It wasn't as though Caduceus had now realised what he'd been missing out on his whole life when it came to sex. It wasn't as though it had opened up a whole new world for him, unless that world was solely Caleb. He didn't regret he hadn't started sooner, no. He was happy that it was Caleb, it could only have been Caleb, and there would be no one else.
His heart swelled with affection when Caleb stopped immediately, and if he hadn't been distracted by what was happening lower down his body he would probably have smothered Caleb with kisses, told him how brilliant he was, how well behaved he was.
"Is that okay?" Caduceus asked quietly, despite Caleb's movement, despite how pleased he seemed. They both knew what the intention was here, and Caduceus had never everted inside Caleb before. The shape of his cock would make it easier, too, but Caleb seemed very content right now, eager to get more. It made Caduceus feel incredible, it gave him a whole new perspective on his own body that he had very much ignored for most of his life. He felt attractive, and it was odd, but it was also very welcome.
He was in no danger of losing the stimulation, regardless of what Caleb did or didn't do, but he wasn't going to deny either of them the opportunity to enjoy themselves more. And Caleb's request would absolutely be honoured. Caduceus' hands moved to Caleb's hips, guiding them in a gentle circle with the slightest rise and fall, keeping his cock inside Caleb and providing them both with a bit of friction. It meant Caleb pressed against the swell of his sheath, the firm mound above the slit where their bodies joined. He gripped harder than was strictly necessary, but all of that pale skin would look lovely with a few pretty bruises.
"I'll tell you, little one," Caduceus rumbled softly. "Don't worry. I'll take care of you." He took Caleb's hand in his own, leading it back to his ear. "Touch me there, as you were doing. When you move your hips I can feel you, you're pressing against me so nicely."
His hand them moved behind them, feeling where the sheets were damp with his slick and where he had pushed inside Caleb, just the slight stretch of his rim to accommodate him. He circled it slowly, thinking of pushing his fingers inside himself, but the stimulation from outside would be more than enough, he could feel the ache building up again, the sign that he would evert more very soon. Caduceus gripped Caleb's hips again, guiding him around again.