At Jackson's House

This was the most humiliating day of Stiles's life. Swallowing cum from two guys in the locker room with a smile before lunch. Walking home in a shirt with cum and spit all over the inside of it. Then Googling what the hell a douche bulb was-and USING IT. When he got to Jackson's door, he noticed a note stuck to it.

The door is unlocked. Losers welcome upstairs.

Stiles walked in with a sigh. When he went upstairs, he found a horrifying sight. A trail of red stuff leading to a door. It would be better if it was blood, but...worse. It was rose petals leading to what was presumably a bedroom. Following them, he opened the door and found Jackson on the bed. It wasn't surprising that he was naked. What was surprising was the rose petals on the bed and the candles strewn around the room.

"Ready to lose your virginity?" Jackson asked with a smile.

Those words hurt more than a punch. A punch would probably be preferable. Stiles decided pathos might be the best course of action here. "Jackson, is this really what you want? I get you can be an asshole-"

"Interesting word to use in this situation," the jock laughed. "Excited for what comes next?"

"Jackson," Stiles pleaded. "Please don't do this."

"It's normal to be stressed," Jackson said. "It's a big moment, but I promise I might be gentle."

Sighing, Stiles sat on the bed. "What..." He took a deep breath. "Why are you doing this?"

"Because I want to," Jackson stood and strode over to his couch. "You're wearing way too many clothes." He looked at where Stiles sat on the bed. "Why don't you stand up on the bed and do a strip-tease?"

"Hell no!" Stiles exclaimed. "I'm not doing that."

"We both know you don't really have a choice here," Jackson laughed. "Do you need some music to get you going? Or I can get some singles, if you want."

Sighing, Stiles kicked off his shoes and stood up on the bed. Under the jock's gaze, he got uncomfortable. There couldn't be any situation that would make him more self-conscious. But maybe this was like the blowjobs. Do a good job and Jackson would get off way faster than he intended...and he'd be free to leave while the other boy was too blissed out to even notice. So, he started with his jacket. He pulled it off slowly, freeing his arms. When he threw it off to the side, Jackson clapped.

"Whoop!" He hollered, far louder than necessary. "Take it off, bitch!"

Stiles rolled his eyes, bringing his hands to the bottom of his t-shirt. Pulling it up to reveal his stomach and treasure trial, he noticed Jackson (for all his talk about only doing this because he could) was looking at him pretty intently. His eyes were hungry as hell, which spurred Stiles on a bit. He lifted his shirt slowly, revealing his stomach, his nipples, then pulling it up over his head. He thought, what the hell? He threw his shirt to Jackson, who caught it with a grin. Then Stilinski reached for his belt, taking it off quickly. He unbuttoned his jeans, sliding down the zipper.

Jackson still stared at his every move. So Stiles reached down to pull off his pants, lifting a leg when he needed to slide them off. When he threw them to another side of the room, Jackson still stared at him. "Everything," Jackson said.

Stiles pulled down his boxers, fighting the urge to cover himself with his hands under Jackson's scrutiny. "Jackson, I..." Stiles began. "I'll suck you off however you want me to. Best blowjob in the world, as long as you want. Just..." He couldn't even say the word. "I don't wanna get fucked tonight, maybe you-"

"It's not about whether you want it or not," Jackson said. "Hands and knees on the bed."

Stiles panicked internally, wondering how this was going to feel. No way would it be pleasant. He heard a sound like plastic being ripped that was-oh lord, it was a condom. Stiles sat there, dreading what would come next until he felt the bed shift under him. As Jackson kneeled behind him, he closed his eyes. When he felt something warm at his hole, he shouted, "WAIT NO!" The jock's hands grabbed his hips to keep him in place when he tried to crawl forward. Stiles turned around, meeting Jackson's amused eyes. "Don't you have to do something to get me ready first?"

"I put some lube on my dick, you'll be fine," Jackson sighed.

"Maybe," Stiles said, "maybe, I can just finger myself for a little bit? I'll even suck-"

"Nah, I'm ready now," the blue-eyed boy said. He reached up to push Stiles's head so he was facing forward again. His hands tightened on the sheriff's son's hips as he leaned forward to whisper in his ear. "And you better act like you're lucky to have my dick inside you. If you don't convince me you're having a good time, there won't be any need for me to be gentle," He chuckled as his hands moved to spread Stiles's hole open. "Will there?"

Stiles closed his eyes, the anticipation killing him. He didn't have to wait long. There was something hard at his hole, a scream coming from his throat as Jackson's cock entered him. The jock had an extremely thick dick, so his hole felt like it was on fire as it was stretched open. Even though Jackson went slow, moaning the whole time, as he pushed his dick in...it didn't help. "Ahhhhhhhhh!" Stiles screamed, trying to pull away to get it out of him. But Jackson had his hips in a vice-like grip.

"That doesn't sound like you like it," Jackson chastised. He thrust his hips forward quickly, tears springing to Stiles's eyes as the pain got a thousand times worse. Now, not only was his hole stretched to the point that it felt like he was being ripped in half. He also felt Jackson's dick in the deepest parts of his ass, the sensation overwhelming. Jackson began to thrust his hips and Stiles reached around to place a hand against the other boy's abs.

"No, no, nono nonononononononoooooh," Stiles begged. "OW-AHHHA-I love it. It feels so-ooooh shit-so good, just please go slow-OH! Please, Jackson!" Jackson withdrew his hips slowly, Stiles finally getting a chance to release a breath. Then his hips shot forward, cock filling Stiles again as the other boy screamed. "SHIT SHIT SHIT! Please go slow!" He yelled.

When Jackson pulled his dick back again, Stiles tensed up. He wondered if Jackson would snap his hips forward again. But he didn't. "What's your favorite thing about it, Stiles?" He taunted. "Since you like getting fucked so much."

"Ha-ah-huh-haaaah," Stiles whimpered, trying to form the words as his hole still cried out from the stretch of Jackson's cockhead. "I-I-aaaah...I love everything about getting fucked," he breathed. "I'm-huuuuh." He took a breath, still adjusting to having the other boy inside of him. "I'm such a-ugh-slut."

"Oh?" Jackson started to move, slowly this time. His dick pumped in and out of the other boy, his pace gentler now. "All this time you kept saying you weren't a slut. What changed."

"I've-ooooohwaah-gotta admit it," Stiles lied, face still betraying how much pain he was in. Jackson's cock completely filled his ass, moving in and out slowly. But maybe if he could help with Jackson's little power trip, he'd cum faster. "Aaah, I was made to take a dick in my ass. It's all I want, I-aaaaaye-I don't know why I didn't realize it before-uuuhhhhhhh."

"You really were made for this," Jackson moaned, his fingernails digging into Stiles's hips. "You're so fucking tight, I don't know why I wasted so much time on your mouth. Those blowjobs sucked."

"Literally," Stiles laughed to distract himself from the pain. "I loved sucking your dick, I'm such a whore, but-AAAAH!" Stiles moaned in pleasure as he felt something in his ass. Jackson's cock moved in a way that brushed against something sensitive. He arched his back, the sensation traveling straight to his dick as he felt it start to harden.

"Ngh! You like that, slut?" Jackson asked. His cock brushed against that spot again as he withdrew it.

"Yeeeeeeeessssssssssssssssss!" Stiles breathed. When Jackson hit it again, he moaned, "fuck, Jackson, yeah." He hated it. Literally hated it, but it felt so good. When he focused on the pleasure, he felt himself finally relax, his hole easing up a bit around Jackson's dick. He even began to feel himself get fully hard, which almost never happened during his visits with the jock.

"Yeah, there you go, bitch," Jackson groaned, smacking Stiles on the ass. He moaned in response to the hit, his hole clenching around Jackson's dick for a moment before relaxing as he felt Jackson against his prostate again. Jackson hit him again, moaning at the way he could control Jackson's hole with a little pain or pleasure. "You like that dick hitting your spot, slut?"

"I love your big dick, Jackson," Stiles said, still worried Jackson would start pounding him too hard and too fast again. "It's so fucking perfect."

"I can tell," Jackson reached around to grab Stiles's dick. "I knew you'd get hard, you little whore."

Stiles shut his eyes, lost in the sensation of Jackson's cock hitting his spot. It felt amazing. Ten times better than jacking off. Even the stretch of his hole around Jackson's unnecessarily thick dick became bearable with the stimulation to his prostate. "Jackson," he moaned. "Egh! Aaaaaahaaaaa..."

Jackson was more preoccupied with admiring the red handprints on both of Stiles's ass cheeks. He grunted, pounding Stiles faster and faster. Not that the boy could've possibly noticed with how he'd become a moaning mess. All it took was a few well-aimed thrusts that brushed against his prostate and Stiles lost his ability to be a smartass. He just moaned and groaned recklessly, sometimes even thrusting back against Jackson's dick of his own accord. Jackson still had his hand wrapped around the other boy's cock, pumping it. Stiles desperately thrusted in and out of his hand, which helped since it meant he started to ride Jackson's dick on his own.

"Oh fuck," Stiles moaned.

"Come on, slut," Jackson flipped around on the bed, lying back down and pulling Stiles up a bit. Stiles straddled him, facing away from the jock. When Jackson wrapped a hand around Stiles's dick, the boy started to move his hips. While he continued to chase the friction, he rode Jackson's dick. "NGH! Damn you're a whore," Jackson breathed.

"Aaaah-I'm," Stiles grunted, "I'm a whore. Please..." He couldn't finish the sentence, his mind too busy making sure he rode Jackson's dick in a way that had it brushing against his prostate as often as possible. By now, he didn't even really mind either way if Jackson started to pound him like crazy. But..."Fuuuuuuuuuuuuuuuuuck, I'm a slut, Jackso-uuuuhhhhh. I love your dick, it's so big."

"I know you love it, you little cocksluuuuut," Jackson moaned, still holding Sitles's dick as the boy continued riding him. "If you like it so much, keep riding it."

"Oooooo, I..." Stiles breathed. "I'm gonna-aahhh-cum."

"You're gonna cum from my dick?" Jackson groaned. "Fwooo, you like it that much, bitch?"

"Yeahhaahhahaaah," Stiles moaned, hips moving faster and faster as he rode the other boy. "I...DAMN! I'M GONNA CUM! SHIT!"

"CUM YOU FUCKING SLUT!" Jackson yelled. And Stiles did, his dick twitching in Jackson's hand. Even though he was facing the opposite direction, the jock could tell everything that was going on. He could feel the spasms from Stiles's cock as it pumped out his cum. He could feel the drops of cum that flew down to his toes and likely all over his bed. He could feel the drops of cum that came after those big shots and ran down his hands. He could hear the moans.

"AaaahahaahahaafuuuuuckkkuhhhhhhoooohhhhshiiiiiittaaaaaaaahaaaaahaahahaaahaaGODDAMNeeeeeeyyyyehuuuaggh!" Or something like that. And, worst of all, he could feel the way Stiles's hole-which was already tight-started clenching tight enough to milk the jock. It got to the point that Jackson didn't even know he was cumming until he felt Stiles's hole get even warmer around him and a wet sensation make it easier to slide in and out.

"DAAAAAAAAAAAYAAAAUHAAAAM!" Jackson groaned as he realized he was cumming. Then he noticed how much his dick was twitching, cum shooting out of it straight into the other boy's hole. Stiles's ass was absolutely flooded with cum. "SHIT!" Stiles continued to milk his cock, the boy riding him faster as he continued to chase that glorious prostate stimulation. But it became too much for Jackson. His dick was so sensitive after his orgasm that he shoved Stiles off of him. "God you're a desperate slut."

Stiles just moaned, enjoying the feeling of fullness for a while. As he slowly came down from his state of bliss, his eyes shot open. Did I just, he thought. He looked around, searching for his clothes.

"You might as well get dressed," Jackson laughed. "Should've gave it up to someone else if you wanted to cuddle after."

Stiles practically ran for his clothes, putting on his underwear, jeans, shirt, jacket, and shoes in record time. "I'm..." He began. Then he decided against announcing it.

"Oh, there's something I need you to do," Jackson said. When Stiles looked at him, Jackson was wearing a grin that wasn't comforting in the slightest. No, it was actually completely horrifying. "I'll text you later. You'll love it."

Hours Later

Stiles showered for a long time that night. His ass was sore. His hole and his asscheeks were crying out in pain after getting spanked and fucked all night. By the time he was sure he'd washed out all of the Shithead's cum, he got out. Heading to bed without clothes on, he heard a chirping sound. When his phone lit up, he grabbed it. The text he got shocked him enough that he doubted he'd be able to sleep tonight.

Shithead:

hook up with scott

you've got 3 days, slut XD

AN: You're such a freaking troll, Jackson. Lol, leave him alone.