This paper looks at how menstruation creates an issue when experienced by transgender men and non-binary individuals assigned female at birth. Societal definitions look at menstruation through a cisgender lens labeling it as a woman's issue. However, there are many bodies that bleed but are not women. These individuals under the larger transgender identity who are assigned female at birth are already pushed to the margins in a society that has adopted sex and gender binaries as its norm. In such a backdrop, the puberty experienced by these individuals are also entrenched in cisnormative messages that make their menstruating journey more complicated. These complications and its effects have been noticed by examining the experiences of 6 persons who were assigned female at birth but feel this gender identity to be incongruent to their embodied gender. My analysis focuses on the internalized stigma due to feminization of the process of menstruation in trans individuals, the gender dysphoria associated with the experience of bleeding, and the exclusion strategies of a cisnormative society. The paper also looks at the strategies developed by the participants in dealing with their menstruation.