Systolic blood pressure (SBP) is highly sensitive to various factors such as psychological stress, and hence its continuous monitoring is essential to evaluate different health conditions. However, conventional sphygmomanometers cannot continuously measure SBP given the time-consuming setup based on a pressure cuff. Moreover, continuous biological signal monitoring is more comfortable when no sensors are attached. A solution for continuous SBP estimation is based on pulse transit time (PTT), which determines the time difference between two pulse waves at different body parts. In previous studies, we successfully measured the PTT using a contactless setup composed by two digital color cameras recording the face and hand of subjects. Then, the acquired images were transformed into blood volume by combining multiple regression analysis and a Monte Carlo method. As a result, the delay among images allowed to determine the PPT from pulse waves. In this study, we simultaneously measured SBP and PTT by using a sphygmomanometer and the two cameras, respectively. We evaluated SBP increases (i.e., stressful situations) and the corresponding PPT by asking participants to either grasp a handgrip or momentarily interrupting breath. We also determined the SBP and PTT without asking for such exercises. Comparison results show that the mean PTT under stress was significantly lower than that without stress, which is consistent with an increased SBP. Finally, we related the SBP and PTT by a nonlinear formula with a coefficient of determination of 0.59, thus confirming the effectiveness of the proposed system.