Stiles always seemed to wind up alone in the car with Derek. At first this had seemed very strange to Stiles. After all, Stiles was the most ordinary of all the people Derek could ask for help in these matters. Even when things were very tense and there was a firm battle line drawn between "Scott's" pack and Derek's, the older man had still asked Stiles to go on these sorts of missions with him. It had baffled Stiles to no end, so one day, after tensions had eased and Derek was more willing to actually talk with Stiles, he had asked.

"You might be physically weaker or more vulnerable than the others," Derek had said, "but you never let that stop you. Besides, I'm strong enough for the both of us; I'd rather have someone with me who can think." At the time Stiles had felt almost overwhelmed by the comment. He tended to think his contributions to the goings on were negligible but Derek seemed to find him equally, if not more, capable of handling any given situation.

So here they were again, in Derek's car for once while the jeep was out of commission, on what was basically a stakeout. They were keeping an eye on a small warehouse where they thought the latest beastie might be hiding, and they'd been sitting in the car for hours. Things were easier between him and Derek now, but Stiles still tried to keep a lid on his rambling because it would eventually get on the alpha's nerves. Still, after hours of sitting in silence staring at what seemed to be an empty building, Stiles couldn't help but talk.

"So…" he started, shifting and fidgeting slightly," what size condom do you use?" Derek's chin lifted a few inches and he turned toward Stiles with his 'are you kidding me' glare that still seemed to pop up whenever Stiles opened his mouth in the car. "Oh come on, how can I not ask? I mean seriously, 'they wouldn't fit'? How big does it have to be…"

"Stiles!" Derek interjected roughly, cutting the younger man off. Stiles fidgeted again, glancing out his window and licking his bottom lip.

"You never know, someday you might be busy with wolfy shenanigans and need your buddy Stiles to make a fun run," Stiles offered as an excuse, knowing full well that nothing could compel Derek to do so. The older man sighed.

"They're in the glove box." Stiles shifted in an excited way, proud to have won, and opened the glove compartment. He pulled out a small black box. He looked incredulously at the package before sliding out a condom and closing the rest back in the small compartment. He flicked the wrapper back and forth nervously as he tried and failed to keep his eyes from darting toward Derek's crotch.

"God that's unfair," Stiles sighed. He propped his elbow against the door and cradled his head in his free hand, making a sort of disgusted face at the condom. Derek returned to staring at the warehouse, his jaw set in an aggravated kind of way. Silence returned to the car. Derek was just starting to relax again when Stiles let out a strangled sort of whine and blurted out,

"Have you had sex with Erica?" Derek whipped back toward him with a threatening glare. "I know this is none of my business…" Stiles tried to let it go with that, he really did. "But she's been kinda… 'sex positive' since you turned her and I sometimes wonder if that's what you intended. Like a werewolf sex… thing." Stiles was trying not to look at the anger in Derek's eyes.

"No," the werewolf said flatly, angrily. Stiles let out a sigh of relief.

"Good because that might be kinda…"

"She wants to," Derek grumbled, now studiously avoiding eye contact himself. Stiles let out an incredulous laugh.

"That's not really… I mean look at you. You probably have women throwing themselves at you. You have a box of condoms in your car for god's sake," Stiles said, holding up the one in his hand as evidence.

"It's not like I can keep them in my nightstand," he ground out. It was true, Derek lived in one shithole after another; keeping condoms in your nightstand is out of the question when you don't have one. Stiles started fiddling with the condom unconsciously, turning it over and around between his fingers.

"Still, the car's gotta be like catnip," he said nervously. "I mean who wouldn't want to have sex in this baby? I'd probably let you do anything you wanted to me if it was in this car," Stiles said, honestly marveling at the sleek black Camaro. Derek visibly stiffened. "If I was a girl, I mean!" he corrected, realizing it sounded like he was propositioning Derek. He palmed the condom in an attempt to stop playing with it.

Silence reigned again, this time very awkward as Stiles burned with embarrassment and tried to make himself smaller in his seat. They sat like that for about an hour but as time wore on Stiles began to relax. Once Stiles had stopped being embarrassed his mind had started up again. He shifted so that he could look into the back seat, turned back again, glanced at Derek, turned around once more, and finally settled into the seat.

"How does that work anyway?" Stiles asked. Derek looked at him, mild confusion in his eyes.

"How does what work?" Derek asked calmly.

"Sex in this car?" Derek's jaw tightened, his eyes hardened, and he exhaled heavily though his nose. This was Derek's seriously annoyed face. Stiles didn't seem to care. "I mean, you're kind of a big guy," he paused, tripping over the unintended double entendre, "Seems like you and another person couldn't fit back there…"

"Stiles!"

"Especially if you were bumping and grinding…" Suddenly Derek was leaning across Stiles, aggression pouring off the set of his shoulders. Stiles straightened up and pressed himself against the back of the seat. Derek pulled up on the small handle between the seat and the door and Stiles and the passenger seat fell into full recline. "Oh," Stiles said with mild surprise. Derek sat back in his seat, hands gripping the steering wheel tightly, jaw locked, and sharp eyes focusing intently on the horizon.

Stiles didn't remain still for long. After a moment his eyes and head were surveying his new position, analyzing its merits. He leaned up on his elbows, lay back down, and stretched out his legs. He paused for another minute then tentatively lifted his knees toward his chest. Derek growled low and menacing and Stiles stretched his legs back out. He just laid there, hands resting on his abdomen, for a few minutes. Then his eyes were wandering again.

"How would you get a blowjob like this?" Again Derek's chin lifted, the body language indicating he might strangle Stiles if he didn't shut up. Stiles still seemed oblivious. "I mean you can't really…" Stiles scooted down in the seat, trying to work out the position and failing before sliding back again. "Bet then the other way you'd be like… crawling over them…" He was sideways leaning on his elbow when Derek let out another growl. This time Stiles seemed to notice because he didn't turn over the rest of the way to mount the headrest. Now he was just staring at Derek, waiting for an answer. Derek wondered how anyone could have so little shame. After twenty minutes of Stiles staring at him expectantly with his mouth slightly open, Derek let out an exasperated sigh.

"It's generally easier to do that before you're both in the passenger seat," he answered begrudgingly. Stiles sat up.

"So what, you just lean across the stick shift and go to town?" Stiles asked, leaning forward so that their shoulders pressed together and looking down at Derek's lap.

At this point Derek had had enough. He grabbed Stiles roughly and slammed him back onto the passenger seat. When he returned his hand to the steering wheel his knuckles were white with the tightness of his grip. His overall body language was more stiff and menacing than it had been all night. Still, Stiles was back on the subject almost immediately.

"Is it hard to get… fluid stains out of the upholstery?" Stiles asked seriously. He seemed to ponder it a moment. "Is it hard to get your pants off? I mean, there's still not a lot of room to maneuver…"

"Stiles!" Derek was looking at him with those wide, incredulous eyes. "Do you want a demonstration?" he asked aggressively.

"Whoawhaaa-" was the sound that came out of Stiles' mouth. Derek's eyes gave him a quick once over and then returned to lock on Stiles. Somewhere in Stiles' brain it registered that Derek was serious. His mouth opened and he released a sort of disbelieving 'huh' before nodding deliberately.

Derek slipped off his jacket and hung it on the headrest. Then he was on top of Stiles, somehow moving from the driver's seat to the passenger's without any struggle. Derek's mouth, apparently eager to devour Stiles, was locked on his in the most passionate kiss the younger man had ever known. His hips were rocking against him in a way that stopped Stiles' brain instantly. Then Derek's hands were under his shirt, feeling him, touching him. Stiles had some vague notion that he should reciprocate but he'd gone from zero to ecstasy in 0.5 seconds and he couldn't remember how hands worked. Derek didn't seem to mind.

After they'd been making out for a solid ten minutes Derek paused to remove both of their shirts. And now Stiles remembered how hands worked because he had wanted to feel up that perfectly sculpted torso forever. One hand reached up to feel every muscle of Derek's upper body while Derek leaned into him, now attacking his jaw line, neck, and collar bone. The older man was kissing and biting him, and Stiles never knew biting could feel so good. He focused on breathing.

When Derek's fingers started unfastening his jeans he let out a strangled gasp and had to really think about inhaling and exhaling because he was so aroused and he wanted this so badly. He was glad Derek was handling this part because he knew instinctively that that button would have taken him an hour to undo. And even though he had asked about getting the pants off he still had no idea how it worked when they were both completely naked.

Somewhere at the back of his mind Stiles realized that he was naked in a car just parked on the side of the street. Somewhere it registered that someone, anyone, could find him at any moment, naked and horny and about to lose his virginity to Derek Hale in his sexy black car. But that didn't really matter to Stiles right now because he was naked and horny and about to lose his virginity to Derek Hale in his sexy black car.

Stiles had a brief moment of confusion as Derek's fingers scraped across his, trying to pry them open without taking his attention from Stiles' neck. But then Stiles realized that he was still holding the condom he'd taken earlier and Derek wanted it. He opened his hand and let Derek take it, whimpering slightly when he paused to put it on. And Derek hadn't been lying about the size either.

Stiles tried to fight off a sudden bout of panic as he thought about what came next. Derek was huge and Stiles a virgin and this was going to hurt. But Derek was leaning into him again, gripping his cock now, and kissing him, and even though he was still nervous he felt too good to work up a real panic.

"Relax," Derek whispered seductively in Stiles' ear. And Stiles did relax because it quickly became apparent that Derek was a pro. His hand shifted and he was using his fingers, covered in lube from who knows where (the glove box, had there been a bottle there?) to carefully stretch and prepare Stiles for what was coming. When he was finished he whispered it again, and Stiles relaxed just a little more because he knew Derek would be gentle with him.

It did hurt, but in all the right ways, and Derek took his time to let Stiles adjust. He resumed the passionate kissing, possibly to distract Stiles from the pain that was completely unavoidable. Really it was unnecessary because he had also resumed stroking Stiles' dick, matching the rhythm to his thrusts which were slowly quickening.

It wasn't long at all before Stiles was coming hard in Derek's hand. A few more quick thrusts and Derek was coming too. Then he just sort of lay on top of Stiles, breathing him in. Stiles absently traced the spirals tattooed on Derek's back, soothing them both, cooling off. Eventually Derek propped himself up a bit. He gave Stiles a few lazy kisses where his jaw met his neck, just below the ear.

"Satisfied?" Derek whispered huskily.

"Mmmmm," Stiles hummed. "Might have to show me again later." Derek smiled warmly, happily.

"I can definitely do that," Derek replied, the slightest hint of amusement in his voice.

Then Derek was moving, cleaning up. He disposed of the condom in a small sealable trash bin tucked under the driver's seat then wiped Stiles' semen off the both of them with his shirt and slid his underwear and pants back on. He slid back into the driver's seat and covered Stiles with his jacket.

Stiles recalled vaguely that they were on a stakeout; the sex had been a gross dereliction of duty. He knew he should dress himself, put the seat up, and help Derek keep watch, but he couldn't muster the energy required. He stared at Derek's profile. The werewolf had gone back to watching the warehouse with a self satisfied smirk. He brought Stiles along to think, Stiles recalled, and he was thinking. He was thinking about everything he would do next time, how he would make Derek feel so good. And then eventually he was dozing off, the strong safe scent of the alpha lulling him into sleep.

Author's Notes:

Thanks to NinjaPandaIzzy for looking this over for me before I posted and giving me helpful input on elements that needed tweaking.

Thanks to all of you who reviewed chapter 1 and encouraged me to write more. I know this isn't exactly what you guys asked for, but I hope you'll be satisfied.