This Man Is a Sex Machine

Hedonism II co-owner Jon Gross dons a plush black robe, common workplace attire at his office in Manchester, New Hampshire. / Portrait by Dana Smith

“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.”

A couple enjoys some time on a clothing-optional catamaran sunset “booze cruise” in Jamaica. / Photograph by Brian Finke

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.”