This was such an interesting and entertaining read. I loved the dreamscape journey direction you went in with this story. Having a little background on Cassandra in the beginning was helpful, as it allowed me to imagine everything else going on. The addition of Josie added another dynamic to the story I wasn't expecting but still liked. Then the main strangeness of the journey was exciting to read through.
I was in anticipation of who or what would pop up next. I think the same went for whenever the Conductor made an appearance. He was the right amount of creepy, mysterious and generally unsettling in the best way for this tale.
I also felt at ease with the way you wrapped up the story and Josie's fate. Overall, I truly enjoyed your work!