He would, if Sam didn't decide he wanted first shot at it! Still, it seemed like Sam got the hang of it easily enough, and Dean let go of his hand, licking his lips and resting on both elbows again. His breathing was a little shallow but he wasn't out of his mind yet. They'd both need to figure each other out like this too, now.
A hiss came as Sam licked just the tip and Dean reflexively nudged his hips up. "Not gonna pussy out on me, right, Sammy?" He grinned breathlessly at him, spreading his legs a bit more, well aware of how attractive he was to other people but not quite sure how much that'd work with Sam.
If this was going to be how their relationship was now, he'd have to test the waters at a later time.