Various types of organ transplantation are now considered as standard procedures: heart, liver, kidney transplants. A recent development is the success of uterus and penis transplantation. This chapter identifies and discusses some of the main ethical issues associated with uterus and penis transplantation; it will discuss the rationale for these procedures, issues pertaining to the identification of patients who can benefit from these procedures; issues pertaining to the alternatives to transplant surgery (adoption and gestational surrogacy and phalloplasty in alternative to penis transplantation). People affected by gender dysphoria represent a special group, which is also discussed. These new developments offered by medical science change not only clinical practice, but family structure and parentage, and challenge the notions of man and woman. These developments reverse misfortune (so that, say, a man who has lost his penis can still fertilise his partner and have genetically related children); but they also challenge the moral relationships between healthcare professionals and patients, and between individuals and society.