The girlfriend of a man who was raped and murdered by strangers has spoken of the horrific moment she realised their new-born baby would ‘never know her daddy’.
Calum Simpson, 24, died after being spiked with the Class C drug Etizolam by depraved killers Dylan Brister, 27, and Cameron Allan, 21 in November 2021.
The twisted pair bound the father-of-four’s wrists and raped him as he lay dying in Brister’s home in Fife, Scotland.
Calum’s partner, Bobbie Cowan, had given birth to their daughter just 11 days before the horrific murder took place.
Now the 26-year-old, who has been left to raise four children on her own, has spoken about the ‘horrific nightmare’ she has been trapped in ever since.
She told The Sun: ‘My world fell apart when the police came to tell me he was dead.
‘When I found out he’d been attacked and raped, I was sickened. He must have suffered so much.
‘The children and I miss him terribly. They each have a teddy bear which has Calum’s voice inside, saying: 2I love you and I will see you soon.’ It breaks my heart”.’
Calum’s partner, Bobbie Cowan (left), had given birth to their daughter just 11 days before the horrific murder took place
![Depraved killers Dylan Brister, 27, and Cameron Allan, 21 pictured in a music video they filmed before the murder](https://i.dailymail.co.uk/1s/2025/02/09/18/91420205-0-A_second_video_also_shows_Brister_staring_at_the_camera_while_li-a-5_1739126926328.jpg)
Depraved killers Dylan Brister, 27, and Cameron Allan, 21 pictured in a music video they filmed before the murder
Ms Cowan, who first starting dating Calum when they were teenagers in 2015, said she will ‘always regret’ the pair’s last conversation with each other.
She said when he went out that night they had a few words with each other and ‘left on a bad note’.
The 26-year-old also spoke of the heartbreaking moment police told her that Calum had been murdered.
She said she was holding her new-born baby in her arms at the time and quickly came to the realisation that ‘she’d never know her daddy’.
Ms Cowan explained that she had taken a few photos of the three of them together in the hospital but this was now ‘all they had’.
Brister and Allan, who are believed to have been high on drugs when they murdered Calum, were both handed life sentences last year.
Brister was sentenced to a minimum 23 years, while Allan had 19 years imposed, with both having their details added to the sex offenders’ register for life.
The trial judge, Lord Harrower, told jurors after they unanimously convicted the pair of the sexual assault, rape and murder: ‘The evidence has been of the most harrowing nature that this court has ever had the misfortune to listen to.’
Advocate depute Angela Gray told jurors: ‘This is a plan between both accused to drug Calum Simpson to make sure he does not get up.
![Dylan Brister, 27, mouthing the words to an Elton John remix, which included the chilling lyrics 'cold, cold heart, just hours before killing a father-of-four Calum Simpson, 24,](https://i.dailymail.co.uk/1s/2025/02/09/18/91420143-0-Dylan_Brister_27_mouthing_the_words_to_an_Elton_John_remix_which-a-6_1739126934274.jpg)
Dylan Brister, 27, mouthing the words to an Elton John remix, which included the chilling lyrics ‘cold, cold heart, just hours before killing a father-of-four Calum Simpson, 24,
![Cameron Allan (pictured) was sentenced to 19 years in prison after being found guilty of murder](https://i.dailymail.co.uk/1s/2025/02/09/18/87550217-0-Cameron_Allan_pictured_sentenced_to_19_years_in_prison_after_bei-a-8_1739126965365.jpg)
Cameron Allan (pictured) was sentenced to 19 years in prison after being found guilty of murder
‘They drugged him for their sexual gratification. That drugging was wickedly reckless to the consequences and in so doing they had a complete disregard for the safety and the life of Calum Simpson.’
Graphic footage recovered from Allan’s phone was shown to a jury during the trial at the High Court in Edinburgh.
The judge said this clip was ‘a glimpse into the depravity’ and the dynamic between Brister and Allan.
During the footage Allan could be heard saying to his accomplice: ‘At least he is still breathing.’
The court heard that Allan and Brister had been seeking to recruit a man to make up a threesome with them but efforts to find a participant failed.
One man who met Allan at an inaugural Pride event in Dundee was told they would be ‘up for’ choking him and wanted to tie him up and abuse him but he chose not to become involved.
Ms Gray said: ‘And then Calum Simpson, a complete stranger, arrives by chance.’
Mr Simpson arrived at the house with a friend, Dylan Stewart, who knew the pair and later departed leaving him alone with them.
Ms Gray said: ‘There was no evidence that Calum Simpson had any homosexual tendencies.’
The court heard that Brister, who received almost £1,200 a month in benefits, had won more than £20,000 gambling and bought 1,000 tablets for £200.
He claimed that he believed they were genuine diazepam which came in proper packaging and a pharmacy carrier bag.
But Allan, who said he was at the drugs handover, said it was strips of drugs in a freezer bag and they came with a warning.
![In one video Brister was seen mouthing the words to Cold Heart by Dua Lipa and Elton John while dancing with Allan in a living room](https://i.dailymail.co.uk/1s/2025/02/09/18/91420141-0-In_one_video_Brister_was_seen_mouthing_the_words_to_Cold_Heart_b-a-10_1739127016172.jpg)
In one video Brister was seen mouthing the words to Cold Heart by Dua Lipa and Elton John while dancing with Allan in a living room
He said the woman supplying them warned Brister they were strong and added: ‘That’s why she gave the warning, someone had already died from taking them.’
Forensic evidence indicated that glasses, including a champagne style flute and skull shotglass, were spiked with Etizolam before the victim drank from them.
An experienced medical examiner who saw the injuries inflicted on Mr Simpson told the court: ‘If the person was awake and fully conscious it would be very painful.’
The court heard evidence that Brister had previously spiked the drink of a woman with diazepam in 2018 and put tablets in the mouth of another without her consent.
Brister told the court he suffered from complex post traumatic stress disorder and a personality disorder and received anti-psychotic medication.
Brister said: ‘We raped him and continued to have sex. It is what it is, disgusting. It should never have happened. I am not going to make excuses,’ he said.
Allan told police that he had ‘bad sex thoughts’ because he what happened to him when he was younger and added: ‘This is the first time I have acted on those thoughts.’
Allan said he was in love with Brister but claimed the older man ill-treated him. He said: ‘I was treated more like a dog than a servant. He was just a violent, angry man.’