In 2008, the tabloid story of a pregnant transgendered man from Oregon provoked a flurry of responses—mostly negative—thus proving that even in the 21st-century blurring of gender boundaries arouses both morbid fascination and deep anxiety. Medieval tales about male pregnancy suggest a similar preoccupation with masculinity and maleness. Most of these humorous stories of folly or sexual naïveté push the gender boundaries only to reinforce them: they portray their feminized protagonists as incorrigible idiots, reaffirm child-bearing as a prerogative of women, and reinforce popular misogynous stereotypes. However, the 14th-century medieval German mære“Des münches not” goes beyond a mere juxtaposition of masculinity and femininity. This particular comic tale complicates the common plot by making its protagonist a celibate monk and therefore focusing on the tensions among several medieval masculinities. This paper uncovers the disputatious nature of late-medieval culture, ridden by deep anxiety about clerical celibacy. “Des münches not” repudiates the clergy's masculinity and simultaneously insists upon it, thus reaffirming that despite all the effeminate aspects of the monastic lifestyle, late-medieval laity nevertheless saw the clergy as both male and emotionally masculine.