It's got to be below freezing, Dean wrapped up in a hoodie and a pair of shorts, his skinny legs on display as he rested against the side of the building down the street from their motel, keeping his eyes on it. He can see his breath in front of his face, misting up the air and hanging there, and he's shivering, teeth clicking together from the cold. He's not used to this, but he puts up with it for his family; they're broke as hell, and this gets some money, if only a little.
He's sixteen but he can pass for eighteen, so no one asks too many questions. He's been told he has great cocksucking lips, and he has an ass to die for. The guy who had him earlier made sure to comment on his eyes every five seconds, and Dean knows he's good looking, if slightly blue because of the cold. The South Dakota hoodie he has on is too big for him, and the shorts look like they could belong to Sammy, and Dean knows he looks like a hooker. And that's probably a good thing, seeing the neighborhood he's in.
Dean pushes himself off the wall, stepping forward; he can see their room from here, and he hopes to god that Sammy's okay, because he's doing this for him. If their dad knew Dean was doing more than just hustling pool, John would kill him. But Dean's okay with that, he's completely fucking cool with doing this, because they need money more than anything else right now, and credit card fraud can't keep them going forever.
A hand slips over Dean's mouth before he can react, the teenager's eyes going wide before he grabs at the arm, intent on flipping this son of a bitch over his shoulder, heart pounding. Lips are pressed against his ear, a beard scratching him slightly, and a familiar enough voice comes from behind him, low and gravely. "Dean Winchester, what the hell are you doing out here?"
Oh, god. Oh, god, no. Dean tenses up immediately and the moment John lets go of his face, he turns around, staring up at his dad. "Dad, I'm sorry, I'm keeping an eye on Sammy, I swear I am."
"By standing out here looking like a hooker with cum dripping down your leg?"
John's pissed, Dean can tell he's pissed, and he prepares for the lecture of his lifetime and a ban from hunts for a while. He looks down at the sidewalk; he's not sorry he did it, because it's helping his family, but he's fucking sorry he got caught. He thinks about apologizing but in the end looks up, staring at his father. "I'm helping."
"Sure you are. So if something sneaks in there and grabs Sam while you're sucking some man off in an alley, you're helping? How long have you been doing this?"
"A couple of years," Dean stammers out, feeling exposed and fucking embarrassed that his dad caught him. "Since I was like thirteen. Since the first time you left me and Sam alone with no money."
"You're talking like I abused you or something."
"I'm pretty sure dumping your kids off at motels for weeks without money is abuse," Dean mutters, lips barely moving so his father won't see. He can be a rebellious little soldier, but only when John isn't looking.
There's an unhealthy pause and then a shuffle of fabric, and Dean looks up in time to see his dad pull his coat off, wrapping it around his son and starting to drag him back to the hotel. "I swear, Dean, you can be a handful but this… god, this is too much, kid."
Dean simply traipses after John, stumbling slightly in his white tennis shoes as he tries to keep up and watching as John pushes the door to their hotel room open. Sam's sleeping and Dean keeps his mouth shut; he's in the clear until tomorrow morning, at least. John lets go of Dean's arm and the sixteen year old skirts his father, peeling off John's jacket and then his own hoodie, preparing to crawl into bed with Sam when John grabs his wrist, tugging him back. Dean stares up at him for a split second, and then John's lips are against his suddenly, pushing Dean back against the tacky wall of their hotel room.
Dean's eyes widen in surprise but it definitely isn't a bad feeling. It's far from that and tentatively Dean kisses back, mouth slipping open; yes, it's his dad, but fuck if he cares. At least his dad's attractive and young; the guy he had earlier was old as hell and could hardly keep it up. John breaks the kiss after a moment, and he stares at Dean for any kind of reaction, only getting blank servitude in return. And he's not surprised; after all, Dean's been raised to follow his dad no matter what. Stockholm Syndrome at its mildest and most potent.
"You gonna go out there and sell yourself again?" he asks Dean, voice low, gravelly, almost seductive.
"No," Dean replies, and it's so obvious he's lying it's nearly painful. "Unless we need it."
"You won't. I'll leave you money."
"You always do and it's never enough."
They're close to fighting, so John kisses him again, hand gripping one of Dean's not-quite-filled-out arms tight enough to leave marks on the skin, the older man taking a step back towards the bed. His other hand goes to Dean's ass, on obvious display in the shorts he's wearing now. He manhandles his son, pushing him down on the bed and beginning to peel his black t-shirt off, eyeing Dean. "Don't give me that look, Dean Winchester. And keep your mouth shut; you want Sammy to see you like this? Not setting a very good example, is it?"
Dean stared up at his dad, feeling very, very confused about the whole affair. Sure, he had maybe had weird thoughts about his dad sometimes, but he had never expected this. His eyes flickered over John; his dad was attractive in a weird way, more charisma than anything else, and Dean swallowed, already feeling his cock hardening, pressing to the front of his kind-of-way-too-tight shorts. This wasn't fair; he was a kid, he was impressionable and horny twenty-four-seven, and John… the way John was treating him… like he wasn't his son, like he was just a hooker, just some random, underage kid he had picked up off the street…
It was getting Dean going.
John's black t-shirt hit the ground and Dean swallowed, leaning back on his elbows and watching his dad. John's jeans come off next and Dean's eyes fix on the bulge in his boxers. Oh, holy shit. Dean is more twink material than able-to-handle-huge-dick material, and his dad looks like he's hung. He stares for a few moments before leaning forward, daring to run a hand over his dad's semi-hard cock, swallowing slightly. John watches him, an eyebrow arched, and Dean licks his lips, leaning forward and pressing them to the bulge in John's underwear, sucking slightly at the already hot flesh underneath the cotton.
John pushes Dean back gently, shaking his head before sitting down on the bed, eyes fixated on Sam, the twelve year old cocooned under the covers. He's not a light sleeper, but Dean's not quiet at sex; the kid sounds like a friggin' porn star half the time, even if all he's doing is jacking off, and John knows keeping quiet will be a challenge. Another step towards becoming a hunter, if John wants to be a dick about it.
He props himself up against the headboard, spreading his legs, and the 'it's not gonna suck itself' expression on his face galvanizes Dean into action, the sixteen year old dropping down into a crouch, ass in the air. He traces the outline of John's cock, squeezing slightly before sucking at the head through the fabric, the navy fabric staining an even darker blue from Dean's administrations. The teen finally sits back on his knees, freeing John's dick from his underwear and wrapping his hand around the thick cock, eyes blown wide as he begins to jack his dad off. Chills go down his spine; this is creepy but at the same time, he likes it. For once, all John's attention is on him.
Dean moves forward, kissing the head of the older man's thick cock and swirling his tongue over it, slowly, carefully taking it into his mouth, sucking on the tip gently, green eyes focused on his father's face. John smoothes Dean's hair back, although it's almost permanently tousled, especially considering the activities he's been up to tonight. The guys are right; Dean's got one hell of a pretty mouth, and as he lowers himself further onto John's cock, his dad can't help but buck up into it.
Dean takes it all in stride, wrapping his lips around John's cock more firmly, tongue flattening against the underside as he teases the thick vein there, sucking teasingly before bobbing his head a bit; he'll never admit it to anyone but he likes this feeling. Not with just anyone, mind, but with his dad, with someone he can trust… it's great. So he goes down obediently, the feeling of John's hand in his hair the most affection he's felt from his father in a long time. He's eager to please, ass in the air as he jacks off what he doesn't have in his mouth yet, John's cock already hitting the back of his throat.
He slicks it up easily, pulling back slightly and spitting on it, jacking John off quickly. He leans forward and kisses his dad, and John kisses back, and Dean gets chills because he's been waiting for this. God, has he been waiting. He kisses back hungrily, continuing to let John thrust into his fist, and carefully, he straddles his father's lap, John undoing Dean's shorts immediately and helping him out of them, fingers ghosting over Dean's own cock, the tip already slick with precum.
Hastily, John pushes Dean onto his back, adjusting the both of them so they're under the covers; the lights are off and this way, if Sam wakes up, he won't figure it out. Dean spreads his legs, allowing John to settle between them, and there's a few agonizing moments where they have little to no contact before John's calloused hand is at Dean's mouth. Dean sucks at John's fingers almost automatically, tongue swirling over them, and John pulls is hand back far too quickly, sliding two fingers into Dean unceremoniously. The teenager is already stretched from his earlier encounter, and there's evidence of the previous experience, but John ignores it, scissoring Dean roughly, clapping a hand over the teenager's mouth as he begins to whimper.
"Shh," he hisses, pulling his fingers out and pressing his saliva-slickened cock to Dean's ass, pulling his son forward by the hips and rutting against him slowly. Dean arches his back, wrapping his arms around John's neck and pressing his forehead against his dad's. John kisses him again slowly and then pushes in, Dean letting out a whimper and arching his back. "Dean, I mean it," John murmurs, kissing him again openly. "Keep your friggin' mouth shut."
Dean nods, clamping his lips together, and John continues pushing in until he's buried in his son, holding his hips down. The covers start to slip off John's shoulders and Dean grabs them, yanking them back up over himself and his father; if Sam sees them, he'll never live it down. Plus this is cozy, having his dad this close to him, and he can pretend it's just them two, and this isn't some fucked up revenge for Dean whoring himself out. That his dad's doing this out of love.
John stays still for a moment; he might be pissed at Dean, but he's not about to fucking hurt the kid. "It hurt?" he mumbles in the dark, and it sounds way more intimate than he wants it to. Dean shakes his head slowly and John grips his hips, starting up a slow pace. Dean takes it like a pro and for a few minutes, John is pretty sure he can forget it's his first-born he's doing this with because the kid looks like such a damn hooker. "Tell me if it does," he grumbles, and this time the whisper is almost loving.
Dean nods, and he knows it won't hurt because he's not exactly Mother Theresa, but if his dad wants to act like he's caring, Dean doesn't mind at all. He kisses John slowly, grinding his hips down against John's, striking up a perfect rhythm with his dad, because Dean studies his every move and knows what John wants. This is the best sex he's had in a long time; John is firm without being rough and he's experienced as anything. He knows exactly how to get Dean off.
Within moments, Dean's panting like a bitch in heat, nails digging into John's shoulders, and his dad's trying to get him to shut up because if Sam wakes up, they're both screwed. One particularly hard thrust later, that fear becomes a reality, Dean letting out a decidedly un-Dean-like squeak and clinging to his father for dear life. John clapped his hand down over Dean's mouth but it was too late; a tell-tale rustle from the bed beside them indicated that Sam was very much awake.
"Sammy, go back to sleep," John manages to grit out, buried in Dean with a hand over his son's mouth to keep him quiet for once.
"You're home?" Sam sounds excited and John clenches his jaw, eyes fixed on the sixteen year old currently pinned underneath him. "Why didn't you wake me up?"
"Sam, I'm exhausted. We'll talk in the morning, kiddo." John dares to chance a glance at Sam; the teenager is curled up under the covers still, barely peeking out, and John decides it's safe to continue moving, rocking into Dean slowly and speaking lowly. "Your brother's still out, Sammy; I'll talk to you two over breakfast."
Dean writhes, unable to do anything, John holding him down, and the older man wraps a hand around his cock, jacking him off while continuing to muffle him at the same time. Sam makes a sound of disappointment but John doesn't care; there's never been a point where Sam hasn't been disappointed in him. He waits for his son to fall back to sleep before picking the pace up again, the bed creaking as he slams into Dean, moving his hand off his mouth. "Can you keep your mouth shut now?"
Dean nods, immediately leaning up and kissing John hard on the mouth, half to keep his mouth shut and half to get off on this. He rolls his hips down on John's cock, his father continuing to thrust into him, one hand on Dean's cock and the other on one of the teenager's hips, jacking his son off furiously, trying to finish off before Sam wakes up again. Dean spreads his legs further, burning up under the covers, sweat slicking his forehead and beading on his face, his scrawny chest heaving as he attempts to suck in adequate breaths. He feels like he's choking on air; this is amazing. This is perfect.
Consequently, he only lasts a few more minutes, cock twitching and balls drawing up as he cums, crying out into John's mouth as his dad kisses him to muffle the noise he knows Dean's going to make. His seed stained both their stomachs, beading there, and John surveys Dean for a moment before grabbing his thighs, shoving his legs up and slamming into him almost violently.
Dean is exhausted by this point, and he simply lays there, letting John use him in order to cum, and it's sexy as hell at the same time, the sixteen year old doing the best he can to get his dad to climax. John bites Dean's neck, fucking him into the mattress, and it's rough, and dirty, and Dean feels like more of a whore than usual but fuck he loves it. He loves it.
John doesn't hold out much longer, and when he cums it's with a grunt and a moan, holding Dean down as he tenses up, spilling into his son and pulling out carefully. Dean shudders at the feeling of emptiness he's left with and stares up at John, who sits up, watching Dean before leaning over slightly, meeting Dean halfway for a kiss and murmuring, "If I catch you out there doing that again, Dean Winchester, this is happening again."
Dean stares up at John and his mouth curls into an interested smirk before he shakes his head, leaning forward and looping an arm around John's neck, tugging him closer and whispering, "As long as we don't wake Sammy, I don't think I'll have a problem with that."