This article deals with the literary and artistic creative activity of B. N. Shiryaev, a writer of the second wave of emigration, from the point of view of reflection of Soviet reality and Soviet man brought up and educated during two prewar decades. For the purposes of the research, the author chooses works of the writer focusing on the central topic of attitude towards the Soviet world; thus, the author refers to I am a Russian Man, a collection of short stories and stories Sheep’s Puddle, Kudeyar’s Oak, and Cornet Vakulenko. Referring to I am a Russian Man, the author demonstrates the difference between the Russian and the Soviet person, as depicted by Shiryaev, and examines the system of satirical methods the writer uses to describe the abnormal and absurd sides of the Soviet reality, which was wholly led by Marxism-Leninism depriving anything that was alive of life. The author raises the question about how Shiryaev’s satire corresponded to Soviet satire and the negative role the collaborationist ideal of the author played with him believing in the recovery of the harmony of Russian life under Hitler. In order to provide more detail to the understanding of Shiryaev’s perception of the Soviet world by means of examining the topic of the Great Patriotic War, the author analyses his stories Sheep’s Puddle, Kudeyar’s Oak, and Cornet Vakulenko. In its plot, each of the stories realises one and the same idea of the fact that the war and German occupation became a test for the Soviet authorities and ideology, an unexpected opportunity for the Russian people under Soviets to compare the Soviet regime and reality and the ones dominating in the territories occupied by Germans. While analysing the texts, the author makes an attempt to substantiate the moral and ideological one-sidedness of such a concept and demonstrate the inconsistency of its literary embodiment.