Recent research in Taiwanese families has found that children’s transgressions are narratable and parents encourage children to confess and reflect upon their faults. Little, however, is known if adults do the same when talking with children or other adults. This study examines transgression stories from interviews with 102 adult participants in Taiwan. It finds adults often tell stories about the faults of close family members such as spouses, parents, children, and aunts and uncles. However, they are less likely to tell stories of their own faults. Furthermore, they say telling transgression stories to children must take into account the child’s age and the story’s potential didactic value. The study also finds that many stories, especially those told by older adults, i.e., grandparents, articulate part of a “master story” lamenting how they persevered from a bitter past to a much better present. Such a story shapes cross-generational narrative and lends greater moral authority to elders. Finally, implications are discussed how this study sheds light on a theory of confessional narratives by authority figures across different cultures.