The Sex Machine

Jon Gross is having more sex than you. Way, waaaaay more sex, and with way more people’s spouses. So how exactly did this middle-aged New England plumbing-supplies salesman find the secret to free love, make friends with porn stars and multimillionaires, and become America’s king of swingers?

From left, entertainment staff perform for guests after ­dinner; couples get up close and personal near a pool at the resort. Photo by Brian Finke

From left, entertainment staff perform for guests after ­dinner; couples get up close and personal near a pool at the resort. / Photographs by Brian Finke

Among Fluffernutters’ growing ranks during the mid-2000s was a tall, handsome man in his early fifties whom everyone knew, simply, as Harry. It was customary on Fluffernutters trips—as in the lifestyle in general—not to dwell on professions. Hardly anyone, including Gross, knew Harry’s true identity.

Outside of the Fluffernutters world, the well-tanned partier was Harry Lange, head of Fidelity Investments’ mammoth Magellan Fund, the closest thing the industry has to a household name. Masterminded by Boston philanthropist Peter Lynch, who grew it from $20 million in 1977 to $14 billion in 1990, Magellan became the world’s best-performing mutual fund, ultimately reaching $100 billion in assets under management at its peak. Lange, a slow-talking midwesterner, was a big-shot investor with a degree from Harvard Business School and a reputation throughout Boston society as a generous philanthropist and kick-ass ballroom dancer. Less publicized was his penchant for partying in the nude.

Lange says he missed out on spring-break debauchery and wild nights drinking in college, so he’s been making up for it in middle age. “Freud would say I must have missed some…stages,” Lange told me. He met his second wife while working for Fidelity in Tokyo in 1991; she doesn’t party as much as her husband, but she certainly doesn’t stand in his way.

Around 2006, a friend of Lange’s—a “woman friend,” he said—booked them a trip to Hedonism through Fluffernutters. Lange didn’t know it, he says, but that meant he was in for a particularly “naked, wild, crazy” week. Fluffernutters trips had gained a reputation among swingers as some of the wildest in the business—with Gross orchestrating round-the-clock parties beyond their raunchiest dreams.

Fluffernutters trips to Hedonism always kick off with an event Gross invented that’s called the CockNTail Party, held in Hedonism’s disco. “It’s so crowded people are brushing up against each other and you just get that sexual charge,” says Tom, the property manager from central Massachusetts. Most women wear lingerie: a lace bra and panties, pasties and a thong, or a baby-doll. Some of the men also arrive in underwear, either simple boxers or something more exotic, like briefs with a tuxedo design paired with a bow tie. Other men wear Bermuda shorts and expensive T-shirts. Gross usually wears a fedora.

At the beginning of the party, Gross hands out raffle tickets or cash to the men. (On some trips, the roles are reversed.) Then the women try to pocket as many tickets or dollar bills as they can. “It’s almost like the girls putting themselves out there like a working girl,” says Megan, Tom’s wife. “I was pretty shy the first couple of times.” But now she gets into the game, scanning the disco for men with tickets left. “Sometimes I’ll just go and start kissing them. Sometimes I’ll grab their penis. It depends on the person and what kind of vibe I get.… There’s some personal friends that I know very well and I’ll just turn around right in front of them and bend over.”

Onstage, there’s a blowjob contest (using a condom filled with liquid) and a sexual-position competition. There’s flipping and jumping and dry humping, and cheering and laughing from the crowd. In the midst of the party, Gross holds a live auction. The women bid—with their newly won tickets—on prizes such as vibrators, lingerie, and sex swings.

Most days, everyone hangs out at Hedonism’s “nude pool,” where nudity is required. The poolside bar is always open, blenders are constantly humming, and reggae is invariably playing. Guests flirt, fool around, and let it all hang out. Meanwhile Gross is often shouting into a microphone and organizing games, such as one called Car Wash. Women cover themselves in soapsuds and arrange themselves in two lines an arm’s length apart. Men run through this gauntlet and the women “clean” them by rubbing all over them. Then the sexes switch and the men “clean” the women. Other games are more innocent. One afternoon, Gross dumps hundreds of melon-size inflatable balls into the pool. A game of naked dodge ball breaks out that lasts for hours. It’s times like these that Susan takes a moment to herself, walks down to the beach several hundred feet from the pool, closes her eyes, and just listens. “It’s the sound of adults at recess,” she says.

At night, guests get dressed up for theme parties. On next month’s trip, there will be an I Love the 80s Glow Party, a Fetish Night—“Welcoming all fetish clothing, bondage gear, ball gags, furry cuffs, whips, [and] crops”—and, of course, the obligatory toga party. Dirty Diana, a woman who dances in a thong while two men pour milk all over her, will likely perform.

Another tool in Gross’s bag of party tricks is a Sybian, a sex toy shaped like a gymnastics pommel horse with a motor attached to a vibrator. A woman straddles the machine while Gross controls it remotely. “The girls don’t mind putting on a show for 10 people, 20 people in a room,” says Ron Jeremy, who has traveled to Hedonism with the Fluffernutters several times. “It’s certainly a thrill, which lends itself to a nice, erotic atmosphere because when it’s over and the girl climaxes, then couples start going, All right, hello there.” Gross gives every woman who rides the Sybian a souvenir T-shirt. The shirts come in orders of 144, and last year Gross ordered his ninth box.

People go on Gross’s trips with a variety of sexual agendas. Most of the Fluffernutters are swingers, but not all are. Some are playfully called “nude prudes”—they’re happy to party naked, but won’t touch anyone but their spouses. Some couples pick up single men or women for threesomes. Others are only into “soft swap,” meaning oral but no penetration—the light beer of swinging.

Karen, a former schoolteacher who now works for Gross, went on a Fluffernutters trip with her husband when they were in their mid-thirties and had no experience with public nudity or swinging. They went to party because they felt they’d hardly socialized with other adults since having kids. But their first trip—and the annual ones they took afterward—transformed their sex life. Before going, they had sex only a handful of times a year and never talked about what they wanted. But at Hedonism, surrounded by people having and talking about sex, that changed. “Our sexual life absolutely changed and improved 100 percent,” Karen says.

Teresa, a middle manager from the Manchester area, had planned to take it slow on her first trip. “I was thinking, Maybe after the third day I’ll go topless,” she says. But within hours of arriving, she found herself naked and chatting with a couple by the pool. Later, the husband knocked on her hotel room door and said, “My wife requests your presence in our room.” Panicked, Teresa shut the door and composed herself. “I’m thinking, Oh my God. What do I do? Do I go? Because I’ve never been with a woman, I’ve never been with a couple, I’ve never done anything like this.” After 20 minutes, she decided to do it. I’m fortysomething years old. It’s time. I need to branch out, she thought. When she got there, the couple was waiting for her with a strap-on dildo. After a while, some of the couple’s friends joined in, marking another first for Teresa: an orgy.

Other Fluffernutters are swinging pros, like Gross. “He’s just friendly, bubbly,” says Ron Jeremy, who is similar to Gross in height and girth. “He comments how pretty [a woman] looks, what an adorable outfit, and he just gets very personable.” More often than not, he winds up in bed with one or two of his guests. “We’re living proof,” Jeremy says, “that little guys can get laid.”