Dean Winchester was the apple of Bobby Singer's eye, they weren't blood related but he looked upon young Dean as a son and hired him to work at his company, not too long after Dean's parents died in a car accident.
The Young Winchester boy used his hard earned cash to put his younger brother Sam, through school and Bobby swore to always be there for both of them.
"Sit your ass down Winchester; I got a new job for you"
Bobby adjusted his trucker cap, it wasn't typical dress code for a company boss, but Bobby wasn't the typical kind of guy. He ran a company which specialised in hiring protectors and body guards, assigning them to appropriate jobs.
Dean had previously worked as security in clubs and bars, he always wanted to do something more important like protecting royalty or somebody famous, but Bobby was always wary of putting Dean on high risk jobs, mostly because of Sam and of course, Bobby wanted to see Dean in one piece at the end of the day.
Today was the day, everything was about to change for Dean Winchester.
"So a job…" Dean started, taking a seat opposite his elder.
"Yep…although I have to say, I'm not thrilled about offering it…but I don't have much choice." Bobby grumbled his words and let out a long sigh.
"Ooook, that doesn't sound good"
Dean looked uncomfortable, shifting in his seat and waiting to hear what this 'job' could hold for him.
Bobby took another deep sigh and looked Dean in the eye before continuing.
"I am assigning you to be a bodyguard for…shall I say…someone particularly famous and well known…"
Dean's face immediately lit up, a huge grin washing over his face and he excitedly sat up in his chair.
"Oh my god…this is awesome, are you serious? I have always wanted this chance…who is it Bobby? No wait don't tell me…is it…Ozzy Osbourne…"
Bobby screwed up his face, frowning at Dean's attempt to guess.
"Ok ok…not Ozzy…is it…Tom Cruise, no...How about…Britney Spears…Nah not her…oh my god…you're hiring me to look after Justin Bieber aren't you? Man that is low Bobby…what did I ever do to deserve this…"
The older man rolled his eyes at Dean and interrupted.
"Dean, would you shut the heck up for a second!"
He sat back in his chair immediately and rolled his eyes, at least having the decency to shoot a sheepish look in Bobby's direction.
"As I was sayin'…You are wrong by the way…on all of the above. This one is tricky, let's just say not many bodyguards have stuck around for long…he is reckless, quite a handful and it's fair to say he has a small case of the crazy…"
"You are assigning me to Charlie Sheen aren't you?" Dean stated dryly, wearing his best poker face.
Bobby rolled his eyes once more and Dean broke into a cheeky grin.
"No Dean, would you just listen. We need to assign a guard for this guy, his agent is insistent but nobody is willing to take him on. As much as I hate putting you forward for this, it could be high risk…but nobody else will take the job. I know you kid, I think you could do well here…I trust you and you could kick this guy into shape no problem."
Dean looked genuinely taken back by Bobby's comments, he really believed in him and this humbled Dean.
"Wow, thanks Bobby you won't regret this…I'll be careful I swear and I know I can do a good job."
"I know you can son." Bobby smiled a lopsided grin and nodded.
"So…who is this guy then?" Dean enquired, leaning forward and resting his elbows on the desk.
Dean's eyes went comically wide, his mouth dropped open slightly in shock and Bobby couldn't help but huff a laugh at the younger man's expression.
"THE Castiel Novak…as in lead singer of 'The Fallen Angels' Castiel Novak…"
"How many Castiel's do you know kid? Hardly a common name…yes him." Bobby mumbled, scrunching up his face.
The young Winchester flopped back in his chair, eyebrows knitting together in deep thought and shaking his head slowly.
"Wow…I've heard a lot about him, I mean I love his band…their music is epic but…man the things I've heard about that guy…when you said reckless you weren't kidding." Dean said, musing over the situation.
"You think you can handle it?" Bobby asked, raising one eyebrow.
Dean looked up towards Bobby, letting out a deep sigh and nodded his head, before letting out a big beaming smile.
"Bring it on"