Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/11811933.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Castiel/Sam_Winchester
  Character:
      Castiel, Sam_Winchester
  Additional Tags:
      Alternate_Universe_-_High_School, Teacher-Student_Relationship, Student
      Castiel, High_School_Student_Castiel, Alternate_Universe_-_Student/
      Teacher, Teacher_Sam, Teasing, Begging, Crying_Castiel, Orgasm_Control,
      Orgasm_Delay/Denial, Cock_Rings, Anal_Sex, Anal_Fingering, Rimming, Top
      Sam, Bottom_Castiel, Shota_Castiel, Underage_Castiel, Dubcon_if_you
      squint, One_Shot
  Series:
      Part 1 of SPN_Kink_Meme
  Collections:
      Supernatural_Kink_Meme
  Stats:
      Published: 2017-08-15 Words: 2652
****** Private Lessons With Mr. Winchester ******
by darkstiel_(momstiel)
Summary
     Castiel was usually a good boy… keyword, "usually".
     He needs private lessons and Sam knows how to get results.
Notes
     Based off of this prompt :
     http://spnkink-meme.livejournal.com/
     126067.html?thread=44028531#t44028531
     !! Warning !!
     This fic features a fourteen year old student Castiel having sexy
     times with his older teacher Sam
     Please read the tags first. :)
Castiel was usually a good boy… keyword,  usually . Ever since he started
puberty, he spent more time than he wanted to admit thinking about sex. It was
just around the time where he started to discover the world of pleasure (and
his brother, Gabriel’s, porn stash). Cas wasn’t happy with himself, wanting to
remain in the mindset of an innocent child. However, that wasn’t the case; his
little buddy had different plans… time consuming plans. Most of the time the
young Novak preferred to spend his evenings attending to his erections than to
those pesky Algebra problems. Yet, alas, with such little time or interest
dedicated to school work, Cas’s life was altering.
 
It wasn’t long before his grades fell, and his teacher, Mr. Winchester, was
quick to notice. Not being one to tolerate failure in his classroom, he decided
to get in contact with his student’s guardian to suggest tutoring.  
 
Thus it was set up, every other day he was due to spend an hour after school
let out until his grades improved. Castiel didn’t overly fancy this
arrangement, but he was in no place to argue. So here he stood at the door of
Sam Winchester’s classroom. It felt weird walking into the vacant room, Cas
being so used to the area being full of chattering ninth graders.

“Castiel, step in.” Mr. Winchester insisted, tapping a pen against the open
lesson plans on his desk. He pushed glasses up the bridge of his nose, looking
over the approaching scholar who was heeding his words. “Feel free to take a
seat up near the front.”
 
Obediently, Cas went up to the front and took a seat at a desk directly in
front of his teacher’s. There was a few moments of silence as Sam scanned over
a mess of scattered notes. However, it was abruptly cut short by the man
slamming aside all of the papers. Castiel jumped a tiny bit by the sudden
action, but didn’t question his instructor.
 
“You’re fourteen, correct?” Sam asked, hazel eyes locking onto wide blue ones.
 
“Uh, yes.” Castiel scrambled to answer, wondering how Mr. Winchester’s question
was relevant. A tiny, interested grin appeared on the tall man’s lips.
 
“Okay.” Mr. Winchester replied, standing up and walking out from behind his
desk. He walked around, going over to the front of Cas’s. “So, Cas, tell me
what’s the deal with you lately?”
 
Castiel opened his mouth as if he was going to respond but quickly shut it,
blush rising to his cheeks. He didn’t want to admit that instead of dedicating
one hundred percent of his evening studying for the midterm, he spent time
researching BDSM online. “Uh, distractions I guess, Mr. Winchester.”
 
“Distractions?” Sam asked, clearly unsurprised by his pupil’s answer. He pulled
up a chair and sat down right by Castiel. “What kind of distractions?” The
teacher prompted, a tiny grin on his lips.
 
Instantly the fourteen year old scratched his neck awkwardly, attempting to
form some kind of lie. “Like TV and stuff. The normal.” Castiel played his
teacher’s inquiry off, not wanting to get the truth. Mr. Winchester seemed to
be a calm and understanding person, but he knew that there was certain things
that he just had to keep to himself.
 
“Castiel…” Mr. Winchester dragged out the boy’s name in a deep way that caused
his spine to tingle. “I think we both know that’s not the truth,” Sam accused
calmly, crossing his arms. “Tell me the truth, I won’t be mad. I just want to
help you.”
 
Averting his eyes from the prompting professor, Cas stared down at his lap. “I
already told you…. TV.” He insisted slowly, not sure what else he could say.
“And maybe electronics.”
 
Sam narrowed his eyes a tiny bit, little crinkles forming around his hazel
eyes. “I told you to be honest, Castiel.” Even though he remained a calm
demeanour, Cas could tell that Mr. Winchester was getting a little bit more
irritated and pushing. “Is it your family?” Castiel shook his head, seeming a
tiny bit surprised that Mr. Winchester would think the fault would lay in his
household. “As you said earlier, you’re fourteen… I’m only left to assume that
the only thing between you and your schoolwork is your teenage libido.”
 
Instantly Cas became silent, unsure how to respond to his teacher’s correct
allegations. “Uh.” He was dumbfounded, surprised that Mr. Winchester had gone
in for the kill, passing all boundaries.
 
“Don’t lie.” Sam warned, eyes sticking on his student. “Tell me the truth, and
there will be no consequences.” Mr. Winchester claimed, continuing his pursuit
for his student’s honesty. “Is that the reason why your grades are taking the
hit?”
 
“Yeah.” Cas whispered, barely audible. Nevertheless, he could tell that Mr.
Winchester heard his response, a tiny grin on the teacher’s face. He sat still
and silently as the older man leaned in, placing his lips tauntingly close to
his student’s ear.

“We might as well fix that problem then.” Mr. Winchester’s breath tickled
Castiel’s skin and he felt another tingle shoot up his spine. The ninth grader
wasn’t sure what his teacher planned to do, but his palms were starting to
sweat because of the way that his instructor was talking.
 
Without any hesitation, Sam put a hand on top of his student’s crotch.
Instantly blush ran across Castiel’s face as he desperately tried to ignore the
way his cock twitched in interest. “We’ve got to get you to get used to this
little guy being hard while you’re doing homework… there’s only way to do
that.” He paused, noticing the way that the dick responded. “Remove your
pants.”
 
The color red had made itself home on the boy’s cheeks. He knew that the right
thing to do was stop and report his teacher’s perverted methods… but for some
reason, he couldn’t bring himself to run out of the room. Instead, he found
himself being slowly undressed by his professor. By the time that Mr.
Winchester had removed Castiel’s pants, the fourteen year old felt his semi-
erect cock pushing against the soft fabric of his underwear. “You seem eager.”
Sam pointed out, but Cas made no effort to give him a reply.
 
Not being faint-hearted, Sam continued on and discarded the boy’s clothing
until the student was left naked. “Let’s do this.” The teacher suggested, going
over to his desk, pulling out a cock ring, and coming back. He placed the ring
around the base of Castiel’s semi-erect penis. “This will prevent you from
coming prematurely, and it will strengthen your ability to concentrate with an
erection.”
 
Castiel shivered at the feeling of the cold ring, but his cock stirred up in
fascination. He knew what the item was, guilty of watching orgasm controlled
porn before. While he was adjusting to the feeling, he failed to notice Mr.
Winchester heading back to his own quarters until a paper was plopped down on
the desk in front of him. “Sit down, and try to fill this out. I want to see
what you know.”
 
Somewhat surprised and a little disappointed in the lack of attention to his
erection, Castiel slowly sat down. Right now he didn’t want to do his work, he
wanted to relieve himself. Sam watched as the boy began to half-heartedly put
his name at the top of the page.
 
Mr. Winchester watched for a little bit, eyes on his student’s raised prick.
“Focus, Castiel.” He instructed before deciding to raise the heat a little bit.
Going back to the drawers of his desk, he pulled out some lube. It was evident
that Cas was confused on why Sam had such items handy, but he didn’t have time
to think about it until he felt a lubed finger enter his ass.
 
Instantly he grew tense, not used to an intrusion in his hole. For a few
moments he just sat still, lost in the feeling of a finger popping in and out
of him. “Castiel!” Sam reminded and instantly the blue eyed boy picked his
pencil up again and started looking at the first problem.
 
It felt like an eternity to Cas as he finished a problem with a finger
exploring his insides. Sam inserted a second finger causing the boy to gasp in
surprise. Instead of losing himself in the feeling, he continued to work on the
second problem. Reaching up to Castiel’s front side, two fingers still working
in and out of his ass, Sam began to tickle the underside of Cas’s balls. It
took everything the ninth grader had to not moan, but he couldn’t help but
thrust forward at the feeling.
 
“Mr. W-Winchester…” Cas whined as he felt a wet finger explore along the
underside of his erect cock. “Please…” He whimpered. “Can’t I do these problems
l-later?” The boy asked, the simulation too much already. If it wasn’t for the
damn cock ring keeping him from exploding, he knew that he would have already
came. Now, his mind was clouded with lust and want. It was so hard to focus on
the problem he had already re-read three times.
 
“I won’t stop until you finish your set of problems. Don’t rush, they need to
be correct.” Sam responded, putting in another finger! Cas’s knees went to
jelly when he felt three fingers rubbing against his inner walls. It hurt a
little at first, but he was started to get use to the pleasure. “Come on,
Castiel.” Mr. Winchester prompted.
 
Biting his lip, the boy shakily finished the second problem. He even showed his
work on the margin of the page, desperate for his release. It was only ten
problems, but he knew that it could take him up to an hour to finish them. For
a torturously long period, Mr. Winchester was teasing and simulation his hole,
his balls, and his cock. “Eight more problems.” The teacher reminded, glancing
over the boy’s shoulder.
 
“Y-yeah…” Castiel whimpered, eyes widening when he felt hands leave his
desperate lower regions. For a few seconds he was confused as to why Mr.
Winchester stopped, but it all made sense when he noticed that his professor’s
hands had went to his own pants, which he was working his way out of. All Cas
wanted to do was stare as Sam stripped, revealing a huge erection. Mouth
watering a tiny bit, the ninth grader turned back to his paper. He prayed to
god that the second that he finished his problems he’d get fucked out of his
mind and cum in the process. Very slowly and reluctantly, the boy finished his
third algebraic problem.
 
“Stand up.” Mr. Winchester instructed, causing Cas to blink but slowly stand
up. The older man slipped into Castiel’s seat before grabbing his students by
his hips and putting him on his lap. The ninth grader felt his skin burning up,
not use to such of a sensation. He felt the man’s length teasing his hole,
rubbing against his soft flesh.
“Please….” Cas whined, desperate for any kind of attention. He tried to push
back on the teacher’s erect cock but Mr. Winchester didn’t let him. Shaking as
he went onto his fourth problem, Cas kept thrusting his hips forward, cock
hitting the tip of the desk. As he fell back after each thrust, his ass was met
with the warmth of his teacher’s erection. The teasing was dastardly, and he
felt such of a strong urge to release right then and there. “Please!” He cried
out, whining and rubbing into Mr. Winchester.
 
“Get to your sixth problem.” Sam insisted, deciding to tease his whimpering and
writhing student even more. He grabbed his own erection and began to flick it
back and forth, rimming around Castiel’s puckered and clenching hole. Then, he
pulled Cas back more, letting the student sit on his length that was now in
between the boy’s thighs. His cock nestled against his pupil’s hot and
pulsating balls.
Castiel endured this torture, whining and begging for his teacher’s erection in
his ass until he reached and finished the dread sixth problem. His eyes were
hooded a little, not sure if he was able to handle this much longer. “Please!
Fuck me! Let me cum! Please!” The boy glanced down at his own erection,
watching the cock ring. Deciding to be devious, he tried to discreetly reach
down and remove it.
 
However, his approach came to a sudden halt when Sam noticed and pushed
Castiel’s hands away from the young cock. “I won’t fuck you if you remove
that.” He warned, grabbing his own erection and placing it into Cas’s clenching
hole.
 
Instantly the student whined and pushed back, sending the firm length deeper
into his ass. He winced for a second, not used to the feeling. It hurt a little
bit, but with each passing moment the pleasure was gaining more control.
Desperately he began to fuck himself on Sam’s cock, tears rising at his eyes.
He started problem seven with blurred vision, but Mr. Winchester began to wipe
away the tears from his overwhelmed student’s eyes.
 
“I’ll start moving when you finish problem eight.” Mr. Winchester promised,
pleased with all of Castiel’s previous correct problems. The boy definitely
knew his stuff, if he actually took the time to concentrate on them.
 
“O-okay…” Cas whined in response, crying and begging still. He finished the
seventh problem, hard dick still in his ass. Part of Castiel just wanted to
pass out, rip the cock ring off of himself, and just go and sit down on Mr.
Winchester’s dick whether the teacher liked it or not. But Castiel was a good
boy, mostly. A part of him wanted to please the man, showing him that he was a
golden student… and that he wasn’t just another delinquent!
 
As he finished the eighth problem, almost on cue, Mr. Winchester’s hips began
to snap forward into him. Castiel let out a huge moan, throwing his head back.
His cock pulsated, wanting to release but that damn ring still preventing him
from letting him do what he wanted to do. “Please!” Castiel cried out like a
broken record, the thick dick buried deep into his gaping hole. “Fill me up!
Fill me up! Let me cum!”
 
“Get to problem ten.” Mr. Winchester commanded firmly, seeming to only
acknowledge his student when Cas finishes a problem. Sam felt his own face
flush, pushing into the now-open hole. He had always imagined fucking such of a
beautiful young boy, and he couldn’t believe that he finally had one… begging
and crying for him to spill all over inside of him.
Completely overstimulated, Castiel raced in a focused manner to finish the next
problem. Once he got to problem ten, his hand was shaking terribly but he was
insistent on finishing. Just as he began to write down the solution, he moaned
loudly when he felt Mr. Winchester hit his prostate. The hits kept on coming
until he felt something hot and sticky filling up his hole. As he finished the
very last number, done with the exercise, he felt warm hands working the cock
ring off.
 
All it took was for Mr. Winchester to lazily hit his prostate one more time and
he came all over himself and the teacher’s hand. His head fell back onto the
man’s chest behind him and he just inhaled and exhaled, taking in the best
orgasm he had ever had. Completely spent, he just rested against his teacher,
softening dick below him. Sam looked over his student’s paper, pleased to see
that despite the distractions, the boy had gotten everything right. “Good job,
Cas… you got an A+. I think your distractions should no longer be an issue..”
 
Sleepily Cas glanced up at his teacher, biting his lip. “Can I still come to
tutoring?” He asked.
 
With a tiny grin on his lips, Sam nodded. “I think that can be arranged.”
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