Throughout their set, Dean's eyes meet with their manager's a few more times. As the final tune of the night begins, Dean smiles to himself, proud. The randomness of his choices for the afterparty is sure to hook each of them a good fuck. Well, except for Cas and Meg. They’re married to one another but that doesn't stop the wedded pair from participating in the activities. Hell, they have even let Dean accompany once or twice.

FLASHBACK

Meg Novak is a dirty, kinky slut who likes to watch and direct her husband as he sucks down the singer's dick. As Cas takes Dean down his throat, Dean's gaze is on the fingers of the band's keyboardist as she sinks them into her soaked pussy. 

"How's that big cock taste, Clarence?" Meg inquires, using Cas' given name. "I bet it feels good sliding down that hot throat, huh?" Cas moans his response around Dean's length, causing it to twitch and jump in his mouth. 

"Fuck Meg," Dean gripes. "You keep making him do that and I won't last long enough to ram this big cock in that tight ass!"

That shuts Meg up as she slides her cum-soaked fingers down to that very place. "You mean this one, big boy? Huh? What makes you think-" she is interrupted as the blonde, one of their few crew members Sam is fucking into, cries out from the other side of the  room, "-you get this? Huh, sweetcheeks?" She glances over at the door as a cacophony of moans erupts again. "Sammy, baby, sounds like you're fucking her good! Keep it up!" she yells with a chuckle.

Dean watches as Meg's middle finger circles her ass and then slowly slips in. "Oh, yea.  This ass is nice and tight for you buddy. Cas, get on the bed. Let me ride you."

Cas promptly takes his mouth off Dean and climbs onto the king-sized bed, falling back until he is prone in the middle. Dean watches as Meg saunters over and climbs up beside her husband. She throws a leg over his crotch and rubs her pussy up and down her husband's length, getting him prepared. As soon as she can, she lifts her hips and lets his tip notch at her entrance. "You watching or joining?" she asks Dean, not taking her eyes from her husband. Dean jumps into action, taking his place behind her between Cas's legs. He guides her hips as she sinks down on Cas' dick. Keeping his hands where they are, Dean helps as Meg begins bouncing on Cas until they get a nice rough rhythm and then he takes one hand away, wrapping it around his cock. Who knew watching a married couple fucking could be so intense,  Dean thinks to himself. He begins jerking off to the same pattern of Meg's bounces. After a few minutes, Meg leans over Cas' torso and looks at Dean over her shoulder, giving him a wink. Dean knows what that means; it's time for him to join. He crawls up behind Meg and pulls her asscheeks apart. From this view, he can see his friend's dick being swallowed by her wet heat. Dean groans at the sight and gathers saliva into his mouth. He bends down and spits right on Meg's hole and rubs it around with his thumb, making sure to lube it up good. Once satisfied, Dean guides his dick into her back hole and slowly enters. 

END OF FLASHBACK

That is also the same night Dean and Benny ended up high as kites with Dean sucking off his best friend. And the beginning of the after-concert debauchery that has only grown with time, now including others, not just the band members and crew.

Crowley MacLeod has always had his hands full with the musical acts he represents but the Winchester Sex Bombs are quickly becoming his kryptonite. 

He had discovered them about three years ago in some run-down dingy bar scene on the outskirts of Lawrence, Kansas. The group of five had potential so after one of their sets, he approached them and offered to get them out of the small-town scene and onto billboards and packed arenas but that promise had yet to come to fruition. He had gotten them a tour across the country but no national recognition yet and with the unflattering news reports and arrests they have accumulated, there weren’t any indications that it ever would. 

Although he has never prohibited their after-show shenanigans, he’s never prevented them either. He knows what goes on behind closed doors and all parties are consensual but it was the venues that complained and ended up calling the law. The latest escapade though is all Dean and Benny. They had been arrested for lewd behavior and indecent exposure. 

Crowley is livid when he gets the call at 4 a.m. but he decided to teach them a lesson and let them stay in jail. He only calls his lawyer at 9 a.m. when he awakes again. 

Now, here he is, sitting at a table with the other members of the band awaiting the arrival of the lead singer and the drummer, along with the lawyer. 

As soon as the familiar vehicle pulled into the parking lot, Crowley excuses himself and steps outside, passing the two remorseful bandmates.

Crowley can not stand the short, pompous man who represents the band but when he had chosen his cousin's firm, Chuck had appointed them Gabriel. Crowley wasn’t happy with the appointment as much as Gabriel was agitated with the assignment. Crowley and Gabriel have never gotten along, but with family sometimes you just have to grin and bear it.

“Fergus,” Gabriel greets the manager, using his given name. “We need to discuss the band’s extracurricular activities.” Crowley can tell from the tone of Gabriel’s voice the man is not happy with having to come to Windsor and work his magic to get the charges against his band repealed. 

“I know. I plan to,” the robust man replies. “As soon as we get bigger gigs than these backcountry, rundown bars, I’m going to have a talk with them.”

“You better do it before that or those bigger gigs aren’t going to be coming in,” Gabriel reminds him. “I can only do so much, Cousin. Word on the street is Winchester Sex Bombs are more trouble than they’re worth. So you better get a rein on your boys or there’ll be Hell to pay!”

“What are you talking about?” Crowley huffs as he looks at the man in front of him skeptically. 

“I mean, get a handle on them or I’m going to tell Dad to drop you as clients. We’ll quit defending them and then let’s see how long it takes before the tabloids crown them as the bad seed of the business.”

“This is the entertainment industry, Cousin,” Crowley sneers, as he hands over an unmarked envelope, payment for Gabe’s services. “Sex, booze, and rock and roll.”

“Well I have a little thing called integrity that I’d like to keep intact,” Gabriel replies, taking the envelope from Crowley’s hand. “Remember what I said. The family can only take so much.” 

And with that, Gabriel climbs into his vehicle and pulls away, leaving Crowley in the parking lot of the local diner. The manager looks through the window of the diner to see the five band members laughing and carrying on. He shakes his head as he heads inside to join them.