From a prompt on Tumblr.
I have no regrets.
Shameless smut fic.
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The first time it came up, Derek thought he would kill Stiles.
It was right as Scott became a wolf and finally agreed to let Derek help him deal with it. Because these two had the strangest co-dependent relationship, Scott had brought Stiles along with him during "wolf lessons."
Derek was trying his hardest to be pleasant, he really was. But Stiles just would not shut his face and it got on his last nerve. He growled at him and bared his teeth, something that would make any same person cower in submission, but not Stiles.
"Oh look, the Big Bad Wolf is growling at me." He laughed. "What, are you gonna huff and puff until my house comes down?"
Derek wasn't sure his face looked like, but by the laughter coming from the two boys he probably wore his usual gobsmacked expression he usually sported whenever Stiles opened his mouth.
"I'm going to rip your throat out." He growled again. "Unless you don't shut up. I'm trying to help your friend not kill you."
"Fine." He put his hands up in surrender. "Do your wolf guru stuff."
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Derek blamed himself for the second time it came up.
Scott and Stiles kept dragging him all over this god forsaken town for things he was pretty sure they were making up. Finally he snapped at them, sick if this wild goose chase.
"Have you two heard the story about the boy who cried wolf?" He demanded finally.
"Yeah, the wolf showed up 15 minutes late to the party with a Starbucks." Stiles retorted. Derek honestly had no response to how ridiculous it was.
"Yeah." He finally growled. "And then the wolf ate him!"
"Oh look, we made the big bad wolf angry again." Stiles rolled his eyes. "What a surprise."
"I'm the Alpha here." Derek started at him before Scott blocked his way.
"Can we focus here?!" Scott demanded, trying to defuse the tension.
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The third time was the first time Derek actually laughed.
The whole pack was drunk. It was a rare moment for all of them to actually be happy, but they were. Scott was now the Alpha but Derek was 100% ok with that. He was done being in charge for a while.
To this day Derek still doesn't remember how the conversation got to this point, but Stile had started laughing randomly with everyone patiently waiting to hear what he was going to say.
"Hey guys, look!" He giggled, "I'm red riding hood!" He stood up and started to model his red hoodie as he did a drunken catwalk up to Derek. "And the Big Bad Wolf keeps trying to kill me."
Derek tried. He really did. He held a straight face for nearly a whole 5 seconds before he just burst out laughing. He didn't think he had that much to drink, but it was certainly enough to make him actually laugh at one of Stile's jokes.
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Derek lost count if the number of times afterwords that Stiles joked about him being the Big Bad Wolf. That one drunken laugh was enough to encourage Stiles, and Derek couldn't even bring himself to regret it.
Now he put on his poker face and he was positive no one knew he secretly enjoyed it.
But he shouldn't have underestimated Stiles. Somehow this crazy ADHD kid was also brilliant, and knew the affect he had on the wolf.
Neither of them were sure when they actually became friends. Somewhere along the line it actually happened though, and by the time Derek realized it, it was too late.
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The first time Derek starts it they were drunk again. Everyone had been drinking again for Stiles 18th birthday and Derek was beginning to understand why alcohol was referred to as liquid courage. The party was dying down and somehow he and Stiles were alone in the house.
"So why is it Red Riding Hood?" Derek asked suddenly. Stiles simply stared at him.
"Well, you see she had a hooded cloak that's red." Stiles said slowly.
"I get that part." Derek shook his head. "I mean the riding part. What is she riding?"
"Huh." Stiles blinked. "That's actually a good question. Maybe the wolf is a werewolf and she's riding that dick."
Derek had chosen the wrong moment to take a swig of beer because he promptly spit it out. Stiles simply smirked at him. Under sober circumstances, this is where Derek would leave. But he was far from sober.
"Well that's Red Riding Hood." Derek said, his voice going low as he leaned in slightly. "You're Mr. Red Riding Hoodie. What does riding mean to you then?"
"That I'd probably have to ride the big bad wolf to live up to the name." Stiles answered, no humor in his voice now. They were both now aware of the fact their breathing was starting to become heavy.
"Don't you always say I'm the big bad wolf?" Derek asked, their noses nearly touching.
"I did, didn't I?" Stiles breathed. Neither one was sure who initiated the kiss, but they started to in desperate hunger. Derek soon started to kiss down Stiles's throat and bio as the younger boy panted. "My, what big teeth you have."
Derek simply growled as he tore Stile's shirt off him, Derek's shirt mysteriously already off. He brought his lips back to capture Stile's as Stiles took the opportunity to straddle him against the wall. Chest to chest they started moving against each other, feeling the large bulges in each other's pants. Stiles started kissing down his perfectly sculpted chest painfully slowly.
"My, what big muscles you have." He panted as Derek let out a moan. Derek bucked against him as Stiles kissed him again as one of his hands reached under Derek's pants to firmly grasp the older boy's hard member. His eyes widened as he slowly pumped it, feeling the size. He saw the look of pure pleasure on Derek's face and kissed him slowly right under the ear before whispering "my, what a big cock you have."
That's what did it. Derek growled and faster than Stiles could keep up with Derek had ripped off both their pants and threw Stiles onto the bed face down. Derek climbed over top of him, kissing up his back and grasping Stiles dick just as firmly as his had been grabbed. He pumped slowly, appreciating that Stiles wasn't too bad him self, as Stiles moaned and withered in pure ecstasy.
He pressed his hard cock up against Stile's firm little ass roughly as he bit his shoulder. He let go of the boy's cock and firmly grasped his but, slipping a single finger into the tight hole. Stiles moaned louder so Derek added in another finger and started pumping harder, spitting onto his hand to lube it up as best as he could. He then quickly positioned himself over him as Stiles rubbed instinctively against his member.
"Better to fuck you with." Derek said as he entered him. Stiles cried out at the new sensation and it took all of Derek's willpower not to move so he would be use to it. Suddenly, Stiles began to move against him and Derek took it as an ok to start moving as well.
They found a rhythm as Derek began to pound into him, faster and faster at his wolf speed and power. Stiles knew he'd be sore in the morning but couldn't quite find it in himself to care in the moment. "Yes Derek. Oh god yes!" He chanted.
One hand still bracing himself, he moved the other to his cock and started to pump himself at the same rhythm Derek was pumping into him.
"Derek, I'm going to..." But he didn't get to finish his statement because he came just then, squirting onto his sheets. The intensity of the orgasm made Derek come inside him as well and they finally collapsed onto the bed. They moved onto their sides so that they were spooning and desperately trying to catch their breaths.
"I guess the boy cries wolf when he comes." Derek teased breathlessly.
"I guess we'll have to test if the Big Bad Wolf can blow next time." Stiles panted back.
"He can if Red can." Derek grinned as he placed his forehead on the back of the smaller boy's head.
"Do the stories ever say anything about Red falling in love with the wolf?" Stiles muttered sleepily as he turned around to face him.
"Yeah." Derek kissed him tenderly on the lips. "Right next to the part where the wolf falls in love with him." And they drifted into a pleasant sleep.