Dreaming of a prostitute often suggests a hidden sexual need. Often, dreaming of a prostitute forces us to look at our own sense of guilt or uncertainty about ourselves.
A pimp is one who procures business for a prostitute and this has obvious resonance in the business world.
To be paying a prostitute may suggest that we do not trust our own abilities, sexual or otherwise.
To be paid for the sexual act may suggest that we feel relationships will cost us.
In both cases there may be a fear of loving relationships.