MP Chris Huhne's partner Carina Trimingham has lost her privacy and harassment claim against Associated Newspapers.
Her affair with the former secretary of state for energy and climate change became public in June 2010, with Mr Huhne leaving his wife of 26 years.
The 44-year-old PR adviser, the daughter of Argus writer Adam Trimingham, sued for compensation and an injunction over 65 "highly unpleasant and hurtful" articles which have appeared since then.
Last month, her lawyers told Mr Justice Tugendhat, at London's High Court, that they constituted a "cataclysmic interference" with her private life.
Associated contested the case on the basis that there was an important public interest.
Ms Trimingham's counsel, Matthew Ryder QC, said the Daily Mail had a right to freedom of expression but not to abuse her repeatedly under the guise of exercising that freedom.
The articles referred to the "life and very different loves of the PR girl in Doc Martens" and described her as a "comedy lesbian from central casting".
Ms Trimingham was in court today but showed no emotion as her claim was dismissed by the judge.
He said: "Ms Trimingham was not the purely private figure she claims to be. Her reasonable expectation of privacy has become limited."
Outside court, Ms Trimingham said: "I am extremely disappointed by this judgment. There is a ray of light, however.
"Thankfully, the court has accepted today that repeated mocking of a person by a national newspaper by reference to their sexual orientation would almost inevitably be so oppressive as to amount to harassment.
"However, the court did not appreciate that when newspapers make repeated irrelevant references to sexuality - particularly in the context of pejorative and stereotypical references to appearance - it amounts to the same type of mocking which the court has confirmed is unacceptable.
"This is confused, and I think wrong. I am very concerned that this judgment may become a blueprint for bullies and bigots. I intend to appeal."
Ms Trimingham, who is insured, was ordered to pay £250,000 on account of Associated's estimated £410,000 costs within 14 days.
A spokesman for Associated Newspapers said: "This was an important example of the press exercising its right to free speech in relation to matters of significant public interest.
"We are pleased that the court agreed with us and has today dismissed all of Miss Trimingham's complaints.
"The references to Miss Trimingham's sexuality in our coverage were never pejorative, private or in any way homophobic.
"Miss Trimingham chose to level some very serious charges against our journalists in this case. This judgment vindicates both our journalists and their journalism."
Mr Ryder told the court the articles made constant and gratuitous reference to Ms Trimingham's sexuality and previous relationship with another woman, with whom she entered into a civil partnership in 2007, eliciting offensive and sometimes homophobic comments from readers.
"Miss Trimingham is not ashamed or embarrassed by her sexuality but it was private.
"She wished to have control about who she told and about how widely it was known. That has gone."
Antony White QC, for Associated, said Ms Trimingham was "not a shrinking violet but a seasoned political journalist".
"She is open about her sexuality and, perhaps most telling, she has sold stories about other people's sex lives to the press.
"She gives as good as she gets. She dishes it out."
The focus of the articles was Mr Huhne, and Ms Trimingham's relevance was her role in the Eastleigh MP's marital breakdown, which set off the "after-shocks" they dealt with.
He added: "She is properly in the news because she is relevant to a story about Mr Huhne."
Mr Huhne was not a party to the action and did not give evidence or attend the hearing.
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