Remember that resonance structures are not completely accurate representations of the electronic structures of molecules. The true structure of the molecule is a hybrid of the resonance structures.
In your example, both the methylene carbon and sulfur will be sp2 hybridized, and the p-orbitals from these two atoms will overlap to form a pi bond. However, the electrons in the pi-bond will not be equally shared between the two atoms. As implied by the two resonance structures, the electrons will sometimes be very near to the sulfur while other times they will be equally shared between the sulfur and methylene carbon.