Currently, the image of a pregnant trans man-upper body naked, at hairy chest, ripe round belly, square jaw framed by a beard-is no longer news. But, it responds eloquently to the conclusion of Freud’s essay on Sidonie Scillag, our “Young Homosexual Woman.” In 1920, Freud expressed his skepticism about the “remarkable transformations that Steinach had effected in some cases by his [sex change] operations” (p. 171). He felt that it would have been “premature” or “harmful exaggerations” to consider this type of bodily intervention a “therapy” that could “be generally applied” (p. 172). In the case of women, the tone of Freud’s speculation was cautious: “A woman who has felt herself to be a man, and has loved in masculine fashion, will hardly let herself be forced into playing the part of a woman, when she must pay for this transformation, which is not in every way advantageous, by renouncing all hope of motherhood” (p. 172). In Freud’s time, the kind of sex transformations brought about with hormones and plastic surgery by Benjamin and Money would have seemed improbably far-fetched. Nowadays, it is a matter of fertility treatments, and these trans men are able to conceive, be pregnant, and give birth. With several trans men having shown the mass public that they were able to retain their identities as men while keeping their female reproductive organs, becoming pioneer pregnant fathers, usual notions of what is male or female are challenged even further. Still, we do not know enough about the limits of our bodies. Technological developments push our comprehension and reiterate that for gender, anatomy is not destiny. Now, the questions are mostly issues of ethics and deontology. Are these the new symptoms of our times?