Generally speaking, yes. I'm going to move your post to the Criminal Defense practice area as you are more likely to get responses there.
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Probably can't get in trouble just for asking....unless he was really coercive or something, but he could certainly get in trouble for possessing a "dirty picture" of anybody under the age of 18. It's not safe for you to be communicating with a person like that.
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I don't he can get in trouble for asking, butbhe can be arrested and charged with felonies for possession of child porn. You should definitely stay away from anyone asking for that. Additionally, even if you were inclined to provide pictures like that, do you really want that out there, which could come back to haunt you at any time in the future.
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He could theoretically be charged with Endangering the Welfare of a Child.
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