We study the geometry of conditional optimal transport (COT) and prove a dynamical formulation which generalizes the Benamou-Brenier Theorem. With these tools, we propose a simulation-free flow-based method for conditional generative modeling. Our method couples an arbitrary source distribution to a specified target distribution through a triangular COT plan. We build on the framework of flow matching to train a conditional generative model by approximating the geodesic path of measures induced by this COT plan. Our theory and methods are applicable in the infinite-dimensional setting, making them well suited for inverse problems. Empirically, we demonstrate our proposed method on two image-to-image translation tasks and an infinite-dimensional Bayesian inverse problem.