Engaging in sports activity is influenced significantly by contextual factors, which can either encourage participation or lead to discouragement and disinterest. This is particularly true for sports with perceived exclusivity, such as rhythmic gymnastics, which is traditionally considered a sport for women. The present research adopts a collective case study approach, utilizing semi-structured interviews and a biographical-narrative methodology, focusing on the first Chilean children to practice this sport. The study seeks to uncover the contextual factors influencing their decision to participate and explore their experiences within the sport. Participants frequently highlighted the enjoyment derived from the sport, particularly the opportunity to manipulate various apparatus. Additionally, the study examines the crucial role of family support, experiences in school and clubs, and the influence of television and social media. In some cases, the resilience required to endure and overcome peer discrimination or ridicule is also discussed. The findings underscore that fostering an education free from gender bias can encourage broader participation in various activities, both recreational and athletic, without prejudice or fear—particularly in rhythmic gymnastics.