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When Sam was fifteen, he liked watching Dean getting lucky.
He didn’t consider it that fucked up, at the time. Sam didn’t even think it had to do with Dean himself, really; he just knew that he admired his older brother in everything that he said and did, and Sam himself was hopeless when it came to flirting or charming anyone. So of course it made sense that he took pleasure in watching how effortlessly Dean could seduce a stranger into his bed. Or the back of the car. Or an alleyway. Or wherever.
They were staying in a tiny town in the corner of Missouri nearest Lawrence, and Sam wanted to move on--or at least go back to Kansas, where he felt a little more at home. But Dad had wanted to see an old friend, neither Bobby or Pastor Jim had been free to watch them, and Dean had said they may well enjoy the scenery.
Which, it seemed for Dean, meant a local newspaper journalist’s pretty daughter, Cassie.
Sam hadn’t meant to see them together; he’d been walking back from the library (why did small towns have to have bad libraries? Books shouldn’t be that hard to get) to their hotel when he spotted the Impala. He’d moved toward it, thinking about seeing if Dean was around to drive him the rest of the way; but he was drawn up short when he realized that Dean was in the car, and he wasn’t alone in the front seat.
He’d seen Dean touching girls before, had seen him kissing them. Sam was well-aware of how it all worked. But maybe it was the fact that he’d never seen a girl like Cassie, with her creamy brown skin and long, frothy crimps of mocha-colored hair. She looked so lovely pressed against Dean, like coffee and creamer swirling together, and Sam had been momentarily mesmerized, watching the way Dean had her up against the passenger-side door, hands invisible to Sam but lips working expertly over her throat.
From the way her head was tipped back, mouth open and eyes fluttering, Sammy suspected he knew exactly where his brother’s skillful hands were. And for the first time since he’d begun sneaking peaks of Dean and his conquests, the younger boy had found himself jealous.
Of what, he really wasn’t sure. He’d never had that kind of longing for Dean before, and Cassie wasn’t that different from other girls he’d caught glimpses of Dean pleasuring. But without rhyme or reason, in that moment, Sam had wished desperately that he could be right there, listening to the way that Dean was making her pant and gasp out his name.
He’d spent the next two nights jerking off thinking about it, closing his eyes to picture the way Cassie had looked, and the slow roll of Dean’s shoulder as his hands had moved on her, fingers inside of her, making that beautiful girl moan for him.
For all the times that Sam had watched his big brother make girls swoon or sweep them off their feet--usually onto the nearest horizontal surface--he’d somehow never realized that Dean was a whole lot sharper than Sam gave him credit for, and that he was well aware of his little brother’s attention to his actions.
But he caught on to that fact real quick, when he returned to the hotel room three days later and opened it to find Dean and Cassie sprawled on the bed that Sam had been sleeping in--Dad had splurged and gotten adjacent rooms, which meant that the boys each got their own bed without having to resort to a creaky pull-out couch, or a camping cot.
Cassie’s shirt was unbuttoned just far enough to reveal her bra, which was just barely succeeding in containing the full swell of her tits, and her jeans were open, giving Dean’s hand space to tuck in under her panties. Sam could see the crimson elastic band of the thong she was wearing, straining over the back of his brother’s hand as it moved leisurely beneath the fabric.
“Fuck--sorry,” he stammered, red-faced and starting to retreat, but then Dean spoke, not turning his face from where he was mouthing gently over her collarbone. His voice was so calm, so sure.
“Shut the door, Sammy, and lock it, would you?” Cassie made a sharp, pretty noise at something his fingers were doing, and Dean chuckled. “Saw you the other day, Sammy. Standin’ there watching us in the car.”
Sam stilled, staring at his brother’s back, torn between confusion, shame, and the unavoidable reality that the sounds coming from Cassie’s mouth were were getting him hard. His cock was beginning to strain against his jeans, his breath coming faster and shorter, and Sam felt spotlit when her liquid brown eyes slid to him past Dean’s shoulder. Cassie’s lovely full lips tugged up in a smile.
“Dean, he looks scared,” he murmured, and Sam realized he hadn’t heard her speak before. Her voice was even prettier than her moans, if that was possible, soft and musical and sweet like honey water. “You gotta be gentler with him, big guy.”
Dean huffed a laugh, stopping his hand and turning to look back at Sam, his green eyes dark and hungry. “We’d have invited you to join us then, but Cassie had to get home. She’s got all night, this time ‘round. Figured we’d see if you wanted a taste, considerin’ how into it you looked hangin’ around outside the car.”
Sam finally found his voice, though it was choked and quiet. “You weren’t--you aren’t mad at me?”
Both of them smiled, and Dean withdrew his hand, making Cassie murmur in protest as she sat up, sliding back to sit against the headboard with her clothes still shamelessly in disarray.
“Hardly,” Dean replied. “Hell, Sammy, I knew you liked watchin’ me hook up, but I thought it was just a voyeurism thing. I’ve never seen you look half as hungry as you did three days ago. You looked so ready to climb into the car with us and get your mouth on her...” Dean paused, watching Sam flush and stutter in response, and then raised his eyebrows. “Was it Cassie you were eyein’? Or were you thinkin’ about touching me , Sammy?”
The younger boy’s mouth snapped shut, eyes wide and unsure, because he honestly did not have an answer to that.
Cassie was quiet when she interjected. “Dean, go get him--you got him shakin’ like a leaf, baby.”
Nodding, Dean slid off of the bed, padding toward Sam. He was barefoot, his jeans undone same as Cassie’s, his t-shirt rumpled from her fingers. Sam felt like a deer in headlights, a rabbit staring down a fox, and yet it wasn’t fear that paralyzed him so much as genuine uncertainty about whether or not he was ready for this.
When Dean reached his brother, he raised both hands, cupping Sam’s face between his palms. “Don’t have to be scared of me, Sammy,” he said quietly. “You know I’m always gonna take care of you, don’t you?”
It took him a long moment, but Sam finally nodded. Dean’s smile showed relief, and a sparkle of mischief burst back to life in his eyes; he lowered one hand from Sam’s face to take his hand, fingers twining with Sam’s and gripping tightly, not letting him doubt his older brother’s sincerity. “C’mon,” Dean said, and though his heart leapt into his throat, Sam just nodded, letting Dean guide him over to the bed.
“Do you wanna touch him, or me?” Cassie asked softly, her smile so tender and sweet it made Sam’s stomach knot up. He couldn’t think of an answer, because he knew which option was more normal, more socially acceptable--but he also knew which one he really wanted to say. Not that Cassie wasn’t drop-dead stunning, and Sam did want to touch her--but he wanted to ease into this, and start somewhere that felt more like home to him. With some one who felt more like home.
Cassie nodded, as if he had spoken his feelings out loud. “Thought so,” she purred, coffee-colored eyes twinkling. “Dean, help me out, here.”
They both moved in close, and Sam gasped soundlessly when he found himself sandwiched between the hard, familiar wall of his brother’s muscular body, and the soft, lilac-scented skin of Cassie’s chest. He could see the full shape of her tits, dark rose-colored nipples visible through the sheer black lace of her bra, and Sam’s cock leapt again, curious despite his confused inner desire. He’d seen plenty of tits, in porn and by watching Dean, but he’d never been this close.
“Don’t worry, you’ll get to touch those, too,” Cassie teased, and Sam blushed, but managed to return her smile shyly. “First, though, we’re gonna try something, sugar,” she went on. “I can see what you want, but I bet you’re scared, thinkin’ it isn’t okay. Cause he’s your brother. Right?” At Sam’s wide-eyed nod, Cassie chuckled. “I’ve got you, sweetheart. I’m gonna move your hand for you, alright?”
He didn’t resist, letting her take his wrist and gently guide it behind his back. Sam felt the heat of Dean’s abdomen through his shirt, felt the graze of the cotton, and then--then Cassie was easing his fingers down into the open V of Dean’s fly, and Sam gasped audibly as he felt no underwear serving as a last barrier between them. His fingers brushed over the hard curve of his brother’s erection, and Sam let out a tiny mewl of surprise--which he bit back instantly, in order to hear the noise that Dean made.
Sam had never heard anything even half as fucking beautiful. It was soft and wounded, needy, nothing like he was used to his big strong brother sounding like during his sexual encounters. “De?”
“‘M okay, Sammy,” Dean whispered, his lips next to Sam’s ear, and the younger boy closed his eyes, savoring the warm brush of his brother’s breath against his skin. “Just feelin’ it. Always knew you’d have soft, sweet hands.”
Sam opened his eyes, narrowing them in determination, and he caught the knowing smirk on Cassie’s face as he pulled away from her leading touch, pushing his hand more firmly down and grinning a little, himself, at his boldness. Dean groaned in surprise as Sammy’s hand closed around his hard-on, giving it a curious, exploring squeeze.
“‘S so hot,” he murmured, and Cassie nodded, lifting one hand to trail her fingertip along Sammy’s jaw. “Is it--always? Or just ‘cause he’s still got his pants on?”
“Always,” she replied. “When it’s hard, anyway. Your big brother runs hot, sweetheart, he’s a furnace when you get him all riled up. Do you wanna see it, or just keep touching him like that?”
Sam chewed on his lip a moment, then smiled a little more shyly. “Am I allowed to kiss you?”
“Oh, little Casanova’s getting the hang of this,” Dean laughed from behind him, and Sammy squeezed his fingers in retaliation, triumphing in the muted groan of surprise which that elicited. “Sneaky bitch.”
“Jerk,” he retorted happily, and then gasped, the sound vanishing instantly into Cassie’s lovely, plush mouth as she kissed him, licking teasingly at his lips until Sam admitted her tongue, moaning softly as she masterfully claimed his mouth.
It wasn’t his first kiss, of course, but it was the first time he’d been kissed with such assurance, or such confidence. Little Amy Pond had been sweet and shy, her lips soft and uncertain as they’d sat on her living room sofa and fumbled forward.
Cassie had no such reserve; she kissed him like she wanted to taste Sam’s very soul, and he felt as if he was being activated somehow, his hand growing more sure in its stroking motions, drawing another long, throaty moan from Dean as Cassie puppeteered the younger Winchester with her hands and mouth.
“Careful, sweetheart, gonna make me jealous,” Dean teased from behind him, and Cassie broke the kiss to glance past Sam, her chocolate eyes glittering with amusement.
“You’ve had plenty of my kisses, big guy,” she retorted. “Besides, Sammy tastes sweeter than you do. Maybe I like kissing him more.”
Sam snorted at the unlikelihood of that, and behind him, Dean let out a little hum. “Well, don’t go hogging all the sugar,” he said, and Sam stilled, fingers stuttering in their movements as he tried to determine just what Dean meant by that.
“I’d never,” Cassie shot back, smirking. “Here, Sammy, turn a little bit for me.”
He let her cup his jaw, moving his face in an arc until--Sam’s eyes widened as she kept him where he was, one hand working slowly inside of Dean’s jeans, while she guided his mouth around to meet Dean’s.
For all of his spying, Sam had never actually let himself actively imagine kissing his big brother.
Dean’s lips were far softer than Sammy had expected they would be; somehow, he had assumed that the older boy’s mouth would be as hard and fierce as the man himself was, sharp and wild and biting. But to the contrary--Sam let out a soft whimper, surprised at how sweet and gentle Dean’s mouth was, almost equal to Cassie’s in the tenderness of the kiss. For a moment, Sam felt as if he was suspended in time, not even sure whose hand was cupped around his jaw.
When they broke apart, Dean’s eyes were open, centimeters from Sam’s own and locked on him with an intensity that Sam had never seen in them before. “De?” he whispered, uncertainly.
A smile curved up his brother’s lips--those lips that Sam had just been kissing--and the older boy nodded, dropping his hand--there was still warmth, Cassie’s fingers were still there, Dean’s hand had been cupping his cheek over hers--and chuckling. “Damn, Sammy. Had no idea you’d be that good. You been kissin’ a lot of people?”
Sam shook his head, smirking faintly. “Just one girl. Before this, I mean.”
“Lucky girl,” Cassie purred teasingly, and when Sam looked back at her, she grinned and dropped another quick peck on his lips. “You’re neglecting him now, Sammy,” she whispered, and Sam blinked, remembering, looking down at where his hand was now still inside of his brother’s jeans.
When he resumed his movements, Dean growled softly, and Sam didn’t think he had ever heard anything so gorgeous. It was better than the little moan Dean had made when they kissed, and he knew why without overthinking it. It was a sound of possession and need, a dark, gritty sound, and it was utterly and completely Dean .
He felt them moving, all three together, and Sam simply followed their lead, trusting the other two to guide him. Dean was leaning back now, resting his weight on his hands against the mattress, and Cassie’s hands were sliding delicately around Sam’s torso, steadying him as he continued stroking his big brother’s dick. Sam watched, eyes dark and hungry; and then he moved, twisting until he could kneel facing Dean directly. Cassie stayed put, now behind him, and leaned in until Sam could feel her long, curly hair tickling the side of his neck as he looked down, taking in the full view of his hand moving over Dean.
“It’s lovely, isn’t it?” Cassie breathed in his ear, and Sam could only nod in agreement. “Wait till you see it without his pants on. Your big brother is hung , sugar.”
Sam moaned, unable to help it, and Dean grinned up at him, green eyes glassy and dark. “You wanna see it, Sammy?” he asked, low and breathless. “Wanna watch Cassie suck me?”
Sam licked his lips, considering. “Yeah, but--but I don’t want you to come yet,” he said, boldly, and Cassie giggled, soft and lovely. “Please?” Sam added, unsure if he’d crossed a line with his request.
Dean surged up, dislodging Sam’s hand from inside his jeans as the older boy leaned in, catching Sam’s face with his palm and tugging him for a hard, deep kiss. “Course, baby boy,” he whispered against Sam’s lips. “She’ll just get it nice and wet, let you see how pretty it looks. ‘S what she did right after you slunk off the other day, when we were in the car...I fingered her till she came, and then she sucked me off. Wanna let you see that part.”
Sam shuddered at the filthy words, and he let his mouth run without his permission, carrying on the bold pattern since it seemed to be getting him good results. “Can I--see the first part, too? Can I watch you finger her till she comes?”
Cassie let out a low, appreciative hum. “I like how gentlemanly Sam is. Can he, Dean?”
“Course he fuckin’ can,” Dean shot back, laughing as he nudged Sam back onto his ass, and turned to face Cassie, rolling up onto his knees. “He’s gonna see all three of us come, with whoever’s hand or mouth involved that he wants.”
Sam whimpered at that idea, his hand jumping to squeeze his own cock helplessly. “Seriously, De?” At Dean’s smirk and nod, the younger boy swallowed roughly, his mind racing ten miles ahead of itself. “I...I think--I’m not sure. I want you to get C-Cassie off,” he said, just barely avoiding tripping over her name as he said it. “And--for you...”
“You’ll get Dean off yourself,” Cassie interjected, leaning over to kiss his lips once more, quick and light. “I’ll just enjoy the show when you two get down to it. But for now...lemme show you how damn pretty your big brother looks when he’s got a mouth wrapped around his dick.”
Sam nodded at once, scooting back until he was braced against the heap of pillows piled against the headboard. As he watched, Cassie rotated back to meet Dean, who was still kneeling upright; as she crawled closer to him, her face was only just higher than his cock where it was bobbing lightly against the older boy’s belly.
Cassie wasn’t slow, or shy; she didn’t move like she was uncertain about how to proceed, the way Sam knew he would have in her place. Planting her weight evenly across her hands and knees, she dipped down, and Dean tangled his fingers into her thick hair, holding it back both for her convenience, and to let Sam have a clear view as Cassie’s lips parted over the head of Dean’s cock, and then sank down, until she had engulfed the entire length of his shaft in her mouth.
Dean groaned softly, head falling back as he bucked leisurely forward into her mouth. Sam watched, entranced, mesmerized by how different and yet how similar Dean’s body seemed to be compared to his own.
The older boy’s cock was longer than his--whether because of his older age, Sam couldn’t be sure, but it hardly mattered--and about the same girth. It was darker than his, swollen and throbbing with blood, and Sam let out a low, longing sigh as he watched Cassie masterfully work her way around the glans with her tongue.
His brother’s gaze slid over to him, and Sam’s teeth clamped around his bottom lip, trying to remember how to force oxygen into his lungs as Dean looked at him like that--like Sam was something he wanted to devour alive. And for the first time in his life, Sam felt absolutely no reservations or fear about allowing that to happen.
Cassie pulled off with a noisy, wet slurp, turning to look at Sam over her swollen, shining lips. “You want to get a taste of him, sweetheart?”
Sam’s eyes widened, and he looked from her to Dean, who merely grinned knowingly. “She ain’t kidding, baby boy. You’re part of this. But only if you want to,” he added, some of the lust evaporating from his gaze as he refocused on Sam, and his wide, anxious eyes. “You don’t gotta do a damn thing you don’t wanna.”
“I want to,” Sam jumped to assure him, rolling back up onto his knees, and scooting forward inch by inch. “I just--I’ve never done that . Only--only fooled around with a girl, before.”
“Good thing you got me, huh?” Cassie responded, her chocolate eyes twinkling. “I’m the master of teaching sweet little things like you how to suck dick like a ten-dollar whore.” Catching the bemused look that Dean shot at her, Cassie snorted. “Don’t worry--Sam’ll be worth a hundred before I’m done with him.”
Sam sidled in a little closer, and Cassie reached out, sliding one hand around the smaller Winchester’s waist and the other into his hair. “C’mere, baby,” she purred, shifting to kneel behind him. “Dean, lay your ass down, make this easy for him.”
Dean complied at once, falling back onto his ass and propping himself up on his elbows, raising his eyebrows teasingly. “You actually gonna let my baby brother put his mouth on me, Cass?”
“When he’s ready,” she shot back. “Sam, you ever even touched someone else’s dick before? Besides what we just did, I mean.” When he shook his head, eyes still locked on his brother’s groin, Cassie slid her long, lovely brown fingers down to his hands, guiding them to Dean’s thighs. “We’re gonna take this easy. Tease the man a little--he deserves that, don’t you think?”
Sam smirked, turning to look at her sideways. “I’ve never seen anybody tease him for long before he makes ‘em regret it.” Dean punctuated that with a smug little laugh, and Cassie narrowed her eyes at him, but didn’t respond. “If you can teach me that, though, I will delight in the skill, and use it to my full advantage,” Sam added, giving Dean a mischievous, smug smirk of his own. “I’ll make him suffer.”
“Fuck, Sammy, listen to you,” Dean growled. “When did you jump from my shy, voyeuristic little brother to a dirty mouthed little slut?”
Sam nearly managed to keep his composure through Dean speaking, but at the final word, he gasped, jolting slightly and shivering with raw delight at the naughty sound of it. He’d never been called a slut before--he’d never been a slut before. But the sound of it burned through him like molten lava--not just the word, but the way it sounded in Dean’s voice. Hot and dark, potent, better than any of the alcohol that Dean had ever snuck for him, better than the one time in his life so far that Sam had experimented with weed.
And the way that Dean looked at him, seeing that shudder, and seeing the way that Sam’s eyes darkened and widened, he knew that his brother saw right through his attempt to recover.
“Oh, you liked that, huh?” Dean purred, trading a smug look with Cassie. “Who’d have thought that my sweet, shy, darling little brother Sammy would have a kink for dirty talk? You like being told how naughty you are?”
Sam huffed, lifting his head and sticking his tongue out at his brother. “I wouldn’t know. The girl I kissed before--she was really sweet and shy. Not the dirty-talking type.”
Dean’s hand flew out, his fingers sliding beneath Sam’s chin and his thumb catching just inside of Sam’s parted lips, pressing the pad down onto his tongue to pin it flat. “Her loss,” Dean growled. “The way you’re blushin’ right now, pretty sure I’ll be spitting out some filth whenever possible just to get those rubies back in your cheeks.”
“Enough talking, more dick-sucking,” Sam managed to grunt back, dislodging the finger in his mouth. “I got some learning to do, right?”
“Right,” Cassie said happily, carding her hand into Sam’s hair and giving him a gentle little push downward. “You have much to learn, young padawan.”
“Oh my God, you’ve been around Dean too much if you’re making Star Wars jokes during sex,” Sam mumbled, but he lost interest in joking around when he found himself abruptly nose-to-head with his older brother’s cock.
It had been one thing to touch it; feeling the heat of it, the thickness and hardness of the shaft, knowing that what he was touching was part of Dean . But this--Sam had never, in his wildest dreams, imagined being this close to anyone else’s cock, let alone Dean’s . It wasn’t that he’d never thought about guys--he’d never really thought about anybody, not like this.
The reality was nothing like he could have envisioned.
“Give him a kiss down there, Sam, see if you like how that feels,” Cassie suggested, her fingers still gentle in his hair. Inhaling, Sam complied, parting his lips slightly and leaning in closer to press them lightly against the side of Dean’s dick, just below the smooth curve of the glans. Dean made that same noise again, the wounded one, like it physically hurt to feel Sam’s lips even brushing against the swollen flesh.
Getting bolder, Sam moved back over the head and tried in earnest, sinking his mouth down over his brother’s cock. He moved up and down carefully, closing his eyes against any distractions and simply focusing on what he could feel with his lips, and over his tongue. Dean was trembling, his thighs shaking enough to brush against Sam’s face and shoulders every few seconds, and if Sam let himself dwell too long on the sounds coming from over his head, he knew he would lose his mind and not be able to function at all.
Cassie’s fingers threaded into his hair again, and Sam drew up off of Dean’s cock to inhale raggedly and let her do what she wanted with him, letting his spine and shoulders stay limp and malleable.
She guided his head downward, and Dean grunted softly when Sammy’s breath brushed the base of his cock, and his lips grazed his balls. “Cass, he doesn’t know that trick,” Dean wheezed with a laugh, and Sam let out a low growl of objection.
Cassie sounded smug. “I think he wants to learn,” she purred, and Sam mumbled his agreement. She nudged again, and Sam let his head be moved. When his lips came into contact with the soft, swollen flesh of Dean’s balls once more, Sam didn’t hesitate, not wanting his brother to argue again.
He needn’t have worried; as his mouth closed around one of Dean’s balls, tentative but eager, the older man made a noise that was even richer and more needy than the ones from before, and Sam instantly knew that he liked these ones even more.
“Mmm, bet we could make a rimming champ out of this one,” Cassie murmured from above, and Sam made a questioning noise. He knew the word, had heard it in porn before, but he’d ever pursued its definition. Sam wasn’t sure what it meant--but if Cassie thought he could be good at it based on his current performance, he assumed he’d like it.
Dean chuckled, tugging gently at Sam’s hair to get his attention as the younger boy continued sucking and licking at his sack. “Rimming is like eatin’ a girl out, but on a guy,” Dean told him, and Sam raised his eyes as best as he could, tilting his head to one side to raise an eyebrow in question without stopping his current task. Dean smirked, green eyes dark and blazing. “It’s sticking your tongue in someone’s asshole, baby boy. Lickin’ ‘em out and makin’ ‘em feel good. Can do it on girls, of course, but pussy’s sweeter. It’s a nice trick with guys, though, since they ain’t got a cunt for you to lick.”
Sam pulled off with a wet slurp, gratified when Dean reacted with a shudder and a small moan. “I’ve never heard of that,” Sam said, and he couldn’t help his blush as he admitted it. “I mean, I thought I knew the word, but--people actually like that?”
Dean’s grin grew, wicked and filled with promise, and Sam bit his lip at the sight of that expression. He’d seen it aimed at waitresses in diners and girls in bars, but the full force of having it directed at him was almost overwhelming. “Maybe if you’re good, I’ll show you just how fuckin’ fantastic it feels,” Dean taunted him, and Sam could only grunt, his toes curling with want at the heat in his brother’s voice.
He blinked when Dean’s hands curved around his face, gently nudging the younger back away from him again, and when Sam looked up, Dean’s eyes were soft, though still dark with lust. “I don’t wanna get too close to comin’ just yet,” Dean told him. “Gotta save it.”
Drawing back obligingly, Sam smiled, licking his lips. “Is it Cassie’s turn?”
Dean’s eyes sparked, and he smirked back at his brother, cocking his head in order to glance at Cassie over his shoulder. “I can teach you how to eat pussy like a pro, if you want, Sammy,” he offered. “It ain’t too different from rimming, so if you like it, that’s something else I can show you later.”
Surprised, Sam turned back to look at his brother. “Have you--rimmed someone, before, De?”
That made his brother’s grin widen even further, and Sam could see a flicker of fond recollection in their emerald depths. “I’ve played the whole field, baby boy,” was Dean’s rather cryptic reply. “I love to learn, and experiment around.”
Feeling emboldened by the sudden desire to become as skilled as Dean was in the area of sex, Sam noded. “I want to.” He looked back at their female companion, his hazel eyes intent. “I want to learn to go down on you.”
She lay back at once, all soft lines and a Cheshire cat smirk. “Not a problem for me, sweetie.” She stretched her arms over her head, folding them around one of the pillows, and Sam couldn’t help thinking that she looked like some sort of medieval queen, pulled from the pages of an erotic novel. He watched as Dean crawled around him, moving to kneel beside her and beckoning Sam closer to them.
Cassie shimmied out of her jeans, leaving her only in the bright red thong, and Sam licked his lips as his mouth went suddenly dry. He could see already, even from further down the bed, that her pussy was glistening wet through the sheer lace of the garment.
He couldn’t help thinking that she looked like a blossoming flower, despite the cheesiness of the comparison. Maybe Georgia O’Keefe hadn’t been so far off, after all. Sam smiled inwardly, wondering if he could wrangle an A out of writing an essay on her very sensual metaphorical artwork, now that he understood her perspective a little more clearly.
Dean’s voice was quieter now, breaking through Sam’s thoughts and bringing him back to the present. “Pull the thong aside, Sammy. Get a good look at her.”
Sam did so, hooking his index finger into the elastic hem and drawing it aside. Cassie shivered slightly as the air conditioning at teased, and Dean spoke again, merely a whisper now. “You should give her a kiss, baby boy. Just like you did for me.”
Sam leaned in, and he pressed a sweet kiss to the smooth-shaved mound of her pussy, just above the point where her lips parted to reveal the hooded bud of her clit. She was warm, so warm, and Sam inhaled deeply, able to smell the sweetness of her body.
“Explore her a bit,” Dean whispered, neither a command nor a suggestion--just a thought. Still, Sam obeyed his brother at once, feeling entranced by the body spread before him, swept up completely in the spell woven by his big brother, and the lovely mocha-skinned siren sprawled between them.
He was being shy about it, Sam knew he was, tentative when he dipped his face further down and slowly dragged his tongue up the length of her slit; but Cassie’s full-bodied shudder of pleasure was affirming enough to make Sam feel bolder with every second.
Remembering something he had read about female pleasure in his wandering self-education via the internet and libraries, Sam sought out the hardened nub of her clit; once he’d found it, he closed his lips over it, sucking lightly.
Cassie cried out softly, thrusting up against his face as he worked, and Sam’s gaze leapt to his brother’s face, seeking confirmation that he was getting it right.
“Perfect,” Dean praised him, and Sam blushed with delight. “Keep on doin’ that, Sammy. I’m gonna get my fingers inside of her. We can get her off together, how’s that sound?”
Sam nodded hungrily, and he scooted a little to allow Dean to get closer to him, down between Cassie’s spread legs. He watched his brother suck two fingers into his mouth, wetting them, before he reached down to slide them over and around her entrance. Cassie’s hips arched up at once, and Sam watched in awe as Dean pressed his hand forward, both fingers sinking smoothly into her pussy without resistance.
Cassie moaned, long and low and sweet, and Sam bit his lip again, nearly breaking the skin as he listened to her. “Fuck, she sounds so good, De,” he whispered, and when he looked back over at Dean, the older boy leaned in and kissed him again, agreement written in the hard press of his mouth against his brother’s.
“Give her clit some more attention. She’ll be coming for us in no time,” he promised, and Sam obeyed him, leaning in to resume his previous efforts with renewed vigor.
Cassie lost herself in it, bucking to fuck herself harder onto Dean’s fingers while simultaneously pushing up against Sam’s mouth as he sucked and licked at the glistening pink bud of her clitoris, and the soft, slick flesh around it.
Within minutes, she began gasping louder, and Dean let out a low rumble of approval just before she abruptly convulsed, her entire body spasming and arching up harder, higher; Sam lifted his head to watch in amazement as she climaxed, her entrance squeezing down around Dean’s fingers as if milking every possible ounce of pleasure out of the orgasm sweeping through her.
“That....was fucking stunning,” Sam breathed out, and Cassie let out a weak laugh, beaming up at him with a mixture of fondness and agreement.
“Glad to impress,” she murmured, fingers stroking aimlessly over her own bare skin. “Now, why don’t you pretty boys take care of each other, while I lie here and bask in the afterglow? Might even rub out another little one for myself, watchin’ you.”
Dean nodded, smirking knowingly as he moved slowly back from her. “C’mere, Sammy--it’s time I made a proper man outta you.”
Sam turned toward his brother at once, feeling curious and far more confident by now. Dean took both of his hands, guiding Sam forward up onto his knees and then turning him around; Sam blinked as he found himself on hands and knees, facing Cassie again. She was smirking, clearly knowing exactly where this was going, and Sam could only inhale sharply as she abruptly pulled him closer and kissed him.
He could feel Dean’s fingers at his waistband, undoing his jeans and guiding them down his hips, and Sam whimpered when he realized what was about to happen.
“Focus on me, baby,” Cassie breathed. “If you get nervous, just kiss me. He’s gonna look after you, okay? And I’m gonna help you."
Sam nodded, trusting her words blindly, and eagerly. The air conditioning in the hotel room was cool against his bare ass, but Sam ignored it, focusing solely on the soft way that Cassie’s lips parted to admit his tongue. She was teaching him without words, guiding him into kissing her back more skillfully, and Sam let it consume his attention, memorizing everything that made her moan for him.
When Dean’s lips grazed down the seam of his ass, however, Sam couldn’t help jumping a little, a broken moan falling from his lips. Dean chuckled behind him, warm and breathy against his hole. “Relax, baby boy...I’ve got you.”
Sam looked back over his shoulder at his big brother, hazel eyes glinting as he nodded again, because if there was one thing that Sam would never doubt in his life, it was that his big brother had him. “I know you do, Dean. Do anything you want. I’m ready for it.”
Dean’s jade eyes brightened, impressed and clearly touched by the confidence in him, and he nudged Sam forward a little further, sending him right up between Cassie’s legs. Her delicate fingers closed over the younger boy’s chin, drawing him in for another sweet kiss--and then Sam gasped in shock as her other hand wrapped around his erection, stroking it leisurely. “Let’s see if this can’t help you relax,” she purred, and Sam bucked into her grip, whimpering helplessly.
Dean took full advantage of his distracted state, and Sam cried out loudly when he felt--Dean’s tongue , that was his brother’s tongue, hot and wet and filthy, directly against the tight furl of his entrance.
From that point on, the pace of the entire evening picked up rapidly.
Dean was relentless, sucking and licking at Sam’s hole until Sam could feel the older boy’s spit running down, over his balls. Cassie’s clever fingers were there to catch the streaks, and she rubbed it up over Sammy’s cock and balls, using it to lubricate her hand’s movements as she played with Sam, stroked him, and murmured gentle encouragements against his lips, and jaw, and throat as she continued kissing his mouth. Sam felt as if he had to be in some kind of twisted, surreal heaven, suspended in waves of sheer pleasure, feeling Cassie’s hand on him and Dean’s tongue working inside of him.
Before he could muster the strength or even the breath to warn them, Sam was shaking and gasping, coming into Cassie’s hand and all over her still-bare stomach and thighs.
Behind him, Dean growled darkly, and Sam tried to stutter out some variation of “What’s wrong?”
It was Cassie who answered, laughter in her tone. “He’s making that noise because when you come, your asshole gets all nice and tight, just like a pussy does,” she whispered, almost conspiratorially. “You’re squeezing down all snug and pretty on his tongue. He loves it.”
Sam moaned at the words, his hips jolting as another wave of his release rushed through him at the thought, and he felt Dean’s fingers press into one of his ass cheeks, as if praising him silently for his reactivity.
Spent and exhausted, Sam collapsed onto his side beside Cassie, dislodging Dean and leaving the older two lovers facing each other. Dean prowled forward immediately, not deterred at all by Sam’s sudden shift in position, dipping down to lap up his brother’s release off of Cassie’s skin. Sam whined softly as he watched the display, stunned that Dean would want to do that.
Cassie lazily cast one hand toward him, covered in some more of his come, and Sam hesitated before accepting it. Holding her wrist delicately, he leaned in to lap up his own semen from her dark skin, his tongue darting out in kitten licks until he had gotten it all.
Dean was watching him intently, his eyes dark and hungry, and Sam found his own voice once he was finished giving Cassie’s hand a tongue bath. “You gotta come, too, De.”
His brother smirked, nodding as he glanced over at Cassie. “I do, yeah. But you don’t gotta help me out with that if you’re too wiped out, little brother. I can just jerk off lookin’ at how damn pretty you two look, right now.”
Sam pursed his lips at the offer, then shook his head and shifted right back up onto his knees, determined. “I want to help. Tell me how.”
Cassie interjected again, lazy contentment in her voice. “You know what a facial is, Sammy?” Even as he shook his head, Sam did not miss the way Dean reacted, green eyes sharpening and his tongue sliding out to wet his lips; with that, Sam wouldn’t have cared if whatever it was painful--he just wanted to give it to Dean.
“It means that Dean would come all over your face,” she explained, and Sam’s breath caught at the idea of that, watching his brother lazily stroking his cock. “You can suck him some, or he can just jerk off--but when he’s ready, he’ll tell you to pull back, and he’ll jerk it until he comes.”
Sam was nodding before she had finished speaking, eager and wanting. “Yes, yes please, I want to do that. De, please?”
Dean only laughed, then leaned forward to kiss him again, hard and brief. “Don’t gotta beg me for that, baby boy. C’mere.”
Letting Dean pull him back onto his hands and knees, Sam melted as his brother took a moment to kiss him. The gentleness of Dean’s lips against his was startling, given everything, but Sam didn’t break the contact or push for it to be harder.
Then Dean’s hand slid into his hair and he guided him downward, and Sam huffed a laugh as he remembered watching Cassie earlier. Utilizing what he had learned from observing her, Sam moved in to close his mouth over his brother’s cock. He felt more certain this time, at least more sure that he couldn’t do this wrong--as long as he didn’t use any teeth, Sam figured that Dean would enjoy his performance, no matter how rough it was.
He might have been an amateur--a novice, really, clueless as to how this was done “properly”--but Sam was certainly enthusiastic enough. He sucked, and licked, and kissed when he could, using his tongue when he could manage to, and reveling in every little noise and sigh that Dean let out.
Eventually Dean groaned, breaking Sam’s concentration as he began tugging lightly at the younger boy’s hair--Sam moaned in surprise at that sensation, amazed at how intensely he felt the faint wave of stings across his scalp--and Dean huffed a laugh at his reaction. “Pull back, Sammy, I gotta--I’m gonna blow, and I really wanna see it all over your face.”
Sam obligingly drew back, remaining on his hands and knees, and he raised his face to blink up at Dean with his very best wide-eyed look of innocence, even batting his long lashes a little for effect.
To his delight, Dean cursed at the sight of it and grabbed his cock, still glistening with Sam’s spit, and began jerking himself off, tight and fast.
He came within a minute, and Sam’s lips parted around a gasp as the thick white fluid struck his cheeks, nose, and mouth, some of it clinging to his lashes, and some landing directly inside of his mouth as it hung open. He stayed put, waiting until Dean had finished before Sam tentatively licked his lips, and swallowed everything that he had caught in his mouth.
“Now that is a show worth paying for,” Cassie breathed, and when Sam glanced back at her, she was lazily sliding two fingers in and out of her pussy. He smirked at her, using his own hand to gather up more of the mess on his face and licking it up, just to watch her coffee-brown eyes darken. Her hips undulated upward as her thumb brushed against her clit, and she came again, quiet and sleepy, eyes on Sam’s face as he licked up his brother’s come.
Dean’s fingers slid beneath his chin, turning Sam’s face back towards him, and Sam gasped out another little laugh as Cassie surged up onto her knees to meet Dean’s lips in a gentle kiss over the younger boy’s shoulder. Both of them moved in close around Sam, once more sandwiching him between them; they both leaned in to begin licking and kissing his cheeks, sharing Dean’s come between their mouths and cleaning Sam off as they went along.
Once he was more covered in their saliva than Dean’s semen, Sam sank down and slid out from between their warm bodies, lying on his side in order to watch as Dean and Cassie continued making out lazily. He could see hints of Dean’s come still lingering on their tongues, white and milky and vanishing slowly as they shared it back and forth, and he whimpered softly. His entire body was twitching and buzzing, and Sam nuzzled his damp face against the bedding in order to quell the surge of heat that rushed through him just from watching them kiss each other like that.
When they finally broke apart, Dean moved to lay down behind Sam, spooning up against his back and slotting their hips together neatly. Cassie slid off of the bed to go get a wash cloth before she returned to the bed, leisurely cleaning both boys off. Once done, she tossed the cloth aside, and laid down facing Sam.
His eyes dropped down to her breasts, so temptingly close to his face, and Cassie chuckled, nodding knowingly. Her fingers carded into Sammy’s hair, and he let her guide him forward and downward, until he could take one dark nipple into his mouth and suck on it gently. The way that she moaned was almost more satisfying than the erotic sensation of the act itself, and Sam’s hips bucked lazily; his body was too spent to handle fresh pleasure, but his mind savored what he was doing to her, and how vocally she was responding.
He felt Dean moving, and when Sam slid his gaze sideways, he couldn’t help groaning when he realized that Dean had reached over his hip, and was fingering Cassie slowly, two digits thrusting in and out of her cunt and his thumb rubbing her clit. Sam doubled his efforts, moving to the other nipple when she nudged him to, and within a minute, Cassie came one last time with a soft, throaty cry, bucking against Sam’s mouth and Dean’s fingers.
He could feel Dean rolling his hips as well, humping Sam’s backside slowly, but when he started to turn to look back at him, Dean gently stopped him with his hand on Sammy’s shoulder--a hand that now smelled sweetly of Cassie’s juices. Sam grabbed his wrist, bringing his fingers to his mouth and sucking them clean, and Dean growled softly, biting the back of his brother’s neck. “Good boy. You're such a quick learner, fuck...”
Once Dean’s hand had been licked clean, Sam finally settled into the bed for good, feeling an unnatural weight of drowsiness sinking down into his very bones. “‘S it always this tiring?” he mumbled, smiling faintly when Cassie chuckled at his inquiry.
“It can be,” she whispered back. “Feels good, doesn’t it?” Sam could only nod his affirmation to that, and she stroked his sweat-damp hair back from his forehead, leaning in to brush a kiss over his closing eyelids. “Rest, Sam. And if you like, once you catch your breath, I’ll show you the magic of a prostate orgasm.”
Sam cracked one eye, mildly curious at that. Behind him, Dean hummed his approval at that promise, tucking his face in against Sam’s neck to sleep.
Saving Cassie’s offer for when they woke up again, Sam’s eyes sank closed once more as he felt them shift in around him, their combined body heat blanketing him and leaving him feel safe, sated, and content.
His brother’s voice was the last thing he heard. “Got so damn much I’m gonna show you, Sammy. This is just the beginning--trust me.”
* * *
Present Day
Gabriel propped his chin on Sam’s stomach, blinking over at Dean as the older Winchester continued absently petting Cas’ face with tender fingers. “I’m amazed that you two actually fucked girls.”
Sam snorted, making Gabriel shift as his belly did, and glanced at his older brother with twinkling eyes. “Dean was just a player back then, no concern at all for gender. He didn’t care, as long as everyone involved was consenting and having fun.” He reached out, the backs of his fingers grazing against his brother’s cheek in a soft caress, which Dean leaned into with a fond smile. “After that first time, we were always first priority for each other.”
Cas made a little noise, questioning, and Dean laughed as Sam’s hand fell away. “Well, now the four of us are first priority, angel,” he whispered, leaning down to kiss Cas’ nose. Sam nodded, lowering his free hand to pet Cas’ hair in gentle assurance, while his other hand skimmed over Gabe’s shoulders and back, teasing the skin lightly.
“We all belong together,” Sam agreed quietly. “Us four, against the world.”
Leaning farther forward, over both Cas and Gabriel, Dean pressed a soft kiss to his brother’s forehead, and nodded.
“Ain’t no me if there ain’t no you,” he confirmed, squirming down to join their little dog pile as Gabe reached over to turn off the light, casting the four men into warm, soft darkness for the night.