If you don't misrepresent yourself, chats shouldn't be an issue in most locales, HOWEVER if you send photos to a 14 year old boy posing as a45 yr old to play your "Daddy", that could lead to a world of trouble. Especially if that 14 yr old boy is sitting next to a cop. Entrapment? Sure. But do you want to deal with it? Especially if it's at the federal level? The feds can always afford more attorneys than an individual unless your real name is Melissa Gates. Usually the cops pose as 14 yr old girls to snare 45 yr old males; I wouldn't put money on them either way.