Sex in Boston 2016: This Is How We Do It

Now more than ever, Bostonians’ sexual identities, mores, and mating habits have become fluid. Confessions from the front lines of our secret sexual revolution. —Edited by Rachel Slade and Julie Dugdale


Kit, who has a PhD in robotics from Carnegie Mellon, runs a meet-up called Teasecraft to help people make their own toys using devices like this vacuum chamber. / Photograph by Toan Trinh


We Use Our PhDs to Make Sex Toys

This former robotics worker holds regular meet-ups for people who want to make their own paraphernalia—the kinkier the better. By S. I. Rosenbaum

The thing about putting a penis in a vacuum chamber, Kit discovered, is that the vacuum has a tendency to suck the balls in, too. Also, it’s difficult to keep the penis centered in the chamber while you pour in alginate, a glutinous goo that hardens into a mold. Making sex toys can be complicated—even if you have a PhD in robotics from Carnegie Mellon.

Kit has one of those, and worked at Bedford-based robotics firm iRobot before quitting in 2011 to become a blogger and educator in sex positivity, a movement that celebrates the diversity of sexual desires, safer sex practices, and consent. Around the same time, Kit—who identifies as neither male nor female, and prefers the pronoun “they”—became a regular at Artisan’s Asylum, the DIY “makerspace” in Somerville. Inevitably, Kit says, “There was this light bulb moment: I could make sex toys!”

Designing original sex toys requires equal parts geek and kink, in Kit’s view. “It’s about problem solving,” Kit says. “It’s an engineering challenge.” The first dildo Kit built was clear, the silicone embedded with the likeness of a tiny TARDIS (the time machine from Doctor Who). Next was a double-headed toy fitted with sensors: Squeeze one end, the other end lights up. The project wasn’t quite a success—it was a little hard to maneuver—but it has its uses. During presentations on DIY sex toys, Kit likes to strap on a version of the light-up dildo underneath a lab coat; it makes for a nice reveal at a strategic moment.

Then there was the friend who approached Kit about replicating his penis as a gift for an ex-girlfriend. That’s where the vacuum chamber came in. Turns out, when you cover an erection in alginate, it tends to lose its gusto pretty fast. The vacuum chamber has the effect of, well, plumping things back up. “It’s the best your penis will ever possibly look,” Kit says. The ex-girlfriend was appreciative.

Boston’s booming geek population—about 20 percent of the Massachusetts workforce is employed, directly or indirectly, by the tech industry—has provided Kit with a steady supply of willing collaborators. It’s easy to rally support and resources from a bunch of people who know what it’s like to pursue idiosyncratic interests. In fact, Kit runs a regular meet-up called Teasecraft for people interested in crafting their own toys (November’s was called “Better Sex Through Trigonometry”), and last May also launched the Effing Foundation, which aims to help people fund their sex-positive artistic, business, and educational projects.

Kit, though, remains an engineer at heart—and believes that there’s no sex problem that technology can’t solve. “I want reconfigurable genitals,” Kit says. “I want to have a penis, and flip a switch and go back to my vagina. I want to know what it’s really like to have all different kinds of genitals.” That’s a long way off, of course: “It’s going to take dynamically reconfiguring nanorobots to make that happen.”


We Charge a Fee (But Don’t Call It Prostitution)

Sara wasn’t a sex worker. She just had sex…and got paid. By Brooke Jackson-Glidden

Sara agreed to meet the guy once, but she had no idea what to expect; as a senior at Tufts University, she’d never been much of a dater, and this was her first match on Seeking Arrangement. The legal website, founded by an MIT alum, pairs young women with wealthy men (their salaries and net worths appear in their profiles) under the intentionally vague premise that the pair will arrive at an agreeable “arrangement” for connecting.

Her date was older—by 43 years, to be exact—but she didn’t mind. They met at the Charles Hotel in Cambridge, and he seemed nice. They had a few drinks and dinner, and then he took her up to his hotel room. After some PG-13 action, he drove her back to her apartment on campus. Before he kissed her goodbye, he slipped $500 into her hand.

She was hooked.

Sara is a former sugar baby: a woman who goes on dates with men—her sugar daddies—for money. She doesn’t consider it selling herself the way a prostitute does because she never felt forced into sleeping with her “daddies.” According to Seeking Arrangement, the average American sugar daddy makes $250,000 a year; our city is home to more than 7,500 of them (about 2 percent of adult men in Boston) and more than 16,700 active female sugar babies. In 2012, the site designated Boston a sugar-daddy capital. “To me, it seemed very similar to OkCupid, with the additional lucrative component,” says the 26-year-old Wellesley native. “I was drawn to older guys anyway. Why would I do a dating website when I could get paid on this other one?”

She set up several more dates that week, and began meeting men at luxury hotels, apartments, and steakhouses in Boston; one daddy requested they meet in a parking lot outside a Pizzeria Uno off I-95. She says she had sex with 85 percent of the men she saw, who ranged in age from 45 to 75. Most were lawyers, doctors, and professors; some were married. There were vacations to Miami, trips to Vegas for gambling sprees, and “generally vanilla sex,” save for a few eccentric partners. One daddy, a 67-year-old cross-dresser, asked her to teach him how to put on makeup. Another wanted her to wear schoolgirl outfits for elaborate spanking role-play. All of them wanted to downplay the transactional element. “They want to convince themselves that the money isn’t a factor,” Sara says. “We would decide on a little gift, and he would slip a little envelope into my bag. The girls that are very money-hungry, that really turns guys off. When you’re more subtle about it, the more money you get.”

Eventually, she locked in a few regulars who paid her about $3,000 a month. Supplemented with mid-week one-offs for $500 a pop, her take-home was enough to support her even after she quit her post-college job. With $80,000 in her bank account, she started graduate school in New York this past fall and gave up the game—but she doesn’t regret her time sugaring. “It’s not that I had no sense of self-worth,” she says, “but when I realized I could get paid for what I was doing for free, it taught me to capitalize on my indifference toward sex. I know that’s not the greatest outlook, but I’m still evolving. Now I’m still trying to figure out what I would get out of a normal relationship.”


We Overinvest

A letter of warning against sleeping with a Startup Guy.

I’ve dated hockey players, engineers, lawyers, teachers, and podcasters in this city. But there’s one brand of Bostonian that should come with his own warning label: Startup Guy. I fell for one once, and I hope my story of heartbreak saves my millennial sisters from the hassle.

You’ve probably already met Startup Guy on Tinder. He’s that twentysomething wunderkind hawking a shiny self-made business based on an app that he’s convinced will change the world. He spends his days selling his sensation to wealthy investors; he spends his nights focusing those flawless marketing skills on you. Ever the salesman, he’ll hurl compliments until you’re clawing your clothes off. Then he’ll say you have the most amazing ass he’s ever seen. Always be closing.

Startup Guy flaunts his money to match his newfound rock-star status; that makes for powerful foreplay. The night my Startup Guy brought me to the W hotel for cocktails (where, surprise, he often brings potential investors) remains the hottest date I’ve ever had. He slid his credit card down for a room—just a five-minute Uber ride from my apartment, so extravagant—where we said and did things I still can’t fathom.

But Startup Guy’s wild moves have dubious origins: As a teen, he was roundly ignored by the other sex, so he learned by watching, not by doing. And now he wants to try out those porn-fed chops on you. Somewhere along the way in his nerd-boy head, intimacy and Internet moves got wrapped up into one. He’ll lick the perspiration off the nape of your neck and whisper in your ear that he loves the taste of your sweat. Trust me, you will succumb.

And yet, Startup Guy’s mojo is a fragile egg. And that’s what makes him dangerous. Anyone who challenges him about anything instantly becomes the anti–Startup Guy. One year into dating him, I dared to debate Startup Guy on the concept of implementing in-app purchases (seriously, ladies, I could not make this up). He was stunned to discover that I had thoughts and opinions different from his. Three days later, he was gone—reassured, no doubt, by the thousands of other women around here who are happy to get laid by the future Mark Zuckerberg.

It took me a while after he went silent to realize that Startup Guy was already married…to his startup. It’s inseparable from his ego; it’s what made him a man. So, ladies, remember, Startup Guy is a hot, fun mess, but you’ll never be more than a mistress.

In solidarity,
Loren Savini


It’s not unusual for things to get hot in the kitchen—after hours—in some Boston-area restaurants. / Photograph by Jeff Brown


We Get It On at Work

The after-hours restaurant scene is as salacious as you thought. By Alexandra Hall

Jim Solomon, chef-owner of Brookline’s the Fireplace, once walked in on a former manager and a server entangled in the restaurant’s kitchen. He wasn’t surprised. In fact, that sometimes happens after a shift when the booze starts flowing, Solomon says: “We’ve all lived stuff like that. It’s just rampant. You couldn’t write a book about [all that] happens, because it’d be too heavy to pick up.” Later, the manager would propose to his one-time hookup.

Solomon, a longtime industry veteran, is by no means a bystander. At least, he wasn’t (the award-winning chef, 51, is happily married these days). But as a line cook in his twenties, Solomon got caught by a GM in his own steamy tryst. “The girl and I ran through the kitchen and down the hall with our pants around our ankles,” he says. “We’d been in the restaurant, partying all night.”

It’s not just the fun that fuels libidos, Solomon says. It’s also the demands of restaurant work. “The nights are long, the physical work is hard, the atmosphere is incredibly fast-paced, and the pressure not to mess anything up is super high,” Solomon says. It all builds camaraderie among the staff the way being on a sports team or in the military can. “It’s that foxhole bonding, where you made it out of a particularly stressful train wreck of a night together, with incredible circumstances that no outsiders can understand. It takes a thrill-seeking person to survive in a restaurant. They love the rush of the battle, the energy and adrenaline.”

Solomon has had to hire an attorney for a (now former) manager who was sleeping with the staff, and he’s weathered two employees sleeping with the same hostess. He even found himself being a character reference at the police station after punches were thrown in the kitchen over a married cook who was sleeping with a former manager. “The more scandalous it is, the more they like it,” he sighs.

The consequences aren’t always shameful, of course. Plenty of well-known restaurant couples began as work flings: Deuxave chef-owner Chris Coombs met his wife, Vika, when she was a server in his upscale bistro; Catalyst executive chef William Kovel and his wife, Sara, connected on the job at the Four Seasons; Carolyn Johnson, chef at Concord’s 80 Thoreau, met her husband—local chef Bill Flumerfelt—while they were coworkers at Icarus; and chef Jeremy Sewall was a line cook at L’Espalier when he got sweet with the pastry chef, Lisa. They’re now married and co-own Lineage.

As for Solomon? He recently installed cameras in all the back rooms of the Fireplace. “I expected a degree of that behavior,” he says, “but I don’t accept it. I’m trying to get tougher.”

Sex in Boston: This Is How We Do It

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