The behaviors and stresses of an O-ring under uniform squeeze rates and internal pressure change with real time. Therefore, the behaviors and stresses of O-rings under uniform squeeze rates and internal pressures should be studied with real time. To achieve this, a loading device for a transparent type photoelastic experiment, through which various internal pressures and uniform squeeze rates are applied, was developed. The validity of the loading device in analyzing the behaviors and stresses of the O-ring under uniform squeeze rates and internal pressures with real time was verified. It was observed that the filling phenomenon of the O-ring into the space between the lower and front side occurred after forcing out continued for a duration of time. The study also indicated that maximum shear stress would be more effective as a fracture parameter than the maximum normal stress fracture criterion for an O-ring made from rubber.