Contact interface is essential for the dynamic response of the bolted structures. To accurately predict the dynamic characteristics of bolted joint structures, a fractal extension of the segmented scale model, i.e., the JK model, is proposed in this paper to comprehensively analyze the dynamic contact performance of engineering surfaces and revisit the multi-scale model based on the concept of asperities. The influence of asperity geometry, dimensionless material properties, and the elastic, elastoplastic, and full plastic mechanical models of a single asperity is established considering the asperity–substrate interaction. Then, a segmented scale contact model of rough surfaces is proposed based on the island distribution function in a strict sense. The mechanical contact process of determining rough surfaces is divided into small-scale, medium-scale, and large-scale stages. Moreover, cross-scale boundary conditions, i.e., al1′, al2′, and al3′, are provided through strict mathematical deduction. The results show that the real contact area and contact stiffness are positively correlated with fractal dimension and negatively correlated with fractal roughness. On a small scale, the contact damping decreases with an increase in load. In meso-scale and large-scale stages, the contact damping increases with the load. Finally, the reliability of the proposed model is verified by setting up three groups of modal vibration experiments.