Silicone has a relatively high coefficient of friction and silicone medical devices therefore lack inherent lubricity, leading to pain on device insertion and potential tissue trauma. In this study, higher molecular weight tetra(alkoxy)silanes, particularly tetra(oleyloxy)silane, have been used as crosslinkers in the condensation cure of a hydroxy end-functionalised linear poly(dimethylsiloxane). The resulting elastomers displayed a persistent lubricous surface of oleyl alcohol, and coefficients of friction (static and dynamic) approaching zero. Chemical structures of the synthesised silanes and surface alcohol exudate were confirmed by nuclear magnetic resonance spectroscopy. Mechanical properties of the elastomers, which were chemically identical to conventionally cured systems, suggested that an 80/20 mixture of tetra(oleyloxy)silane and tetra(propoxysilane) gave the best compromise between desirable mechanical and frictional properties.