This work aimed to theoretically determine the high-energy-photon-shielding properties of flexible wood/natural rubber (NR) and NR composites containing photon protective fillers, namely Pb, Bi2O3, or Bi2S3, using XCOM. The properties investigated were the mass attenuation coefficient (µm), linear attenuation coefficient (µ), and half value layer (HVL) of the composites, determined at varying photon energies of 0.001–5 MeV and varying filler contents of 0–1,000 parts per hundred parts of rubber by weight (phr). The simulated results, which were in good agreement with previously reported experimental values (average difference was 5.3%), indicated that overall shielding properties increased with increasing filler contents but decreased with increasing incident photon energies. The results implied the potential of bismuth compounds, especially Bi2O3, to replace effective but highly toxic Pb as a safer high-energy-photon protective filler, evidenced by just a slight reduction in µm values compared with Pb fillers at the same filler content and photon energy. Furthermore, the results suggested that the addition of 20 phr wood particles, primarily aimed to enhance the rigidity and dimensional stability of Pb/NR, Bi2O3/NR, and Bi2S3/NR composites, did not greatly reduce shielding abilities; hence, they could be used as dimensional reinforcers for NR composites. Lastly, this work also reported the optimum Pb, Bi2O3, or Bi2S3 contents in NR and wood/NR composites at photon energies of 0.1, 0.5, 1, and 5 MeV, with 316–624 phr of filler being the recommended contents, of which the values depended on filler type and photon energy of interest.