This conceptual paper is concerned with the application of Contextual Family Therapy to gay father families (Boszormenyi-Nagy & Krasner, 1986). Gay fathers experience social and sexual stigma as a result of being both gay and male caregivers of children. Concurrently, much of family theory and therapy is laden with heteronormative assumptions and biases. However, after reviewing several studies that highlighted the activist nature of parenthood for gay fathers, Contextual Family Therapy social justice concepts of entitlement, loyalty, and legacy are offered as a new paradigm for understanding gay father families. Contextual Family Therapy therefore may frame how gay father families enact constructive entitlements for creating families that bend gender stereotypes about gay men (and men in general) as caregivers while remaining flexible and inclusive of adopted and fostered children. The professional implications discussed include suggestions for the therapeutic applications of Contextual Family Therapy with gay father families.