This practice paper demonstrates an art therapy session that revealed the internalized monstrous and demonic identities amongst those who have sexually offended. Several of the participants represented their shadow-self as: (1) nebulous demonic self-representations, (2) internalized monstrous selves as hurtful or uncontrolled, or (3) a dichotomy of power and helplessness. Making these negative self-images visible during such an art therapy process can inform the initial step toward reconciliation, especially within the transitional space of reintegrating into society post-incarceration. Implications demonstrate the use of metaphorical expression and how such images can address the stigmatized and internalized negative self-perceptions of those who have sexually offended.