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When a guy asks a girl to "send nudes", a girl has two options. She can either trust him and believe that he won't ever hurt her by exposing her to the entire world. Or she could hold back and risk being called names or worse, being dumped.
There's nothing wrong with "sexting" or sending pictures to someone that you love. It's an intimate form of communication and showing love. But we never know if and how the relationship is going to end. Sometimes you can be so in love but then when it ends, be so in hate.
So how can you really tell when you should send it or not? You can't. The only way to know is to ask yourself if you trust the other person. But at the end the of day, even if you trust the other person, they can still disappoint you.
So what you really need to do is to to ask yourself, "What would I do if my pictures are leaked?"
And? What would you do?