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“Jack what are you doing?” Cas asked.
Jack was standing, facing Dean’s closed door. His head bowed,eyes closed with one palm flat against the wood. He dropped his hand and turned to cas.
“I’m watching Dean’s dreams.” he said simply as if he was commenting about the weather.
“You’re what?” cas asked again.
“I don't sleep much and when I do I don't dream that is so I watch Sam and Dean’s to pass the time.”
“I really don't think they would be happy if they knew you were doing that.” cas pointed out with a raised eyebrow. Jack turned to look in the direction of sam's room and continued to speak as if cas never uttered a word.
“ I watch sam’s dreams sometimes but, while he has some peaceful dreams of a house full of kids with a girl named Jess, mostly he dreams of hunts gone wrong. Of him letting dean down. Dean getting hurt or worse. He often dreams of people he cares about burning on the ceiling. His dreams are full of blood and fire.” cas gives a sad look because he knows how much sam wishes for a normal “apple pie life” as dean calls it.
“I enjoy watching dean’s dreams while he has the occasional dream about hunts gone wrong, most are happy with happy memories. One of my favorites is where he is in a field with a young boy I assume it is sam they light fire to these thing according to the internet they are called firecrackers, they light them and they shot straight up into the sky they pop and the most beautiful of colors appear.” Jack says with a smile.
“Oh yes that is dean’s favorite memory it's featured in the boy’s heaven.” cas states remembering the winchesters heaven. “I remember the first time I saw deans dream’s they were so peaceful, he was sitting on a dock drinking beer and fishing, he wasn't worried about demons or monsters he was happy.” cas gave jack a sad look knowing that dean could never be that happy in real life, that he could never make him that happy. “So what is he dreaming about tonight? Is he happy or is it a bad one?”
“You.”
“What do you mean me?” Cas asked confused but with curiosity
“He is dreaming about you he is reliving the moments he fell in love with you. Did he really take you to a brothel….I think that’s what dean called it”
“Oh yes that seems like another life now dean had said that he didn't want me to die a virgin so he took me there to “get laid” as dean puts it…… no demon or monster scares me as much as that place did.” Cas says with a small chuckle.