Like other Lost Boys, Tootles was a baby who fell out of his pram and was shipped to Neverland. There he met other children like him, and they became a loyal band with Peter Pan as their leader.
When Peter discovered the Darling children and the eldest's (Wendy Darling) gift of telling stories, he made it a habit to frequently visit them unseen to listen to her stories. Whenever he returned, he would retell the stories to the Lost Boys, with Tootles eagerly listening among them.
Peter's visits were soon discovered by the Darling children, and he brought them to see Neverland. But on the way they were attacked by the pirates, so Peter stayed behind to distract them and sent Tinker Bell to lead them on home. Jealous of Wendy, Tinker Bell flew on ahead of the children and told the Lost Boys that Peter had sent a "Wendybird" and wanted it shot down. The Lost Boys eagerly took aim at the flying "Wendybird" and Tootles was the one to shoot her down with an arrow to her chest. When she fell, the Lost Boys came close only to discover that "it" was actually a girl. They tried to hide her from Peter who began to tell them of the "mother" that he had brought for them to tell them stories.