Hey Vintage,
This is a really enjoyable read, for so many reasons!
"Sometimes... sometimes... sometimes... he knows" I love the progression in your story and it's a great lesson in how the shape of a lyric can really amplify the message of the words.
I found it delightful that after the "And hold on tight until the good times roll" line I was thinking the next section would be in contrast, and more positive. Then I realised you'd played me, as I was following the protagonist's example in believing something is going in one direction, but actually it just keeps going further away.
I found the change from 'you' to 'he' startling too. I could only speculate with uncertainty on how it affects the story and what you're trying to convey, but that's what makes it fun.
Great imagery all the way through as others have said, but the line "Though the sticker warns, do not climb inside here" really drew me in to the situation.
All the best,
Scott.