Math courses serve as cornerstones to most, if not all, community college programs. Yet, these courses continue to be gatekeepers. Contextualization represents a promising venue through which instructors might break down math barriers for students. This study explores community college students' learning experiences in contextualized math classes, and how those experiences shape momentum toward success. We used a narrative inquiry approach, drawing upon the stories of six students enrolled in two contextualized math courses at a two-year college in a Midwestern state. Interviews, field notes, and survey data helped build and deepen the students' narratives. We presented each student's narrative individually, detailing their experiences in the contextualized math classes. We also discussed the thematic analysis results, which revealed six themes. The first three themes spoke to clear expectations and learning path in math, digging into and building upon math content and knowledge, and individual and group work dynamics. The latter three themes centered on discovering and recognizing utility of math, building and translating a foundation in math, and situating math within broader education and goals. This study offers empirical evidence on the potential of contextualization to enhance community college students' learning experiences and success in math, particularly across college-level math courses and various program areas.