I used to live in East Boston (Eaz Bastin in case you're from that area).

On my way home from work there was a street corner where the hookers hung out. One night I was driving home and I noticed they actually looked hot this time. I mean really hot. I almost stopped.

The next day I found out there was a sting on that corner that night. After that, I could always tell when there a sting operation going on.

So a good rule of thumb, if you're in Boston and the hookers are hot, it's a sting.

Pimps only came into existance when hookers needed protection from the legal system.

That said, the doctor is a moron, you got caught, just own it, you probably woulda been able to keep it quiet had you not made an excuse that practically writes the newspaper headline itself.

Actually the cops always go after "respected" members of the community as it gets headlines.  Except it backfired when they tried that in Brisbane and the doctor had a tape recorder and recorded the conversation.  You see previously he had walked down the street, been propositioned by an undercover cop, told her no and been charged with solicitation.  She lied in the court and he was convicted.  After that he carried a tape, well he was a doctor so they usually have one anyway, and the next time it happened he played it in court.  The female cop followed him down the street harassing him not taking no for an answer.  The cops loudly announced this guys name all over the news ruining his reputation.  Of course when he was proven innocent nothing happened to the cops. 

Common tactics for Brisbane police though.  Some guy on the way to an ATM was propositioned, told her no thanks, then unbeknownst to him she followed him into a 7-11 and when he got money out from the ATM machine, the undercover cops swarmed all over him.  Getting money out for a night on the town was proof of intent.

I know in the US they pull the same stunts.  You had that couple who were flagged down by a motorist in distress.  She turned out to be an undercover cop who was flagging motorists down then charging them with solicitation.