Why Does It Have To Be (Wrong or Right)

Title: Why Does It Have To Be (Wrong Or Right)
Author: @samanddeaninpanties, ao3
Fic Link: [Ao3]
Art Link: [Ao3]
Rating: Explicit
Archive Warnings: none
Tags: AU, first time, angst, angst with a happy ending, teacher Sam, server Dean, tattoo artist Jimmy, tattoo artist Cas, d/s undertones, dom Cas, sub Dean, pain kink, ink kink, piercing kink, group sex, top Cas, top Benny, top Sam, bottom Dean, bottom Jimmy.
Pairings (other than D/C/J): Cas/Jimmy, Sam/Jimmy, Dean/Cas/Benny, Dean/Sam/Cas/Jimmy, Sam/Dean
Posting date: May 17th, 2017
Summary: When Sam and Dean enter a tattoo parlor on Sam’s birthday Dean’s drawn to Castiel, the grumpy owner, and his twin brother Jimmy. Right away he learns that Cas and Jimmy are in an incestuous relationship and the adjustment period is surprisingly easy.
After Dean, Cas, and Jimmy get together Jimmy drops a bombshell - he wants to bring a couple of friends into their bed for a night. The problem? None of them know anyone they trust outside of Benny and Sam. And Jimmy really, really, really wants Sam to fuck him.
Teaser:
Cas and Jimmy close up shop and Dean can’t stop looking at them. The way Jimmy laughs and slides his hand up Cas’s arm is… interesting.
“Hey, Sammy,” Dean says, clapping him on the back. “Ready to hit up a bar? We could stop by your place first and -”
“Nah, I think I’m just gonna take a cab home.”
Dean frowns. “No way! It’s your birthday, dude. That’s not happening.”
“I know you wanna fuck around,” Sam says, voice low. “I’ll just get in your way.”
“It’s your birthday. I wanna hang out with you, Sammy. Yeah, the twins are hot, but I can just grab their number, no big deal.”
“Too bad,” Sam says, stepping away from him. “I really just need to leave. Okay? I need some space.”
“At least let me take you home. Do you really want people seeing you when you’ve got come in your underwear? C’mon, man. Don’t be like this.”
Sam gives him a dirty look. “Goodbye, Dean.”
Then he stalks off.
Fuck.
How could he have screwed the night up already? It wasn’t even midnight!
“Hey, Dean. Are you all right?” Jimmy asks as he sidles up to him. “Why’d Sam leave? Thought it was his birthday.”
Dean runs a hand over his face. “I don’t really wanna talk about it if that’s okay with you.”
Jimmy nods. “I understand. Um, I know this is weird, but would you like to hang out?”
Dean bites his lip and presses closer to Jimmy. “I know just the place.”
Twenty minutes later they pick a booth at Denny’s - Dean takes one side and the twins are on the other. Jimmy drapes an arm over Cas’s shoulders and Cas tries to shrug him off but Jimmy keeps touching him until Cas sighs, giving into his brother. Dean orders a bacon cheeseburger, Cas gets a sampler platter and Jimmy chooses the bacon lover’s blt.
“Shit. You might like bacon more than I do,” Dean says with a laugh.
“He’d live off of it if I let him,” Cas says, shaking his head.
“That’s because bacon is amazing,” Jimmy says, tone serious.
Cas shrugs. “I prefer steak. A nice filet mignon. Maybe a prime rib. Bacon is fine. I also feel as though this conversation is useless. How about we talk about the obvious?”
“Which is?”
“You want Jimmy.”
Dean chokes on his water then licks his lips. “Yeah, maybe I do. So what?”
“What if I want you, too?”
“Uh.” Dean rubs at the back of his neck. “That could get complicated, but I’m sure we could work something out.”
“Before this goes any further there’s something you should know.”
“Oh no,” Dean teases. “That’s not very reassuring. You’re not serial killers are you?”
Cas snorts. “Hardly.”
Jimmy glances around Denny’s to make sure no one is eavesdropping and lowers his voice. “We fuck.”
“Come again?” Dean asks, because he could not have heard that right.
“My brother likes to hold me down and fuck me until I scream,” Jimmy says with a heated look.
Cas reaches out and steals some of Dean’s fries, eyes darker than Jimmy’s. “Can you handle that, Dean? Or are we wasting our time?”
