Family Affairs | Part 2

Pairing: Dean x Sister!Reader x Sam 
Rating: 18+
Tags: dark pornStar AU, grooming, sibling incest, prostitution, filming sex, teaching blow jobs, deepthroating, anal sex, degradation/humiliation, car sex, dirty talk
WC: 2,450

Created for: Bee!! When she came to me with this commission idea I absolutely DIED and we immediately started brainstorming and I’m SO excited to finally be writing and sharing this with you all 🖤

Masterlist

“What are you gonna teach me?” Y/N asked nervously, breathlessly. Sam smiled, tucking a stray piece of hair behind her ear. 

“We’re gonna teach you how to be what you were born to be, sweetheart,” Dean smirked, running his hand down her front and between her legs. Y/N moaned, humping against his fingers as they toyed with her clit. 

“Gonna teach you to be the best little cockslut you can be, baby girl,” Sam growled against her neck, sucking a bruise into her skin, marking his territory. 

Y/N let herself be manhandled down onto the bed between her brothers. They spent ages just making out, teaching her to kiss the way they liked it, biting on her lips until they were pink and puffy. Sam and Dean made out in front of her while they told her to touch herself, stripping themselves out of their clothes until they were bare, cocks jutting out between them. Sam noticed that Y/N couldn’t take her eyes off their hips, grinding their erections against each other, and he grinned down at her. 

“Touch us, baby girl. Don’t be shy.” 

She reached out a hand timidly and let her fingers trace down Sam’s cock, which jumped under her touch. 

“You’re not gonna break ‘im, sweetheart,” Dean chuckled deeply, wrapping his hand around Y/N’s and showing her how to stroke him. Sam groaned under their combined touches, throwing his head back in an exaggerated show of pleasure for the camera. 

“Whaddya think, darlin’?” Dean asked with a smirk. 

“I– I like the feel,” Y/N stuttered, looking up at Dean bashfully. 

“Tell the camera, baby girl,” Sam tilted her face toward the device, holding her chin so she was looking straight into the lens as she spoke. 

“I like it,” she whimpered, so sweet and pathetic. Sam felt a bead of precum pulse out of him as he watched her. 

“What do you like?” Dean probed, grabbing Y/N’s other hand and placing it on his own dick, so he wasn’t left out of the fun. 

“I like touching your cocks,” Y/N said nervously into the camera, glancing up to Dean and Sam for approval, which they readily gave. 

“You like touching your big brothers’ dicks, huh baby?” Sam cooed, thrusting into the channel of her hand as she jerked both of them off, sometimes bumping the tips of their cocks together and making them groan. 

“Yes,” she nodded, clearly embarrassed. 

“Well, then you’re gonna love what comes next,” Dean grinned, pulling out of her grasp and throwing himself down on the bed. “Come show ‘er how it’s done, Sammy.” 

Sam let Dean pull him down onto all fours, and he crawled between his brother’s legs, ducking low to place a light kiss on the tip of his cock. 

“Watch and learn, baby sister,” Sam grinned, then swallowed Dean down in one push. 

Y/N watched with rapt attention as Sam sucked Dean down his throat, holding him there until his gagging settled and he could hum contentedly around the intrusion. 

“He’s such a good cock sucker,” Dean praised, bucking his hips to fuck himself in and out of Sam’s mouth. “Think you can be this good for us, Y/N?” 

She tried valiantly, kissing and licking her way down Sam’s cock and back up, sucking the tip between her lips, but when Dean forced her head down Sam’s shaft until he hit the back of her throat, she immediately choked and pulled back. 

“Pathetic,” Dean grunted, shoving her aside and finishing Sam off himself. 

Yes, Y/N still had a lot to learn. 

Dean picked himself up off the asphalt and wiped his mouth with the back of his hand. The guy he’d just blown was busy catching his breath, his head lolled back against the shabby siding of the truck stop bar, so Dean was able to slip away without any further conversation. He hated when they got chatty. 

Ducking back into the bar, Dean scanned the crowd for Sam. He found him cleaning up a round of pool in the back corner and grabbing a wad of cash off the table with a smirk. 

“This was fun boys,” Sam grinned, pocketing his winnings and then catching sight of Dean. Dean gave his brother a look and Sam nodded, waving goodbye to his disgruntled playmates and following Dean back out the door and into the parking lot. 

“Clean up good, then?” Dean called over to Sam as they made their way to the Impala, parked around the side of the building. 

“Decent,” Sam nodded. “You?” 

Dean reached into his pocket and waved the wad of bills he was carrying at Sam. Looking back, he saw Sam’s smirk in a flash of headlights from a passing car. 

“How many you suck tonight?” Sam asked with a wicked glint in his eye. Dean knew Sam got off on this part, hearing about all the shit Dean got up to on their working nights. 

Without words, Dean answered Sam by pulling open the back door to their car and climbing in on his hands and knees. He heard Sam laugh through the open door, then felt him climb in behind him. Dean knew Sam would know what this answer meant; they’d been here before. It meant he’d sucked enough dick that he was sporting a boner of his own, now, as a result. 

“Give me that money,” Sam demanded, sticking his hand over Dean’s shoulder, and Dean slapped the cash into his palm so he could count it. 

“Good enough, little brother?” Dean chided, pulling down his jeans and reaching into his boxers to finally get a hand on his dick. The cotton was wet where he’d been leaking precum for the past hour. 

“Yeah, you were a good little whore tonight, weren’t ya, boy?” Sam sneered, and Dean could hear him thumbing through the bills as he stroked his cock, groaning at Sam’s quip. 

“You gonna put me back to work, then?” Dean panted, swivelling to look behind him and throw Sam a wink. “Got myself all prepped up and the fuckin’ johns left me high and dry.” 

“Oh, poor baby,” Sam pouted. “Can’t let all your hard work go to waste, can I?” 

Sam shoved his elbow between Dean’s shoulders, forcing him back to his hands and knees while Sam tugged his boxers down far enough to uncover Dean’s ass, the plug he was wearing clearly visible between his cheeks. Dean gasped when Sam wrenched it from him without preamble, probing at his rim with his fingers, teasing them over the wet, puffy flesh. 

“How did anyone resist such a pretty fuckin’ hole, huh?” Sam asked challengingly, and Dean grunted in response. “Maybe you’re not such a good little whore, after all? If you can’t even convince one of these pervs to fuck you,” he sneered, pressing two fingers in, making Dean squirm. 

“Maybe I was savin’ myself for you, Sammy?” Dean teased, wiggling his ass back on Sam’s hand. “Know how pent up you’ve been with Y/N not puttin’ out yet.” 

Their little sister had been the bane of their existence the past few weeks. The bitch was coming along, but she was still skittish. The most they’d gotten out of her so far was a blowjob each, and some hand jobs. Mostly they’d just been fimling her touching herself while she watched the two of them fuck. Who knew she’d turn out to be such a kinky little thing? But the second they’d found her watching their porn, Dean and Sam had both gotten their hopes up. They hadn’t had any pussy to fuck in so fucking long, it was all either of them could think about now. And Dean knew Sammy in particular was taking it extra hard, though he couldn’t work out why. 

“I think it’s time for you to shut the fuck up,” Sam snapped, reaching around Dean and shoving his night’s earnings into his mouth to gag him. “Just be a good little whore and take it, yeah?” His little brother fumbled behind him for a moment, and then Dean felt the blunt head of Sam’s dick pressing against his entrance. He thrust back into Sam, letting his body swallow him up and squeeze around his cock. 

Sam stilled, let himself catch his breath for the space of a heartbeat, then began rutting into Dean like he hadn’t cum in weeks. Dean knew for a fact Y/N had jerked him off this morning while he’d been in the shower, but that didn’t seem to matter. Sam plastered himself over Dean’s back, forcing him down against the vinyl seat so he had difficulty breathing, with his mouth stuffed full and his nose crushed into the upholstery. A series of greedy moans bubbled out of Dean the harder his little brother used him, his thrusts grinding Dean’s cock into the seat beneath him, the sweat dripping between their legs easing the way for him to fuck himself down into the car. 

“Fuck,” Sam grunted, one hand flying to the back of Dean’s neck to hold him in place. “Can’t wait until I’ve got something new to fuck, something tighter. You’re gettin’ pretty fuckin’ sloppy, Dean, whorin’ yourself all over the place.” 

Dean moaned in response, his mouth still playing house to the cash Sam had shoved there. 

“Can’t fuckin’ wait to feel how tight she is, our little virgin. Y’know, she told me she’s never even fingered herself before? Wonder if we’ll even fit,” Sam groaned, his thrusts becoming more erratic the more he spoke. Dean always loved how filthy Sam’s mouth was, it got him off quicker than anything else. “But I guess you’ll have to fucking do for now, huh, baby boy?” 

Dean gargled against his gag, unable to spit it out with his chin being held down into the seat. He could feel his body beginning to seize up, climbing higher towards the edge he’d been chasing all night. Sam chuckled darkly, and Dean knew he could sense it. He could tell Sam was close too. 

“Aw, is the little whore gonna cum? Just from having my cock in your ass? God you’re such a fucking girl, baby boy. You’re gonna have to teach Y/N how to cum on just my cock, like a good little bitch, how’s that sound?” Sam grunted, and Dean came, his hole clenching around Sam violently as his cock spilled beneath him, painting the seat in streaky white. 

“That’s it cunt, so fuckin’ good f’me,” Sam moaned through his own release, and Dean felt the warmth begin to slip out of him as soon as Sam pulled himself out, collapsing behind his brother on the back seat. 

Dean heaved himself up, spitting out the money he still had tucked between his teeth. 

“Jesus Christ,” he groaned, massaging his jaw as he stole a glance at Sam. “You okay over there, man?” 

“Fine,” Sam huffed, dragging a hand over his face and then ruffling up his hair to get it out of his eyes. “Lay that out to dry,” he said pointedly, glancing over at the discarded bills. “You got drool all over it.” 

“Yeah, whose fuckin’ fault is that?” Dean rolled his eyes, but stooped to pick up the money. They couldn’t afford to lose any of it because it dried stuck together and tore when they pried it apart. 

“It’s a decent haul,” Sam commented genuinely this time, their moment of humiliation for sex’s sake over now. 

“Can you imagine how much more we’ll be raking in once we’ve got Y/N working with us for real?” Dean voiced his thoughts aloud. “We save up, we might be able to buy a house, get out of that shitty trailer park.” 

“We don’t know how much her porn is gonna bring in,” Sam shrugged. “It should do well, for sure, but I doubt it’s gonna triple our income,” he remarked skeptically. 

“No, not the porn, man,” Dean sighed exasperatedly — apparently Sam still had his sex brain on. “I mean out here, with the two of us. You know, I bet we could even get triple figures for her first time. She’s hot enough, and she’ll be just slutty enough without actually being a slut, y’know?” 

“You wanna sell her virginity?” Sam stuttered unnaturally, and Dean turned to look at him, noticing his face had gone white, even in the dark of the deserted parking lot. 

“Uh, yeah, it’s like the fuckin’ motherload,” Dean scoffed. “I saw some model online selling hers for over a million.” Sam just gaped at him. “Plus if we film it then we’ll keep making money off it on the site – the gift that keeps on giving, Sammy.” 

Dean ducked out of the back seat and walked around the car to slide behind the wheel. Sam joined him up front after a moment’s hesitation, and Dean revved the engine and pulled out of the lot back onto the deserted road that led towards the highway. Sam was being weirdly quiet, so Dean punched a cassette into the player — something he knew Sam would complain about — and cranked up the volume. 

Still, Sam stayed silent. 

“This isn’t gonna be a problem for you, is it?” Dean turned down the music with a huff, glancing sideways at Sam. 

“Huh?” his little brother startled from his thoughts. 

“Y/N. Are we gonna have an issue?” Dean pressed sternly. 

“No,” Sam shook his head, “no, I just… I guess I just thought one of us would be the one to do it, like you did for me.” Dean flicked his eyes back to Sam again and saw him shift awkwardly, dejected. 

“Aw, you wanted to pop her cherry, Sam? Take care’a her like a good big brother?” Sam just shrugged, and Dean couldn’t stifle his laugh. “Hate to break it to ya, man, but we are not good big brothers. We’re teaching our baby sister how to be a prostitute.” 

“Maybe she doesn’t have to be,” Sam looked at Dean nervously, then back at the road, continuing. “Maybe she just does the porn stuff, and we don’t bring her out with us for this crap.” 

“Sammy, come on, she’ll make a killing! We’ve gotta use ‘er,” Dean argued, perplexed as to where Sam was getting these protective, familial feelings from. 

“Well, we’ve gotta focus on training her up first, either way,” Sam interrupted Dean’s thoughts. “Based on her last performance she is definitely not ready for the streets. She needs to build up some confidence.” 

“Well it’s a good thing we’re almost home then,” Dean grinned. “Time for more practice.”