The hand in his hair felt almost like petting and it made Caleb blush and shiver. Not a lot of people - himself included - had ever paid much attention or care to it, but Caduceus seemed to like it and it just brought attention to something that Caleb had never considered might be an area of pleasure before. But it was nice. It grounded him and kept him from getting too over-eager or rushing through things too much. And it reminded him that Caduceus was still paying attention to him and had enough presence of mind to keep stroking through his hair and teasing at the still-damp curls.
His blush only deepened, though, at the sound of a command in Caduceus' voice. He desperately wanted to bury his face somewhere or draw his hand down between his own legs, anything just to relieve the sudden wash of tension that had built up at the base of his spine. He slid off Caduceus' cock, finally looking down at it as he wrapped his fingers around it and brushed his thumb across the tip. That hand stayed there, softly teasing, as he brought the other up to his mouth and slicked his two middle fingers. He wasn't at all aware of how indecent the gesture must have looked, and he wouldn't have cared if he did know. The only thing that really mattered was making sure he gave Caduceus what he wanted and that he made his best efforts to make it perfect.
He started with just one finger, doing his best to be gentle as he pressed along the slit again and carefully slid inside. It was the most amazing feeling. Hot and slick and smooth. He could feel the shape of his cock inside and rubbed his finger in shallow circles, trying to coax it out. He wasn't sure if he could fit a second finger inside, but he wasn't going to push it right now. Not the first time. And despite the ideas that flashed through his mind he was utterly confident that he wouldn't ever be able to fit more than two fingers inside here. But gods, he wanted to.
He was so glad he had pulled back a bit to watch this, though. He was utterly enraptured by the whole process. He thrust his finger a little deeper, careful to curve along with the shape of him, seeking more, trying to see if he could find the base and rub there. For once, Caleb's utter attention to detail was probably coming in handy, because he drank in everything. Every moan, every gasp, every twitch. It was all committed to memory.