Chester is an emotionally fragile small boy who appears in Baby Piggy Goes to Nursery School. The moment Chester steps into the nursery school, he appears on the verge of tears, rebuffing suggestions to color, build with blocks, or even take off his jacket.

Chester does indeed begin to cry, suffering anxiety over separation from his mother, but Baby Piggy, feeling the same way about Nanny, befriends him. The pair play dress up and finally come to enjoy their time at nursery school.