The present qualitative study, through a psychoanalytic and culturally sensitive lens, aims at shedding light on the representations of the Nigerian sexual trafficking phenomenon and on the peculiarities of the relationship with trafficked women, from the perspective of five Nigerian female cultural mediators who work in the field of anti-trafficking. A semi-structured interview was developed and analyzed according to the principles of the Interpretative Phenomenological Analysis-IPA. On the background of a complex process of construction of borders between the Self and the Other, the findings show that the complexity of the cultural mediation work is higher with trafficked women due to the similarities in terms of gender, ethnic, and cultural identities. These similarities produce continuous oscillatory movements between identification/dis-identification, confusion/differentiation, and admiration/envy. Sexual trafficking emerges as a complex chain folded over itself made by a succession of internal and external usurpers, which mutually reinforces one another, worsening the mental health of migrant women and exacerbating their vulnerabilities. The findings show the need to build thinking spaces specifically directed to the female cultural mediators who work with trafficked women in order to protect them from the risk of vicarious trauma as well as to promote an awareness about the complexities involved in their work. The possibility to understand human and sexual trafficking on a deeper level allows the planning of more person-centered clinical interventions, which can take care of women’s well-being as well as prevent the high and very frequent risk of dropping out.