Despite increasing global attention to improving women’s healthcare experiences, limited research has examined how cultural expectations and health system structures influence women’s pain management experiences. This study investigated women’s perceptions, expectations, and satisfaction with pain management provided by caregivers in hospitals in the Eastern Region of Saudi Arabia. A descriptive, cross-sectional design was employed, involving 307 women who experienced pain and sought care in outpatient clinics or emergency departments. Data were collected using the validated Pain Treatment Satisfaction Scale (PTSS). Descriptive statistics summarized demographic characteristics and satisfaction levels, while the Kruskal–Wallis test examined differences in perceptions, expectations, and satisfaction across groups. Results showed that 72% of participants believed pain medication was effective, and 45.3% reported that it met their expectations. Approximately half of the women were “satisfied,” and about one-fourth were “very satisfied” across all items (22.5%–31.9%). The highest “very satisfied” ratings were for nursing care related to pain (30.3%) and pain medication (31.9%). Younger women (20–25 years) reported higher satisfaction, expectations, and positive perceptions of pain management compared to women over 45 years. The findings highlight the need for personalized, culturally competent, and communication-centered pain management approaches that consider women’s emotional, social, and demographic contexts.