Chapter 05
Richard's Dirty Little Secret
To the outside world, Richard Thompson was the picture of success. Many people envied him; many people wanted his life. He was a partner in one of the larger law firms in town. He had a beautiful wife who was devoted to him, and committed to raising their children, full-time. His two children were earning top marks in university. His son was even following in his footsteps and studying to become a lawyer, with the intention of one-day joining the firm. His house was an older house that had been his parent's home that he had renovated after their untimely death. Yep, to most people, Richard Thompson was the kind of guy that other guys looked up to.
What people didn't see were, the long hours at the office researching cases, and the countless family functions and dinners that he had missed over the years. He felt like a stranger in his own house and didn't know his kids as well as he would have liked. Even his wife felt more like a roommate than a boon companion. He didn't blame anyone but himself for the hollow shell of his family life, he knew that his career success had come at a price of his home-life. There were times when he wondered if it was worth it, if the trade-off had been a good one. What good were money and prestige when the people you worked so hard for, didn't love you as much as they could?
The hollow shell of his life was not the most guarded part of his Richard's life. Anyone who looked closely at his life could guess what his home-life was like. The part of his life that he kept locked away from the world came up suddenly, ten years ago. It was then that his life took an odd turn that he was ashamed of, yet couldn't live without. What Richard would be mortified if anyone ever found out, was that for the past ten years, he had a Mistress. The Mistress that Richard had was not the typical Mistress; she was not a girlfriend he kept on the side. No, the Mistress that Richard had was the kind that he served, the kind that made him grovel, beg, please her, and beat him when he was wrong. Yes Richard Thompson was a Slave to a Dominatrix. He didn't serve her on a permanent basis, but for an evening at a time. They had a regular schedule to their meetings but the occasional time she would call and demand to see him immediately. Every time she called, unless he was in court, he would drop everything and rush to see her.
All that ended two weeks ago, and since it ended he felt lost and confused. He had become so used to their regular get-togethers, along with the degradation and servitude, that he was having trouble going back to the "vanilla lifestyle." Something about the way he was treated by her almost seemed like penance for his monumental success. It was a strange and twisted way of keeping him grounded. He went through the routine of his life these past two weeks but life itself had lost its flavor, he was depressed.
Sex with his wife, Taryn had lost all interest for him because she liked it plain and ordinary, but he had developed a flair for the kinky. Richard needed the extra kick of being dominated and humiliated by a woman to really get off. While part of him wanted to go out and find another Mistress, the risk of being exposed, always kept him from doing so. A small part of him even thought of confiding in Taryn, to see if she would be willing to give him what he needed. The shocked and outraged reaction as well as the hurtful argument that he imagined always kept his mouth shut. Richard knew that this strange limbo couldn't last for long; sooner or later his needs would push him to seek satisfaction somewhere.
As Richard sat in his office at the law firm downtown, his thoughts drifted to his beloved Mistress. He sighed as he valiantly tried to stop his memories from forcing him to think of her. Unwanted and undaunted, the memory rolled up on him with the force and determination of a freight train. Richard closed his eyes, bowed his head and let the memory of how it all started come back to him in graphic detail.
It all started ten years ago in this very office, it was the middle of the day and to Richard she was just another appointment, just another potential client. He glanced over the file and saw that she was being charged with assault and unlawful confinement. It was nothing out of the ordinary, or so he thought, as he closed the file.
"Send her in," Richard said he pressed the button on the intercom.
"Right away, Mr. Thompson," Julie, his secretary replied through the intercom.
The door opened up and in walked a tall woman in a business suit. She had black hair that fell in a dead-straight style, that her Chinese heritage had given her. Her brown eyes were little slits as she eyed up Richard, walking towards him with confidence in her stride. She was quite tall, unusually tall for a Chinese woman, and quite thin and slender. Her arms and legs were quite long and thin, almost appearing to be sticks attached to her torso. While she was an attractive woman, she didn't have an hourglass figure, her profile was fairly straight. Tight, trim and small would be the best way to describe her figure.
"Mr. Thompson, I'm Heather Lee, so good of you to see me," the tall Chinese woman said without the barest hint of an Asian accent as she shook Richard's hand firmly.
"My pleasure, Ms. Lee, have a seat," Richard said as he motioned to the seat in front of his desk.
"Thank you," Heather said curtly as she sat down.
"I've looked over your case and I think we can deal with this before it goes to trial. I have a few questions for you though. For one, how do you know the plaintiff, Mr. Jenkins?" Richard asked in a dispassionate and professional tone of voice.
"He was a client of mine," Heather said curtly.
"Are you in the habit of tying up and beating on your clients?" Richard asked with a raised eyebrow and a light chuckle.
"Yes, and they pay me well to do it," Heather said with a smirk on her face and eyed up Richard for a reaction.
"What?" Richard asked in a confused tone of voice. "People pay you to tie them up and whip them with a . . . riding crop?" Richard said as he momentarily looked at the file on his desk.
"I only deal handle men, and the beatings are just the beginning of what I do. And I never get any complaints from any of my clients," Heather said with a proud smile on her face and a laughing lilt in her voice.
"Well you have now," Richard replied with a slight chuckle.
"That idiot's only problem is that his wife found out about us, so he's just doing this to save his own ass!" Heather said in a voice full of loathing as she sneered at Richard.
"So you were having an affair with Mr. Jenkins?" Richard replied, asking for clarification.
"How can you be the great lawyer everyone says you are if you are this stupid?" Heather snapped with a disbelieving scowl as she shook her head. "I was not his girlfriend, I was his Mistress! He was my Slave and I was his Dominatrix! He would do anything I told him and loved it most when I whipped his bony ass! That is what I do Mr. Thompson, I have a select clientele of men who want to be Dominated, humiliated and made to serve me! I make a lot of money for it, mostly because I'm damn good at it, but also because I am very discrete," Heather said with an angry and commanding tone of voice as she stood up sometime during her speech.
"People . . . men like it when you . . . boss them around?" Richard replied in an absolutely flabbergasted manner, staring up at the aggravated and stern-looking Heather.
"A lot of rich and powerful men need to be put in their place now and again. They love being made to serve a worthy woman, a woman who knows how to treat a man like the worms that they are!" Heather said with a gleeful look in her eye, a growl in her voice and with a commanding presence about her.
For a brief moment neither said anything to each other as Heather and Richard just stared at each other. As they looked at one another they saw in the other's eyes that they were thinking about something. Richard was stunned and flabbergasted, for he had never really confronted anything like this. Sure he had heard about it but he had never had it described so vividly to him. The result left his head spinning and he barely noticed Heather walk over to him with long, smooth, definite strides. She stopped only when the chair touched her legs, she was standing right in front of him, between his legs. She looked down at him with a knowing look on her stern face and nodded to herself.
"I bet you're one of those men." Heather said with a laugh. "I bet you have a stiffie just thinking about what I might do to you, don't you?" Heather asked with a victorious tone in amongst her otherwise gruff manner.
"W. . . W . . . What?" Richard replied in a stammering stutter.
"Your cock is as hard as a rock, isn't it . . . Dickie-boy?" Heather said as she leaned in and towered over Richard who for some reason couldn't speak at the moment. "Thought so," Heather said with a laugh after she reached down and grasped Richard's stiff cock through his pants. "C'mon then, show me what you got!" Heather said as she stepped back a step and looked at Richard's groin expectantly.
"What?" Richard asked in an open-mouthed expression of shock.
"Pull out your cock! I want to see if you have any redeeming qualities, Dickie-boy!" Heather ordered with a stern tone of voice and glared right into Richard's eyes and waited.
"I . . . I won't . . . I c . . . can't!" Richard replied in what was supposed to be an outraged scream but only came out as a whimpering snivel of a protest.
"THAT WASN'T A REQUEST!" Heather screamed as she lunged forward and in a flash had Richard by the throat and squeezed, choking him. "Now, I've been patient with you, Worm, 'cause you're new, but I've lost my patience with you now. I'm going to let go of you in a moment and when I do, you're going to be a good little boy, drop your pants and show me your cock . . . aren't you?" Heather said in a low voice that dripped with rage as she spoke so close to him that their noses touched.
Heather stared at Richard as he sputtered and fought valiantly for air. She looked at him dispassionately as she waited for some sort of affirmation from him that he would comply. Richard's mind was going a mile a minute as he panicked from lack of air. He was now in fear of his life, so meekly he nodded into the woman who held his life in her hands.
"Good." Heather smiled with a self-satisfied smirk on her face as she stood up straight.
Richard inhaled deeply and coughed as fresh air filled his lungs. He looked up at Heather and thought about yelling at her, tossing her out or even calling the police. Such thoughts evaporated quickly as he looked up at her, standing over him with her hands on her hips. She towered over him and wore the expression on her face that she had little patience for the worm in front of her. Before he knew what he was doing, Richard did indeed drop his pants and underwear, as ordered.
"I've seen better, I've seen worse. Average is what I would say about that. Then again that is what I would say about you . . . average." Heather said as she glanced at Richard's hard and throbbing cock. "Average office," she said after giving the room a glance. "Average family," she said after picking up the family photo, glancing at it and tossing it on his desk. "Average life," she said looking Richard right in the eye with a look that pierced his soul.
"Yes," Richard agreed, though he didn't know why he did.
"Let's see if you know how to use that thing, Dickie-boy, give it a tug for me," Heather said confidently as she pointed at Richard's cock.
"Excuse me?" Richard asked with a queer look on his face.
"Give it a tug! Whack-off! Masturbate! Prove to me that a stupid little worm like you at least knows how to use that thing between your legs!" Heather spat with frustrated grunt as she shook her head.
While his mind was shocked and stunned, his hand wasn't, it seemed. For before Richard even realized it, his right hand had grasped his cock and started to stroke the shaft. As if, he was watching someone else do it, Richard looked down in great shock to see that he was indeed jacking-off in front of this strange woman. Heather looked down at him victoriously and laughed to herself as she watched him stroke his own shaft.
"That's enough!" Heather snapped as she grasped a clump of Richard's hair and pulled forward.
With a fearful look on his face, Richard found himself sprawled on the floor in frighteningly short order. He looked over his shoulder and back to the chair, his chair to see Heather now sitting in it like she owned the office. She smiled at him with daring, arrogant smile on her face for a moment, before she spoke up.
"Lose the pants and undies, Dickie-boy!" Heather curtly said, without moving a muscle.
"Yes," Richard replied, though he didn't know why he answered her
Nor did Richard understand why he was pulling his Armani suit pants off along with his silk boxers. In the end he was standing nude from the waist down, other than his socks. He looked in her face for a moment before quickly looking down at the floor, feeling small and scared. Richard didn't know why he felt weak in her presence, but not only did he feel like a worm, he felt excited because of it.
"Get over here and please me, Dickie-boy!" Heather said and Richard looked up at her and knew in instant knew what she wanted.
There she was, seated in his desk chair, with her skirt up around her waist, with no panties on at all. Her ass was scooted forward so that her crotch was at the edge of the seat. She leisurely stroked a finger up and down her slit as she glared at him, expectantly. Richard looked up at Heather's face, then back down at her pussy, and crawled over to her.
For some reason, Richard knew that he needed to taste that pussy. He also had a need to please her, to see her pleased with him, to serve her. Richard never took his eyes off of her pussy as he moved toward it. He licked his lips and then licked her pussy from the bottom to the top, without hesitation.
A satisfied sigh escaped Heather's lips as she leaned back in the chair, while Richard began to eat her pussy. Heather smiled to herself as she knew that he was hers, completely hers. Men were so easy, such simple fools that easily succumbed to her power. She had not met a man yet that once she set her sights on him, she could not dominate. Having a top lawyer under her heel seemed like a smart thing to do. For now though she would enjoy the adequate job he was doing licking her pussy.
Richard was never a man who liked to eat pussy, of his own accord. Once in a while, for special occasions he would eat his wife's pussy, but it was always hurried and not something he enjoyed. He still couldn't understand why he was on his knees in his own office eating a woman he never met before who was seated in his chair! For some inexplicable reason he was under her sway, he willingly did what she wanted, and loved knowing that he served her.
Richard licked from the bottom of her slit to the top, making sure to flick his tongue across her clitoris. As the first taste of her sweet pussy reached his tongue, Richard loved the taste of it. For some reason, this woman was incredibly arousing to him. He wanted to please her, he wanted to know that she was happy with him. He licked that pussy the best way he knew how, bringing up a finger to thrust into her wet pussy. After a moment of Richard's licking of Heather's pussy her hips began to gyrate, a silent way of showing her excitement.
"That's it Dickie-boy, eat your Mistresses pussy! Prove to me that you are worthy to serve me, make me cum and I may give you the privilege of being my Slave!" Heather said in a lusty growl as she started to pet Richard's head as he still ate her out. "You'd like that wouldn't you Dickie-boy?" Heather said with a hateful growl as she grasped a handful of Richard's hair and pulled his face away from her pussy.
"Yes Mistress," Richard said in a needy tone of voice from somewhere deep in his soul.
"Then what are you talking for? EAT ME SLAVE!" Heather said as she pulled on Richard's hair so hard that he was smothered in her pussy.
Richard redoubled his efforts to bring his Mistress to orgasm. He desperately needed to satisfy her, he loved the fact that he served her, even though he had been given little choice in the matter. He was too far along now to wonder what he was doing, he just accepted his place and ate that pussy with all he had, wanting nothing else to feel her come on his tongue, to come all over his face.
"Yesssssss!" Heather hissed as she slammed her legs around Richard's head, holding him in place between her thighs. "Cumming! Swallow it! Don't spill a drop Slave!" Heather moaned out as she thrashed about, snapping this way and that, while her orgasm ripped through her.
Eventually, her orgasm subsided and Heather's legs fell away from Richard's head. Richard continued to lick up all the abundant pussy-juice that abounded the satisfied Mistresses pussy. For a moment she laid there, luxuriating in the oral attentions of her new Slave. Without warning, she brought her right leg up and placed it on his chest, near his shoulder. With a hard push, Richard flew backwards, landing hard on his ass, staring up at his Mistress with a look of hurt and shock on his face.
"Don't move Slave, I want your cock!" Heather said as she stood up and walked over to Richard who was still lying on his back beside his desk.
Without a word she positioned herself over his cock, lined it up and sank down, taking his whole length in her. When she was sitting on him, groin on groin, a satisfied smile on her face as she looked up and off into apace for a moment. When she looked down at Richard she had a sneer on her face.
"Don't you dare cum! This is for me, not you, Slave!" Heather said with a firm tone of voice as she bounced up and almost off of his cock.
At a quick and steady pace Heather bounced up on Richard's cock solely looking for her own release. Richard had to concentrate hard not to loose control and cum deep within her. Every so often Heather would slow down the pace of her bouncing to an excruciatingly slow, grinding fuck. Then she would start to bounce up and down, at a blinding pace. Near the end her whole body started to roll and convulse as her pleasure quickly reached its peak. Suddenly, Heather slammed down on Richard's cock one last time and opened her mouth and eyes wide. No sound came from her though as she deeply gasped for air as her body shook and twitched. With a surprising suddenness, Heather fell forward, catching herself with her outstretched arms.
"Good, Slave, you didn't cum," Heather said with a satisfied smile before standing up. "You can cum in this," she said as she tossed Richard a box of Kleenex that had been on his desk. "Call that idiot and tell him that I'm not going to give him a penny, and that I will make sure we take this to trial where I will get up on the stand and tell everyone in detail what we did together. I even have pictures and videos, that should make him shit a brick," Heather said as she straightened up her clothes before she fished though her purse. "Be here, Friday at five," she said as she tossed Richard a business card that landed beside him.
"Yes Mistress," Richard said as Heather walked out, not looking back once.
That was how it all started for Richard ten years ago and was why he was sitting in his office, feeling especially depressed this Friday. This memory brought a smile to his face as he thought of her and the things they did together. Richard knew that it had been just a professional relationship, he knew that the only reason they got together was because he paid her. That didn't stop him from loving her, not only what she did to him, but the woman herself. That was what made this parting all the much harder, for he not only lost a Mistress, but a great love as well.
Richard took a long drink on his scotch and sighed heavily. He rubbed his forehead and wiped away the tears in his eyes, for he knew the next memory that would visit him. He knew his thoughts would turn to two weeks ago and how things ended between them. Was there something he could have done differently? Could he have said or done something that might have caused her not to break it off?
Two weeks ago to this night, Richard was at his Mistresses place, as he had been practically every Friday for the past ten years. As he looked back he could almost feel the collar around his neck, the restraints on his wrists and ankles. It was a large, studio space, converted from an old warehouse in a light-industrial part of town. Richard was standing with his feet chained to the floor and his arms chained above his head. He had a large but-plug stuffed up his ass with instructions to not let it slip out, no matter what happened.
His Mistress was standing nearby in thigh-high leather boots with stiletto-heels. She also wore a vest made completely of 1 inch wide leather straps that crisscrossed across her torso. Her leather gloves rose to her wrists and the whole outfit was made of highly polished black leather. In her hands she held her favorite item, her riding crop.
Richard's ass stung and glowed red from the whipping that he had just received. He had taken the beating like a good Slave, thanked her for each hit and made sure that the but-plug didn't slip out of his ass. There was a pause in the whipping and Richard wondered what would happen next, this was part of the excitement, the not knowing, nor having any control over it. Whatever would happen, would happen and he would have to take it.
He could hear some rustling in some drawers behind him and knew that his Mistress was getting something out. At least he knew that the activity would change, but from the sounds he couldn't guess what it was. He didn't look behind him for he knew that he had to keep looking straight, to look anywhere but straight ahead was forbidden. The winch that was attached to the chains that bound his wrists sprang to life and the chains lowered towards him.
"Get on your, hands and knees, Slave," Mistress ordered him curtly.
"Yes, Mistress," Richard replied obediently and did as he was told.
Richard waited on his hands and knees on the cold concrete floor, not knowing what would happen next. He heard footsteps approach him from behind and could feel her presence, his Mistress was near and he smiled to himself, knowing that. With an audible pop and shocking suddenness, his ass felt cavernous without the large plug in his ass. It was now that Richard had an idea of what was going to happen and mentally prepared himself for the invasion. When he felt something pushing at rear entrance he knew without a doubt and momentarily tensed up.
"Relax, Slave or this will hurt much more," Mistress said as she aimed the lubed up strap-on dildo at Richard's ass.
Pausing only for a moment Mistress then leaned forward and pushed the plastic dick into her Slave's ass. With steady pressure she kept pushing forward until the whole thing was inside Richard's ass. Back she withdrew until just the head was inside his ass before she thrust forward, shoving the whole thing back in. She set up a quick and steady pace, not considering at all that Richard may need a moment to adjust to the size of the new anal invader.
Richard bit his lip as a tear rolled down his cheek, his ass was on fire, but he dared not shout out. He silently took the pain and quietly reveled in the knowledge that his Mistress, a woman, was fucking his ass with a strap-on dildo. The bizarre and taboo thought always heightened the pleasure for him, and strangely enough he got off on this.
At a quick and steady pace Mistress fucked Richard's ass, smiling to herself at her complete dominance of him. To Heather, this was the ultimate sign of her dominance over a man, for him to let her fuck his ass. This was the way she showed both of them that he was her bitch! She got a sexual charge out of doing the act and even more of a sexual hit when the men started to enjoy it. After a few minutes of this anal fucking, she knew that Richard was about to cum. After ten years of being his Mistress, she knew when Richard was about to cum. With a stifled grunt and a twitch, his cock started to spurt and Richard came all over the floor as she still fucked his ass. She continued to fuck his ass until his excitement had cause his cock to regain its hardness once more. She pulled out of him as suddenly as she had entered him, and left his ass looking cavernous, as it started to close up. Quickly removing the strap-on pleasure device she returned to Richard who was still on his hands and knees, still saying nothing.
"Lie on your back," Mistress said as she approached him swiftly.
Richard scurried to get into position and made it just in time as Mistress stepped over him. She kneeled overtop of him, and lowered herself on his cock, making sure not to smile as she did so. He knew that she liked his cock, he could tell, even if she didn't show it outwardly, he knew she needed his cock. With swift and definite strokes she raised and lowered herself on his cock. Richard's ass was on fire from both the beating and the ass-fucking. This let Richard last much longer than usual because it detracted from the pleasure of his Mistress using his cock. The pain had a mixture of pleasure in it for him as she bounced steadily on his cock. Her bouncing turned especially hard and harried near the end as her excitement got the better of her. Richard was fast approaching orgasm and didn't want to be a bad Slave and cum inside her.
"Gonna cum, sorry Mistress," Richard said with gritted teeth as he fought hard against the impending climax.
"Do it, Slave! Cum in me!" Mistress ordered as she looked down at Richard in a deadly serious manner.
The shock and wondrous gift of being allowed to cum in her pussy for the first time eve, pushed Richard over the edge and he came hard, fast and long inside the innermost depths of Mistresses pussy. From the first time feeling his hot cum shoot deeply inside her Mistress came quickly and in the most intense climax she had had in years. Heather moaned out a mournful scream as she came, remaining motionless on his cock for a moment.
Slowly she opened her eyes and looked down at him. For the first time there was a hint of love in them before that look turned to sadness then her eyes drained of all emotion. She let out a heavy sigh and got off of him, then without saying a word she removed Richard's restraints and then his collar.
"Get out, we're done, Mr. Thompson," Mistress said in a casual manner as she reached for a bathrobe and put it on.
"Mistress, I don't understand. What's going on?" Richard asked with a most troubled tone of voice.
The only time she had ever called him Mr. Thompson was when she first met him. After that it had always been: "Worm", "Slave" or "Dickie-boy." This was completely out of character, as well there time was not yet finished, usually they went for at least an hour more.
"I said we're done, now get out Mr. Thompson. Don't let me catch you around here again or I will call the police and then your wife . . . in that order." Mistress said to him in a calm but definite tone of voice as she lit a cigarette and began to smoke it.
"B . . . but Mistress? I don't understand." Richard implored in a hurt tone of voice as tears welled up in his eyes.
"You really are an idiot aren't you, Dickie-boy?" Mistress said with a disgusted scoff. "Do you know what today is? Today marks ten years to the day that you have been coming to me. Most men, by now, find some way to get what they need from the wife. You keep crawling back here like some dog who doesn't know what else to do," she said with a scoff as she picked up Richard's clothes and tossed them at his feet.
"But, I've been a good Slave! I love you, Mistress, let me stay. I need you," Richard said with all the love that he felt for her and looked deeply into her eyes.
"GET OUT!" Mistress screamed as she rushed toward him and slapped him hard across the face. "The only reason you were ever here is because you paid me for the pleasure of being my Slave!" she growled into his face with hatred, a tear running down her cheek as she did so.
"But Mistress?" Richard said with shock and confusion.
"You bore me, you pathetic little man, get out," Mistress said and walked away from him, facing away from him, smoking her cigarette.
Nothing else was said as Richard got dressed and left for the last time. That was it, after ten years of pleasing and serving her, it was over. It was over as suddenly as it had started, and the loss was something Richard was still dealing with. The two weeks since it happened had been hard to bear for him as he searched his mind for what he should do next. Since it was over there was little need to tell Taryn, but he still needed the dominance of a Mistress. He was lost and confused, not knowing which way to turn, what the right course of action was. It was with a heavy sigh that Richard drank the last of his scotch, before leaving his office to go home. He had no more answers than when he started brooding in his office, hours ago.