A/N: This is my first foray into writing Teen Wolf fanfiction. I've only watched the first two seasons and this is set in mid-season 2, except here Scott turned Isaac and there's no Kanima!Jackson.
"He's basically a puppy!" Scott said in defense of a cowering Isaac. Stiles threw up his hands in frustration, having just called Scott out on missing their bi-weekly movie night. It wasn't the first time, but that wasn't why Stiles was upset, it was that Scott had neglected to call as he'd done all previous times.
"Well, he's an incredibly needy puppy, isn't he?" Stiles retorted, glaring at Isaac, who, as Scott wasn't paying particular attention to him at that moment, shot Stiles a nasty smirk.
"Wow, Stiles, after all he's been through, especially before I bit him, you've got a lot of balls to say that in front of him." Scott glared at his best friend while he pushed a hand through Isaac's curly hair. "You all right, Isaac?" The boy nodded and looked up at Scott, his green eyes wide with—what Stiles would later refer to as—the most pitiful werepuppy look ever.
"I get that he's a puppy but that does not excuse him from this!" Stiles held up one of his sneakers to reveal a number of bite marks. "Even you weren't so much of a mutt when you were first bitten." He glared at Isaac again, only to receive a flash of Isaac's yellow eyes. "Don't give me your wolfy eyes, Lahey!"
"I hate to say this, Stiles, but I think you should go calm down somewhere that's not here,"' Scott said. Isaac made a noise, something of a purr, as Scott continued to play with his hair.
"Fine!" Stiles grabbed his jacket off the chair and moved towards the door. "I actually had something you would have been totally into, but now I guess I'll go share it with someone who doesn't bail on their friends!" Stiles slammed the front door, making both Scott and Isaac flinch.
Stiles headed down to his Jeep and got in. He racked his brain for someone who would hang out with him. Lydia was still in the hospital after being attacked by Peter at the formal and Lydia's mother had only sent Stiles away from the waiting room that afternoon. He knew Scott was texting Allison with, god knows, nothing but emojis of affection and sweet nothings that made Stiles want to vomit.
Stiles scrolled down his phone and shut his eyes, stopping on a random contact. Opening his eyes, he saw that his finger landed on Jackson. Mentally reminding himself to erase the lacrosse co-captain from his phone, he pressed the call button and waited.
"What do you want, Stilinski?" Jackson's voice—edged with the most obnoxious tone he probably could've mustered at that moment—rang through the vehicle.
"I wouldn't call you on any normal circumstances, but... are you busy right now?"
"You want to hang out? Is this some kind of sick prank, Stilinski?"
"No prank. Just wanted some company," Stiles replied lamely. "Your place, ten minutes?"
Jackson scoffed. "Fine. My parents are out anyway. Just don't let anyone see you drive in." And with that, Jackson hung up.
"Always a pleasure," Stiles muttered, pocketing the phone and turning on the ignition. It was a little less than ten minutes later that he pulled into the Whittemores' driveway. He got out of the car and stretched before making his way up to the door, which opened at that moment to reveal Jackson, clad only in pajama bottoms.
"Come in and don't touch anything," Jackson said dismissively, pulling Stiles into the house while glancing around. Once he'd shut the door, the jock turned and folded his arms across his chest. "So why the late-night visit?"
"Scott has a—" Stiles stopped and sighed.
"McCall found a new BFF, huh?" Jackson quirked an eyebrow and led Stiles up to his bedroom. "Have no fear, Stilinski, you'll find someone just as awkward and weird as yourself."
"Was that a compliment or an insult? I can't tell." Stiles sat at the foot of Jackson's bed and looked up at him. Jackson rolled his eyes and went into the bathroom, reemerging a few minutes later in basketball shorts and a sleeveless T-shirt.
"Come with me," he said, grabbing Stiles by the sleeve and hoisting him up without hesitation. Stiles groaned and unlatched Jackson's hand from his shirt, following him downstairs.
"Where are we going? Is this some kind of fucked-up torture scenario waiting to happen?" Jackson didn't respond as he opened the basement door and closed it behind Stiles. "Basement gym." Stiles nodded. "Should've figured."
"Clearly you need to work out some anger, Stiles." Jackson showed Stiles to a punching bag and handed him a pair of boxing gloves. Stiles noted Jackson's use of his name. "Have at it. And don't be afraid to punch it like you decked me that night we were locked in the school."
Stiles looked up at the punching bag and imagined Isaac's smirk before unleashing a flurry of punches upon it. He probably went off for a minute or two for the next thing he knew, Jackson had him sitting in a chair and sipping out of a water bottle.
"Damn, Stilinski, you should join a boxing club or something," Jackson commended, rubbing the boy's shoulders. "You should change into something more loose-fitting though unless you want to smell like a locker room later." Stiles pulled his shirt off and shivered a little. Jackson handed him a tank top much like his own and Stiles slid it on.
"Why are you being so nice to me?" Stiles glanced up at Jackson, who smirked.
"Because you're kind of cute when you're angry," the blond boy replied with a wink. Stiles blinked, his brown eyes traveling up Jackson's toned upper body into his piercing blue eyes. "I'd love to see how hot you are when you're pissed though." Jackson moved some mats together and pulled his white shirt off followed by his shorts, leaving the muscular jock standing in his grey briefs. Stiles felt himself harden inside his tight jeans. "C'mon, Stilinski, let's go at it."
Stiles stood up and stripped down to his own black boxers, moving onto the mat across from Jackson, whose eyes moved up and down Stiles' body, his smirk widening. "I like to do an anything goes, no holds barred kind of thing. Makes it all the more fun." Jackson took a step towards Stiles and opened his arms. "You got the first move, dork."
Stiles cleared his throat and moved quickly, circling Jackson and maneuvering him into a headlock. Jackson grunted and drove his elbow into Stiles' stomach, making him loosen up enough for Jackson to take control, pinning Stiles without so much as a second thought. Although he knew it was no use, Stiles struggled to free himself. Jackson leaned down and pressed his lips to Stiles'.
"What was that for?" Stiles asked once they had parted.
"I've had a thing for you for quite a while now, Stiles. Besides, you're the only normal guy left around here. I mean, except for Danny, but dude's not really my type." Jackson got off of Stiles and Stiles sat up, looking at Jackson wide-eyed. "What?"
"You're not gonna believe this, but..." Stiles moved in for another kiss. Jackson placed his hands on Stilles' shoulders and felt himself relax as Stiles' lips touched his once more. "I want you. Now."
"As you wish," Jackson murmured, leaning Stiles back onto the mat and pulling his boxers off.
"Never pegged you for the romantic type," Stiles teased. Jackson gave him a playful glare.
"Lydia made me watch The Princess Bride almost as many times as that dammn Notebook. You'd better not be into chick flicks or I might have to break up with you." Stiles' grin instantly evolved into a smirk. "Shut up, Stilinski."
"Yes, sir." Stiles couldn't help but laugh. Jackson lifted his legs up and over his shoulders as he positioned himself accordingly. He reached over to his discarded shorts and pulled a condom out of one pocket. "Mr. Whittemore, were you planning to seduce me?"
"Damn right I was, now shut it." Jackson tore the package open with his teeth and slid the condom onto his erection. "Ready?" Stiles nodded, feeling like a little kid on Christmas morning. Jackson slowly inserted himself into Stiles, knowing that the smaller, paler boy was a virgin, regardless of his claims to the contrary.
Stiles moaned quietly, feeling Jackson's manhood slide into him. He allowed himself to relax, except for a sharp pain which made him cry out. "Shit, did I hurt you?" Jackson looked up, worry clear in his eyes.
"First time always hurts, so I've heard," Stiles mumbled, reaching out for Jackson's hand. Jackson took Stiles' hand and squeezed it.
"I would never hurt you, Stiles... well, not like the times I have before." Jackson smiled, genuinely this time; his thrusts becoming quicker.
"So you are gay," Stiles breathed, his grip on Jackson's hand tightening.
"I wouldn't go that far." Jackson felt himself reaching climax and pulled out of Stiles to avoid the condom breaking inside the boy's formerly virgin ass. "I think I'm Stiles-sexual." He grinned at his attempt at a joke.
Stiles rubbed his own hard-on and smiled up at Jackson. "I'm not gonna be some one-time thing, right? We can go to movies and dinner and cuddle in your bed?"
"I would love that." Jackson pulled the condom off and came on the mat, leaning back, arms behind his head once more. Stiles sidled up beside him and placed his hand on his chest.
"How are we going to tell everyone?"
"We'll keep it to ourselves for now. Seems like they've got enough to worry about." Jackson placed one hand on Stiles' head, running his fingers through his hair. Stiles closed his eyes, succumbing to the sleep that had been hanging over him for a while now. Jackson held him all night.
With many deep, passionate kisses and declarations of love, Stiles and Jackson parted the next morning and Stiles returned to the McCall house, intending to apologize for his behavior the previous night. He walked through the front door and headed up to Scott's room. Stiles took a deep breath and opened the door, only to emit a silent scream and shut it again. Was he just dreaming?
"Stiles, come on, open the door," Scott's voice called. "You're not dreaming. Just come in. I need to ask you something."
Stiles slowly opened the door and slid into the room, closing the door gently. "What have you two been up to?" Isaac poked his head out from under the covers and smiled innocently. "Oh, God, how long?"
"That's not what I wanted to ask you." Scott slipped out of bed and put his boxers on. It was far from the first time Stiles saw his best friend naked and he knew it was far from the last. "You're hiding something too." He walked over and put his hands on Stiles' shoulders.
"I— I came back to apologize for overreacting last night." Stiles tried to calm down; he knew Scott could read how he felt through his heartbeat and cursed this supernatural ability.
Scott proceeded to sniff him. "Man, that is still super weird," Stiles mumbled.
"Were you with Jackson?" Scott straightened up, smirk firmly in place. Stiles looked over at Isaac, who shared the same look as Scott.
For the first time in recent memory, Stiles was at a loss for words, which only confirmed Scott's suspicions. "You finally lost your virginity, dude!" He clapped Stiles on the back and pulled him over to the bed, where he now lay between Scott and Isaac.
"And I take it you two lost yours last night?" Isaac replied with a soft nudge with his nose to Stiles' arm. "Oh, I see, now you're affectionate."
"Just relax, Sti. He's pretty good when you get to know each other and he gets that you don't pose a threat." Scott put an arm around Stiles. "Any chance of a foursome?" Isaac sniggered.
"You're sick! You're both sick, you know that!"