We can see Jesse's asshole clinging to his big thick cock shaft on the out-stroke suggesting her ass hasn't surrendered to his cock and accepted the arse fucking. Instead her anal sphincter has clenched around his cock resisting the fuck. Poor Jesse this is painal for her but like a pro she makes it through the scene. Gotta say as a guy fucking a clenching asshole feels great so I can understand why he keeps going even though he should have stopped or at least lubed her more and maybe fingered her arse to help her open up