(summary) I am a escort on Backpage. I have been posting online for months. My ad states that anyone that wants to meet me must send a pic and picture of their penis. Can a cop do this? Or do they try to avoid sending those types of pics since they are trying to be undercover?
A couple of interesting points.
First, you have to be careful how you ask your question. Essentially, you could just be asking for someone to help you break the law regarding solicitation for sex. That's a problem for everyone, including yourself. The most obvious answer is -- don't break the law. If the jurisdiction where you "practice" outlaws prostitution (or advertising online), don't do it.
Now, having said that, your question about what the police may or may not do in an undercover operation can be answered without directly advising you on how to break the law. The government is free to pose and act (even in an illegal manner) in order to "catch" someone in the process of breaking the law. Examples include "paying" for drugs, and setting up child-sex meetings by posing as a child online. These are common examples most people would be familiar with. However, other more subtle examples exist. Take for instance the "informant" that infiltrates a conspiracy to sell cigarettes across state lines without paying taxes, or a "runner" who delivers messages between smugglers. You get the idea. In summary, a police detective or officer could absolutely pose or send you pictures in order to get you to incriminate yourself.
What the officer cannot do is initiate the illegal activity him/herself. For example, the police officer could not approach you and say, "hey, you wanna have sex for money?" That's called entrapment. While there are some exceptions to this (for ongoing investigations where an underlying warrant or probable cause already exists for the conduct), as a general rule, the cop can only respond to what you do, not initiate.
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