He takes hold of the plug, twisting it slightly to make certain it can move freely. Even though it hasn't been in Castiel very long, it's always a good idea to double check. Then he pulls it, keeping the pull smooth and steady before setting it aside on the towel he'd used earlier for the massage oil.

With that, he grabs the lube again, taking a quick swipe over his dick before he places it against Castiel's entrance and pushes forward.