Chapter Text
“Dude, you’ve got to stop shipping lingerie to my house,” Scott said upon arriving at the library.
Stiles— who had been sucking the cap of his highlighter, studiously reviewing his notes for finals— choked. He hacked up the green cap right before he accidentally swallowed it.
Across the room, the librarian shot them a foul look.
Stiles wiped the spit from his mouth, sent her a sheepish smile and a wave. “Scott,” he hissed when she looked away. “Time and place.”
Scott looked on, unrepentant. He shoved Stiles’ books to one side to make room for his laptop. “I’m sorry, is there a correct time to talk about your freaky sex stuff showing up at my door again?”
“There’s probably a better place than our school library, when Mrs. Jones is like five feet away.”
“Did I mention my mom opened a box full of panties this morning?”
Stiles blanched. “I told you I had a package coming!”
“You said it was coming tomorrow.”
“I—“ Stiles thought back to the conversation. “Yeah, I might have said that.”
“Stiles! This is the second time! She thought it was Derek’s, some of his stuff that he’d shipped out ahead of him.”
“What did you say?”
Scott moaned, head in his hands. “I had to lie again and tell her I bought them for Allison.”
Stiles breathed out. “Oh, okay, cool.”
“Cool? There were like twenty pairs in there! My own mother thinks some panty obsessed pervert!”
“Ouch.”
Scott rolled his eyes, sighing. “You know what I mean.”
Yeah, Stiles knew exactly what he meant.
It stung a little.
“Hey, let’s not forget you agreed to let me send it there.”
“Yeah, but that was when it was, like, skirts and tights and earrings— back when you had gender identity issues, bro. Now it’s like…” Scott whispered, eyes wide. “A sex thing.”
“It’s not only a sex thing,” Stiles argued. “I’m just a dude who likes wearing skirts. I don’t know what you want me to say.”
“I want you to say you’ll stop sending underwear to my house!”
“Scott, come on! Imagine if my dad, the Sheriff, had found that box. I don’t even know what he’d do!”
“Then stop ordering them! Don’t you have enough?”
“You two,” Mrs. Jones snapped from behind them. Both boys jumped. “People are testing next door. Keep your voices down.”
A chorus of yes, ma’ams. Once she walked away, Stiles leaned over the table again.
“How about this— from now on, I’ll make sure whatever I get arrives while your mom’s at work.” Scott looked unconvinced, so Stiles tacked on, “and I’ll be less frequent. Just once and awhile, every couple of months.”
Scott considered it. Finally, he groaned in acquiesce. “You so owe me, dude.”
Stiles fist pumped. “Have I mentioned you’re the best best friend in the whole world yet today?”
“I feel like I’m enabling an addict.”
“Boys! Quiet!”
They ducked their heads, and got to work.
-
A couple months went by. Stiles and Scott both graduated, not with honors or anything fancy— but they finished. Stiles even did well enough that he got into University.
Scott, on the other hand, was sentenced to his first year at Beacon Hills Community College to build up a GPA. Melissa and Peter weren’t exactly thrilled, but that was to be expected. Scott had long since been placed in the impressive shadow of Derek Hale.
Derek Hale, as in the bad-apple-turned-prodigal-son of now-deceased Talia Hale, Peter’s sister. Although that technically made Scott and Derek cousins, their rivalry was unmistakably that of siblings.
It went like this: a year after Melissa and Peter had gotten serious, and Peter had moved in, the Hale Estate had burned down. It was one of the most deadly incidents in the town’s history. Sixteen people, including four children under the age of ten, died that night. Once the smoke had cleared, Derek, Peter, and his older sister Laura, who was across the country attending NYU, were the only remaining members of the Hale family. Everyone and everything else crumbled to ash that night.
Melissa and Peter agreed to take in Derek until he finished high school, so while Scott and Derek weren’t blood-related, they were raised briefly together, in the same house. Stiles, who lived right next door, barely remembered the summer the teen first came to stay with the Hale-McCall’s. It was the summer Stiles’ mom died. He was eleven.
What Stiles did remember of Derek— a drawn, pimple-specked face. Stacks and stacks of books, novels, textbooks, spines worn, piled high. Glimpses of a meticulously clean room and blue walls, right before Derek’s bedroom door closed. Sad eyes.
Derek didn’t waste his time with two nosy pre-pubescent boys. All of his free time was put towards studying. Two years later, he graduated valedictorian.
He was kind of a big deal in their ten stoplight town, actually. Not only had he won some fancy national writing award for a personal essay about the fire, but as captain of the Beacon Hills lacrosse team, he’d led their school to the state finals for the first time since the 80’s. Once he’d graduated, he received a full ride to NYU and moved up north to be closer to his sister.
Derek Hale, success story. From town bad boy Stiles’ dad had given multiple warnings, to voted Most Likely to Succeed— Everyone loved a redemption arc. He even got interviewed for the Beacon Daily his senior year, for god's sake.
He was also Melissa and Peter’s favorite thing to talk about. Did you see Derek’s article in the Post? I wonder when he’ll finish his book and Do you think he’ll bring a girl home this Christmas? and Why don’t you ask Derek to help you study, Scott? I know you’re having a hard time.
Naturally, Scott couldn’t stand him.
“I just don’t understand why he’s coming here,” Scott bitched, not for the first time that day. “Wouldn’t it be more impressive if he completed his Master’s at his stupid New York school?”
They were cruising around town in the Jeep, looking for part time jobs. With class starting in two weeks, Stiles was already nervous about his course load and managing his time… But he needed a job. They had to start saving money now if there was any chance of moving out together next year.
“Maybe being impressive isn’t his goal,” Stiles countered, forever the devil’s advocate.
“Yeah, right. Like being impressive isn’t always his goal.” Scott scrolled through a list of job openings on his phone. “You should have heard my parents on the phone this morning, fawning all over him. Like he was the freaking second-coming of Christ. The guy’s totally obsessed with himself.”
“You know, Scott, some people are just naturally good at everything. Doesn’t mean he’s got some hidden agenda.”
“Hey, who’s side are you on?” Scott accused.
“Yours!” Stiles exclaimed, hands drumming at the wheel. “Yours, bro. Definitely. Just saying, second-coming or not, God has favorites. Some people are just like that.”
“You haven’t seen him lately.” Scott looked up, his mouth a grimace. “Nobody’s that perfect.”
Now that piqued Stiles' interest. “What, did he get hot or something?”
Scott scowled so deep he created a new wrinkle above his eyebrow. “Dude, I’m straight. How would I know?”
“Oh, so he’s hot-hot, huh?” Stiles was thrilled.
“Hot-hot? Really?”
“You know. Extra spicy.”
“You’re ridiculous.”
“Are we talking Fire! or Diablo levels of hot?”
Scott winced. “Can you not? He’s basically my brother.”
“Diablo, then.” Stiles grinned, trying to picture teen Derek from his memories as anything but gangly and socially inept. He couldn’t.
“Is sex the only thing you can think about?”
“Scott, I’m an eighteen year old virgin.” Scott looked at him blankly, so he finished, “…Of course it is.”
Scott glanced down at his phone again. “The vet up the street is hiring. We should go in and see if they have two open positions.”
“Smooth transition, man. Real smooth.” He turned toward the downtown square of Beacon Hills. “We’ll go there next. I need some caffeine first.”
“Can you just focus? For once?”
“Hey, coffee is a human right, okay? You’re the one who keeps blubbering on about your hot-hot brother-cousin.”
“Brother-cous—“ Scott rubbed his head, as if suffering from a sudden migraine. “You know what, whatever. You can see for yourself next Saturday. Mom said I could invite you and Allison over for dinner.”
“Sick.” Stiles parked the car. He paused, squinting at a sign in the window of his favorite coffee shop. “Is that a ‘help wanted’ sign?”
—
They don’t end up working the same job, in the end. Stiles got hired part time as a barista at Grounded, and Scott actually did end up working as a vet assistant, despite having literally no animal or work experience whatsoever.
Not like Stiles was jealous or anything. And anyway, being a barista paid more.
It was also a lot more work than Stiles had anticipated. The first three days had been long and grueling. On top of memorizing the entire coffee list, the shop served a full food menu in the afternoon and evening, and the staff was supposed to be cross-trained in every position due to being severely understaffed. Each day, Stiles left with dried syrup and other unidentifiable substances caked to his jeans and apron, his fingers smudged with ink from his leaking pen. And his feet— his feet ached so horribly he started propping them up on the wall as soon as he got home.
It was only natural that he decided to reward himself for his hard work. Never mind that he hadn’t been paid yet— Stiles went ahead and preemptively made a special purchase. He even made sure it would arrive on Friday, while Melissa was at work, just like he promised.
Stiles casually mentioned it upon picking Scott up from work that Thursday. The other teen sent him a look, smelling heavily of wet dog. “Well, I’m working until four tomorrow. You’ll have to grab it yourself.”
“I thought you were off? You promised I could use your PlayStation to finish off Shadow of the Colossus!”
“Dr. Deaton is going out to Bakersfield to induce a horse’s labor tomorrow morning. He said I could come.”
Stiles’ lip curled. “That’s disgusting, man.”
The dreamy expression on Scott’s face became much more serious. “Nature is beautiful, bro,” He said, affronted. “Don’t diss on the circle of life.”
“You haven’t kept a single plant alive for more than a week in your entire life, Scott.”
“Whatever. This is different.” Scott dismissed. “I’ve already decided I’m going to change my major to animal sciences.”
Stiles grinned. “No way, that means we’re going to be in the same department once you get accepted to University!”
“Really? I thought you were studying legends in history or whatever?”
Stiles rolled his eyes. “I’m minoring in Folklore and Legends; my major is Anthropology. Which is like, technically, a science.” He put an arm around the back of Scott’s seat as they turned into their neighborhood. “Look at us, just two STEM men, starting out. Look out, California!”
“God,” Scott cringed, smiling all the same. As they parked and he unbuckled his seatbelt, he added, “The house will be empty if you want to come in and finish your game tomorrow. I should be back before Peter gets home from work, anyway.”
“The best best friend. Seriously!” Stiles called after Scott as the other boy headed next door.
“Enjoy your panties!” Scott hollered back, without turning around.
Stiles froze, then whirled around, scanning the neighborhood to make sure no one heard. Ms. Ethel next door stared at him from across the street, watering her lawn.
“Candies,” Stiles explained loudly, unnecessarily. The last thing he needed was word of mouth getting back to his dad that his son was screaming about women’s underwear on their porch. “I got some candies from Japan arriving tomorrow. Delicious, you’re welcome to try some if you’d like!”
Ms. Ethel didn’t say anything— just wrinkled her old-lady face and turned back to her flowerbed.
—
Stiles liked pretty things.
He liked dainty jewelry, simple and delicate against pale skin. The frills of skirts against long legs, the intricate lace of a bralette. The gentle wash of pastel colors and fuzzy sweaters, the sharp contrast of thigh highs and crop tops. Skirts and booty shorts and panties—
Stiles liked them all. Specifically, he liked what he looked like wearing them.
It wasn’t really that deep, okay? Just a simple appreciation, and Stiles had always appreciated women— their clever words and soft powdery makeup and silky hair— but during high school, he’d realized the attraction that had so often accompanied that appreciation wasn’t for the women themselves. It was for the women’s clothes.
Stiles could still remember the first time he’d worn a skirt. It was thanks to Jackson Whittemore, of all people: freshman year, right before the first Lacrosse game of the season, Jackson had cornered Stiles and Scott in the locker room. Then he’d dared both of them two hundred buck to wear cheerleading costumes to the game, because it’s not like you losers will be playing anyway.
They’d all made it through try-outs— but just barely; Stiles being at least six inches shorter than everyone else on the team and Scott being asthmatic. Essentially, they were benchwarmers, at least for the season, and they knew it. It still hurt to have Jackson say as much out loud, though.
But again: two hundred bucks. Each.
Stiles didn’t need much more convincing than that— that was more money than he’d ever held in his hand at that point.
Scott, however, was a different story. They were crowded together in the back of the locker room, most of the team already gone, warming up before the game. Scott worried the fabric of the cheerleading uniform between his hands, putting it on all of two seconds before immediately stripping it off.
“Nope, fuck this. No way. We go out into the field like this, and we can kiss goodbye to any chance of getting girlfriends this year. Or ever.”
Stiles fiddled with the hem of his cropped shirt, hesitating. The skirt was right beneath it, high on his hips and dipping into a sharp V in the middle, showing off a couple inches of pale, pink skin and extenuating the curve of his hips. He turned around in the mirror to admire how the pleated fabric framed his ass, the shorts underneath pulled up high enough that the small crease where the back of his thigh met the fat of his backside peaked out. His legs were smooth and seemingly endless.
Stiles had shaved. For the bit, of course. Why else? What could he say, he liked to commit.
“Right,” he had agreed distractedly, still looking at his own ass. “Girlfriends.”
Eventually, he’d taken it off and they’d both gotten dressed as usual, deciding not to go through with the dare. As soon as Scott turned his back, Stiles shoved the uniform deep into his locker, under a bunch of other clothes, to grab later.
Things… escalated from there. Stiles quickly discovered his love for the feeling of fabric brushing against his thighs. For the feeling of skirts and shorts, for fuzzy, high, and soft socks, for fishnets and tights. For camis and belly shirts and eventually, frilly, lacey panties.
And then he started jerking off while he was dressed up, and there was really no going back after that.
Okay, so yeah, it was a little out there, but as far as the threshold for weird sexual fetishes went, it wasn’t that far from the realm of normality. Really, it was rather simple. Not weird at all.
He repeated that thought to himself all day Friday, a mantra to walk to as he paced around downstairs, waiting for the notification that his package had been delivered. When his phone dinged, he jumped off the couch and bolted for the door so fast he nearly sprained his ankle, spitting curses until his father, still trying to sleep, hollered down to him to watch his mouth.
There, sitting pretty on the Hale-McCall porch, was a black cardboard box waiting for him. Just as Scott had promised, there were no cars in the driveway.
Stiles scooped up the package and let himself into the Hale-McCall house, called out to see if anyone was there. Empty. It wasn’t really necessary for Stiles to sneak around— Melissa had given him a key back in middle school— but it was still a little awkward to be there without Scott. He went straight to his friend's room and powered up the PlayStation.
He played for about three hours before he reached a level he couldn’t seem to get past, the titan he was battling just kept ripping him a new asshole every time he tried. After dying for the millionth time, he threw down the remote and sighed. Left the room to get some water. Came back.
Considered looking up cheats. Decided against it. Sighed again.
The black box caught the corner of his eye.
Maybe he should…
What was he thinking? Of course he shouldn’t open it here. This wasn’t even in his house—
Which also meant his dad couldn’t accidentally walk in on him. Plus, it wasn’t like anyone would be home for a couple more hours…
Surely it couldn’t hurt just to take a little peak.
His hands were moving before he’d even consciously made a decision, tearing open the box. The inside was full of pink, satin-soft tissue paper. Stiles moved it aside to reveal what he’d bought.
Right there in the center of the paper, there was a pair of white panties. The fabric was soft against his fingers when he picked them up, tracing along to waist band. A little black bow sat at the top. Beneath the underwear, a garter belt and a pair of semi-sheer thigh high stockings were folded neatly.
It was his first time buying from this seller, so Stiles had only bought one pair of underwear, and had made sure to size up. He knew there were sites out there that made much more comfortable panties, specifically for men… but Stiles wasn’t a huge fan of those. They just weren’t as pretty.
Maybe Scott was right— maybe he was some kind of cross-dressing panty addict. Each time he shopped, he picked more and more extravagant and feminine things than the last time— a mirage of lilac and white and black, of pretty pinks and lace— to get that same high as the first time. To reach that unbalanced mountain peak that left him teetering between pleasure and humiliation…
He didn’t just like it. He craved it.
And really, what was the harm of just trying it on? To see if it fit? Scott’s bathroom was just down the hall— he’d go in there, lock the door, try it on, and take it right back off. That was all.
It was hours until anyone would be home. It was a completely fine, completely normal, totally rational, not insane thing to do.
He had barely entered the bathroom before he was shucking off his pants and boxers, overeager, hungry for it, for silk and softness. The panties went on first, mostly fitting, his balls snug and comfortable but the head of his dick catching a little on the waistband. He sat against the tub to slide the stockings up his smooth legs, one by one, snapping the band about mid thigh. They were a little tight, the fat of his thigh poking out around the top.
It took him a little longer than he’d like to admit to figure out how to operate the garter belt, but once he’d hooked each end of the weird hanging cords of fabric to the front and back of his stockings, he stood. Took a step back.
His reflection stared back at him: his skin shaved and delicate, unblemished except for the occasional mole; the bumpbumpbump of his spine curving inward; the blush spreading all the way down his face to the top of his neck. The garter belt definitely added something new to the look. It was black, fabric thick and cinched like a corset, giving his waist an hourglass shape, the straps made his legs look even longer, curving over the fat of his ass in a way that was nearly obscene. The white panties, a startling display of innocence next to the belt, sat perfectly against his pale skin, the fabric so soft it was all Stiles could do not to grind against the bathroom sink. He looked, undeniable, girlishly, eye-catchingly,
Pretty.
Aaand— yep. He was hard now. Great.
But before he could debate the merits of jerking off in his childhood best friend’s bathroom, the door swung open, and Stiles spun around, heart skipping a beat—
A large man trudged in, shirtless and sweating profusely, phone strapped to his arms and earbuds in. He sighed, scrubbed a hand down his face, and opened his eyes—
To belatedly notice Stiles already in the bathroom, frozen next to the sink.
In nothing but his underwear.
Women’s underwear.
Stiles let out something similar to a shriek.
“Oh,” the man said, almost casually, his voice so deep it sounded caught between a sigh and a growl. He wasn’t looking at Stiles' face. “You— I didn’t know this room was occupied. Sorry.”
Stiles’ eyes nearly bugged out of his head. He didn’t recognize him immediately, but he sure as hell recognized that voice. Before, it had seemed awkward— that low-pitched voice on a gangly, acne riddled teenager— but now, paired with the sharp jawline of a grown man and the sudden excess of corded muscle, it suited him perfectly.
“Derek?” Stiles gasped just as Derek was leaving, forgetting to be embarrassed in his shock.
Derek paused, eyebrows raised. He took out an ear bud. “Do I know you?”
Right. Of course he didn’t remember Stiles. Stiles was thirteen when he graduated. Not to mention, fully dressed.
“Um,” the younger man said, suddenly reminded of his lack of clothes. He turned away from Derek, facing the wall in an attempt to regain some privacy. To the wall, he said, “No. Definitely not, I— I’m just, uh, a friend of Scott’s.”
“Huh,” Derek said, and Stiles could see his reflection in his peripheral vision, a mirror image of the older man’s eyes sliding over the back of Stiles in a distinct once-over. Quietly— almost suggestively— he added, “Really? Scott?”
Stiles felt his face go up in flames. “W-what—”
“I’m going to use the bathroom down the hall,” Derek interrupted. “Sorry again.”
He closed the door.
—
Stiles stayed there for about ten minutes, completely petrified. Eventually, he forced himself to move. He pulled on his jeans right over the lingerie, bundling his shoes and his bag and the empty box all into his shaking arms, scanned the empty hallway and took off down the stairs.
Naturally, Derek was downstairs, chugging from a carton of milk in the kitchen, the fridge open, the light catching on his shower-damp hair, his dewy skin.
Stiles tried not to openly gape. He wasn’t sure he managed, judging by the way the older man choked when their eyes caught, but jesus, the guy practically oozed sex appeal. At least he was wearing a shirt this time.
Derek wiped at his mouth with the back of his hand and closed the fridge, staring right back.
A beat. Then two. Then three.
Stiles would just like to point out: he embarrassed himself a lot. In fact, usually, his ability to recover from accidentally humiliating himself was quite remarkable.
This—
This was different. This embarrassment had an unidentifiable edge to it, the air fraught with tension.
“You changed,” Derek spoke, breaking the silence.
Stiles squeezed his stuff to his chest so tight his arms hurt. “Um, yeah— I can’t exactly go out like that, can I?”
Derek looked down, eyes darkening. “No, not that.” He didn’t so much move closer as he did readjust, pressing a hip against the counter. His giant body faced Stiles, essentially blocking the path to the living room and out the front door. “You're Sheriff Stiliniski’s kid, right? I remember you.”
Great. Just— great. Stiles' shoulders dropped. He knew Derek was going to figure it out eventually, considering Stiles and Scott were always together, he’d just thought he’d have a little more time.
Reluctantly, he mumbled, “It’s Stiles.”
“Stiles. That’s right.” Derek said in that same perpetual rumble, and then— he did this awful thing where his mouth curled up on one side, in an uneven smirk, and—
Stiles had to get out of there. Now.
“I— I better g-go, it was nice seeing you…” Stiles trailed off, inching closer, hoping the older would move out of the way.
He didn’t. “Like that?”
“E-excuse me?”
“Aren’t you going to put on your shoes? You’ll tear up your tights.” Derek nodded to the ground. Belatedly, Stiles realized he’d been staring at his feet during their conversation— poking out below his jeans, still wrapped in the damning semi-sheer fabric of his stockings.
Face hot, toes curling against the wooden floor in an effort to shy away from the sharp gaze, he stammered, “Oh, it’s fine, I still live just next door—“
“What, do you need help putting them on?” Derek asked— demanded, more like. For some reason, he seemed even bigger in the moment, his presence occupying all the space in the kitchen—
The mental image of this giant man on his knees, putting his shoes on for him was way, way too much—
“N-no. No, I can— I’ll do it myself—“ Stiles said breathlessly, a little dazed. He set his stuff down on the kitchen counter next to Derek, bending over slightly to put on one shoe at a time. His shirt jostled upward for a moment, the sharp line of the garter belt flashing alongside his stomach.
He didn’t miss the way Derek’s eyes flickered back up to his face when he straightened up.
“Good,” Derek drawled, moving his body to let Stiles pass. “See? That wasn’t so hard, was it?”
Stiles gathered his stuff back into his arms, fully trembling now. “It was nice—“ seeing you again, he started to repeat, but Derek was already strolling down the hallway, his back to Stiles.
—
Later that night, when Stiles was alone in his bedroom with one hand down his pants and the other shoving fingers into his mouth, he spilled all over himself, staining his brand new panties— the thought of someone on top of him, pinning him down, a deep voice against Stiles’ ear, Open your mouth a little wider for me… See? Good boy, was so intense he nearly cried when he came.
—