Menstrual discomfort is a prevalent, diverse, and cyclical lived experience, impacting everyday lives. However, in HCI, it has been mostly approached as a data point, leaving much unknown on how technologies can care for these experiences. In response, we designed Touchware, a collection of on-body touch probes with pneumatic shape-change and weight components, which invite wearers to engage with and care for their menstrual discomfort. We report on the participatory soma design process of making Touchware and its two-week-long deployment study with 6 participants in a workplace setting. Our data analysis highlights diffuse and lingering qualities of menstrual discomfort, shedding light on how technologies may touch bodies in vulnerable states. We discuss the importance and challenges of designing touch technologies for and with bodies in the moments of menstrual discomfort. We conclude with a reflection on the agency of touch and its potential to support the self-care labour and nurturing the radical normalization of rest.