Tris(trimethylsilyl)silyllithium (1) reacts with dialkyl(chloromethylene)ammonium chlorides (molar ratio 2:1) to give the (dialkylamino)bis(hypersilyl)methanes [(Me3Si)3Si]2CHNR2 (5a–c; a: R = Me, b: R = Et, c: R2 = [CH2]5). Due to the extreme bulkiness of the hemispherical (Me3Si)3Si substituents, the structures of these geminal bis(hypersilyl) derivatives are characterized by tremendous distortions of their molecular skeletons. This was confirmed by X‐ray structural analyses of 5a and 5c, which revealed considerable elongations of the central Si–C bonds (5a: 2.01 and 1.95 Å; 5c: 1.99 and 1.97 Å) and an extreme widening of the Si–C–Si angles at the central sp3‐carbon atoms (5a: 132.6°; 5c: 128.7°). By concentrated sulfuric acid, 5a is converted to give, after hydrolysis, the silanol (Me3Si)2Si(OH)‐CH2Si(SiMe3)3 (13). The formation of 13 is discussed as proceeding through the transient silene (Me3Si)2Si=CHSi(SiMe3)3 (11), generated by a formal (dimethylamino)trimethylsilane elimination from 5a according to an acid‐induced sila Peterson mechanism.