Due to the diversity of carbon nanotubes (CNTs), polymers, and the preparation processes of the composites, CNT-filled polymeric composites present various piezoresistive properties. One puzzling issue is the concurrence of a negative piezoresistive effect and a positive piezoresistive effect in composites with different polymer matrixes. In this paper, we present a microscopic view of the nature of the positive piezoresistive effect and its dependence on the polymer matrix types based on the model in our previous study, in which the piezoresistive behavior was tailored by a parameter-the average junction gap variation (AJGV)-describing the statistical property of the CNT conductive network. The microscopic movement process of CNTs embedded in a polymer matrix was analyzed and then the Poisson's ratio of the polymer matrix was determined as a key factor that is in charge of negative or positive piezoresistive properties. The obstacle effect of polymer chains on the movement of CNTs was also found to be responsible for the positive piezoresistive effect as it affects the AJGV in compressive strain. Based on numerical simulations of CNT network deformation with different Poisson's ratios and minimum junction gaps caused by the obstacle effect, the positive piezoresistive effect was found resulted from the obstacle effect on CNT junction gap variations that exceeds the initial value of the AJGV caused by the CNT network deformation, and only occur under the precondition of the polymer matrixes with a large Poisson's ratio close to 0.5. The conclusions were then verified experimentally using composites with two kinds of polymer matrixes with significantly different Poisson's ratios.