A serial sex offender who took part in the gang rape of a 15-year-old girl has been jailed for 12 years for a spate of attacks spanning more than two decades.

Hugh Derby, 52, indecently assaulted and raped the schoolgirl with others while she was intoxicated through drink and drugs at a flat in East Ayrshire in 2000.

He sexually assaulted another woman in 2011, and two years later he attacked a 12-year-old girl.

Derby grabbed and struggled with the youngster, lay on top of her, and kissed and pressed himself against her.

He targeted the girl once more when she was 15, molesting her at a Calvin Harris concert at Bellahouston Park in Glasgow in August 2015.

One woman was attacked by Derby in 2013 while on a camping trip in Dumfriesshire. She awoke in a tent in the middle of the night to find Derby sexually assaulting her.

And in 2019, he sexually assaulted another victim by scratching her back and squeezing her buttocks.

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One woman, who woke up on a couch to find Derby abusing her, said: “I kicked out. I wanted to kill him. I couldn’t believe he would hurt me like he hurt me.”

Derby, of Auchinleck in East Ayrshire, denied a series of charges during an earlier trial but was found guilty of four offences of sexual assault, one of sexual activity towards an underage girl and one of indecent assault and rape.

He claimed that some victims had consented and that on other occasions the offences did not take place at all.

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At the High Court in Edinburgh on Tuesday, Thomas Welsh KC said: “You have been convicted by the jury of grave and serious charges.”

The judge pointed out that three of those subjected to abuse by Derby were asleep or incapacitated at the time.

He said: “You clearly acted in a premeditated and predatory manner, identifying and isolating your victims when they were most vulnerable and unable to resist your approaches.”

The judge added: “These were all shocking violations of the sexual autonomy of your victims.”

As well as the 12-year jail sentence, Derby will be supervised for three years upon his release from prison.

He has also been added to the sex offenders’ register indefinitely.

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