God, this is just ridiculously adorable. I'm having terrible, wonderful flashbacks to babysitting my little brother when he was Teddy's age. We had the opposite problem with him though - no way was he gonna let us get him out of his fireman raincoat and boots.

And yes! This is what canon says Dean wants most of all, so of course you must give it to him. It's the right thing to do. *nods*