Ian Alexander Jubb, 24, offered the youngster money and asked him to send pictures of himself during internet chats.
Jubb’s exploitation of the under-age teen occurred while he was on a community order for a similar grooming offence.
Jubb appeared at York Crown Court on Thursday after pleading guilty to contravening a sexual-offences prevention order and three breaches of police notification requirements.
He was brought up from the cells to be sentenced on two indictments including eight counts of making indecent images of children.
Prosecutor Nicoleta Alistari said that in January 2015, the boy’s parents, who live in Wales, reported Jubb to police after discovering the online chats.
She said Jubb had blocked one online account but set up another under a different name, on which he sent the boy messages and Christmas cards. He told the boy he was 19 years’ old and drove an Audi with a personalised number plate.
Jubb was jailed for four years, placed on the sex offenders’ register for life and made the subject of a sexual-harm prevention order, to run indefinitely.