To Please the Billionaire


Annie peered through the shadows of the most magnificent penthouse she could ever have imagined. This had been her home for the last 3 months and, with barely a warning from her handler Jarvis, she was about to meet her benefactor for the first time.

Annie took time to consider her new position. Jarvis had described the job as being a companion. He described his employer as a wealthy man whose jet-setting didn’t allow for girlfriends. He did, however, enjoy the company of young women. Compensated with a stipend, a salary, and an extravagant place to live, the job required no sex and would last as long as both parties desired. Having called a few of the other girls under her benefactor’s employ, Annie could not dismiss the opportunity.

There was one thing that Annie did want before accepting the offer, however, she wanted to know ‘why her?’ Annie was not a sex symbol. She didn’t consider herself to be as beautiful or elegantly dressed as the other women in the restaurant where they had met. Annie thought of herself as ‘pretty enough’, but hardly a woman deserving of such attention.

Annie considered herself to be a smart girl having worked her way through college, as well as a hard working girl. The idea that she was unique enough to be paid to accompany a wealthy man to dinner, made her feel special in a way that nothing else ever had. It was that flattery that made her take the job. ‘Perhaps I’m being naïve again,’ she thought, ‘but what harm could possibly come from this?’

Annie was ill prepared for the effect that a 5 figure clothing allowance and a gourmet chef would have on her. Dancing and twirling in her new dresses, within the confines of her Victorian styled penthouse, ignited her fantasies. She found it easy to fall in love with a man that allowed her such pleasures, even if she knew nothing about him. Her life had been so hard up until the moment Jarvis approached her in the restaurant that her gratitude quickly transformed into more. Rounding the naked marble cherub guarding the black and white tiled living room, Annie held her breath wishing that her benefactor lived up to her fantasies.

Searching the dark corners of the dimly lit space, Annie found no one. She knew he was here, having heard him enter, but in trying to tame her rapidly beating heart, she had no idea where he could be.

All of her questions were answered when Annie looked in the one place she always avoided. Like no other place she had visited, her penthouse had a large balcony. Twenty five stories in the air, Annie nearly lost her breath when she realized that the balcony only had a waist high railing preventing her fall. Looking out on her first day she recognized how irrational the idea was, yet she couldn’t help but picture a large gust of wind picking her up and tossing her to her death. With nothing more than a low railing to stop her, stepping out to the large penthouse patio could mean her death.

Annie considered that with her luck the man she could so easily love would be standing on the balcony examining the view. She wanted to go to him, but the idea of venturing past the open sliding glass door made her heart ache.

Slowly, approaching the doorway, she gazed out at the man. Seeing only his back she found a sprinkling of grey hair amongst his thick, black mane. Examining the way his silk dress shirt draped over his back, she knew he was in good shape. He looked relaxed as he stood there, so she knew one more thing about him; he was confident. So as long as he wasn’t the ugliest man she had ever seen, she knew that her heart would be his.

Sensing how quickly she could fall for him, Annie quickly turned her attention to herself. She was wearing one of her new dresses, not one of her sexiest. It wasn’t her nature to dress sexy, but suddenly feeling like a child in her cheery sundress, she wondered if she had enough time to change. As he turned around and looked at her, she knew she hadn’t. Annie froze.

“You are Annie,” the rich resonant voice said in a slightly European accent. Annie couldn’t tell where he was from but found the accent seductive. “Please, come to me.”

Annie didn’t know what to do. She wanted to go to him. His rugged features and reflective light eyes drew her to him. The 15 feet she would have to cross to get to him made her weak in the knees. Wanting to step forward as much as she wanted to run back, she remained still. Desperately wanting to please the man who had given her the most wonderful experience of her life, her eyes pooled with tears.

“I’ve watched you,” the man continued. “You never come out onto the balcony. Does it make you afraid?”

‘You watch me?’ She repeated to herself. This brought her out of her struggle. “What do you mean?” Annie continued.

“The furthest you have ever gone has been the spot where you now stand. No further. Why is that?”

“We’re very high up. I’m afraid that there could be a strong wind that could…” she couldn’t finish.

“Tell me, are you afraid a lot?”

‘No,’ Annie thought. This was not the way she wanted her benefactor to think of her. The balcony was an irrational fear and she knew it. She could see that her benefactor’s hair didn’t even move in the breeze. She knew that she would be perfectly safe, yet she didn’t budge. “No I’m not,” she finally declared.

“That’s good, because I have no need for a scared companion.”

‘A companion,’ she thought. ‘Is that what I am? I can do that,’ she reassured herself. “I’m not afraid.”

“Then come to me. Show me how brave you are.”

Annie knew what she had to do. The stakes had just risen beyond her simple employment or this stranger’s love. It was about her. Would she allow her fear to limit the potential of her life? She would not. Focused as acutely as she could, Annie made her legs move. Feeling for the first time the rough stone under her bare feet, she felt a rush of excitement.

Annie’s mind floated as she crossed the patio. Keeping her gaze firmly on the man’s eyes, she found him comfortably staring back. He had a pleased look on his face and the merest hint of his approval made Annie’s body tingle.

Stopping in front of the tall man, she looked up at him. He was fit looking and smelled of citrus and the sea. He smelled good enough to eat.

“Good,” he said with a closed lip smile. “Now look out.”

The man moved out of the way revealing the illuminated nighttime city skyline. Not having looked in this direction before, Annie found it breathtaking. She had no idea how beautiful the city could be. Facing the harbor, the bridges that crossed it were lit as if lined with thousands of twinkling Christmas lights. It was awe inspiring.

“Step forward,” he commanded.  Annie quickly obeyed.

Annie stepped towards the edge and leaned over to grab onto the railing. Breathing in the sights and the cool night air, she realized how foolish her fear had been. She was safe. If it wasn’t for her benefactor, she might not have experienced this either.

“Isn’t it beautiful?” His rich voice reverberated.

“Yes. I don’t think I’ve seen anything so wonderful.”

While Annie continued to stare at the city, she felt the man’s warm hand touch her leg. As he began to explore her body from behind her, she didn’t know what to do. Standing still as she was in the doorway, she followed his touch as it separated into 5 fingertips to further massage her between her legs.

Annie’s face became flushed as he explored her body. No man had touched her there since her awkward 16-year-old boyfriend had accidently taken her virginity. She hadn’t meant to have sex with him, but in the confusion of fingers and touches, she had lost her innocence, regretting the moment ever since.

This man’s touch wasn’t like the 16-year-old’s, though. He seemed to know what he was doing. It was like he was strumming a cord that led deep into her nether region. Every time he plucked it, she fell further under his spell.

As the man’s large hands touched the delicate cotton of her panties, Annie could barely breathe. Fighting for breath words tumbled out of her mouth. “I was told that sex wouldn’t be required.”

“Sex isn’t required,” he casually replied. “You may go if you’d like.”

Allowing her to leave with his words, his hands were another story. His fingers, with their gentle exploration, demanded her to stay. Before she knew it, her pelvis was rocking under his touch like a building swaying in the wind. As his fingers found her engorged clit, Annie gave in.

Annie swallowed as her head rocked from side to side. Feeling her mind float away she lost herself in the undulations of his rubbing. Her panties were becoming wet and she knew it. She didn’t know what would be unleashed if she let herself go in his hands. Unable to move, she knew she had no choice but to find out.

Annie’s teeth chattered as a powerful feeling worked its way into her loins. As a rule, she never touched herself but now, possessed with lust, she felt unprepared. She wanted to scream but couldn’t. She wanted to fall to the ground but couldn’t. All she could do was quiver and shake as the pleasure overwhelmed her. As if in a waking dream, she was overcome by a tidal wave of emotions that painted images under her eyelids in shimmering shades of red and pink. She had never felt so alive, and when her loins pulsed, every muscle in her body clamped and released in ecstasy.

Showing mercy, the man’s movements stopped. Annie’s mind relaxed. As her explosion ebbed, her swollen lips became almost too sensitive to touch. Now exhausted, the deep crevice between his large fingers cradled her clit comfortably. She never wanted him to move. She never wanted to be away from him. She was his to do with whatever he wanted. She thought that because she didn’t know what he had in mind.

Without the same reverence for the moment that Annie had, the man let go of her wet pussy and headed back toward the living room.

“Well done. I will be back.”

Not sure of what to do, Annie did not move. She wasn’t sure if she could move if she tried. Drunk on the mixture of excitement and orgasmic pleasure, she swayed in the breeze. Not feeling his return, Annie opened her eyes and stared at the cityscape again. It was beautiful and now the night lights seemed to glow even more.

In the back of her mind, she knew that her sheltered life experiences hadn’t prepared her to resist the will of such an alluring man. Awash in the pleasures of the night, she didn’t think it mattered. All that did matter to her at that moment was experiencing pleasure like it again. The thought that she might not, was too much to bear.


Four months earlier Annie couldn’t have imagined anything like this. She was never the girl that the boys chased after and gaining her lone boyfriend at the age of sixteen seemed more like a fluke. After their accidental sexual encounter, Annie immediately broke up with him and threw herself fully into her school work.

After she graduated from high school, Annie was aware that her single mom wouldn’t be able to pay for her to go to college, so she got a job and worked her way through. Graduating in four years, while working 40 hours a week, Annie increased her hours to 60 hours a week to pay for her little brother’s tuition as he attended a school that was even more expensive than her own.

This didn’t leave Annie much time for a social life. She woke up, went to work and came home to sleep. She didn’t seem to mind it at the time. It wasn’t until her little brother graduated that she began to look around and understood what she had given up. At the age of 25 she had no friends and no social skills. With no reason to continue to put herself through her work-a-day hell, she found that she had no purpose in life.

It was in the bittersweet celebration of her financial freedom that Annie indulged in the first true luxury of her life. Freed from the burden of tuition, she dressed up and found the most expensive restaurant in town. It was while she was sitting by herself that Jarvis approached her.

Jarvis was a distinguished looking older gentleman. Annie found him to have a calm, trustworthy demeanor. He appeared like a professional and his grey hair made her feel comfortable in his presence.

“Are you dining alone?” Jarvis asked in an elegant tone.

“Oh,” she yelped surprised that someone like him would talk to her. “Yes, I’m alone today,” she said with a blush expecting him to join her as if it was a bar instead of an upscale restaurant.

“I hope you don’t mind me asking, but are you a model?”

“A model? God no,” Annie replied flattered that he would even pretend it was possible.

Jarvis looked at her surprised at her response. “Certainly you have been asked that before?”

“Thank you, but no. I’m afraid that’s a first.”

Jarvis continued to look at her curiously. “May I sit down?”

Annie, considering this night one of the greatest adventures of her life, decided his presence would make her evening even more exciting. “Sure,” she said with a blush.

“You seem like a very charming young lady.”

“You too,” she offered opening her mind to dating an older man.

“That’s very kind. I represent a very wealthy man.”

“Yes,” she acknowledged, confused as to where the conversation was leading.

“He often travels and, as busy as he is, he enjoys the company of lovely young women like you. Before you think otherwise, I would like to point out that I am not referring to sex. My employer is simply a generous man that doesn’t want to eat dinner alone when he’s in town.”

Annie looked at Jarvis with trepidation. “I’m sorry, I don’t know who you think I am but I’m not that type of girl.”

“Please, don’t be offended. What I think you are is a woman who in spite of your beauty, chooses to eat dinner alone. My employer is an interesting, successful gentleman that chooses not to eat dinner alone. It would seem that you two might have something in common.

Please, don’t be mistaken. You wouldn’t be the only charming young lady that he has such an arrangement with.”

“What do you mean?”

“My employer has three other young women in town under his employ. If you would like, I can give you their numbers and you can talk to them to see what their experiences have been. And of course, you would be well compensated for your time.”

Annie wasn’t easily persuaded by money, but the idea that someone would pay her to have dinner with them after she struggled for so long just to survive, intrigued her. It made her feel special, like Jacqueline Kennedy or Princess Diana.

“How would I be compensated?”

“You would receive a penthouse apartment to live in, a generous monthly salary, and a more than adequate weekly stipend where you would be expected to expand your wardrobe for dinners with your employer.”

“And all of this is without having sex with him? My mother said that when something is too good to be true, it usually is.”

“And those are wise words, so if you don’t mind, I will give you my card and the numbers of the three other young ladies. I encourage you to call them and consider the offer. You seem like a level-headed young lady. I’m sure that you will come up with a decision that is right for you. I personally hope, for your own sake, that you accept this. What my employer is offering you is a once-in-a-lifetime opportunity. I think that my employer would really like you. I hope that you will consider the position.”

Jarvis took a card out of his pocket and handed it to Annie. Annie looked at it as he got up.

“And, as a thank you for giving me your time, I will, of course, pay for your dinner.”

Annie blushed. “No, you really don’t have to.”

“Please, I insist. Have a good night.”

And with that Jarvis was gone.

Annie sat staring at the card. She didn’t know what to think of what had just happened. When her waiter informed her that not only was her meal paid for, but a driver had been provided to her for a ride home, she giggled at what other possibilities could follow.

Not owning a car, Annie accepted the limousine ride back home. The next morning she called each of the numbers on the back of Jarvis’ card. All of the girls sounded blond and pretty; in other words, they didn’t sound very smart. In spite of all of her hours of work, Annie had managed to graduate from business school at the top of her class. It was only because she needed to find a job quickly to pay for her brother’s tuition that she ended up as a clerk in a pet shop.

“Would this rich man still want me to be his paid dinner date if he knew that I wasn’t a pretty airhead?” She asked herself. ‘Probably not,’ she decided.

One thing that Annie did find unusual after she questioned all of the girls, was that none of the girls had ever met him. One had been under his employ for six months collecting a paycheck and stipend, living in a penthouse and never once going out with him. If she did work for this eccentric man, Annie thought, how long could she collect a check before he discovered that she was intelligent? How much of a nest egg would she be able to put away in order to allow her time to find a real job once the job that Jarvis offered her ended?

“I have to take this,” she finally realized. “I can’t pass this up.”

Annie found Jarvis to be both surprised and excited when she called him. She couldn’t be sure why. When she was given the key to her penthouse apartment and shown around, she couldn’t believe what she saw. It was like nowhere she had ever been. She wasn’t even aware that such luxury existed in real life. She felt like an imposter walking around the expensive furnishings on the first night. After three months of prepared meals and time to unwind, Annie simply felt like the luckiest princess in the world.


Annie’s first meeting with her benefactor hadn’t quite gone as expected. He looked like a handsome prince, but there was more to him than that. He was assertive and demanding. Annie didn’t think that he was dangerous, but he was more unabashedly masculine than she could have imagined. He had a strength to him that made her want to follow him. Even in their brief meeting, she could feel herself succumbing to him.

Annie could barely sleep the night after she met her prince. She thought continuously about how he had touched her and made her feel more like a woman than she ever had before. She wondered if he really would come back and how he knew that she never went out onto the balcony.

‘Did Jarvis tell him?’ She wondered. ‘If so, how did he know? Am I being watched?’

Although she hadn’t contacted them since that first call, Annie thought about her fellow companions. ‘Has he visited them as well?’ She wondered. ‘Would they tell her if he had? Had they experienced the same thing she shared with him.  Would they share with her if he did the same to them?’

As soon as the sun came up, Annie decided that she had to find out. Sluggish from a sleepless night, Annie waited until 9am to make the first call. From her own lifestyle Annie knew that 9am would be early for them. Justifying it by considering it a warning call, in case she was the first one that their benefactor had visited, she grabbed the card and dialed.

Annie’s first call was to Candy, the de-facto leader of the group. Candy was employed the longest and, from her previous calls, Annie knew that all of the other girls seemed to defer to her experience.

“Did he visit you too?” Candy responded before Annie could say a word.

“He did,” Annie offered hesitantly.

“I’m so sorry,” Candy offered.

Annie was confused. Was his sexual touch a bad thing? Had he done worse things to the other girls? Was what Annie experienced the first of many awful things to come? “Why, what did he do to the other girls?” Annie asked.

“He fired them. Isn’t that what he did to you?”


“What did he do?”

“He touched me.”

“How so?”

“You know, between my legs?”

“Did you have sex with him?”

“No!” Annie protested.

“Huh. Well it looks like all of the girls are being fired. But he hasn’t fingered any of the others. Maybe he’s not gonna fire you.”

Annie didn’t know what to think. Was her job at stake? Had he promised to return so he could fire her too? Did she even want this job anymore? ‘Yes,’ she decided. She did.

“What do I have to do to keep my job?” Annie asked Candy searching for a way back into her benefactor’s good graces.

“Well, give him whatever he wants.”

‘Give him whatever he wants?’ Annie thought. ‘I can’t do that. No money is worth that. I’ve lived without his money before I met him and this job was never supposed to be forever. Besides, I was promised that sex wasn’t required. I’m not that type of girl.’

Annie concluded the conversation quickly. Candy was a nice girl, Annie thought. ‘She has a good heart, but she clearly has a lot fewer options than I do. That is why I sacrificed so much for my degree, so I wouldn’t have to do a job like this. I don’t need him if that’s what it takes. Maybe if sex wasn’t required, but not otherwise.’

Wandering around the penthouse, Annie was slow to get dressed for the day. She wasn’t sure what she should wear. From what Candy had said, Annie was expecting her employer to return. She couldn’t decide if she should dress like a woman who would be fired or like a woman who was fighting for her job. She knew that fighting for it meant she would need to wear something sexy.

‘Why am I even considering this?’ she asked herself. ‘Maybe if I wore something sexy, I wouldn’t be doing it for him. Maybe I would be doing it for me. Maybe I want to show him what he would be missing. Besides, I bought a lot of clothes in the last 3 months, and I bought them to wear for him. When will I ever get the chance to wear them again?’

Annie was convinced. She would wear her sexiest outfit. It would be the red silk one that draped over her revealing every curve. Thinking ahead, Annie decided that as soon as she sensed that she was about to be fired, she would quit. Then, like a movie star, she would simply glide out of the room. That would be the way to make an exit.

Annie packed up all of her belongings in anticipation of whatever would happen tonight, even though everything she needed from this experience was already in her bank account. If, by some small chance, he didn’t fire her, she might then show her appreciation. How she would, she wasn’t sure.

Annie sat anxiously awaiting her employer’s return. She found it hard to remain indignant the entire time. For the first few hours she sat like a queen awaiting her execution. The next hours after that she waited like a politician about to address her constituency. In the end she found herself waiting like a girl who waited for a guy whom she feared might dump her. Indignation just wasn’t in her repertoire. She was a girl at heart, and like every girl, she just wanted to be loved.

Finally, when Annie heard a knock on the door, she knew it wasn’t her benefactor. In the time it took for her to get to the door, Annie was sure that her visitor could only be one person, Jarvis. Was her former prince going to deny her even this, his final presence? She wondered.

“Miss Annie, my employer will be here in twenty minutes and I must prepare. May I come in?”

“Sure,” she said with a heavy heart. “Come in,”

Jarvis turned around and signaled. Stepping in he was followed by a handful of waiters and a chef. The group immediately headed to the kitchen and went to work. Jarvis circled the space looking for anything that might be out of place. With Annie, nothing ever was though. It was something that was first mentioned to him by the housekeepers. When the penthouse passed his inspection, it was time for Annie.

Jarvis cornered Annie in her bedroom and examined her from head to foot. Annie felt self-conscious during the virtual undressing. Squirming as she stood, she found she couldn’t stop herself from speaking.

“Do I look okay?” She asked fighting every urge to cross her arms over her C-cup cleavage.

“Miss Annie, you look divine.”

Annie smiled. She knew that this was going to be the nicest firing that she ever had. Candy had given her no indication of this. Feeling grateful for all of the assistance he had given her, she relaxed allowing a lingering question to surface.


“Yes, Miss Annie?”

“Why did you choose me?”

“What do you mean?” He asked returning from his bathroom inspection.

“When you saw me in the restaurant, why did you choose me?”

Jarvis stopped in front of her searching her face for clarification before continuing. “I didn’t choose you.”

It was now Annie’s turn to ask. “What do you mean?”

“My employer did.”

Annie was confused. “Was he there?”

“He was aware of who was at the restaurant that night.”

“Oh,” Annie paused before continuing. “Then, do you know why he chose me?”

Jarvis smiled. “Perhaps that is something that you should ask him.”

“Jarvis, is he coming here to fire me?” Annie asked, no longer able to hold it back.

Jarvis looked blankly. “I am only here to prepare. I do not presume to predict his actions.”

Annie got an odd sense of joy from this. ‘Perhaps my fate isn’t set in stone,’ she thought. ‘Maybe I can convince him to keep me. But, no sex. If I continue to work for him, there can’t be any sex.’