter.”
“I know,” Sam murmured, his voice mild, but sharply arrogant at the same time. He curled his fingers so expertly Dean trembled, his voice shaking as he coughed to cover a whimpering moan. Sam wasn’t fooled, though. He knew all of Dean’s weak spots. Always had. Better than anyone else Dean had ever banged.
With his fingers digging for buried treasure, Sam added more pressure to Dean’s relatively big, reddish t-dick with the flat of his palm. Dean bucked into that roughened skin, squeaking, in a manly way, while coming to the crest of a small but powerful orgasm. His legs cramped a little. Baby drifted again for half a second before Dean forced it back. Reaffirming his ten-and-two position yet again with a mumbled growl.
But Sammy didn’t stop. How such a big clumsy dork could be so dexterous was beyond Dean’s comprehension, but he nearly cried in exaltation as Sammy worked him over like a beast. Putting the bang in fingerbanging quite literally.
At one point, Dean had to slam on Baby’s brakes, when a bigger climax punched the air out of his lungs. His legs jerked out of his control. His cunt clenching around his brother’s thick fingers as he came big time. He creamed his briefs with his head thrown back as he yelled his brother’s name in ecstasy.
Beside him, Sam caught the back of the seat with his free hand and then spun back to make sure no one was speeding towards them. They hadn’t seen anyone else in a long time but it paid to be aware if not exactly cautious. The coast was clear, so Sam let his brother catch his breath.
“Jesus, Sammy,” Dean muttered, eventually once his vision had cleared. He grinned, sloppy and boneless like an fuck-drunk idiot. Sam’s arm lifted for a second like he meant to pull out and Dean brought his right hand down this time. He lightly gripped his brother’s wrist.
“Stay,” he whispered, his expression sobering. A new blush rising all the way to the tips of his ears. The vulnerability made him twitchy. The mind blowing orgasm didn’t help matters in that respect.
Nodding, Sam unbuckled his seatbelt and scooted closer to his sex lazy brother. His dick a solid, blatant line in his jeans. He brought his other arm up and caught the side of his brother’s neck in his hand. His thumb traced the bottom of Dean’s solid jaw, his gaze stuck on those plush, slightly chewed up lips and then he leaned in. Dean’s eyes rolled shut, his brother’s name a breath exhaled between them as Sam pulled him in for a kiss.
Gentle at first. A soft press of lips. A tentative sweep of tongue at the front door. Dean opened up right away and wham—the floodgates opened.
Suddenly, Sam was demanding, stealing the air straight out of his lungs. Dean whined into his brother’s mouth. His head almost dizzy while Sam’s fingers kept prodding him, coaxing him along, not letting up for an instant. Like a beast trying to burrow their way to their prey from every possible angle.
In pretty short order, Dean’s pussy convulsed around Sam’s fingers in yet another, smaller climax while they made out in the literal middle of the road. But Sam was relentless. He rested his forehead on Dean’s and smiled as he kept fingering his older brother. “I’m not done with you yet, Dean,” he declared in that husky, brook no argument tone of voice. “I want to see my big brother shoot his load.”
“GoddamnitSammy!” Dean tingled from the crown of his head to the ends of his toes. His knees bounced, legs jittery with the too much-ness of it all. He never could resist when his sweet, little brother took charge like this and he wasn’t about to shut it down now. Sex with Sammy was just too good. He squeezed his eyes shut and nodded. Whatever Sammy wanted…
“The seats—“
With a huff, Sam shifted back towards his side of the car, leaving Dean chilly and pouty for a minute. From out of nowhere, in the small space between the door and the seatbelt Sam produced a towel. The towel they kept to protect the seats while banging chicks in the backseat. “Already covered.”
“That’s my boy,” Dean chortled. “You’re like a Boy Scout. A sexy Boy Scout.”
Sam rolled his eyes and slipped his wet fingers out of his brother. Dean sighed, sad to let them bad boys go, but still eager. Dean lifted his hips off the seat and pushed his jeans and briefs down while Sam shoved the sex towel under him and sucked his come-covered fingers clean. Dean sat his bare ass on the scratchy cotton and groaned watching Sam taste him so hungrily. He lightly massaged his t-dick with the pads of his fingers. His thighs wet practically down to his knees. “You owe me a new pair of briefs,” he quipped, flippant even while his pussy and t-dick were tender in that pleasant fucked-out way.
“I already bought you a whole new pack. They’re in my duffel,” Sam replied in a level, put-upon voice.
“See?! You are,” Dean teasingly insisted. “A very sexy Boy Scout.”
With a sniff of injured pride, and a certain amount of smugness, Sam shifted over to his brother’s personal space. He craned his head low and Dean hissed as teeth and a pair of suctioning lips latched onto his neck in the exact right spot. The one below his ear that always made his left leg hitch and his pussy throb. Meanwhile, at the same time three long fingers slid into him with absolutely no resistance. “Sammy, baby,” he muttered like a prayer from a broken man.
“Drive, Dean,” Sam ordered.
Obediently, Dean gingerly put his foot on the gas. The Impala rolled back into motion as if nothing had happened and they continued on their way.
They picked up speed and Baby did too. Dean trembled, barely able to keep his eyes open and on the road while Sam marked up his throat good. Harsh red love bites dotted his neck the next time he peeked at the rear view mirror. He looked wrecked. His gaze suitably empty for a man that had just come four or five times. Dean sagged against his brother, relishing the closeness they so rarely allowed themselves.
“My big brother taught me everything I know,” Sam whispered, in his ear. Dean gasped then whimpered. His already overstimulated cunt spasming. His heart was rocketing against his ribs, his pussy gushing with liquid fire as his insides shook and collapsed. He couldn’t breathe, but as long as he died in Sam’s arms he didn’t fucking care. “I’ve got the smartest, sexiest, most badass big brother in the whole world.”
“Sam—“
“He’s the best guy I know,” Sam said, with total sincerity. “He’s my hero.”
Punched in the gut, Dean shook all over as he squirted. Thick watery globs of come gushed out of his cunt in arcs that splattered onto the towel under him as well as his jeans and underwear and the footwell. At this rate he was going to have to replace them all, but at the moment all he cared about, all he could think about was his gorgeous, devastating little brother.
Quick as a whip, Sam’s cock was out of his pants and he was jerking off using Dean’s wetness as lube. Dean slowed Baby to a gradual crawl as Sam shot his load all over Dean’s hot, aching pussy. Dean groaned, feeling the warm jizz splatter on his thighs and land in his bush, seeping and drizzling onto his pussy lips. Yet he had never felt more like a man. A man’s man. His brother’s man. The most important, most beautiful, most brilliant, most kindhearted man he knew.
In short, Sammy was simply the best.