When two men decided to go onto a same sex dating website their lives were destroyed.
For laying in wait on FabGuys.com was Sam Shepherd, who met both and told them he would expose them as paedophiles unless they loaded him with cash.
Thanks to his relentless, aggressive pressure - in one case lasting months - the men handed him a total of £40,000, Bristol Crown Court heard.
Shepherd, 28, whose address was given as Kent Street, Portsmouth, pleaded guilty to two charges of blackmail.
Judge Michael Longman jailed him for six years.
He told Shepherd: "Blackmail is one of the ugliest and vicious crimes in the calendar of criminal offences.
"It is regarded by members of the public with loathing and contempt."
A hearing under the Proceeds of Crime Act was set for September 21 to claw back Shepherd's ill-gotten gains.
Charley Pattison, prosecuting, said Shepherd met the first victim and claimed he would expose him for communicating to a child - something the victim denied.
The court heard Shepherd took the victim to a hotel and then to a casino, where the victim gave him money.
So began months of repeated demands for cash from Shepherd, including for the financing of a Peugeot car.
Each demand was supposedly the last - until the next one - and Shepherd grabbed a total £30,400.
Shepherd targeted a second victim in a similar way and managed to get some £10,000 off him, though a £6,000 transfer was cancelled.
In this case the traumatised victim revealed his "bi-curiosity" to his parents and moved from Bristol for fear of being attacked by Shepherd or his associates.
In total Shepherd had managed to get some £40,000 from the two men, Miss Pattison told the court.
Nicholas Clough, defending via video link, said: "He started off as paedophile hunter.
"Financial gain became a possibility and he grasped the opportunity with both hands.
"Second, he was badly in debt at the time.
"Third, this was a fundamental lesson to him. He will not behave in this way again."
Mr Clough said his client was being medicated for mental health problems, hated prison and was resolved not to return on his release.
He added that Shepherd had £20,000 available to return to the victims.
