From sex toys to fertility trackers to vaginal fitness, the design of vaginally inserted technologies often mirrors gendered norms and societal taboos. These norms perpetuate the vagina as an obscure and mystified area, making it difficult for designers to find their way amidst a web of technical, material, and ethical concerns. In this paper, we present a mingling of our experiences as designers, together with feminist and posthuman literature, to discuss the challenges and tensions arising when designing in this space. We provide alternative framings and reflect on how the case of designing for the vagina creates blurry definitions of the inside/outside of the body and of medical/non-medical devices. We offer future directions on how we might demystify and destigmatize designing for vaginas, calling for more queer and feminist approaches to intimate design.