Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/2166678.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Castiel/Dean_Winchester
  Character:
      Castiel, Dean_Winchester
  Additional Tags:
      Alternative_Universe_-_High_School, Nervous!Cas, Inexperienced!Cas,
      Experienced!Dean, PWP, Blow_Jobs, First_Time, Anal_Sex, Anal_Fingering
  Series:
      Part 1 of College_Bound
  Stats:
      Published: 2014-08-19 Words: 2957
****** College Bound Boyfriends and their Downfalls ******
by phoenixloverful
Summary
     Near the end of Dean's senior year, and Cas' junior year, Cas is
     eager to finally have sex with his boyfriend. But after little
     incident, Dean is hesitant to move forward.
Notes
     So the title really has nothing to do the content, I'm just really
     bad at titles. Cas is seventeen, Dean is eighteen. Kudos, comments,
     anything is very much appreciated.
Dean Winchester was the "it" boy of Lawrence High School. He had the looks, he
had the athletic prowess, he had a genius little brother he adored. So how did
an all-American, good boy like Dean, end up with the nerd of the school? The
MALE, nerd of the school.
Dean had asked Castiel Novak out on the first day of his senior year, Cas'
junior year, and went through two weeks of whispered no's and panicked glances
around them from Cas until the younger boy finally said yes. The entire day,
Dean waited for Cas outside of all of his classes and insisted on carrying his
books through the hallways. Being a senior, Dean had a free period at the end
of every Friday, so he waited in his car for Cas to get out of class for the
weekend.
Their first date consisted of a fifties style diner and a black and white
movie, also from the fifties. Each Friday, Dean waited for Cas to come from
classes, just so he could take him on a themed date. They worked their way
through the decades (with a very handsy memory of the eighties), then they
turned to color-themed dates (white was a blast)
Now, nearing the end of school, Cas was faced with the knowledge that soon,
Dean would be off to college, with new friends, new parties, new potential
theme dates to plan, and Cas was bummed out. This weekend, Dean's family was
going out of town to visit some cousins on Mary's side, but since Dean had to
work, he couldn't go. He had the whole house to himself and had invited Cas
over to spend the night.
While they had been dating most of the year, Dean and Cas had barely progressed
past handjobs in the back seat of Dean's car. Except the last time they were
alone together, they had been very close to actually having sex. Cas' brothers
were away with work or whatever they did, and Dean had laid Cas out and given
him a very messy blowjob, but as soon as his finger traveled lower, Cas freaked
out and they ended up watching a movie, fully clothed, instead. Throughout the
entire first half of the movie, Cas could see Dean's cock straining against his
jeans, his hand balled in a fist by his side, and Cas just felt horrible. Dean
never said anything about it, and for that Cas was grateful, but it didn't
change the fact that Cas teased the hell out of Dean, only to send him home
with a chaste kiss on the cheek and a killer case of blue balls.
But this weekend wasn't going to end like that. Cas had experimented with
fingering himself, found that he enjoyed it, and was ready and willing to show
Dean that he had a perfectly good boyfriend waiting for him at home if he ever
needed anything.
Friday night, Cas rode home with Dean, as usual. The car purred under them, the
music blared around them. The silence between them was comfortable and familiar
as Dean drove Cas to his own house for a change. Cas' duffel bag was already
stored away in the trunk; he had put it there that morning when Dean picked him
up for school. Dean was at the door, fighting with the old lock system so they
could get into the house. Cas came up behind him and wrapped his arms around
the taller boy's waist, leaning in to press a kiss to his neck. He felt rather
than heard Dean chuckle as he turned the lock in the tumbler and the door fell
open.
Dean led the two of them to his bedroom so Cas could put his bag away, but that
wasn't all Cas planned to do. After he tucked his bag safely in the closet, Cas
stretched out on the bed while Dean ran to the bathroom. He could hear the
water running in the bathroom, and the telltale snick of the toothpaste bottle
opening. Cas grinned to himself as he imagined Dean primping himself only for
Cas. His eyes slid shut when the water turned off, his arms laid out behind his
head so that his head was pillowed by hands.
The smell of the mint toothpaste and just a touch of cologne followed Dean in
from the bathroom, and Cas' smile widened.
"Well, don't you look pretty as a present, all stretched out for me?" Dean
said, his voice husky and low. Cas jumped slightly when he felt fingers press
against the small sliver of skin left showing where his shirt had risen up, and
Dean murmured an apology for scaring him. The bed dipped with the weight of
Dean laying down beside Cas, his fingers trailing lightly over the soft flesh
of Cas' abdomen.
Cas shivered under Dean's fingers and let his eyes drift open. Dean was staring
at his face, a soft expression over his countenance. Cas sighed and used a hand
to drag Dean's face closer, gently pressing their lips together. Dean groaned
in the back of throat and rolled over Cas, fitting a leg between Cas' already
spread thighs. Cas moaned breathily as Dean ground down slightly, his cock
stirring in his jeans. Dean kissed Cas more thoroughly, his tongue laving over
the back of Cas' teeth, sucking gently on the other's tongue as his hands ran
up and down Cas' sides.
"Dean," Cas moaned out, his hands fisting in the back of Dean's shirt. Dean's
eyes flash open then, his pupils overtaking the green of his eyes. He pulled
back immediately, running a hand through his hair as he hurried to adjust his
jeans.
"Sorry, Cas. Right, how 'bout a movie?" Dean was off Cas before he could
understand what was happening, his breathing labored, his cock half hard. After
a moment, Cas was able to gain use of his limbs and he got up and followed Dean
to the living room.
"Dean, what-." Cas tried, only to be cut off by Dean asking him if Rocky was
okay with him. Still confused and more than a little put out, Cas nodded and
sat down on the couch. Without meeting his eyes, Dean mumbled something about
food and dashed off to the kitchen.
Cas didn't know what to think. Dean had certainly never turned him down before.
Maybe after the last time they were together he realized that Cas wasn't going
to put out and wanted a boyfriend (or girlfriend) who would. Cas' heart seemed
to pump double time. What if Dean had only invited him here to break up with
Cas? But that wouldn't explain him staying the night? Maybe he just didn't have
the heart to tell Cas no...
Dean entered the room again holding a bowl of microwavable popcorn and, woah,
did Cas space out long enough for Dean to make popcorn? Dean set the the bowl
and a Coke in front of Cas, and very un-surreptitiously sat on the other side
of the couch. Cas could feel the space between like a lead weight tied to his
feet, ready to drag him down. He tried to focus on the movie, but Rocky was
Dean's favorite movie, not his. He only went with it because he always just
tagged along with whatever Dean did.
Cas sighed and curled in a ball, snuggling up to a pillow that smelled
suspiciously like Dean's apple shampoo.
About halfway through the movie, he felt Dean's hand on his back, scratching
lightly through the thin fabric. The couch shifted and then a solid weight was
pressing into his side. A slight tilt to the right and Cas was basically being
cradled by Dean, head squarely in the middle of his football toned chest. While
he was still confused, Cas felt comforted by Dean's presence, and they watched
the rest of the movie in silence.
From there it turned into a Rocky marathon, because Dean couldn't just watch
one, he had to finish the whole six movies in one night. Between Rocky II and
III, Cas excused himself to change into his pajamas.
In the bathroom, Cas pulled on Dean's favorite plaid pajama bottoms, soft, red
plaid. They were too big on Cas, so he had to roll the waistband so he wasn't
treading on the hems. Then he scavenged through Dean's drawers until he found
the one AC/DC shirt that was entirely too small for Dean, but would fit Cas'
leaner frame perfectly. He remembered back to the night when Dean first told
him how much he'd liked seeing Cas in his clothes. Dean had barely been able to
keep his hands off Cas when Dean had lent him some sweats for Cas to sleep in.
In the mirror, Cas mussed his hair a little more and swished some mouth wash
around. When Cas entered the living room again, Dean actually did a double
take. Cas smiled smugly and settled down back under Dean's arm. Cas went so far
as to rest his head on Dean's shoulder. He felt Dean shiver at the warm breath
Cas was blowing across his neck. Cas leaned in and pressed a kiss to the
underside of Dean's jaw. The arm slung around him tightened momentarily.
"Cas?" Dean asked shakily.
Cas hummed in acknowledgement as he nosed along the perfectly shaped, barely
stubbled jaw bone.
"What the hell are you doing?"
Now it was Cas' turn to tense up. Cas pulled back and looked Dean in his eyes.
"I'm kissing my boyfriend," He responded.
"I get that, but why?"
Anger and frustration and hurt exploded through Cas. He shoved Dean away and
stood up. "God, Dean, I'm trying to make you want me! Am I not good enough for
you, Dean? Because I don't understand what I did wrong!" Cas was dangerously
close to crying or hitting something, and he paced the urge off. Dean was just
staring up at Cas dumbly, jaw hanging open.
"What?" Cas spit.
''Make me want you? Cas," Dean stood up now, grabbing Cas by the hips and
stilling his sporadic movements. "Cas, I've always wanted you. You know that.
You haven't done anything wrong, babe."
Cas sagged in his arms. "Then why did you freak out earlier? And why won't you
let me touch you?"
Dean sighed loudly and pulled the shorter boy flush with his body. "Cas, I
don't want you to think we have to do anything you're not ready for."
"But you want it?" Cas' response was muffled by Dean's shirt.
"Yeah, of course I want it. I want to be the first one inside you, I want to
ruin you for other people. But. I don't want you to rush into it. I'm not going
anywhere if we don't fuck, Cas. I love you, period. Got that?"
Cas nodded, but pulled back again. "But what if I want it, too?" Dean looked
down at him dubiously.
"If you want to have sex, too, then lead the way," Dean slipped his hand into
Cas'.
Cas' heart thumped in his chest. He was actually going to do it. He was
actually going to lose his virginity. To Dean Winchester, no less, a popular
jock who happens to love Cas. Nerdy, inexperienced, Castiel Novak. His hand
shook slightly as he led Dean back to the bedroom. He stretched across the
comforter again, this time already ridding himself of his shirt. Dean's gaze
drifted over him appreciatively before he gently climbed over Cas and settled
most of his weight between Cas' legs.
"Have you ever done this with a boy before?" Cas whispered. He knew Dean had
plenty of experience with girls, but he also knew he was Dean's first actual
boyfriend. But that didn't mean that he hadn't been with another guy.
Dean nodded demurely and ducked his head in favor of marking up Cas' clavicle.
Surprisingly, Cas didn't feel jealous or angry at the confession at all. In
fact, a comforting warmth filled his chest at knowing that Dean would know how
to take care of him.
Dean was halfway down his chest by the town Cas stopped thinking about it.
Dean's pale pink tongue darted out to flick an already peaked nipple, and Cas
unexpectedly arched up into it.
"Cas, are your nipples sensitive?" Dean murmured lightly before taking said
nipple in his mouth. Cas moaned loudly at the wet heat surrounding the
sensitive nub. He could feel Dean smirk onto his chest. Dean's hands moved to
grip Cas' sides, pinning him in place as he ravaged Cas' chest, sucking hard on
the tender flesh. His teeth pressed in gently, and Cas cried out beneath him.
"Dean," Cas moaned, carding his hands through Dean's hair. He used the leverage
to pull Dean's mouth to his own, thrusting his tongue against Dean's as he
rolled his hips up into the older boy. Dean ground down hard against Cas'
hardening cock, making the younger boy pant and swear against his lips.
Dean pulled away, just enough to murmur, "Gotta get you stretched," along the
skin of Cas' neck, then he was gone, leaving Cas with cold air in his wake.
Dean returned to press one more kiss to Cas' lips before he moved down between
Cas' spread thighs. He took the waistband of the younger boy's red briefs in
his mouth and agonizingly slowly, he pulled them from Cas' legs. Cas' cock
jutted out proudly toward his flat stomach, not quite as long as Dean's, but
just as thick. The leaking head was angry red when Dean took it gently between
his lips. Unable to help himself, Cas thrust forward into the tight, wet heat,
savoring every moment he had with Dean's swollen mouth.
Cas barely noticed when Dean slipped a finger down his perineum. He jumped when
Dean slipped his lubed finger in past the first knuckle.
"Shhh, baby, gonna take care of you," Dean pulled off his cock to whisper,
before leaning down and taking him in his mouth again. Cas quivered between
Dean's tongue swirling around the slit of his dick and the finger barely
scraping his prostate, his chest heaving in an effort to catch his lost breath.
Dean's thick brown hair stood up where Cas had ran his hands through it.
Dean shifted slightly, allowing him to deep throat Cas as he urged another
finger past the tight ring of muscle.
"D-Dean, fuck, I think I'm gonna come," Cas whimpered in a rush. The older boy
brought his free hand up and circled his fingers around the underside of Cas'
balls, effectively staving off the younger boy's orgasm. Cas grunted
indignantly, hips thrusting harder into the plush, pink lips.
Finally managing to push his third finger into Cas' hole, Dean pulled off with
a lewd smack, and wiped a hand across his mouth before he leaned up to kiss
Cas. The younger boy was totally debauched; face red, swollen, pink lips parted
in a silent cry, eyes screwed shut. His chest was flushed from the exertion,
stomach caving inward as Cas held his breath from the pleasure.
Purple hickeys littered his chest and collarbones, and Dean smiled. Cas would
never forget this night.
"Alright, Cas," Dean breathed into his ear, "Tell me, for sure, you want to do
this. I won't be mad if you want to stop."
Cas nodded eagerly, his mouth opened and shut like a fish, but no words came
out.
Dean moved to line up with Cas' hole, but right before he pushed in, he leaned
down and kissed Cas tenderly, hand reaching up to pet Cas' sweat dampened hair.
Then he was inching in, infuriatingly slowly, easing in so as not to hurt Cas.
Cas screwed his eyes shut as he breathed through the pain of Dean stretching
him horribly wide, thick cock splitting him completely down the middle. When
Dean bottomed out, Cas let out a breath he hadn't known he'd been holding, and
wrapped his long legs around Dean's waist.
"Wait, wait wait," Cas moaned, slightly in pain. Dean looked down at his
boyfriend in concern, hand brushing the few tears staining his flushed cheeks.
"I know, baby," Dean murmured, kissing Cas' cheeks soothingly, "but I can make
it feel so much better," Dean punctuated his statement with a shallow roll of
his hips. Cas gasped hard, not quite used to being so filled, but tired of the
stalemate. He used his legs to urge Dean on faster, gasping and moaning under
his breath.
Dean set a fast, shallow pace until Cas was pushing into his thrusts, arm
jerking his cock roughly in time with Dean's thrusts. Then Dean hit that spot
inside Cas, and the younger boy arched off the bed into Dean.
"F-fuuuck, Dean, yesss,"Cas moaned. White hot fire burned through Cas' lower
abdomen and groin as he pumped his cock closer to his release. "Dean," he
keened, panting, "I'm so close, fuck, I'm gonna come." With that, Cas cried out
Dean's name came in thick white spurts all over his and Dean's chests. His body
spasmed and convulsed around Dean's dick. With a small, choked off sound, Dean
came inside Cas' tight hole, pumping him full of his come.
He collapsed onto the smaller boy, covering his sweat-sheened body with his
own. Cas let out an indignant grunt. Dean smiled and pulled out, Cas winced as
he pulled his limp cock free, and rolled to one side. He threw his arms around
his boyfriend and drew Cas to him.
"Now do you believe how much I want you?" Dean grumbled in his ear.
Sleep grasped at the soft edges, and as Cas slipped under its black embrace, he
whispered to Dean, "I love you."
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