The Journey of a Transwoman follows the life struggles of Roberto "Robbie" Marquez, a woman trapped in a man's body. All his life, he dreamed and hoped to be the best for his family. He comes from a long line of police officers and soldiers. His grandfather, Amorsolo Marquez, expects him to follow in their footsteps, continue the family legacy, and prove that he is the bravest of all the Marquezes. Due to pressure from his family, Robbie kept his identity a secret from everyone except his mom and cousin. He lives with his parents (Gina and Lando Marquez), along with his grandmother, Feliciana Marquez, his brother, Justin Cedric, and his loving cousin, Angela Marquez. Unbeknownst to Amorsolo, Robbie is not the grandson he expected him to be.
Later, Robbie is adopted by a wealthy couple who want to help him achieve his dreams and desires in life-to fully become a woman. As time passes, Robbie faces more hurdles and setbacks. He realizes that he has to stay true to himself, leading him to decide to undergo full sex reassignment surgery to become the woman he always knew he was meant to be. She transitions from Robbie and becomes Olivia Mariano, a successful vlogger, businesswoman, and COO at an apparel company owned by her adoptive parents.
As Olivia begins fulfilling her dreams, fate reconnects her with Marlo, the man she fell in love with as Robbie, and Phoebe, the woman who humiliated her and caused Robbie great suffering. As their worlds collide, tension rises between Olivia and Phoebe as they fight for the heart of the man they both love. All Olivia wants in life is acceptance and to resolve the rift between her and Amorsolo. But what if her family, especially her cruel grandfather, refuses to accept her? And what if Marlo finds out that she used to be a man? Will she ever get the acceptance she's longed for all her life?