I wanted to see Sam's and Dean's different versions of Jack getting The Talk, and
z_publicizes suggested this scenario needed Cas and Rowena, with intercut scenes between them all, and now it's all I can think about.
CAS: (sitting up straight, looking a little uncomfortable) Sex is... it's a very human interaction.
JACK: (has a serious, earnest expression)
SAM: (leaning forward, elbows on his knees) The most important thing is, make sure your partner is really willing. Sometimes people start out, and they're into it, and then they change their minds, and they can do that. It's their right. And if someone is too drunk to say no, they're also too drunk to say yes.
JACK: (has a serious, earnest expression)
DEAN: (legs crossed, glass of whiskey in his hand, casual) The most important thing is, make sure she gets hers before you get yours, if you know what I mean. Well, shit. Of course you don't know what I mean. So...
JACK: (squinting, slightly confused)
CAS: It's a way humans show affection, but it can also be purely physical, with only transient affection, or no affection at all, and that's okay as long as you're both being honest about it.
SAM: Always use protection. If your partner says you don't need to use it, use it anyway, because it's not just for them, it's for you. And anyone who doesn't insist on it has probably had unprotected sex with other people, so that makes it even more important for you to protect yourself.
DEAN: And then there's cowgirl position. This is a good one, because it leaves your hands free to do other things
CAS: And it can be messy. Not necessarily in a bad way, but maybe in an... unexpected way.
SAM: Are you sure you're still comfortable with this conversation?
DEAN: Now, some girls like getting their hair pulled, or their ass smacked. Not hard enough to really hurt, just a bit. If it seems like the time is right, just do it once, lightly. If she likes it, she'll let you know. If she doesn't let you know she likes it, that means she doesn't like it, so don't do it again. Move on to something else.
CAS: Do you have any questions?
SAM: Do you have any questions?
DEAN: You think you can remember all this?
JACK: (eyes a little wide, serious nod)
ROWENA: (starts out leaning forward, smirks and leans back into her chair) So. That's fifth base. Any questions?
JACK: (wide-eyed, bewildered stare)