“She’s stunning,” I said. What else can you say when your seatmate on a flight from Tampa to Boston angles his cell phone to show you a selfie of a naked woman? Blond, in her mid-twenties, tan, and toned, she was in the shower aiming the camera down from above. I noticed a constellation of little tattoos near her breast. The woman, he said, was his girlfriend.
Turns out my seatmate, Jon Gross, was the sharing type. Even on the tarmac, before we’d taken off, he was letting me read his text messages to this woman. In one text, laced with exclamation points, the girlfriend announced she’d met a special someone. Gross, deploying many exclamation points of his own, congratulated her and wished her the best.
As I read the messages, my head was spinning. Why was his girlfriend telling him about a new man? Why wasn’t he bothered? And how had he landed this girl in the first place? Gross wasn’t a bad-looking guy. He had a well-proportioned face, hazel eyes, and a charming, impish smile. But he was, by his own admission, 57, mostly bald, 5-foot-4, and 210 pounds. Plus, he was dressed like a slob in an oversize cotton T-shirt and athletic shorts.
As we talked more, my confusion only deepened. He mentioned other girls and showed me pictures of them: a thirtysomething blond woman in lingerie, who made her living as a marketing executive; a brunette DJ who could easily have passed for a model. Then he mentioned his wife, a petite woman closer to his age. “My wife’s a beautiful woman,” he said, gazing at a picture of her before flipping to another photo, which left me even more baffled: his wife and the blond marketing executive on a beach, arms around each other, smiling.
During the next two hours, Gross sketched out his life story. A Sharon native, he’d been a computer and radio geek as a kid, a plumbing-equipment salesman through early middle age, and, later, one of New England’s Internet pioneers. These days, though, he makes his living as the head of a company called Jon’s Fluffernutters, which throws round-the-clock parties for hundreds of naked, free-loving adult members, most of whom participate in secret.
When I met Gross last spring, he was recovering from one of these blowouts: a three-night-long fete he’d hosted at a “clothing optional” resort called Caliente. The event had been a cross-promotion, he told me, with his other business—the somewhat infamous Jamaican nudist resort Hedonism II, which he co-owns. His business partner, and the money behind the operation, is Harry Lange, former head of Boston’s $17 billion Fidelity Magellan Fund. A longtime Fluffernutters member, Lange had partied with Gross for years—the two had sipped margaritas naked in Jamaica and cavorted with Playboy Bunnies at Hugh Hefner’s mansion in L.A.—before buying the resort with him in 2013. More surprising than anything, though, was that Gross ran his hospitality empire not from Miami or Las Vegas, but from an office building near his home in Manchester, New Hampshire.
At first, it was tough to believe anything Gross told me, but the quick stream of pictures, videos, and messages he showed as evidence were hard to dismiss. In addition to his girlfriends’ selfies, Gross showed me several glamour shots, including one in which he was standing at a red-carpet event with his arm around a grinning Ariana Grande. Gross also showed me his text messages with world-famous porn star Ron Jeremy. In a recent message, Jeremy was texting Gross about where to find an after-party.
Yet Gross didn’t strike me as a namedropper. In fact, he seemed more interested in talking about his ordinary customers. He told me his target demographic is married, middle-class couples who sneak away from their families and friends on vacations to get naked and sleep with one another. Gross and his wife, he explained, weren’t just instigators but active participants. They’re in an open marriage themselves: They are both free to sleep with whomever they like, no strings attached, and like to spend their vacations at Hedonism II partying naked with clients.
After my chance encounter with Gross, I got to know many of these people—teachers, accountants, police officers, and lawyers from throughout New England and around the world. There are thousands of them, all happy to pay for the privilege of partying with Jon Gross. The ones I met spoke of him in fawning terms, as if he were the beloved pastor of a megachurch. Except instead of salvation, Gross’s flock seeks liberation through nudity, hard partying, and free love, one blowout weekend at a time. “What’s better than making a living throwing a party, and being the man, and helping people’s lives, and people actually loving you for it?” Gross says. “That’s pretty unbelievable, you know.”
The first time Gross got naked in public was on a hill in Jamaica. It was 1985 and he was a young man vacationing with his wife, Susan (hers and other swingers’ names in this story have been changed). High school sweethearts who are still together, Jon and Susan started out as a conventional couple. He was a salesman at American Granby, a vendor of plumbing equipment headquartered near Syracuse, New York. She was a teacher. They lived in Manchester and had a young child. Back then they were still monogamous and got naked only in the privacy of their home. But while on vacation Gross had heard tell of a Jamaican resort called Hedonism—which had a nudist beach—and he had the cheeky idea to check it out. Why not sneak in?
It was shockingly simple. Jon and Susan walked through the resort’s lobby as if they were guests. Behind the building, they climbed a small hill by the beach and saw the sprawling resort for the first time. “Everybody was naked,” Gross says.
“What do you think, honey?” Jon asked Susan. But he didn’t wait for an answer. By the time she turned around to speak, Jon had already ditched his clothes. After Susan undressed, they ran down to the beach together and plunged into the water to take cover. They were still trying to figure out their next move when some of the guests swam out to introduce themselves to the newcomers.
For Jon and Susan, the nudity came fast and easy; embracing polyamory took longer. “The first few years we went to Hedo, we went because it was sexy,” Gross says. “But I didn’t even know what ‘the lifestyle’ was.” “The lifestyle”: no adjectives necessary. It’s swingers’ favored euphemism for what they do, whether that’s trading up spouses for sex or bringing individuals from outside a marriage into the bedroom. “I was so far removed from any thoughts of it,” Jon says. But at Hedonism, a mecca for the swinging world, they received a swift education.
On a trip in the early 1990s, Gross and Susan met a husband and wife from Connecticut in a hot tub, who invited them back to their room to smoke pot. “I turned to Susan,” Jon says, “and I said, ‘I think we’re being hit on.’” Susan thought he was reading too much into it, but Jon said, “I think you’re being naive.” To be safe, they talked about what they’d be willing to do. They concluded that they were open to anything. When they arrived at the room, Jon says, the wife had already changed into a negligee. There was no marijuana.
Forty minutes later, Jon and Susan walked out of the room and into the sunlight. Jon asked Susan how she felt about having sex with the other couple. She was fine. Did anything feel different? No, she said. Jon told her he felt fine, too. “That’s pretty amazing,” Jon says. “I thought it would be more emotionally trying. But, you know, the environment was right for it. We both went into it with the right attitude. And we’ve been in love with each other since junior high school. It just doesn’t change that.”
At first, Jon and Susan kept their swinging confined to the hot tubs and hotel rooms at Hedonism on annual trips. After a few years, though, they began exploring “the lifestyle” in New England. This was before the Internet, and finding other couples was an underground, often seedy process of going to sex shops and buying magazines containing classified ads posted by swingers. To make contact, Jon and Susan sent a nominal amount of money and a self-addressed envelope to the magazine’s publisher, who would put them in touch. If the other couple was interested, they’d set up a double date. Soon, Jon and Susan were getting invited to weekend bacchanals in the tony suburbs, where couples paired off and disappeared into empty rooms. They also went to swingers’ nights at alternative bars, such as the now-defunct ManRay, in Cambridge, and members-only clubs, such as the Black Key Club, in Providence, known today as Choice Social Club. Fondling in the open was accepted and, frankly, expected. If two couples hit it off, they would go “play”—another euphemism—in a private room.
By the early 2000s, Jon and Susan began throwing their own swingers’ parties, renting a gay bar in Manchester one Saturday a month and welcoming couples from across New England. They quickly became well known in the swinging community for their openness and generosity and fell into the role of mentoring younger husbands and wives.
One of these couples was Tom, a property manager, and Megan, a customer service agent, from west of Boston. At 5-foot-9, Tom is muscular with short, spiked hair. Megan—pale with dark hair—looks like any suburban mom. According to one Yelp-like review online, they’re known among swingers for “that giant kickstand of his” and her “great ass that we can’t stay away from.”
Their foray into swinging progressed from pillow talk about bringing a woman to bed to joining the Black Key Club. When they met Jon and Susan, who were about 15 years older, Tom found Susan attractive, but Megan thought Jon looked like Danny DeVito. Still, Tom and Megan had questions: how to deal with jealousies? How to meet new couples? How to set boundaries? Jon and Susan were happy to lend their expertise, even bringing Tom and Megan to secretive, invite-only swingers’ parties.
After months of platonic friendship, Megan became less concerned with physical appearance, and her feelings about Jon changed. “The longer you’re in the lifestyle, the more you look at people for who they are and not what they look like,” Tom says. So the four of them went off together and had mind-blowing sex. “Let’s just say [Jon is] very good with his fingers, and not a lot of guys are,” Megan says. “It’s almost like he gets inside your head and your thought process [and] it becomes more sexual.”
To the casual observer, it might seem like swinging has disappeared. It’s certainly no longer part of the zeitgeist, as it was in the 1970s and 1980s. In reality, though, swinging is bigger than ever—just a lot less visible. For that—and for pretty much everything Gross has—he gives thanks to the Internet.
Initially, the Internet made it easier for couples to meet—but the same technology also made rumors spread faster and wider than ever. Fearful that their private lives will be made public, many couples refuse to swing in their own towns, where they might run into someone they know. Ultimately, the Web pushed swingers further underground—and, well, south. Trips to Hedonism and similar resorts, such as Desire in Mexico, offer outlets where swingers can stop sneaking around and gambol with like-minded people. To connect regional swingers with the happy, tropical hunting grounds south of the border, a burgeoning cottage industry of “lifestyle” travel groups arose. Gross helped pioneer this concept by creating his swingers’ and nudists’ travel club, Jon’s Fluffernutters. His competitors have included groups called Bubbly Bares; Wet, Wild and Wicked; Young Swingers; and an outfit called Kamasutra Week. Gross, opting for a subtler moniker, named his group after his and Susan’s favorite New England treat.
In the beginning, Gross was just trying to raise the bar on his annual trips to Hedonism. As with the swingers’ parties back home, Gross found the atmosphere there playful and sexy, but he wished the resort itself was better. The food was only passable and the liquor was bottom shelf. He also thought it could be more fun. “I wanted to have a party,” he says. “I wanted to add some amenities.”
Lucky for Gross, money wasn’t a problem. In the early 1990s, he’d installed a server in his basement and had the phone company run dozens of new lines to his house. These pieces created a “bulletin board” that allowed users to dial into the server from their home computers and exchange messages and files—the earliest version of online social networking.
It didn’t take long for Gross’s childhood friend Ed Lennon to suggest that the board could become more than just a hobby. Soon they went into business together, forming Grolen Communications. Through the 1990s, they built Grolen into the first Internet service provider in Manchester, a manufacturer of computer workstations, and an outsourced IT department for regional businesses. As one of the hottest tech companies in New Hampshire, Grolen drew visits from presidential primary candidates every four years. Little did they know it, but candidates such as Al Gore and John Edwards were grip-and-grinning with one of New England’s biggest horndogs.
Grolen left Gross with plenty of disposable income to spend on making his excursions to Hedonism more fun and luxurious. On a trip during the late 1990s, he passed out tiny plastic lobsters to everyone on the beach and hired a local fisherman to hand out real lobsters in exchange for the toys. Then Gross threw an impromptu cookout and paid Hedonism’s grill man to cook the lobsters. A few days later, Gross hired a catamaran to take 40 guests on a sunset cruise. Both events became annual traditions, as did Gross’s habit of organizing naked games by the pool.
In a few short years, Gross became such an important part of many guests’ Hedonism experience that these relative strangers began planning their vacations around him. One winter in the late ’90s, Hedonism’s hotel manager called Gross to find out his travel plans. A dozen people were waiting to book until they knew when Gross would be there, and the manager needed to know what to say. Soon, so many couples wanted to travel with Gross that Hedonism offered to pay him a commission, sparking the idea for Fluffernutters. Founded in 2003, the group grew quickly, expanding from 30 couples to more than 40 by the following year. Most members were enmeshed in the lifestyle.
Gross built a website where Fluffernutters clients created profiles, sent messages, and shared photos. His computer skills proved to be a boon. Within a few years, thousands of registered users were active on the Fluffernutters website, and Gross couldn’t keep up with demand. He added additional trips to Hedonism and branched out, throwing lifestyle parties in Las Vegas, in Denver, and at the Playboy Mansion in Los Angeles. In 2004, with Grolen’s sales in decline, he left the company to dedicate himself to Fluffernutters full time. “It’s funny,” he says. “It’s mostly tech geeks who have thrived in [the lifestyle travel] business.”
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.”
Despite its name, Hedonism is about more than simply getting off, the resort’s fans say. By shedding their clothes and their inhibitions, they escape their everyday lives and insecurities. Status markers disappear almost entirely; a mantra among Fluffernutters has become “Nudity is the great equalizer.” Women, especially, say that being surrounded by naked people of all shapes and sizes makes body-image concerns go on hiatus. Paradoxically, getting naked makes everyone less self-conscious.
Gross insists that going to Hedonism creates strong friendships. Fluffernutters often open their homes to other members after meeting only once or twice. After Hurricane Sandy, a Fluffernutters couple from Texas loaded a truck with building materials and a generator and drove to the New York area to help members who had been hit by the storm. In 2010, the Fluffernutters and Hedonism community raised about $70,000 to pay for travel and lifesaving medical care for Hedonism’s night manager, who had suffered a potentially lethal brain aneurysm.
As Fluffernutters members tried to explain what Hedonism means to them, they invariably reached a point where they gave up and said something like, You just have to go and experience it for yourself. The resort’s staffers greet every guest with the words “Welcome home.” “When I got there my first time, I thought, What kind of Kool-Aid are these people drinking?” Karen says. But now she understands the greeting—arriving at Hedonism, she says, feels like a homecoming. It’s the kind of sentiment you’d expect to hear from a true believer, which is what the regulars are. Gross acknowledges this with an impish grin, saying, “It’s kind of cultish.”
For Gross, that devotion ultimately paid off. In 2012, Hedonism’s owners put the dilapidated resort on the auction block. “I started to panic,” Gross says. “I thought to myself, If Hedonism goes out of business and becomes a family resort, what am I gonna do?” Then he remembered Harry Lange.
At the time, Lange had plenty of free time on his hands. In 2011, Fidelity had replaced him as head of the Magellan Fund, which failed to keep pace with the S & P 500 and its peers during Lange’s tenure. (Under Lange’s management, Magellan had fallen from $52 billion to a mere $17 billion, as investors withdrew money.) He knew that owning Hedonism would be toxic in the world of high finance, but that was no longer a concern. “When I lost the fund,” he told me, “it’s kind of the end of a career.”
When Gross approached Lange, asking if he wanted to save their beloved nudist Valhalla, Lange was interested. They agreed that Lange would be the money and Gross the talent. After closing the deal, Gross became CEO of Hedonism and took a minority ownership stake as compensation. “It was my favorite place in the world,” Lange says, “and I think 10,000 other people would say it’s their number one place.”
Still, the deal was not without consequences. When Lange’s term on UNICEF’s board of directors was up, he wasn’t asked back. Lange believes he lost his seat because UNICEF’s directors were put off by his new property. He also believes Hedonism cost him some of his more conservative friends. But Lange doesn’t regret the outcome. He spends as many as 200 days a year at Hedonism—staying in a guest room, just like everyone else—and hanging out at the nude pool or partying in the disco. “When I see him at the pool now,” Gross says, “with his arms around two girls, I ask him, ‘How’s the investment? How are those dividends treating you, Harry?’”
Since becoming co-owner and CEO of Hedonism, Gross has upgraded his digs back in New England. After working from home for years, he now conducts his business from a corner office atop one of Manchester’s two skyscrapers. From his desk, he sees a panorama of rolling hills and can nearly make out the storefront of the only remaining Grolen location. He manages Fluffernutters full time and organizes six annual trips to Hedonism, some attended by more than 500 guests. Now that he’s an owner, he rarely hosts events at other resorts anymore.
Gross opts for a calmer life these days, having spent more than a quarter-century swinging and swapping and throwing the wildest, raunchiest parties in the Western Hemisphere. When I met him on the plane in April, he complained of fatigue, not just from the previous four days of partying, but also from the three decades he’s spent carousing and having sex with other men’s wives. All he wanted to do was get home to Susan and stay put for a while. In October, he told me, “I’m not in pursuit of anything like that right now,” referring to sleeping with other women. As if to demonstrate, he pulled up his and Susan’s profile on one of the lifestyle social networks. He had 21 unread messages from couples in Newburyport, Andover, and Fitchburg. He didn’t intend to respond to any of them. “I don’t know if it’s just a phase and I’ll come back to it,” he told me the next day, “but it feels more permanent than that.”
After all these years in the lifestyle, Gross feels he’s reached the end of something, but it’s also the beginning of a new phase. The future, he says, will be more about building his businesses than racking up sexual exploits. He and Lange are in the midst of a $10 million renovation at Hedonism. In a few years, if all goes according to plan, virtually every part of the resort—from the cramped disco to the outmoded guest rooms—will be upgraded or replaced.
When the renovation is done, the plan is to expand. Gross and Lange envision Hedonism resorts all over the world, from Thailand to the Canary Islands, with Hedonism-branded lifestyle clubs or hotels in major American cities such as Las Vegas. Although the resort is profitable, Lange says, its cash flow alone will never generate great returns. The real upside is in leveraging the name.
As Hedonism expands, Gross’s role will naturally grow. He’s the figurehead, the pied piper, the guy who knows how to whip legions of homemakers and middle managers into a sex-fueled frenzy. If he and Lange want to export the resort’s culture—and not just the name—then Gross is definitely the way to go.