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The Billionaire and the Waitress by Constance Masters – Sample

Chapter OneThe Billionaire and the Waitress by Constance Masters

Josh chose a booth in the far corner. He liked to sit where he could scope out the entire room. There wasn’t a more interesting way to learn about what people wanted and needed than to watch them, except for maybe talking to them, but he always started by observing. Besides, it was enjoyable and one of the perks of being the boss.

He’d been in lots of cafés and diners on his travels. This one was a little different; he liked the atmosphere. It was quaint with lace curtains on the windows and pale blue vinyl on the benches and stools. The black-and-white checked tiles on the floor were a stark contrast. The tables were so clean he could almost see his face in the polished white Formica. This place was warm, welcoming, and homey.

“Can I get you something?”

A waitress appeared from nowhere and bent over to pour him a glass of water. The restaurant’s decor faded into the background as the pretty young woman plucked a pencil from behind her ear and stood there patiently, pad and pencil in hand. “Ah, yes, please. I’ll have a cup of coffee, black.”

“No problem.” She flashed him a brilliant smile and disappeared behind the counter.

He couldn’t help but watch her as she busied herself. Her long red hair was in a bun, but still a little untidy. Wispy curls were trying to escape from the tiny peaked hat that was part of her short sky blue uniform. It made him wonder how long it was, her hair. If that knot came undone, how far down her back would her tresses fall? All the way to her shapely bottom?

“Thank you.” he said, offering his own smile as she came back to his table armed with a tray.

“The donut comes with the coffee, free of charge.”

“Thank you, that’s very nice of you.” He wasn’t a donut lover, but he appreciated the offer.

“You’re very welcome. I haven’t seen you around here before, have I?”

“No, I’m just passing through.” At least that was the plan so far. He never knew what might come up. He was always open to staying in a town a few days if something interested him enough.

“Have you been somewhere or are you on the way to somewhere?”

“I’ve been on a vacation, mostly. I’ll be on my way back home soon.”

“What do you do, as a job, I mean?”

“Pardon me?” He balked a little at the question, but this young woman’s face was open and honest. There wasn’t an iota of recognition on her face. He realized she was just being friendly, she had no clue who he was.

“For a living, what job do you do?” she added when he didn’t answer.

“Oh, this and that.” Even though he was sure the question was innocent, he didn’t want to give too much away. He’d found out the hard way that once women knew about his money, that’s all they saw. The fact that he had a lot of money didn’t define who he was. For once, it would be nice to have a woman like him for him.

“Must be satisfying,” she said with a giggle.

“More than you know.” He found himself smiling like a weirdo that, well, couldn’t stop smiling, at nothing. “I get to meet new people, some of them very interesting.” He wasn’t on the lookout for a woman, he was there for business. An undercover mission of sorts for his ever-growing software company. This woman though had something about her that he found intriguing.

She grinned back at him. “So do I, funnily enough. Get to meet people, I mean, some of them very interesting.”

His cock twitched in his pants at the veiled come-on. “It looks pretty quiet in here. Why don’t you sit, Chelsea,” he said, reading off her nametag, “and share a cup of coffee with me. I’m paying and I hear the coffee comes with a free donut. My name’s Josh, by the way.”

“Hi, Josh. Nice to meet you.” Chelsea didn’t sit, but she did glance longingly at the chair if only for a split second.

She wanted to; he could feel it. “Coffee?” he pressed, hoping she’d give in.

“Maybe, I guess.”

He could see her looking around, he guessed to assess how busy they were. She refilled a customer’s coffee and fixed another’s check. His heart leapt when she poured herself a cup and came back to the table and sat down. “You forgot your donut.” He wanted to roll his eyes at his own stupid comment, but she didn’t seem to mind; she giggled.

“Delicious as they are, I get kind of sick of looking at donuts all day; besides, I already had one for breakfast.”

“Which leads me to the next question. What do you do, besides this, I mean? Do you go to school? Is this a family business?”

“Ah, no.”

He saw a slight twitch of annoyance flicker across her face. “To which question?”

“Both. It’s not like this is a real job.” She blatantly rolled her eyes. “I’m certainly not related to the owner of this place and I’m glad.”

“I’m sorry. I didn’t mean to insult you.” He’d hit a nerve and he could have kicked himself. He was just trying to get to know her, not hurt her feelings or anything. “So how about you tell me all about your charming town. What is there to do around here?” The smile was back, as was the sparkle in her eyes.

“Well, let’s see. There’s the bowling alley and there was a drive-in, but that’s closed now. There’s a movie theater, but don’t expect Brad Pitt and Angelina Jolie to drop by for a première anytime soon. Movies screen a few months after they do in the city.”

“I’ll keep that in mind.” Good, the awkward moment was gone.

“We do have a Walmart about half an hour away if you need anything. There is a general store, but that doesn’t have much more than the basics and it’s expensive.”

“Ok, thanks. I’ll keep that in mind.”

“Chelsea!” the only other customer left called. “Heat my coffee up for me, please, honey.”

“Be right there, Fred,” she called back. “Fred is lonely. His wife died last year, he can sit in here all day on one cup of coffee and its refills.” she whispered.

“I might be a widow, young Chelsea, but I ain’t deaf,” the man grouched.

“Sorry, Fred. Just being neighborly with Josh here. He’s just passing through.” Chelsea got up and headed over to fetch the coffeepot.

“You be neighborly with your own business, girl, don’t be spreading tales about me.”

“Will do, sorry, Fred.” She rolled her eyes and mouthed, “He’s a little grumpy.”

Josh didn’t have an answer, which in itself was odd. Usually he had an answer to everything. At that moment he didn’t want to say anything, he wanted to listen, to anything she had to say. Of course watching her wasn’t bad either; there was something about that short uniform and the way she swung her hips. He didn’t think she was even trying to be sexy, but she sure was, sexy as hell.

He watched the pretty young thing as she bent over the older man and poured coffee in his cup. Fred smiled up at her when she touched his shoulder. There was nothing in it, just a sweet person caring about another person, one who was lonely and in need of a kind word and a gentle touch. By the time she left the table, the old grump seemed happy to go back to his paper.

To Josh’s disappointment, Chelsea didn’t come straight back to his table, but continued her work for a little while. She put on fresh coffee and then went in back to the kitchen to talk to the cook. He found himself waiting for the door from the kitchen to swing open again. When the little redhead did appear, she had a fresh tray of donuts. She refilled the plate with the quaint glass cover on the counter. His eyes were still on her and she obviously felt them because she turned.

“You need something, Josh?”

How did he answer that? His jeans were tightening over his growing erection at the thought of what he really wanted and her smile was melting him. “I was wondering if I could have another donut, please.”

She grinned. “You haven’t touched the first one yet.”

Good one, genius. Why would he say that? The blood had obviously drained from his brain to other places. “I know, I was suddenly hungry though and I knew that one wasn’t going to be enough.”

“Ok, then,” she grinned.

He devoured the donut in front of him in a couple of bites while he waited for her to reappear. When she did, she brought the coffeepot and freshened up both their coffees.

“I can take another small break if you’re not sick of me yet.”

“Sick of you? Quite the contrary. I was hoping you’d come back.” He grinned. “I have a confession. I didn’t want another donut, I was trying to find an excuse to get you over here.”

“I figured. That’s why I didn’t bring you one.”

“So tell me about yourself.”

“Me? Not a lot to tell, really. I’m just your average girl from a small town. I’ve lived here my whole life. I started a degree in marketing but it wasn’t really for me, so here I am, working here.”

“It’s an honest living.”

“Yeah, I guess. What about you?”

“I didn’t finish school either. I started a degree in software engineering, but I left before I got my degree.” It was on the tip of his tongue to just blab out everything, but he pulled himself up. He had a good feeling about this girl, but he didn’t know her. Yet.


“I got a job placement and I didn’t really feel like a degree would add to that.”

“Like me. Our stories are similar.”

“Yes, they are, more than you would think.” Josh might be a billionaire now, but he hadn’t started that way. He could relate to someone taking a job in a diner to make ends meet. “I grew up in a country town too.”

“You did?”

“Uh huh. Spent my younger days working on a farm. It wasn’t our family’s farm, but I worked at a neighbor’s farm all through high school.”

“You didn’t like it?”

“Why do you ask that?” He’d actually loved it when he was young, but things change. Computers had always been a draw card for him.

“Well, you said you live in the city, I’m guessing that you didn’t like small town life.”

“I wouldn’t say that. I mean I like the city and that’s where my job is, but there’s something about small town values that are appealing.” And the slower pace. People didn’t spend all day in a diner at home. Well, he didn’t, that’s for sure, and he was too busy to notice if anyone else did.

“You’re right, there’s a lot to be said about it. A happy medium would probably be the answer.”

She’d hit the nail on the head. There were things about living in both places that had merit.

The diner got busier and Josh was disappointed when Chelsea went back to work, although now and then she stopped by his table to see if he needed anything. Another waitress clocked in for the busy period, but her two-sizes-too-small uniform held no interest for Josh, nor did her glossy, pouty-lipped smile. Chelsea was more natural. Although she wore some makeup, which he noticed as she passed for the umpteenth time, it made her look pretty, not tacky or overdone.

It was interesting watching people as they walked by the windows before entering. Some were chattering among themselves and some were alone. One person seemed to be talking to herself, but when she came in, he could see the woman had been talking to a child. Not that there was an influx of people; it was more like a dribble over several hours. Fred finally got up, plonked his hat back on his head, and left, thanking Chelsea on his way out.

As the afternoon became early evening, the daylight outside the lace-framed windows dimmed and soon his only focus was inside the room. It was getting a bit embarrassing. He’d been there all day and all he’d ordered was the coffee and a Coke later in the afternoon. Josh held up his hand to try to get Chelsea’s attention, but dropped it again as the wrong waitress turned around. She smiled and rolled her eyes condescendingly.

“I think your guy—”

“He’s not my guy, Soph—” Chelsea whispered.

Josh tried to look away but just couldn’t. Chelsea had whispered something to the other waitress and he wished he was fluent in lip-reading. All he’d really got was my guy. Were they talking about her boyfriend?

“He wants—. You wanna take first dinner break—?” Sophie snapped her gum noisily.

“Tom wouldn’t like that.”

Ok, he heard that. Who was Tom? The boyfriend they’d mentioned? What did he want? Someone seemed to be planning a dinner break. Was he coming to the diner?”

“—can do whatever the hell they want,” Soph giggled. “Besides, he might not be back until tomorrow.”

Really, could they at least stand still? Every time they turned to do something, he lost part of the conversation.

“What if—”

“—but if it’ll ease your mind some I’ll make sure.”

“How are you going to do that? You know how vague our boss Tom can be.”

Josh only caught a word here and there of that conversation as they were still carrying on with their work, but he did catch the bit about Tom being the boss. The relief that statement brought surprised him. He pricked his ears up when the conversation moved close enough for him to hear what they were saying.

“Watch the master.”

Josh watched Chelsea chew on her pencil. She looked nervous. They’d gone outside to make their call, but were obviously unaware that he could hear them through the thin window glass.

“Hi. Mr. Blackburn?” the other girl said into the phone. “This is Sophie. I’m just phoning because, well,” she covered the phone for a second and giggled silently.

Chelsea covered her mouth, but her body was shaking with silent laughter.

“Chelsea was worried about you when you didn’t turn up to work tonight. She thought you may have had an accident or something on your drive back.”

Josh almost laughed aloud himself as Chelsea made a cutting motion across her throat to her friend. Her delicious curves still shook with laughter beneath her uniform and her eyes sparkled with fun.

“Oh, really? You’re not? I’ll let her know that you’re fine and that she’ll see you tomorrow.” She hung up and both girls burst into a fit of the giggles.

“You’re so dead,” Chelsea said when she finally calmed down. “The sleaze is gonna be all over me now.”

All over her? That wiped the smile from his face. Josh had never set eyes on this guy but he hated him already.

“Oh, don’t be a baby. You can handle him; he likes you, that’s all. Now you know you’re safe, you can go relax with your new friend. I have this. It’ll make up a bit for throwing you under the bus.”

“You are such a friend. I will take you up on it though.”

“If you don’t, I will. That man is smokin’ hot!”

Josh was more interested in Chelsea’s reaction to the other girl’s statement.

“He’s not bad.” Chelsea said with a restrained smile.

She turned and looked right at him and he quickly buried his head in the paper to cover the fact he’d been eavesdropping. Damn.

“Oh, yeah! There’s a lot of good-looking men around here that number one, aren’t already taken and number two, seem taken with you,” Sophie said, her voice laced heavily with sarcasm.

“Yeah, yeah, I know, but I’ve told you before, I’m not looking. It is nice to talk to someone new though, someone halfway decent.”

That was something, he supposed.

* * *

“Hey.” Josh said when the pretty redhead once again stood at his table with her trusty pad and pencil in hand.

“A little bird told me you were trying to get my attention. Can I get you something?”

“As a matter of fact, I am about ready for dinner. Care to join me?” He liked a challenge, didn’t he? Her smile told him she was open to having dinner with him; that was a start.

“I’d like that. It’s about time for my dinner break anyway. What’ll you have?”

“Whatever you’re having, make it two.” He didn’t care what he ate. He just wanted her to go get it, come back to the table, and sit down with him before someone else needed her attention.

“The steak sandwich is good.”

“Sounds good to me. With fries?”

“Of course. What good is a steak sandwich without fries and onion rings?”

“Oh, of course.” Josh could only imagine the size of the plate that was going to hold all that. After years in the city, he’d come to accept smaller portions that cost twice as much money as the norm. It was more like art on a plate than a filling meal. He’d struggled at first, but he’d become acclimated and needed less food after a while. Besides, that’s why God made pizza, so you didn’t actually die of starvation after going to a restaurant.

After a relatively short time, Chelsea was back and as he’d guessed, she set a plate in front of him that could feed a small family. A large steak sub with sides of fries and onion rings crowded an enormous plate. The only thing green was the pickle that held pride of place in the center. “This looks good.” He meant that. Many a night he’d shaken his head at paying an enormous price for a meal, only have to go home and make himself something or order in. No sandwiches were going to be needed after this; he may not ever need to eat again. The thing that really surprised him was that Chelsea set her own identical plate opposite him.

She sat down and took an enormous bite of her sandwich, poking a fry in her mouth for good measure. “Sorry,” she said after she swallowed. “I’m starving.”

She must have noticed him staring. He didn’t come across as rude. It didn’t bother him; on the contrary, it was refreshing to see a woman who wasn’t afraid to eat. There was nothing worse than watching a too-thin woman push a lettuce leaf around her plate. Food, like all of life’s passions, should bring on warm feelings. Sometimes comforting, other times exciting. “No, don’t apologize, I love to see a woman enjoy her food.”

“Well, good, but I’d enjoy it a lot more if you weren’t staring at me, so eat your own dinner.”

Josh thought the food was delicious. He couldn’t remember the last time he’d so enjoyed eating dinner with a beautiful companion. Of course it wasn’t a date, just two strangers sharing a meal; interestingly, it didn’t feel that way. It was fun and more than that, it was comfortable. Even though they’d only just met, Josh felt like he’d known Chelsea forever.

“You and your friend were having fun outside before.” He had been more than a little curious at the phone call and then the laughing.

“Soph was just suggesting I have the first dinner break.”

“Uh huh. It seemed a little more than that to me. It looked like you were being naughty.” Once again his pants tightened, this time at the thought of what he’d like to do to this naughty girl. “You weren’t prank calling anyone, I hope.” Oh, shit, had he just said that out loud? The fantasy of her draped over his lap for a sound spanking had rattled his brain and his common sense. He was sure to scare her off with talk like that.

I wasn’t,” she answered without skipping a beat. “If anyone was being naughty, it was Soph.”

“Really?” Soph could be naughty ‘til the cows came home and it wouldn’t bother him at all.

“No, not really, I was joking. If you have to know, she was calling our boss to see when he’d be back.”

“When will he be back?” He knew he wasn’t coming back until the next day, but he could hardly admit that he’d been listening in on their conversation.

“She was seeing if it was safe for me to take a long break and eat with you without getting caught.”

“Well, then, it looks like I owe Soph a big thank you.”

“So, can I interest you in some dessert?”

“Sure.” He wasn’t sure he could fit it in, but if it meant he could stay a bit longer he’d squeeze it in somehow.

“Sundae or pie?”

“Sundae.” Would it be too forward to ask her to bring one sundae and two spoons? Probably.


“Surprise me.”

* * *

Their spoons were scraping the bottom of the old-fashioned sundae glasses and Josh looked up, realizing the place was empty, except for Sophie who was stacking chairs on tables. He felt a bit like Cinderfella; it was five minutes to midnight and the party was nearly over. Actually it was five minutes to ten, but that didn’t have the same ring to it. All he knew was that he didn’t want it over, not yet, but everything in town would be closed.

“It’s about that time.” Chelsea said, somewhat reluctantly. “I’m going to have to help Soph clean and then we’ll close. It was nice to meet you.”

Hoping to spend a little more time with Chelsea, Josh decided to take a gamble. “I was wondering if you’d like to go somewhere with me when you get off work? We could go for a drive and talk, or you could come back to my room and I could make you coffee?” He watched a wall go up and her eyes lost their sparkle. The gamble had backfired, apparently.

“Thank you, but it’s late and I have to work tomorrow.”

He’d obviously said the wrong thing. Her tone had changed from friendly and open to clipped. “Ok, I wouldn’t want to keep you up if you’re tired.” He hid his disappointment as best he could and stood to leave. “You sure?” No harm in trying one more time, was there?

“I’m sure.”

He nodded and stood up. He pulled more than enough money out of his wallet to cover everything he’d had that day as well as the cost of her dinner and set it down under the napkin holder. “I enjoyed today.”

* * *

Chelsea watched him walk out the door; her heart was heavy. It had been one of the best days she could remember and then he had to go and ruin it. She had allowed herself to actually believe he was enjoying her company as she had his. It would have been different if he’d asked her out on an actual date, but the only place he’d wanted to take her was back to his room. She was a fool for thinking that anyone as good-looking and well-spoken as Josh would be interested in her! He had to have been just after a one-night stand. A bit of fun to fill in time while he was on his way back to his proper life. He probably had conquests in every small town across the country. Well, she wouldn’t be another notch on his bedpost.

“Hey, sis.”

Chelsea shook herself out of her self-indulgent trance at the sound of her brother’s voice. “Hi, Andy. Sorry, I was miles away.”

“What was Josh Wheeler doing in here?”

“Josh who?” How would Andy know Josh’s last name and how did he recognize him on sight?


“The guy who just left?” Maybe he wasn’t talking about the same person.

“Don’t you know who he is?”

Chelsea was stunned by her brother’s incredulous tone of voice. Josh was obviously someone important by the look on Andy’s face, but she didn’t have a clue who the handsome stranger might be. “No. No idea, but obviously you do.”

“He’s just one of the richest men in this country!”

“Sure he is. What would one of the richest men in the country be doing in here?” Surely if he was someone important, he could find somewhere more special to eat than this place. Unless he was looking for a quick and easy conquest, which confirmed her earlier thoughts on why he would ask her back to his room.

Andy shrugged. “No idea, but it was definitely him. I was reading an article about him for school the other day in a magazine. It had his picture and I’m telling you it was definitely him.”


“Honest.” The young man crossed his chest sincerely. “Why would I lie?”

“I don’t know, for some kind of dumb prank.”

“Well, maybe, but I’m not playing a prank, I swear. Wouldn’t it be a giant coincidence if the man in the magazine was a mirror image of a stranger that just so happened to share the same name?”

“Ok, I guess I believe you. Actually he just asked me to go out.”

“He did? What did you say?”

“Um, I said no, of course.”

“Why would you say no? When was the last time you went on a date?”

“None of your business. I’m not in the habit of going on dates with people who I barely know. Besides, it was hardly a date that was on offer. He asked me back to his room for coffee.”

“Ok, I’ll rephrase. When was the last time you had coffee with a guy like that?!”

“I didn’t know he was a guy like that, remember? Anyway, it doesn’t matter, he only wanted one thing.” As soon as those words slipped out, she realized it wasn’t the kind of thing you say to your little brother.

“Ew, thanks for sharing that vision, but I was talking about an actual date. You know, dinner, a movie?”

“He didn’t ask me for any of that, I just told you. It’s not going to happen, little brother, you may as well give up now.” Nothing her brother had said had changed her mind. If anything, it confirmed her thoughts on the man. Why would he be interested in her?

* * *

Josh had held the door open for the young man who entered the diner as he was leaving. As the door closed behind him, he stood there trying to figure out what had gone wrong. He didn’t mind admitting to himself that he had been hurt by Chelsea’s reaction. What was it with him and women? There’d been women who were only after his money, but that couldn’t be the case this time, Chelsea didn’t know he had any money. Besides, even though he’d only just met her, she didn’t give off the vibe of being a gold-digger. It must just be him; maybe he’d been wrong thinking they’d had some chemistry. Maybe he was overthinking things, but he couldn’t help it. The whole day swirled around his brain in slow motion and there was nothing he could do to stop it. Like a song he’d heard on the radio and couldn’t get out of his head.

It had been the most confusing day that he could remember. He’d walked into a very ordinary small town diner to people-watch. Well, that and to maybe get a cup of coffee and some marketing information. Instead he’d found much more. The instant attraction Josh had felt for the cute redhead wasn’t just a one-way thing; he’d been sure she felt it too. It had been a long time since he’d felt that pop of pleasure that comes from knowing a moment is perfect. That you don’t want the person you’re with to walk away for even a minute for fear the magic might be lost. Yet it had ended badly. What had he read wrong? What had he said that scared her off? He had no idea. All he knew was that what he was feeling then and now, what his instincts were screaming at him, felt too real. Surely he hadn’t been wrong. He’d have to stay at least another day. Josh Wheeler didn’t get where he was as the owner and CEO of a billion-dollar software marketing company at such a young age by giving up easily.

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