What if Dean gave Chief his safe word?
"Oh, before we get started. What's your safe word?" the chief asked, while he momentarily stopped flicking his whip.
"Funkytown," Dean said.
"OK," Chief said and started approaching Dean.
When he had taken 2 steps Dean yelled, "Funkytown, funkytown," and ran out of the room.
"Hm, he was a shy one," Chief muttered to himself and shrugged.
Once Dean was in the alley he decided two things. He was going to kill those two old magicians and he was going to make sure Sam never found out about this—or send Sam here tomorrow.