So, my first response to this Ask was to think, “Well, it’s already been established that these two have gotten physical with each other.” At first I thought maybe it’d be funny to have Jessie admit that she gives it up to easily for her to use sex as a bartering tool, but then I remembered that, like, catching Pikachu isn’t the problem. Team Rocket catch Pikachu more often than not, the problem is he always gets away. So then I thought, you know, maybe Jessie has tried (repeatedly) to sex Pikachu away from Ash, but Pikachu still escapes so Ash is basically just tricking her into fucking for nothing each time. That seems pretty in-character to me. The fact that Jessie would keep trying that tactic despite not getting the results she wants is kinda on her at this point.