Richard James Altham, 29, of Greenset Close, Lancaster, previously abused two very young girls as a youth.
Then, in December 2018, he was given a 10 year sexual harm prevention order (SHPO) controlling his access to children and to the internet after being stung by a group of "paedophile hunters" called Fleetwood Enforcers.
Despite the strict terms, earlier this year, an undercover police officer posing as a 13-year-old girl was approached by Altham after creating a profile and chat thread on Kik Messenger - a notorious app that allows users to preserve anonymity by allowing them to register without personal details such as a mobile number.
Prosecuting, Simon Blakeborough said the conversation moved onto Skype, where Altham was told she was 13.
He said: "The defendant has a number of previous convictions which are of concern.
"An undercover officer created an online profile posing as a 13-year-old girl on the Kik messenger service.
"The undercover officer opened a thread with the defendant.
"On January 15 the defendant was informed clearly that she was 13 and from Liverpool. He confirmed he was 29 and lived in Lancashire.
"The defendant asked for a full body picture and sent two photographs of himself. He asked if there was 'any chance of a nude'?
"He stated they could be really good friends but she could not tell her parents.
The court heard Altham asked for 'naughty pictures' of the girl and sent her lewd pictures of himself performing sexual acts.
He asked if she would like to be his girlfriend and engaged in further sexual conversation.
At one point when arranging to meet her asked her to "bring a friend" and said they would "all have a good time watching films and having sex."
He also sent her a fully naked picture of himself and told her this was the type of photo he wanted from her.
Later, he told her which trains to catch to meet him.
He was arrested waiting at Morecambe Railway Station for her.
He admits attempting to sexually communicate with a child, two of attempting to cause a child to engage in sexual activity, attempting to arrange the commission of a child sexual offence, and attempting to meet a child following sexual grooming.
He also admitted attempting to breach the SHPO by attempting to communicate with a girl under 16, and four counts of breaching it by his use of internet enabled technology.
The offences put him in breach of a suspended jail term for a previous breach.
Defending, Mr Evans said he had accepted the purpose was sexual gratification, while many other defendants try to minimise their actions or simply deny it.
He added: "This defendant has consistently said he wants to get help."
He also revealed his conduct had split his family - with some siblings having "moved away" from him while other relatives are trying to support him.
Recorder Mark Ainsworth jailed him for four years and imposed a new indefinite SHPO.
He accepted his initial conviction was many years ago, but added: "It is the start of a sequence of events over a number of years which lead you to be sitting before the courts this morning.
"You knew you shouldn't be talking to her."
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