I'm not very smart, so maybe I didn't explain it very well. When I first deepthroat/have anal sex with a whore, I don't even get a message that it was her first time; usually girls say something like "you should feel privileged that you're my first" or something like that. I suspect that once you ask a girl to be your whore she is no longer a virgin.
Also, if you have a whore that you blackmail with a sextape, you still have an option to arrange a setup, but even after you do, you have no option to demand that money.
If you have a -100 relationship with someone, for example after bullying, and then offer them a dose, relationship will be 0.