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


She wasn’t a sex worker while studying at Tufts. She just had sex…and got paid. (See #5.) / Photograph by Jeff Brown

As the rest of the country joins the sexual revolution of the 21st century, we Bostonians can sit back and wonder what took everyone so long to get here. Gender fluidity? Two years ago, we were among the first states to cover gender reassignment surgery under state insurance. Transgender rights? In 2011, we passed legislation that protects rights for all, including transgender people, in matters such as employment, housing, and credit. And in our finest hour thus far, we were the first state in the union to legalize same-sex marriage, more than a decade ago.

Our enlightened attitudes have paid off big: LGBT individuals now make up nearly 5 percent of the metro area’s population, while the state is home to more than 21,400 transgender adults. Ever tech-centric, we’ve continued to churn out ways for people to connect and hook up, mostly in the form of digital apps such as the Cambridge-spawned OkCupid dating site and the Kendall Square–based Manhunt portal for gay singles.

What makes us so uniquely suited to lead the neosexual revolution? Like good New Englanders, most of us prefer to leave our neighbors well enough alone. What happens in the bedroom stays there, and we’ve made sure our laws protect and defend that position. And our progressive attitudes toward sex in particular are no doubt buoyed by the annual influx of more than 250,000 college students on their own missions of self-discovery.

But when we need to speak out, we do. Beginning in the 1980s, Boston’s Fenway Health implemented radical public health initiatives to treat the HIV/AIDS community and encourage open discussion of sexual practices, a critical cultural change that helped stem the spread of the disease. Even Mayor Kevin White acknowledged in the 1970s that a little sin never hurt anyone when he designated Boston’s red-light district, known as the Combat Zone, as an official place of adult entertainment where peep shows and prostitution could thrive without too much policing. And just last year, we all marched—together—in the Saint Patrick’s Day parade for the first time.

When the world wants to know what the 21st-century sexual revolution looks like in practice, it should turn to Boston. Which is exactly what we did for this story. How do we turn each other on and how do we get each other off?

To find out, we conducted our first-ever sex survey, and interviewed dozens more people to get a nuanced view of our distinctly Boston mating habits. We learned a lot: We slip between genders, pick the wrong partners, hold flogging parties in our living rooms, and want our genitals to glow in the dark. We are college students who have sex for money; middle-aged suburbanites who swing on the weekends; and soccer moms who screw their Internet flings while the kids are at practice.

And no matter how we fornicate, mate, couple, and screw, we’re doing it around six times a month—the national average—most frequently between dinner and midnight.

Here, a deep dive into sex, right now, in Boston.

* Names with asterisks have been changed for privacy reasons.


We Screw Below Our Pay Grade

She’s type A and he’s not even together enough to have a type. Introducing the beta male. By Brooke Jackson-Glidden

On my first day at Boston University, I went on a date with the perfect guy: tall, beautiful, and fit, with a paid journalism gig. He came straight from the Upper West Side in New York City with excellent taste in suits and pizza, and he treated me like a lady. When he brought me back to his dorm, I met his friend Dirk*: a doughy Rust Belt guy with a weed habit and a top score in Minesweeper.

I slept with Dirk that night.

I’m a sucker for the beta male, the term famously used by former Newsweek writer Jennie Yabroff to describe film producer Judd Apatow’s protagonists: pot-smoking, joke-cracking underachievers with a few extra pounds and no extra cash. At 18, I’d watched Apatow’s Superbad more times than I could count, I could recite Knocked Up verbatim, and I couldn’t shake a confusing sex fantasy involving Jason Segel in Forgetting Sarah Marshall.

A beta male is the ultimate nondemanding boyfriend: He’s never competitive and doesn’t mind your focus on work or school. He’s always available to hang out and watch a movie, and he doesn’t care if you borrow his Baja hoodie for a few weeks. His constant one-liners keep the mood light, and he’s happy to be your boyfriend, hookup, booty call, or anything in between. Really, with his dad bod and knobby-kneed lack of physique, he’s just confused about why you talk to him in the first place, but he’s grateful you’re willing to be with him, with or without clothing. Because the sexpectations are low, the relationship is easy.

For six months, I went along with Dirk’s three-bowls-a-day schedule. At first I’d text him times to meet up, until I found myself waiting for his texts. “Date” night usually involved a trip into Allston to hang out at his frat. We were never exclusive, and his cuddly-dork appeal wasn’t lost on other girls. Eventually, I was the workweek girlfriend. I’d move in on Monday, spend afternoons watching The Real World with his roommate, and then take my toothbrush back to my dorm on Friday. On weekends, he’d bring another girl home, and I would try to find someone else to bang that night.

At some point, my beloved beta boy began pulling some alpha moves. When we did hook up, he’d kick me out of bed at 5 a.m. and critique my appearance after sex. But every time I voiced the fact that it wasn’t fun anymore—that maybe I’d constructed his beta-ness in my head—he would make a sarcastic Archer reference, offer up a bag of Lay’s Sour Cream & Onion, and flash an endearing grin. I’d laugh. He was harmless. It was easy. Time after time, I’d grab a handful of chips and get under the covers.

Eventually, I outgrew my beta-male phase. I would much rather be with someone insightful and driven than a guy who writes Harold and Kumar fan fiction. I’d like to think my days of cute-slacker sex are behind me for good. But make no mistake: My heart still belongs to Jason Segel.


We Swing

Joe* was a fortysomething dad in the ’burbs who hooked up with swingers to escape his failing marriage. Until one night, when a married couple he met at a Plymouth bar pushed him too far. As told to Alexandra Hall

This guy tells me on the sly he wanted to humiliate his wife sexually, and they’d talked about it, and she was okay with that. But I didn’t know what was going on and it was late—like 2 [a.m.]. I go over to their fucking gorgeous house in Scituate, and it’s just us three; all of a sudden he rips the shower curtain off the shower and throws it on the ground. He wanted me to pee on her! And I thought the guy was going to kill me—because when do you see a shower curtain on the ground when someone doesn’t get whacked?

I said, “Sure.” The thing is, I was so scared after thinking I was going to maybe die, I actually couldn’t even pee. I had to keep taking a break to go get another beer and try to relax. And the wife and the husband are sitting there naked, and we’re all waiting, and it got super goddamn awkward till I could finally make it happen and we could all get it on.


We Get Old (But Still Want Some)

Gay, newly single, and thirtysomething, Scott contemplates his hookup potential. By Scott Kearnan

“Dating pool” is a misnomer. The singles scene is a river. Even while you’re lazing in love on dry ground, it continues to rush by. And when it’s time to jump back in, it’s easy to get crushed on those jagged rocks. Especially when you’ve aged out of the kiddie zone.

Fact: Gay years are like dog years—they add up a lot faster than straight years. I was lucky enough to split my twenties evenly between two long-term relationships, but when the second ended a few months ago, I suddenly faced a dramatically altered terrain. Since I’d been gone, a new breed of farmer-plaid-wearing queer hipsters had appeared on the scene. And they wanted nothing to do with this past-his-prime Old Yeller.

Gay culture’s emphasis on youth is no secret, but I thought maybe it was the self-doubt of being recently single that was working against me. So I self-prescribed immersion therapy, and booked myself a Halloween weekend in the gay enclave of Provincetown. I anticipated an orgy, but the only thing I made out with was a bag of Fritos. I even bought rubber underwear from a fetish shop (why, Scott?), with the same gutsy yet misguided attitude of a chardonnay-swilling divorcée wriggling into leopard-print hot pants; I modeled them for the hotel mirror only.

Back in the city, age-appropriate opportunities for guys like me are few and far between. Sure, there are a handful of parties that don’t feel like Mickey Mouse Clubs: Monthlies like Boyfriends, at Jamaica Plain’s Bella Luna, and downtown’s divey Fuzz at the Alley cater to bearded, artsy crowds that skew a little older. But with LGBT progress has come the shuttering of many gay bars. Here in the birthplace of same-sex marriage, so the rallying cry goes, why should we shoehorn ourselves into separate venues?

In search of guidance, I turn to the Welcoming Committee (TWC), which plans LGBT-focused social events across the country. “Gay guys in their thirties still want to do the same things as gay guys in their twenties,” says TWC founder Daniel Heller. “They just don’t want to feel like they’re—you know, the old ones.” Preach on, I tell Heller as we grab pre-drink drinks at a Financial District bro bar en route to the Fellows, TWC’s new monthly meet-up aimed specifically at thirtysomething gay dudes. He’s right. I don’t actually feel old. It’s just that I’m not a boy, and not yet a daddy (that’s subculture-speak for “silver fox”); I’m caught between worlds, and reminded of it whenever a mention of Madonna ends in a Metamucil joke.

The Fellows is pretty much an extended happy hour with good hair. But it offers a much-needed social space for guys like me who still want to get a little messy on a weeknight—away from the screech of twentysomethings blowing their first big-boy paychecks on kamikaze shots. I chat up the founder of a gay craft-beer club; fling a few pop-culture references over the head of a nice Spanish guy with halting English; and meet an adorable ginger with whom I’m slightly smitten, though I suspect the feeling is not mutual. (Am I too old? I wonder as I scroll through his LinkedIn profile later.)

There’s no way to ignore the great migration online. The new faces were nice because they were just that—faces, not dick pics. When Cambridge-based Manhunt launched its gay hookup website in 2001, it instantly became the Domino’s Pizza of dong: Log in, browse the available toppings, order a torso. Grindr and others followed. The problem? I haven’t dabbled in online hookups since I was a teenager in a one-stoplight town, where AOL chat rooms were used for a very utilitarian purpose. (“You? Me? Have a pulse? Cool.”)

But guys who grew up with smartphones in their hands treat Grindr like Facebook with more skin; sometimes they even (gasp!) just want to talk. What’s that about? “I don’t need an app to talk,” I sigh to a friend over drinks at Club Café. The Back Bay joint is the legacy act among Boston gay bars. We’re visiting on a quiet Wednesday, seated at the front bar beside a James Franco–looking cutie who is feeling conversational. He’s witty and well read, from Georgia. He’s a Starbucks barista. He just turned 21.

“So, where do you live?” he asks me, pulling on his coat.

Old(er) dog, meet new tricks.

Sex in Boston: This Is How We Do It

1–3   •   4–7   •   8–11   •   By the Numbers   •   He Said, She Said   •   Campus Sex   •   BDSM