The aim of this study was to understand the psychological dynamics and affective factors of ten (10) male-to-female (MTF) transgender living within Metro Manila. The study used multiple-qualitative and mixed-method case studies to fully understand each unique experiences of Filipino MTF transgender. Measures were three (3) psychological tests, an outcome survey and a formal interview. Among the ten (10) participants, two were enclosed to the idea that their sexual identity is female; the rest were psychologically affected by the acceptance of family and discrimination of society that made gay sons transcend to female appearance, more so being a transgender. Results indicated that transsexualism thoughts are being mediated by the affection of romantic relationship.