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


We Have Dry Spells

Radio personality Kennedy Elsey, of Mix 104.1’s morning show, tells us how she broke her two-year no-sex streak.

They say you have to kiss a lot of frogs to find your prince. I think you have to avoid lip-locking with anything froglike to find a decent human you want to watch Netflix with.

For those of you not keeping track at home, I spent the first two years after breaking up with a long-term boyfriend going out with a bunch of duds. It was the dry spell of all droughts: like, no sex. At all. My morning-show cohosts, Karson and Salt, were so worried that they created online dating profiles for me on Plenty of Fish and OkCupid. I was a big hit with unemployed guys and dudes living at home with their mothers.

Then a year ago I met a guy we’ll call the Mountain. Truly, he is a giant of a man. We connected through mutual friends at Beacon Hill’s Carrie Nation one Friday night. I had been pregaming, and by 10 p.m. we were making out in the alley next to the bar. The Mountain then took his motorcycle and all his shit and moved to California for a year. I filed away our hot alley tryst and moved on with my life. And my bad dates that led to zero boozy make-out sessions…or anything else.

A year later (dry spell still intact), he moved back. He set up three—three!—dates and I bailed on all of them. I was scared that I would fuck it up. But he persevered, and on the fourth try we met at the new Mare in the North End, downed a few glasses of wine, and ate all the oysters. I once said I’d never let a man come to my house—and that if one snuck by, we’d do it in the guest room. I mean, no way do I want the lingering scent of stranger sex in my inner sanctum. None of it mattered that night. Just like that, the slump was busted.

I was an hour late for work the next day and received a standing ovation from my coworkers. (Hey, I’d been lamenting my flat-lined sex life for the better part of three years.) The Mountain and I are still together, taking things very slowly. Is he the prince I’ve been waiting for? To be honest, I haven’t been holding out for royalty. But damn if he doesn’t know his way around a Netflix queue.


We Switch Genders and Stay Married

Michel was a woman when he married his husband in 2005. Neither spouse realized that Michel, now in his early forties, would one day transition to a more masculine gender. Today, Michel takes male hormones but won’t have sexual reassignment surgery. Transition hasn’t always been easy for the Somerville couple, but it’s barely caused a hiccup in the bedroom. As told to S. I. Rosenbaum

My family said that I was going to make my husband gay by transitioning. But I think I did by marrying him. The first time we slept together, as we were undressing, I said, “Do you like surprises?” I had a piercing, and I didn’t want to shock him. He paused for a long time, and then he said, “Okay.” He told me later that in that moment, he was like, Was Michel born a female? He wondered if I was going to have a penis. Then he thought, Well, I like Michel, so it will be okay.

I didn’t start to think about transitioning until years later. One night I was getting ready to go to a meeting and looking in my closet, and I thought, I can’t wear another dress. Then I asked myself, What is that about? Is that about clothing? It’s not just about clothing. I thought about it, and I talked to my husband and said, “What if I quit being female?” He said, “Honey, you do whatever you want.”

With my husband, when we have sex now, it seems very heterosexual. It would look heterosexual to a casual observer. My body isn’t particularly male, even after hormones. I do enjoy wearing a strap-on—but what I don’t enjoy is the process of putting it on. It takes a long time and it’s kind of fiddly, and then you’re like, “Am I tearing a hole in you? I can’t feel what I’m doing.” It’s not a part of your body, and you really can’t tell if you’re hurting someone the way you can with your fingers.

I think almost every aspect of transition has opened new possibilities. There’s a lot more middle ground to inhabit. I’m not stuck in one gender role. It’s been freeing. But in my relationship with my husband, I don’t think anything has changed. I think we started out in a gender-destabilized place and we’ve been in it ever since.


We Accidentally Sleep with Our Roommates

It happens all the time. Katie,* 30, and Max,* 22, were platonic roommates for six months before they began having sex. They keep separate bedrooms and share their Jamaica Plain apartment with a third roommate. Neither is sure their relationship is a good idea. By Brooke Jackson-Glidden

Katie: We first met on Skype.

Max: I wanted to make sure you weren’t scamming me out of an apartment.

Katie: I was just concerned about you being a person with social skills.

Max: We started to be pretty good friends last fall. We started hanging out and tensions mounted.

Katie: Can you use a different word? Seriously, dude.

Max: Then it was Valentine’s Day. We weren’t dating, but we were going to a storytelling session called Mortified at the Coolidge Corner Theatre. This wasn’t a romantic gesture, just a thing we did as friends.

Katie: We started to joke about that New York Times article—

Max: “The 36 Questions That Lead to Love.” Katie started asking me those questions.

Katie: No, you pulled them out and started—

Max: Who started asking is under dispute. The point is, if you start to ask each other those questions, that’s a signal.

Katie: I’ve asked a lot of my friends those questions.

Max: Yeah, you’ve had sex with a lot of your friends.

Katie: We came back here drunk. You kissed me, and I said, “This is a bad idea.”

Max: We had sex anyway, wondering, Is this just us being drunk? Or is this something else? We woke up the next morning and had sex again, completely sober. That’s when I realized, Oh, this isn’t just a total mistake. I really want this to happen.

Katie: I’m the kind of girl who would have been perfectly fine completely ignoring it, maybe talking about it sometime later.

Max: And I was like, Hey, does this mean I have to move out? Because she’s my landlord. For the first few weeks we hid it from our [third] roommate.

Katie: I like having a third person around. I don’t think I would want to live with just you.

Max: It’s convenient. I don’t have to trek across the city to go have sex. [But] things can get banal and mundane. It becomes domestic really quickly.

Katie: We know I’m leaving in June, and when I get back in the fall, you’ll be moving out.

Max: I think we would continue seeing each other.

Katie: I think we’d have to see how it goes.


We Get Booty Calls While Our Kids Play Soccer

Confessions of a recent divorcée, who figured out how to work around her extenuating circumstances.

Divorced in Chestnut Hill, I found myself browsing the man market again after 25 years. Dating now has all the efficiency of online shopping: Plug in your preferred size, income, age, and voilà! An array of men with handy (if optimistic) tag lines—from “Lust It or Leave It” toPlymouth Rock ’Em”—areat your disposal.

So I shopped.

I wasn’t prepared for the, uh, merchandise to look so old. But I got over it—likely because of the surge of hormones roaring through my loins. I had kept my knees mostly shut before marriage. Suddenly, who cared? And, as I happily discovered, what older guys lack in physique, they make up for in technique. Yowza.

Only one problem: kids at home. This is not insurmountable. Here’s how I did it. —Anonymous

I perfected the late-night booty call 2.0: My 12-year-old daughter would typically fall asleep by 11 p.m. So “Lobster Man” would come over late and leave very early the next morning. The only witness was the dog, who developed a Pavlovian response to the text alert from my beau waiting outside. We’d use my son’s bedroom—he was away at school—on the third floor. When he returned on breaks he was none the wiser. New stains on the mattress? Damn dog.

I used my time wisely: My daughter had soccer practice, guaranteed, twice a week for two hours. I’m not ashamed to admit that sometimes, that’s all it took. Enough said.

I bought toys—and hid them: I threw my stash of new paraphernalia on top of old tax returns in the back closet. Those files never saw so much action.

I covered up telltale signs: Mussed hair? Accidental hickey? That sweaty sheet smell? Dead giveaways. I’d have perfume and makeup at the ready when I needed to cut it close. My daughter once asked, “Mom, why did you take two showers today?” I said that I believed in being extra clean and someday she would, too.

I never let go of my phone: Sexting? Oh yes. But please note: I used to let my kids borrow my phone. Never, never again. Did I say never? Never. In fact, my phone stays on my body at all times. Nothing stops breakfast in its tracks like a naughty text hitting your screen when your phone is face up on the table.

I guess I’m proof that anyone, at any age, can get broadsided by that thundering train called Sex Drive. At least when my daughter goes crazy like this, I’ll be able to handle her with empathy, support, and…a chastity belt.

Sex in Boston: This Is How We Do It

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