The paper explores two literary texts - Dostoevsky's novel Crime and Punishment and Euripides' play Bacchae - from the point of view of immature masculinity and the catastrophe that can follow if the boy fails to achieve a genuine separation from the maternal object. The author examines the masculine anxieties and defences that arise when the boy fails to work through the Oedipus complex and instead retreats to a dyadic relation with mother which excludes the father. This retreat involves a denial of reality and the creation of a paranoid world in which his own wishes to take possession of mother can be experienced by him as an intrusion by the mother into his own masculine identity and ultimately as castration by the mother. Attempts to resolve this threat to masculinity include the use of anal defences and tyrannical states of mind in the creation of a pseudo-masculinity.