20 Questions

Author's Note: I had intended to upload this chapter yesterday, but I had no internet access. My apologies.

Chapter Summary: Things are better when Dean's mind is busy.

No more jokes, Sam said about twenty minutes ago. He was getting tired, he said, and it wasn't funny anymore.

You privately disagreed, but the kid was looking pretty rough around the edges, maybe getting one of his headaches again or something, so you let him be. But your brain is bored, which is bad because when that happens it finds its own toys to play with – sharp, burny, dangerous toys that you keep locked up in a deep dark closet because they hurt to play with. Sometimes at night, they get scattered around and bad stuff happens, and that's one thing, but during the day, when you're behind the wheel and responsible for the safety of Sam and Baby – and, for the moment, Cas, you guess – you can't afford to have your evil subconscious throwing Hell-toys out of its crib to try and get your attention.

You need a distraction to keep that from happening. Fortunately, though Sammy doesn't want to play, there's still Cas.

"Hey, Cas. Wanna play 20 Questions?"

"What is 20 Questions?"

You laugh easily. "Hey, you're a natural. Off to a great start already."

"…I don't understand."

"I'll think of something. You ask me yes-or-no questions. If you haven't figured out what I'm thinking of by the time you've asked twenty questions, I win. If you figure it out before then, you win."

"I win?" he says dubiously. "By asking no questions?"

"Ask him something he can answer with the words 'yes' or 'no'," mumbles Sam, without opening his eyes.

"Why?"

"Nope. Try again, Cas," you chuckle.

"That isn't what I meant," he says, sounding disgruntled. You check the mirror, and yup, there's a pouting angel in your back seat. Awesome.

"Is this really necessary?"

"Yes!" you answer. "That's it, Cas! See how I could answer, just by saying 'yes'? That's the kind of question you want!"

God, you love messing with angels. And now, a moment of silence to contemplate just how wrong that sentence is…

Yeah, screw that. "Okay," you tell him. "I've got something. Guess what it is," and you lean back and picture a nice, big, flaky-crusted piece of gooey cherry –

"Pie," announces Castiel assuredly. "You are thinking of pie."

Damn angels and their creepy mind-reading abilities! While you're working up to bawl him out, he interjects, "Oh. It was supposed to be a question, wasn't it? Dean, are you thinking of pie?"

"CAS! GET THE HELL OUT OF MY HEAD!" you yell, loud enough to make Sam jump. "Sorry, Sam." You didn't mean to disturb him, even though you are genuinely pretty mad at Cas. Damn angel should know better by now than to go snooping around in your head, doggone it, you have talked about this before!

"I think that is probably impossible," says the angel dismally. "I have tried."

"He doesn't want you reading his mind, Cas," translates Sam. "Most humans feel that way, remember? We like a little bit of privacy."

"Yeah, like we've talked about a zillion times!" you say heatedly. "And anyways, reading minds is cheating! You wouldn't wanna be a cheat, now, would you? 'Cause that's pretty much the same as stealing…" You feel yourself settle a bit, because you know stealing will freak him out.

It does. "I am sorry," he apologizes. He sounds worried. "I will not steal, or cheat, or read your mind again."

"Good!" you say, sternly, to make sure you got the point across. And, hey, you are still a little peeved by his abuse of power. "Now, guess what I'm thinking of!" you command.

"Mastodons!" he snaps.

Sam, who was settling back into his seat, sits up again and twists to look at Cas, flashing you a glimpse of his spectacular WTF? face on the way.

"Mastodons?" Sam queries.

"Mastodons?" you echo. "Why would I be thinking of mastodons? I'm not sure I even know what a mastodon even is!" That's a lie, by the way. You totally know it's a giant hairy badass prehistoric version of an elephant. Still, why Cas would think you were thinking of one is beyond you.

"You asked me to guess," he says sulkily. "I was not aware that the guess had to be logical."

"That's why you're supposed to ask twenty questions first," says Sam.

There's a beat.

"…Now?"

You roll your eyes, even though you know he can't see it from where he's sitting. Or, who knows, maybe he can. Maybe he can see right through your head, and your brain, and your eyeballs… yichh. Freakin' angels.

"Yes, Cas, now. Any time. Ask away."

"Are you thinking about sexual intercourse?"

Sam gives up pretending to sleep and lets out a snort of laughter. Doesn't bother you, though; you're a pretty simple guy, and you've never pretended otherwise.

"For once in my life, no," you say, because you had something else in mind. "But ask again in seven seconds. That was a good guess."

Silence falls again, just about long enough to be awkward.

Then Castiel asks again.

"Are you thinking about sexual intercourse?"

"No, Cas!" you groan.

"You instructed me to ask you again in seven seconds," he accuses. "It was seven seconds."

You consider explaining it to him, but decide it's not worth the effort. "Never mind. Ask something else."

"Are you thinking about beer?"

"No."

"Are you thinking about whiskey?"

"No."

"Are you thinking about alcoholic beverages of any kind?"

"Nope."

"Are you thinking about Hell?"

You nearly jerk Baby off the road again. "I am now!" you snap. "Thanks a bunch, Cas!"

"You're… welcome," he says uncertainly, and you can just hear him wondering why you would want to be reminded of Hell. "Does this mean I win? That was only eight questions."

"No!"

Sam comes to the rescue. "It doesn't count, because you made him think about it by saying it," he explains. "Why don't you try asking less specific questions? You can narrow it down that way."

"Okay," agrees Castiel. "Are you thinking of something you would hunt?"

"No way," you say. You'd never do that to Baby.

"Are you thinking of a living thing?"

You consider that for a moment. "Totally," you announce, feeling an affectionate grin slide onto your face.

"Are you fond of this living thing?"

"Oh, yeah."

"Is it Sam?"

"Not this time," you say, winking at your brother, who has gone a little bit red.

"Is it Bobby Singer?"

"Nope."

Cas is quiet for a moment. Maybe he's stumped. "Does it have wheels?" he suddenly asks, an edge of suspicion in his voice.

Aww, man, he knows. He's got you now.

"Yes," you reply. You're feeling pleased, though, that he recognizes the fact that you keep Baby in the category of 'living things,' even though it means he's gonna win.

"I see," he replies, sounding satisfied. You brace yourself for the last question, the one that will give him the game.

"Is it a tiger?"

Wait, what?

"Is it spray paint?" he presses, without waiting for an answer. "Is it a cup of coffee?"

"Cas! What are you doing?" cries Sam. There's that wtf? face again. In fact, you suspect there's an actual included in there. "You know it's something that's – " he clears his throat, " – 'alive', and has wheels, and you guess 'a cup of coffee'? What cup of coffee have you encountered that's alive and has – you know what, actually? I don't really wanna know. The point is, you knew it was a living thing that Dean likes, and you asked if it has wheels, which I'm pretty sure means you know what he's thinking of. What gives?"

"Of course I know that Dean is thinking of this vehicle," says Castiel patiently. "But I understand this game is called 'Twenty Questions', and I have only asked seventeen, if you count all of my guesses and don't count the ones I asked prior to your informing me that reading Dean's mind constitutes as cheating. Therefore, I must ask two more questions before I can ask if Dean is thinking of the car. Then it will be the twentieth question, and I will win."

You decide Sam would make a great kindergarten teacher, 'cause he is way more explain…ation…ier…ative… whatever! You give up!

"You can ask as many as twenty questions," Sam is saying. "But if you think you know what he's thinking of before that, you can guess even if you haven't already asked nineteen other questions. You don't have to use all twenty to win the game."

"Oh. I see," says Castiel. "Dean. Are you thinking of your car?"

"Yes!" you confirm. It's actually kind of a relief. You hadn't realized it, but this whole process kind of dragged on.

Evidently, in addition to being dicks, angels are pretty much morons.

Well, morons with wings and superpowers, but that just makes it worse, doesn't it?