Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/1274344.
  Rating:
      Explicit
  Archive Warning:
      Choose_Not_To_Use_Archive_Warnings, Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Castiel/Jimmy_Novak/Dean_Winchester
  Character:
      Castiel_(Supernatural), Jimmy_Novak, Dean_Winchester
  Additional Tags:
      Pure_Smut, Age_Difference, Alternate_Universe_-_Student/Teacher,
      Threesome_-_M/M/M
  Stats:
      Published: 2014-03-06 Words: 10631
****** Double The Trouble ******
by mooseilicious
Summary
     Jimmy's failing his English class and needs a tutor, and whose better
     than the actual teacher himself?
Notes
     An old rp I had dug up from a while ago (◡‿◡✿)
[[high school AU]]
English was one of his favorite classes, filled with literature that he
enjoyed, lectures that held his interest, and a teacher that was pleasing to
watch. Before class had started, he was taken aside by said teacher, with
confusion written all over his face. It turned out that he was failing and his
scores needed to improve in order for him to graduate. "Talk to me after
class." He was told as the bell rang to start classes. And he did. Class passed
by quickly, his eyes on Mr. Winchester the whole time, and before he knew it,
the period was over. Students filed out of the classroom, bidding their
'goodbyes' and 'see you tomorrows' as he packed his things and went over to his
teacher's desk. "Mr. Winchester?" Jimmy stood in front of the desk, fidgeting
nervously with a book bag strap. "I've been thinking and.. Do you think, it's
possible if you could tutor me? I haven't been studying well, as you said, and
I have club activities after school usually." He looked at his teacher with
wide eyes, fawning innocence as he worried over his lower lip in anticipation.
Dean looked up from the paper he was currently grading to gaze at his student,
listening intently as the boy spoke. He nodded slowly when the youth had
finished, and spoke in a thoughtful tone. "Yes, tutoring would be fine. Feel
free to come in anytime before 4 after school, as that is when I go home. I'm
glad you see the importance of getting your grades up, Mr. Novak. Getting into
a good college depends on good grades." He flashed a brilliant smile before his
eyes returned to his work, checking off wrong answers quickly so that the paper
was done. He glanced up at the clock then, then looked up at Jimmy once more.
"I suppose, since you are here now, we could get started. Do you have your
failed assignments with you?"
"Actually-" He blurted right after the last word was finished, clamping his
mouth shut immediately. "Sorry sir, but.. I was actually wondering if you could
come to my house or something. I have swim practice in a few minutes and if I'm
late, Coach will give me extra laps." Jimmy made a miserable look, casting his
eyes downwards as he chewed on his lower lip. "I- I know that's asking a lot
and I understand if it's not possible but.. I don't really have any other time
to come in." He winced at his words, chiding himself mentally with a sigh as he
shifted his weight from one foot to another.
One brow raised in contemplation before Dean nodded, smiling softly. "I have
cross country practice to coach on Mondays, Wednesdays, and Fridays at 4. After
5:30, I'm free the rest of those three days. Otherwise, I'm free after 4 on
Tuesday and Thursday, and all day on weekends." He paused, hoping that the
student got all that. He didn't want to overload the youth's mind with
information. "What time does your practice end today, Jimmy?"
The times were cataloged into his head, easily matching them with his schedule
with an internal smirk that his face didn't show. "Oh um.. 5:15." That was if
he got to practice on time and not a few minutes late. Jimmy glanced over at
the clock and muttered under his breath. "Um.. So I guess I should give you my
address then?" He swung his bag over to fish out a scrap of paper and a pen,
hastily scribbling down the street and his phone number just in case. "I have
to go Mr. Winchester. Coach will have my head if I'm late again. Just.. Text me
or something if you're okay with tutoring me later. Thanks." The paper was slid
across the desk before he turned, giving one last wave before he was running
down the halls to the locker room to change.
Dean smirked as he took the slip of paper, nodding to Jimmy. "I'll be there,
don't you worry," he called out as the student left. He glanced down at the
paper in his hand, biting his lip as he slipped a hand into his pocket to pull
out his phone. It was probably wrong to keep a student's number and address but
as long as it was only for tutoring purposes, it was okay. He hoped. After
saving the number in his contacts, he stuck his phone back in his pocket and
sighed, glancing over at the clock. 3:15. He had two hours. He supposed he'd
better get to grading then if he wanted to make it home by 4. The address Jimmy
had given him was actually not too far away, so it wouldn't be hard to get
there. He picked up his pen and looked down at the papers, breathing out
another sigh as he began grading them.
Luck was on his side, barely, as he scampered into the locker room to shuck his
clothes off and shove on his speedo. By the time he busted through the door
that lead over to the pool, the coach had just began to give out the workout.
Warm up, stretch, dry land workouts, and finally the actual workout later, they
were dismissed. Jimmy hauled himself out of the water, taking off his swim cap
and goggles as he shook his hair. 5:18, still on time kind of. He went over to
the locker room to dry off quickly, missing a few spots as he took off the
speedo and put on the boxers, shorts, and a shirt. The others were chatting,
laughing and jeering as most showered and usually he would have been with them.
Except that he had someone waiting, someone that was attractive and was his
teacher. He called out his good byes and ran out the door with his bag slung
over his shoulder, semi damp hair sticking up in every direction. It took a
moment for him to find the older man, a breathless grin on his face as he
spotted the dirty blond. "Mr. Winchester!" He called out, going up to the man
with an apologetic smile. "Sorry I kept you waiting."
Dean had decided to stay even past 4; he was thinking maybe he could catch the
youth before he left from practice. He was just locking up his room when he
heard a voice call out his name, a familiar voice, and he turned with a wide
smile on his lips as he slipped his keys into his pocket. "Ah, Mr. Novak!
Perfect timing. I was wondering, did you need a ride home?" He took in the
boy's spiked hair and damp clothes, amusement evident in his eyes. He met the
boy's brilliant blue gaze, tilting his head slightly in question. "You look
like you haven't showered yet. Did you rush over here just to meet me?"
His gaze was cast downwards, heat flaring to his cheeks as he rubbed the back
of his neck. "Practice went out longer than usual and I didn't know if you'd
wait or not so no. But I usually shower at home so it's okay." He cringed at
the lie and how he babbled, congratulating himself with a mental sigh. "But
um.. If you are coming over then, yes please?" Jimmy tried to sooth his
thumping heart, taking gulps of air to not seem like he had practically raced
over here. Which he did, but Dean didn't need to know to add to his
embarrassment. "You are coming over right?" He asked after a moment of thought,
looking up with a hinted cringe of the possible mistake of thought.
He smiled warmly at his student and patted the youth's shoulder, chuckling as
he turned the young man around. "Come on, we've got a tutoring session at your
place," Dean assured, steering the youth gently towards the door that led out
to the teacher's parking lot. He kept his hand lightly on Jimmy's shoulder as
they walked towards his car, his pride and joy: a 1967 Chevy Impala, colored
black and shined to perfection. He pulled his car keys from his pocket as they
ended up on the passenger side, and he quickly unlocked the door and opened it,
gesturing for the student to climb in. "You can toss your stuff in the back if
you'd like."
A smile stretched across his face, the corners of his eyes crinkling slightly
as he bound after his teacher. The sunlight blinded him for a few seconds, his
face scrunched up as his eyes adjusted to the sudden brightness. He was lead
over to a car, dark and sleek, pulling a low whistle from him as he stopped by
the back door. "This is your car? I thought it was someone else's." Honestly it
wasn't that much of a surprise. A guy like Dean with a car like this? Figures.
But he kept it to himself. Jimmy opened the door and put his bag down with a
small huff, closing it and opening the passenger's side to slide in. "Do you
know how to get there?"
"My baby. She was passed down to me from my dad." He chuckled as he climbed
into the driver's side, shutting the door and strapping on his seat belt. "Your
address actually isn't too far from my place. But just in case, you can direct
me." Dean winked over at the student as he climbed in, a throaty chuckle
slipping between his lips. He inserted the keys into the ignition and started
up the car, smirking as he pressed on the gas pedal slightly even though it was
in park, making the engine purr loudly. He glanced over at his student, raising
a brow in question. "When I hit the main road to that leads to our
neighborhood, I advise you to hold on tight." As soon as the youth had buckled
in, Dean shifted the car into drive and pulled out of the parking spot, glad
that he was one of the only few cars there. As soon as he'd hit the main road,
he floored it, the engine roaring as the speedometer needle nudged past 40, and
it was still going. There was barely any traffic surprisingly, which made it
easy to dodge the few cars they did see. He had a grin on his face as he drove,
his expression one of pure joy, and for a bit he forgot he wasn't alone in the
car. He automatically slowed when they breached the first few houses, and he
glanced over at Jimmy, chuckling. "Hope I didn't scare ya, kiddo."
What. Before he could do anything, speak or even breathe, they were tearing
down the roads. What the hell? For a minute his mask fell, a glint flickering
behind his eyes as his lips twitched. Then he was back to wide eyes and paled
skin, hands holding onto the sides with white knuckles. So there was more to
this man than the prestigious teacher that had just lectured him on getting
good grades to get into college. A spark of glee shot through him as he saw the
joy on Dean's face out of the corner of his eye. When they slowed down he
released the leather, took a few stammered breaths and turned to stare at Dean.
"That was.. Fast." He said slowly, swallowing once. "And furious." He muttered
under his breath, slapping himself mentally for the lame pun. "I mean, my house
is the grey one over there." Jimmy sat up in his seat and pointed over to a
house.
He laughed at the pun, shaking his head slowly as he grudgingly slowed to 20
miles per hour, the speed limit for the neighborhood. "I'm not Paul Walker, but
I definitely love to drive fast And furious." He snickered lightly, then smiled
over at Jimmy to show he was teasing. He pulled up to the curb in front of the
house the youth had pointed out, taking in how nice it was. Of course, all
houses in this neighborhood looked good on the outside. Usually the inside too.
He put the car in park and killed the engine, leaning over towards Jimmy
slightly to get a better look at the house. "My house is the same color. Almost
looks exactly the same. Except mine's a bit.. thinner looking." He chuckled as
he pulled back and took the keys out of the ignition before climbing out of the
car, gazing at the house as he shut the door. He knew Jimmy had a twin brother-
Castiel was on Dean's cross country team- and he wondered if the other boy was
home. Probably, considering how late into the evening it was getting. "I hope
your parents will be okay with our arrangement, Jimmy. I don't want to
intrude." He frowned, worry flickering across his expression.
An expression similar to a hinted sorrow flashed across his face, covered by a
small smile and a shake of his head. "I don't live with my parents, my brothers
and sister take care of me." He climbed out of the car and shut the door,
swinging his bag over to rummage around for his keys. "Everyone's out though,
so it's okay." Jimmy went over to the front door, unlocked it and pushed the
door open. "If you don't mind, I'm going to take a quick shower so I don't reek
of chlorine. The kitchen's over there if you want to grab something to drink
and the living room's right here." The rooms were pointed out as he toed off
his shoes and walked over to the staircase. "Give me 10 minutes." With a quick
smile, he darted upstairs and made a beeline to his room.
Dean frowned, ready to apologize, but the youth had already ran up to the door
and unlocked it. He followed cautiously, smiling and nodding as Jimmy spoke.
The youth rushed upstairs before Dean could say anything, and he heaved a small
sigh as he toed off his own shoes before heading to the kitchen, turning in a
360 to take in his surroundings. The place was beautiful, as was easily
imagined, and it was a bit before he finally realized he should probably sit
and wait for Jimmy to be done. He could hear the shower running upstairs and he
smiled, chuckling as he sat down at the kitchen table. So Jimmy had other
siblings, not just his twin. Interesting. Dean wondered if he'd seen them at
all school; surely he would've noticed if others with the last name 'Novak'
were in his class.
His bag was dumped in the corner as he shut his door with his foot, letting out
a sigh as he took a moment to stand and scrub a hand over his face. Dean was in
his house. The Dean Winchester. A grin slid across his lips as he went over to
his bathroom. Wait. Jimmy retraced his steps back over to his bed, tilting his
head and sighing at what he found. A blue note and a box, laid neatly at the
edge of his bed. Without giving it a second thought, he scooped the items up
and walked back over to the bathroom, locking it to turn on the water.
A hand slipped against the shower wall, his eyes closed as he breathed deeply.
Inhale.. Exhale.. Inhale... He made a small noise as his eyes snapped open,
hand sliding across to lay his forearm against the cool tiles to support his
weight. Suds dripped down from his hair and into his eyes, reminding him to
shut them again before the shampoo got in. Jimmy eased back up, sticking his
head under the spray to scrub his hair clean from the bubbles. The rest of his
body was cleaned quickly, he had all ready wasted enough time to still be in
here. He cut off the water and pushed aside the curtains, wiping a hand over
his face as he blindly groped for a towel. One leg out of the shower and then
the other, still taking deep breaths through his nose as he toweled himself
dry. He opened the door and went straight to his dresser, pulling on fresh
clothes as he winced when his pants slid into place.
A short moment to recollect himself and he went over to his desk to get his
papers and pencils, double checking for anything else he had missed. When he
found none, he went over and down the stairs, taking his time with an extra
twitch to his step as he went over to the living room. "Sorry you had to wait
again.." Jimmy mumbled, going around the couch to give Dean a tiny frown. He
stopped in front of the table and bent at the waist, shirt riding up as his
sweats sagged low on his hips, revealing a patch of skin as he spread out the
pile of worksheets neatly across the table. "These are my.. Failed
assignments." Slowly, slower than usual at least, he straightened and turned
around to sit down next to his teacher, chewing his lip rather hard as he let
out a shaky breath.
It was a bit before Dean finally heard Jimmy walk downstairs. He frowned; the
footsteps were... Off. As if the youth were walking funny. His suspicion was
confirmed when the young man came into sight. He smiled politely and nodded in
response to Jimmy's apology, then blinked. As the youth bent over the table,
his shirt rode up, and Dean could tell his pants were hanging low. The patch of
skin that was revealed made Dean swallow noticeably, and suddenly he felt like
he shouldn't be there, at all. Temptation riddled his mind and he had to look
away before the youth noticed as he sat down beside the teacher. He looked over
at the assignments laid out before him and nodded. "Okay, pick one of these
assignments and show me each wrong problem. We'll have your grade up to an A
within two weeks if you work hard."
His eyes skimmed the papers, seeing a splatter of red marks decorate the while
wooden surface. A piece of him grumbled and another sighed, his teeth dragging
over his lower lip in contemplation. Jimmy leaned over across Dean's lap, his
knee nudging the other's as he grabbed the farthest piece. The slight shift
sent tremors through his body, his eyes fluttering close for a second as his
breath hitched. "H- here." He stammered, sitting back with a clenched jaw and a
firm grip on the paper. The majority of the sheet was marked red, a small
grimace flashing over his face. "I've read over it a few times and I don't k-
know what's wrong.." A faint pink bled into his cheeks as his breaths turned
shallow. He bit his lip, trying to control his heartbeat that pounded like he
had just finished a swim meet.
His breath caught in his throat when the youth leaned over him, automatically
leaning back even though there wasn't much space. He felt a reaction with his
body that tried to contain, and he hoped he succeeded; he breathed softly in
relief when Jimmy pulled back, and he chuckled softly at the words spoken. He
pointed to the first question missed and read the question out loud: "Which
Roman Emperor was infamous for hating Christians and splitting the Roman empire
into 2 parts?" He slid his finger down the paper to the answer that had been
marked wrong, and he looked over at Jimmy. "You marked Constantine, which was
wrong, of course. Can you tell me why?"
There was a moment of silence, his mind starting to drift away from what he was
asked. His tongue darted out to wet his lips, drawing his eyes back over to
Dean with a ragged breath. "It's wrong becau- ah! Shit." Jimmy squeezed his
eyes shut and braced his arms on the couch, hands digging into the material as
he hunched his shoulders. His face flushed red as he held back another gasp,
squaring his jaw to keep himself quiet. Wait. Did he just moan in front of
Dean? His teacher? Footsteps stomped down the stairway, breaking his train of
thought as he looked over to who it was.
"Jiiiimmyyy, you know it's to- oh." Identical blue eyes stared at him, lips
quirked into a smirk immediately. "You didn't tell me you had a guest over Jim,
who is it?" A scowl was on his face the moment Castiel skipped over to lean in
between him and Dean with a wide grin that crinkled the corners of his
brother's eyes. "Oh! Hey coach, what are you doing here?"
His eyes widened in alarm when Jimmy suddenly seized the armrests, but before
he could say anything, he heard a voice, much like youth next to him but quite
a bit deeper. He blinked when the twin brother's face was suddenly next to his,
and he could immediately feel his cheeks burning, knowing they were a bright
red. "Well, Castiel, I-I was just tutoring your brother here. I'm sure you know
he's failing History." He cleared his throat and scooted down the couch a ways,
feeling quite embarrassed even though he wasn't sure why. It's not like he and
his student had been doing anything.
A look of surprise over took Castiel's expression, he even made a small gasp
and a disappointed frown. He looked at his brother, shaking his head slowly as
they locked eyes, holding the stare for a few moments before it broke. A
chuckle slipped out as he grinned, receiving a darkened look from his twin. "Of
course I know my bother's failing. How could I not?" He drawled, reaching out
to ruffled locks of thick hair to have his hand swatted away. "But Mr.
Winchester, I have a question for you concerning him- do you know why he's
failing?" Castiel looked over with an innocent tilt of his head, rearranging
his arms to fold on top of the couch to rest his head on, his body half bent
behind the furniture. "I mean, Jimmy's smart. Really smart, and as a teacher
I'm sure you know that even if his scores are the opposite."
A brow raised as he took in the way they looked at each other. Something more
was going on here, but Dean couldn't figure out what. His other brow raised now
at Dean's question, and he nodded slowly. "Yes, I know he is very intelligent.
That's why I'm concerned that he is failing. Do tell me the reason, though, I'm
all ears." Green eyes met blue ones, and Dean felt something within him stir
again; he did his best to keep his blush hidden this time, for he knew what it
was: his blood was rushing down south, all because he had looked into those
gorgeous eyes. What the hell was wrong with him? These were his students, for
Christ sake!
There were eyes in him, he could feel it bore into his skin. It was meant to
stop him, he knew that, but all it did was motivate him. "Do you want to tell
Mr. Winchester Jimmy?" Castiel looked over with the same expression, the
question genuine though there was a flicker behind his eyes. His brother
hesitated, looking down and prying his fingers off of the couch to place on top
of his lap. Oh that wouldn't do.
"No? All right then, I'll tell him." He mused, turning back with a sigh. A hand
moved up to allow him to lean against the palm, the other still rested and
hidden from the teacher's view. His thumb rubbed over a smooth surface, toying
over the plastic with a thought before flicking it discreetly. At the same
moment he heard a sharp gasp, could practically feel his brother's uneasiness
in the air. "You see coach, Jimmy's not really failing because he doesn't know
the subject. No, he's failing it on purpose because we agreed on something.
Isn't that right little brother?" His voice never faltered from the even tone,
almost as if he was conversing about the weather. Castiel turned to see his
twin tensed, hands balled into fists where it laid on his lap, arms tensed, and
mouth hung open.
"Y- yees."
A smug look appeared for a second as he shifted his eyes back over to Dean. "Do
you want to know what we agreed on, Mr. Winchester?"
His eyes never left the other's face until he saw movement in the youth's hand
and heard the audible gasp from his brother. Shit. Was that the controller to a
vibrator? That was inside Jimmy? That Castiel controlled? Dean knew then what
he'd gotten himself into, and he gulped, though the idea rather... Well...
They'd be able to see for themselves if they looked down at his lap. "To get me
alone. Here. In your house." Christ, what an idiot he was, to allow himself to
fall into a trap like this. Just the thought of being alone with the two
twins... Fuck, fuck, fuck. He didn't think there was a way of getting out of
this, and he wasn't sure he wanted to get out of it.
A delighted look beamed on his face, a smirk stretching wider as he nodded. "I
knew not all teachers were dumb. You see, that's part of it. I told my little
brother that if he could get you here first then, well, I'd let him get fucked
first. Isn't that right Jim?" Castiel purred, looking over with a devious grin
as he hit the button again, dialing up the setting.
Jimmy let out a throaty moan, slumping forward slightly at the change, gasping
unevenly as a hand shot out to grip his arm. "Yes." He rewarded his twin with a
comforting touch to the hand that was grasping him.
"And who did I say you could be fucked by?"
Black blown eyes shifted from him face over to Dean, locking on the man's face.
"Mr. Winche- eahh! Winches.. Terr."
Castiel nodded, looking back at Dean through thick lashes, letting his eyes
rake down Dean's body, down to a bulge in the man's dress pants. "Exactly.
Would you like that coach? Would you like to fuck my baby brother first and
then fuck me?" There wasn't enough time for him to hear what the other would
reply with. Not when he had leaned down to capture his twin's mouth with his,
nipping and tugging at ebony hair. Jimmy moaned and whined, parting pink lips
easily as Castiel swallowed each one of them, darting his tongue out to lick
his way in.
Oh dear sweet Jesus. This was... this was beyond any fantasy he'd had before.
This was the king of all sexual fantasies. Seriously, who wouldn't wanna fuck
twin brothers? He watched with eyes dilated with instant lust as the two kissed
right front of him, his hand sliding over to palm himself through his pants.
Hell, he was already hard as fuck. His voice was incredibly husky when he
spoke. "You have no fucking idea." And with that, he lunged forward on the
couch to grab Castiel's shirt, making him wrench away from his brother. If
there were any sounds of protest, he didn't hear it, as he now claimed the
boy's lips with his own. The youths wanted to play? Fine. He would show them
exactly what it was to get into it with an experienced adult.
The two protested in unison, Jimmy with a pitiful whine and Castiel with a
sharp grunt that was silenced immediately. His eyes slid shut as he found
himself kissing a different set of lips, soft yet firm, pressing against his
with determination. Castiel untangled his fingers from his brother's hair,
moving it to snake up Dean's neck with a long moan. There were soft noises next
to him, ones that he knew too well that sent a wave of arousal through him. He
flicked the dial up another notch in a silent apology of the shortened
attention, knowing he was forgiven with a low keening noise.
Watching his brother make out with his teacher definitely was not fair. But any
sort of complaints he had died down when the vibrations in him quickened.
"Fuck." Jimmy ducked his head, digging his nails into the couch again as he
strained his neck. It felt so good, the constant vibrations hitting directly on
his sweet spot that sent hot sparks through him. "Ca- aaaaaaass." He whimpered,
taking a shallow breath as he cracked an eye open to watch the other two.
Damn, the boy could kiss. He groaned softly against the youth's lips before
pulling back with a slight pant, taking in Castiel's expression before shifting
his attention to the other brother. A smirk flickered across his lips as he
carefully moved forward to press them against Jimmy's, his tongue tracing the
bottom one before he shoved it into the other's mouth, groaning softly as he
tasted the youth. God, he'd never tasted anything as amazing as these two, and
he was clearly about to get super lucky with both of them. He lifted his hand
to cup the youth's cheek, his fingers slightly sprawled out over the skin. He
couldn't think past the raging boner in his pants and the explosive taste that
was the inside of Jimmy's mouth. All he knew was that he wanted the twins, and
he wanted them now.
His lips eased open without hesitation, eyes already half lidded as he moaned
into the lips that pressed against his. It was different, the way their tongues
tangled, hot and spit slick, almost similar to the way he kissed. He could tell
it wasn't Cas just by the way the man roamed, a hand caressing his cheek while
his brother preferred to tangle fingers into his hair and tug. Jimmy allowed
himself to be draped by a larger body, inching back towards the couch arm until
he was pressed against it.
It was Castiel's turn to watch now, eyes lust blown as he licked his lips
slowly, memorizing the way Dean had kissed him. How sweet and new it was. He
took off his shirt and pants, leaving his boxers on as he threw it over on the
ground somewhere. "He has a vibrator in him, been all loose and stretched since
he got home. You can fuck him right now if you want Dean." Castiel purred,
voice dropping to a gravelly timbre as he leaned over to mouth at the man's
earlobe.
He had backed Jimmy easily into the arm of the couch, his free hand moving to
rest on the youth's crotch, his palm pressing lightly at first as he continued
kissing the boy. But when heard Castiel's words and - Jesus - the youth's lips
on his ear, his palming roughened, and a groan sounded in his throat as he
kissed Jimmy. Finally he broke away, panting as he locked eyes with Jimmy. He
shifted backwards, the hand that had been palming the boy lifting to run
through Castiel's hair, and still his eyes didn't leave the other's. "I want
you naked and on your hands and knees, Jimmy," He growled in his lust-husked
tone before he turned his head to claim the less shy boy's lips once more,
kissing him exactly the way he'd just kissed Jimmy. He hadn't noticed yet that
Cas had stripped, but boy, was he in for a surprise.
His head tilted back as a breathy whimper curled under his tongue, caught in
his throat as he jolted at the sudden touch. Everything felt so damn good, the
pleasure doubled by the vibrator and just the simple fact that this is Dean.
Jimmy snapped his eyes open at the loss of touch, mouth still parted as he
whimpered. Scratch that, as he swallowed thickly with a soft moan, nose flaring
as he bobbed his head immediately. The clothes were discarded in record time,
all flung to the opposite side of the room as he scrambled to do as he was
told. He turned around to kneel down with his hands planted below him, legs
spread as much as they could to present himself to the other two.
A shiver ran down his spine at the way Dean spoke, drawing an approving growl
from his chest as he complied to the kiss. Wet and hot, almost similar to
Jimmy's and opposed to his skill based tactics. Castiel ran a hand through
cropped hair, tugging at the bottom as he snaked his tongue up to the roof of
Dean's mouth. He let his tongue trail slowly across the surface, moaning
without shame as he tilted his head to deepen the kiss.
He held the kiss he had going with Cas- it was too fucking hot to break just
yet- but he peeked open an eye to glance at Jimmy out of the corner of it. He
almost came right then and there. The sight before him was absolutely beautiful
and worthy of a porn video, and fleetingly he wondered if there were any
cameras set up somewhere. But he didn't give it another as he let his eye fall
shut once more, moaning softly into Castiel's mouth. The way the youth's tongue
felt was mind blowing, and he couldn't help but give the boy's hair a small
tug, a growl sounding in his throat. When he was finally able to pull away from
the kiss, he smirked, letting his tongue swipe across his lips as he stood and
slowly began unbuttoning his shirt. "I bet you wanna watch me fuck your
brother, don't you, Cas? You wanna watch me pound into him, over and over, so
that you can see what's in store for you." He was extra slow with each button,
his eyes never leaving the youth's face.
Oh this man was good. Very good. His eyes slid open and watched the man lick
his lips, running over the full flesh of the lower lip. "Oh, I have a pretty
good idea what to be expecting Dean. But Jimmy's first, he's been a good baby
brother and deserves to be the main spot of attention." Castiel drawled, eyes
glued to each button that was popped at an unnecessary slowness. "You can fuck
him, and I'll watch. Of course I'd watch." His hands shoved down his boxers,
the fabric pooling around his ankles as he stepped out of them. He walked
around the couch slowly, fingers trailing along the top of the furniture as he
adverted his gaze to look over his twin. "With Jimmy sucking my cock at the
same time." A wolfish grin spread across his face, feet stopping directly in
front of his brother. His heated member hung proud and heavy, swollen crown
already pearling precome. "You know what so good about my brother? He has this
whole shy and bashful manner to him, all blushes and nervous fidgets. But
that's not really you isn't it baby boy?" Castiel combed his fingers through
Jimmy's hair, bringing his brother closer to his waiting cock. "You're always
thinking dirty things, wanting to get fucked all the time and be a good little
cocksucker. Always do what you're told, so responsive to everything."
His arms trembled at the words, eyes flickering down to hone in on his
brother's member, inching forward to nuzzle against the base. Without being
told he flicked his tongue out, licking a long stripe up to the tip and swirled
his tongue around, tasting and savoring the other. Jimmy parted his lips and
sank down all the way, not even gagging when the back of his throat was nudged.
"Oh fuck, you're so good at this." He heard, moaning his opinion in response as
he began to bob his head, hollowing his cheeks as much as he could.
There was no way Dean could take his clothes off slowly, not with the show he
was getting. Before he knew it, he'd stripped himself of every stitch of
clothing and he now positioned himself behind Jimmy, sitting just between his
legs, nudging them apart a bit. He leaned down to whisper into the youth's ear:
"You are a good listener. Good. Keep it up and you'll be getting an A in no
time." Dean whispered as he ran his fingers up the younger male's spine. He
pulled back to take a look at the rear, grinning when he saw the vibrator. He
removed it slowly, very slow so that Jimmy would feel it before he tossed the
device behind him and lined his rock hard cock up with the now wide open
entrance. His eyes locked with Castiel's across from his as he slowly slid
himself inside Jimmy, only a thin line of green showing with how dilated his
eyes were. Once he was sure Cas had gotten a good show out of it, he leaned
over the youth he was inside to claim the other's brother's lips in a rough
kiss, his hands gripping Jimmy's hips as, without warning, he began to snap
forward in a quick pace, so that every time he thrust in, the youth's head
bobbed on his brother's cock.
Overwhelming, it was utterly, perfectly overwhelming. A high moan came out of
his as he felt the vibrator inch out, scraping over the bundle of nerves that
shook him down to the core. He didn't have time to whine when he clenched down
on empty space. Not when something bigger and hotter was slipping inside of him
with no resistance. His words were muffled as he keened, screamed when he was
filled, Dean's cock stretching him to the fullest. He didn't know if he should
shove back or go forward, both holes filled as he was rocked and pounded on to
create a synchronized rhythm. Fingers bit into cushions, knuckles pale white as
he sucked his brother with more vigor, spurred by the thrusts he was receiving
from Dean.
Everything was taken in- the sight of the Dean's cock nudging its way in, the
wanton face of his brother sucking his cock like a whore, everything. When Dean
had leaned in, he followed, crushing his lips against the other's. He groaned
at the immediate urgency, the slight bump of teeth, and the fight for
dominance. Jimmy sucked harder, dragging a throaty moan out of him as he
snapped his hips forward, knowing his brother could take it all. His hand
rested on the back of his twin's head, keeping him in place as they all moved
together, pleasure coursing through his veins like wildfire.
The moment of clarity that was bound to come finally struck, the thought 'I
shouldn't be doing this to two teenagers, fuck, I'm in so much trouble' running
through his mind. He shut it down immediately, losing himself in the twins, in
Jimmy's - still - tight, hot, deliciously wet hole, in Cas' equally hot and
delicious mouth. The youth was definitely the more dominate of the two
brothers, but Dean knew he trumped both of them when it came to kissing. He
quickly took over the kiss, pushing back as he shoved his tongue into Castiel's
mouth, loving the taste that was so like Jimmy's and yet was Cas' own. These
two were bloody amazing, and a piece of mind couldn't believe how lucky he'd
gotten. His pounding only got rougher and rougher, his sack slapping against
that cute little ass with each thrust. Dean lifted one hand to slip around the
back of Cas' neck, holding the youth there as they kissed.
Tears were starting to well at the corners of his eyes, his breathing shallow
and ragged. Out of all the things that he had done, this was by far the best-
everything about it was. Jimmy let lose a continues string of mewls and keening
sounds, knowing that each noise he made was sent straight down his brother's
cock. With each thrust, the quickening pace of being fucked, he squeezed a
little tighter, wanting to feel hot come pour into him.
It was his pride that got in the way, the usual mind set that he was the one
that dominated. At first he fought back, tongues clashing viciously to see who
the victor was, but he slowly gave in. He had experience, a lot with what he
had done with his brother but for once he was stumped. His advances became more
subtle, letting Dean do what he wanted as he just followed. Castiel curled his
hand tighter in his twin's hair, knowing that if this kept up, he'll be coming
soon, really soon.
Already he was close, so close, his cock throbbing within Jimmy. God, the
younger male felt so good around Dean, it was amazing he hadn't come already.
But with the way the youth was clamping down around him, he knew he wouldn't be
able to last much longer. And with the pornographic kiss between him and Cas
still going on... This had to be the best day of his life. No, this /was/ the
best day of his life, and he didn't want it to end, at all. His fingers slid up
into soft, dark hair as he twisted his tongue with Cas', almost as if the two
were dancing in the younger's mouth. He wondered how much longer the twins
would last, knowing it couldn't be long now; the boys had to be as close as he
was at this point.
All it took was an expert flick of the tongue around the head of his aching
cock and he was swearing every single curse word he knew in his mind. His hand
was fisted in thick locks, his hips a fraction away from pounding into his
brother's glorious throat with a litany of moans and soft growls. It took the
feeling of a hand twisting in his hair, sending small spikes of pleasure down
to his throbbing member, and another swipe over his slit and he was seeing
stars. Castiel shut his eyes and gaped, paused his movements as he was thrown
over the edge with a hard suck from Jimmy. His body convulsed and tensed, come
pouring out to be sucked by his twin.
Just, a little bit more and- Hot liquid shot down his throat, his eyes widening
as he swallowed it all down eagerly as he gasped around Castiel's pulsating
member. His body locked up all at once, his ass squeezing tight around Dean as
he felt his body shake. White painted a part of his stomach and the couch below
him, his arms nearly collapsing as Dean continued to pound into him.
The moment he felt Jimmy clamp down around him, he released Castiel's mouth
with a loud groan, though he didn't let go of the youth's hair. Within moments,
his seed was spilling into the twin beneath him, and he had his lips latched
onto the neck of -he assumed- the older brother, sucking roughly as he emptied
his load into Jimmy. He sort of slumped against the kid's backside even as he
worked on the hickey that would mark Cas as his, a growl sounding in his
throat. When he finally let go of the older brother, he panted softly as he
leaned down to press kisses along Jimmy's spine, his words coming out in
whispers. "So perfect.. such a good little student.."
A side ways grin spread across his lips as he heard that noise, a throaty growl
that made him curl his toes. The hickey wasn't unnoticed as a sense of delight
ran through him at the marking. He let out a heavy breath as he stroked his
twin's face, pulling out as his cock softened. "Come here Jim." Castiel knelt
down to be leveled with his brother and kept his hand cradled on the side of
the other's face. Without a word he pressed forward, licking at the remnants of
himself on plush lips that opened immediately. It was slow and languid, both
riding out the end of their release. For a second they forgot Dean was here,
too caught up in the lazy exploring of each other's mouths. It wasn't until
Jimmy dipped his back a little did Castiel part, looking over his brother's
shoulder at Dean. "So what do you think teach? Can Jimmy pass your class?"
Dean pulled back just in time to watch the two brothers kiss like their lives
depended on it, and boy, if that didn't strike up arousal. He slowly pulled out
of Jimmy, his eyes still dilated with lust as he watched, his tongue flicking
across his lips. When they parted, he could see just how red Castiel's lips
were from kissing his brother so hard, but he didn't dwell on the sight; his
eyes found the other's and he gave one of his usual smirks. "Only if he
promises to stop failing on purpose. If you wanted me over, all you had to do
was ask. And now, I believe its someone's else turn, isn't it?" He grinned as
he leaned over the younger brother carefully to capture Castiel's lips in a
kiss, the meaning of his words lingering behind it. He could feel the way his
still hard cock pressed into the cleft of Jimmy's ass, and god, the youth felt
so good, he couldn't help but wonder how the other would feel. The thought
immediately struck heat down into his groin, and he groaned against those soft,
plump lips, loving the taste of them quite immensely.
With one small gesture, he smiled into the kiss, soft compared to what he had
just done. Castiel withdrew to give a kitten lick across the seam of Dean's
lips, smirking as he leaned back. "You know what to do little brother." There
was a nod from his brother as the two moved, Castiel walking over to stand in
front of Dean as Jimmy stepped aside as he sought out the discarded vibrator.
"As much as I want you to fuck me right now, I haven't had the time to prep
myself." He placed his hands on Dean's shoulders, pushing the man up to flatten
his back against the couch. "And while Jimmy's going to plug himself with his
vibrator, what do you say to me sucking you cock hmm?" His hand skimmed down
Dean's chest lightly, leaned in to mouth up the man's neck to whisper in the
other's ear.
He purred softly under Cas' little lick, but was surprised when Jimmy moved
away and suddenly Cas was in front of him, Dean's back pressed against the
couch. His eyes dilated to their fullest once more at the older sibling's
words, but before he could respond, he cut himself off with a light groan as
the youth lipped at his earlobe. He could only imagine what Jimmy looked like
as he was pleasured with the vibrator, and that image combined with the one of
Cas sucking him off made his cock twitch. He nodded quickly, his breathless
words tumbling out into the air. "Yes, god yes, please." He rutted his hips
against Cas' once to show just how much he wanted it, so bad that he would have
shoved the kid down on his knees right then and there if his thoughtfulness
hadn't taken over.
A soft chuckle slipped from him as he felt Dean buck against him, his eyes
narrowing to slits. "How polite, you asked please." He murmured, placing an
open mouthed kiss underneath the other's jawbone. The man's scent was simply
mouthwatering. Whatever cologne Dean used mixed with his natural scent and the
faint smell of sweat made him lick his lips. "You don't have to be so courteous
with us Dean." Castiel hovered over the spot he had nipped at, licking over it
once before trailing down the neck. Each kiss and lick made its way down lower,
traveling from the collar bone down to the man's navel and eventually, to the
base of heated skin. "You ready baby boy?" His tongue darted out lavish the
length before him, his lips wrapping around the head as he swirled his tongue
around the crown. He didn't need to look back at his twin, already knowing that
his brother had heard him. In one fluid motion his jaws parted and he took Dean
down in one bob of his head. His eyes fluttered shut as he swallowed around the
thick cock, thinking of how it would feel in him. He sucked up, letting his
teeth graze the vein that was pressed against his tongue as he hollowed his
cheeks.
Where the damn thing was, he didn't know. He only knew that he needed to find
it quick before Castiel started without him. With a few seconds of shuffling,
the pink vibrator was spotted and grabbed. Jimmy looked over just in time to
see his brother on his knees, sucking Dean with a look that made his softened
cock twitch. He slipped the vibrator back in, wincing slightly as it was pushed
against his prostate. But he didn't have time to play with it, not now at
least. Jimmy went over to kneel behind his brother, palming each cheek before
he spread the other's ass. He leaned forward and licked over the hole, feeling
it flutter under his tongue. Normally he would drag it out longer, prod and rim
his brother slowly until he was told to 'just fuck him' already. But instead he
sucked on two fingers, slicking them before he pressed against Castiel's hole,
easing them in up to both knuckles.
Dean's eyes rolled back in his head, each kiss sending a small yet still erotic
tingle of pleasure through him. When he felt that lovely pink tongue on his
heated flesh just above his cock, he almost bucked his hips, but he didn't want
to seem like an eager slut; he was about to be blown by a teenager after all. A
sexy, gorgeous teenager with an equally appealing twin brother, but still, both
teenagers. He couldn't help the moan he let out though when those perfect lips
wrapped around his head, and then the gasp when the boy took him in all the way
in one swallow. His hands immediately flew down to the youth's shoulders,
gripping them rather tight as he practically chanted "Fuck, Cas, aah, fuck"
over and over. And then.. oh god, was Jimmy about to fuck his own brother? From
the visual Dean was getting, it sure seemed like it, and this time his moan was
amplified in volume, the teeth grazing the vein in his cock making him shudder.
"C-Cas, fuck.. feels so good.." He managed to groan out, his speech ability
marred by his breathlessness.
Just hearing those two made him hard in a minute. Plus the tight hole he was
fingering and the stretch of the vibrator that plugged Dean's come in him. He
slipped a third finger in along the other two, moving his lips along the flesh
of Castiel's ass to place small kisses and nips. All he could manage was a few
more minutes, enough to loosen his brother but not enough to stretch him
completely. Jimmy scooted closer on his knees, retracting his fingers to lick a
stripe across his palm and slick himself hastily. With one hand at the base of
his cock and the tip pressed and nudging into his twin, he snapped his hips
forward to bottom out in one thrust. "Oh fuck" He groaned, running his hands
along Castiel's sides as he set a slow pace, relishing the feeling of the tight
heat.
Castiel flat out moaned like a bitch in heat when he felt fingers stretch him
open, one by one until a cock was shoved into him. His sucking only grew more
insistent, eyes opening to look up at Dean. It was lewd, the way he sounded
while getting fucked by his own brother and sucking his teacher dick, but so
good. Every thrust was punctuated with a short gasp and swallow around Dean,
his mind hazing into a mess. But he stopped, pulled off of Dean with a wet pop
as he tapped his brother's arm twice.
He could feel the difference in just the couple of nova Cas had given him and
the more jerky head movements that went along with Jimmy's thrusts, but it all
felt so amazing that Dean didn't care about the difference. He moaned with each
bob and groaned when Cas suddenly pulled off.
"I said, that, you would fuck me right?" A grin stretched across his face as
Jimmy slipped out, allowing him to slowly climb on top of Dean to straddle the
man. "And if I come before Jimmy does watching us, then I'll eat your come out
of his ass." Castiel licked his lips slowly, lifting himself up to grind back
against Dean's cock.
As soon as the words were said, Cas was in his lap, grinding against him, and
it was all Dean could do to hold himself together as he seized the youth's
hips, growling as he eagerly returned the grinds. He leaned in close to
Castiel's ear, his voice pitched low and even huskier than before; he knew it
would sound like pure sex. "I hope you know what you're getting yourself into,
boy. What Jimmy just received? It's double when riding me." Dean smirked,
flicking his tongue along the shell of the youth's ear before pulling the lobe
between his teeth; it was his turn again to leave marks, and he intended to
leave plenty of them. His hands slid up the boy's naked torso, their sweat
slippery bodies grinding roughly together as he felt the youth up, growls
punctuating his kisses and nips.
It would be a terrible lie to deny the fact that he shivered at what Dean said.
His teeth dragged along his lower lip as hands and lips roamed the planes of
his body, feeling and tasting every inch of skin. "Oh yeah? Prove it." Castiel
canted his hips up, reached back to line Dean up to his waiting hole. Dean
would be bigger than Jimmy, he knew the man would be when- "Holy shit." He felt
the raw burn as he lowered himself onto Dean's cock, gasping as he went down to
the hilt.
After he had pulled out, he knew it wouldn't be long until the other two would
start fucking. Waiting wasn't in Castiel's nature. He got up and went over to
sit on the couch, swiping the control as he sat down to watch his brother and
teacher grind against each other. The switched was flipped and the buzzing came
alive, vibrating right against the bundle of nerves that shot pleasure through
his veins instantly. Jimmy settled back against the arm if the couch and spread
his legs. He couldn't touch the vibrator, but he could touch himself. His hand
wrapped around his member, automatically pumping as he saw Castiel sink down on
Dean's cock. A moan slipped out as he watched, eyes greedily drinking in the
sight.
He still had his lips on one side of Castiel's jaw, but when he felt the youth
slide down on him, he released a wanton groan against slick, heated skin, the
way Cas felt around him absolutely blowing his mind. Even with the fact that he
had already been loosened up somewhat by his brother, Cas was still amazingly
tight, and Christ, he felt so good that Dean wanted to switch their positions
so that he could pound into the youth like there was no tomorrow. He could the
other brother across from them moaning as he pleasured himself, and he couldn't
help but let that be a motivator as he immediately began moving his hips
upwards, his growl more guttural as he nipped at Castiel's jaw, hands
continuing to skim over the youth's body.
Being on top was something he had perfected, something he had trained himself
to become a master at just like how he had trained Jimmy to be the perfect
cockslut. The person underneath him wouldn't move, not when he was fucking
himself down on a cock with his hands planted on the other's chest. But Dean
didn't play by that apparently. A surprised gasp was sucked in sharply when he
felt the cock ride in deeper, shuttering as he paused for a split second. His
brows furrowed as he tried to focus on taking control, to make it so that Dean
wouldn't be able to move but it was getting extremely hard to not just submit
and let him be fucked over and over from the top. Castiel slid his eyes shut,
hating the amount of pleasure he felt from riding the man when he wasn't the
only one taking the reins.
Oh. That was rare. His hand never stopped it's course as he watched the other
two and he couldn't help but feel a thrill run through him at the short stop
his brother had come to when Dean had moved. The only time Castiel had ever
stopped moving when on top was when the person below him was too good for him
to control. Jimmy licked his lips slowly as he let that play in his mind, as he
remembered what it was like to be fucked by the older man and to have his come
plugged within him. Shit.. He clenched his jaws at the slip of his hand, trying
his best to keep the orgasm at bay as he pumped a little bit slower, wanting to
outlast his brother.
God, Cas felt and looked so good on top of him... Dean couldn't resist
thrusting sharply, repeatedly into the younger boy, his teeth gritted and his
hands keeping a tight grip on the youth's hips. He could feel Cas trying to
take control, to keep his coach still beneath him; Dean wasn't gonna have any
of that. The older man could hear the younger brother across from them, he
could hear the sound of skin moving against skin, making a wet sound that sent
a stab of heat down into his groin, and in reaction, he groaned loudly, his
eyes squeezing shut as his thrusts hardened and quickened.
There wasn't even a second for him to even think that he had quelled the man
below him. Not when his eyes snapped back open and a choked noise came from his
open mouth. "Holy shit." Castiel scrabbled to keep himself latched to Dean with
his nails digging into the man's chest as his breathing came in ragged gasps.
Not only had the pace quickened, but Dean had also somehow found his prostate
and was hitting it in perfect aim repeatedly. Tears pricked at his eyes from
the overwhelming growth of pleasure, and he didn't even have the chance to try
and stop the thrusts before he shouted. The sheer force of his orgasm made him
double over, his body shuttering as come coated his lower abdomen. The room
spun for a few seconds as the ringing in his ears hammered with the pounding of
his heart in unison, droning out anything else.
Just as he was about to shift his position, the need to disappeared when he
heard that sound from Castiel. One that he knew too well and usually ended with
his face shoved into his brother's crotch as come poured down his throat. Jimmy
stared wide eyed at the pair, disbelieving at how fast it had taken for his
twin to orgasm. His hand moved even faster, gyrating at the head as he focused
on just the pure sense of pleasure that ran through his veins. Another three
seconds and he was pitching in his own broken moan, head tilted back with his
lips parted and eyes half closed.
He didn't have time to even think when he heard Cas yell and he felt warm
liquid spew onto his abdomen, undoubtedly painting the youth's torso as well.
Deab couldn't believe he'd made Castiel cum so fast, and it was clear by the
sounds Jimmy was making that he'd hit his peak too. It was all too much for
him, and he couldn't hold back. His fingers dug into the boy's hips as he
hollered, his thrusts ceasing and his body becoming rigid as he spewed his seed
into the young teenager on top of him.
When he'd finally been emptied of his load, he loosened his grip on Cas, gasps
escaping him as he tried to catch his breath. He stared up at the younger male,
his pupils still blown wide with the intense desire he held for the two boys,
and he spoke between breaths, "You.. are too.. fucking sexy. Fuck."
Castiel blinked a few times to clear out his head with barely enough strength
to keep himself up on shaky arms. "You're... not too bad.. yourself." He weakly
chuckled back, avoiding the thought of how fast he had came. Regardless of the
time, that had to be one of the best orgasms he had ever had. The wanting to
lay down and pass out was strong, but somewhere in his fogged mind, he
remembered the bet he had dared to place before his release. "So.. Looks like I
lost huh?" He managed to grin and turn back to look at his brother who was as
equally worn out as he was. "Turn around Jim."
Jimmy blinked blearily back at his brother, taking a moment to ride out the
pleasure that was quickly depleting. Soon he was shuffling around to drape the
top half himself over the couch arm and present his ass towards the other two.
The vibrator was still on and it was getting to the point of it being
irritating, but he didn't dare to remove it without his twin's say so.
"Good boy." He purred, untangling himself from Dean and to lean over. His
brother's hole was puffed around the purple end of the vibrator, and he took
his time in running a thumb over it just to see Jimmy flinch a little. Slowly,
he pulled it out only to drop it onto the floor as he dived in before any of
the substance could leak out. Castiel couldn't help but groan as he lapped the
come out of his brother's ass, using his hands to spread the cheeks more for
better access.
 
With a soft groan Dean pulled himself up to have a better view of the two
Novaks, groaning once more when he saw how into it Castiel was. Words failed
him as he simply reached out to run a hand over the swell of the older brunet's
ass.
Castiel pushed back when he felt a hand on him, moaned as he pushed his tongue
in deeper. Eventually he leaned back, satisfied as he licked his lips before he
was pulled back onto Dean's lap. Their lips met and he purred into the kiss,
lazily licking and mixing their tastes together. He pulled back, breaking the
kiss to beckon his twin over to curl up on him as he shifted around to lay down
in a more comfortable position.
Words couldn't even describe what had just happened. To him, the teacher of one
of these boys and the coach of the other. Still, his mind was too fried to even
worry about the best sex he just had in his life. Dean gave a content sigh as
he watched Jimmy and Castiel cuddle up on him and ran a hand through the
eldest's hair.
“Can you tutor Jim again sometime soon?”
“I can give you two a ride home tomorrow. Deal?”
“Deal.”
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