Flamboyant transgender businesswoman Carmen lit a bomb under Wellington's 1977 mayoral race, much as she had shaken up its social life over the previous decade.

Carmen, born as a Taumarunui lad named Trevor Rupe, ran against incumbent mayor Michael Fowler in a campaign that featured bared breasts, a shock engagement, and strippers stopping rush-hour traffic. Her slogan was "Get in Behind".

"I am easily the best candidate," Carmen told 1000 university students at a debate that August.

"I am better looking than Sir Francis [Kitts], I am more charming than Michael Fowler and I could beat [Values candidate Tony] Brunt in a brawl any day."

The former stripper and prostitute arrived in Wellington in 1967, setting up her first coffee shop and brothel in Vivian St, to be followed by strip bars, curio shops and massage parlours across town. Carmen's International Coffee House opened when pubs closed at 6pm and attracted the full spectrum of Wellington nightlife.

"Businessmen brought their wives," drag queen Jacquie Grant told The Dominion Post, "and then they came back later."

In 1975 Carmen further shook the city's conservative core when she announced on television that some members of Parliament were homosexual and bisexual.

Her mayoral campaign was the brainchild of property baron Bob Jones, and funded by a group of Right-leaning businessmen tired of inaction under Robert Muldoon's first government.

"If Carmen was mayor, so our logic ran, nothing would ever happen and citizens would have a respite from ever-increasing rules and regulations," he wrote in The Dominion Post in 2007.

"Carmen cut a grotesque figure, as might be expected of a 136-kilogram King Country Maori bloke wearing a dress and flaunting massive breasts," Jones said.

"To put it kindly, Carmen was no Einstein. In fact, as we were to discover, she could barely read."

That did not matter to the public, who flocked to Carmen's appearances and her daily lunchtime drives around the city in an open-top Rolls-Royce, wearing a gown and opera gloves.

Jones wrote Carmen's speeches – in one-syllable words – containing policies such as allowing pubs to open until 2am, lowering the drinking age to 18 and decriminalising prostitution, abortion and homosexuality. She proposed to replace inner-city buses with trams, and Jones' influence was clear in her proposal to fund a new town hall though a privatised leasehold arrangement.

Carmen would attend debates in low-cut dresses, which often failed to contain her breasts, Jones recalled. By September she refused to attend further mayoral hustings, claiming to be bored by the "abysmally mediocre standard of debate".

"Carmen is pulling out of mayoral candidate forum meetings, quite aware that she might be called an intellectual snob. None of the other candidates chose that exact description," The Evening Post said.

She stepped up her campaign with a daily advertisement in The Dominion titled "Carmen's Thought For The Day", with quotes from the likes of Plato, Aristotle and Rousseau.

Another prominent Dominion ad listing dozens of Carmen's supporters sparked a protest when Jones added to the list without their consent a dozen "highly conservative QCs, businessmen and other city hierarchy", he said.

In retaliation, one of the named luminaries organised a dozen bare-breasted strippers to parade along Kent Terrace on election eve, October 7, bearing placards with indecent comments about Jones and Carmen's other backers.

In one last publicity stunt before the election, Carmen announced her engagement to top investor and businessman Ron Brierley. Gamely playing along, Sydney-based Brierley discussed the engagement ring and honeymoon when interviewed by Radio Windy, but his investment firm's share price fell, and one director threatened resignation.

Carmen was soundly beaten by Fowler on election day, but only narrowly missed out on one of 16 council seats. She fled Wellington in 1980 after being convicted for making a "blatant homosexual advance" to an undercover policeman at her coffee lounge.

She died in Sydney of kidney failure in 2011, aged 75.