To be fair this would have made a job that involves lots of rubbings about a bit more uncomfortable which may factor into why it never even entered his mind to try it. As for reversing their roles sometimes, well, when has he ever said no to that? And they do that the setup Jack has made here at the shop now. Seems a shame not to take full advantage of it in every sense.
He shivers as it trails over his skin, cool and smooth after the heat of his hands. He knows what's coming before Jack warns him, because he can hear that smile in his voice.
The first strike still gets a surprised, "Ah!" from him but starting slow and building up is a good plan. It allows him to adjust to the new sensation and he only grows more vocal as it increases. Probably for the best they're in a more remote location tonight even if his cries are very much ones of enjoyment.