Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/4168335.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M, Multi
  Fandom:
      Supernatural
  Relationship:
      Castiel/Dean_Winchester, Cain/Castiel/Dean_Winchester
  Character:
      Dean_Winchester, Castiel, Cain_(Supernatural)
  Additional Tags:
      Alternate_Universe, Alternate_Universe_-_High_School, Underage_Sex,
      Threesome_-_M/M/M
  Series:
      Part 24 of The_more_the_merrier
  Collections:
      SuperNaturallyGood
  Stats:
      Published: 2015-06-20 Words: 2376
****** boy-scout of bad behavior ******
by bloodandcream
Summary
     Cas, always so prepared for any deviant acts, had condoms and little
     single use packs of lube that he tossed on the table next to Dean’s
     head. Pulling Dean’s pants down, humping against his ass, opening up
     a pack of lube and coating his fingers, Cas was like a goddam boy-
     scout of bad behavior.
Dean groaned and stared at the pink slip in his hand. Of course he was in
trouble in too. There was a very good reason - lots of very good reasons - why
he tended to avoid Castiel at school even though they were boyfriends. Well,
maybe boyfriends was overstating it. They had an agreement. A hormone fueled,
closeted gay, sweaty kind of agreement.
Cas was… well he was a bit of trouble maker. It was kind of funny. Dean came
from a lower middle class family that managed to scrape up enough to put their
boys through Catholic school because the public schools in the area were really
bad. And Cas, he came from a well off family that were pillars of the community
and strict good Catholic people. Yet Dean was the one trying to convince Cas to
stop skipping class, telling him no you really shouldn’t pierce your belly
button with a safety pin, and why are you smoking behind the bleachers again
those things will kill you.
So detention. Because Dean had gotten caught with Cas, trying to stop him from
smoking behind the bleachers. It was maybe the third detention that Dean had
gotten in his entire high school career, which was impressive considering he
was a senior. Cas though, yeah he was in detention half the days of the week.
It really cut down on their not-quite-boyfriends sweaty sex in Dean’s bedroom
before his parents got home while Sam was still out at chess or soccer club on
Mondays and Wednesdays.
Dean loitered as long as he could while all the students leaving school fled,
wandering the hallways to the library where detention was held, backpack heavy.
He did have a lot of homework to get through. Detention could be productive at
least. Oh who was he kidding, Cas would probably try and play games or fuck
with him the whole time.
Castiel Novak, youngest son of eleven kids, was kind of an asshole. A really
hot asshole though. And god but the things he could do with his tongue. Dean
would never admit, but the shiny belly button piercing with the pink gem that
Cas had was pretty cool. But seriously, he was so much smarter than he let on
and better than serving detention all the time and acting out.
Whatever. Cas didn’t want Dean’s help, just his cock - and mouth - and that was
pretty ok with Dean.
Swinging the doors to the library open, Dean made his way to the small study
room in the back. Cain looked up at him and made a note in his attendance book
when Dean came in. It was weird, he was the only teacher that didn’t go by his
last name - everyone just called him Cain. Whatever that was about.
Cas was already there, sitting in the back row with his feet propped up. The
school uniform blazer and tie were shed and his white button down shirt was
opened by several buttons. Cas winked at Dean as he came in, sucking on the tip
of a pen he was definitely not using for writing. There weren’t any other kids
in detention today. Dean desperately hoped that more people would be there
shortly.
Shuffling in quietly he was about to sit down in the front row when Cas waved
at him, patting the chair next to him. The tables were large enough to seat at
least three students, but there were several rows and more than enough empty
tables for Dean to sit somewhere that Cas wouldn’t harass him the whole time.
“Hey Dean, why don’t you come help me with my homework?”
Dean rolled his eyes at the obvious ploy, but couldn’t help himself from moving
towards the back.
Cain rapped his pencil on the table. “Winchester. Pick your own table.”
Head down, Dean headed back to the front. “Yes’sir.”
He heard Cas huffing, but Dean was glad he’d have quiet time to do his
homework. Setting everything out on his own table, he set to studying right
away. Cas made sure to make a lot of noise in the back, clacking his pen,
shuffling his chair, tapping on the table. Cain paid him no mind, sitting at
the front and reading what looked like student papers. Dean just wanted the
detention to be over.
He was so involved in his AP Calculus homework that Dean didn’t even notice how
much time ticked by when the door slammed open and a flustered Gabriel shuffled
in.
He was a senior too, held back a year, one of Cas’ brothers.
“All adult hands on deck, the theatre kids set something on fire!”
Cain looked up at Gabe, who was notorious for pranks. “Excuse me?”
“I’m not fucking kidding man, shit’s going down and we need you in the
auditorium!”
Cain seemed - rightfully - reluctant to follow Gabe. But he was disheveled and
jittery with panic and after a few seconds Cain stood and followed the student
out. Before he closed the door he pointed a look at Dean, “I trust you two will
behave on your own for five minutes.”
Dean just nodded with a “Yes’sir” and hoped that he could keep Cas in line for
five minutes.
When the door clacked shut, he swallowed and ducked his head back down to his
book. He heard Cas moving behind him, heard the other boy shuffling closer.
Felt breath against the nape of his neck, hot, and the push of soft lips just
under his ear.
Dean shrugged him off, “Hey, man, come on we got detention for a reason.”
“Mmm, cause you’re a bad, bad boy?”
Dean turned sharply and glared at Cas. “You’re the bad boy, and I’m in trouble
because of you, so sit down.”
Cas just smiled at him, wide and wicked and oh no Dean was in trouble. “You’re
right, you are in trouble because of me. Let me make it up to you.”
Before Dean could protest, Cas was on his knees and tugging Dean’s khaki pants
open. Dean could tell himself he wasn’t interested all day long, but the thing
was, his dick was really really interested. At least he could get off in like a
minute from Cas giving him a blow job. Again. The things that boy could do with
his tongue.
Only, Cas didn’t get him off. Cas teased him. Sucked the head of his cock until
Dean was jiddering his hips forward looking for more, rolled his balls and
pressed fingers tight against the soft sensitive line leading back to his ass,
sunk teeth in to the meat of his thigh.
“Fucking, shit, Cas if you’re going to do this just do it. Cain is going to be
back any minute.”
Cas winked at him, fucking winked from between Dean’s legs on the cheap library
carpet. “Oh I’m sure my brother can keep Cain busy.”
And Dean really did not need to get in any more trouble, but he was putty in
Cas’ hands when the other boy slid off his cock and stood, bringing Dean up
too. Spinning Dean around to press forward against the table, Cas kicked his
legs apart and made a space behind him. Dean couldn’t help whimpering, pushing
his ass back. If he goaded Cas in to going faster, they’d get this over with
sooner right.
Course that didn’t lessen the fact that his pulse quickened with the dirty bad
wrong feel of it, didn’t lessen the arousal tight in his gut that they were
going to fuck on a library table, didn’t make the adrenaline of possibly
getting caught any less sharp.
Cas, always so prepared for any deviant acts, had condoms and little single use
packs of lube that he tossed on the table next to Dean’s head. Pulling Dean’s
pants down, humping against his ass, opening up a pack of lube and coating his
fingers, Cas was like a goddam boy-scout of bad behavior.
Dean bit his lip and spread his legs. Arms folded on the table, he looked back
at Cas. “Come on just fucking do it, Cain’s going to come back any time now.”
“He probably is.”
Two fingers in - or was it three - Dean didn’t care his body was lit up and
singing, fucking aching, fucking tuned to whatever it was Cas was doing back
there fucking his fingers in deep and twisting them just right.
Dean may have - totally - whimpered just a little when Cas pulled his fingers
back. Scrabbling for the condom, Dean passed it back to Cas who had it on in no
time and was pushing his thick cock into Dean while gripping on to his hips
with slender fingers. Dean’s head thunked against the table as he rocked his
hips back and cursed, fingers scrabbling on smooth formica.
Cas had both hands on Dean’s hips, pulling him back as Cas thrust in fast and
dirty, a hand on the small of Dean’s back arching his spine just so until he
had to bite his lip near bloody for the intense burst of yesyesyes that the
angle caused. So, so, so fucking close he was right there teetering on the edge
when he heard the click of the door….
“Well I knew you two were bad, but…”
Cas stilled behind him and Dean lifted his head to see Cain shutting - and
locking - the door. Shitshitshit. Ohgod. But Cas didn’t move. Didn’t pull out
and let Dean cover his blushing face. Cas just gripped on tighter and they hung
in the balance of tension for one single moment before it snapped and Cas drove
forward in to him again - fucking him for Cain to watch - and Dean couldn’t
keep back the loud moan that stuttered over his lips.
He didn’t see Cain moving but suddenly the history teacher was leaning with his
hip cocked on the table that Cas had Dean pressed down on.
Cas stroked a hand along Dean’s hip and up the curve of his back, pushing his
shirt up, exposing him even more.
“Gotta say, I’m the bad influence here, Dean is a good boy,” Dean could
practically hear Cas’ smugness.
Cain’s own voice was deep and Dean really should not be thinking about all the
hormone fueled late night wank sessions that involved most of his teachers at
some point but definitely, definitely, the gruff calm voice that Cain had and
his thick lush hair and his strong calloused hands.
Cain looked over Dean and Dean couldn’t keep his eyes open, just squeezed them
shut but he didn’t make a single move to push Cas off or get away. Fuck. He
watched too much porn, that was it, this was playing out like a porn scenario
but that had to be wrong because Cain was a teacher and he wouldn’t just -
A rough finger traced Dean’s lip. Eyes fluttering open - his ass still
clenching around Cas’ rock hard dick that was buried inside him - Dean took in
the sight of Cain with his lips parted and his cheeks flushed, who was cupping
Dean’s jaw and sliding his thumb inside Dean’s mouth.
Cain moved further around the table until he was beside Cas. “I’m sure he is a
good boy. But not incorruptible….”
Dean groaned when Cas pulled at his hips, moved him around, slid him sideways
until he couldn’t lean on the table any more but ended up folded over into
Cain’s lap. Dean had to wonder - he had to - if Cas had planned this at all or
if he was just going with it. And since fucking when was their stoic hardass
history teacher Cain a fucking pedophile. What the actual fuck.

Dean could question it all he like, all goddam day long, but Cain had a firm
grip in his short hair and Dean may have unconsciously nuzzled against the hard
line of an erect cock under Cain’s pants. Because yeah, fuck yeah, he smelled
good and when Cas started to fuck into him again with slow dragging pulls of
his cock, Dean just needed more.
So he opened his mouth and looked at Cain and whimpered.
There was a flush soft cockhead pressed against his lips in no time. Cas had
Dean’s hips in a harsh hold and was fucking in to him brutal - fucking in to
him hard enough to push him forward further onto Cain’s cock. There was a hand
in his hair keeping him up and a cock bumping against the back of his throat as
he retched a little and adjusted, squirmed under both their holds, tilted his
head and finally took Cain down even further.
Push pulled between the two of them, Dean was groaning around the cock in his
mouth - drool sliding down his chin - fucking blissed out and eyes rolled back
as he completely lost it. He lost any sense of self. Of responsibility. Of
duty. Of reality. His whole body thrummed with heat and he felt - strangely
enough - cherished and wanted and good because he was the perfect sort of thing
to get off on being man handled and shared, split between these two.
It was such a steady build, such a long time coming that he hovered on the edge
of orgasm, mind blanked, that when it finally hit him, when Cas finally pounded
against his prostate enough while he was having a hard time breathing with
Cain’s cock down his throat, Dean could only twitch and moan when he came hard,
watching his jizz spatter against Cain’s brown scuffed boots.
He felt loose and pliant, sweat making his shirt stick to his back, ass
clenching around nothing and wanting more, Cain’s come finding every corner of
his mouth to linger in, when he was finally set back down on a chair. Dean
didn’t even button his own pants. He didn’t know when that happened. One minute
he was getting fucked from both ends and the next he was slumped over his calc
homework again.
Squirming in his seat, he looked back at Cas who had the biggest shit eating
grin on his face, then up at Cain, who was perched at his desk grading papers
again like nothing had ever happened.
Maybe there was something to be said for being the bad boy.
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