The Problems of Joyce``s sexual aesthetics have been discussed among critics in two different ways as a problem of androgyny in artistic creation and a subversion of traditional sexual hierarchy with not much co-relation between them. In fact, few critics focused on Joyce``s masochistic tendencies scattered and reflected in his works and many didn``t notice the masochistic background where the two ways meet and converge. Joyce``s aesthetics of sexuality is built on the dual aspect of femininity that promise creative fertility and threatens male artist``s identity with her power. And male artist``s desire and fear of the powerful woman as in masochism is the hidden motive and drive toward aesthetic creation. This is what Stephen and Bloom in Joyce``s works show in their theory of artistic creation and dramatization of masochistic fantasy in "Circe". Masochism``s contradictory or "impossible" way of pleasure and pain, submission and symbolic victory is the strategy for the creative use of the dual aspect of femininity as are the cases with Stephen and Bloom. This article tries not only to show the function of the dual structure in Joyce``s sexual aesthetic theory and its relation to masochism, but to explore the possibility of masochism as a typical Joycean writing.