Transsexualism refers to the conviction of belonging to one sex in individuals born with normal sexual characteristics of the other biological sex. The hormonal-surgical treatment of this population has proliferated throughout the past decades and is recent in Portugal. The irreversibility of the sex-reassignment surgery and the lack of knowledge still surrounding transsexualism raises questions that require research in this area. This paper describes a rare-case occurrence of two transsexual brothers who received hormonal-surgical treatment. The evaluation of the treatment is generally very positive, both from the medical and the subjects' points of view. It is only partially positive in terms of personal and social life in the new sex (e.g., reported sensations, humour, social acceptance and success). The individuals' profiles correspond to potentially positive prognostics, and the results suggest that this treatment may have been adequate for these two cases. Future follow-up studies are nevertheless necessary.