My apologies for adding the bit about the cop breaking the law, which really has little or nothing to do with entrapment. I wouldn't go as far as to use a "gun to the head" analogy though.
Here's one case, Sherman vs. United States
http://en.wikipedia.org/wiki/Sherman_v._United_States
Quote:
In late August 1951, Kalchinian, a recovering drug addict, met Sherman at a doctor's office where they were both getting treatment for their addiction. They talked about drugs, and Kalchinian eventually asked Sherman if he could get him some as his own methadone program wasn't working. Sherman resisted, citing his own efforts to get clean.
On later chance encounters, Kalchinian continued to entreat Sherman, encountering similar resistance. Finally, in November, he gave in. Kalchinian informed agents of the Federal Bureau of Narcotics (a predecessor to today's Drug Enforcement Administration) whom he had been working with in hopes of lightening his sentence on a pending drug charge, that he had another seller for them. After three drug deals, Sherman was arrested.
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Prostitution is even worse, because desperate guys are desperate guys, and guys think with their penis, not with the rational of the law.
I disagree with you though when you say presenting illegal opportunities many times is not entrapment. Like in the case of the Sherman vs. United States, even strong-willed people who want to focus on rehabilitation will give in eventually if pressured enough. If a prostitute goes up to someone's car and offers sex, and they say no repeated times and then they finally say yes, I think it could be argued on psychological grounds that they were pressured and thus it is sort of entrapment.
Now I'm of the opinion that 9 out of 10 times people who get arrested for prostitution charges are LOOKING to have sex with a prostitute, but I bet you get the occasional jackass, wrong place, wrong time, pressured by the undercover cop situation.
Anyway, I agree 100% with the letter of the law, which is innocent until proven guilty.