A male model sent his victim a WhatsApp message to confess he had raped her.
Jamie Hillen, 35, repeatedly preyed on the woman while she was asleep.
The predator struck at flats in Glasgow's Knightswood and Partick as well as another in Leith, Edinburgh.
Prosecutor Usman Tariq said the woman first got to know Hillen in 2013.
He then told the High Court in Glasgow: "On May 16 2015, she received a WhatsApp message from Hillen informing her that he had sex with her whilst she was asleep."
It was two days later that the shocked woman confronted her attacker.
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Mr Tariq: "They then had a verbal argument about this the following morning when she expressed her disgust about what he had done to her."
But, the court heard - from then until September 2016 - Hillen "regularly" had sex with the woman while she was sleeping and unable to consent.
The advocate depute: "She believed that Hillen felt entitled to have sex with her...and she did not feel confident enough to tell him to stop due to the fear that he would become violent."
The victim stated Hillen "liked to be in control".
She added: "It was not worth it for him just to become violent towards me."
The court was told Hillen had also sent another WhatsApp message with a photo of him performing a sex act next to the woman.
After being held by police, Hillen, still of Partick, admitted having sex with the woman while she was not awake.
Mr Tariq said the victim's "mental health and anxiety levels have been serious affected" by her ordeal.
On Thursday, Hillen was sentenced to five and a half years in jail.
He had previously admitted at a hearing in Airdrie to raping and sexually assaulting the woman.
Lord Beckett said: "The victim was badly affected by your conduct when powerless to stop it.
"It is necessary to punish you and to deter you and others from attacking sleeping women."
