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English
Series:
Part 1 of Sterek Sexytimes
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Published:
2025-02-05
Completed:
2025-02-19
Words:
9,565
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2/2
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7
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72
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The Six Times Before

Summary:

A prequel to Around You Inside You with the first six times Derek and Stiles had sex. Basically pwp with characterizations.

Notes:

(See the end of the work for notes.)

Chapter Text

Derek stared at Stiles. He still couldn’t bring himself to reach out. He refused to be like Kate: a groomer, a user, a manipulator.

“I’m 18 now, Derek,” Stiles said. “I know you’ve got this thing about me being younger than you, but, it’s, it’s legal—I’m legally an adult now, and I get how you might still feel weird but…look, I know there’s something—something between us. There always has been. You’ve treated me different from the others, and not just ’cause I’m human.” He looked at Derek with those soft doe eyes, and there wasn’t anything Derek wanted more than to wrap Stiles up in in his arms and hold him.

“Stiles, I—“ But the words wouldn’t come. Derek shook his head and huffed, unable to force himself to push Stiles away or draw him near. He felt paralyzed.

Stiles suddenly licked his lips and moved in closer. Derek could see how Stiles’ eyes darted to his own lips, then back to his eyes. Grabbing both Derek’s limp hands, Stiles brought them up to his face. The moment Derek’s palms felt the warmth of Stiles’ cheeks he held on, and when Stiles finally leaned in, putting his own hands on Derek’s hips, Derek thought he might faint.

“Stiles—“ The name slipped from Derek’s mouth, and Stiles gave a nervous sort of smile then kissed him.

Shocked to a standstill again, Derek let Stiles do the kissing until he started to pull away with a hurt moue then Derek surged forward and attacked, kissing Stiles hard and desperate.

Stiles’ tongue tentatively licked against Derek’s lips and Derek groaned and opened willingly. Kissing Stiles, tasting Stiles, after all that time… Derek was enraptured.

They stood close and kissed and kissed, time standing still, until Stiles’ phone went off, vibrating in his front pocket. Stiles jerked away, snatching it out to stop the incessant notification. Derek watched and saw that Stiles was hard and the phone’s vibration must have been too much sensation so close.

It made Derek smile. He still had one hand on Stiles’ face, but he dropped his forehead onto Stiles’ shoulder.

“Oh shit that’s like the worst timing ever! I’ve gotta go. I have an appointment with my psychiatrist. It’s just a med check but if I don’t go she won’t refill my Adderall and some people grow out of needing it so she’s checking closely and—“

Derek looked up at Stiles, still smiling. Stiles’ face was flushed adorably and his eyes were wide.

“Shh,” Derek murmured. He kissed Stiles softly. “Go.” He dropped his hands to his sides.

Stiles stared at Derek for a long moment. “You’re smiling.”

Derek nodded.

“Wow, that’s—I mean, I’ve seen you smile before but not, like, not at me and not so close and I really wanna stay and kiss you some more.”

Derek nodded again.

Stiles stared at him for a long moment, then touched Derek’s cheek, sliding his fingertips through Derek’s stubble.

“I’ll, um, I’ll call you after?”

“Yeah.”

“Okay.”

“Mm-hmm.”

“I gotta—“ Stiles jerked his thumb toward the door and half stumbled as he turned his feet to follow the gesture while keeping his torso facing Derek.

Go,  Stiles. It’s fine.”

Stiles went to the door and looked over his shoulder one more time.

Derek laughed and Stiles grinned and finally left.

 

Stiles floated through the meeting with his shrink. They agreed to keep him on his current dose of Adderall since he was still in school. The doctor suggested that after graduation they could experiment with a reduced dose. Stiles nodded and agreed and tried to hurry everything along. He wanted, very badly, to get back to thinking about Derek and their kiss and what it might mean and what else they might do.

Driving home, Stiles forgot that his dad was going to be at work that evening. He looked in the fridge and decided on scrambled eggs and toast. Drinking distractedly from the orange juice jug while he cooked his eggs, Stiles burned the toast when he started thinking about kissing Derek.

The eggs were overcooked and rubbery but the second round of toast came out okay. After washing up the dishes, Stiles got his phone out of his pocket. He paced back and forth in the small kitchen, thumbing at the side of the device.

He said he’d call. So he should call, right? Or maybe he should call Scott and tell him what happened and see what he thought. But Scott was seeing Kira now. And he’d been with Allison before that. Stiles only had one heavy petting situation with Malia, and he’d been possessed at the time so did that even count? The time Lydia kissed him to stop his panic attack definitely didn’t count. He barely remembered it. Scott would probably tell him to just go for it.

But it was Derek . Would Scott approve or would he think it was weird? Scott knew Stiles was into guys too but he’d never acted on it before and maybe it was weird just because Derek was older, and a former alpha, and he and Scott had always butted heads. Maybe it wasn’t weird because it was a guy but because it was a werewolf, but why would Scott think sex with a werewolf was weird when Scott himself was a werewolf?

Stiles wondered if he should call Danny. Maybe Danny would have insight. But they weren’t really friends, just former teammates and really, just because Danny was gay didn’t mean he was some kind of queer guru. Plus Danny was away at college now, and it would be totally weird to just call him out of the blue, wouldn’t it?

But he was supposed to call Derek. Was it getting too late to call? Was it past some unknown allotment of time, had he missed his window of opportunity? Maybe Derek thought he wasn’t interested anymore because he’d eaten first? Oh shit, had he ruined it before it really even started?

Knock knock knock

Stiles jumped so hard his phone flew out of his hands and he juggled it, finally getting a firm hold and stuffing it in his pocket. His mind raced as to who the hell was at his door after dark but-c’mon-they all ended up at each others’ houses at all times of night and day so what was he even—

He opened the door.

Derek.

It was Derek.

 

“You said you’d call, but I didn’t want to wait,” Derek said. He hunched his shoulders a little, feeling self-conscious.

Stiles’ face lit up and Derek relaxed minutely.

“Your dad’s not here, is he?”

“No—no, he’s working til nine,” Stiles said, and looked at his watch. “We have two hours, so why don’t you get in here?” He opened the door further and stepped back.

Derek shrugged and entered. He sighed with relief that he wouldn’t have to face the Sheriff so soon after he began—whatever this was—with Stiles.

“Did you have dinner? I made eggs—we’ve got more I could make you some, or something else? We always have sandwich stuff—you want a sandwich? I—“

Derek pulled off his jacket and hung it by the door, and Stiles stopped speaking for a moment.

“You changed. You’re wearing a nicer shirt, Derek, what—why? I mean, not that I mind it, you look great and that gray makes your eyes—I, uh, your eyes are always awesome, but that…that shirt…what are you doing?”

The chatter went through Derek like a wind. A warm, summer wind that made him think of family and home, and before the fire. Derek was drawn to Stiles and reached out to hug him. Stiles didn’t respond at first.

“This okay?” Derek asked, speaking low into Stiles’ ear then taking a deep breath of Stiles’ scent.

“Oh, um, yeah, just a little—are we friends now? Friends who—hug, and who kiss or are we like more and—“

Derek started to feel foolish. If he couldn’t smell the arousal wafting from Stiles, he might have withdrawn and maybe even run away. He started to let go anyway, then Stiles grabbed him, pulling their chests tight together, his hands smoothing up and down Derek’s back.

“Stiles…” Derek sighed. “We’ve been friends a long time. Aren’t we—after earlier, aren’t we— more ?”

Stiles huffed, then laughed a little. “Yeah, I guess so. I hope so, anyway.”

Derek drew back and gave Stiles a lingering, soft kiss.

“Me too.”

Stiles tightened his grip on Derek and leaned in for another kiss. Derek’s heart felt ready to take flight. Being allowed to kiss Stiles, finally .

There was a hint of butter on Stiles’ lips, but soon it was just the taste of Stiles, the feel of his lips and tongue and Derek got lost in it.

Stiles’ hands ran up and down Derek’s back, and Derek wrapped his arms around him. Having Stiles so close, feeling the warmth of him, was like heaven.

Stiles shuffled closer and Derek could feel Stiles’ hardness against his hip and it made him groan. His own jeans were getting uncomfortable with the need to adjust. Stiles pressed forward again and groaned in reply.

“Derek—I could, I could come just like this,” Stiles said, gasping.

“Mm, maybe, but I’d rather touch you more first.”

Stiles dropped his head back, exposing his neck, and sighed. Derek forgot instantly that he’d had plans and started nipping and kissing Stiles’ throat.

“Oh shit, if that’s, we gotta, oh Der—“ Stiles tilted his head and Derek growled as he sucked on Stiles’ pulse point, making Stiles swallow hard. “Bed. My bed, C’mon,” Stiles said, his breath coming fast. He started to pull away and Derek growled in earnest and wrapped his arms more firmly around Stiles, who laughed. “Derek. Derek!”

Derek withdrew, dizzy with the scent of Stiles and the feel of his skin. He admired the red mark he’d left, but Stiles ducked his chin and hid it, apparently trying to catch Derek’s eye.

Derek looked into Stiles’ face, taking in the red splotches of blush on his cheeks and the irrirated skin around his lips and tried to lean in for more kissing. Stiles stopped him, putting a hand on his chest and pushing away firmly. Derek frowned and finally met Stiles’ eyes.

“Upstairs. My room. My bed,” Stiles said, and Derek’s reverie broke and he finally understood.

Derek grabbed Stiles’ wrist and headed for the stairs, taking them two at a time, finding himself grinning as Stiles laughed.

 

Seeing Derek get so wholly focused on making out that he lost himself was a heady thing. Derek, Derek wanted him? That badly? Whoa.

After basically dragging Stiles upstairs and into his bedroom, Derek suddenly shifted from determined to hesitant.

“I—I’m sorry, Stiles, I don’t want to push you into anything—“

“What the hell are you talking about? Get over here!” Stiles exclaimed, diving over onto his bed and holding his arms out.

Derek gave a little smile and stripped his shirt off quickly. Stiles almost swallowed his tongue when the realization hit him that all that skin, all those muscles, they were all fair game now to lick and touch and—

Derek crawled on top of him and started kissing Stiles. Stiles wanted to both melt into the bed and wrap himself up in Derek forever.

Derek did a body roll, legs-hips-stomach-chest, and Stiles yelped at the sensation.

“Oh yeah, do that again,” he said against Derek’s mouth, and then threw his head back into his pillow when Derek obeyed and their hips pressed tight together again. Stiles wrapped his arms around Derek, sliding his fingers over skin and muscle and then dropping his hands down to Derek’s ass and pulling them together again. And again. And again.

“God—I’m seriously gonna come,” Stiles gasped.

Derek immediately released pressure on his hips and backed off.

“Not yet. Wanna feel you,” Derek said in a low voice. Stiles shivered, but sat up and pulled his shirt off. Then Derek’s hands were fumbling at Stiles’ pants and Stiles could barely breathe, watching Derek’s blunt fingers unfasten and unzip him. Derek’s hands shifted to Stiles’ hips and pulled down on pants and underwear both, then one wrapped around Stiles’ cock.

Ngh! Fuck! Why—why’s that feel so different with someone else doing it?” Stiles marveled. Derek laughed darkly and started stroking, thumbing over the wet head and spreading precome down to ease the way. Stiles’ eyes rolled back in his head for a moment and he moaned loudly. “Derek-Der— I—I’m gonna come, like for real this time, gotta—“

Dererk kissed him roughly and sped his hand. “Do it, Stiles. Come all over yourself. Come all over me—“

Stiles did. The thought of coming on Derek was followed by the action, and he strained to keep his eyes open to watch Derek looking at the head of Stiles’ cock as it spurted. Derek’s mouth was open and he stared enraptured as the come hit Derek’s own belly and then trailed onto Stiles’, finishing up dribbling down the side of Derek’s hand over his knuckles.

Hottest. Thing. Ever.

Then when Derek gently released him and raised his knuckles to give them a tentative lick, Stiles felt an aftershock wave of orgasm and another few drops dripped from his cock.

Stiles needed a whole new measuring system for what was hot.

 

Derek felt a little shy as he rolled the taste of Stiles’ come around his tongue and decided it wasn’t the worst thing ever. He looked up at Stiles and smiled, then kissed him softly.

“You’re so gorgeous, Stiles. I could just stare at you forever,” Derek found himself pouring out his heart and every little thing he adored about Stiles. “You’re so brave, and you’re funny and loyal, and I trust you completely, you know that? Somehow I’ve always trusted you and you never let me down. You’re amazing, and—“

“Oh my god, Derek Hale, getting sentimental and waxing poetic after sex, and he didn’t even come!” Stiles overroad him and Derek felt himself blush. He was still hard but it wasn’t critical to address it at the moment.

Derek pushed himself up with his clean hand and reached toward the nightstand for tissues. He wiped his hand, then hesitantly cleaned off Stiles’ pale belly, and then his own. He threw the tissues away and found himself drawn to stare at Stiles even as he settled beside him.

Stiles had one hand still half buried in his own hair, which stood up every which way from pulling on it. Why hadn’t Derek seen him do that? Oh yeah, because he’d been watching Stiles’ cock. Derek smiled ruefully. He hadn’t even gotten to see Stiles’ O face.

Leaning over, Derek kissed Stiles again. Stiles smiled into it and gave a happy sounding sigh.

“You okay? You want me to reciprocate?” Stiles asked. Derek shook his head.

“Just wanna look at you,” Derek said. “Wanna touch you,” he added, then followed word with deed. He cupped Stiles’ face, thumb running across his cheek and then down his throat to his shoulders and arms then he trailed his fingers all over Stiles’ chest, scraping his nails through the little hairs around his nipples and in the center of his chest. He palmed Stiles’ hip bone and scratched through his pubic hair and happy trail. With the refractory period of a teenager, his cock was already plumping up and Derek grinned at Stiles, who blushed but grew harder.

Helping Stiles the rest of the way out of his pants and boxer briefs, Derek wasn’t surprised when Stiles reached for the button of Derek’s jeans. Together they got Derek naked as well and they laid down side by side on Stiles’ bed.

Stiles seemed fascinated but embarrassed by Derek’s hard cock and he kept glancing down and away, but eventually reached out. His touch was tentative at first, his fingertips exploring Derek’s foreskin before he grew more confident and wrapped his hand around the shaft, giving a few pulls. Derek’s hips bucked and Stiles looked back to Derek’s face, pleased by the response.

Derek leaned in and kissed him again, and they stayed like that, kissing, with Stiles trying different holds and speeds. Derek shivered and gasped at being played with, and with a glance down between kisses, he saw Stiles was fully hard again. He pulled Stiles over onto his side and rolled to face him, then drew their erections together with his hand and Stiles’ wrapped around them together.

“Oh shit! God, Derek, that’s so hot!” Stiles groaned. Derek nodded in agreement and they worked to find a pace with their hands and their thrusts with the heads of their cocks bumping against each other.

“Lube. Do you have lube?” Derek asked, briefly breaking away from their kissing.

Stiles nodded and reached blindly for the nightstand, grabbing a bottle that he flicked open and squirted all over their hands and cocks.

They both moaned as the slide eased and became fluid. Stiles’ hips soon began stuttering and Derek broke their kiss to watch Stiles come, his mouth open, a loud cry of Derek’s name bursting from him. It was beautiful, and Derek humped forward hard several more times then closed his eyes as he came as well, adding to the mess between their stomachs and breathing hard.

“That was amazing,” Stiles said. Derek grunted in agreement. “But what a fucking mess!” Stiles tried to scoop some of the come and lube dripping down toward the bed up with his hands and rolled away.

“Umm,” Derek chuckled, looking around. It was a lost cause. The comforter they’d laid on top of was liberally splattered with wetness. Stiles glanced back and sighed. He wiped his hands on the fabric and grabbed a corner to swipe at his belly.

“I’ll be right back,” Stiles said.

He returned quickly with a wet washcloth that he offered to Derek. Derek wiped his hand, stomach, and cock off before he carefully got up to stand beside Stiles. Dropping the washcloth on the comforter, Derek turned and wrapped his arms around Stiles.

“Sorry about the laundry,” Derek said. Stiles laughed.

“Worth it.”

They held onto each other for a long moment. Derek glanced at the clock on the nightstand over Stiles’ shoulder and groaned.

“Your dad’s gonna be home soon and as much as I want to stay and spend some afterglow with you, I should get out of here unless we want to have a very blunt talk with the Sheriff.”

“Yeah, no, I definitely don’t think I’m ready to tell my dad that we’re—“ Stiles paused. “Um, whatever this is. Dating? Sleeping together?”

“Together, anyway.”

“Together. Sure,” Stiles smiles, a little shyly, and Derek grinned at how adorable he was.

“You want help with the laundry?” Derek asked.

Stiles looked over at his clock and jumped. “No! You’ve gotta leave, dude!”

Derek sighed, gave Stiles a final squeeze, then reached for his clothes.

A scant few minutes later the comforter was in the washer with the very filthy washcloth and Derek was by the front door. Stiles was dawdling, apparently not wanting to say goodbye.

“Can I see you tomorrow?” Derek asked. He wrapped Stiles tight in his arms again, their heads coming to rest comfortably on each other’s shoulders.

“It’s the weekend, yeah! Dad’ll be at work all day. Can I make you breakfast?”

Derek smiled. “How about you let me know when he’s left and we can decide?”

They kissed and Stiles’ hand in Derek’s held on until Derek was out the door and he finally let go.

When Derek got to his car he turned back, and they shared a long look before he got in and drove away.