Compromising Positions | Into the Black | Contact

First and Last and Always: More

Notes: So, while beta-ing First and Last and Always, the awesome emungere requested Stiles fucking Derek, and at the time, I just couldn't work it out. And then I wrote this for her birthday.

And proving that she's super-extra awesome, not only did she say it was okay for me to share it with everyone else, she beta-ed it.

Takes place at some point before Sheriff Stilinski finds out about Derek and Stiles.





It’s late, but Stiles isn’t in any rush to get home since his father is pulling a double tonight. They lie curled together on Derek’s bed, exchanging lazy kisses and teasing touches, the early days of frantic urgency far enough behind them that they can take their time exploring. Derek is lightly kissing the moles on his neck when Stiles blurts out, “Can I fuck you?”

Derek looks up at him, shrugs, and says, “Sure.”

Stiles’ jaw drops, and his eyes widen in surprise. He manages to make a slight squeaking sound.

Derek raises an eyebrow in question and says, “What?”

“Just, ‘sure’? It’s that easy?” Stiles asks incredulously.

“Why wouldn’t it be?” Derek replies, running his fingers down Stiles’ chest.

“Are you kidding me? I’ve been trying to find the balls to ask you for weeks! I was sure you were going to be all ‘I’m the Alpha, I don’t submit’,” Stiles replies, his voice lowering in a terrible imitation of Derek.

Derek makes a face. “Is that supposed to be me? Don’t ever do that again.” He kisses Stiles’ collarbone before continuing. “You do know I’m not actually a wolf, right, Stiles? I can control my instincts.”

“Tell that to the bite marks on my neck,” Stiles replies tartly.

“I can control my instincts when I want to,” Derek says in response, flashing Stiles a toothy grin.

“Fucker,” Stiles mutters in response, and Derek just smiles wider, and then leans in to give Stiles a soft kiss on the mouth, lingering briefly. When he pulls away, Stiles hangs on and reels Derek in for a longer, deeper kiss. When the kiss finally breaks, Stiles says in an offhand manner, attempting nonchalance, despite the fact that he knows his heartbeat is giving him away, “Can I fuck you now?”

“Sure.” Derek says in the same offhand way, with another shrug. Then he grins cheekily at Stiles and rolls them over until he’s straddling Stiles’ hips. “I wouldn’t mind going for a ride.”

Stiles is pretty sure he’s never gotten so hard so fast in his life. He just gapes disbelievingly at Derek. It’s like one of his fantasies coming true. It’s almost too much to handle.

Derek laughs at the expression on his face and then drops down onto his forearms, both surrounding and covering Stiles. He nips lightly at Stiles’ bottom lip and then sucks on it gently, shifting forward as he reaches for something. Stiles realizes that it’s the lube when Derek pulls Stiles’ hand away from where it’s resting on his shoulder to squeeze some of the slick onto his fingers. Derek gives Stiles one last, breath-taking kiss and then leans back to watch him as he guides Stiles’ fingers to his hole. Under Derek’s guidance, Stiles runs his fingertips over the tight pucker of flesh a few times. Derek releases his hand and settles over Stiles, waiting.

“Fuck,” Stiles whispers, suddenly freaking out just the tiniest little bit. “Derek, I have no idea what I’m doing here. I don’t want to fuck this up. Or hurt you.”

Derek quirks a small smile at him, and says, “Stiles, you’re not going to fuck this up. And you can’t hurt me. Just relax and go for it.”

Stiles fingers move almost of their own accord, rubbing light circles over Derek’s entrance. Derek squirms and arches back into his touch. Stiles frowns and says, “I call bullshit. You may have freaky healing powers, but you can still feel pain.”

“Fine, you win, you can hurt me. But I believe that you won’t. Would you rather I do it myself?” Derek asks, with a wicked grin.

“Oh, fuck,” Stiles groans, and his dick jerks against Derek’s ass. “Yes?”

Derek chuckles and spreads lube on his fingers before reaching behind himself. Derek keeps his eyes on Stiles’ the entire time, staring intensely at him. Stiles can see the exact moment when Derek breaches his own body – his pupils dilate and his breath catches slightly. Stiles watches Derek’s expressions avidly, running his hands up and down the tight muscles of his abdomen and thighs, as Derek works himself open. It might be one of the hottest things he’s ever seen. It’s moving to the top of the spank-bank list. He may have said that last part out loud, considering the snort that just came out of Derek.

“What? It’s true, you should see yourself. Oh! We should get a mirror. You could totally – hnngnh,” Stiles bursts into an inarticulate sound as Derek slathers his cock with lube, tugging firmly. Stiles’ attention is drawn out of his fantasies and back to Derek in an instant as Derek lines his cock up and starts to ever-so-slowly press back onto it.

“Fuck, Derek! You can’t possibly be open enough; you spend like ten times that amount of time on me!” Stiles exclaims, scrambling to grab Derek’s hips and stop him. It’s an act of complete futility, of course, as Derek catches his hands and holds them steady on his hips, and continues working his way slowly down onto Stiles’ cock.

“I like the burn, Stiles,” Derek says, grinning. “I want to feel the ache of your dick in me as long as my body will allow me to.”

Stiles shudders as a jolt of lust goes through him. “Fuck, Derek, keep talking like that, and this is going to be over before it even starts.”

Derek leans down from the waist, hips still pressing downwards, and growls softly against Stiles’ lips, “We wouldn’t want that.” Stiles’ hips jerk upward, pushing his cock the rest of the way into Derek’s body. They both moan. Derek steals one last hard kiss and then sits up, pressing his hips firmly down against Stiles’. Stiles can’t stop the totally embarrassing whimpery-moaning sound of pleasure from spilling out.

Derek starts off slowly, just rolling his hips and rocking gently as Stiles holds onto him and tries to match his rhythm while remembering how to breathe, overwhelmed by the tight, hot grip of Derek’s body on his cock. He’s never felt anything so amazing, not even Derek’s mouth rivals this feeling, and Derek is a champion cock-sucker. Derek is making soft little noises of enjoyment that send ripples of want through Stiles. He wants those sounds to get louder and less controlled, but he’s so lost in the tight clamp of Derek’s body, that he can’t do anything except gasp and knead Derek’s hips, trying to get him to move more, harder, faster.

Derek runs his hands down Stiles’ arms, using the leverage to lean forward and give him a long, searing kiss that goes on until Stiles is gasping for breath. With one last hard nip at Stiles’ mouth, Derek slides his hands back up Stiles’ arms and curls his hands around Stiles’ hands on his hips. “Hang on tight,” Derek says with a feral grin.

Stiles gasps as Derek’s hips begin to move in a relentless rhythm, fucking himself hard on Stiles cock. Derek groans and moans and growls, fingers tightening on Stiles’, his hard cock thrusting between them. Stiles can barely gasp in a mouthful of air before it’s pushed out of him by the force of Derek’s body rocking into the cradle of his hips. The smell of sex fills the air along with the sounds of flesh slapping against flesh and the sharp sounds of pleasure coming from the two of them. Stiles finds himself hurtling towards orgasm at break-neck speed. He digs his fingers into Derek’s hips and moans loudly when Derek suddenly stops his frantic pace, grinding down slowly, keeping Stiles right on the edge of coming.

“You close?” Derek asks, only a little breathless, that bastard. Stiles can hardly catch a breath.

“Y-yeah,” Stiles replies, unable to stop his hips from rocking upward into Derek. Derek moans and moves Stiles’ hand to his cock.

“Make me come,” Derek orders, curling his fingers around Stiles’.

Stiles starts to jerk Derek off. Derek’s hand tightens around his and spurs him on faster and harder, and suddenly, Derek’s gasping out his name and his cock is jerking in his hand. As Derek starts to come, his entire body tightens like a vise around Stiles’ cock. Stiles’ breath catches in his throat, and he hurtles over the edge into orgasm, as spurt after spurt of Derek’s come shoots across Stiles’ face and chest. Stiles bucks up into Derek, crying out with the force of his own climax. Derek waits until Stiles’ hips stop jerking and Stiles sinks back onto the bed before shifting off of Stiles to lie down beside him, catching his own breath.

Still shaking from the aftershocks, Stiles wipes the come off his cheek, but licks his lips. He still doesn’t really care for the taste of come, but the way Derek’s eyes flash red makes the bitter taste worth it. When Stiles is able to speak again, he rasps out, “Wow. Just fucking wow. That was. Fuck. That was fucking awesome. Tell me again, why we haven’t done that before?”

“You never asked?” Derek replies teasingly, throwing an arm around Stiles’ waist.

“You didn’t, either!” Stiles exclaims, giving Derek’s arm a slap.

Derek shifts closer and rests his head on Stiles’ chest. “You didn’t say anything. Every thought that passes through your head comes out of your mouth, Stiles. I just thought – ”

“Oh my God, we’re idiots,” Stiles interrupts. “For the official record, I am saying that I would like to add me fucking you to our list of sexy-time activities.” He pauses briefly, and then continues a bit more hesitantly, “Provided that’s okay with you...”

Derek leans up and brushes his lips against Stiles’. “It’s on the list. Can we sleep now?” Derek kisses him again, and then settles back down on Stiles’ chest.

Stiles grins and runs his hand up Derek’s back. “Yeah. And I totally want a mirror, too.”

“Sleep, Stiles,” Derek replies and bites him lightly on the chest.

“Okay, okay, sleeping. No need to get bitey, Wolf-man.”

Derek growls and snuggles tighter into Stiles’ body. Stiles curls his hand around the back of Derek’s neck and shuts up, falling asleep to the sound of Derek muttering Squishy Human into his chest.