A Leicester man who wrote a woman online looking for friends fell victim to a serial blackmailer.
After discovering the news on the Craigslist website, the man sent a message to a woman he considered a woman.
The conversation went to Whatsapp and she asked if he had any naughty photos.
He sent a picture of himself shirtless and she sent an intimate one of her.
He sent a picture of his private parts and they continued to exchange flirting messages.
An end to the conversation, however, was led by a man from Cleethorpes.
Paul Snelson, 23, was behind the scam, reports GrimsbyLive.
Snelson sent a message saying, "I'd like to get paid £ 200 as soon as possible, or all of that goes on Facebook / Instagram in every newsgroup in Leicester. I have 14 different accounts and will post you anywhere.
"I've also added all of your 351 friends to a group message, and they'll see the post as well."
The man sent 200 pounds to the account. He was asked for another £ 200, but did not answer.
Details of the case were reported in court after Snelson admitted eight cases of blackmail he had made online as a woman on Craigslist and other websites.
During the online conversation, Snelson openly engaged in sexual conversation with these men and shared pictures of women of a sexual nature whom he had taken from the Internet.
After receiving similar pictures of the men, Snelson immediately began to demand money and threatened to put the pictures and content of the interview online if they were not paid.
At the Grimsby Crown Court this week, Judge Peter Kelson QC described this as "a very serious case".
Another eight offenses were taken into account. Snelson has been detained for three years and five months.
Detective Constable Nichola Oakley of the Humberside Police Major Crime Team said: "Paul Snelson blackmailed these individuals who truly believed they spoke to women and had intimate conversations with them.
"I want to thank these guys from all over the UK for having the courage to get in touch and alert us to Snelson.
"I believe that if they had not turned to the police, Paul Snelson would have believed he could threaten and embarrass even more men by paying him to remain silent."
"He said he would publish the pictures, contact details and false stories about the victims on social media sites so they could be seen by their friends and family.
"We tracked Paul Snelson using his own bank data, which he foolishly sent to the men to deposit cash. We examine other transactions found in this account.
"I would like to warn everyone who participates in online dating or chats to check which details or pictures are sent over the Internet. The person they are talking to may not be what they seem to be.
"Anyone can be the victim of unscrupulous people like Paul Snelson, who only wanted to benefit from deception, threats and aggression. His actions struck him, who has now landed him in jail.
"I would like to encourage anyone who believes they are victims of extortion to turn to us."