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Stiles slides the silky fabric up his thighs. His hands are shaking, and it takes him a minute to fumble the waistband around until it’s smooth against his hipbones. The panties are a pretty, pale blue with lacy white trim on the waistband and around the leg holes. There’s even a white bow in the front, right in the center, the loops tacked in place so the ribbon will always stay right where it’s supposed to. Stiles’ hands are still shaking as he reaches inside and adjusts himself so his dick is tucked back and held in place by the flimsy underwear. He’s not really sure how something so scanty and airy is managing to keep him in place. Maybe it’s the cut of the underwear, Stiles muses, trying to distract himself a little from the fact that he’s wearing panties.
Eventually, though, he can’t keep his mind off it any longer, and he lets himself look. In the front, everything is smoothed down and tucked in place. He’d shaved his crotch bare earlier, to help with the illusion, and it had seemed odd to have a hairless dick but hairy legs, so he’d shaved those too, and then his chest, and his underarms. From the front he looks good. He turns around slowly, and adjusts the fabric over his ass a little. He looks—he looks slutty from behind. The panties don’t cover his cleft all the way, but now that he’s got them on he can see that they’re not designed to. The blue silk dips low on purpose, exposing the top of his cleft, and the lace separates from the silk, framing the area with little frills. Stiles sucks in a breath and shuts his eyes. His heart is beating heavy and thick in his throat, and he wants—he wants.
Forcing himself to breathe normally, Stiles picks up the lip gloss and mascara he’d been hiding for months. He’s experimented with the mascara before, so it’s not as awkward as it could be to unscrew the wand and coat his lashes with it until they’re covered. He blinks a few times, examining his results. His eyelashes look fake, too long and too dark to be natural, and he almost wishes he had some liner to run along his upper lids, but he doesn’t. Instead he sets aside the mascara and opens the lip gloss.
The gloss is thick and dark red, and after Stiles has smeared it carefully over his mouth he shivers. His mouth looks curvy and feminine and plump. Stiles shivers again. There’s something about the slick, shiny red that makes him feel tingly and electrified.
There’s a soft thump from behind him and Stiles turns around in shock. Derek’s standing in front of his window with a look on his face that Stiles can’t quite read.
“What are you doing, Stiles?” Derek asks.
“I—there’s nothing wrong with what I—I mean who gave you the right to just come in here and—“ Stiles starts, but Derek cuts him off.
“You shouldn’t have sent me that text, Stiles.”
“I—I didn’t,” Stiles protests, even though he did. He’s been planning this night for months, and last week, he’d clued Derek in as to what he might want to explore, sexually speaking. Derek had been amenable at the time. When he’d finally gotten everything together for this little experiment, he’d texted Derek, and let him know that if he wanted to see, he should come over in the evening. He’d hoped, but he’d never dared count on Derek actually going through with it.
“You did, though,” Derek growls. “And if you don’t stay still and keep quiet I—“
“You’ll what?” Stiles challenges, feeling defensive.
“I’ll have a very hard time not kissing you,” Derek grits out.
“Well I—what?” Stiles blinks. “Really? Because you—you could do that. If you wanted. I mean. There was a whole fantasy that was going to go along with the—“ he waves a vague hand at himself, “—all of this, and you were definitely going to fit in there at some point.”
“What kind of fantasy, exactly?” Derek asks. Stiles is, for once, lost for words. Derek isn’t though. “The one you talked about the other day? Or a different one? Maybe more explicit than just me watching you through the window, hm? Do you want me to fuck you? To smear that pretty red lipgloss all over your face? To suck your tongue and your nipples and tell you that this is all you’re good for? To be fucked and played with? Do you want me to pull down those pretty panties and spank you? Slide fingers up inside you and play with your hole until you come untouched?”
“I—yeah, that—that sounds good,” Stiles nods. “But like, I—I also want you to do stuff and like—I want to say no and stop and stuff?” Stiles tries.
“And you want me to keep going,” Derek guesses.
“Yeah,” Stiles nods.
“I could do that,” Derek says, reaching out. He catches Stiles’ wrist and Stiles has a moment to wonder when Derek got so close to him before Derek’s whispering in his ear, “You need me to really stop, you say monkshood, got it?”
“Monkshood,” Stiles confirms, and then he’s sprawled across Derek’s lap, toes scrambling for purchase against the carpet. He gets enough leverage to prop himself up on his arms, his back curved into an arch, but Derek ignores him in favor of palming Stiles’ ass.
“Pretty,” he comments. “You pick these out yourself?”
“Yes,” Stiles admits. Derek gropes at Stiles’ ass and crotch, then pulls down the panties and gives Stiles’ bare ass a few quick spanks.
“This isn’t really what you need right now, is it?” Derek asks, hauling Stiles upright and settling him so he’s straddling Derek’s lap instead of sprawled on it. “What you need is someone to tongue fuck your mouth until it’s swollen and you’re gasping for air because they won’t stop when you need to breathe.”
“Derek, please,” Stiles gasps.
Derek tumbles them to the bed and seals his mouth over Stiles’. He tongues along Stiles’ teeth, then sucks hard on Stiles lips and tongue. Stiles can already feel himself running out of air, and he tries to breathe through his nose, but it’s harder than it should be with Derek’s weight on his chest and his mouth stopped up with Derek’s. Derek gets a hand around Stiles’ throat, too, squeezes just enough that Stiles whimpers underneath him, the threat of cutting off his air making him shake. Derek just keeps kissing, though, biting and sucking, and finally fucking his tongue into Stiles’ mouth. Stiles clings helplessly to Derek’s shoulders, unable to kiss back, unable to catch a breath, unable to do anything except let Derek fuck his mouth with his tongue. Stiles starts to feel dizzy, and he moans as he tries to suck in air. Derek chuckles into his mouth, and keeps up his assault just long enough to let Stiles know he’s not going to stop just because Stiles is uncomfortable. He does stop though, his mouth pulling away with a loud smacking noise.
“Oh god, Derek,” Stiles gasps, back arching as he tries to push closer to Derek. “Derek, I—please, I—“
Derek ignores him, opting instead to stand up and haul Stiles off the bed after him. He takes Stiles by the elbow and flings him across the room to the mirror. “Look at yourself,” he orders, holding Stiles in place and tipping his chin up so he’s forced to look at his reflection. “Look at the mess you’ve made. Lip gloss everywhere, and your mouth swollen and scraped raw from my beard. And in those panties, Stiles, do you know what you look like?”
“I—no,” Stiles blinks at his reflection, raising his free hand to touch the beard burn. He hadn’t noticed it before, but now that he sees it, now that he can touch it, it prickles around his mouth like the time he’d kissed a cactus during a game of truth or dare—only better and worse at the same time.
“Pay attention,” Derek snaps, shaking Stiles’ elbow. “You’re such an empty-headed little slut,” Derek sighs. “Always distracted and confused. I’ll have to do something about that, Stiles. I’ll have to find a way to make you pay attention.”
Stiles doesn’t answer, just looks at Derek, his mouth slightly parted.
“God, look at you,” Derek says, yanking Stiles back toward the bed. “Just begging for someone to put you down and use your pretty holes. Maybe then you’d be able to focus, if you had something plugging up your empty places, hmm?”
“Derek, what—“ Stiles protests. “I’m not—I’m not a ditz.”
“No?” Derek asks. “Did you answer my question, then? When I asked if you knew what you looked like?”
Stiles shakes his head.
“And were you daydreaming? When I came in the window, were you paying attention or were you fantasizing?”
“I—I was fantasizing,” Stiles admits.
“See? Unaware and dizzy,” Derek shrugs. “It’s all right, Stiles. Pretty sluts like you don’t need to be smart and attentive. You can get by on your looks alone.”
“But—but I thought—I got all A’s on my report card last semester,” Stiles points out.
Derek takes Stiles’ chin in his hand and tilts Stiles’ head up to kiss his mouth. “Oh, sweetheart,” he laughs, voice soft, “everyone knows exactly how you got those A’s.” He sucks Stiles’ weak protest right out of his mouth, biting Stiles’ lower lip again and tugging before stepping back and slapping Stiles’ ass. “All right, gorgeous. Get on the bed and show me what you’re good for.”
“Derek,” Stiles begs, his chest feeling tight, his heart beating too-fast, “Derek please, I don’t want to.”
Derek smiles indulgently and pushes Stiles toward the bed again. “Stiles, little sluts like you don’t get to say no.”
Stiles’ breath catches on a sob. He feels overwhelmed and stupid and empty-headed, can’t remember why he ever thought he was smart. But knows that’s wrong, and he can’t just give in, so he shakes his head again. “No, Derek. I don’t want to let you fuck me. I—you should go.”
Derek laughs again and shoves Stiles hard enough he trips and lands on the mattress. “Ass in the air, Stiles,” Derek orders.
Stiles whines as he obeys, feeling petulant and unwilling even as he spreads his legs and pushes his butt up for Derek.
“See? You can be so good when you just pay attention,” Derek praises. Stiles feels inexplicably pleased with the praise. “You’re such a good little slut. Since you tried to say no, though, I’ll have to spank you before I fuck you. I know you want me to just put it in you already, but you know the rules. Good sluts let their owners get them wet and loose. Good sluts don’t complain if their owners decide they need spankings.”
“O-owner?” Stiles gasps.
“Of course, silly,” Derek smiles, then brings his hand down on Stiles’ ass. “I’m your owner. You pretty, baby sluts need a firm hand to help you out, especially when you’re just starting out.”
“But—but what if I don’t want to be a slut?” Stiles asks.
Derek keeps spanking him as he answers. “Oh, but sweetheart, it’s so clear that you do want it,” he explains. He lands swat after swat on Stiles’ ass, and Stiles can’t help squirming under the assault. “It’s plain to see. The panties, the makeup, the way you look at me with those big, sweet eyes of yours, like you’re imagining what it would be like to suck my dick.”
“I—no, no I’m not, I didn’t—“
“Shh, it’s all right, Stiles,” Derek soothes, moving his spankings lower on Stiles’ butt, to the place where thighs meet hips. “I know how much you want it. I’ll even let you have it, since it clearly means so much to you. But not this time. Tonight I’m going to fuck your pretty slut hole. Maybe next time I’ll let you get your mouth on me. Would you like that?”
“No, Derek, I—I don’t want it,” Stiles pants. His skin feels tight and hot as Derek keeps hitting him. “Oh please, stop? Please, I—I can’t anymore, I can’t.”
“Shh, you can, baby, you can,” Derek encourages. “Shh. Just think about next time, all right? Think about going on your knees for me, opening up your pretty lips, your throat, letting me slide inside and fuck over your tongue, until your mouth is bruised and you can hardly catch enough air. Think about that, about me, thick and heavy in your throat. About how you’ll look up at me through those pretty lashes, all wet with tears, and you’ll be so grateful to me for letting you do this. I bet you’ll even shoot off your sweet little prick in your panties, before I even get close to coming.”
“Derek!” Stiles wails, fingers clutching the sheets.
“All right, sweet slut,” Derek croons, stopping his smacks and rubbing across Stiles’ abused skin. He leans over Stiles, his jeans scraping against Stiles’ tender ass, and rummages through Stiles’ night stand until he finds his lube. “Gonna fuck you bare tonight, babydoll,” Derek murmurs, like he’s gentling a nervous animal. “Gonna let you have all my come, and when I’m gone you’ll be able to feel it inside you, leaking down your thighs. You’ll like that, won’t you baby?”
Stiles just moans, and lets Derek stretch him open around three fingers, until Stiles is slick and wet between his legs, lube everywhere, his panties pulled down just enough to give Derek access to Stiles’ hole.
“Ready, sweetheart?” Derek asks, fitting the head of his cock inside Stiles’ asshole.
“All right,” Stiles agrees softly. He tries to brace himself for Derek fucking inside, but Derek is careful, sliding in slowly.
“There you go,” Derek murmurs. “There you go. All nice and full now, aren’t you? Feeling better, slut-bunny? Feel more like yourself now that you’ve got my dick all tucked up inside?”
“Oh, fuck,” Stiles’ breath hitches. “Fuck, Derek, please—please I want you to move.”
“All right, slut-baby, I’m here, I’ll give you what you need,” Derek promises. He starts fucking slowly, carefully, building up speed and force so that Stiles has time to adjust, time to brace himself.
Stiles’ mind goes shockingly blank as Derek fucks him. He feels strung-out and used and shocky, like he’ll never be the same again, and his brain shuts down and lets him drift as Derek fucks him thoroughly. At some point, Stiles must come, because by the time Derek finishes, he’s lying in a wet spot and his panties are gone.
He lets Derek move him around once Derek’s pulled out of his ass, his come already starting to leak down Stiles’ thighs, just like he promised. Stiles just goes where he’s put, blinks up at Derek as Derek wraps Stiles in a blanket and kisses his forehead. He’s not sure what Derek’s doing, exactly, but when Stiles starts coming back to himself he’s been cleaned up, his thighs and ass and stomach wiped down with a wet cloth, his face cleaned of makeup. He’s wearing soft pajama pants and what looks like Derek’s t-shirt, and Derek pets his hair and puts him to bed in clean sheets.
Derek tucks him into one side of the bed, then slides in behind him, wearing just his boxers. “Okay?”
Stiles nods. “Yeah,” he sighs. “I feel all soft and liquid.”
“I think you hit subspace,” Derek admits softly. “I’ve never seen anyone do that their first time. It was amazing.”
“Yeah?”
“Yeah,” Derek nods, then tucks his nose against Stiles’ neck. “It’s all right if I stay the night?”
“Yeah,” Stiles confirms. “Dad’s working a double.”
“Next time, maybe we should do this at my house instead of yours, since I don’t live with any relatives anymore,” Derek suggests.
“Mm. Okay. You really gonna fuck my mouth until I cry next time?” Stiles wonders.
“Maybe,” Derek shrugs a little. “If that’s what you want.”
“Right now I want cuddles,” Stiles huffs, pouting at Derek.
“I can do cuddles,” Derek smiles, and loops his arms around Stiles’ waist. “Now sleep. We’ll talk more in the morning.”
Stiles leans into Derek and lets himself settle into sleep.