Caleb didn't think much about whether he was supposed to do something or not. He wanted it, Caduceus wanted it. That was the only thing that mattered. He didn't keep with any gods, he didn't have any thoughts on why they were made the way they were. The only thing he knew was that real pleasure was rare and it only made sense to indulge in it when it was offered so freely. For whatever reason, something he was doing was bringing Caduceus an enormous amount of pleasure and his whole self was honed in on that.
The only problem - and it was really the best kind of problem to have - was that Caleb wanted everything and he wanted it all in the same moment. He'd seen how people came and went here and either one of them could be sent back at any moment. Even if he wouldn't remember this on the other side, he still wanted to experience all of it. And maybe some part of them would. Somewhere in the back of their mind where forgotten things went. He was torn. He desperately wanted to feel Caduceus come unwound exactly like this, but he also wanted to press against him and kiss him and see what it was like to slide inside this space.
Impulse won out, in the end. Caleb slid off Caduceus' cock again, sliding his tongue over the tip, and slowly shifted up to drape himself half over his friend's body. It was a better position, too, to slip one more finger inside of him and see just how much he could stretch him out. He nuzzled into Caduceus' chest, a little off to one side, closer to his shoulder than anything. He was pressed against the inside of Caduceus' thigh and he rutted there slightly, as if trying to tell him without actually tell him what he wanted.
"Can I?" he finally asked, his lips ghosting across Caduceus' jaw. He lifted up just enough to let him watch as he reached back and stroked himself - slick and dripping already. "If it won't feel good..." he said, but his face was wide-eyed and almost pleading. Them, as if to put a point on it, he twisted his fingers a little bit and pressed even deeper, finding the root and curling around it, pressing just a bit to see if he could get Caduceus to arch and moan again.