Temporal non-analyticities in the rate function of the Loschmidt echo manifests a class of dynamical quantum phase transitions (DQPTs) that has emerged as a powerful framework for understanding far-from-equilibrium many-body dynamics. While such DQPT has been extensively studied theoretically in spin-boson systems such as the Dicke model, their experimental observation remains elusive. In particular, the dynamics of DQPT in asymmetric spin subspaces and under the influence of spin dissipation are largely unexplored. Here, we report an experimental study of temporal DQPT in a generalized Dicke model using a trapped-ion quantum simulator. By coupling a linear chain of
40Ca+ ions to a collective center-of-mass motional mode, we probe the quench dynamics starting from both symmetric and asymmetric initial states. We extract the rate function and identify temporal turn-around points that are in quantitative agreement with theoretical predictions. Additionally, we investigate the impact of spin dissipation on these dynamics. Our results establish an experimental platform for probing complex many-body out-of-equilibrium phenomena and advance the development of hybrid oscillator-spin quantum simulators.