In order to estimate accumulated excess pore pressures in the soil around a cyclically loaded (offshore) foundation structure, cyclic laboratory tests are required. In practice, the cyclic direct simple shear (DSS) test is often used. From numerous undrained tests (or alternatively tests under constant-volume condition) under varying stress conditions, contour diagrams can be derived, which characterize the soil's behavior under arbitrary cyclic loading conditions. Such contour diagrams can then be used as input for finite element models predicting the load-bearing behavior of foundation structures under undrained or partially drained cyclic loading. The paper deals with the general behavior of a poorly graded medium sand in cyclic DSS tests under undrained loading conditions. The main objective of the research was to investigate and parametrize the soil's behavior and to identify possible effects of sample preparation. Numerous tests with varying cyclic stress ratios (CSR) and mean stress ratios (MSR) have been conducted. Also the relative density of the sand was varied. A new set of equations for a relatively easy handable mathematical description of the resulting contour plots was developed and parametrized. In the original tests, the sand was poured into the testing frame and carefully compacted to the desired relative density by tamping. In offshore practice, a preconditioning of a soil sample is usually realised by cyclic preshearing with a certain CSR-value or additionally by preconsolidation under drained conditions. By that, a more realistic initial state of the soil shall be achieved. In order to investigate the effect of such a preconditioning on the resulting contour diagrams, additional tests were conducted in which preshearing and preconsolidation was applied and the results were compared to the test results without any preconditioning. The results clearly show a significant effect of preshearing and an even more pronounced effect of preconsolidation for the considered poorly graded medium sand.