Requests and Challenges - Just Like Dean: Part Three

Apr 02, 2015 19:03



Master Post

Title: Just Like Dean
Author/Artist: girlgotagun
Pairing(s): Sam/Jess, Jess/Toy, Jess/Dean/Sam
Full List of Kinks: toys, porn, voyeurism, dirty talk, light incest, double-penetration
WARNING: None

Written for this prompt at spnkink-meme.



Back to Part Two

~~~

Sam was having some trouble coming to terms with the turn of events that had taken place in his life. First, he had watched his girlfriend-the girl he planned to marry one day-fuck herself with a dildo modelled after a famous porn star. Then, he had fucked her with it, offered to use it to fuck her in the ass as he pounded her pussy. Then his brother Dean had visited, which had been awkward for reasons he hadn’t, at the time, been able to fathom.

And all of those instances he could get on board with if they were that simple. Hell, when he thought they were on simple his mind was doing a constant victory dance. He loved Jess, loved how fucking dirty she could be, all for him. And he loved his older brother, was psyched that he had finally come to visit after they had been separated for so long. Awkward or not, it had been great.

Until Sam discovered the source of the awkwardness.

Dean, his big brother, his childhood protector and his sponsor through college, was in fact Daniel Wesson, the porn star that Jess’ dildo was modeled after. Her favorite porn star, and by extension the man who had likely gotten her off many, many times before Sam came along. It was enough to make Sam want to scream, to kick and throw a temper tantrum the likes of which hadn’t been seen since he was a kid and adamant that Dean wasn’t playing fair.

Here they were, adults. And Dean still wasn’t fucking playing fair.

Sam hadn’t spoken to his older brother in the three days that had passed since his visit and Sam’s discovery. Dean had called-twice-but Sam hadn’t picked up, hadn’t returned the call, hadn’t even shot off a lame-ass text message to his big brother.

He hadn’t talked to Jess much, either, but that was more because of her than any decision he had made to do so. Jess had been in and out of the apartment all weekend, only staying for brief periods of time before she needed to go to the library, or out to drinks with a friend.

Maybe she was fucking Dean.

Would it surprise him?

Yes. It would honestly surprise him if Jess cheated on him with Dean. Just because…it was Jess. He knew her better than that.

That wasn’t to say that it hadn’t happened before. No, not Jess, never Jess. But there had been other girlfriends of his that had ended up under his big brother. His prom date, Rachel Nave, for example. On prom night, no less.

But Jess was different. He knew that. So why did his mind keep returning to that dark place?

Maybe Jess is fucking Dean.

He couldn’t stop the thought from racing through his mind, no matter what he personally believed. The thought was there, like an itch deep under his skin. Once he was aware of it, he couldn’t get rid of it.

So that was why, when they were sitting on opposite ends of the couch two days later, bodies curled away from each other, Sam had to take the opportunity to ask, once and for all. “Are you fucking Dean?”

Jess’ head swung around to face him, a look of genuine shock on her face. Sam instantly felt guilty for asking. Had to, though. He had to know.

“No! Sam…” her voice was gentle as she unfolded her legs from under her and slid across the couch toward him, her hand coming to rest on his chest to brace herself as she swung a leg over his, leaning in to press light kisses to his cheek, his jaw, his lips. “Sam, I love you. I don’t want-”

She cut herself short and Sam almost laughed out of dark humor because fuck, he had to hand it to Jess, she wasn’t the lying type.

“You want to fuck him, though?” Why was Sam poking at it? Nothing about knowing could possibly make him happy.

“I was thinking…” Jess trailed off, licking her lips. “Dean said if you found out…that he’d be happy to…join in.”

Sam stared at her, trying to figure out where she was going with this. She didn’t speak again right away, and he made a sound in his throat to encourage her to continue.

“I have this…idea. A fantasy, I guess.” She squirmed a little in his lap and Sam both wished she’d hurry up and spit it out and that he had never opened this can of worms in the first place. She leaned closer, nipping up his jaw to his ear before taking the lobe in her mouth and biting down lightly, pulling at the tender flesh. “I want him to fuck me while you watch, Sam. Wanna know you’re watching it happen, hear your voice while he’s inside me.”

Sam turned that over in his head. A part of his mind rebelled at the thought of Dean touching Jess at all. Another part of him, and he couldn’t deny it, found the idea to be a huge, unexpected turn-on.

Encouraged by the lack of rejection toward the idea, Jess continued talking. “Wanna know it’s driving you crazy, watching your brother fucking me, making come on his dick, but that you can’t do anything about it. Then, when it’s over, I want you to take me, show me who I really belong to. Own me. Make me come harder than he ever could.”

Sam had to let out a low moan at that; couldn’t help it. The idea was taking root in his mind, as securely as if he had thought of it himself.

“Please, Sam?” Jess breathed against his mouth. “Won’t do it if you don’t want to.”

“One condition,” Sam said, a smirk twisting his lips as the idea clicked into place. Jess squirmed in his lap again, eager to hear what he had come up with. “You have to let Dean fuck you with that dildo up your ass. Let me watch as he takes both holes.”

“God, Sam…”

“And…” Sam let the word hang in the air for a minute, relishing the way she writhed in anticipation, nearly getting off on the idea alone. “That’s all you get. After that, I’m gonna keep you on the edge, keep you begging me-only me-to fuck you. You won’t get to come until I decide you can. Might be hours…might be days.”

God, he hoped she’d say yes. And of course she did, nodding her head in agreement almost immediately.

“Need you now, though,” she moaned, her face buried in his neck as she ground down on his hardening length.

Sam gave her a predatory grin and stood, picking her up with him, and took her to their bedroom.

~~~

The other end of the line was quiet, and if he couldn’t hear the faint crackle of a live line Sam would’ve thought that Dean had hung up on him. He waited patiently as he imagined his older brother-normally so confident and in-control-struggling to form words.

“Fuck, Sammy.” That was all he got, uttered on an exhale.

“So what do you think?”

He heard the sharp inhale and slow exhale, tell-tale signs that Dean was smoking on the other end. Sam was a little disappointed the other man hadn’t quit after all these years.

“Fuck, Sammy,” Dean said again. “I’m just trying to wrap my head around it, you know? Thought you’d be pissed as hell when you found out what I do, but instead you’re calling me asking me to fuck your girlfriend?”

“Jess said you’d offered.” Sam shrugged even though Dean couldn’t see him.

The line was quiet again for a moment before Dean spoke. “Wouldn’t turn it down, nah. And I gotta admit, I like this plan a lot better than you being involved-no offense, baby boy.”

“Don’t call me that when we’re planning how to fuck my girlfriend together. It’s weird.” Sam rolled his eyes.

“Yeah, that’s the weird part.” That sharp inhale, slow exhale again. “Yeah, I’ll do it. Sure you can handle it, Sammy?”

“Why couldn’t I?”

“Well, apparently your girlfriend’s already a huge fan of my dick, and she’s never even really had it. Risky, isn’t it?”

Dean was teasing him, just fucking around, and Sam knew it, but it still ruffled his feathers, so to speak. “I really doubt I have anything to worry about.”

“Suit yourself.” Sam could imagine Dean shrugging on the other end of the line. “Friday night, then?”

“Yeah.”

Two days away. In just two days, Sam would be watching his girlfriend get fucked by his older brother.

He smirked. And for three days after that, she’d be begging him to do the same.

~~~

The awkwardness didn’t set in until about a half-hour before Dean was scheduled to arrive at their apartment. It occurred to both Sam and Jess that they had no idea how this was supposed to start, only the eventual result. Dean was lucky, Sam thought. He had to have played out a hundred scenes like this on camera, the openings scripted for him. For Dean, this would be nothing. For Sam, it was a nerve-wracking awkward wait.

At exactly nine o’clock there was a knock at the door. Sam and Jess locked eyes, each looking at the other expectantly. Sam spread his hands in a wide gesture, shrugging slightly as if to say, what? I’m not involved in this.

So it was Jess who answered the door, and they both realized quickly that they didn’t need to worry about lines, or setting up a scene, because the second the door was open Dean was on Jess, his hands coming up to her face and holding her head steady as he kissed her passionately, walking her backward and then kicking the door shut behind them. He pushed her up against the wall, his body covering hers and his hands leaving her face to travel down to her hips, pulling at the hem of her tank top and yanking it over her head before returning his mouth to hers, plunging and pillaging with his tongue, thoroughly ravishing her.

It was happening a lot faster than Sam thought, and he felt jealousy rising up in his chest as Dean trailed one hand down Jess’ thigh, hitching her leg up to wrap around his hips, creating a better angle to thrust his denim-covered length against her soaked center.

As though Dean could sense Sam’s envy, he pulled his mouth away from Jess’ and looked over his shoulder, eyes dark and that shit-eating grin on his face as Jess gasped and rubbed herself against him. “Remember, Sammy, you’re just watching tonight.”

Sam nearly bit through his tongue.

Dean brought one hand behind Jess’ back and made quick work of the clasp on her bra, pulling his upper body away from hers to pull it off of her shoulders and toss it over his own, towards Sam. Jess’ hands were pulling at his shirt, desperate for the feel of skin-on-skin, and he quickly ridded himself of that, too.

He hoisted her up, guiding her legs to wrap around him before gripping her ass and moving away from the wall to carry her to the bedroom. This took Sam by surprise. He hadn’t imagined this taking place in their bed-his bed. But he followed them anyway, and took a seat in the chair by their closet, the one that had until that point served no real purpose other than to-as Jess put it-tie the room together. Well, now it was the chair that he would sit in to watch his brother fuck his girlfriend.

He watched as Dean flipped her over onto her stomach, felt slight relief that Dean was going to do it that way, keep it impersonal. From his seat he had a view of the two of them from the side, and he focused on Jess, doing his best to cut Dean out of his vision as he stripped her and then himself of their pants and underwear.

“Fuck, no wonder Sammy’s so possessive of you.” Dean’s voice was a low growl and it surprised Sam what hearing his brother’s fucked-out voice did to him when it was coupled with Jess’ broken gasps and moans. His brother’s hand was smoothing down Jess’ back, finally reaching the cleft of her ass and then grazing further to dip into her pussy. “So fucking hot. I wouldn’t want to share you, either.” He fucked her slowly with his fingers, and Sam imagined that it was him doing it. “How’d you do it, huh? How’d you convince him? You wait until he was deep in your tight cunt, about to come, and then ask him to let his brother fuck you? You convince him with your pussy?” Dean let out a choked groan and Sam knew from the sounds that Jess was making that she had just gotten impossibly wetter, tighter, hotter around his fingers. “God, what a fucking slut.”

And Sam should be mad that Dean was talking to his girlfriend that way. But he knew what it did for Jess, how worked up she got, and Sam imagined that his filthy mouth was probably one of the reasons that he was one of her favorites. He felt himself getting hard despite his initial jealousy, which was quickly making way for an inferno of lust.

Dean’s fingers were pulling out of her pussy now, gliding up towards her ass and the tight pucker nestled between the perfect globes of her ass. “He ever fuck you here? You ever let him slide in, fuck your ass until he comes? Or is that just for when you think about me, fucking those other girls? You slide that fake dick in here, imagining it’s me.”

Jess didn’t answer, her voice already too fucked-out to respond. Dean smirked and teased one finger into her ass. “Mmm…maybe I’m wrong. Maybe you’ve never had anything in here.”

Sam smirked. He had been there. His cock gave a painful throb at the memory.

He watched his brother work Jess open, starting with a single finger and ending with three before he withdrew, leaning over her to open the bedside drawer. He came back with the dildo and a condom. It occurred to Sam that he and Jess hadn’t used condoms in a long time, not since moving in together, and Sam had no fucking idea how old the ones in the drawer were. But he knew they were good for a long time, and they had only been in the apartment six months, and lust was clouding his mind as his brother slid the dildo into Jess’ pussy, letting her fuck herself on it, covering it in her slick fluids, and then moved to slide it slowly into her ass.

Jess let out a scream that was half-pleasure, half-pain, her nails digging into the bed under her as she was filled to bursting.

Dean swore quietly. “Shit, baby. You sure you’re going to be able to handle all of this?” His voice was taunting, but Sam could hear the underlying concern in his brother’s voice.

Sam took a second to unstick his throat and find his voice. “She can take it.” His eyes met Jess’ as her head turned to look at him, a flush rising in her cheeks. “Can’t you, baby? That’s right. You can take it all; can take anything he has to give you.” He smirked at his brother. “I’m bigger, after all.”

Dean let out a harsh laugh. “Well, fuck. You’re fucking trooper of the year then, aren’t you, you fucking cockslut?”

Jess let out a moan and spread her legs wider. Sam felt a strange surge of pride as he watched her prepare to take Dean in. Atta girl, his brain screamed.

“Please, Dean…” They were the first words Jess had managed to force past her fucked-out vocal cords. “Need you…”

Dean swore loudly before ripping the condom open with his teeth and rolling it on over his straining dick. He shifted forward a bit on his knees, gripping Jess’ hips to hold her steady, and then he was slamming into her.

Jess screamed, arching against him, mind blown from the completely full feeling of Dean’s dick in her ass and her pussy. Dean let out something like a feral growl. “Fuck…so fucking tight…so fucking hot. Fuck, baby.”

His brother was thrusting in and out of Jess now, a steady, punishing pace, and Sam unzipped his pants, easing them down, along with his boxers, over his straining dick and halfway down his thighs. He gripped his cock, pulling hard, in time with his brother’s thrusts, imagining himself in Dean’s place.

“Fuck, baby, you’re doing so fucking good,” Sam gasped, watching Jess take it all, her face a mask of complete pleasure. “Hope you take it that good for me.”

Jess let out a desperate sob at his words and Dean swore again and picked up the pace.

“Fuckin’… Keep talking to her, Sammy. She gets so fucking wet when you talk.”

Sam felt his chest swell with possessive pride. “Gonna have you begging for it, Jess. Gonna let you get so close to what you want, and then send you on to class. That what you want? A plug in your ass and one of those little vibrators in your pussy? Make you keep it in all day, forbid you to come. Make you wait until you’re with me, until I say you can. Can you do that for me, baby? Can you stop yourself from coming like the cockslut you are? Wait for me to give it to you? I’ll have you begging for it, Jess, and fuck I’ll make it so good.”

“Please,” Jess choked out, pushing back against Dean’s brutal assault, feeling the two dicks slide against each other with only a thin membrane of tissue separating them. “Please, Sam. Let me come, please!”

“Go ahead, baby. Dean’s got you. Come all over his dick.” Sam smirked as Dean let out a startled cry and then one last loud curse as Jess came around him, milking him, making him shoot his own load. Sam worked his dick faster, chasing his own orgasm, and came soon after.

Fuck, he hated to admit it, but Jess had some fucking fantastic ideas.

The End.
I hope you enjoyed it. :)

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kink: porn/porn stars, au: non-hunter, warning: language, character: dean winchester, kink: toys, pairing: dean/jess/sam, kink: dirty talk, character: sam winchester, warning: sexual content, kink: voyeurism, fandom: supernatural, kink: mild incest, kink: double-penetration, prompt fill, character: jessica moore, category: pwp, category: au

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