Ross Brogan, 31, bombarded four teenagers with indecent communications and obscene videos, then offered payment to reciprocate.
The Crown Office and Procurator Fiscal Service (COPFS) said the software engineer, from Glasgow, befriended the boys via Snapchat and quickly tried to exploit their friendships for his own gratification.
Prosecutors told the city’s high court how he demanded intimate images and videos of the youngsters – all aged under 16 – in return for Xbox or PlayStation codes which would allow them to make purchases via their games consoles.
In his sentencing statement, Judge Bruce Erroch KC said Brogan adopted an assumed identity on social media and contacted a boy he personally knew.
The judge stated that the worried victim confided in Brogan, unaware he was behind the sexually explicit requests.
Judge Erroch said it culminated in Brogan committing oral rape on the boy.
The judge stated: “It is difficult to conceive of a more calculated course of deceit and manipulation.”
COPFS said Brogan also left sex toys at a pre-arranged drop-off point, instructing that they be used in indecent photos and footage which should be sent to him.
Judge Erroch noted how he also threatened to hurt one of the boys and his family if he refused to obey his twisted demands.
Brogan pleaded guilty to six sexual offence charges at the High Court in Glasgow last month.
He was handed an extended sentence at the same court on Tuesday, with 10-and-a-half years in jail and an additional three years on licence once released back into the community.
The judge acknowledged his lack of a criminal record and apology, but said the harm caused to the boys was “significant”.
He told Brogan: “You are a mature man who chose to act as you did.
“Your actions were clearly planned, were calculated and were the opposite of spontaneous.”
Brogan was also banned from contacting his victims and had his name added to the sex offenders’ register indefinitely.
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Procurator Fiscal Faye Cook branded Brogan’s behaviour “predatory and despicable”.
She added: “He targeted young boys and exploited them for his own depraved ends.”
Detective Inspector Stephen Palmer said: “Brogan is a depraved sexual offender who gave no thought to his victims, just using them for his sexual gratification.
“These boys have been deeply impacted by his actions and I hope this sentence brings them some comfort.
“I want to acknowledge the strength of all who provided information to police in this case. Brogan’s conviction is down to them.”
