Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/1030915.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M, Multi
  Fandom:
      Supernatural
  Relationship:
      Castiel/Dean_Winchester, Castiel/Samandriel, Michael/Samandriel, Castiel/
      Michael_(Supernatural)
  Additional Tags:
      Alternate_Universe_-_Human, Daddy_Kink, Dad!Dean, Dad!Michael, Light_Dom/
      sub, Naked_Cuddling, Blow_Jobs, Rimming, Double_Oral_Penetration,
      Dipping, Rough_Sex, Jealousy, Crying_Castiel, Orgasm_Denial, Cock_Rings,
      Bottom_Castiel, Bottom_Samandriel, Top_Dean, Top_Michael, Spanking
  Series:
      Part 2 of Daddy's_Boy
  Stats:
      Published: 2013-11-06 Words: 2145
****** Every Boy's Dream ******
by IceFemme
Summary
     Dean invites his dad friend Michael and his son over. Both men
     apparently have a thing for watching their boys cuddle.
     Castiel tries hard not to be jealous and begrudging of Samandriel
     when Dean picks the blond boy to fuck first.
Notes
     this became a really popular demand! it's k though because dad!dean
     is pretty legit (pssst so is brat!cas)
     im thinking castiel is around 17, samandriel is 19. dean & michael
     are both in mid to early thirties.
See the end of the work for more notes
Samandriel is a real sweetheart. Him and Castiel get along immediately, sitting
so close to each other and talking in hushed voices as Michael and Dean talk
about trivial things like football or places they’d like to go to hang out and
have a beer. Castiel always keeps a close eye on his dad when he’s with one of
his friends. Most of the time, Dean ends up drinking too much and likes to make
Castiel pretend like he doesn’t want to be fucked so that the brunette man can
‘rape’ him. Castiel will never admit that he secretly loves trying to squirm
away, but it is also painful sometimes and looking over at Samandriel, he
doesn’t look like he’s ever been involved in that kind of play before.
Michael walks into the living room and orders his boy to cuddle with Cas so
Dean and him can watch and stroke themselves.
The two boys are equally toned and cleanly shaven, meant to look like actual
young boys. Only Dean is harsh about keeping the hair completely invisible to
his eyes—there’s been more than one occasion where Castiel’s spread out and
waiting for his dad to fuck him but will be completely denied when Dean sees
one black stubble forming above his little cock. It’s humiliating, and it
usually comes with a lecture on obedience and how Castiel is a bad little boy
who deserves little.
Samandriel places a hand on either side of Castiel’s head and the younger boy
blushes. He knows Samandriel is going to lean in and kiss him, and his heart
pumps erratically. It’s different when he kisses other men as opposed to his
dad. With Dean, everything is comfortable, predictable. However, with others,
Castiel never knows what to expect.
So when the blonde boy leans in and presses their lips together softly, Castiel
lets out a surprised moan. The kiss is chaste, but Samandriel's long, thin
fingers start to prod Cas’ puckered little nipples. Castiel’s arm reaches up
and he wraps it around Samandriel’s waist, pulling him in closer so that their
unclothed cocks can brush.
Both boys shudder and roll over so that Castiel is now on top. He’s a greedy
little boy and starts to grind his ass down on Samandriel’s rapidly thickening
cock. The older boy beneath him moans loudly and holds his hips in place,
grinding his teeth together as Castiel continues to gyrate.
Dean is the first one to make a sound. He growls heartily and both boys on the
bed look over and see him with his hand wrapped firmly around his cock. He
hasn’t even taken his pants off; the jeans and tight briefs are just pushed
down below his heavy balls.
“Daddy, can Samandriel fuck me?” Castiel asks from the bed, arching his back
prettily and this causes Michael to moan and lift his arm around the back of
the nice leather couch behind Castiel’s dad’s head. “He’s sohard.”
Dean shrugs. “If you can take him all in your mouth, we’ll see,” he suggests,
smirking because he knows how impatient Castiel can get. “Sami can play with
your eager hole while he gets serviced.”
Castiel puts on a determined face. His dad wants him to put on a show for him?
He’ll give him a show.
He turns around on top of Samandriel and positions his face right above the
boy’s mostly hairless cock. He starts with his lips pressed to the tip, just
kissing him before he opens his mouth and slowly starts sucking him down. He
keeps his mouth closed tight around the cock, careful to keep his teeth out of
the way. Samandriel’s moan of pleasure alerts the dark haired boy he’s doing a
good job.
“Hey, this one too,” Michael says, standing up from the couch next to Dean and
approaching Castiel on the bed. His cock is hard and it stays just a little
less than 6 inches away from the boy’s face. Michael’s taunting him with it and
it makes the boy’s face glow red with embarrassment.
The man is extremely hot. That’s probably why he makes Castiel feel so timid,
so childish next to his chiseled Italian God body. Dean’s similar in this
aspect—making Castiel feel small and young in comparison. While both of
Michael’s parents must have been of Italian decent, Dean was only half.
“C’mon, baby boy,” Michael moans, grabbing one of Castiel’s hands to put on his
cock. Castiel eagerly begins to jerk it off, alternating from Samandriel’s
slick cockhead to Michael’s. “Goddamn it, Dean. You’ve raised a filthy boy.”
Dean smirks proudly. “Don’t I fuckin’ know it,” he boasts, not rising from his
seat. Castiel’s eyes seek out his slick red cock and his mouth waters. He
remembers his task at hand when Samandriel’s wet tongue presses against his
hole and the boy drops his head to suck Michael's cock into his mouth.
“Filthy fucking slut,” Michael says and reaches over to pull Cas’ ass cheek up
to see where Samandriel’s tongue is connected to him. “Samandriel move over,”
he orders his son as he pulls Castiel’s face off his cock. Samandriel scrambles
to get out from under Castiel’s body, wanting to please his dad as quick as
possible.
Castiel’s flipped over so fast—he’s on his back now, being pushed up onto his
shoulders and neck so that his ass is up in the air. “S—sir!” Castiel cries in
alarm.
Michael clasps his hands over Castiel’s ass cheeks and pulls them apart to see
Castiel’s hole. He smirks briefly before spiting down into it, hooking his
thumbs inside to open it more and his spit goes right inside.
The dark haired boy doesn’t even care that it’s not his dad fucking him.
Michael’s not as thick as Dean but Castiel still screams when he plunges in, at
first just dipping from above, but then pounding the boy into the mattress. His
hands clutch for the sheets around him so that he doesn’t loose his grip and
smack his body on the headboard. The angle is uncomfortable but the pain makes
Castiel’s cock brow harder with every thrust inside of him.
Soon enough it registers to Castiel that he’s not the only one screaming. He
looks over as far as he can and just barely, he can see Samandriel sitting on
Dean’s cock. Castiel’s dad’s hands are snug on the boy’s hips and it makes
Castiel’s chest burn with jealousy. Samandriel’s got his head thrown back and
all, his mouth ajar and blonde hair flying around his head.
Castiel’s brought back to the real world when Michael’s hand comes down hard on
his ass. He reaches around and smacks Castiel’s hard cock, which elicits a
piercing scream from the red-faced boy.
“Sir—sirrrr!” Castiel’s voice comes out slurred and his eyebrows draw together
when Michael presses down on his perineum. It stimulates his prostate so
intensely that his vision goes black for a moment and if it weren’t for his
cock ring, he would have come immediately.
He continues his brutal thrusts, pushing Castiel in so that his body is caving
in on it’s self.
When Michael finally looks down at the boy below him, there are tears flowing
freely down Cas’ cheeks and his arms are crushed under his chest. Michael pulls
out and smirks.
“Do you want your daddy?” he asks, squeezing his fleshy ass hard and the boy
whimpers. “Are you crying for your daddy?”
Castiel sniffles quickly, feeling ashamed for letting his emotions get the
better of him. “Y—yes.”
Dean appears behind Michael and he comes in and absolutely scoops his boy up.
Castiel clings tight to him, seeking his warmth and trying to ignore the fact
that he totally smells like sex and he wasn’t involved.
Of course, Castiel knows that Dean isn’t committed only to Castiel. It’s harsh
and Castiel cries about it sometimes, but Dean fucks other boys. It apparently
turns him on to have his little houseboy waiting for his every return, to come
back home smelling like others and then have Cas clean his cock off.
Dean lies him down on the bed and soothes Cas’ hair back off his sweaty
forehead. He lifts one leg up over his broad shoulder and positions his cock
right at Castiel’s entrance, just tracing his tip along the rim to totally piss
his boy off.
“D—dad,” Castiel whispers and he’s afraid it’s gone unheard because Samandriel
moans loudly when Michael holds his head to the wall and fingers his boy’s hole
roughly. Castiel’s glad his daddy doesn’t toss him around like that. Maybe
later, when he’s stronger and older, but now Castiel likes to be treated
gently. Like a princess.
“Daddy’s here,” Dean whispers back, pulling Castiel’s hips into his so that he
penetrates his boy. Castiel’s voice is sore by now from all the yelling
earlier, and he just moans softly.
“I missed you,” he says and thumbs away a tear from his cheek. Dean smirks and
sucks the thumb into his mouth. He licks over the finger pad and Castiel gives
a little thrust of his hips.
“Fuck,” Dean growls around the thumb in his mouth. Castiel knows that his dad’s
close and he has to coax him to completion. He squeezes his ass around Dean’s
thick cock inside of him, closing his eyes and biting his lower lip.
“Please, cum inside me daddy,” Castiel murmurs, “mark me, dad, please, only
me!”
“Okay baby,” Dean says, and speeds up his thrusts. He moans loudly, grunting
and growling as his hips stutter against Castiel’s. He pushes forward,
stretching Castiel’s leg that’s slung over his freckled shoulder.
“Fucking—shit, Cas!”
Castiel can feel the hot squirt of cum shoot inside of him. He squeals, giddy
with knowledge that the cum is inside of him,not the other boy.
So he’s selfish. Shoot him.
His greedy hole convulses around Dean’s cock, collecting it all so the cum
doesn’t come out with Dean’s cock. Dean grabs a plug from the dresser and
pushes it into his obedient little boy. Castiel moans around it, whining
because his cock is so fucking painfully hard and he wants to cum so bad but
the cock ring is extremely restricting.
“D—dad, can—my boy sperm is so much—” Castiel says in a wavering voice but Dean
gives him a brief spank on his ass.
Michael takes Samandriel home an hour later. Samandriel evidently sleeps after
getting fucked and it took a little while for him to recharge after both his
dad and Dean taking turns with him.
Castiel made Annie’s Mac n Cheese and shared with his dad while they watched a
little bit of old Scooby Doo reruns (because it’s Cas’ all time favourite).
Dean made tea around eleven at night and came in the living room to see his son
sitting by the window in the front room.
“You look upset, baby. What’s wrong? Did Michael hurt you?” Dean asks. His eyes
go from concerned to furious in a matter of milliseconds.
“I just…” Castiel’s eyes water and tears threaten to spill again. He looks up
at his dad and Dean sort of melts. Sort of, like he crumbles to pieces and
scoops up his son onto his lap so he can envelope him in his arms. “I always
want to make you happy, and I feel like I’m an inadequate son for you.”
“Baby, why would you think that?” Dean asks, leaning in and kissing Castiel’s
forehead.
“Because you don’t only fuck me,” he says but it comes out as more of a whine.
“I’m sorry if I sound like a brat.”
Dean looks at Castiel and smiles. “You’re not sorry, Princess.”
“No, but—!” Dean bursts out laughing and Castiel tries to keep a straight face,
“Dad—! How about if I can keep my grades up—”
“Which is impossible, apparently,” Dean grumbles.
“You stop fucking your friends’ boys. Unless I’m there or I say it’s okay, that
is,” Castiel adds the last part impishly with a blush.
“You’ve got a deal,” Dean says, kissing his son on the lips. “But for the
record, Sami’s the first one I’ve fucked that isn’t you since you were
sixteen.”
Castiel’s jaw drops. “It’s been that long? I mean, I’m only seventeen and three
quarters, but still.”
“It’s actually just a selfish thing,” he shrugs and tightens his arms around
Castiel’s waist. “I don’t like to share you, so I don’t go fucking my friend’s
sons.” He hoists Castiel into the air and carries his son into his room. “You
don’t let any boys at school fuck you, right?” he asks cautiously once in bed.
“Never,” Castiel swears, although it’s almost happened more times than he can
count. Maybe one day, he thinks with a blush. Dean narrows his eyes and Castiel
giggles, “I promise!”
End Notes
     there are more ficlets on my tumblr. (updated since last post)
     headcanons always welcome!
     also! smut side_blog
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