[Looks at him for a moment, stopping immediately at his touch, but also seems to waver between insisting on preparing him more, but then... he's never been great at saying no to him, so he relents, drawing his hand back]
Since you asked so nicely. Lie on your back. [Taking up the oil again so he can slick himself up more - he'd normally keep him in his lap, but with him on his back he can control how deep he pushes in at least to start]