First – June 1995
At twelve, Sam was addicted to the written word. When John forbade him bringing books to the breakfast table, Sam just read the cereal boxes – which led to an argument about whether he was disobeying a direct order. John said that he'd forbidden Sam from reading at the table; Sam argued that John had just told him he couldn't read books. Since this was before Sam became a teenager and went moody the argument was affectionate and Dean ignored it, using the distraction of the other Winchesters as a way of getting more than his share of the Lucky Charms.
So when the Winchesters packed up for a six hour drive north, Dean was glad to see that Sam had a bloody big book to read. Sam, sitting in the back seat of the Impala while his Dad and Dean talked hunt in the front, got bored pretty quickly – and a bored Sam was an annoying Sam. But today Sam just buried himself in whatever the book was and had to be prodded back to awareness when it was time for lunch.
All was well until they'd settled in the next crummy motel that was going to be their home base. Sammy was sitting on a bench outside, within Dean's line of sight, of course, reading while John researched and Dean cooked. When Dean went to call him for dinner he didn't respond. Eventually, Dean had to go over to drag his annoying little pain in the ass brother back to eat. Which was when he found out that Sam had stopped reading and started crying.
Dean might tease 'Samantha' about being a girl, but he knew that Sam always did his best to imitate his big brother in everything, and that included not crying unless he was really sick or badly injured. So there was no way he was leaving Sam to cry without finding out why. When Sam refused to answer his questions, Dean sat down next to him, shoulder to shoulder, thigh to thigh, right in Sammy's personal space, and told Sam he wasn't moving until he got an answer.
"Okay, that made no sense at all. Wanna try again in English?"
"Gandalf just died in Moria."
"Okay, that's still not English. Who the hell is Gandalf, how did he die and what is Moria? Or is Moria a she? Gandalf died in her? Kinky!"
"No!" Sam stared at Dean as if he was something disgusting, probably slimy. "The Lord of the Rings! This book! Gandalf just died!"
"This is about a book?" Dean didn't know whether to be relieved or annoyed. "Dude, I thought you were sick or something. How old are you? It's just a story. Now put it away and come and eat."
But later that night, when Sam was asleep and John was out hunting, Dean picked up the book. He wanted to see what this book that made Sam cry was all about. But five pages in he had fallen asleep over the anthropology of hobbits and when he woke up he decided life was just too short to read Lord of the Rings.