Adaptive software becomes more and more important as computing is increasingly context-dependent. Runtime adaptability can be achieved by dynamically selecting and applying context-specific code. Role-oriented programming has been proposed as a paradigm to enable runtime adaptive software by design. Roles change the objects’ behavior at runtime, thus adapting the software to a given context. Most approaches focus on optimizing language implementations neglecting the fact that the generated code is a verbose description of contextual roles in an object-oriented paradigm, which incurs an overhead. This paper takes a novel approach to reduce the semantic gap. We propose ObjectTeams/Truffle, to the best of our knowledge, the first virtual machine that optimizes the dispatch of contextual roles. We evaluate the implementation with a benchmark for role-oriented programming languages achieving a speedup of up to 2.49× over the reference implementation ObjectTeams/Java and 1.2× over an optimized version ObjectTeams/Java using Dispatch Plans.