Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/1462279.
  Rating:
      Explicit
  Archive Warning:
      Choose_Not_To_Use_Archive_Warnings, Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Castiel/Jimmy_Novak/Dean_Winchester, Castiel/Jimmy_Novak
  Character:
      Dean_Winchester, Castiel, Jimmy_Novak, Naomi_(Supernatural)
  Additional Tags:
      Twincest, Underage_Sex, Castiel_and_Jimmy_seduce_Dean, Dirty_Talk, Panty
      Kink, Older_Dean, Bottom!Cas, bottom!jimmy, sorta_-_Freeform, top!dean
  Stats:
      Published: 2014-04-14 Words: 2113
****** The Devil(s) Wear Panties ******
by orphan_account
He shouldn't have been doing this, he really shouldn't have been doing this.
For one thing, he was twenty-six and the twins weren't eighteen yet. They were
seventeen (eighteen soon though, they kept reminding him) and they were both
fucking ridiculous. The Novak's had no idea that their sons were cocksluts that
only wanted their older neighbor's cock more than they wanted an iPad for
Christmas. 
Dean had promised himself not to let Naomi Novak bully him into "babysitting"
her sons again; why the fuck did seventeen year old kids need babysitting
anyway? Of course, the Novaks were ridiculously strict, so Dean had a feeling
he knew why the twins were so damn eager and slutty. 
The first time Dean had watched them, they had come over to his apartment and
everything had been relatively normal for a few hours. They boys had sat and
argued over what to watch on the TV since Dean had more channels than they did
at home apparently. Dean had been making lunch for them. 
In the middle of making grilled cheese, Castiel had popped up next to him,
which almost sent the sandwich flying. "Cas! Don't do that-" 
"Sorry Dean," Castiel apologized with a weak smile. Jimmy appeared on his other
side then and Dean should have smelled his end right then and there. "He's
cute, isn't he Jimmy?" 
Jimmy nodded. "Yeah. He is." 
Castiel grinned and reached to slide his hand up under the hem of Dean's shirt.
Dean jumped and turned to look at him. "Whoa-what are you doin'?" 
Castiel smiled. "Nothing." 
"Yeah, nothing my ass," Dean snapped in reply. "Cas-"
Castiel winked at Jimmy, and stepped in close to nuzzle Dean instead. "I want
him to fuck us both," Castiel mused to his twin out loud, which made Dean
sputter. 
"Oh yes, I bet he's uncut," Jimmy purred in turn. 
Dean had to push them both back gently. "Guys, you're not legal, I'm gonna be
twenty-seven for God's sake. In January. We can't-" 
"But why not?" Castiel pouted. Jimmy walked over and slid his tongue into
Castiel's mouth, which stopped Dean's protests in his throat, leaving him
speechless. 
"Yeah? Why not?" Jimmy echoed his twin before kissing him again. 
Dean felt like his legs were going to give out. "Stop-guys-seriously. No. No." 
The twins both pouted at him but thankfully, that had ended his almost trip to
jail. He also promised to never babysit the twins again, and he didn't for a
long time. However, that did not stop them from teasing him mercilessly. 
Dean had been cleaning up his tiny backyard from the small party he had had one
July evening. When he had accidentally glanced over at the Novak's, he had been
able to see Jimmy and Castiel near their bedroom window; the blinds were open
and the twins were wearing nothing but tiny panties and grinding together.
He knew that they knew he was watching, so Dean had hurried inside. 
He had also jerked it so hard that night, Dean was surprised he hadn't yanked
his dick right off of his body. 
A few weeks had gone by since that second encounter without incident and Dean
was certain that he had rid himself of the annoying (hot as fuck) twins, who
were hell bent on getting him in bed. Around lunch time, Dean decided to work
on Baby outside, which he regretted in the end. Every time he glanced up, he
could catch glimpses of Castiel and Jimmy stretched out on their front lawn in
nothing but tiny shorts, massaging each other with tanning oil as they laid out
in the sun. 
Dean almost choked when he saw them smile at him and share a kiss. Once again,
Dean had spent the better half of the evening jerking off to the twins. As long
as the fantasies stayed in his head, Dean wasn't going to complain. 
An exceptionally hot night in August found Naomi on his doorstep, her boys in
tow, looking guilty. "Hello Dean, I apologize for bothering you. I know it's so
last minute, but my husband and I need to go out of town to attend to my
brother, he's very sick. Could I possibly leave Castiel and Jimmy with you for
the weekend?" 
Dean stared at her blankly, trying not to panic on the outside. A whole weekend
with the twins? Fuck-
He should have said no. He should have said hell no, but what left his mouth
was a, "Sure Mrs. Novak, they're more than welcome to stay." 
"Great. Thank you so much." Naomi smiled and kissed her boys on the noses
before leaving them on Dean's doorstep. 
Castiel and Jimmy waved to their mother as she drove away and then they were
turning back to look at him with equally terrifying smiles. "Can we come in?" 
Dean rolled his eyes and stepped aside to allow them entrance. "No funny
business you two," he snapped as soon as he shut the door, glad to keep the
cool air inside. 
"Of course," Castiel replied with a coy smile. "We promise to be good, Dean." 
"Yeah you better," Dean muttered before walking over to continue watching the
game that had been on the TV. Honestly, he should have just locked them in a
bathroom with a bowl of water because soon he had two horny teenage boys
hanging on either side of his chair, running their fingers through his hair,
and trying to kiss him. "Guys-stop-" 
Castiel turned his face, kissing him eagerly, while Jimmy worked his fly open.
They were systematic predators, calculating their every move; it was like
watching lions hunt down a gazelle who had already been weakened by previous
attempts. Dean groaned when he felt Jimmy (or maybe it was Cas, he wasn't sure
anymore) wrap a hand around his half hard cock. 
"Look Cas, he's already half hard," Jimmy purred. "I told you he wanted us." 
Castiel smiled happily, as if that news had made his entire day. "Good. I was
growing worried." Castiel's already pouty lips, formed into a sad little puppy
pout and Dean felt his cock stir to its full hardened length. 
If he was going to do this, he was just going to fucking do it. "You two aren't
behaving," he told them firmly. "You're pissing me off." 
Castiel gave him a sad alarmed face. "What can we do to make you not mad at
us?" 
Dean smirked as the boys turned puppy eyes on him; they were so damn eager for
it, it was like all of his fantasies come true in one go. "Take your clothes
off. Slowly." 
Castiel nodded and hopped to his feet, pulling Jimmy up with him. The twins
eagerly made out while they stripped their clothes away, all the way down to
their similar panties; Jimmy had a pair of pink ones on, they had little white
bows on the hips and polka dots patterned all over. Castiel had on a blue pair
with white lace trim and white hearts dappling the cotton. 
God, they were the naughtiest boys he had ever met. 
"Stop," Dean told them before they could get the panties off. "Keep those on. I
like 'em." 
The twins smiled and slid to their knees to wait instruction. 
"You're both sluts, aren't you?" he asked them and they nodded. "Bet you both
want my cock, bet you both would argue over who got it first." He stood and
kicked his jeans and boxers away, holding his base, showing them that yes, he
was uncut. 
"I want it first," Jimmy chimed in immediately. 
"No me," Castiel snapped. 
Dean chuckled. "You'll both get a turn. Relax." He flicked his wrist a few
times, stroking his entire length, and pulling his foreskin back with a soft
groan. It was more for them than it was him, and he smiled when the twins
stared wide eyed. 
Castiel opened his mouth so Dean teased his head against his bottom lip, until
Jimmy did the same, and he dragged it between them both. They were eagerly
lapping and licking at his slit, so Dean stilled and allowed them to lap and
lick up his length, each twin picking a side of his cock to suck, nibble, and
lick. 
Dean smiled, petting their hair each, praising them both for being so damn
good. And they were; it was like their mouths had been made to give head.
"You're both so good," he muttered, which made the twins smile happily. They
liked praise. 
"Dean, we're horny," Castiel whimpered. 
Dean flicked his eyes over to Jimmy who nodded in agreement. "Yeah? You want
cock?" 
"Yes," Jimmy said. This time, Castiel nodded. 
"Okay. Okay. Lemme see those cute asses," Dean said before sinking back into
the chair. 
Both twins pulled their panties off and turned around, spreading their cheeks
for him to see how pink, puckered, and gorgeous they both were. "Jesus," he
whispered. "You two virgins?" 
That brought a laugh and Castiel winked. "No," they said in unison. 
What a stupid question, Dean realized. Of course they weren't virgins, they had
been trying to bag him for the better of the damn summer. He shook his head and
stroked his length again. Choosing between the two of them was going to be
ridiculously difficult. 
"We brought lube though," Jimmy said before walking over to his bag to pull out
a bottle, uncapping the lid and smearing some on his fingers. Then those
fingers went directly up Castiel's hole and Dean stared at how greedy that hole
was to take three fingers. 
Castiel whimpered and bent over, his hands wrapped around his ankles. They were
fucking flexible too?
"Jimmy," Castiel moaned. 
Jimmy smiled and finger Castiel open, rubbing his prostate. "He's going to come
soon, Cas is bad at lasting." 
"Is he?" Dean purred, his fingers rubbing his lips as he watched the live porn
show. "Well, c'mere Cas." He patted his lap and with Jimmy's help, they had
Castiel settled on Dean's dick. Dean shuddered and groaned at how tight
Castiel's young ass felt around his cock; it was almost too much. 
"Son of a bitch," he cursed before starting to pump his hips, one hand wrapped
around Castiel's hip, which was like fucking cut glass, and the other gripping
the arm of the chair for balance. Jimmy slid in between Dean's and Castiel's
legs and was quick to wrap his tight lips around Castiel's length, humming and
sucking. 
Dean bit into Cas' shoulder blade, fucking him hard and fast. "You like that
baby?" he panted. "You like that?" 
"yes-yes-" Castiel insisted brokenly, completely used between the two of them. 
"You gonna come in Jimmy's mouth? You big fucking slut." Dean kissed Cas' neck,
grinding deep against Cas' prostate. "Such a whore, Cas." 
"Yes," Castiel agreed immediately, shuddering. "I-I-I am-" He cried out as he
began to come, his body jerking and wracking on Dean's lap. 
Dean smiled, petting and rubbing Cas' back as he eased him through his orgasm.
"But such a good boy," he muttered into his skin. "Is Jimmy as good as you?" 
Jimmy swallowed Castiel's load down before easing up to straddle the arm of the
chair, showing Dean his hardened cock. "No, I'm bad." 
Dean smirked and wrapped an arm around Castiel's waist, easing him back against
his chest, while a lazy hand went to stroke Jimmy slowly. "I bet all this was
your idea, wasn't it Jimmy?" 
Jimmy nodded, rolling and rocking his hips. "Yes-yes it was-I told Cas it'd be
a good idea to fuck you-" 
Dean smirked and nuzzled Castiel's neck to let him know he wasn't forgotten
even as he paid most of his attention to his twin. "Oh I bet it was, I bet your
the brains of the operation. Aren't you Jimmy?" 
Jimmy whined and fucked himself into Dean's hand, his cock becoming wet with
precome. "Yes-yes-yes-" 
Dean smirked, unsure if Jimmy's canting was an admission or how good he felt.
"I love your cock Jimmy. It's so pretty," he praised the younger twin. "I can't
wait to fuck your hole too, baby." 
Jimmy shuddered and began to come thickly, coating Dean's hand. He whimpered
and nodded. "Please-" 
"Soon baby, soon. I promise." Dean offered his hand to Cas who was quick to
lick it clean. "So good Cas." 
Castiel smiled and then Jimmy was crawling half on Castiel's lap and half on
Dean's to cuddle. The twins were eagerly wrapping up in each other's arms and
Dean pet them both. 
He knew he shouldn't have had sex with them, but he was sure as hell going to
do it again...and again...and again....
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