Sports Illustrated swimsuit model Martha Stewart’s sinful life

For decades, Martha Stewart, the “diva of domesticity,” showed us how to entertain fabulously.
And now America’s hottest octogenarian’s latest foray in entertaining is taking it all, or mostly all, off as a cover girl for Sports Illustrated’s new sexy annual swimsuit issue.
Like Norma Desmond, played by Gloria Swanson in the film Sunset Boulevard, Martha, 81, loves being on camera, looks spectacular, and probably believes as Desmond did, “The stars are ageless, aren’t they.”
She calls being a sex symbol “fantastic.”
But Martha’s decision to pose where once young bikini-clad beauties like Kate Upton, Tyra Banks and Christie Brinkley graced SI’s cover should not come as a surprise to Martha insiders.
Martha Stewart and her husband Andy were “adventurous,” according to Jerry Oppenheimer’s best-seller, “Martha Stewart: Just Desserts: The Unauthorized Biography.” Getty Images
Stewart is now Sports Illustrated’s oldest ever swimsuit edition cover girl, posing at 81 for the annual magazine. Ruven Afanador/Sports Illustrated
Stewart was a “thirst trap” before the term was invented, and her Turkey Hill estate was the center of an “adventurous” scene. Getty Images
Long before the public ever heard of her, Martha was considered a very hot and desirable lady — holding sex-themed parties in her Westport estate, Turkey Hill, that would not have been appropriate for inclusion in her first big book that made her a star, “Entertaining.”
Those parties, involving a very small select group of couples and singles shocked some of Martha’s close friends who were invited to her sexy get-togethers for the first time.
They were also usually held when her attorney husband and later New York publisher, Andy Stewart, was out of town.
“My husband was sort of horrified at the behavior he saw going on,” recalled Martha’s close friend, Norma
Collier, a former model and Martha’s catering business partner for a time.
“Martha, for instance, was on [another man’s] lap. She was acting pretty playful. My reaction was that Martha walked on the wild side. This is part of who she is.”
Collier died at 82 in 2021.
In the swinging Seventies, according to friends, the Stewarts had a black bottom pool installed.
Behind the rural idyll, Martha and Andy Stewart’s estate was also a venue for nude pool parties. Getty Images
At the estate the couple installed a black-bottomed pool, and it became a party venue. “Martha walked on the wild side,” a friend dished later. Getty Images
“They had nude pool parties,” Collier said. “But Martha told me that she was not inviting my husband and me because she thought we were uptight Republicans, wet blankets.”
At at least one of the parties, according to Collier, “certain guests on arrival were asked to place their house keys into a fancy bowl and at the end of the evening retrieve a set of mystery keys and go home with the owner.
“I thought it was a joke and maybe it was a joke. But back then those kind of things were known as key parties for the sexually adventurous, and Martha was both creative and adventurous.”
She added: “Martha was not embarrassed by any of this, said it was fun, and liked it. She was an experimental person and would do anything to get kicks or shock people, and Andy would go along with anything Martha asked him to. They were two young people not clinging only to each other.”
“Martha was both creative and adventurous,” her friend Norma Collier dished before her death. Getty Images
The man on whose lap Martha was flirting was a handsome friend and colleague of Andy’s who had recently divorced.
“There was a lot of chemistry going both ways between Martha and me,” he acknowledged years later. But he claimed they had not slept together.
“Martha was just great-looking,” he asserted. “She had incredible sort of porcelain-like skin and she looked so delicate, yet there was nothing delicate about her in terms of her personality. I had a history of being involved with challenging women, so maybe that was part of our thing.
Stewart had “porcelain skin, and she looked so delicate, yet there was nothing delicate about her in terms of her personality,” a man who flirted with her acknowledged.
Before her marriage to Andy, Martha Stewart was a model,
“I don’t remember having any feeling that Martha was somebody I wouldn’t want to get involved with. I don’t remember what my fantasies were in those days, or whether I had any about her, or whether they would have stimulated a wet dream.”
According to the source, Andy and Martha often made “allusions” about their sex life, and noted that Andy was a strong guy who “wouldn’t be cuckolded.”
He recalled that Andy once said that if he found out that some other guy had a “better sex life than he did, he would really be bothered, that it would be troublesome,” if just the physical act of having sex was better for somebody else than it was for him.
Martha’s thirst-trap history goes back to the 60s — and in the 70s she was a flirtatious part of the party-scene at her and her husband’s estate.
AN evening at Martha’s was a hot ticket for friends — but Norma Collier says she and her “wet blanket Republican” husband weren’t invited to the most adventurous parties. Getty Images
“He said this in front of Martha, and I took it to mean that he was talking about his relationship in bed with her.”
Andy, long since divorced from Martha, later told a confidant that he believed Martha and the man actually did have an affair.
In the mid-Sixties, before their only child, Lexi, was born, Andy and Martha decided to take a grand tour of Europe in a Volkswagen bug.
In “Entertaining,” she wrote that the trip was the beginning of her “serious culinary education.”
But omitted from the book, but revealed by a close source, an upsetting incident occurred while they were staying in a hotel in Florence.
The couple met a handsome Englishman at dinner, and the threesome broke bread and consumed wine.
By 11 p.m., all were a bit tipsy and Andy wanted to call it a night.
But Martha didn’t and when Andy went off to bed alone, Martha and the other man left together.
The romantic city of Florence was a honeymoon destination for the Stewarts. When Martha spent time away form her husband with a hunky Englishman, she said they had merely been at midnight mass at a cathedral. REDA&CO/Universal Images Group via Getty Images
According to the source, Martha didn’t return until long after midnight, claiming she and the man had attended midnight mass at the local cathedral.
During fights, Martha would call Andy “boring, oafish, and sloppy” — and during one go-around in a fit of anger, she told him she had slept with another man while on a business trip to Los Angeles.
But she dismissed the tryst as “a one-time thing…merely an experiment.”
Martha was a flirt and men were constantly chasing her.
As a married stockbroker, Wall Street guys and men-about-town salivated over her.
She was hired, in part, to sell stock, as one of her bosses said, “because of her great legs.”
One of her stockbroker colleagues was Brian Dennehy, the future actor, who became close chums with
Martha — and had difficulty keeping his eyes off of her.
Among Stewart’s admirers were Brian Dennehy, before he was a successful actor. He called her “extremely sexy” and said she intimidated his then-wife.
“In those days,” he recalled, “she was skinny, and gorgeous, and extremely sexy. I would fantasize about
being involved with her.”
Dennehy, who was married at the time, said his wife was “intimidated” by Martha.
Years later, after Martha and Andy were divorced, he said he tried to pursue her romantically, “but I never thought I’d be sharp enough, or smart enough, or successful enough to have a personal relationship with her.”
When a dozen long-stemmed red roses arrived with a note signed “Andy,” her colleagues in the brokerage firm of Monness, Williams & Sidel believed the flowers had been lovingly sent by her husband, Andy Stewart.
Man-about-town and politician Andrew Stein, seen in the 90s with Shirley MacLaine and Brooke Shields, was infatuated with Stewart, and she was flattered at the millionaire’s pursuit. Getty Images
In fact, the flowers had been sent by a different Andy: Andrew J. Stein, who had first spotted Martha at a pay phone and began chatting with her.
Stein — once described as “Politics’ Bad Boy” by The New York Times — would serve as New York City Council president, Manhattan borough president, and run unsuccessfully for mayor.
He was divorced and smitten by Martha.
Besides the flowers, he took her out for drinks and began regularly calling the married mother of one at home, and Martha was flattered being pursued by the famous millionaire New Yorker.
Stewart’s SI cover fame opened a new dimension in her long career. Ruven Afanador?SPORTS ILLUSTRATED
Stewart has used her Instagram to post a series of thirst traps including this one at her Hamptons pool before she sold the property. Instagram/marthastewart48
But when Stein called once too often, Martha’s husband, Andy, answered and told him, “Keep the f–k
away from my wife” — so Stein did.
Years later, Stein acknowledges, “In those days I was single and attracted to attractive girls and Martha was attractive. She had a great look, and her response to me was friendly enough.”
He revealed that he dated her three or four times, taking her to Raffles, a private club at the Sherry-Netherland Hotel.
“We had three or four drinks. It was just sort of playful flirting. We didn’t have sex or anything.”
As Martha’s close friend Normal Collier saw it, “Martha could be flirty, and she liked men, and she liked
affirmation.”
Jerry Oppenheimer is the author of New York Times bestseller Martha Stewart: Just Desserts: The Unauthorized Biography.