Three Can Keep A Secret

Sam was eleven when Dean was kidnapped. The first time, that is.

It wasn't serious; just some wannabe-mobsters trying to make it big. They got Dean after a night out drinking with some people who'd pretend to be his friends. He was young and desperate back then.

They kept him in a small room with a bed, a TV and a round table. It wasn't much, it wasn't exciting and there were no big fights or wild chases, but Dean welcomed any variety in his life.
He knew that Bobby would send the money and some men to shoot those bastards up sooner or later anyway, and at least he got some vacation from that home schooling he wasn't exactly keen on.

He got bread and water, and the guys never showed their faces. That was always a good sign, Dean knew. They didn't talk either.
He got a lot of me-time, too. During the twelve days they kept him there, he got used to jerking off without any magazines. He also found out that there might be second guy sneaking into his fantasies from time to time. He couldn't care less; there was no use for romance in his life anyway.

Sometimes he’d push his hands and ear against the wall to feel and hear for any sign of civilization; A big street possibly or just one single car.
He probably was too deep down though, because he never did.

A lot of the time he also thought about Sam, and his biological father, John. Somewhere on the road he realized that John wasn't the saint of a father Dean always kept the memory of, and that Bobby wasn't so much of a devil for taking the boys away from him.
That was the slowly kind of sinking realization that formed over days or months or years, not the startling ones that hit you like a feminist in the balls.

Not knowing whether his father was alive or dead sucked, yes, but he wouldn't dare showing his face in front of him anymore either way.

It was his twelfth day when a young guy came in. A little older than Dean, dressed in a suit with a vest and lacking the jacket. His sleeves were rolled up, his black hair was a figuratively everywhere and his stubble only added to his messy appearance.

Dean was lying on the bed, staring at the ceiling with his hands behind his head when the guy sternly said, "Follow me."

Dean merely pushed himself off onto his elbows and raised an eyebrow.

"What, now you're gonna shoot me? Took your sweet time, huh? Singer won't be happy at hearing you amateurs tried to kill me."

At the mention of Bobby's surname, the man cringed. He ran a hand through his hair and sighed.

"Dean Winchester, I am not here to take your life. Follow me, I beg you."

Dean sighed, took his time getting off the creaky bed and followed the man out the door.

Maybe he was bait. Maybe the guy was supposed to get Dean out of here and get dramatically shot while doing so. That would explain the beginner's level this whole bailout was running on.

They turned right and walked quickly down the bare and ugly hallway. At the end, there was an elevator and some stairs.

The guy looked to his side, down to Dean (yeah, so Dean wasn't as tall as him, whatever) and asked amused, "Stairs or elevator?"
Dean pondered the functionality of stairs against the badassery of elevator and decided on stairs.

"All right," the guy merely replied and began racing up the stairs as soon as Dean informed him of his decision. Dean had trouble keeping up and almost fell a few times. Jesus, how did this guy get so fast? Maybe he wasn't so much of a newbie after all.

As they got down to the lobby, Dean noticed a few guys loitering there with dubious sunglasses, and because his knight in the shining armor kept running, Dean did the same.
Good decision, as it turned out when the men started screaming blue fucking murder and made their best to catch up to them when the guy and Dean sprinted out of the building. They were on a seriously huge avenue with lots of cars racing by and people shoving themselves from A to B.
By now, Dean’s throat hurt from heaving so much. He barely got any exercise down there after all.

Dean was still a little behind and saw the guy search for something in his pocket. He got a car key out, pressed it and a dark blue van beeped.

After seeing him get into the driver's seat, Dean swung into the passenger's seat and they were off.
He caught his breath and watched the city night lights for the sake of the sake of their beauty before managing a, "Why'd Singer just sent one?"

That's when the guy in the driver's seat chuckled quietly. "What makes you think your father has sent me?"

Shit. "From smoke to smother, eh?" Dean knew he was up to his chest in steaming crap now and his heart began racing again.

"Calm yourself though. I am going to return you to your family."

"Oh, sure, since you're such a sweet angel. What are you going to do until then, cut off my balls and ship them to Indonesia?"

The guy frowned. "No. Why would I do that?" There was a pause of eyebrow contracting and he continued, "My family has sent me. And besides, good things do happen, Dean Winchester."

Not to me, Dean couldn't help but think. But the rest of the drive, he stayed quiet.

When they got to the Singers' mansion, Castiel, as everyone seemed to call him, returned Dean and was soon officially employed as his personal body guard, unofficially taken in as his brother. He never spoke of his own family again after that.