Sumner Redstone and Sydney Holland in 2014 Getty Images

That must have been a hell of a flight.

Media titan Sumner Redstone gave out many millions of dollars to multiple women — mistresses, a flight attendant and that attendant's sister — according to legal documents filed Monday by his 45-year-old ex-girlfriend. The CBS corporate jet flight attendant alone got $18 million — and her sister, whom Redstone allegedly bedded, received a cool $6 million from the randy billionaire, court filings claim. The explosive allegations by former Redstone paramour Sydney Holland were accompanied by a warning that she "may be forced" to seek testimony from the 93-year-old mogul's celebrity friends as well as from executives from Viacom and CBS, whose shares he controls, to substantiate her salacious claims. Redstone's legal team, in an emailed statement to CNBC, said, "Ms. Holland's cross-complaint is a work of fiction punctuated by not-so-subtle threats of extortion and an overwhelming stench of greed."

In her Los Angeles Superior Court filing, Holland said Redstone "gave tens of millions of dollars to various other women — who he had no intention of marrying and was not in love with — at the time he was engaged to marry" Holland. "Women who did nothing more than provide sexual favors," the filing said. Her allegations were made in a response to a lawsuit by Redstone accusing Holland and one of his other ex-girlfriends, Manuela Herzer, of conspiring to emotionally manipulate and abuse him so that he would give them gifts totaling $150 million over the years.



The filing said it "makes no sense" that Redstone's lawsuit only names Holland and Herzer as defendants when "Redstone knows that there were (and possibly still are) many other women who he gave tens of millions of dollars to (during this same time-period that he alleges Sydney and Herzer had 'total control' of his life)."

Holland also filed a cross-complaint against Redstone alleging breach of contract — both "oral" and "implied in fact." She says that in exchange for agreeing to make Redstone "the center of her universe" during their time together, he "promised to take care of her financially for the rest of her life." The filing asks that Redstone be ordered to pay Holland "a reasonable sum per month" to support her and her young daughters.

Sydney Holland Getty Images

Her filing said that for "five years, Sydney and Plaintiff Sumner Redstone ... enjoyed a loving, romantic relationship," which began in the fall of 2010 after the media baron "hired Patti Stanger, 'The Millionaire Matchmaker' to find him a girlfriend who was not only young and beautiful, but also intelligent, funny, and who shared Redstone's Jewish faith." Holland's filing said that "as a result of this lawsuit" against her and Herzer, "the lurid nature of these relationships and the significant amounts of money that Redstone paid to these [other] women are directly at issue." "Sydney may be forced to disclose their identities and call Redstone's celebrity friends and Viacom and CBS executives as witnesses," the filing said in her answer to Redstone's suit. The filing also said that it was known to Redstone's advisors, attorneys, doctors, friends and staff, as well as to Redstone's "close friend and CBS executive officer" CEO Leslie Moonves that Redstone had given Holland about 1.5 percent of his net worth over a five-year span. Holland's filing then offered a list of unidentified women and the staggering amounts they received from Redstone "just while Sydney was living with Redstone." "He gave one mistress — an aspiring reality show producer — approximately $21 million."

"He gave a flight attendant on the CBS corporate jet just approximately $18 million."

"He later slept with her sister, who he gave approximately $6 million."

"He gave another woman who he had formally met through Patti Stanger [the matchmaker] $10-11 million."

"He gave another mistress — who claimed to be a model — over $7 million."

"He gave a friend of his grandson's girlfriend a job at Showtime and approximately $6 million."

"He gave another mistress approximately $1.5 million."

"He gave an ex-fiancee and Paramount employee an undisclosed amount."

"He paid for a college student's tuition at the University of Southern California and gave her an undisclosed amount."