Pulse transit time (PTT) has been widely used for noninvasive examination of the arterial viscoelastic properties, such as elasticity, compliance, and stiffness of the vessel walls. PTT is usually determined as the time interval between the peak of the electrocardiogram R wave and the foot of the photoplethysmogram (PPG). However, it was observed that the PPG is affected by the applied contact force between the photoplethysmographic sensor and the measurement site, e.g., finger. In this study, the nonlinear biomechanical properties of the finger arterial wall were considered when investigating the changes in PTT with varying contact force. Emphasis was placed on the changes in the shape of the arterial wall pressure-volume curve. The simulation results indicated that at positive transmural pressure, PTT increased with the applied contact force, reaching the maximum at zero transmural pressure and remaining at a constant level at negative transmural pressure. The theoretical analysis was further verified by the experiments carried out on thirty young subjects and six elderly subjects using twelve discrete levels of contact force.