Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/840644.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Castiel/Dean_Winchester
  Character:
      Castiel, Adam_Milligan, Dean_Winchester, Lisa_Braeden, Anna_Milton
  Additional Tags:
      Best_Friends, Sleepovers, Daddy_Kink, Blow_Jobs, Rimming, Fingerfucking,
      Loss_of_Virginity, Anal_Sex, Cock_Tease, Anal_Plug, Barebacking,
      Alternate_Universe_-_Human
  Stats:
      Published: 2013-06-13 Words: 4277
****** Adam's Dad ******
by IceFemme
Summary
     Prompt: 17 year old Cas who is having a secret affair with his best
     friend's dad, Dean Winchester.
Notes
     Castiel and Adam have been friends since second grade.
See the end of the work for more notes
 
“I’m here; come outside, you fuck! I can’t exactly break a door down yet, but
I’m getting there.”
Adam rolled his eyes on his side of the line. “Wow, are you trying to hit on me
because you know I don’t swing that way,” he said and hopped off his bed. All
he had to do was press the buzzer so that he could come up on his own. "Just
kidding, it's totally working," he whispered teasingly before he hung up on his
best friend and padded back into his room. “Dad! Cas is on his way up!” he
called behind him, doubting that his dad was actually listening or for that
matter, cared.
After Adam’s mother died, his dad had decided that he would go all out. He
started his own business and it really skyrocketed, so they had moved from
their one story house to a bigger apartment in the city. Castiel enjoyed coming
over now because they lived much closer, and he was on the track and cross-
country team, so he could take ten flights of stairs. But on the seventh, he
was kind of wishing he had taken the elevator.
The door was left unlocked when he finally made it up, breathing heavily and a
little red-faced. He pushed it open like he always used to when Adam lived in
his smaller house and just entered, placing his over night back on the floor as
he untied his shoes. He didn’t expect to see his best friend’s dad, the
notorious womanizer Dean Winchester, to be walking around in a pair of tight
black briefs and only a pair of tight black briefs with his music plugged in
playing loud in his earphones.
“Whoa!” Dean cried in shock. He ripped his earphones out and apologized. “Oh my
God, Cas, I had no idea you were coming—Adam!” he turned his head and called.
Castiel’s eyes were fixed on his black ink tattoo over his left pectoral. He’d
seen it before, hell even commented on how cool it was when he and Adam had
been younger and Dean took them to the pool. But now, what with his golden skin
and hairless chest, he looked so much younger with it. And for some reason,
that turned Castiel on.
Adam came out a moment later with his arms crossed over his chest. He waved to
Castiel, but Dean waved his hand over. “Dad, why are you naked?” he asked with
a sneer.
“Uhh—not important.” His dad wiped a hand down his rock hard abdomen and
Castiel’s eyes followed the entire movement. Wow, Castiel thought, his mind
going blank. Dean had never been one for exercising—he assumed it safe to say
Adam’s dad was looking pretty fucking good.
“Adam, why didn’t you tell me Cas was coming over?” he asked. Castiel couldn’t
tear his eyes away from the six foot one man if he tried. Adam glared at his
dad.
Castiel’s best friend huffed loudly. “Because I did tell you, father. You are
just never listening to me anymore!” he said angrily, his hands balled up in
fists at his side. Dean looked at him like, really? You in another one of your
bitch moods? Dean placed his hands on his hips and—yet again—the muscles in his
upper arms were bulging accompanied by a light sheen of sweat as if to show
that Dean had been throwing working out previously.
If he knew he was staring, Dean didn’t say anything. He only shrugged then, in
spite of his son. “Yeah. I guess you’re right,” he pursed his lips and checked
out his fingernails nonchalantly, “maybe that’s why I ordered a large half
mushrooms, half pepperoni and sausage—just the way you don’t like it.”
Adam glowered at his dad in return. “You think you’re cool, dad. Just stop.” He
turned to Castiel and his face almost immediately lit up like a Christmas tree.
“Come on. I got a new game!” he exclaimed happily.
Castiel shot a look at Dean one last time before he got pulled along with his
moody best friend. He found himself blushing—in what? Was it embarrassment for
catching him with absolutely nothing on? (Not to mention he still hadn’t
changed or covered his body) Or was it for figuring out for the first time how
astonishingly hot Dean Winchester is?
So he rolled his shoulders and waved at the Greek God that was his best
friend’s father and continued on behind Adam into his room at the end of the
hall. The walls were painted a soft green, but posters of cool bands or video
game promos hid most of it, Castiel never found the time to actually map it all
out.
“Dude. I heard Anna Milton has a thing for blond guys with blue eyes!”
Castiel scoffed. “So basically Nazis?” he asked sarcastically, popping a chip
into his mouth and throwing his joystick into the air as Adam began belting out
laughing. “That’s a little weird, Adam. Maybe you shouldn’t affiliate yourself
with people like her.”
He was still laughing, but he managed to argue, “Shut up, Cas! She’s the
hottest girl at our school. No doubt.”
“Yeah, hot for a Nazi, I guess,” Castiel joked further until Adam punched him
in the shoulder and he winced.
A knock came from Adam’s door and Castiel glanced at the clock. It had been
over an hour already. “Pizza’s here, boys,” Dean announced, leaving the door
open behind him as he walked down the hall into the kitchen; Castiel watched
his hips move as he went.
Adam rolled off his bed and sprung to his feet. “I’m going to rub my dick in
that pizza I’m so ready for it,” he said, rubbing his stomach as Castiel
anxiously walked behind him.
Yes, this was his best friend.
When they entered the kitchen, they saw the brunette man pulling sodas out of
the fridge. “Hey, dad, is Lisa coming over?” Dean cocks his head to the side. A
scoff comes from the boy next to him and Castiel wonders if Adam is just
playing a joke on his dad. “Lisa Braeden? You know, the one with Ben?” he
asked. Realization popped on Dean’s face.
“Oh, yeah. Yeah. Wait, how did you know she come over?” he asked, picking a
piece of Castiel’s mushroom side off and tossed it into his mouth. “We went on
a date, like, twice last month.”
Adam shrugged. “Walls are thin.”
Castiel had an odd idea to ask Dean who Lisa was. How close were they? Did he
fuck her every weekend? And who the hell was Ben?
Although Adam doesn’t like to acknowledge it, he loves his father. Dean comes
into the living room and sits with the two teenagers while they watch a new
horror film. Castiel’s never heard of it, but Adam has seen it “like a million
times, dude” so he trusts it’s decent.
Dean comes in and sits on the other side of Cas, leaning back against the black
leather couch and closing his eyes. Adam and Dean are avid movie watchers, so
Adam doesn’t even seem to notice when his dad had come in.
But Castiel does, and he watches him out of the corner of his eye. It’s weird,
and he doesn’t know if he feels good about himself staring so damn much at
pretty much his second father, but something about Dean has changed. And
Castiel loves it.
Dean’s always been an awesome dad to Adam and, in a sense, Castiel feels like
he had been his substitute dad for a part of his life when his own father had.
It had been a rough patch in his life, but he had Adam and Dean to help Castiel
and his mother get through the days.
Castiel pretends to play with his fingers. His head starts to tilt and he feels
a bit sleepy. He assumes that his head has hit the back of the couch but it
shifts under him and Castiel freezes.
It's Dean's bicep that's wrapped around the back of the couch, his hand
extending to touch some of the hairs on the top of Adam's head.
This shocks Castiel because it's small, but it's intimate and it makes his
cheeks heat up in embarrassment and surprise that the man hasn't pulled his arm
away yet, but instead shift so that Cas' head was resting closer to his neck.
He bit his lip, pulling the blanket up higher on his lap just barely
suppressing a shiver.
The doorbell rang and Dean lifted his arm up in shock to jump up from his seat.
Adam hardly noticed, but instead rolled his eyes and mumbled under his breath,
“Here comes the slut.”
Castiel gulped, watching as the Lisa Braeden girl walked in through the door, a
bottle of wine in her hands. She was tall and lithe with long dark hair, a
similar colour to Castiel’s. She was exactly the type of girl that Dean had
been dating ever since Rachel died. There had been Jo, who had been a blind
date but Dean ended up really liking her—as a little sister. Then Bela, who had
been a complete gold digger but when she found out Dean couldn’t give her a
diamond ring she left. Of course there was Eve, Ruby, Charlie (who evidently
had forgotten to mention she was bi-sexual and then decided she was lesbian)
and the list went on.
This was the reason Adam called his dad a ‘man-whore’.
Lisa giggled loudly and looked in at Adam and Cas and sent them a flirty wave.
“Hey, boys!”
Adam coughed something under his breath and Castiel made a half-assed attempt
to raise his hand and wave. “She’s like twenty-seven and she’s got an eight
year old.” Adam scoffed. Castiel wasn’t so quick to judge, but he sure as hell
didn’t like the way she was running her fingers up and down his toned arm or
the way he was reciprocating their make out session.
===============================================================================
When the movie ended, Castiel had to help his friend up off the couch. In the
spans of a two hour movie, Adam had drank amost three beers. He was mumbling
nosense in his sleep, but Castiel managed to get him on his feet and down the
hall into his own bed. Normally Cas would fight with him who got to sleep
there, but the dude was out cold the second his head hit the pillow. 
Castiel changed his clothing easily and went outside the room, glancing down
the hall where the dinning room was. Dean was sat so that he was facing Castiel
where as Lisa was looking the other way. Without any shyness or sense of
embarrassment, Castiel fished his hand into his shorts and began stroking
himself. Dean was gorgeous and Castiel had never paid such particular attention
to him until now and it was driving him crazy.
And then all too suddenly Cas caught on that Dean was staring straight at him.
Castiel took a deep breath and watched as Dean rose from his chair, which
scraped loudly against the floor, and muttered something about going to the
bathroom.
Castiel quickly scuffled out of the doorway and darted out of the room, careful
to stay out of Lisa’s sight. When he made it to the bathroom, he was almost
surprised to find it unlocked.
Hopefully Lisa didn’t hear the loud click that came with closing the door.
Dean’s head shot up. His cashmere sweater and button down were pushed up his
elegantly toned chest and his nice black slacks were wide open and sliding down
his slim thighs. More importantly, his thick, red cock was grasped tightly in
those calloused hands that he remembered were massaging his own just hours ago.
A pearl of precum was at his very tip, and Castiel had to take another deep
breath to calm him. His soldier was standing to attention in his own pants and
Dean’s approval of that was enough for Cas to drop to his knees before the
older man.
“Shit!” Dean whispered loudly. It almost seemed too loud in the silent house.
Lisa was probably at the table, sipping her wine, wondering why Dean was taking
so long. Adam was definitely still out cold. “Cas, you can’t do this! Get
off—get up!”
Castiel removed Dean’s pliable fingers with ease—almost wanting to laugh at how
easy it was to get him to move.
Dean was running out of excuses. “Cas, I’mthirty-nine!”
The dark haired boy shot a glare up at Dean. “Why the fuck should I care?”
Castiel rasped, spitting into his hand and rubbing it up and down Dean’s
length. In other words, this is what I want to do, so let me.At that
point, Dean did absolutely nothing to stop him. Dean needed something steady to
hold on to, so he reached up and caught the metal of the shower glass in his
hand, a ring on his finger making a loud clinking noise.
The blue in Castiel’s eyes were gone, his pupil blown wide; Dean had a similar
story. But it was more difficult for Dean—he had a date waiting just down the
hall from where he was with his son’s best friend who was on his knees sucking
his goddamn cock with such vigor that it seemed like the kid could do it for a
living.
But Castiel was stubborn; Dean knew that for a fact. He’d known the boy for
around ten years, so he got to know a lot of his antics early on. So exactly
why was he in the bathroom with the child that Dean had practically helped
raise, allowing him to suck him off so good? And the fact that this was ten
times better than it was with the dark haired vixen in the other room was not
helping.
It was too late to stop any of this, because he was already on his toes, his
orgasm coiling in his lower stomach and pleading to burst but he didn’t want to
go out that easy—especially not give Cas any ideas of how much this own
scenario was turning him on right now.
“Deann…” Castiel moaned on his dick. His tongue swirled around the head and
Castiel made an effort to be looking square in his friend’s dad’s eyes. Dean
almost felt regretful that he had allowed the kid to call him by his first name
in the first place. He moaned around Dean’s girth one more time as he tongued
the slit at his head and the older man was cumming buckets down Cas’ throat.
When the raven-haired boy began choking, Dean pulled out and continued to burst
over the boy’s lips and cheeks.
Both of them were breathing heavily, looking over each other with lust blown
eyes.
“Tell her to leave,” Castiel whispered hoarsely. It was so fucking sexy that
Dean stuffed his now semi back into his slacks and pulled his shirts down,
turning on his heel and leaving the bathroom, swiftly shutting the door behind
him.
Dean told her some bullshit that his mother was sick and he needed to go over
right away to attend to her. Lisa understood, although a little suspicious, and
picked up her purse. She pecked Dean on the lips before he could say anything
about it and walked out, shouting for him to call her sometime soon.
He swallowed, turning to seeing Castiel leaning against the wall, a prominent
glare focused at the closed door as he swiped his fingers down his face and
brought them to his lips for a delicious taste. He moaned especially loud when
he got a wad in his mouth, his hand slipping down his front to grope his cock
beneath his pants.
Dean caught the boy’s wrist and yanked it out of his mouth. “I hope you know
what you’ve just got yourself into.”
Castiel licked his lips then and smiled. “If you had even the tiniest bit of
respect for her, you would’ve told her your mother died when you were four.”
Dean bit his lower lip, just staring at the boy under him against the wall.
“You know, my cum all over your face isn’t such a bad look on you.”
Castiel giggled like a little schoolgirl and lifted up his arms to snake around
the older man’s neck to pull him in close so they were a breath away.
“So are you going to fuck me, or are we going to pretend I didn’t just give you
head in Adam’s bathroom?” he asked, licking up another bit of cum that had
caught on his lip.
Their lips smashed together and Dean slipped his hands down to Cas’ ass and
cupped his two cheeks, spreading them apart as their lips tangled in each
other’s mouths. “I would like that very much,” Dean admitted.
And fuck if Dean wasn’t strong. He lifted Cas’ hips up so that the younger boy
could wrap his long legs around Dean’s waist and gyrate their cocks together.
It was perfect even with the clothing barrier.
Dean threw Cas down on his bed, shutting the door and locking it behind him as
he slowly began to strip. The cashmere was off immediately and the boys vaguely
heard it hit the wall. He unbuttoned his shirt slowly next, and by that time
Cas had had enough. He lurched forward, his pants and tee already on the floor
and he was on his knees on the bed, bent over and pulling Dean’s belt open.
At that point, he grabbed the button and pulled, the expensive pants splitting
open and sagging down Dean’s exponentially muscular legs, then dropping at his
bare feet. Castiel gave the brunette man’s cock a few teasing kitten licks
before Dean got a grapple on the boy’s hips and flipped him over.
“You want me to fuck you, boy?”
Castiel’s legs split open as an offering and he moaned yes, yes, yes over and
over. He could obscurely acknowledge that he was being extremely slutty, but he
couldn’t contain himself if he tried. Dean’s hands dug into Cas’ meaty thighs,
holding them open so the man could lean in and lick one fat stripe up Castiel’s
balls.
“Eat me, eat me, oh fuck eat me!” Castiel cried as wantonly as he could when
Dean began sucking one testicle at a time.
With that, Dean aggressively flipped the seventeen-year-old onto his stomach
and then pulled his knees up so his ass was in the air. Cas cried out in shock
but Dean was quick to shush him, to remind him that his son, that Castiel’s
best friend was just down the hall.
Dean spread Castiel’s ass cheeks wide again, but this time he got a front seat
view. And God if his little pucker wasn’t the most beautiful thing—it was
unused, completely pink and responsive to Dean’s wet finger trailing along the
rim. “Gorgeous,” Dean muttered as he leant in to place a chaste kiss to
Castiel’s hole.
The touch of lips to his sensitive ass caught Cas completely by surprise. But
Dean didn’t give him a whole lot of time to get used to it—he opened his lips
and lightly teased his teeth on the boy’s rim, tugging a little before his
tongue darted out and licked the entire hole. Castiel had to muffle his cries
into the pillow as Dean's tongue and fingers sliped into him.
“Fuck, baby; your sluthole is so irresistible,” Dean mumbled, pulling his mouth
away from Cas’ entrance and then got up onto his knees. Castiel sobs as Dean
turns him onto his side and places one leg up in the air. He reached down and
grasps Dean’s cock in his hand and began to jerk it off, getting Dean nice and
hard as his tip prods Cas’ hole.
Dean moves in powerfully and Castiel starts to shake. Once he gets enough time
to adjust to the mass inside of him, Dean leans in to Castiel’s ear and starts
talking filth.
“This turning you on real nice, baby? Yeah? Never took you as a daddy’s boy,
Cas,” he said haughtily.
He began the pounding, pushing in real far and finding that spot inside of Cas
almost immediately that made him writhe and quake with pleasure. “F—fuck! I
only want to be fucked by Daddy,” Castiel admitted, his eyes squeezing shut as
Dean finds that spot again.
With this knowledge, Dean begins to ruthlessly plunge inside of the teen, his
freckled face heating up. It was weird to acknowledge that he hadn’t done
something so kinky in years—and it made his cock all the thicker to recognize
that the boy below him was illegal. It was like public sex—another thing he
hadn’t done in forever—completely audacious but too good to resist.
Dean held the teen’s leg tightly against his chest as he started mercilessly
thrusting into Castiel. It was beyond good—his heat was sucking him in like
nothing he had felt in a long time. Not to mention the strings of 'Daddy, fuck!
Daddy, Daddy, Daddy!' was starting to make Dean go insane with gratification.
“You’re going to fucking make me cum, you fucking slut! Cas!” Dean ground out;
rolling his hips in a stuttering rhythm that Cas wasn’t helping by slamming his
ass back onto him.
“Cum inside of me!” Castiel shouted into the pillow that was clutched in a
death grip to his face. “Ohhh—oh fuck! Dean! Inside, please Dean, pleeeease!”
Dean grunted some more, grabbing Cas’ cock and giving it a few tight strokes
before he was cumming all over his hand and his own chest.
Cas fucked himself throughout his orgasm, pushing back on Dean’s dick and felt
exactly when the older man had lost his rhythm and thoroughly filled Cas’
little ass with his hot cum. He breathed heavily as he pulled his softening
cock out.
Castiel mewled in delight, rolling onto his back so he could catch his breath
and look at Dean. He carded his fingers down his chest until he found the pool
of cum on his lower stomach.
Dean ran a hand through his hair, pretty much everything dawning on him in that
second when he realized he was looking at Castiel. Castiel Novak, the boy he's
known for more or less of a decade.
His anger was explosive, and he couldn't control when he tightened his hands to
fists at his side. "I turn forty in six months, Cas! Do you fucking understand
that!?" Dean shouted at the boy. Castiel sat at the edge of the bed.
There was a small quirk in his lips and he replied, "Well I turn eighteen in
two weeks, so what's the big deal?" 
Dean looked outraged. He was embarrassed, there was that, but he was also
ashamed of how he had let the night go.
"Go to bed." It was a domineering tone and Castiel flinched.
He didn't speak either, but instead he picked his clothes up off the floor and
began to dress himself, never lowering his gaze from Dean's. It was his own way
of being defiant.
===============================================================================
Castiel's hands dug into Dean's ass cheeks. His cock was so far down Castiel's
throat the man was practically seeing stars.
It made so much hotter that Cas had his own hand on his cock, working it up and
down his length. Dean could vaguely remember something he was saying about
people coming over soon, but what with his cock getting sucked into oblivion
currently, it was placed on the back burner.
Dean and Castiel had set up a system. 
Whenever Castiel would come over on the weekends to sleepover, Dean was off
limits until Adam was in his bed, dead asleep. It had taken quite a while to
put this plan into action as the morning after the first time Dean had fucked
Castiel, Adam had left to go to his lacrosse game right away. He had driven
himself over, so almost immediately after Adam had left, Castiel rode Dean's
cock for hours.
There was something about a party happening at Dean's house... Yeah, for his
promotion? Dean's eyes snapped open wide enough for a moment to glance at the
clock on the wall.
"Fuck, Cas!" he growled as Castiel hollowed out his cheeks as he sucked harder
than before. "Running out of time," he whispered harshly.
And all Castiel had to do was lift his gaze up so that he was staring at Dean
with his blown azure blue eyes and Dean was a goner. He came in long white
strips all down his son's best friend's face. 
"Shit, Cas," Dean breathed. He really does look fucking good with my cum all
over him, he thought to himself.
"Hey, Adam! Do you know where my brother is?" came a voice from the door. 
Dean cursed again and zipped his jeans back up. He shot a look at Castiel on
his knees who looked so fucking horny and so mouthwatering. Castiel stood up
and threw his arms around Dean's neck and pressed their lips together for a few
seconds. Dean slipped his hand under Castiel's cargo shorts and felt along the
cleft of his ass, smiling. 
"I put my plug in last night," Castiel said with a small, strawberry blush on
his cheeks.
He was so filled with glee that he dipped down and kissed Castiel on the lips
again. "Happy Birthday, Cas."
Castiel just smiled. "We're here to celebrate you," he said shyly. "Tonight,
though. Tonight I want my present."
End Notes
     Prompt by subbycas on tumblr.
     i'm currently working on an omega!cas & alpha!dean story so i was
     wondering if anyone would like to beta for me or give me other
     prompts? ...or just talk to me ;A; that would be profound.
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