AN: I'm just going to lump the warnings together for the whole story. Drug use/abuse, alcohol use/abuse, strong language, gang activity, violence, mild sexual themes.

Castiel woke up with a stiff neck and a sore back on a very uncomfortable mattress. He sat up and swung his feet over the edge to place them flat on the floor which made his stomach churn at the movement. His dark brown hair always stuck up at weird angles when he woke up so he raised a hand to smooth it out.

His left hand came up with it.

Castiel groggily opened his eyes and found his hands in handcuffs. Shit, he thought as he slowly started to remember why he was in a tiny jail cell.

"Oh good, you're up," Castiel heard someone say. It was the black cop that had helped arrest Castiel last night. He was standing outside of the cell with crossed arms and a smug smile. His name was maybe Henderson or Henricks or something, Castiel couldn't recall. It was hard to remember anything with a pounding headache to accompany his hangover.

Castiel squinted up at the officer. "Can I go yet?"

"Nope. You're going to tell my partner and I what happened last night."

Castiel groaned and closed his eyes again. He could hear the door to his cell being opened and then he was pulled roughly to his feet which did no favors for his uneasy stomach.

The officer, whose name still escaped Castiel, led him to an interrogation room. Castiel sat down before he realized there was another cop already in the room. She was tall with very short brown hair and smiling at Castiel. Her smile was kind, unlike the officer who dragged him in here.

Was she there last night? Castiel couldn't remember.

"Castiel, why don't you tell us what happened last night?" she asked. Castiel read her nametag on her blue uniform as "Mills."

"Officer Mills," Castiel started, rubbing his temples with both hands, "can I have some water, please?" She looked at the cop that brought him into the room and nodded. He left.

"Thanks," Castiel said.

"Not a problem," she answered. She had a file in front of her on the table and opened it. "So, this isn't the first time you've been in trouble, right?"

Castiel just shook his head. The door opened and the other guy was back. Castiel nodded his thanks before chugging the whole cup.

"Now," Officer Mills continued, "Officer Henriksen and I don't think you were the one responsible for last night."

Castiel just raised his eyebrows.

"We think this was your brother's doing but he got away before we could catch him," Henriksen said, sitting next to Mills across from Castiel, who didn't say anything.

"Was he behind the other stuff on your sheet, too?" Henriksen said. "You don't exactly look a stoner or a thief."

"You don't know anything about me," Castiel said icily, meeting Henriksen's eyes with a glare across the table.

"Look, we're trying to help," Mills said, breaking the tension. Castiel shifted his eyes over and eased up on the glare.

"I know, but what can you do? I stole that car last night, I shoplifted and the weed was mine. My brother had nothing to do with it, any of it," Castiel argued.

"I don't think someone who attended such a prestigious high school, college prep school really, wouldn't be so stupid," Henriksen said.

"Key word being 'attended.' It might not be in your little file, but they kicked me out. They didn't want someone who went to juvie for drugs and fighting."

"Fighting? What happened?" Officer Mills asked.

"Someone at school was being a dick," Castiel shrugged. Henriksen and Mills shared a look.

"You know, normally grand theft auto would scare people. It's a considerable amount of jail time. Especially for someone with a record," Henriksen pointed out.

Castiel swallowed and looked down at his handcuffed hands in his lap. He was scared, sure. But that wouldn't help. Being reasonable and figuring something out would help here.

"We know you're smart and you seem like a good guy," Mills said and Castiel scoffed to himself. He wouldn't say the same thing. "We might have a way to help you if you help us."

"How would you like to be an informant?" Henriksen asked. Castiel looked up, confused.

"We're working on getting information on a gang. They're small time, not a lot of guys, and they just sell weed. However, we're trying to being some of them in and we could use you," Mills explained.

"You want me to join and snitch on a gang?" Castiel asked doubtfully. "Doesn't that sound a little dangerous?"

"We'll keep you safe," Mills reassured him. "We just want you to have another option besides jail. You're only twenty and like I said, we want to help."

Castiel considered it for a moment. It wouldn't be fair for him to go to jail because stealing the car was his brother, Gabriel's, idea. He was lying to protect him. Again. Castiel had covered for Gabriel for the shoplifting and the weed was thrown to him because Gabriel couldn't get caught with it again. Family always came first but that didn't mean Castiel needed to go to jail and they still couldn't prove Gabriel had anything to do with last night.

"Fine," Castiel agreed. "What do I have to do?"

Castiel finally walked through the front door of his apartment after his rough night, and morning, and was really not in the mood to have to deal with Gabriel.

"Castiel, man, where have you been?" Gabriel asked, pulling him into a hug that Castiel reluctantly returned.

"Covering for you. Again," Castiel said as he broke the hug.

"Hey, I'm sorry. I couldn't get caught doing something stupid. You know that I'm on probation," Gabriel stated.

"Yeah, well you're lucky I'm not. Or going to jail," Castiel said as harshly as possible.

Gabriel didn't say anything.

"I'm going to bed. I didn't sleep very well in a jail cell last night," Castiel snapped.

He slammed his bedroom door shut leaving Gabriel standing alone, feeling guilty, in their living room.