Background/Context: Computer programming is rarely accessible to K–12 students, especially for those from culturally and linguistically diverse backgrounds. Middle school age is a transitioning time when adolescents are more likely to make long-term decisions regarding their academic choices and interests. Having access to productive and positive knowledge and experiences in computer programming can grant them opportunities to realize their abilities and potential in this field. Purpose/Focus of Study: This study focuses on the exploration of the kind of relationship that bilingual Latinx students developed with themselves and computer programming and mathematics (CPM) practices through their participation in a CPM after-school program, first as students and then as cofacilitators teaching CPM practices to other middle school peers. Setting: An after-school program, Advancing Out-of-School Learning in Mathematics and Engineering (AOLME), was held at two middle schools located in rural and urban areas in the Southwest. It was designed to support an inclusive cultural environment that nurtured students’ opportunities to learn CPM practices through the inclusion of languages (Spanish and English), tasks, and participants congruent to students in the program. Students learned how to represent, design, and program digital images and videos using a sequence of 2D arrays of hexadecimal numbers with Python on a Raspberry Pi computer. The six bilingual cofacilitators attended Levels 1 and 2 as students and were offered the opportunity to participate as cofacilitators in the next implementation of Level 1. Research Design: This longitudinal case study focused on analyzing the experiences and shifts (if any) of students who participated as cofacilitators in AOLME. Their narratives were analyzed collectively, and our analysis describes the experiences of the cofacilitators as a single case study (with embedded units) of what it means to be a bilingual cofacilitator in AOLME. Data included individual exit interviews of the six cofacilitators and their focus groups (30–45 minutes each), an adapted 20-item CPM attitude 5-point Likert scale, and self-report from each of them. Results from attitude scales revealed cofacilitators’ greater initial and posterior connections to CPM practices. The self-reports on CPM included two number lines (0–10) for before and after AOLME for students to self-assess their liking and knowledge of CPM. The numbers were used as interview prompts to converse with students about experiences. The interview data were analyzed qualitatively and coded through a contrast-comparative process regarding students’ description of themselves, their experiences in the program, and their perception of and relationship toward CPM practices. Findings: Findings indicated that students had continued/increased motivation and confidence in CPM as they engaged in a journey as cofacilitators, described through two thematic categories: (a) shifting views by personally connecting to CPM, and (b) affirming CPM practices through teaching. The shift in connecting to CPM practices evolved as students argued that they found a new way of learning mathematics, in that they used mathematics as a tool to create videos and images that they programmed by using Python while making sense of the process bilingually (Spanish and English). This mathematics was viewed by students as high level, which in turned helped students gain self-confidence in CPM practices. Additionally, students affirmed their knowledge and confidence in CPM practices by teaching them to others, a process in which they had to mediate beyond the understanding of CPM practices. They came up with new ways of explaining CPM practices bilingually to their peers. In this new role, cofacilitators considered the topic and language, and promoted a communal support among the peers they worked with. Conclusions/Recommendations: Bilingual middle school students can not only program, but also teach bilingually and embrace new roles with nurturing support. Schools can promote new student roles, which can yield new goals and identities. There is a great need to redesign the school mathematics curriculum as a discipline that teenagers can use and connect with by creating and finding things they care about. In this way, school mathematics can support a closer “fit” with students’ identification with the world of mathematics. Cofacilitators learned more about CPM practices by teaching them, extending beyond what was given to them, and constructing new goals that were in line with a sophisticated knowledge and shifts in the practice. Assigned responsibility in a new role can strengthen students’ self-image, agency, and ways of relating to mathematics.