This paper examines how transmasculine individuals who experience pregnancy navigate feminist and medical spaces, which are shaped by gender essentialism and the assumption that a normal body is a cisgender body (cisnormativity). Drawing on feminist theory, trans medical history, archival silences, and contemporary memoirs, the project argues that transmasculine pregnancy is situated between feminism and medical neglect, exposing unresolved tensions within social and institutional reproductive work. While feminist and reproductive rights movements have historically challenged patriarchal control over women’s bodies, some so-called feminists relied on biological definitions of womanhood that render transmasculine experiences as invisible or threatening. Through an analysis of U.S. trans medical experiences from the turn of the twenty-first century, along with accounts of transmasculine pregnancy within the twenty-first century, this paper demonstrates how medical gatekeeping, feminized reproductive healthcare spaces, and gender-critical feminist discourse collectively reproduce the same forms of bodily regulation they may resist or embrace. This paper argues that expanding feminist frameworks to include transmasculine reproductive experiences strengthens reproductive justice by confronting cisnormative logic in feminism and medical systems.