Recent studies have shown that under the influence of feminist theory, today one of the most popular areas of academic children's literature criticism is "the rereading of texts for previously unrevealed interpretations" (Paul, 2004: 142). By "rereading," academic feminist children's literature critics look at the ways ideological implications are played out in the text. Rigid male/female gender distinction, sex-role stereotyping and sexism are questioned. On the other hand, there is also "a critical desire to see if a feminine literary tradition, and feminine culture, could be made visible" (Ibid). Multiplicity, jouissance (Cixous, 1991) and language that speaks "in a different voice" (Gilligan, 1982) are welcomed and embraced. In the same light, this paper looks into the representation of gender in George MacDonald's "The Princess and the Goblin" (1872) and its sequel, "The Princess and Curdie" (1883). The gender transgression in MacDonald's Princess books is investigated in three different aspects: the first section focuses on how Curdie the male protagonist transgresses the gender boundaries by using "sounds of nonsense" (instead of the typical arms and armour) to fight against the evil goblins. The second section concentrates on how Princess Irene's great-great-grandmother's magic thread (a symbol of the female spirit) helps both the male and female protagonists transgress their gender spheres is studied. Lastly, the final section also studies the representation of the great-great-grandmother, who is transgressively portrayed as a divine god that possesses multiple unstable forms and identities. The study will illustrate that under the influence of Romanticist thinking, the female in MacDonald's Princess books is a symbol of irrationality, imagination, sentiments and Nature. It is associated with hope, salvation, divinity and nurturing Nature. On the other hand, reason, rationality, and the opportunistic nature of the male are depicted as blindness, an exclusive dependence on sight, and limitations of the male protagonist. To seek salvation, the male protagonist must transgress the line of demarcation and learn the mystic power of imagination and irrationality from the female spirit. (Contains 6 footnotes.)