Dean knows that Sam's too young to go on a hunt in the middle of the night (into the woods nonetheless), but there's something about how sweet and innocent he looks out there.
He's so small.
And fragile.
And he keeps looking at Dean like he hung up the moon.
And he knows it's bad—that he's acting like a creep right now—but he can't help it. The feeling of Sam depending on him, needing him, it's like a never ending high.
So he's reluctant, and he makes sure to show that reluctance (because he wouldn't want Sam to know how he truly felt), but he always let's dad force Sam to come with.
Nothing's better than hearing his baby brother screaming his name when he finally gets caught by the monster.
(Sometimes, he imagines Sam screaming his name into their bed when the hunt's over.)
