A Mansfield man was jailed for 28 months for seeking sexual kicks by trying to persuade boys to pose naked on the internet.
Nottingham Crown Court heard of 22 young victims, one as young as 14 and another only a year older.
Keith Pell, 52, was put on the sex offenders' register for a decade.
He admitted 22 counts of attempting to incite the exploitation of a child between June 2016 and August the following year.
Judge Steven Coupland told him: "The conclusion of the probation service is that you are a high risk of re-offending. I endorse that view.
"For a period of 18 months, you repeatedly contacted boys under 18 for the purpose of sexual gratification."
He said the offences were made worse because two boys were 14 and 15.
The judge noted that the offences were committed at a time when Pell was caring for his mother before her death but added: "It is not an excuse."
James Baird, prosecuting, said that Pell was traced after he contacted a known paedophile in Surrey, saying that he had 200 pictures of boys aged between 11 and 16.
A Canadian website dealing in "sexualised chat" was used by Pell, of Carlton Street, Mansfield, who once called himself "Keith Sexy" on the internet.
Mr Baird told the court: "He asked whether they could have fun together in front of the camera. He said that he needed cheering up."
A boy responded, said he was 16 and asked "if this is too young".
Mr Baird told the court: "He says 'okay' and asks him to dress in his sister's clothes. He tells him to 'get naked on the camera'."
Calling another victim "sexy", Pell went on to "ask whether he would be his online boyfriend", added Mr Baird.
Joe Hingston, mitigating, said that the offences related to only 22 out of 90,000 times that Pell had accessed the internet.
Referring to the other internet links, he told the judge: "These were not connected with the sexual abuse of children."
And he said that there was no evidence of "any impact on any individuals," saying that those contacted might not have been under 18.
"They could possibly be older men masquerading as younger men on the internet, which is not uncommon," said Mr Hingston.
At the time, Pell was caring for his dying mother. Mr Hingston added: "He is someone who is very lonely and very desperate for company."