Chapter Two
Be My Sugar Baby
Jem figured it would take some time for the whole sugar-baby ball to start rolling.
Background checks, police clearances, identity verification—this wasn’t just some online hookup service.
And surely whoever was on the other end would want to, like, think things through or whatever.
He probably should’ve known better; rich people treated sugar babies the way they treated everything else—the newest thing was the best thing.
Jem got his first response half an hour after he received notification that his profile had been cleared and activated.
They wanted to meet the next day at noon.
As he stared into his closet that night, he called Ivy and said, “Hey, what do I wear to meet a potential sugar mama?” because Tori’s idea of fashion was a clean T-shirt and pants with enough pockets to double as a tool box.
After a five-minute FaceTime call, Ivy picked an outfit that embodied pool boy—deck shoes, white pants, bright polo, sunglasses—and pronounced him fit for consumption.
Which was about right, Jem thought, because the woman who sat across from him in the private back room of the high-end café she’d selected for this meeting looked like she wanted to eat him.
“You must be Jem,” she said smoothly as she rose from her chair. She was Caucasian, slender, with a bright purple manicure and highlighted red-brown hair. She could’ve been forty or sixty, though Jem guessed it was closer to the upper end. “I’m Caroline.”
Jem debated half a second before shaking her hand instead of kissing it. She had a firm grip and the kind of smooth skin that spoke of expensive moisturizer. “Nice to meet you, Caroline.”
“Oh, the pleasure is all mine,” she said lightly. Then, lips pursed, lashes fluttering, “Well, maybe not all of it.”
Laughing, Jem sank into the chair across from her. “That’s one way to break the ice, I guess.”
“I have some experience with first-timers.” She paused and actually seemed embarrassed by the implication. “Oh dear. I mean first-time… companions. Not virgins. Christ. You’re not a virgin, are you, Jem?”
“Not the last time I checked,” he answered faintly. This lady was dangerous.
Caroline laughed. “Okay, good. Now that’s out of the way, do you drink coffee? Tea? I personally love a flat white, or Jeremy makes a mean London fog.”
“How does Jeremy feel about iced coffee?”
“If he’s a snob about it, he’d better keep that information to himself,” Caroline advised. She took out her phone and sent a text message—their drinks order, presumably—and then placed it back on the table, facedown. “So, Jem. Can I tell you a little about myself, or is that too forward?”
“At this point I think it might actually count as going in reverse.” Jem could tell he was flushing, a little, but she was an attractive woman and her candor put him at ease.
If he was going to be interviewing for the position of sugar baby, he’d have to get used to conversations like these. At least Caroline made it fun.
She chuckled, then leaned back in her chair as a barista—Jeremy, presumably—came in to deliver their drink order.
When Jeremy left again, Caroline folded her hands around her coffee cup. “As I was saying, I’m Caroline. I’ve been widowed once and divorced twice and I’m just over the whole”—she waved a hand—“soul mate thing. But that doesn’t mean I like being alone.”
“I get it. I get tired of my own company too.”
“So you understand.” She smiled in delight. “It’s boring, rattling around in my big old mansion alone all the time, so I throw a lot of parties.”
Jem thought, Sex parties? and it must have shown on his face, because she shook her head. “Industry parties, Jem. Introducing people to each other. Networking. No fancy underpants required.”
To give himself a moment, Jem picked up his iced coffee and took a sip. Jeremy was a fucking wizard. He made a pleased noise, set the cup down again, and asked, “Fancy underpants optional?”
Caroline chuckled again. “Oh, that depends on the guests. But mostly they’re R-rated at most. For language, smoking, drinking. Occasionally other substances. So the first thing I’m looking for is a young, handsome, charming cohost. I have to say, you’re nailing that part of the interview.”
“Aw, shucks.” But he tapped his fingers on the table, because he did have to draw a line. “I’m assuming participation in the other substances is optional? The day job is not beyond occasional random drug testing.”
“Of course,” Caroline agreed. “I should have realized—you did say young professional, didn’t you? Can I ask what you do for work?”
He cleared his throat. “Ah, I teach kindergarten. Private school.”
“Shaping young minds,” she said approvingly. “How darling. Well, you don’t have to worry. You can abstain from anything that might get you in trouble.” Her smile turned mischievous. “In trouble at work, at least.”
Oh boy. Jem had a feeling he knew where the conversation would go next. “I appreciate that.”
Sure enough, Caroline took another sip of her coffee and then leaned forward. “Now, Jem. Let’s talk about you a little bit. Your profile says you’re open to negotiating more intimate arrangements. I’m sure it won’t come as a surprise that that’s my primary interest.”
“I may have guessed.”
“I can be a very demanding woman.” She smiled as she admitted this, maybe because she followed it up with, “And a generous one.”
Jem picked up the piece of paper she slid across the table and glanced at it. A number with a significant number of zeroes was written on the other side.
“This is what I’m offering on a monthly basis, as well as gifts—you’ll need appropriate clothing for the parties, jewelry, so on. I’d expect you to stay over on weekends, of course.”
“Uh-huh,” Jem said faintly, trying to process the number. Was this the beginning of his inexorable transition into prostitution and debauchery? Because from where he was sitting, it was a pretty sweet deal.
But….
With a deep breath, he raised his eyes to meet Caroline’s. Her gaze was shrewd, assessing, but not unkind.
“You’re turning me down,” she said mildly.
“Honestly, I think I’m more surprised than you are.” He gave her a weak smile and pushed the paper back toward her, as though she’d need it for something else. “It’s not—definitely nothing you did or said. You’re funny, you’re attractive, I think we’d have a good time.”
“But?” Caroline prompted.
He blew out a long breath and tried to put words to it. “Cold feet?” he said. “That’s not it exactly, just, uh. I’m gonna be real with you, the idea of getting paid that much for my dick is gonna give me performance anxiety.”
She broke into a peal of surprised laughter. “Now, I’m not sure I believe that.”
It was as close as Jem could come to explaining.
He shook his head slightly. “I think it all just got too real. I need some time for it to sink in, you know? And this is my very first, um, interview? I feel like there’s a difference between jumping in the deep end knowing you can swim and doing a polar dip. ”
“Hmm.” Caroline considered him. “I suppose I might be something of a shock to the system.”
Lady, that’s putting it mildly.
“I’ll tell you what.” She reached into her purse and withdrew a business card, which she passed across the table. “You go see what’s out there, and if you don’t find something that suits you, give me a call.”
Jem took the card and smiled. “Sounds like a plan. I will. Thanks, Caroline.”
Of course, the interview itself was fine. The debrief with Tori afterward, however—
“Tell me everything,” she demanded. “No, wait, if there were bodily fluids exchanged, I don’t want to hear that part.”
Jem was literally the one who taught her how to go down on a girl, once upon a time, but whatever. He rolled his eyes. “It wasn’t an audition. It was just coffee with a potential… client.”
“Uh-huh. And do you always discuss your dick size on your coffee dates?”
“Caroline did not ask how big my dick was.”
Apparently Tori had not anticipated this. “Wait, really?”
And—well. Jem made it a habit not to lie to her. “I wore the white chinos.” He’d bought them online, intending to make them part of his work wardrobe, but he’d only worn them to school once before Tori informed him why he would not be doing that again.
“Oh, so she’s seen it.”
The pants weren’t translucent, just… tailored. Jem sighed. “Tori.”
“Right, right, okay, I’m focusing. Tell me about her.”
“She was hot. Older, I don’t know how much, but like, at least forty, probably fifty. Definitely works out, hair and nails done on schedule. Beverly Hills type for sure.”
“I should’ve known you’d be cougar bait. Did you like her? Or was it, like, skeevy?”
“I mean, the first thing she said to me was a sex joke,” Jem admitted. “But she was funny about it. It wasn’t pushy or anything. I did like her.”
“Amazing. So you’re going through with it?”
“Uh. No.”
“Why not?”
“Tori, that lady would’ve rode me hard and put me away dead.”
“You mean wet?”
“I meant what I said. I was gonna be calling in at the start of every week ’cause I would’ve been too sore to get out of bed.”
Tori cackled. “Jem, she was like fifty years old. You don’t think you could keep up?”
“Without performance-enhancing drugs? She was gonna have my dick twice for breakfast and follow up with my shin bone for brunch if she couldn’t get a third helping.” Jem was more than happy to be of service, but he wasn’t sure his ego could handle that.
“Jem! Gross!” The cackles turned into breathless wheezes. “College Jem would’ve gone for it.”
He snorted. “College Jem would’ve done it for free and called it part of his education. But College Jem didn’t have to wrangle twenty five-year-olds come Monday morning.”
The smile in her voice was obvious when she said, “You’re still tempted, huh?”
“Oh my God, yes. For one night she could use me however she wanted. It’s the commitment to excellence that’s freaking me out.”