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The appeal of transgender pornography, especially involving “preop”(erative) trans women, has steadily increased placing it in the top six most searched categories. In this paper I explore one unconscious function of the “pre-op” trans woman sexual fantasy that I have observed in some young heterosexual gynandromorphophilic men (i.e., men sexually drawn to the MtF “pre-op” body) who use transgender pornography and/or escorts. In contrast to a psychoanalytic reading of gynandromorphophilia in which the “pre-op” trans woman's body is understood to be “missing nothing” because she has breasts and a penis, I suggest that what is psychically compelling and sexually arousing for some men is quite the opposite: because the “pre-op” trans woman has a penis, she therefore has no vagina/womb. It is the triumph over what is missing and that should be there. The penis in lieu of the vagina/womb is evidence of her damaged procreative potential. In these cases, I propose that the sexual preference exposes the man's underlying womb envy. The “preop” trans woman is projectively identified with a felt-to-be “infertile” part of the man. The phantasized damaged woman's procreative body temporarily relieves the man of his sense of inadequacy and anxieties about his capacity to create and enliven. I illustrate this dynamic with clinical examples.