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A paedophile encouraged young girls to send him explicit photos before threatening to show the pictures to their parents or school if they refused his demands for more.
James Clark, 26, targeted his many victims online, often posing as a teenage boy as he sent and requested indecent images.
He would then attempt to blackmail the girls into sharing more photos, warning them the “embarrassing” material would be revealed to others if they rejected his sinister requests.
But one girl was brave enough to call his bluff, branding him a "creep with a phone" as she told him to "go ahead" and show the photos because it would land him in trouble "in the end".
Her words would prove prophetic as Clark, from Whitstable, was eventually arrested and last week jailed for more than five years.
Canterbury Crown Court heard his warped behaviour came to the attention of police in February 2021 when one 13-year-old girl he contacted while pretending to be 18 and via the Kik app was in fact an undercover police officer.
His home was raided and a phone, SIM card and hard drive found under his bed were seized for analysis.
On his mobile phone were more than 180 indecent still images of children and 15 videos. They depicted abuse across all three categorisations of depravity and on children aged between one and 10 years old.
Prosecutor Bridget Todd told the court officers also found incriminating chatlogs between himself and as many as 13 victims, many of whom said they were in their early teens and with one as young as 10.
He would send photos of himself and videos performing a sex act, saying he would take their virginity and help them "to learn", and incited the girls to engage in sexual activity themselves.
Telling the court how the sick pervert targeted one particular teenager, Miss Todd said he threatened to "tell everyone in her area and her school" about what he had seen of her.
"He said she had to do something for him and he would delete them. He tormented her and asked if she 'wanted this to go away?'," she added.
One of his victims, on revealing she was a lesbian, was sent a number of pornographic images of women and asked to perform a sex act.
Detailing the chat in which he was challenged and branded a creep, Miss Todd said he had initially asked a 15-year-old girl if she wanted to see 'what a d*** looks like' before sending an image.
"He asks if she likes it and if she would let him see her," explained the prosecutor. "He asks what she wants to learn and tells her he can help her.”
Referencing an image shared with Clark, the prosecutor continued: “He then tries to blackmail her, saying 'especially if you don't want that picture being sent around. I know people who will want it and pay me for it. So if you don't help me I'll send it'.
‘I'm not afraid of you because you are going to be the one getting into trouble in the end'...
"She replies 'Lol. You're a creep. Go ahead and send it. Lol. Go ahead. I'm not afraid of you because you are going to be the one getting into trouble in the end'.
"However, he tells her he would get a lot of money and her parents would see it.
"But she replies 'an old man threatening a young girl with sending a picture around. You're just a creep with a phone'."
The court heard Clark dared another girl, who said she was 15, to "show her boobs".
"She sent an image of a female in her underwear with hands covering her breasts and he dared her to do it without her hands, calling her a baby when she refused," said Miss Todd.
"He then made threats to post the picture she had sent online."
In response, the victim sent him an image of a different girl exposing her breasts. Clark later shared this photo with others online.
Following his arrest, Clark was charged and then on court bail when police seized two phones in January last year during a visit to his home.
When analysed, they found eight indecent images of children, which had been downloaded prior to his original arrest, as well as a more recent image depicting bestiality with a dog.
Miss Todd told the court he said that photo had been sent to him and, although he knew it was illegal and intended to alert police, he claimed his ADHD and autism "throws his mind off track".
Clark, of Walmer Road, admitted nine charges of attempted sexual communication with a child, four of attempting to cause a child to watch a sexual act, two of attempting to incite a child to engage in sexual activity, four of making indecent photos of a child, one of distributing indecent photos of a child and one of possessing extreme pornography.
The court heard he faced only "attempted" offences because the identities of his victims, other than the undercover officer, had not been established by police and confirmed as children.
Clark, who sat in the dock with his head bowed during the sentencing hearing on Friday, was said to be ashamed of his "appalling" offending, much of it committed between December 2020 and March 2021.
John Barker, defending, told the court it was committed at a time when he felt "isolated" and was going through a "very unusual and challenging" period, including family illness and being the victim of an abusive and toxic relationship.
But on jailing Clark for five-and-a-half years, Judge Simon Taylor KC said many people experienced problems in life without resorting to such criminality.
"The offences have been charged as attempts because police have not been able to identify the persons who received your communications," he told Clark.
As for the fact you were going through a difficult time and felt isolated, I feel sorry for you. But adults go through difficult times and the vast majority don't resort to sexual offending...
"But your intentions were clear. You intended to communicate with children and in some of those communications you resorted to coercion, threatening to blackmail them if they did not do what you wanted. You threatened to disclose embarrassing information.
"You also took your offending further by either attempting to incite them to engage in sexual activity or cause them to watch sexual acts.
"I don't know if any of the recipients were children or not but sentencing has to reflect that you intended to create 13 child victims.
"As for the fact you were going through a difficult time and felt isolated, I feel sorry for you. But adults go through difficult times and the vast majority don't resort to sexual offending.
"I take into account you were struggling but as a grown up you need to behave better, and the behaviour you engaged in involved a concerted effort to abuse children."
Clark was also handed an indefinite sexual harm prevention order and sex offender notification requirement.