After finding her teenage son in bed with the town scamp, an overprotective mother hires a prostitute to pose as a student at her sons High School in an effort to lure him away from his budding new romance. But when the son falls for the alluring money hungry prostitute things quickly spiral out of control.

Thanks Tor - you've managed to do something that I'm struggling with, which is keeping the logline to just one sentence.

Have you considered using the prostitute as you main protagonist ??

In the logline, the mother and son are passive and the prostitute is active.

"Contacted by a militant mother, a greedy prostitute attempts to pose
as a high school student to break up the budding romance of her boss' son."

Definitely a comedy. Why not go for irony: the smother-mother "rescues" her son from the "town tramp", only to get involved in an torrid affair with a low-life gigolo herself.