Jonathan Kovacik, wealthy businessman has allegedly shot a sex worker after offering her £50,000 to marry him.
He also gave Rosalynde Pitcher £6,000 in cash towards her breast enlargement operation because he was in love with her, a court reported.
Ms Pitcher broke off her 'open' relationship with the 58-year-old after the operation, which saw her breasts increase from an A-cup to a D-cup last year.
Kovacik then reportedly shot her with a pellet in the temple and struck her five times with the weapon as she knelt screaming on the floor, Portsmouth Crown Court heard.
The former parish councillor denies four charges including wounding with intent, possession of a firearm with intent to endanger life and having an article with a blade or point.
He also denies possessing a firearm with intent to cause fear or violence towards officer PC Matthew Rumsey.
During the hearing Ms Pitcher, a webcam girl, described their relationship as 'friends with benefits'.
She sent text messages to Kovacik that said he should 'get her a boob job' because they were 'too small and she didn't like them'.
She also claimed he offered her £50,000 to have a baby, but said if she fell pregnant it would have stopped her having a breast enlargement operation.
Kovacik then visited her home in Shanklin, on the Isle of Wight, on December 21 last year after he started to fear she was 'stringing him along' for his money, prosecutors alleged.
Rob Griffiths, prosecuting, said: 'He had been very good to her - he bought her a car, various presents and had given her money towards having a breast enlargement operation.
'He thought perhaps she had been stringing him along to get his money, and as he said at the end of his interview: "There's no fool like an old fool."'
Ms Pitcher, a mother-of-one, told the court how she let him into her flat after knocking on the door and asking to come in, claiming he only had 'a few months to live'.
She said: 'I walked to the lounge and he was behind me when I turned around and he had a gun pointing at me.
'He was really quiet and wasn't saying much. He was holding the gun directly at me in his right hand and started walking towards me holding the gun at my head.
'I dropped to my knees and he put the gun directly to my head.
'I was screaming, I was just screaming: "Help". He was really quiet and just looked really angry and I had never seen that face on him before.'
During the confrontation Ms Pitcher said she did not realise she had been shot with a pellet but remembered hearing a 'clicking' and 'popping' noise.
She was able to escape via a flight of stairs by her back door as Kovacik ran after her trying to grab her dressing gown, the court heard.
He was apprehended by police in Cowes.
The pellet from Kovacik's pistol was only discovered at hospital a week later after x-rays revealed it was lodged under the skin.
Kovacik has claimed he was mentally unwell at the time of the attack and suffering from temporary insanity.
He said he took a diving knife and an air gun to her home over fears Ms Pitcher's father Lee would be violent towards him. The trial ongoing.