Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/3536135.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Teen_Wolf_(TV)
  Relationship:
      Derek_Hale/Stiles_Stilinski
  Character:
      Derek_Hale, Stiles_Stilinski
  Additional Tags:
      Just_the_Tip, Bottom_Derek_Hale/Top_Stiles_Stilinski
  Stats:
      Published: 2015-03-13 Words: 1379
****** Loop Holes ******
by stonerskittles
Summary
     They’d come to an agreement.
     Or, the Sheriff had sat them down, looked Derek straight in the eyes
     and said “No sex until he’s 18.”
     It took Stiles approximately half an hour to discover a loop hole.
Notes
See the end of the work for notes
They’d come to an agreement.
Or, the Sheriff had sat them down, looked Derek straight in the eyes and said
“No sex until he’s 18.”
Stiles, of course, had protested until he saw his father’s glare. “No sex,” he
echoed, pouting a little.
The Sheriff – John, he’d said to call him – nodded before pausing and squinted
his eyes suspiciously. “That means no penetration of any kind, and
no fondling.”
Stiles huffed, opening his mouth, but Derek got there first. “Yes, sir. We
understand.” Glaring at Stiles pointedly. Stiles bit him.
Sheriff- John – nodded and stood up swiftly, clapping Derek on the shoulder as
he passed. “Good talk.” He scrubbed a hand over Stiles’ buzz cut briefly. “Be
good.”
–
It took Stiles approximately half an hour to discover a loop hole.
 
“Dad said,” he gasped against Derek’s mouth, hips stilling for a second. “Dad
said we can’t penetrate each other, right?”
Derek sighed. “What have I said about mentioning other people when we do this?”
Stiles smacked his chest. “Hear me out. No penetration. So if I sit over here,”
Stiles got up and sat at his desk chair, facing Derek. “And if you stay there,
we can get off without breaking any rules.”
That was- kind of smart actually. “Let’s do it. You have any lube?”
Derek smiled as Stiles flailed in his hurry to pass him the plump, half full
bottle. In no time, they were both undressed and Stiles was flushed, mouth open
and legs spread as he fisted his erection.
Derek, on the other hand, took it slower. He teased his nipples, dragged his
fingertips down his chest to run through his coarse pubic hair. He jerked
himself off for a few moments, feeling Stiles’ heated gaze on him the whole
time.
When he was fully hard with beads of pre-come forming at the tip, Derek twisted
his body so he was on his hands and knees.
“Wha-what are you doing?” Stiles stammered as Derek coated two fingers with
lube.
“Watch,” Derek grunted, letting one lubed finger circle his hole, tilting his
ass up higher. He moaned quietly as the finger breached him, sinking all the
way in with no resistance at all.
In the chair, Stiles began to pant. “Fuck, Der. Look at you; so beautiful. Can
you add another finger for me? Just one. Would you do that for me?”
Derek did, crying out at the slight burn and Stiles had to squeeze the base of
his cock tightly or he was going to come.
Stiles made his way to Derek, kneeling behind him. Gently, as if not to startle
him, Stiles placed his hands on Derek’s hips. “You look so good like this,” he
blurted out, making Derek’s breathing hitch.
It wasn’t something they’d ever discussed; talking dirty that is. Mostly
because Stiles was a virgin, wasn’t quite sure what he liked or didn’t like yet
and Derek himself hadn’t experienced that yet.
Frankly, he’s a little alarmed at how much he liked it. Heat flared through his
body at Stiles’ words, made his hole clenching involuntarily with the need to
just get Stiles in him already.
“Stiles,” he shudders, “Touch me.”
“I am touching you.” Stiles said, gripping Derek’s hips tighter to illustrate
his point.
“Fuck. You know what I mean,” Derek was not above whining. His dick is drooling
pre-come into Stiles’ sheets, three fingers now pumping inside him and Derek is
ready.
“I’m not sure I do,” Stiles teased.
Derek growled, pulling his fingers out to grab one of Stiles’s hands and place
it on his ass. Stiles rubbed the pad of one finger against his rim, slipping in
slightly as Derek thrust his hips back.
Stiles tittered. “That’s against the rules, Derek.” But he continued the
rubbing, slowly driving Derek insane.
“Please.” Derek squirmed in attempt to get Stiles where he wants him. “Just
your fingers, please.”
Abruptly, Stiles pushed two fingers inside Derek, crooking them up and slightly
to the left. They rubbed at his prostate and Derek was done. His whole body
jerks, in an attempt to get Stiles closer or away, he doesn’t know, but his
legs are shaking and his balls are drawn up tight, erection an angry red.
Derek is just on the edge of coming, can feel his body tense as he moans
wantonly. “Stiles! I’m-”
But then the hands are gone, and Derek is left panting and confused. “What?” He
manages weakly, barely audible with his face buried in the sheets.
“I’ve decided,” Stiles says casually, as if his fingers were not just up
Derek’s ass and he wasn’t two seconds away from coming. “I want you to take my
cock.” Said cock was grinding between his ass cheeks, leaving the skin slightly
sticky with pre-come.
“Do you want my cock, Derek?”
And that just wasn’t fair. Stiles’s voice was low, slightly husky and filled
with arousal. Still, Derek made an approving noise in the back of his throat,
nodding almost frantically.
Stiles laughed, like he wasn’t affected at all, but Derek felt the hands on his
hips tighten- almost too tightly, if he were human, he’d have bruises for days
– before they left to grip at his cock, holding it steady as he pushed the head
into Derek.
“Just the tip. This is all you’re allowed.”
It wasn’t enough, Derek wanted to protect. His hole was so loose and slicked
up, there was no way it would be enough. Instead, Derek unclenched one of the
hands twisted into the material of Stiles’ cover, spat in it and brought it to
his cock, setting a torturous pace as he fucked into his hand.
Stiles rocked his hips, sliding the tip of his dick in and out of Derek slowly,
revelling in the feel of Derek clenching around his cock, as if he was hungry
for it.
“Stiles,” Derek says, sounding breathless. “More. I need more.”
“More?”
“Please.” He gasps.
“You’ve been so good,” Stiles coos. “You can have a little more.”
On the next thrust Stiles let half his cock press into Derek’s slick heat,
emitting a deep groan when he looks down and sees his cock in Derek. His rim a
dark pink, stretched tight over Stiles’s dick.
“Beautiful.” Stiles says quietly, mostly to himself.
Still, Derek mewls in reply, taking Stiles off guard by sliding his body back
and taking all of his cock in. Derek lifts his head back, moaning in triumph.
Stiles laughed darkly and gripped Derek’s shoulders. “You shouldn’t have done
that.”
Derek’s hips stuttered, his breath coming out harsh and uneven. Stiles’ hips
snapped into Derek’s, pace rough and unrelenting. Suddenly Stiles was pulling
him up so his back was to Stiles’ chest. The new angle meant that Stiles’ cock
stabbed at his prostate on every thrust.
With one hand on his cock and Stiles pounding into him, Derek knows it isn’t
going to be long before he came. His dick is leaking steadily now, and the head
is flushed a dark red, he’s so hard it’s nearly painful.
Derek was getting louder as he gets closer to the edge, inhaling desperately
and damn near wailing when Stiles pinches his nipple between two fingers. All
the combination sensations is too much, and with Stiles panting in his ear,
muttering curses and how he’s going to come inside Derek, plug him up so he’s
still slick and loose for when they next fuck. How he wants to see Derek ride
him, wants to ride Derek and-
Derek comes, lost in the image of Stiles sinking onto his cock and seeing his
mouth,Christ that mouth open, lips red and swollen from swallowing down Derek’s
cock.
“Fucking, fuck.” Stiles groans unmistakably and bites down on Derek’s neck.
After a few minutes and they’ve got their breath somewhat back, Stiles pulls
out to which Derek makes a small noise of protest but doesn’t stop him.
Choosing instead to move up the bed and make room for Stiles to lie next to
him.
“Dad doesn’t find out about this.” Stiles states.
Derek sighed. “Stiles, what have I said-”
“Yeah, I know.” Stiles laughs and turns his back to Derek. “Now cuddle me.”
“Yes, dear.”
Derek shakes the bed with his laughter when Stiles hits him, even though he’s
smiling fondly.  
End Notes
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