Background and Objectives: Nowadays, indication of composite materials for various clinical situations has increased significantly. However, in the oral environment, these biomaterials are subjected (abnormal occlusal forces, external bleaching, consumption of carbonated beverages, etc.) to changes in their functional and mechanical behavior when indicated primarily for patients with masticatory habits. The study aimed to recreate in our lab one of the most common situations nowadays—in-office activity of a young patient suffering from specific parafunctional occlusal stress (bruxism) who consumes acidic beverages and is using at-home dental bleaching. Materials and Methods: Sixty standardized class II cavities were restored with two nanohybrid biocomposite materials (Filtek Z550, 3M ESPE, and Evetric, Ivoclar Vivadent); the restored teeth were immersed in sports drinks and carbonated beverages and exposed to an at-home teeth bleaching agent. The samples were subjected to parafunctional mechanical loads using a dual-axis chewing simulator. A grading evaluation system was conducted to assess the defects of the restorations using different examination devices: a CBCT, a high-resolution digital camera, and periapical X-rays. Results: Before mechanical loading, the CBCT analysis revealed substantially fewer interfacial defects between the two resin-based composites (p > 0.05), whereas, after bruxism forces simulation, significantly more defects were identified (p < 0.05). Qualitative examination of the restorations showed more occlusal defects for the Evetric than the other nanohybrid composite. Conclusions: There were different behaviors observed regarding the studied nanocomposites when simulation of parafunctional masticatory forces was associated with aging treatments.