Empowering students to transfer programming skills learned in the classroom to diverse real-world scenarios remains a significant challenge in computing education. This experience report describes an approach to facilitate learning transfer and foster adaptive expertise by engaging students in co-creating contextualized worked-out examples. Worked-out examples involved asking students to create step-by-step explanations of their solutions. Through three homework assignments in a Spring 2023 database programming course, we observed substantial improvements, where students generated detailed, error-free solutions and enriched their problem-solving contexts from simple phrases to detailed stories across 17 real-life scenarios. Peer assessments indicated a supportive learning environment fostering adaptive expertise. We discuss the lessons learned and offer pedagogical implications for integrating student-generated contextualized materials in other programming courses.