There are 3 fable entries you unlock by going to 2 places in a certain order. Go in this order and all will unlock in one playthrough.
First in chapter 2 you are at Beauty and Beast's apartment. They will ask if you are going to the Lucky Pawn Shop or the Butcher Shop. Select the Lucky Pawn Shop and go there first.
At the start of chapter 3 you will be in the pawn shop. Go through the conversation between toad and jack about the donkey skin coat. After that the first fable entry will unlock.
You will talk to jack a little bit then the option to tell him "that you want to look around" will come up. Select that, then walk over to the pin cushion to the right and select it with
. Your second fable entry will unlock.
At the end of chapter 4, the third fable entry unlocks when you finish talking to Johann the butcher at the butcher shop.
If you do it in this order all fable entries will unlock. The achievement will unlock when you meet the crooked man in chapter 5.