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Judge Lady Poole praised the bravery of the four young women as she gave their attacker Dillon Anderson,21, a nine year prison sentence.
He raped the young women during a horrifying campaign of abuse which he began when he was just 14-years-old.
The High Court in Edinburgh heard how Anderson throttled two of his victims during the assaults. One woman - a former undergraduate of Edinburgh University - said Anderson repeatedly caused her to pass out after compressing her neck. On one occasion, he was so scared that he had killed her, he checked her pulse.
Jurors heard how he Anderson wanted her to take part in rape role plays where she would be unconscious and he would do whatever he wanted.
Describing one occasion, she was throttled, the woman - who is now aged 23 - told police: When I came round, he was checking my pulse and he said I thought you had died. He looked panicked.
One of the woman also made a covert recording of Anderson attacking her - the sounds of her screaming and telling her assailant to stop were played to jurors. Anderson could be heard laughing manically as he ignored her pleas.
The story emerged after Anderson - a former resident of Edinburghs exclusive new town area - was found guilty earlier this year of raping the women, who cannot be named for legal reasons.
On Tuesday, judge Lady Poole told Anderson that his conduct was disturbing - she also ordered the authorities to supervise him for four years following his release from custody.
Passing sentence, Lady Poole told him that she had read statements from the women detailing how Andersons conduct has affected them.
She added: The sexual violence you perpetrated is disturbing. One of your victims spoke to losing consciousness because of you compressing her neck.
When she came round, there were times you were having sex with her. There were other times when she came to, and you said you thought shed died and laughed, or you were checking her pulse because you thought she might have died.
These were terrifying experiences. I have read victim impact statements. Your victims suffered grievously at your hands, and their contact with you has left them with long lasting emotional scars.
They are to be commended for having the courage to come forward, and go through the difficult experience of giving evidence about what happened to them.
Anderson committed his offences between May 2014 and January 2020.
During the trial, the court heard Anderson claim he was a virgin when he physically restrained a girl, who was then aged 14, at a house in Newtongrange, Midlothian.
The court heard how he forced her to lie on a bed and removed her clothing before raping her on an occasion between May 2014 and June 2014 .
On various occasions between August 2015, at addresses in Edinburgh and West Lothian, Anderson raped another girl who was aged 18.
Anderson then repeatedly raped the Edinburgh University student - who was aged 19 - between September 2017 and December 2017.
The court heard how Anderson often choked her during sex.
Jurors heard extracts from statements she gave to the police.
She told detectives: He would use a lot of force and I kept saying get off. I tried to grab his hands and continue. He would squeeze my throat and I couldnt breathe.
I dont know how long it went on for. But I got the same feelings as before the fuzziness and everything.
I started thinking is that what dying feels like.
Some of the times he did this to me, he would say I actually thought you had died and he would laugh. I eventually passed out.
As he strangled me, I lost complete consciousness. I am not sure how I had lost consciousness but when I came around I was really sore. It was intense pain.
The young woman also told the court of how Anderson subjected her to unwanted attention and had bombarded her with unwanted phone calls and social media messages.
Anderson also preyed on another woman between December 2018 and January 24 2020. The court also heard how he also throttled this woman, who is now aged 24, before raping her.
During the recording which was played to jurors, the woman was heard crying and repeatedly screaming get off of me. Anderson can be then heard telling the woman: breathe, breathe, breathe and breathe in, breathe out and inhale, inhale, inhale.
The woman can be heard to ask: What are you doing you f***ing psycho? Anderson was then heard laughing.
On Tuesday, defence solicitor advocate Iain McSporran QC told the court that Anderson had started to appreciate how his actions had affected his women.
He added: There is the beginning of an acknowledgement on his part. There is an insight on his part into how his conduct affected the complainers and how it was utterly inappropriate.
These are perhaps the beginning of rehabilitation.
Passing sentence, Lady Poole also placed Anderson on the Sex Offenders Register for life. She also ordered that Anderson not contact his victims for 25 years.
She said: Your victims have suffered long term effects from what you did to them, and deserve to be protected from you.