Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/1019900.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M, Multi
  Fandom:
      Supernatural
  Relationship:
      Castiel/Dean_Winchester, Castiel/Jimmy_Novak, Dean_Winchester/Jimmy
      Novak, Castiel/Jimmy_Novak/Dean_Winchester
  Character:
      Castiel, Dean_Winchester, Jimmy_Novak, Gabriel_(Supernatural)
  Additional Tags:
      Explicit_Sexual_Content, Twincest, Threesome_-_M/M/M, Underage_Sex, Oral
      Sex, Anal_Sex, Dirty_Talk, Dom/sub, Dominant_Dean, Dominant_Jimmy,
      Submissive_Jimmy, Submissive_Castiel, Spanking, Comeplay, Spitroasting,
      Facials, Bottom_Castiel, Top_Dean, Masturbation, Face-Fucking, mild
      breathplay, Rimming, Tag_all_the_kinks!, Gabriel_is_maybe_not_the_best
      guardian_for_the_twins, Gabriel_is_actually_a_little_shit, but_that's
      nothing_new
  Stats:
      Published: 2013-10-27 Words: 3387
****** Double Your Pleasure, Double Your Fun ******
by weesynthpixie
Summary
     They are twins, and Dean is probably going to Hell.
Notes
See the end of the work for notes
They are twins, and Dean is probably going to Hell.
Or maybe not. Maybe this is more something along the lines of Dean died and
went to heaven; a very perverted but enticing heaven. This heaven has two boys
(seventeen-year-olds oh lord) with thick dark hair and pretty blue eyes. Their
lips are nice and plump, perfect for sucking cock (especially Dean’s).
Dean might also add that they are totally cool with the whole twincest thing.
Right now, Castiel and Jimmy are sitting on Jimmy’s bed, kissing each other
like they’re starved for their saliva or something. Dean…well Dean is standing
at the entrance to the twin’s room after being told by their older brother
Gabriel (who saucily winked at Dean and then promptly left) that the boys were
upstairs. Thankfully, the twins are under Gabriel’s guardianship, so when
Gabriel left, they were completely alone.
He’s still processing the whole situation, standing as still as possible.
Castiel and Jimmy seem oblivious as they continue to practically devour each
other, and maybe Dean is getting a bit hard in his jeans but, hey, who
wouldn’t? He licks his suddenly dry lips as Jimmy detaches from Castiel’s lips
to start attacking his neck instead. Castiel is needy as all hell as he runs
his hands all over Jimmy’s body, even going so far as to scratch nails down his
back through the tank-top he’s currently wearing. Castiel is already naked,
which doesn’t surprise Dean at all. Jimmy likes to work fast. The noises
Castiel makes as Jimmy sucks a nice bruise into his twin’s neck are going
straight to Dean’s hardening dick.
Fuck he needs to be in that bed right now.
“Hello, Dean,” Castiel says, all raspy like he’s been screaming himself hoarse
all day. That’s a very good possibility with how Jimmy treats Castiel during
sex. Dean spent a whole night just watching what those two get up to during
their sexual escapades. Dean came maybe a half a dozen times in a span of five
hours before Gabriel came home and kicked him out. It was so ridiculously hot
that all porn was forever ruined for him after that. If Dean wants a good
jacking off session, he’ll just go to the Novak’s.
Jimmy is a rare specimen in Dean’s opinion. He’s what they call a “switch” in
the dom/sub culture. Depending on who he’s with, he can easily slip into the
role of either a dominant or a submissive. With Castiel, he’s dominant and with
Dean he’s submissive (with tendencies to be a really bitchy, demanding bottom
but Dean likes it all the same).
At Castiel’s greeting, Jimmy looks over to Dean as he continues to lick and
kiss at the bruise starting to form on the twin’s neck. His gaze is heated and
damn if Dean is just going to ignore the hunger in that boy’s eyes.
“Hey there, Dean. Wanna come play? I’m getting Cas here nice and ready for
you.”
Dean only hums and strips out of his Zeppelin shirt. He lets it fall to the
floor beneath before moving his hands down to undo the belt on his jeans. Both
boys watch him intently as Dean thumbs at the button and zipper, being
agonizingly slow just for their benefit. Cas moans from beside Jimmy as Dean
pulls his cock out of the slit in his shorts. Pre-cum is dribbling steadily out
of the head. Dean can tell that Castiel desperately wants to crawl over to
where Dean is standing, but Jimmy is holding him back with a hand on his neck.
Jimmy speaks quietly into his ear. “Mmm baby brother, you’re practically
drooling over Dean’s cock. Do you want it?” Cas nods his head and licks his
lips, eyes going wide and pupils swallowing up the blue. “You have to beg for
it. Only good boys get Dean’s cock.”
“I want it,” Cas whispers oh so sweetly, like a good boy. Dean groans when
Jimmy bites Cas’s earlobe playfully and laughs. Castiel’s body is tense, but a
good kind of tense; the type where he wants something reallybadly but he’s
holding back because he was told to.
Cas moans loudly, to the point that Jimmy and Dean both produce their own
groans of pleasure simultaneously. It’s obvious Cas is stuck between wanting to
continue sucking face with Jimmy or to suck Dean’s cock, although it becomes
apparent the latter wins when Dean begins languidly stroking himself. He feels
like being a little tease, so he gathers some pre-cum onto his fingertips and
walks over to Castiel and Jimmy. He places the slick fingers to Cas’s lips and
Jimmy commands in a low voice, “Don’t lick it.” Cas whimpers in his throat as
Dean begins to spread the pre-cum along the seam of his lips, occasionally
dipping the very tip of his fingers inside the boy’s mouth. Jimmy smirks and
pets Cas’s head. “Good boy Castiel,” he praises.
Dean steps away and says, “Suck it.”
He honestly doesn’t think he’s seen Cas move that fast before, but before he
knows it Castiel is on his knees in front of Dean. He goes to tentatively reach
a hand up to wrap around Dean, but Jimmy catches the hand before it can get to
its destination. “Hands behind your back, Cassie. I want to see him fuck your
face – roughen up your voice more than I already did today,” Jimmy coos as he
places Castiel’s hands behind his back, one hand holding them together at the
wrist.
Dean groans his approval (a man of very few words) before lining his aching
dick up against Castiel’s pretty pink lips. Again, he smears the pre-cum along
those sinful lips and watches as Cas simply blinks up at him, big blue eyes
conveying such innocence. It’s enough to have Dean forcefully thrust into that
warm mouth, moaning a stream of curses as he feels himself hit the back of
Castiel’s throat without resistance. He learned awhile back that Jimmy made
sure Castiel repressed his gag reflex anytime he’s sucking cock. So far it
hasn’t failed.
Dean reaches a hand out to grab Castiel’s dark hair as he thrusts – in and out
in and out. It feels so goddamn amazing; that throat and mouth working in
tandem to bring Dean closer and closer to the brink. And Castiel, the damn
cockslut that he is, makes these noisesthat should be illegal because he’s
having such a wonderful time sucking Dean’s cock – like all he lives for is to
be at Dean’s knees in this position. It’s so unbelievably hot.
The sensations running through his body are overwhelming, and before he knows
it, he’s feeling his orgasm rapidly approach. With a tug at Cas’s hair, the boy
retracts just as Dean’s orgasm hits. He watches in awe as his cum shoots out of
his cock to land in sticky white spurts all over Castiel’s face. He distantly
hears Jimmy saying “fuck” repeatedly. Castiel blinks some of it out of his eyes
and Dean gasps when he sees some of it sticking to those long lashes.
“Oh my God,” Jimmy breathes, turning Cas’s face towards his as he begins to
lick off Dean’s cum. Castiel is shaking with need no doubt as Jimmy takes his
time making sure he licks off every drop.
When Jimmy’s done, he smacks Castiel on the ass and says sharply, “Get on the
bed cumslut.” Castiel obeys and, apparently, this is slightly rehearsed because
Cas is automatically on his hands and knees, ass up in the air presented to all
who want to gaze upon it. And Jimmy and Dean are sure eating up their fill.
Jimmy strips until he’s completely naked and walks over to Dean. “I’m sorry;
I’ve been practically ignoring you this whole time. Will you forgive me?” This
is where Jimmy truly amazes Dean. The way the dominant act drops in a
nanosecond and submission appears. His eyes go wide (so similar to Castiel’s)
and he bites his bottom lip like he was just caught with his hand inside the
cookie jar. Dean merely smiles and brings Jimmy in for a soft kiss, one that
causes Jimmy to exhale a small gasp of breath.
“You are forgiven,” Dean assures, thumb caressing the boy’s cheekbone in a fond
gesture. Jimmy nods before heading back over to a waiting and slightly
desperate Cas. Dean follows, discarding the jeans and shorts. Cas doesn’t move
or say a word as his twin knee walks until he’s behind him. He rubs a hand up
and down his back in a way to be calming while Dean brings Cas’s face up to
kiss him. This kiss shared between the two isn’t chaste like the one he shared
with Jimmy; this one is deep and passionate, full of tongue and saliva that
makes it gloriously messy.
“Mmm, yeah, abuse his mouth Dean. I want him to not be able to walk or speak
for days.”
Dean presses his fingers around Castiel’s neck and pushes, effectively cutting
off Cas’s air circulation. Cas gasps what air he can pull in while Dean
continues to ravage his mouth. Dean lets off after a few moments and smirks
when Castiel inhales sharply. Jimmy tugs at Cas’s ridiculously hard cock to get
his attention. “I want you to suck my cock while Dean fingers you open. Would
you like that little brother? Being stuffed from both sides and feeling totally
debauched?”
Cas whimpers and nods, fingers digging heavily into the bed sheets below. His
breaths are short and fast and a pretty blush is spreading from his face down
to his chest. Dean didn’t believe he could be any luckier having these two boys
in his life. It’s actually quite funny how the two differ in the bedroom and in
the real world. Cas is a bit nerdy and a lot sarcastic. Jimmy is actually very
soft-spoken and family-oriented, wanting to have a bunch of kids someday and to
settle down. The two tend to be polar opposites personality-wise, but in the
bedroom they connect better than most sexually intimate couples. Dean really
does count his lucky stars.
He’s snapped out of his reverie by Jimmy grabbing him by the back of his neck
and pulling him for a sloppy kiss, one that causes Dean’s dick to twitch, but
not quite there yet to get it up again. He smiles at Dean fondly before gently
pushing him, and Dean finds himself eye level with Cas’s pretty hole. Dean
smiles wickedly before pointing his tongue and slowly allowing it to penetrate
Cas. The twin keens at the sensation and nearly rips the sheets with how much
his nails are biting into the fabric.
Jimmy laughs and brings Cas’s head back up into position so he can thrust his
cock into his twin brother’s mouth. Without hesitation, Cas begins to bob his
head along the shaft and nip at the cockhead every few sucks. Jimmy hisses and
grasps Cas’s hair in warning.
Meanwhile, Dean has got his face buried in Cas’s ass, licking at the puckered
entrance like it’s a goddamn lollipop or something. God Cas has such a pretty
ass. Jimmy too. He palms the globes of his ass and even goes so far as to slap
the cheeks a couple of times, causing Cas to whine and hum around Jimmy’s cock.
Jimmy makes an appreciative noise and tells Dean to do it again. Dean pulls
away to land a harder slap to Cas’s ass. The result sends Cas’s mouth further
onto the twin’s dick and another loud moan from Jimmy. Dean is so glad he’s
finally hard again. With a last few licks and sucking kisses, Dean motions for
Jimmy to retrieve the lube. Without dislodging Cas, Jimmy finds the tube and
tosses it to Dean, who catches it easily. He pops the cap, the sound causing
Cas to moan wantonly and push his hips back and up in invitation for Dean.
Because he feels like it, Dean smacks Cas’s rear once more, a tad harder than
the others, and smirks at the response it gets from both of them. The handprint
on the boy’s ass is pretty and red, just the way Dean likes seeing him.
“He really does like being smacked around huh Dean? Such a good boy for us,”
Jimmy comments in a pondering tone, practically petting Castiel on the head as
he continues to suck on Jimmy’s length. Dean hums and says, “He sure does. When
am I going to be able to smack you around a little bit, Jimmy? That mouth of
yours is going to earn you a very thorough punishment someday.”
Jimmy meets Dean’s heated stare and flushes immediately at the insinuation.
“I…I…um…”
Dean merely laughs and says comfortingly, “Don’t think too hard on it, babe.
We’ll work on it.”
Jimmy may be a switch but he definitely is more comfortable being dominant. Not
that he won’t be submissive, it’s just that he has a bit harder time actually
allowing Dean to reallytreat him like a sub. He can bat his pretty eyelashes at
Dean and speak softly and make himself appear smaller (dear lord help him), but
the actual act is still something they’re working on. Dean doesn’t mind that
it’s kind of a work in progress. He’s been growing very fond of the twins for
quite some time now.
Without any more distractions, Dean quickly lubes up his cock, foregoing
working Castiel open on his fingers because he’s bordering on desperation at
this point. And he knows his precious boy can take it; he’s had a lot of
practice. Castiel groans loudly as Dean breaches him, causing Jimmy to hiss
loudly and pull Castiel off. “Not yet. I don’t want to come yet.” The twin
whines his distress and pushes back sharply against Dean, making their hips
meet together.
Dean rubs Castiel’s sweaty lower back before saying in a low tone, “I want you
to work yourself on my cock, Cas. I want you to bounce on it like the cockslut
you are.”
“I-I’m your cockslut. Always a cockslut for you guys,” Cas whispers, biting his
lip as he uses his hips to push and pull off of Dean. He’s on his hands and
knees still and using any leverage at his disposal to make it happen. To make
Dean happy. And Dean is very veryhappy, if the grunts and gasps are anything to
go by.
“So goddam tight, Cas. Always so tight for me. Tight like you’re still a
virgin. Fuck!”
The closer Dean gets the more filthy words that spew from his mouth. Jimmy is
slowly stripping his cock and rubbing any skin he can touch on his twin,
causing sparks and goosebumps to appear along Castiel’s body. The room stinks
of sex and male pheromones, and it’s driving the three men a little bit crazy,
minds hazy with the ecstasy racking their beings.
“Jimmy,” Dean breathes, stopping Cas’s movements as he begins to thrust on his
own. “I’m gonna shoot on his back, okay? And I want you to come on his face and
his hair. Can you do that? I want him covered in our cum so he knows who he
belongs to.”
Jimmy nods and then address’s Castiel. “Who do you belong to, Cassie?” With the
hand not jacking himself, Jimmy pulls Cas’s face up so he can look his brother
in the face. Cas swallows and pants out, “You two. Only you two.”
“Good boy,” Dean and Jimmy say in unison.
A few thrusts later sees Dean pulling out hastily and shooting shot after shot
of cum across Cas’s back and ass; the white strips are thick and in large
quantity. Dean exhales out his orgasm, already entering into that post-orgasm
bliss that is so very bittersweet. He trails one finger gently through the
mess, putting a little bit of extra pressure on the skin to essentially mark
Cas. So mesmerized by his cum all over Cas’s back, Dean just barely looks up to
catch Jimmy’s orgasm. The great thing about sleeping with twins? Their orgasm
faces are completely identical, and it’s usually double the amazement of
watching the boys come apart. Jimmy’s head is thrown back and his hand is
working fast, almost in a blurring motion, over his cock, and when he shoots,
Dean inhales a gasp. Jimmy moans, and his release ends up all overCastiel – in
his hair and on his face. Dean barely registers hearing Cas whimper at the
sudden onslaught of hot cum all over his taught body, so enraptured by the
beautiful boy in front of him coming apart.
When Jimmy is spent and entering post-orgasm, he too runs a finger through all
the mess and smiling softly to himself. Cas whimpers beneath them, hips
undulating in a desperate plea for his own orgasm. They ponder Cas for a
moment, wondering if he deserves to come yet or if they should continue and
tease him at the brink. Today, Dean is feeling a bit gift-giving and waves
Jimmy away, saying without words that he’s going to handle this.
Not wanting to mess up their work, Dean instructs Cas to get to his full height
on his hands and knees before lying down on his back under Cas, face directly
in view of Cas’s dripping cock. Dean smiles when he feels many drops of pre-cum
land on his face. Grabbing Cas’s thighs for a bit of leverage, Dean cranes his
neck up to pull Cas into his mouth. Cas practically yells at finally getting
attention and nearly collapses at the onslaught of pleasure, but Jimmy holds
him up and stifles his moans with kisses.
Dean lets go of Cas’s erection and growls out, “Don’t Jimmy. I want to hear his
pretty noises.”
Jimmy relents with a disapproving grunt and one last long smack of lips. Dean
wraps his lips around the head of Cas’s cock once more, bobbing his head up and
down as much as he can given the awkward position. Cas is panting and probably
drooling judging by the sounds he’s making. It doesn’t take him long to finally
come, seizing up all over and crying out at the top of his lungs. Dean moans
around the mouthful of cock in his mouth and relishes the warm rush of cum that
enters his mouth. As he begins to swallow, he hears Jimmy say in a rush, “Don’t
swallow yet!”
When Dean is positive Cas is spent, he lets the twin’s softening cock slip out
of his mouth. He chuckles low in his throat when Cas falls over onto his side
with a decisive grunt and a long exhale of air. Dean sits up and turns to Jimmy
with a raised eyebrow since his mouth is full of cum at the moment. Jimmy shyly
gestures for Dean to scoot over. Dean catches on pretty quickly when Jimmy
makes to kiss him, and Dean dutifully opens his mouth and lets some of the cum
mixed with spit leave his mouth to fall into Jimmy’s. They share a heated kiss
as Castiel’s cum swirls between their mouths. When they swallow, they smirk at
each other and then look at Cas.
“Don’t evermake me wait that long to come you assholes,” he complains, reaching
up a hand to pull at some of the drying cum on his face. “I need a shower,” he
decides. He purposely sways his hips and wiggles his ass in invitation as he
makes his way over to the exit of the bedroom.
“You two wanna join me?” he asks saucily.
Dean doesn’t think he ever got out of bed faster than he did then. Jimmy is
right behind him, and with a few laughs and teasing touches, they all end up
piled in the adjacent bathroom.
When Gabriel comes home later, he’s met with the sight of his brothers and one
Dean Winchester all cuddled up on the couch asleep, The Matrixplaying on the
television. Gabriel shakes his head fondly and snorts to himself before digging
into his pants pocket for his phone. He quickly pulls up the camera on it and
snaps a picture of the trio together on the couch. Yeah, he’s definitely got
great blackmail material now. 
End Notes
     I feel so shitty for using Chris Brown lyrics but oh my god it works
     out soooo well for this story asdfkjgkfld. Anyway, hope you guys
     enjoyed. This is my first time writing threesome sex and it was quite
     a challenge. I have such a kink for Dean/Jimmy/Cas and I don't know
     why. Maybe because there's two Cas's? Also that and there really
     isn't enough Dean/Jimmy/Cas fic out there in my opinion. Kudos and
     comments are always appreciated. They make me a better writer~.
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