Paul Mason, 42, became obsessed with Councillor Louise Jackson after a chance meeting at London St Pancras Station earlier this year.
Councillor Jackson took pity on Mason, of Chaucer Road, after hearing about his homeless situation and gave him her business card but soon found herself bombarded with love letters.
From August 4 to 17, Mason sent letters from prison to Cllr Jackson at both her home address and Bedford council offices, calling her “darling” and sending magazine cutouts of dresses he wanted her to wear.
Mason was convicted on September 27 after a trial at Luton Magistrates’ Court.
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In a victim impact statement, Councillor Jackson said: “When I came to court to give my evidence, the defence suggested to me that this offence was not that serious as I only received a few letter over a relatively short period of time.
“On the face of it, I suppose you could make that argument. But the impact of that whole episode has been greater than you could have imagined.
“I found the first batch of letters very disturbing and in fact frightening. It was clear the letters were from someone in prison.
“What was written was personal and targeted. Whilst I’m reasonably used to getting communication I’m better to ignore, this did not fall in that category.”
Mason had been jailed for six months in January 2015 after stalking former EastEnders’ actress Brooke Kinsella.
He bombarded the actress with social media messages, calling her ‘pumpkin’ and telling her she would be his wife, as well as turning up at public appearances and her workplace.
Councillor Jackson added that once she identified who Mason was, the situation felt “even more sinister”.
She said: “It became even more frightening because it [was] clear his previous convictions did not deter him and he was a serial stalker.
“Despite being a councillor I have always felt safe and secure in my own home. After receiving the letters, I felt exposed and vulnerable.
“I suffered many sleepless nights.”
Councillor Jackson added that she was sorry her good intentions to help someone had been “grossly” misinterpreted.
Mason was sentenced to 10 weeks’ imprisonment for harassing Councillor Jackson, along with a two-year restraining order and £100 compensation.
Mason was also sentenced to an additional six weeks in jail for masturbating on a train in January, following a conviction at trial, with prosecution costs of £300 and victim surcharge of £115.
No further penalty was taken for two convictions of possessing cannabis and trespassing on a railway line at Bedford Station.