Jake Mills, 21, sexually assaulted and tried to rape his first victim - a young woman in her 20s - then exposed himself to two female pensioners while under investigation.
All three attacks happened on Chesterfield streets.
Judge Nirmal Shant QC said Mills targeted the two elderly women because they were “more vulnerable” and he posed a “significant risk” to lone females.
The court heard a psychological report found Mills had a “very low IQ” however Judge Shant added that provided “no explanation” for what he had done.
During the first incident in November 2020, Mills followed a young woman into an alleyway at around 5.40am, began kissing her and tried to force her to perform oral sex.
However the court heard while Mills was released on bail under investigation, he exposed himself to two elderly women on the same day.
And the same morning he had followed a young woman in his car while she was jogging in Tapton.
Judge Shant, speaking about the November 2020 attack, said: “This was an attack on a lone female in the street in the early hours of the morning.
“Suffice to say it’s had a profound impact as statements describe her misery - she suffers panic attacks, loss of confidence, anxiety and depression which has required medication.
“She has had nightmares and flashbacks - it will take her years to get back to normality.
“She had to move home as the incident occurred not far from her home.”
Speaking about the second incident - committed 10 months later while Mills was on bail - the judge said: “It would have been evident to you that one of (the victims) was in her late 70s and the other was in her 80s.
“I take the view that you decided to approach them because they were more vulnerable than the younger lady.
“You sat in your car and invited them to participate in sexual activity while you were masturbating and I have no doubt you took some pleasure in doing so.
“They were hugely traumatised by what happened - it’s completely changed their lives.”
Laura Pitman, prosecuting, told Derby Crown Court how during the first incident in November, 2020, Mills followed his young victim into an alleyway at around 5.40am.
The “scared” girl had just set off walking to work from her Chesterfield home when she came across Mills - who was “stood in the street”.
After asking her the time Mills offered the female a “spliff” and then a cigarette, engaging her in conversation, walking alongside her as they approached the alley - which was still dark.
However Miss Pitman said: “As they entered his behaviour changed - he positioned himself in front of her and put his arms around her.
“As he stood in front of her he kissed her on the lips - she had done absolutely nothing to suggest that was what she wanted.”
Mills kissed the woman several times despite her repeated attempts to push him away, forcing her hand down to his privates - which were now exposed.
The court heard after sexual predator Mills tried to force his victim’s head down to his groin she was able to force him away.
Miss Pitmans said: “He then said ‘add me on Snapchat’, kissed her, then walked away.”
However the court heard while Mills was released under investigation he exposed himself to two elderly women on the same day - in September, 2021.
He targeted both pensioners - in their 70s and 80s - as they walked along the street in Chesterfield around 8am, following them in his car and uttering vile sexual comments.
One of the victims, aged 82, was walking along a road when she heard the defendant shouting from his car.
As she approached Mills’ black vehicle he asked her the time before asking her to “jump in the car” and asking her to have sex with him, saying “it will do you the world of good”.
As Mills exposed himself and the woman walked off he reversed along the road following her while touching himself before eventually driving away.
Miss Pitman said Mills later came across the second victim, aged 77, as she walked to a shop to buy a newspaper.
After repeatedly asking her the time, Mills followed the OAP in his car as he tried to make her way home.
The prosecutor said: “As she neared her home address she began to get scared - she didn’t want him to know her home address.
“He then opened the car door and she noticed his trousers around his ankles and his penis was in his hands.”
As vile pervert Mills tried to persuade the elderly lady to have sex with him a passing driver, seeing the woman in a “distressed state”, pulled up to check she was Ok. Mills then fled in his car.
The court heard the very same morning a young woman had called police to report a black car - later identified as belonging to Mills - had followed her as she jogged in Tapton.
Mills was linked with the September 2021 incidents after victims described a missing panel from his car interior and police viewed CCTV footage of him returning to his parents’ home afterwards.
He was snared for the November 2020 attempted rape when his DNA was found on his victim’s glasses.
Mills, of Boythorpe Road, Boythorpe, admitted sexual assault and two counts of exposure. He was found guilty of attempted rape during a trial.
He was ordered to serve at least two-thirds of an eight year jail term in custody and was given an extended licence period of four years to be served after his release.
The Boythorpe man was also made subject of an 18-year sexual harm prevention order.
Under its terms he is banned from approaching lone females he does not know or driving any vehicle without registering its details with the police.