He threatened to reveal the young woman's sexual history if she did not disclose further details of her sex life to him.
In one text message he said: "This is your last chance. If you reply to this message with anything besides what I asked or if you don't reply at all then I'm going to expose you."
The man told police he knew what he was doing was wrong, court documents state, but hearing about the women's sexual encounters was "my thing".
He was this morning sentenced to 350 hours of community work and 12 months supervision.
Judge calls man "despicable"
In Auckland District Court today, Judge Nevin Dawson told Crago his actions were "despicable" and had an "element of sadism".
"To use social media in this way to trap people into communicating with you, forcing people to communicate with you by threats, is something you surely should be ashamed of," he said.
The women, whom he first befriended on social media, became scared for their safety when he turned nasty, Judge Dawson said.
When they refused to answer his questions about their sex lives and sexual preferences, and tried to break off contact with him, he "began making threats".
The two women's victim impact statements were "revealing", Judge Dawson said.
"They said they find it hard to sleep. One says she began to feel paranoid she was being followed by you.
"They were both scared that they would no be left alone by you. One was scared for her safety and that you may find and hurt her."
While this might not have been Crago's intention, he said, it was "hardly surprising they would feel that way".
Crago's lawyer Meg Scally said he had shown "significant remorse and considerable insight" about his offending, and had written letters to the court and both victims.
The court could have "some confidence that he is well aware of how bad is offending was and that he will not place himself in that situation again", she said.
Crago was a young man who was isolated and his behaviour was "indicative of someone who struggles with interpersonal relationships", she said.
Judge Dawson said he believed Crago's remorse was genuine, and that, combined with his early guilty plea and lack of criminal history, he was persuaded not to impose a prison sentence.
Instead, Crago was ordered to serve 350 hours of community work and 12 months supervision. His cell phone was also ordered to be wiped clean.
Turning to Crago, Judge Dawson told him the sentence was based on his belief he was "unlikely to see you back here [in court] again".
"If you do, the sentence will not be what you have today."
