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"Crowley has the Colt!?" Lillian yelled, after Sam and Dean recounted the events of the Supernatural convention to her, Bobby, and Castiel.
"You said that like you know who Crowley is." Dean said.
"I know... of him." Lillian told her eldest brother.
"It was never important before, but Heaven was aware of your... friendship with the King of the Crossroads." Castiel said.
"He's your friend?!" Dean yelled.
"Friend is a overstating the relationship. We had beer together once, and he said he'd keep crossroads demons out Leadworth, if I told him of our hunts, not including actual names of people or the places. He seemed kinda bored, and I needed a drinking buddy, who could buy expensive whiskey." Lillian explained.
"You made a deal, after all the shit you gave me, you made a demon deal?!" Dean yelled.
"Stop shouting. And no. I never kissed him, he doesn't own my soul. It's an agreement, which has since ended because of the apocalypse." Lillian answered.
"Did you have sex with him?" Sam asked.
Lillian shivered at the thought and answered, "I'm not you, Sam. I don't have sex with demons. I just let one buy me whiskey, and a nice pair of boots, but the boots was one time. I had just told him about the Trickster, or Gabriel, killing you over and over again. He was being nice, for a demon."
"So, you pay him in stories?" Bobby asked.
Lillian nodded, and said, "Yeah. And before you ask, no I don't know where he is. I have his number, but it's the apocalypse, and I am not ringing it."
"Our sister's friends with a demon." Dean whispered, while placing his head on the kitchen table.
"Again, friends is... No, we're friends. He's only tried to kill me a couple of times."
⊶⊶✞⊷⊷
A few weeks after that awkward conversation, Lillian was on the phone to a hunter, trying to tell him that it was in-fact the apocalypse, so demons were going to be more common than anyone would like, and he'd have to deal with that fact. Fortunately, the phone call was interrupted by Dean telling her that Cas had found Crowley.
Later on that evening, the three siblings infiltrated Crowley's house, and once they were inside, Sam asked, "It's Crowley, right?"
"So... the Hardy Boys finally found me. Took you long enough." Crowley said.
"You're friends with this guy?" Sam asked Lillian.
"You can't judge me, Sam."
Crowley didn't say anything, and only walked towards them, stopping at the rug, he lifted it up, to reveal the devil's trap that was spray painted on it. "Do you have any idea how much this rug costs?" Crowley asked.
