So I'm pretty sure people have already said or deduced this (and I am obviously slow on the uptake), but it dawned on me a couple of days ago that
the YED and John made out! It's totally canon.
Hear me out: in 5.10 we see a male crossroads demon make out with another man, which means demons have no problem with homosexuality (or maybe it just doesn't even matter to them, a deal is a deal is a deal and the same with a soul). We first saw this when Meg possessed Sam in
Born Under A Bad Sign and she, as Sam, flirted with Jo and almost seemed to want to rape her. She definitely was pissed when Jo turned her down.

gif evidence of Meg!Sam/Jo! (gif from
vt_graphics)
But more importantly: In
In the Beginning season four, the YED (possessing Dean's grandfather) makes a deal with Mary.
And seals it with a kiss. It's important to note that Azazel is not a crossroads demon, meaning crossroads demons aren't the only ones who have to kiss to seal the deal. All demons do (or perhaps only crossroads demons and higher up demons e.g. Azazel and Lilith).
YED kisses Mary to finalize their deal--this sets a precedence. Therefore the YED and John had to kiss in order to finalize their deal (John's life and colt in exchange for Dean's life).
So all that sexual tension and chemistry I saw in
In My Time of Dying between John and Azazel wasn't just my imagination or something I fabricated for my own amusement.
IT TOTALLY HAPPENED. Holy shit I am insanely happy. Now all I need is gifs to show the hotness and for evidence.
and I'n not even gonna touch on Azazel and his incestuous ways. ...Ok, maybe I am.
