In the world of firsts, Crowley took a lot of Castiël's. Dean took a lot of others, but purely out of necessity. Starting as early as thirteen years old.

Castiël was thirteen, when Crowley gave him his first tug from a cigarette.

Dean held him steady as he puked afterwards.

At fifteen, Crowley talked Cas into helping him down the bottle of Craig he had lifted somewhere.

Dean nursed his first hangover the day after.

At sixteen Crowley gave Cas his first kiss.

Dean eased his worries wether that meant he was gay or not, and if it was bad if he was.

Seventeen, Crowley convinced Cas to ditch class.

Dean covered for him and helped him study for the test he missed.

Cas was barely eighteen when Crowley offered him a hit on the blunt he was smoking.

Dean sat with Cas as the bad trip he got had him screaming in fear at the monsters crawling out the walls.

Still eighteen, Crowley slipped Cas some XTC in his drink at a party.

Dean cooled him down and raced him to hospital to have his stomach pumped.

When Cas turned nineteen, Crowley picked his cherry, as a birthdaygift.

Dean picked up the shattered pieces of Cas' life and selfesteem, not complaining when Cas didn't want to press charges.

At twenty, Crowley told Cas snorting cocain was nothing bad.

Dean spent all night convincing Cas that he was not invincible and he shouldn't jump off the roof.

Twenty-one years old, Cas first heard Crowley say he was a worthless excuse for a human being.

Dean kept preassure on his wrists while Sam drove the Impala to the nearest hospital.

At twenty-two Crowley was the first to cheat on Cas.

Dean hugged him, told him he was better off without the limey bastard, cheered him up and kept his mouth shut when Crowley convinced Cas it meant nothing.

Cas was twenty-three, when Crowley beat him because he was just so useless.

Dean iced the bruises, and put gauze over the cuts Cas had slit in his legs, trying to feel something.

Just a few months after that, Crowley yells that Cas is the worst lay ever, and that he was embarrased to even be near him.

Dean was the first at the hospital after Cas crashed into a tree, drunk driving.

At twenty-four, Crowley was the first to walk out on Cas.

Dean was the first to find him and cry over him as he hugged his body.