The story of Teddy and Madeleine picks right up from where Babysitting Teddy left off. Madeleine asks a big gesture of Teddy and isn't sure how he'll take it. Madeleine's possessive nature is only a problem if he doesn't like the sentiment. This story has heavy themes of Femdom, chastity, and a grown mature man being vulnerable in a consensual BDSM/MDlb relationship.