Schottky groups are classical examples of free groups acting properly discontinuously on the complex projective line. We discuss two different applications of similar constructions. The first gives examples of 3-dimensional Lorentzian Kleinian groups which act properly discontinuously on an open dense subset of the Einstein universe. The second gives a large class of examples of free subgroups of automorphisms groups of partially cyclically ordered spaces. We show that for a certain cyclic order on the Shilov boundary of a Hermitian symmetric space, this construction corresponds exactly to representations of fundamental groups of surfaces with boundary which have maximal Toledo invariant.