Inspired by the use of rift-sawn softwood board for covering curved surfaces in Kokerabuki, a traditional Japanese roofing method, we investigated the flexural anisotropy of wood caused by its end-grain orientation. We measured the flexural displacement of softwood species, Chamaecyparis obtusa and Cryptomeria japonica, and hardwood species, Populus suaveolens and Cerasus serrulata. For the softwood species, this was approximately five times longer for the rift-sawn specimens than for the other grain patterns. Using the replica method to measure the softwood tracheid deformation with different flexural displacements, we confirmed the different deformation mechanisms of the tracheid in the flat- and quarter-sawn specimens, and rift-sawn specimens. In the flat- and quarter-sawn woods, on-axis loading was generated, in which the stress was concentrated on the radial and tangential cell walls parallel to the direction of tension or compression. By contrast, in the rift-sawn wood, off-axis loading was generated, in which the stress was evenly distributed throughout the corner cell walls without the wall directly resisting the tensile and compressive forces. We also concluded that the tapered shape of the tracheid walls contributes to the excellent flexibility of rift-sawn softwood.