Neither could Jess. They hadn’t gone through a glass of wine before he put his hands on either side of Mia’s face and began kissing her. Mia expected herself to resist but instead was shocked by how instantly she was aroused—a sensation she hadn’t known she could still experience.
After a short make out session, Jess took her hand and guided her upstairs into an empty guestroom. He took off his clothes and so Mia took off hers as well. Then he went into the bathroom, turned on the shower, and beckoned for her to join him.
He leaned over—he was at least eight inches taller than she was, which was amazing considering Brian had been two inches shorter—and they began making out again while soaping each other’s bodies. Another thing Mia hadn’t done in a very long time. Then he bundled her up into a towel and spun her around and out of the towel, which he laid down on the bed.
He leaned over her again, kissing her until she was beneath him.
And then it was like being in a porn film. He performed cunnilingus, his tongue darting here and there, then turned her around for the sixty-nine. His cock was shortish and fat, but before she could really get to it, he lay back and reached for the condom he had at the ready. He rolled it on and pulled her forward to mount him. She rubbed the top of his penis against her vagina, feeling for the magic opening where he could slip in without jarring. He gave a jerk of his hips and in he went and Mia began rocking her pelvis, feeling him inside and feeling—for the first time in a long time—confident. As if she were kind of an expert. Like she really could be in a porn film.
Ride ’em, cowgirl, she thought.
And then he came when she was almost ready to come but didn’t. But it was okay she reassured him. She would, next time.
He left ten minutes later. Mia was too wiped out to notice or actually care.
Two weeks passed and then three. Three weeks in which Mia didn’t see or hear from Jess. At first, she was angry. But the emotion faded. She told herself she shouldn’t have been surprised. Men sucked, and Jess was just another example.
She went back to the rosé bottle, which didn’t disappoint, and dove deep.
A rare text pulled her out of her stupor.
Hey, it said. Want to hang?
Jess! She’d nearly forgotten about him. And once again, she couldn’t believe how excited she was to hear from him. She texted back: When?
He replied immediately. I’m with my bud. We’ll come by in twenty.
Jess’s friend Drew was kind of creepy, but Mia did her best to ignore him in favor of this opportunity to see Jess. She got drunk quickly. They all did. Then Drew left and she and Jess went upstairs. “I’m not going to do this,” Jess said. “You’re too wasted.”
This was the last thing Mia wanted to hear. “I’m not wasted. Come on,” she said, shocked by the note of desperation in her voice.
Jess hesitated but not for long. He took off his pants and Mia put her hand around his penis, noting once again his super-hard hard-on that only the young possessed.
But this time the sex was over far too quickly, and before Mia could stop him, he was gone. She grabbed a bottle of wine and went back to bed. And once again, before long, it was six in the morning and her head hurt like hell. She gulped some water and took another half of a sleeping pill.
* * *
A week later, at two in the afternoon, Jess showed up at the house with Drew again.
Mia, who couldn’t be bothered to pretend anymore, opened a fresh bottle of wine and poured them each a glass. They sat down at the kitchen table.
“So listen, Mia,” Drew said. “We have a problem.”
“We do?” This wasn’t what Mia was expecting. She didn’t think she knew either one of these guys well enough to have “a problem” with them.
“Jess told me what happened,” Drew said.
“What are you talking about?” Mia looked at Jess questioningly.
“He’s underage,” Drew said.
“Excuse me?” Mia’s first instinct was to hide the wine. If Jess was underage, he shouldn’t be drinking. She looked guiltily at the glass in front of him. “Why didn’t you tell me?”
“You didn’t ask,” Jess said.
So Mia did ask for proof. Drew claimed that Jess left his license at home. Mia asked Jess how he could do this to her and Jess looked scared and wouldn’t speak.
Drew got to the bottom line. He and Jess were going to blackmail her and wanted at least a hundred thousand dollars. They knew how rich she was. They’d read about her sectionorce settlement in the papers. And now she’d had sex with Jess, who was underage, and if she didn’t pay she was going to be arrested.
For the next three days, Mia was in a panic. How could this happen to her? She longed to tell someone, but whom? Her girlfriends wouldn’t understand. In fact, they’d be horrified. They’d say that this confirmed what they’d secretly suspected all along—that Mia was somehow a bad person who deserved to have terrible things happen to her.
But then it wouldn’t matter, because she’d be arrested. Her photograph would go viral. Her life would be over.
* * *
A couple of days later, Jess’s boss came by. He was a nice guy from a few towns over, married with a couple of grown kids who still lived in the Hamptons. He was a talker, and before long, probably because there was no one else she could tell, Mia told him what had happened with Jess.
He was furious. He knew Jess well. Jess had gone to high school with his daughter. Jess had been telling the truth when he said he was in college. He was twenty not seventeen.
A couple of days later, Jess came over to apologize. It wasn’t his idea he said. It was Drew’s. He’d been boasting to Drew about how cool it was that he was having sex with his idol’s ex-wife and then Drew jokingly came up with this plan and Jess thought he was kidding but Drew was fucking crazy and he definitely wasn’t talking to that kid ever again.
Mia forgave him. Partly because she was a nice person and partly because she just couldn’t stand to listen to Jess and his lame excuses anymore.
Mia did eventually tell her friends, and they had a good laugh about it. In the end, Mia was like most middle-aged women whose cub adventure would become just another one of the bizarre and inexplicable things that would happen to them in the next few years.
Others, however, take their cubbing to the next stage.
The Cub Club
This happens when a woman moves from what she assumes will be a one or two time event to a more regular arrangement. The cub begins to spend the night. Now there is a very good chance he will move in.
And there he is, suddenly living in your house.
Some questions:
How do you introduce your cub to your friends? How do you explain why he’s living with you after a month? What if your friends don’t like him or, even worse, what if they just plain ignore him?
That’s what happened to Sassy and me.
* * *
We were barely two weeks into June when James appeared.
He sat uncomfortably at the edge of the kitchen table at Kitty’s, surrounded by the girls—Sassy, Tilda Tia, Marilyn, Queenie, me, and Queenie’s teenage daughter.
I assumed he was a friend of Queenie’s daughter. I didn’t think about it much, because everyone was talking loudly, and as happens in these cases when one male is outnumbered by a bunch of women, James quietly disappeared into the background.
So imagine my surprise when I stopped by Sassy’s place two days later and James was there.
It was noon and Sassy seemed a bit embarrassed, but she had a quick explanation. “James is helping me with my new phone.”
I nodded. As I would later learn, becoming indispensably helpful—i.e., programing the iPhone, showing how to connect music, and even going for alcohol and food runs—is one of the sneaky moves cubs use in order to get a woman to house them.
But I wasn’t th
inking about it at the time. Indeed, I didn’t think about it again until Sassy had a barbeque and James was there. Again. He’d brought the meat. But still.
James was starting to annoy me slightly. Was he always going to be there? And why? He was at least twenty, twenty-five years younger than we were. What the hell could be so interesting about a bunch of middle-aged women doing their own thing that would make him want to hang around?
The next day, Tilda Tia and I went for a bike ride. I immediately asked her about James. What did she know about him?
Tilda Tia shrugged. “He’s a real estate agent.”
“He’s old enough to have a job?”
“He’s almost thirty. He broke up with his girlfriend four months ago, so I guess he’s bored.”
I didn’t ask how old the girlfriend was. Instead, I asked her how Sassy had met him. I could have asked Sassy myself, but something about the situation prevented me.
Tilda Tia was vague. She mentioned something about an evening at a club, back in the days when she was still cubbing. Tilda Tia was no longer cubbing herself and had instead moved on to Tinder.
Another month passed. Every time I saw Sassy at a party, I was surprised and annoyed that James was still hanging around. He would get her drinks and seemed to be on friendly terms with all of our friends. I was suspicious. But when I asked around, everyone said they “loved” James. He was handy and he was happy to be the designated driver.
And then it was casually mentioned that he was staying at Sassy’s. For the moment, anyway. He’d had a share in another house, but it was only for one month. So now he and his VW bug were temporarily parked in Sassy’s driveway.
This is another typical cub ploy: suddenly moving in when they’ve lost a place to live.
Like James, the cub always claims to have a place to live when you first meet. Then the “place to live” becomes someplace less defined—a place to “crash” perhaps. And then the place mysteriously disappears altogether and the cub is homeless.
And where better to stay than with you?
Naturally the cub reassures—and cautions—that the arrangement is only temporary. Cubs know that the women who house them are not looking for forever. Forever is too soon. It’s too raw, it’s too scary. Especially when you don’t know where you’ll be three months from now.
Which is why, perhaps, Sassy chose to keep it a secret.
Although I suspected that Sassy and James might be having conjugal relations, I couldn’t really confirm it. There were no tipoffs, no tells. No sidelong glances. No handholding. No whispers in the hallway.
While Sassy and I were out talking on the deck, James would usually be in the house on internet central. I’d pass him on my way out and we’d wave hello. When Sassy and James did interact, a lot of it seemed to be about scheduling.
Was he some kind of assistant?
The day came when I skipped a bike ride with Tilda Tia and in the middle of the morning, having driven to town to post letters, I decided to pop over to Sassy’s.
The cars were there, so I went inside. The place was empty. I wandered into Sassy’s room just to be sure.
The bed was a mess, and the pillows on both sides had been used. On the floor was a torn packet of foil.
Was I the only one who didn’t know?
“Why didn’t you tell me?” I asked Tilda Tia later that day.
“Tell you what?” she said. As usual, she was distracted with Tinder and her next date.
“Sassy and James are not just friends. They’re sleeping together.” I said this thunderously, as if I were Charlton Heston in one of those religious movies.
“So?”
“She never told me they were.”
“She didn’t tell me either,” Tilda Tia said. “Which means if she didn’t tell us she doesn’t want us to know.”
“Fine. We know nothing,” I said. Nevertheless, I was determined to ask Sassy myself.
“Are you and James . . .” I could barely bring myself to say the words.
“Do you think I’m going to end up with a guy who’s twenty-five years younger than I am? Come on,” Sassy said.
Sassy quietly unhoused her cub at the end of the summer.
And perhaps, in keeping with the clandestine nature of her cubbing adventure, Sassy and James are still friends. James is going to visit soon and he’s bringing his new girlfriend. Sassy can’t wait to meet her. And neither can we.
The Future
What we don’t know about older women/younger men relationships is a lot. In fact, we hardly know anything at all, mostly because there haven’t been enough of these relationships to draw any significant conclusions.
But it is likely there will be more and more of them in the future. At least according to the internet, which is filled with sites exploring the older woman/younger man dynamic. Sure, some of the couples look like models, but more often it’s just regular women like Meegan, forty-two, who has her own vlog and sums up the reverse-age romance like this: “Hey ladies, you’ve tried the younger woman/older man thing, and how’s that working out for you—huh?”
The future of cubbing is wide open.
chapter five
The Fifteen-K Face Cream, The Russians, and Me
“Where’s your apartment?” people would ask.
“The Upper East Side,” I’d reply, and they’d roll their eyes. The Upper East Side wasn’t cool. It was boring and shut down after sundown and there were too many strollers and too many old people and so no one interesting lived there. On the other hand, the fact that no hipsters or groovy people wanted to be seen there made the apartment, by New York City standards, somewhat affordable.
Unfortunately, it was the only thing in my immediate neighborhood that was.
Welcome to Madison World
I discovered this on my second morning when I set out to take a stroll. I hadn’t gone half a block when I passed a window display of glasses and, reminded that I could use a new pair, went inside.
With burled wood walls and cases decorated with cigar boxes, the small shop was more like a gentleman’s club where they happened to sell spectacles. A dapper young man came over and asked if I wanted to see anything. I pointed to a pair of tortoiseshell frames. I replaced my glasses with the empty frames. But I then had no idea how I looked, because without my glasses I was blind, like Piggy in Lord of the Flies.
“I don’t know,” I said. “How much are they?”
“Three thousand dollars,” he said casually, as if this were the going price for frames all over the world.
Three thousand dollars? Again?
“And then you have to add in the cost of the actual lenses. That’s another thousand each.”
In other words, five thousand dollars for glasses.
“Great,” I said, backing away with a big smile on my face.
I left the store feeling self-conscious. I didn’t belong in this neighborhood and everyone in the neighborhood knew it.
Madison World, I called it. Located between Fifth and Park, it was an Aladdin’s cave of gold and silver, of diamonds and jewel-encrusted watches, of crocodile shoes and dresses scattered with hand-embroidered crystals. In Madison World, women dressed in outrageous fashions and paraded up and down the street like it was the most glamorous runway in the world.
They knew I was an interloper. They could tell by my creased cotton pants, both practical and comfortable. They knew by my hair, untouched for weeks by the smoothing heat of the blow-dryer. But mostly they knew by my shoes—Havaianas flip-flops.
I was going to have to learn how to dress again.
Madison World Sticker Shock
You’d think I’d do the obvious thing: go into a store on Madison Avenue and just buy something. But shopping in Madison World doesn’t work that way. It’s a complicated process. There’s a lot of interaction with other humans who are
there to decide whether or not they are going to sell you their wares, whether or not you can afford them, and whether or not you should even be seen in them. Purchasing something in Madison World is like trying to get your kid into an exclusive private school.
Actually, the private school process might be more pleasant because you don’t have to get undressed in front of strangers.
But first you have to find something to try on.
This is not as easy as it sounds. Expensive clothes are often chained to their racks like packhorses at a dude ranch. This is not to discourage stealing, which would be all too apparent given the fact that these “clothes” are often elaborate affairs that can’t easily be hidden, in, say, a regular shopping bag. No. The clothes are chained as a stern reminder that you’re not really supposed to handle them. You will need the assistance of a wrangler before you can even get close to getting them into the dressing room.
If you’re not already a tich intimidated, you might be when you see the dressing room itself. Chances are it’s more expensively furnished than your apartment. It may have a couch or two and definitely a few throw pillows. You can see how someone really rich might be encouraged to have an afternoon party there.
And this brings us to the best part of shopping in Madison World: You can drink. Most stores serve champagne. And unlike the exorbitant prices that restaurants charge, the champagne in Madison World is free.
You’ll want some of that champagne for Dutch courage. In addition to the couches, the dressing room likely has a platform centered in front of a large, three-sided mirror. You may be able to survive your own gaze, but can you survive the gaze of the entire sales staff? Because while you are changing, you will inevitably get that knock on the door. “How are you doing?”
What the wrangler really means is: How are the clothes doing?
Is There Still Sex in the City? Page 7