Under transverse cyclic loading, slip will occur on the contact surfaces in a threaded connection, causing rotational loosening of the connection. It is necessary to detect and analyze the loosening behavior of threaded connections caused by slippage. In this article, a self-driven sensor based on the principles of triboelectric nanogenerators was used to measure the rotational slip of a tight threaded stud connection subjected to transverse cyclic loads. The finite element simulation was conducted on the contact slip in the stud connection in the experiment under transverse cyclic loading. It was found that local slip propagation with the increase of load cycles would cause no-constant-sticking-area slip on all thread surfaces and lead to loosening of the connection. Under a certain preload, only when the amplitude of the lateral cyclic load does not exceed a critical value, will the thread contact surface not experience local slip propagation. Therefore, a slip load coefficient was proposed for calculating the critical transverse cyclic load amplitude, and its influencing factors were discussed. This study provides a new approach for the anti-loosening design of threaded connections.