Ok, I used to play this game A LOT with my friends. Allow me to explain how it works:
You start with a word (I'm going to use 'Dragon' for this one) and one person has to think of a word that starts with the last letter of that word (which I'm going to say 'Narwhal' since dragon ends with 'N'). Then another person would think of a word that starts with 'L' since 'Narwhal' ends with 'L' and so on and so forth.
I'll start with Toothless. Go. o3o