A/N: The story starts out on the bad side of New York and it's somewhere in season 4. Sam and Dean are in their twenties but Angels are still involved and will make an appearance in later chapters. Sam is not on demon blood and the apocalypse is still going but while Dean was in hell, Sam killed Lilith (Who in this story was not the last seal) but not before she let every single monster imaginable out of hell and purgatory. Sam closed the doors before the leviathan and any other monster could get out, now they're working on sending as many evil sons of bitches back as possible and trust me there's a lot. Sam is 24, Dean is 28, Anna is 5 and Castiel is 10.

A Big thanks to my friends Alana (for always encouraging me to keep writing) and DSCWin (for helping me with the title)

Castiel slips out of the sleeping bag he and his sister Anna shared. Looking around he saw chips of the wall scattered all over the room and bits of the ceiling covering most of the floor, while dirt covered the rest. The walls were rotten and you could tell no one lived in the apartment for a long time. To top it all off it was cold, wet, and they couldn't start a fire for fear of being caught. Castiel looked down at Anna who was sound asleep. He wished he could let her go and be alright, she would have a home and a warm bed to go to every night and not some dead end street or apartment building, worrying about him or when they would eat. But truth is he wouldn't be alright, in fact he'd be far from it. As if on cue Anna rolled over on her side and wrapped her small hand around two of his fingers. Castiel smiled down at her, she always had a way of knowing when something was bothering him. How could he ever think of leaving her? She needed him, now more than ever. They needed each other. It was as simple as that. Slowly Castiel shook Anna's shoulder. She whined a little sitting up and rubbing her eyes before looking at him in confusion.

"What is it? Someth'n wrong?" She asked him.

"Well, if you want something to eat, then we better get going." He said with a smirk, standing up. Anna's mouth forms a little 'o' as she understands, scrambling out of the sleeping bag and after folding it she walks over to her small bag that held two pairs of clothes to change into and her sneakers with holes in them. Slipping on the shoes she ran over to Castiel and grabbed his hand before walking out the door and closing it as quietly as they could.

A few feet away from the abandoned apartment building behind a dumpster Castiel makes Anna wait where it's safe.

"Do you remember what we went over Anna?" Castiel asked looking her in the eyes, his voice going low making sure she knows he means business. Nodding she looks at him worry clear on her face.

"If you not back in twenty minutes I go back to the apartment and-" She trailed off looking away. Castiel grabbed her shoulders and made her look at him, then smiled.

"Hey, nothing's going to happen. I've done this before and always come back fine. This is for just in case and if I don't come back, it means I had to take a detour and will meet you later." he said trying to reassure her. He has in fact done this before and- even though he will never admit to Anna- there were a few close calls. This one should be easy. The place he was planning on stealing from was a run down store covered in rust and whose sign was broken with words missing. Another night of stale bread and week old juice to look forward to. All though he had to admit, it was way better than nothing.

"Okay, but I wanna help! I could keep watch! I could-" Anna started to say but stopped when she saw Castiel's face.

"Anna, you need to stay where it's safe. If I got caught and you were with me they'd take you away." Castiel said sternly making her look at him.

"But I have a funny feeling about this one… I can't explain it…" Anna said looking down.

"I'll be fine don't worry." Castiel said with a smile.

"Be careful…" Anna said pulling him into a hug and after a few minutes he pulled away picking up her little stuffed Angel and handed it to her. It was like her good luck charm, she carried it everywhere.

"Alright, I'll be back. I promise." He said to her before climbing the fence and jumping to the other side, unable to shake the worried look she gave him.