This study conducts a comparative assessment of subjective experience of real-world and simulated world driving for investigating factors leading to simulator sickness. Thirty professional car drivers drove a fixed-base driving simulator in real and simulated worlds under No Time Pressure (NTP) and Time Pressure (TP) driving conditions. Drivers rated their perceptions based on real-world driving and simulator driving experiences after each driving session with respect to three factors: simulator sickness, mental workload, and sense of presence. The structural equation model results revealed that drivers experienced high mental workload due to TP driving conditions (factor loading = 0.90) and repeated exposure to simulated world (factor loading = 0.20) which induced simulator sickness (factor loading = 0.41) and resulted in low sense of presence (factor loading = −0.18). Thus, it can be concluded that lack of experience with virtual reality induced high simulator sickness, increased mental workload, and low sense of presence.