**AU in which Jackson works at an underwear store and doesn't know any other characters**
"Maybe we shouldn't go," Stiles said nervously. "I mean, they aren't that bad."
Scott lifted the hem of Stiles' shirt and grabbed the waistband of his boxers, pulling them from his hip into better view to accent his point. "Don't you wanna impress Isaac? Maybe he'll notice you in the locker room, now. But these are fine, if you want to die a virgin. Seriously, Stiles, how much did these cost?"
Stiles' face turned even redder as he glanced at the people walking by on the street, embarrassed to have his hip exposed. "I dunno," he said, "maybe two dollars?"
"Two dollars!?" Scott said, pulling the cheap material further out of his pants to better examine them, and further expose the boy's pale skin. "Stiles, it's time for an upgrade."
When he saw the edge of his pubic hair exposed, Stiles ripped his underwear from Scott's hand. "Fine, let's go in," Stiles said, angrily pushing the glass door open.
The underwear store was basically what Stiles expected, consisting of a small room with racks of underwear lining the walls and weaving small aisles, a counter with a cash register, and a row of doors leading to small changing stalls. Only a few patrons were wandering around the store, looking at the rows of colorful underpants in all shapes and sizes. A bored-looking cashier in khaki shorts and a red polo stood behind the counter; both Scott and Stiles had seen him around school a few times. His name tag said Jackson.
Stiles followed Scott's lead, walking through the aisles and taking the various kinds of underwear that were handed to him. His cheeks reddened as the pile got higher, looking at the things that Scott expected him to try on. Some of them weren't much more than a few strings. When they finally got through the entire display of underwear, Stiles had four pairs. Just as they were asking the clerk to unlock the door to the fitting room, Scott's jaw dropped. He picked up a silver thong made of some material that looked almost like rubber, but was soft to the touch. The overall effect was something shiny and silver, but clingy enough to leave nothing to the imagination. "I have to try these on," Scott said with a smile, picking up the silver one as well as gold and bronze.
"But how will I know what looks good?" Stiles whined. "I'm not even sure how to put all of these on."
"Er, not to be too forward," Jackson, the cashier, chimed in, "but I would be happy to lend an opinion. I end up doing that a lot, so I think I have a pretty well developed sense for these things."
"Perfect," Scott said with a smile, disappearing into one of the stalls.
"I'll wait here," Jackson said reassuringly, standing by the door as Stiles nervously went into one of the stalls.
"Should I keep on- erm, I mean..." Stiles muttered through the door, confused.
"You can leave on as much as you like," Jackson said professionally.
"Oh just take it all off," Scott yelled to the boy. "Stop being such a wimp."
Stiles turned red as he stripped totally naked, feeling almost aroused at the knowledge that nothing separated him from the outside but one large wall and three shorter ones. He could stretch to see over or crouch to see under them, probably for security reasons. Blushing at the thought of peeking at his best friend naked, he picked up the first pair. They were fairly normal; a pair of red briefs with little Marvel comic strips on them. He slipped them on, smiling. They did look cute, showing off his slender figure instead of making him look gawky, like the boxers usually did. Turning around, he noticed that he actually had a nice ass as well. He stepped out of the stall, feeling confident and sexy as he showed off his underwear to Jackson.
"These are nice," the clerk said, watching the boy spin. "The red looks good with your complexion, and the fit frames your legs and torso nicely. And the print is fun and kind of nerdy."
Stiles smiled, satisfied as he went back into the stall, taking off the briefs and putting on the next pair. The sign above the display for this pair called them 'sport briefs.' Stiles' feelings of embarrassment returned as he looked at himself. He'd never particularly considered himself sexy, but these made him look the part. They were a dark orange, and rose high on his legs, accentuating his package (which looked surprisingly big) while covering his entire ass. He stepped out, feeling a little more awkward than last time as his exposed body was evaluated by the cute clerk.
"Oh, wow," Jackson said as he watched the boy turn, showing off the skimpier underwear. "These are a totally different effect. They're more... sexy."
Stiles nodded and quickly ran into the changing stall, deciding to buy them. If someone as attractive as Jackson thought they made him look sexy, there was no way he'd give them up. The next pair didn't feel quite right as he slid them on. He was hesitant in the first place about trying on a thong, and this black pair made him feel somehow wrong. The back felt fine, with the material sliding pleasantly into his crack, but the front felt too big, yet it rose low on his pelvis, exposing some pubic hair. He stepped out, fighting the urge to cover himself.
"Hmm, these aren't quite right," Jackson said, standing to look at the boy as he did a quick spin around. "They need to be tighter and higher in the pouch." Jackson grabbed the waistband, his hand grazing through the boy's pubes, and pulled up. The material stretched around his balls and pulled on the portion wedged into his ass. Jackson grabbed the boy's sack with the other hand. "A better pair would fit more like this, accentuating your-"
Jackson stopped short, realizing he was fondling the cute customer that had agreed to give him a show. Ripping his hands away from the boy, he turned red. "Well anyway, don't you have one more pair?"
Again, Stiles nodded as he went into the stall, taking off the thong and putting it in a corner. He looked at himself in the mirror for a moment. He was red from head to toe, the feeling of the hot boy's hands on his skin still burning. His cock had grown a bit, plumping out from the pleasurable closeness. Stiles took a deep breath, trying to calm his heart rate as he picked up the next pair. They were even smaller, and had some strange piece of metal on them. He had no idea where any of the various strings went, much less what to do with the metal bit. "Uhm, Scott, how do I put these on?" Stiles yelled from the stall.
"Hang on, I'm naked at the moment," Scott yelled back. "Uhm, Jackson, was it? Could you help him?"
Before Stiles could protest, the model-like boy was in the tiny room. Stiles covered his cock with one hand, handing over the underwear for inspection to the clerk. "Oh, yeah, people have problems with these sometimes," Jackson said, arranging the little straps of teal material. He bent down and stretched out one leg hole, which Stiles stepped into, then the next. Jackson rose them half way up the boy's thighs before the boy realized that he would have to expose himself. Reluctantly, Stiles withdrew his hand. Jackson pulled the underwear up, stretching one string into the boy's pale ass. Stiles could've sworn he felt a gentle caress on his ass cheek, but he couldn't be sure. Suddenly, Jackson grabbed Stiles' cock and balls in his hand, squeezing his half-hard cock through the circle of metal. Stiles was speechless, his body turning a shade of red darker than he'd ever turned before.
"It's called a cock ring," Jackson explained, noticing the boy's reaction. He pulled a pouch of material over the boy's exposed half-boner. "It keeps the blood from leaving your dick."
Stiles, still stunned, turned and looked at himself in the mirror. His pale body was deeply red, with his cock straining against the teal material covering it, leaving absolutely nothing to the imagination, and his pubes totally exposed. He looked at the clothed boy standing close behind him, and saw that his blue eyes taking in the nearly-naked boy's form hungrily. Then Stiles noticed the boner tenting his khaki shorts. With a smile, Stiles turned around.
"So what do you think of them?" he asked the clerk, giving a quick turn around. "Are these any good?"
"Er, yeah, definitely," he said, looking up and down the lithe form. Stiles' stomach plummeted as he took the first step, unzipping Jackson's pants.
"So what do you wear, since you work here?" he asked, unbuttoning the khakis. To his surprise, Jackson wasn't wearing any underwear at all. His long cock sprang out from his pants, pointing at Stiles. The boy grabbed the hot meat, giving the seven cut inches a few good jerks. Jackson moaned under the boy's touch, his nerves sending shocks through his body. He leaned against the door, unable to stay standing while the pale boy stroked him. Scott crouched down, peering from under the wall between their stalls. His brown eyes widened as he saw the erotic scene taking place in front of him.
"Damn Stiles, you look good," Scott said, looking at his best friend in the skimpy underwear. "Need some help?"
Stiles grinned at him mischievously. Scott took this as an invitation, sliding into the next stall. When he stood, his hard cock was already tenting the bronze thong, every line and vein visible through the metallic material. He set about removing Jackson's shirt, pulling the ugly red polo over his head and tossing it in the pile of Stiles' clothing. Stiles repositioned himself and everyone else in the tiny stall, moving so that he was on his knees, back pressed against the door. Jackson was facing him, his dick in the boy's mouth. Behind him, with his back pressed against the far wall, Scott was on his knees, pressed against Jackson's back with his face buried in the boy's ass. Scott pulled the pants off of the boy's ankles, tossing them aside as he pressed his tongue harder into the hole. Jackson moaned as his prostate and cock were both stimulated by the boy's mouths. Stiles deep-throated the dick, barely managing to catch his breath between thrusts. Jackson continued to press harder and harder into the boy's mouth, caught up in the dual sensations as he thrust backwards onto Scott's tongue and forward into Stiles' mouth. Eventually, Scott's tongue was replaced by his fingers, probing the prostate as he swung back, then teasing his hole as he thrust into Stiles. Stiles pressed his back harder and harder against the door, his breath getting more difficult to keep up. It was like he was being skullfucked by Jackson, and the more he pulled back, the harder the clerk pushed.
Suddenly, the door gave way. The three boys tumbled out, one on top of the other, before rolling off of each other. They stared up at two boys as Danny and Isaac stared down at them. The pair was shocked at the site before them; three guys from school were lying on the ground, Scott's fingers up Jackson's asshole, and Jackson's cock wet with Stiles' spit. Jackson was naked, and the other two were hard in very skimpy underwear.
Stiles immediately turned red when he saw that Isaac was watching him, nearly naked as he gave head to some guy. Scott took a different view of the situation, glad the boy he'd been flirting with could see him in such a hot situation. The entire reason that the two had come was so that Scott could impress Danny and Stiles could impress Isaac. Then both boys noticed their crushs' hard ons. Danny and Isaac had both been listening in on the hot scene, rubbing themselves through their pants.
Scott pulled his fingers from Jackson's ass, getting up to kneel in front of Danny. He pulled the boy's pants and underwear down, revealing his seven and a half inch boner before shoving it in his mouth. Stiles watched for a moment before following suit with Isaac. Both recipients seemed too shocked to respond. Jackson, feeling left out, crawled between the pair of cocksuckers. He flipped the black material off of Stiles' hard cock, slowly impaling himself on it after the boy turned his body to the side. Leaning forward, Jackson pulled down the bronze thong, eating the boy's hard, tanned dick. Now Isaac and Danny were standing next to each other, getting their cocks sucked by Stiles and Scott, whose bodies were turned to the side so that Jackson could impale himself on their cocks, creating a sort of U shape of fucking.
Jackson came first, rubbing his hard on while he forced Stiles' dick against his prostate. His load of jizz sank into the cheap carpeting. Shortly thereafter, Stiles came in the boy's tight ass, spurting loads into him. Jackson slipped the stick cock out of his used asshole, focusing on Scott now. Scott quickly came into the boy's throat, now that all of Jackson's attention was on his cock. He was deep throating the boy, so Jackson never even tasted the hot loads as they dropped into his stomach. Isaac and Danny came at the same time, filling their boys' mouths with cum as they shuddered.
All five boys collapsed on the floor, breathing hard but smiling in their various states of undress. Scott, who was lying with his head on Danny's broad chest, looked up at the boy. "So... you wanna go out sometime?" he asked with a laugh.
Danny laughed in return. "Of course," he said, sliding a hand down the boy's muscled back to his smooth bubble butt, grabbing a handful.
Isaac, who was lying face-to-face with Stiles, his hand on the boy's creamy, exposed hip, smiled as well. "You think that you'd want to go out with me sometime?" he asked, actually seeming almost nervous despite the intimacy that they'd just shared.
Stiles blushed again, the ruddy color reaching down his chest. "Definitely," he muttered, almost embarrassed.
"Jackson," a voice buzzed from the changing room. The naked boy scrambled over to where his pants lay.
"Yes sir?" he said into the radio clipped to his khakis.
"Can I see you in my office for a moment?" the voice said in a tone that conveyed controlled anger.
"Right away, sir," Jackson said, gathering his clothes.
"And Jackson," the voice buzzed once again, "don't bother changing."
All five boys looked at the radio. Jackson's stomach dropped as the other four giggled behind him.