This is pure PWP, so if you're looking for something with depth, seriously, you're barking up the wrong tree here.
He hissed in a breath as teeth clamped down tightly around his shoulder. The push of hips against his ass, grinding and dragging against the fleshy globes practically had his cock dripping. The harsh breaths moistening his heated ears, the soft moans coming from behind him, went straight to his head and made his cock twitch against the comforter beneath him.
This thing was all sorts of weird. At first, he thought that he was going crazy. That maybe after Derek had turned him, some of the Alpha had bled into him and he secretly liked the annoying human in their group. But every time Jackson got within ten feet of Stiles, his wolf mewled and whimpered, pawing at its cage and aching to roll over and show its belly to the human.
It'd all come to a head not long after the feeling had popped up. He'd cornered Stiles in the locker room, prepared to pummel the boy for whatever he was doing to him – because surely it was something supernatural and weird – but then Stiles had shown his backbone once more, wheeling Jackson around in a deflective move and pinning Jackson to the lockers. Jackson had felt his cock swell in his loose shorts, licked his lips as he pressed his hips further into the lockers to feel the cool metal against his hot length.
Stiles had chuckled deeply in his ear, head craning around to see the effect he was having on the wolf. He made an entirely Stiles quip before shoving Jackson even harder into the lockers, making sure his hips brushed against Jackson's backside long enough for the blond to feel that he was half hard too.
After that, Stiles regularly caught Jackson whenever he would watch him, wondering what the brunet's talkative mouth could do to him. To his mouth, his neck, his dick, his ass. It became an obsession when he took notice to how much Stiles licked his lips, became dreams at night where Stiles would lick him open before fucking into him in one smooth movement, pushing harder and harder until Jackson would fist the sheets and beg.
But this, this was better than anything he'd ever dreamed. Stiles had shown up at his house, pushed him inside to the closest wall and attached their mouths until Jackson was breathless and panting.
Jackson felt like he always had to be on. Best at lacrosse, tried to be the best in his classes, tried to do everything because there was always that adopted kid's fear in the back of their head that one fuck-up, one disappointment, and he'd be shipped back. Part of him knew it was irrational and unlikely to happen at 16 years old, but he couldn't help it.
He thought becoming a werewolf, becoming something better, would fix that. He thought that he'd be able to breathe while still holding up to everyone else's expectations of whom and what he should be. But instead, he found out that while Stiles had him pinned and rocking his hardness straight into Jackson's hardening self, that all he wanted to do was roll over and let Stiles do to him whatever he wanted.
Maybe that was the better. Because as Stiles' hand grasped the back of his neck and the other one bruised his hip, slowly sinking every thick inch of himself into Jackson's body, he felt all the tension that'd accumulated over the last decade start to fade away.
The only pressure he could feel was the foreign feel of Stiles' dick spreading him wide open, the burning pain healing itself almost instantly so that all he felt was full and pleasure.
A string of uhn and gah and unfinished curses spilled from the lacrosse captain as Stiles snapped his hips forward, pressing balls deep into Jackson's ass over and over while he was pressed even further into the bed by Stiles' grip around his neck.
"You look so pretty like this." Stiles grunted as his hips hit a spot deep in Jackson that made him arch his back and press back in desperation. "You sound so needy, feel so tight. Who knew Jackson Whittemore," he paused, buried to the hilt and pulling out only enough to roll his hips as he laid himself against Jackson's back, "Would be so easy to get to roll over."
Of course Stiles would talk during sex. But instead of the normal reaction it caused within Jackson – shutting him up with threats or with violence – he instead found the words causing him to squish an arm beneath the heavy weight of their bodies to encircle his dripping length and pull.
"I might be able to tolerate you more," Stiles' voice was getting tight, speaking through gritted teeth as he worked to get them off, "If you were always like this: fucked out and incoherent." He sounded proud of himself as his teeth marked and soothed at Jackson's shoulder blades while he pulled away from his back.
When Stiles pulled out completely, Jackson whined in protest. Fucking whined. He wished he could blame the wolf, but Stiles' cock seemed to be like catnip for the bastard and he was still rolling around happily despite the interruption. Stiles' hands were on his thigh and shoulder, flipping the bulkier teen onto his back with no problem.
Jackson lay splayed out, his erection bobbing in the air and begging for attention as Stiles licked his lips. He wanted to know what that mouth would feel like, how it would look to see Stiles nosing the base as he swallowed him. He wrapped his hand around himself as he thought about it, jerking and moaning as he watched Stiles bite his lip.
He'd tilted his head back, mind forgetting for the moment that all he had to do was flip Stiles easily, turn the tables as he sat on the younger boy's chest and rubbed the head against those loose lips and sink in, right into that wet, hot mouth and blow his load right into his throat.
He was so immersed in that, that he nearly did blow his load when the flat of a tongue suddenly licked from his fingers at the base to the weeping tip. Jackson's eyes shot to where Stiles looked up at him from between his legs, tongue lapping at the precum like it was a lollipop. He almost wept when Stiles sucked the head between his lips, the rough of his tongue pulling at the slit.
Jackson wanted to protest when Stiles pulled away, gathering Jackson's legs up against his arms and stretching them out as he lined back up and sank into Jackson's body all over again.
"Fucking Christ, Jacks." Stiles moaned, his forehead resting against Jackson's collarbone as he felt the brief resistance and rippling in the entrance he rested in.
Jackson's blunt nails dragged down Stiles' arm, his tongue tasting sweat and something weirdly Stiles in the other's shoulder as he waited, impatiently, to be fucked into a blissful completion by the human.
Stiles' thrusts were slow and shallow when he finally moved, slowly sinking further in as he continued on. His head lolled on Jackson's shoulder, his mouth pressing sweetly against the other's neck, traveling upwards until their mouths lined up perfectly.
Jackson thought that it might be his cock he tasted on Stiles' tongue as they slipped together, the idea making him reach for his neglected member when Stiles began to drive into him harder and faster.
He could feel Stiles' own cum slicking the way for him to press further into Jackson, deeper than before they'd switched positions. The normally quiet and controlled part of him shattered into oblivion as Stiles dragged over his prostate with each thrust, making him squeeze his eyes shut and let out the most embarrassing half moan, half whimper each time.
"Please." He finally begged, sounding broken, unable to stop himself from repeating the word every time Stiles bottomed out. He slipped his arms underneath Stiles', grabbing onto his shoulders as he was fucked, the thrusts losing rhythm as he worked.
Jackson could feel it building, could feel something ten times better than anything else he'd ever felt swelling deep within him as his balls tingled. He watched as Stiles pulled back, sitting up on his knees as he drilled in, his head thrown back in bliss while his hands pressed flat against Jackson's thighs to keep his legs in the air, muttering about how good Jackson felt, how tight he was, that his ass was better than Disneyland.
Jackson whined, his hand gripping tightly and working himself in time with Stiles' erratic thrusts, his body pulling tight like a bow until he snapped with a loud grunt turning into sobbing breaths as he shot up his chest harder than he'd ever come before in his life.
"Fuck, fuck, fuck!" Stiles cursed, pushing shallowly into Jackson's tightening channel until he sunk all the way in and unloaded himself into the warmth.
Jackson grunted, one more shot of come dripping out as he felt Stiles lose himself within his body. It was weird and oddly hot, in every sense of the word, to know that Stiles had just emptied his dick straight into Jackson's ass.
Stiles' arms were trembling as he released Jackson's legs, letting them flop bonelessly to frame him as he lowered himself slowly until their torsos stuck together with sweat and cum.
Jackson panted out his breaths, his head feeling dizzy like he'd been holding it for too long, and wrapped an arm around Stiles' back. He had no idea what they were supposed to do next (but sleeping sounded viable) and he couldn't bring himself to care too much as Stiles licked at his chin where he'd managed to get a bit of his cum on the first shot.
He groaned at the action, watching as Stiles' tongue licked all around his mouth like he'd just finished the best treat he'd ever had. Stiles used what little energy he had left to pull himself up until their flaccid cocks rubbed together, their moans getting lost in a kiss.
Jackson finally got to flip them over, the wolf in him wanting to be the one to take care of Stiles like he'd just been taken care of, but he didn't know what to do. He wasn't like Stiles, who probably researched the ins and outs of gay sex before showing up on his doorstep. He was clueless. He'd probably have to have an awkward 'I got fucked by Stiles Stilinski, teach me how to be gay' conversation with Danny sometime during the weekend.
"You have the most perfect cocksucking lips I've ever seen." Stiles moaned as his thumb brushed the thick swell of Jackson's lower lip.
Or maybe Monday morning, Jackson thought as he trailed kisses down Stiles chest, their eyes locked as he headed for the cock slowly hardening against his abdomen.