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 s*x 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 s*x 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 s*x 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 s*x wouldn’t be required.”
“s*x 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 c**t, 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 c**t 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 p***y 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 s****l 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.