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Khan, of Morley Street, Bradford, pleaded guilty to two offences of having sex with the girl.

Ahmed has a conviction for indecently assaulting a girl of 13 in his car after plying her with alcohol.

He was jailed for 30 months in 2005 and ordered to sign on the sex offenders’ register for life.

Judge Jonathan Durham Hall QC said yesterday the men’s victim was from a respected, traditional, Asian family.

One of her abusers had given her chlamydia and Ahmed threatened to petrol bomb her family home if she or her sister told on him.

The men were arrested when the girl’s pink bra was found in Khan’s bed and a bag containing her school uniform at his home.

The judge told Ahmed he had turned “a bright, successful, confident, girl” into “an appallingly damaged child”.

“You are a dangerous, predatory paedophile, targeting, watching and abusing vulnerable children,” he said.

Ahmed turned up at Lister Park, Manningham, Bradford, in the summer of 2010 in one of his expensive cars and “chatted up” the schoolgirl and her older sister.

He groomed the young girl, who looked only nine or ten, until she thought of him as “her very best friend”, said the judge.

Ahmed took photos and made videos of his sex acts with the girl and took her to places where there were only adult Asian men present.

One phone video showed him trying to persuade her to strip off in front of other men.

She went missing for days on end and Ahmed took her out of school.

“You took her virginity and cleverly and wickedly manipulated her,” Judge Durham Hall said.

“Your arrogance is startling as indeed is the depth of your depravity.”

Sentencing Khan, Judge Durham Hall acknowledged that he did not corrupt the girl or ply her with alcohol and cigarettes. He also had no convictions for any similar offences.

After the case, Detective Constable Jazz Gill, of Bradford South CID, said: “This case indicates our continued determination in removing those within our communities who prey on the young and vulnerable.

“Ahmed and Khan both used their position of trust as an adult to take advantage of their victim.

“Both have reached the depths of depravity in their actions and I hope today's outcome offers some justice to the families involved.”