Rufus's cabin was quiet as the Winchester boys rummaged through their old stuff, trying to figure out what to bring to the Men of Letters fortress in Kansas. Upon an out of place notebook, Sam glanced at Dean.
"Uh, Dean, why do you have a notebook full of names and …. Are those prices?" Sam looked at his brother with confusion, holding out an old, seventy-five page college ruled spiral notebook.
"Give me that! It's a record of… It's nothing important; just give it here," Dean demanded. As he reached out to grab it, Sam held it up, out of his older, but certainly not bigger, brother's reach.
"Oh no, it's definitely something, and I'm not going to give it back until you tell me what."
"Sammy! I'm warning you! Give it here or so help me God I will kick your ass." Dean rushed at Sam who hopped out of the way, still holding the notebook over Dean's head. Again, Dean went after Sam, this time managing to successfully tackle him onto the bed.
"Is this a list of every girl you ever had to pay to have sex with you? I have to say, it's quite a long list. Maybe you're not so smooth with the ladies after all!" Sam laughed at his own joke and further taunted Dean. "Hey, here's one from the day I was almost devoured by that creature in that town in Wisconsin. I'm pretty sure prostitutes don't sleep with kids. Dean, what is this?" All previous tones of joking and taunting turned serious.
"Prostitutes don't sleep with kids, no, but some people are desperate enough to pay a kid for sexual favors. Sammy… when Dad's hunting trips took too long, or if I wanted to buy you something special, I had to find a way to earn money. I was too young to get a job; I haven't, won't, and will never beg for cash, and I didn't know what else to do. I prostituted myself, and that's a list of everyone who ever slept with me and how much they paid me and when." Embarrassed and teary eyed, Dean looked away from Sam and walked to another room. With his hands on his hips and head hanging low, Dean allowed tears to fall softly on his cheeks. "It was the only way I knew how to take care of you, Sam."
"Dean, I had no idea. I wish there was… I don't even know what to say. Come here. Come give moose a hug. Maybe I could bring in a certain angel to cheer you up?"
Dean's cheeks flared with embarrassment. "No, no, definitely not. I'm fine. Let's get back to work." Of all the people in the world, he did not want Cas to know of his sexual past. They continued their work quietly, until Sam broke the silence. In an affectionate, appreciative voice, he said the one thing he knew would cheer his brother up.
"Jerk."
"Bitch."