"It's Billy, right?" Dean asks, glancing up into the rearview mirror as he navigates Baby into the woods.
"Yeah." Billy is subdued, understandably.
"Look, I'm going to be honest with you," Dean says. "Where you're going, it's not pretty, it's not fun, and it sure as hell ain't easy."
"Dean." Sam reprimands softly, but Dean shakes his head.
"I'm letting the kid know what to expect." Dean tells Sam, glancing back at Billy again. Billy looks even more nervous.
"Look, what I'm trying to say is this: it's not going to be easy, but after a while, it'll feel right. There, you won't have to worry about hiding what happened to you. It's a world free from illusion and lies." Dean states. "And it's not the worst place you could end up."
"How do you know?" Billy asks quietly.
"I've been." Dean tosses out casually.
"Oh." Billy looks down.
Conversation dies as Dean brings the car to a stop and the three of them get out of the car. Sam stays back while Dean and Billy walk a couple feet away to an empty patch of dirt. Legs shaking, Billy slowly kneels down on the ground.
"Do it quick?" He asks, so softly Dean almost doesn't catch amidst Billy's quick breathing.
"Don't worry." Dean replies. Then, he places a hand on Billy's shoulder and speaks into his ear. "When you get there, look for a man named Benny Lafitte. Tell him Dean Winchester sent you. He'll help you out."
Billy glances at him fearfully but gives a short, imperceptible nod.
"Good. This won't hurt." Dean promises and steps back.
Billy nods again, visibly shaking with silent tears, and Dean swings.