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Stiles will be the first to acknowledge that he's too curious for his own good. But in his defense, he is a nineteen year old and so everything makes him think of sex. In this case he is watching the pack train and when Derek shifts into his wolf form an idea pops into Stiles’s head and he can’t get rid of it. The idea being: does all of Derek shift and if so could he knot like wolves? And then once he starts to think about it, his thoughts spiral out of control. How will it feel? Would it be like fisting? He has seen all sorts of porn on tumblr and he knows assholes can take a lot, so a knot won’t be a problem right?
He, of course, asks Scott about it but that is a no-go area because apparently that is crossing a line. Isaac laughs at him for five whole minutes before he tells him he doesn’t know, and with a “My god Stiles, your mind” Isaac left, still laughing. Next he tries to ask Derek but he gets no further than “Can I ask you something?” because Derek says “Only if it is about pack or training” and that is that. Shut down, because Derek is a jerk.
So Stiles is now researching average dick sizes and five inch is the average. But Derek is an alpha so does that make a difference? He gets out a tape line and measures his biggest dildo, it's seven inches. He loves it, he bought it online last year and didn’t realise you are supposed to start small and work your way up to big, or very big. It took him ages to take it all the way in. Ah, good memories. Now that he knows what “big” is, he starts to look for knots, and after a delightful but slightly disturbing journey through furry town he finds a website that caters to special kinks. He hovers the mouse over the buy button for at least 5 minutes before he clicks it and fills out his information. He is curious and he has the means to satisfy that curiosity so he is going for it.
After all that, he still can’t stop thinking about Derek’s dick. The alpha wears impossible tight jeans and that means he can’t stop staring at Derek's impressive bulge. Stiles would love to watch him get into those jeans, he has this image of Derek lying on his back and wiggling his hips to get them over his thighs and ass. His mind, as usual, is all over the place. Which is a good thing, because if he lingers too long on Derek and his tight jeans the whole pack will know he is thinking sexy thoughts and that is something he wants to avoid.
Stiles had found out that Derek was bi-sexual last year and fuck him if that wasn’t an awkward month to be around the pack. Stiles dropped enough hints to see if Derek was interested in either dating him or just a one night stand but in the end had to admit defeat; Derek was oblivious to the hints or he ignored them on purpose. Anyway, let it be said that Stiles Stilinski handled rejection with class, he locked himself in his room for a week eating nothing but ice cream and Doritos, watching The Notebook and crying his eyes out. Lydia was right, this movie was awesome and everyone should have a Noah of their own.
*****
A week later he gets an email that his package will arrive the next day. He can’t stop thinking about it and he's constantly half hard. Scott tells him to please control himself, but he shrugs and says, “Sorry Scotty boy, can’t help it.”
Isaac tells him he is a pervert and so Stiles tells him, “Keep your pervert werewolf nose out of my bubble dude.”
The next day after training, Stiles tells the pack goodbye and hurries home. The mail is arriving in two hours. At least if Bernice doesn’t stop Henry, the mail man, to bother him about his dog. Then it will take two and a half hours.
His dad has an evening shift so he would not be home before eleven P.M.. He would have all the time to explore his newly discovered kink. But for now he has two hours to kill. Stiles sets an alarm on his phone and decides to take a shower after that he might start prepping himself. As he is cleaning himself he starts to think about Derek. Will he be uncut? Considering the healing factor he thinks so. Thinking about this makes his dick stir, growing harder every second. Stiles grabs it and swipes his thumb over the head, a soft moan escapes him. Fuck he needs to take the edge off. Or else he will be done in three minutes and that is a generous estimate.
Stiles gets out of the shower, he toweled himself dry and drops down on his bed. He opens the drawer next to his bed and gets his lube out, he pumps a decent amount on his hand; warms it a bit by rubbing his hands together before grabbing his dick and slowly slides his other hand behind his balls to tease his hole. As he slides the first digit in, his dick dribbles pre cum over his hand. He thinks of Derek in his horrible tight jeans, his muscled body with werewolf strength and how he can easily fuck Stiles against a wall. Holding him up and fucking into him or letting Stiles fall down on his cock over and over, and there we go, Stiles cums with a groan. Thinking about Derek is always a quick and sure way to cum within minutes. He lies on his bed fingering himself lazily while thinking up scenarios of how he could seduce Derek into his bed.
The alarm on his phone goes off and Stiles gets up, he wipes himself off with a wet towel and washes his hands. He slips on his jeans and throws on a shirt, fuck it, he is actually nervous! He gets downstairs and sits down at the kitchen table, he gets up again and walks to the front window to see if Henry was already on this side of the road, he wasn’t. He forces himself to sit down and play candy crush not looking at the time at all. He jumps when the doorbell rings; fuck his package was here! He calms himself down enough to open the door and take the package. Holy fuck he was really going to do this!
Of course his father isn’t coming home early, but he is still a bit weary, so when he walks into his room he locks the door for good measure. He sits down on his bed with the biggest grin on his face. He opens the package and takes out the knotted dildo. He rubs his hands all over it, he tests the girth of the knot and likes how it feels soft but firm at the same time. He can feel his hole clench at the mere thought of sliding it inside. He pulls down his comforter and lies the newly acquired toy down in the middle of his bed, it looks obscene against his white bedsheets. He wants to take a picture; but refrains, best not to have evidence. He grabs his lube and places it on the bedside table. When a loud noise startles him. He glances at the window in a mild panic, when he sees it open in what feels like slow motion he already knows who has the balls to enter his room through the window at any given time, Derek fucking Hale.
Okay, so he isn’t going to do this now. He hurriedly shoves the lube back into the drawer and pulls the comforter over the dildo in a mess so the outline couldn’t be seen. He hopes with all his might that Derek didn’t see anything.
“Jesus Derek, if you are not going to ring the doorbell at least knock on the window!”
Derek’s nose twitches and his eyes flash red. “What the hell Stiles, it’s the middle of the day, can’t you jerk off at night like a normal person?”
“Nope, I can’t, because I am not a normal person. Can I help you with something or are just using your nose to interrupt my alone time?” Holy fuck, Derek’s ears are turning red. “Did you actually use your nose to sniff out my alone time?”
Derek clears his throat, “You need to find us everything on fairy rings, we found several of them in the preserve.”
Stiles sighs, and walks to his desk to get his laptop, when he turns around he sees Derek standing next to his bed with the giant knotted dildo in his hands.
Stiles flushes and makes a grab for it. “That’s personal!” but Derek sidesteps him and turns it over in his hands. “Is this a knot? Really Stiles? You actually went there?” Stiles glares at him “Yes it is and yes I went there, it’s none of your business” Derek gives him a look and lifts an eyebrow at him.
Despite his embarrassment at being caught Stiles answers, “This is all your fault, so don’t look at me with those judgemental eyebrows mister I-wear-sinfully-tight-jeans!”
Derek huffs, “How is this my fault? and what is wrong with my jeans?”
Stiles makes an exaggerated noise and decides to just go for it. “Nothing is wrong with them, they just look like you painted them on! They show off everything! Everything, Derek! And then you decide to tell Isaac about your freaking boyfriend in college which makes you bi and that made me think I had a chance!! But nooo, you ignored all my hints and flirting and then you wolf out during training and you know me! My mind works overtime and sure enough you wolfing out meant my brain went there yeah and because this is 2016, I have easy access to explore my kinks anonymously! Scott went weird when I asked him about it and Isaac laughed in my face. And if no one is going to tell me anything, well then I am forced to look for answers myself. And no, I couldn’t ask you because you made it clear you weren’t going to answer any questions other than pack or training ones.”
Derek is silent and stares at him. Stiles can’t handle the silence and he clears his throat “So yeah that, say something or go away, so I can jerk myself off in peace.”
“I thought you were making a joke. Sure you smelled of arousal, but then you always smell of arousal so that was nothing new.” Derek seems torn for a second, “So ask me now.”
Stiles looks at him, takes a deep breath and spills what has been on his mind for weeks. “When you shift form, can you knot? Does the fact that you are an alpha influence the size of your dick? Are you uncut? And is that because of the healing?” He sits down on his bed and while he waits for the answers.
Derek is silent again and when Stiles looks at him he sees Derek is shaking with silent laughter. “Oh my god, you are actually laughing at me. I am done with you, go away!” Stiles turns away from Derek and lets himself fall onto his bed face first in his pillow.
He feels the bed dip and when Derek pulls him around he goes without resisting. “Okay sorry, I do not have a knot.” Derek says softly “No, me being an alpha doesn’t change the size of my dick.”
Stiles lets out a breath he didn’t know he was holding and looks up at Derek, “And are you uncut?”
Derek looks at him and gives him a grin. “Would you like to find that one out for yourself?”
Stiles nods vigorously. Derek leans back, he pushes Stiles’s legs apart and settles between them. He then leans forward and kisses Stiles for the first time. The kiss is better than he ever imagined, Derek kisses like he is drowning and Stiles is his air.
Stiles can feel Derek’s want in the kiss and it turns him on more than he thought it would.
Stiles lets his hand slip behind Derek’s head he curls his fingers in Derek’s hair and deepens the kiss. Derek groans and shifts his hips pressing them down looking for friction. Stiles pushes up into him and tightens his hand pulling a needy sound from Derek. After a while the filthy kissing and the slow grind just isn’t enough any more.
Stiles tenses and flips them over, now straddling Derek he looks down, “You are wearing entirely to much clothing for my examination.” He shifts his ass into Derek's straining dick and feels satisfied when Derek shudders.
Derek pulls him down and kisses him hard, “Do you have lube?”
Stiles nods and reaches over to grab the lube from his bedside table drawer. Derek sits up and Stiles slides further down into his lap making them both groan at the pressure. He kisses Stiles again before he pulls off his shirt and tugs Stiles’s shirt off, when stiles leans forward and kisses Derek. Their skin to skin contact is hot and sweaty, but so good. Derek slides his hands down Stiles’s back and follows the edge of his jeans towards the front, he rubs at the outline of the erection he finds there and pulls away from the kiss he looks at Stiles “Can I?”
“Go for it big guy” so Derek does, he pops the button and pulls down the zipper, he urges Stiles up so he can slide the jeans down enough to have access to Stiles’s dick. Derek thumbs at the head and spreads out the pre cum leaking from the tip, he lifts his hand and looks at Stiles while he sucks his thumb into his mouth.
Stiles’s eyes go wide and his pupils blow up “Fuck!” he gets up and almost brains himself in his haste to get his jeans off, he turns back to the bed to look at Derek “Off please, you need to be naked”
Derek smiles and gets up, he drops his jeans and gets back on the bed, Stiles is still standing next to bed and staring at Derek’s dick with an hungry expression on his face. He grabs Stiles’s hand and pulls him onto the bed, manoeuvres him into his lap and kisses him. The kiss turns desperate after mere seconds and Stiles pushes Derek away and into the headboard, he kisses his way down to Derek’s beautiful uncut monster cock, it’s longer and wider than his dildo. He can actually feel himself start to drool he licks his lips and looks up at Derek who is looking down at him with a amused and sort of fond expression on his face.
Stiles flushes “I need you to keep your hands on the headboard okay? I’ve been practising deepthroating for a while now so I think I can do this but you are a big boy and I don’t feel like choking on your dick while giving my first blow job. Can you handle that?”
Derek makes a noise but he nods and stretches out his arms to grab the headboard.
Stiles smiles and settles down in a comfortable position he grabs Derek’s dick and slides his hand slowly up and down, his uses his other hand to fondle the tightly drawn balls. He bends his head and licks at the slit, not a bad taste, he licks around the head as he tries to remember what he does with his tongue when he deep throats his dildo, he decides to wing it and as he sucks the head into his mouth he feels Derek jerk and he knows he is doing good so far.
He lets the dick slide in further and further until he can feel it at the very end of his throat he swallows around the head and chokes when Derek jerks up. He pulls off and glares at Derek “Sorry, couldn’t help it” Derek sounds wrecked and that makes Stiles focus back on Derek’s dick, he tongues the slit. He lets the head slide inside and while it rest on his tongue, he prepares himself mentally. He puts his hands on Derek’s hips to keep him pinned to the mattress while simultaneously sliding down his dick and this time when he swallows around the head he has a strong enough grip on Derek’s hips to not choke. And when he slides down again and again, he basks in Derek’s groans and the utter nonsense spewing from his mouth, he knows he is doing a good job.
When he feels Derek’s hand on his head he looks up and pulls off with an obscene, wet pop. Derek drags him back up into his lap and kisses him. Stiles starts grinding down and Derek gropes around for the lube, he grabs it and pumps a few times and rubs his fingers together. Derek slides his fingers over Stiles’s hole, he shivers and feels his muscles contract. He pulls back and looks at Derek "I am not pressuring you or anything right? Are we really doing this?”
Derek smiles “No, you idiot and yes we are. Unless you don’t want to?”
“Hell yeah I want this, bring it on! Sex me up, wolf man!” Derek rolls his eyes and slips the first digit in all the way to his second knuckle Stiles gasps and shudders while dropping his head on derek’s shoulder. Derek slides his finger in and out a few times before adding another one Stiles is mouthing at his neck and places soft kisses over the side of his face until he can kiss Derek’s mouth.
Their kisses becoming more and more desperate the longer Derek is fingering him, and when Derek slides in a fourth finger Stiles sits back and groans when he forces Derek’s fingers in deeper “I am ready for fuck’s sake Derek, get your dick in me now!”
Derek pulls his fingers out and urges Stiles up on his knees and turns him around when Stiles looks at him over his shoulder he says “This way you can control it” he grabs the lube and gets a generous amount on his dick and positions it at Stiles entrance he looks at him and waits.
Stiles sinks down a bit and moans when he feels the head getting caught on his rim before it slides in, he sinks down a bit more and pulls up again, he repeats this until it is completely inside. He feels so fucking full, every movement sends a tingle down his spine and the burn is making his eyes water; but it feels so good, he feels owned and claimed. He looks back at Derek and sees him looking intensely down at where they are connected and when Derek looks up his eyes are completely red. Stiles lifts his hips a few times letting gravity pull him down, Derek let’s out a whimper and Stiles feels Derek’s hands tighten on his hips; he is loving the control he has. He quickly finds a rhythm that works for him and he fucks himself hard on Derek’s glorious dick. Stiles changes the angle a bit and the next time he sinks back he sees stars. The feeling of Derek’s dick dragging over his prostate makes him lose control, his thrusts becoming erratic and his spine arches up as he cums untouched. His arms give out and he drops to the bed trying to catch his breath. He realises Derek is still rock hard inside of him and he clenches his hole. He hears a low growl and he shivers at the sound.
He looks back at Derek and sits up, the downward slide makes Derek’s hips stutter up. He twists his head so he can kiss Derek and then murmurs against his mouth “Fuck me, big guy, fill me up and make me yours.” Derek growls and pushes him forward and Derek moves with him so they stay connected, Stiles lands on his elbows but before he can get his bearings Derek grabs his hips in an almost painful grip and starts moving, the first few thrusts are shallow but then Derek finds his strength and starts fucking him with deep hard thrusts all the way to the hilt.
Stiles drops his head and tries to move with Derek squeezing his inner muscles every time Derek pulls out, Derek loses his rhythm and lets out a low growl while pumping his hips in slow stuttering thrusts. Stiles feels Derek’s cum, hot and wet, dribbling out of his hole with every thrust.
Derek pulls out and turns Stiles around to kiss him soft and sweet, they lie together for what feels like an eternity but is really maybe closer to thirty minutes. Stiles tries to move but his whole body protests “You broke me with your monster cock, go get something to clean us up because I am not moving any time soon” Derek rolls his eyes but gets up and comes back with a wet towel, he cleans them up and lies back down.
Stiles yawns “We’ll talk about all of this after a nap, you wore me out. Do not sneak away because I will find you and I will end you!”
Derek smiles and kisses him softly “I’ll be here, we’ll talk.”
“I think I am halfway in love you” Stiles murmurs into his pillow.
He can’t be sure but he thinks he hears a “Me too” at the back of his neck which makes him grin like an idiot before he drops off to dreamland.