Love the interactions between the boys. Very natural. I'm liking how you've written Sam as wanting to protect Dean, repay Dean, as I think it's a huge part of his character. The journal entries still feel a little blunt to me, but first person is really hard to write in, so it's all good. But I absolutely adore the interaction bit, and I really do just love that last line with the journal as a great subtle reminder that all is not well. I really do love the simple ankle squeeze. That felt very organic to me-oh did I mention adorable? Very nicely done.
kudos!
-crazytook