Madison’s Master

Madison glanced up at the clock as she saved the document on her computer. Twenty minutes past five and the office was more or less deserted, with only Angela and Mark standing by his office door and talking in hushed tones. Their office romance was probably the worst kept secret among their co-workers, yet they still maintained the act of being mere business associates.

Pretending not to notice their intimate touches and gestures, she quickly did her daily back-up and dug her purse from her bottom desk drawer as the system shut down. She checked her hair in the small mirror attached to her cubicle wall, brushing a strand of chestnut brown locks back behind one ear before standing up and running a hand over her conservative knee length beige skirt to smooth out the wrinkles. She went over to the coat rack and donned her brown overcoat, pulling her long hair over the collar with a practiced grace before tying the belt around her slender waist. With a quick smile and a wave to the two “secret” lovers, she stepped out into the hall and onto the elevator that would take her down from her fifth floor work place. As she descended to the main lobby, she couldn’t help but imagine Angela and Mark already wrapped up in a passionate kiss and she sighed, wishing she had someone in her life who could make her feel like that.

As she stepped out onto the busy street, she turned right and walked along the crowded sidewalk toward the subway station a half block away, just like she had every other day for the past year since starting at her boring office job at Stanton’s. It was a small brokerage firm and after a year she was still doing the menial but necessary office tasks that no one else wanted to do. While she wasn’t crazy about the mundane work load, she tried to look at it as paying her dues and hoped to someday work her way up to a more challenging and rewarding position.

As she passed by a small bar, she paused. She wasn’t a big drinker, but she suddenly felt the urge to go in and have a quick one; maybe a nice glass of wine. Why not? People often stopped after work for a few drinks and, after all, it was Friday.

With a ‘what the hell’ attitude, she walked up to the heavy wooden door and pulled it open, the smells of cigarette smoke mixed with the heady aroma of stale beer quickly filling her senses as she stepped into the darkened room. She paused inside the door, scanning the room as her eyes adjusted to the dim light. She could see the place wasn’t full, with only a few people sitting or standing by the bar and most of the tables were empty. They were mostly men, and almost all wore the type of clothing that hinted they too were stopping in for a drink after a long day at one of the many offices nearby.

She made her way to a table in a corner and took off her jacket, lying over the back of one of the heavy wooden chairs, then sat down. Her eyes once again wandered around the room, pausing for a brief second on each patron before moving on to the next. She caught herself, realizing with a hint of embarrassment that she was checking out the men. She was so caught up in her people watching that she almost jumped in surprise when a pretty young waitress arrived at her table.

“Hi! What can I bring you?” she asked, her pen poised at a notepad as a friendly smile spread across her pretty face. If she noticed Madison’s surprised start, she didn’t comment or show any indication she had.

Madison gathered herself together and found herself smiling back. “Just a glass of white wine, please,” she said.

The girl scratched her order on her pad and nodded, then went over to another table where one man sat alone. Madison hadn’t noticed him before, and as he chatted with the waitress she found herself somehow drawn to him. He looked to be in his early to mid thirties and had dark, neatly trimmed hair. He wore a black dress shirt with a matching black tie and looked very handsome, with an air of confidence she found very attractive.

Suddenly realizing she was staring, she quickly averted her eyes just as the waitress laughed at something he said and turned away to go fill their orders. She forced herself to avoid looking back in his direction, but only a minute later found her gaze once again moving back to him. Her heart skipped a beat when she saw he was looking back at her, and when he met her eyes, he gave her a warm smile that sent her stomach swirling with a million butterflies. She quickly looked down, fumbling in her purse for the money to pay for her drink. While certainly not an unattractive woman, she was nervous and shy around people she didn’t know and rarely acted upon the occasional flirtatious glance from men, especially men that were as unbelievable sexy as this one!

The waitress arrived with her drink and, thankful for the distraction, she paid her and quickly took a sip from the tall goblet. As she set it down, she glanced over and saw the man accepting his drink and chatting amicably with the waitress. He nodded in her direction and the waitress turned to look, then smiled and nodded before walking off. Catching her look, he raised his glass in a toast and smiled before taking a sip.

Madison swallowed the lump forming in her throat. This sexy, alluring man was flirting with her and while she wanted to flirt back, she was too nervous and scared to do more than offer a wan smile. She plucked a small menu from between the salt and pepper shakers and pretended to read it, trying in vain to get the thought of his alluring eyes watching her out of her mind. But in truth, she wasn’t exactly sure she wanted to do that. It gave her a thrill to think that he was sexually attracted to her, even though she was dressed in her work clothes with her makeup still passable in the dim light, but no longer perfect.

For what felt like a long time, she kept her eyes on the menu, only looking up long enough to pick up her glass for another swallow of the sweet wine. When it was almost empty, the waitress appeared with another one. Madison looked up at her and was about to tell her she hadn’t ordered a refill when the waitress gestured toward the dark-haired man.

“He asked me to bring you another when yours was gone,” she replied to the unasked question as she picked up her empty glass. She leaned in and gave Madison a wink and whispered, “Isn’t he hot? Go for it honey!” With a knowing grin, she left her and Madison felt her face flush at her words. Taking a deep breath, she looked over at the mysterious stranger and nodded her thanks over the rim of the glass as she took a sip. She surprised herself at her cool demeanor and the thankful but dismissive way she’d given him her thanks. In truth, she was terrified he might come over and want to talk, but he simply raised his glass in response and offered a slight bow of his head.

Now she was confused. The normal routine was to buy her a drink, then once acknowledged, come over to talk, using the drink as an excuse for introductions. Yet he sat there reading a newspaper, now seeming oblivious to her presence. Was he expecting her to go to him? Even if she thought she’d have the courage to do that, there was no way she’d ever put herself out to be that needy. Yes, it was true it had been over a year since her last sexual encounter, and it was also true that she now practically considered her vibrator to be her lover, but there was no way she was going to be the one who initiated things. She was an attractive woman of twenty-six, with a figure she knew attracted looks, especially when she dressed in sexy clothes. She just wasn’t ready for a relationship yet after her and Tony’s breakup, and a one night stand was simply not her style. Ok, so it had been ten months since they’d finally admitted it was over, even though for the last two months of their relationship they’d become more or less room mates instead of lovers. But she had been in love with him at one point, and the pain of their breakup was something she didn’t ever want to go through again. Her girlfriends had tried setting her up a few times, but it never amounted to anything beyond a good night kiss or at most a short make-out session. She sighed and stared down at the almost clear liquid in the long stemmed glass. Maybe it was time to start living again.

“Is there something wrong with the wine?”

She was still deep in thought and hadn’t seen him approach her table. She looked up in startled shock, spilling a small amount of wine over the rim and over her hand. She brought her hand to her lips and licked the small droplets from it, looking up into the warmest brown eyes she’d ever seen. The mystery man was standing next to one of the other chairs at her table and she swallowed hard before trying to speak.

“No… no, it’s fine… and thank you… I was just… thinking about something…” Her voice trailed off as their eyes locked and she found she couldn’t look away. Those eyes were so… so intoxicating that she felt like he was looking into her very soul.

He lay a hand on the back of the chair and raised his eyebrows questioningly. “May I?” She was nodding before she even realized it and he sat down, pulling the chair up so that he was looking directly across the table into her eyes. When he spoke, it was like his voice was the only sound in the room, so soft and inviting, but at the same time confident and leaving her with the impression that he was in total control. For some reason, that didn’t scare her, and she couldn’t explain why. He reached out and took her hand, his fingers warm and light on hers. “I’m sorry if I’m intruding,” he began, his eyes once again holding hers, “but when I see a beautiful woman sitting all alone like you are, I just have to know why.” She felt her face flush and he continued. “So tell me, beautiful lady, why do you sit here all alone accepting drinks from strange men?”

“I… I was just having a drink after work, and…”

He stopped her by raising his other hand. “I’m sorry, how rude of me not to introduce myself. My name is Robert,” he said, looking expectantly at her.

“M… Madison,” she stammered, silently cursing herself for acting like a little school girl. She straightened up and in a somewhat firmer voice said, “My name is Madison.”

“Madison.” He spoke her name slowly, as if savoring it. She felt a warmth in her lower region at the sound of her name in his velvety soft voice. Damn, what was this power he seemed to hold over her? They’d only spoken a few words yet she found herself almost completely under his spell, whatever that was. All she knew was that it would be hard to resist anything he asked her to do, and that was terrifying in itself.

He squeezed her hand a little, bringing her thoughts back into focus. “So tell me, Madison…” There was a pregnant pause as his eyes held hers. “… are you… seeing anyone?” She couldn’t look away from those mesmerizing eyes, but shook her head slowly. “That’s good,” he replied, taking a sip of his amber drink before continuing. “I would very much like to get to know you better. Would you like that?” Again, a nod was the only answer she was capable of giving. Along with her free will and powers of reasoning, he also seemed to have taken away her power of speech and she found herself unable to make her vocal cords respond to her commands. He smiled at her and nodded. “Very good.” He glanced at his watch, frowning. “Unfortunately, I have a prior engagement this evening. But, I want you to meet me here tomorrow night at seven o’clock. I will be at the same table. Can I count on that, Madison?” She had the distinct impression that it was more of an order than a request, but once again she felt unable to resist his charming demeanor. Again, she nodded, his eyes holding her almost in a trance.

He stood up and released her hand, then moved around so he was standing behind her, resting his hands on her shoulders. She could feel the heat from his touch through her thin blouse and it sent a shiver of excitement down her spine. He leaned over so that his lips brushed her ear. “I need you to know that if you do decide to come, I will treat you to the most exciting experience of your life. It will seem a little scary at first, but there is nothing to fear. I will not allow any harm to come to you. I can tell that you need a man to control you, and I am that man. If you come tomorrow, I will expect you to do whatever I tell you to with no hesitation or questions, and I will take your presence here tomorrow as your acceptance of these terms. Do you understand?”

She listened to his words, her fear rising but another sensation was quickly over riding it. She recognized it as sexual desire, a feeling she’d long denied herself. But this was much more insistent than any she’d ever felt before. And there was another feeling that was equally exciting – the feeling of being controlled, and it was just as powerful as her desire for him. It was like he was looking into her soul and telling her things about herself even she hadn’t known. She could feel his warm breath on her ear, which only served to increase her excitement.

“Y… yes, I understand,” she whispered breathlessly.

“Good.” She felt him move away and he stood beside her, looking down at her. “I want you to dress more… sexy. Wear a skirt, a mini skirt. Very short. And no bra.” He gestured toward the table he’d been sitting at. “When you arrive, come over and sit down without speaking. I will tell you what to do. Do you understand?”

Her reply was barely audible. “Yes.”

He nodded, his eyes holding hers. “Very good. Until tomorrow, then.” He picked up her hand and kissed it, then without another word, he walked out the door.

Madison sat there for several moments, her heart pounding in her chest. Had that really just happened? She reached out for her drink and noticed her hand was shaking. She took a few deep breaths and waited for her body to calm down, then gulped down the remainder of her wine. Suddenly she needed to get out of here; to go home where everything was safe, calm, and orderly.

She stood up and pulled on her overcoat as she made her way to the door, then stepped out onto the street, breathing in deeply the cool evening air. She took a look down the street both ways, but the mysterious man was nowhere to be seen. The sidewalk was still busy, though not as crowded as earlier. Stuffing her hands into her pockets, she made her way to the subway station, wanting nothing more than to go home and slip into a nice warm bath and try to figure out what had just happened.

Chapter 2

The next day was a blur. Madison told herself that she wouldn’t meet the stranger with the incredible brown eyes and sexy voice, yet here she was, looking through her clothes for a short mini skirt. She brought out a short yellow one and walked over to her bed, holding it up to her waist. It fell almost to her knees, but she had the impression he wanted something even shorter. She dropped it to the bed and picked up a pale blue skirt that was only a little shorter, but was tight enough to hug her hips and legs. It was much shorter than she’d been comfortable in and she’d really only worn it once. But she had to admit she looked great in it.

The other choice was something she’d never worn in public. It was a black leather-like skirt, so short that it barely covered her panties. She also had a matching bra for it. She’d bought it as a birthday surprise for Tony two years ago and the only time she wore it was in the bedroom. He called it her ‘hooker outfit’ and they had a lot of fun role playing her being a hooker who had to do what he wanted her to do. She remembered the thrill when he told her to get on her knees and suck his cock. It felt so bad, so dirty, and yet it thrilled her to be ordered around. As she held it up to her waist, she knew now why she was doing this. She did like being told what to do, and even though she didn’t know this man she was to meet, she felt she could trust him. Maybe that was wrong, but that was also part of the allure. She’d been a good girl for far too long. It was time to let loose.

She pulled off the sweat pants she’d been wearing and slipped into the black skirt. It was so tight she had to suck in her breath to zip it up, but once it was in place, she looked admiringly at herself in the mirror. She really did have a hot body, with long slender legs that looked even longer in the short skirt. She tugged it down a little so that her panties were covered and moved around, making sure nothing was exposed when she walked. It looked ok, but it was really too short to wear in public and she’d be risking exposure every time she moved.

She took a look at the clock by her bed – almost four. Quickly slipping out of the tight skirt, she tossed it onto her bed and slid her panties off, then her t-shirt. She stood naked before the mirror now, her hands moving over her bare skin. Her tits were still nicely rounded and sat high on her chest and as her hands brushed across her pink nipples, she imagined they were his hands and they instantly knotted, growing stiff and sensitive to her light touch. She inhaled a sharp breath, a warm tingle starting between her legs and she could feel the herself becoming moist at the idea of being naked in his presence, waiting to do his every bidding.

Her fingers trailed down over her firm stomach, through the finely trimmed patch of soft, dark brown hair, and sought out her throbbing clit. She began to slowly rub it, dipping a finger into her wet pussy every so often. She imagined his tongue massaging her sensitive clit and it wasn’t long before she was overcome by a strong orgasm, her body tensing and jerking as she watched herself in the mirror.

She finished and felt her knees weaken, but remained standing, her 34C breasts heaving as she came down from her self induced climax. She brought her wet fingers up and studied them for a moment, watching the tiny droplets of her fluids seeping down her long fingers. She brought her fingers to her lips, then sucked each one clean, savoring her own juices. She actually liked the taste, and loved the reactions of her lovers when they saw her doing it. While she’d never been with another woman sexually, she was certainly curious about it and had always suspected that given the right woman and situation, she could be convinced to try lesbian sex.

As the tingling slowly eased in her overheated body, she went into the bathroom and turned on the water, adding a generous amount of bubble bath. A nice warm bath would help her relax and prepare for whatever unknown thrills this night may bring.

Chapter 3

A few hours later she walked along the street toward the bar, her long overcoat hiding the short blue mini skirt she was wearing. She’d almost worn the almost obscenely shorter black one, but at the last moment decided against it. She didn’t want the entire bar thinking she was a hooker, after all. She felt her breasts bouncing with each step under her tight top, a reminder of Robert’s instructions that she go braless. She was thankful for her overcoat, which not only hid the short skirt, but also covered her nipples, which were aroused to full hardness from the constant contact with the material. She tried to put the thought of taking it off in the bar out of her mind, only hoping that the dim lighting and table would hide her suggestive clothing.

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