by amber
Waiting for Mistress Isabella, he sat motionless, listening in the dark. Outside he could hear the rain coming down, whispering softly to him. His eyes were closed and he dared not open them. He thought of the card in his pocket that she had given him the night before, instructing him to come here to her home. He had been given specific instructions. “You will enter my home and proceed to the first room on your right. You will disrobe, and you will place yourself in position on your knees with your legs spread. Your head and shoulders will be on the floor, and your hands will be behind you spreading your ass as you put it up for inspection. You will not speak, or move until directed otherwise. Your eyes are to remain closed at all times until told to open them. If you violate any of these instructions you will leave immediately, you will not return, and I will discuss your behavior with my Father. Now, do you still want to continue? If so, you have your directions.
Such a quick sequence of events. He was at a business mixer. It was another boring event, but he had grown accustomed to attending. It was just a part of his job as the new VP of Marketing.
Just as he thought he could bear no more, something caught his eye. As he turned his head, he saw her. She was a raven-haired goddess! As she strode slowly and elegantly into the room, he took her in. Her long dark tresses cascaded in soft loose curls down her shoulders and back. Her eyes were a deep almost emerald green, piercing and deep. Her skin was flawless, smooth like fine porcelain, with full, pouting red lips. She wore a long, flowing black gown that plunged in front and back, giving hints of her hidden beauty as well.
As she entered and was greeted by several people, he stood motionless, and speechless, mesmerized by her beauty. She turned and her gaze fell on him. He felt the blood draining from his head and his throat drying. His hands were perspiring. Her stare did not leave him as she approached. “Hello, I am Isabella”, she said, holding out her hand. “Oh, um hi, I am James”, he replied taking her hand in his. He bent forward and kissed her hand softly, taking in her fragrance. She smelled fresh, and sweet. “I see you are trained in proper manners. That can be a valuable trait.” He blushed at this comment.
“Are you here with someone”, she asked. “No, I am just here for a bit to meet the new partners to our firm and see that they are made comfortable. Trouble is they are usually loud and obnoxious and bore you to tears with the same old jokes and stories.” “Really? What is the name of the firm?” “Jacobs and Jacobs, the new law firm here. I am supposed to meet their CEO tonight and make him feel at home. But I was just planning on saying hello and pushing him to one of the other execs and sneaking out early. I hate these functions. Besides he is probably old, bald, fat and lonely.” Her lips turned upward at the corners in a Cheshire grin at the remark. “Hmmmm that is most interesting. So you do not think he is worth your time to entertain even though he is bringing a large profit to your company?” “Oh no, not that, certainly, I would just much rather spend my time with a beautiful lady such as yourself. “
“Well now, isn’t that just sweet irony?” “Excuse me?” “Darling, let me re-introduce myself. I am Isabella……Jacobs, and my father is Antonio Jacobs. Perhaps you have heard the name?” She toyed with him like a cat with a mouse. He sputtered and almost dropped his drink. “Oh God, you mean? So you are……you’re”…. “Yes darling, i am the old, bald, fat, lonely man you spoke of. I am sorry to disappoint you.” Suddenly, James could not breathe, his tongue was swollen and he felt faint. What had he just done? His career would surely be over once his boss heard of this. How could he be so stupid? He fumbled for words to apologize for his remarks, but could not find them. Oh no, I am so sorry Ms Jacobs, I didn’t mean any disrespect to you or your father, it is just that… Yes, yes, darling, I know, you were expecting someone quite different. I am not normally tolerant of disrespect from men though. Perhaps I can find a way for you to make amends for it this one time. What are you willing to do to earn my good grace again and save your position? Anything at all Ms Jacobs, honestly, I meant no offense; please let me make it up to you. I will do whatever you ask to make it right. Choose your words carefully James, anything is a very large commitment. She looked into his eyes and saw sincerity, not arrogance. It was this that might save him. “Very well, here.” She handed him her card. This is my address. You will be there tomorrow promptly at 6 P.M. Is that a problem? No Ms Jacobs, not at all, anything I can do to make up for my behavior, please, I am more than willing. Hmmm there is that word again. Twice you have used it James. You may leave now. See to it you read my card carefully and do as you are told.
With that she turned and was gone in the crowd. He turned the card over and saw several lines written there as he read them; he began to wonder what he had just gotten himself into.
“Spread those cheeks”, Isabella yelled at James. Slowly he reaches back, spreading the white globes of his ass, feeling embarrassed. “And do not look at me without permission, boy.” James lowered his head, his eyes cast on the floor.
“James lift your ass and spread those cheeks for my inspection”, Isabella purrs. He moves to obey. Isabella taps her boot impatiently, then squats downs, cigarette hanging from her dark crimson lips, as her gloved finger probes his shy tight asshole. “You are a naughty boy aren’t you James?” “Yes Ma’am I am”, he replied. Her finger slides in further and the glove is silky. “Do you like my finger in your ass James” she says then laughs softly. “Yes Ma’am”, James says. Quickly, it is pulled out, and James feels a sudden hard slap on his ass, and then the heat of the rising handprint in his flesh. Isabella stands and takes a deep drag, then sighs. “Up on your knees, boy. “Hands behind your neck.” Look at me.” She grasps his chin. “You thought I would be a hot but easy lay… and then daddy would give you a cushy ride on our family fortune, didn’t you? You thought I would be under your thumb. Is this correct boy?” “Uh no Ma’am, that’s not it at all.” Isabella squeezes James’ chin, then slaps him hard across the face. “Liar!” A tear comes to James’ eyes as his mind tries to make sense of his predicament.
“I only wanted to take you to dinner Ma’am.” Isabella grabs him by the hair and pushes his head down. “Lick my boots, boy…. shine them with your lying tongue. You are nothing but a slick, smooth talking, player.” James’ tongue slides over her boot. “I despise players, she says to him. Both of them James! I am losing my patience.” “Yes Ma’am.” “Have you never been taught manners by a strong woman James, or are you accustomed to being served” she asked with a sneer, her voice thick with sarcasm. Quickly, James turned his lips and tongue to the other boot, traveling over the supple leather.
“You will not be served here. Your pleasure means nothing to me.” Looking up into her eyes, James replies, “I am not sure how to respond Ma’am.” “Your desires, your needs they are nothing to me”, she says as she sits, smoking and watching him, frowning slightly. “Speechless James? A loss for the correct words?” “Yes Ma’am” he whispers. “Why did my dad ever hire such a loser”, Isabella says as she laughs. ” Please it’s not how you think” “The old man must be getting senile” she mused to herself. “When I take over it will be a woman’s world.” “Yes Ma’am.” “And what of your job when this happens my dear James” she asked? “Can you serve coffee, take dictation or type perhaps? I will need a secretary.” Isabella pushes him away with her boot and he stumbles backwards blushing with shame.
“Kneel before me with your hands behind your neck again and your eyes lowered. I am going to change.” She says as she flicks her cigarette, the hot ash landing on his thigh. She turns on her heels and walks out of the room. As he hears her heels clicking on the floor, he contemplates his fate. He imagined his entire world being turned upside down. Why hadn’t he kept his smug comments to himself? He always had a way of letting his mouth get him in trouble. He hoped that he could satisfy her and somehow salvage his career, which now seemed precariously balanced in her hands.
Isabella returned to the room. She was wearing a tight latex halter top and mini skirt (very short) and thigh high black boots. She walks to a nearby table and picks up a fancy table lighter, it’s a stone lion with wings. She lights a cigarette with it and sneaks a look at the pathetic, shaking man before her. She smiles, enjoying the power she holds over him. She knows James is peering up at her, but pretends not to notice. She walks to the entertainment center and starts a CD. The room is filled with a haunting, seductive Italian melody. Isabella turns and faces her new toy. “Stroke your cock James,” she says as she smokes her cigarette, taking long slow drags. James hesitatingly moves his hand to his cock. It has stirred from the vision before him and is already semi-erect. He slowly slides his hand up and down the shaft. He feels it stiffen in his grasp. Isabella watches intently as it grows and becomes fully engorged.
“Did you masturbate earlier James, before you got here? Were you pretending I was sucking it? Maybe you were visualizing that you were sliding inside me?” “No Ma’am” “Liar!” She walked up to him and grabbed his chin in her red taloned fingers. “You will learn to never lie to me boy”, she screamed as she pulled upward on his chin. “Stand!”
James quickly scrambled to his feet, not wanting to risk further incensing her. With an evil grin, she trailed her cigarette over his chest just close enough for him to feel the heat. James flinched, but dared not move away. “She is crazy”, he thought to himself, but he was in no position to argue with her. He needed his job. Isabella stared into his eyes, wondering what his thoughts were.
She walks over and presses a button on the wall. It opens a hidden panel and there is another room. It is darker, with strange items inside. He can see hooks and O-Rings, benches, and wooden crosses. “Jesus, what the hell is happening?” he thought. “Follow me James, now!” He followed her slowly, hesitantly. “On your knees boy!” Feeling defeated and humiliated, James slowly lowered himself to his knees before her. He could feel the cold stone of the floor beneath him. The room was almost medieval in appearance. The floor was stone, the walls, were covered in stone also. Not like bricks, but more like flattened cobblestones. It reminded him of a torture chamber he had seen in the B-rated horror flicks. As his eyes adjusted to the dim lighting, he could now see the true evil nature of the room. It was adorned with all manner of painful devices on the walls. There were whips, and crops, tables, and one wall was complete with chains and manacles bolted solidly to it. He knew this was not a game she sometimes played. She had furnished it too well and too completely for it to be anything less than real. She spoke to him again. “You are beneath me, inferior to me. You will stay down, do not rise from your place or it will cost you. His mind says, “This is insane. Get out now”, but his lust says he must follow this lovely creature. She is a Goddess. He knows he must obey her. Not only because of his job, but because he is taken with her superiority, her control and her beauty. She exudes a wild, strong sense of passion that he can almost smell and taste in her presence.
Isabella walks to a nearby table and retrieves something. He cannot see what she has in her hand. She returns to him takes one hand in hers. She places a leather wrist restraint on him, and then does the same with his other hand. She then restrains his ankles with similar items. Next, she places a leather collar around his neck with a large steel o-ring attached securely to the front. He can feel his excitement rising. His manhood stood rigidly at attention. She notices it, but chooses to ignore it. “You want to make amends for your deplorable conduct, don’t you?” “Yes Ma’am”, he quickly replies. “So you will be my slave for tonight, won’t you?” “Oh yes, I will do anything you ask, just please don’t tell your father.” “I have Daddy wrapped tightly around my little finger. He will give me anything I want, including the pleasure of dismissing you if I choose to.” “I am sorry if I offended you at the dinner. I had no idea who you were. Can I please just go and we can forget this mistake of mine?” “I forget nothing you sniveling coward. Now shut up, you are boring me,” she says as she looks at him sternly.
Isabella dragged him by the ring in his new collar to the cross. It looks like a large X. She secures first his wrists, then his ankles to the large, solid, wooden apparatus. “Can you move James?” she asked? “No Ma’am” he responded. Satisfied that her prey is securely fastened in place, she turns and walks to the table again, lighting another cigarette. “My, how divine, a bitch boy, ripe and unexplored all mine for my amusement. You must be feeling totally emasculated and humiliated. Have you ever been whipped slave”, she asks as she approaches him. She walks behind him and caresses his ass, back, and thighs. Her long red nails gently scratch him as she reaches around and strokes his balls. Fighting to keep his composure, he replies, “No Ma’am, I have never been whipped.” With a sigh and a smile, she lightly presses her cigarette against his smooth ass cheek only for a second. It leaves a small red mark. He jerks in pain. Isabella laughs out loud and walks away for a moment. James can hear her picking up something else, but he cannot see what she has chosen. His breathing is becoming ragged and his mind is in over drive. Panic is setting in as he wonders how far she is willing to go in causing him pain.
She returns to him and speaks in a soothing tone, “Relax slave, this will be easier for you if you do not fight it. Surrender yourself to me. You gave your word you would do anything I asked.” Feeling defeated, he dropped his head and responded, “Yes Ma’am.”
“I am going to let you experience the riding crop. It will hurt you, but it will give me much pleasure. Do you wish to excuse yourself James? Perhaps you wish to beg for mercy?” “No Ma’am, I gave my word.” A smile crossed her lips as she said, “Very good slave, you may have potential after all.” She tapped the leather crop lightly on his ass and he flinches. He is startled; it does not hurt not yet. Again she taps it on his firm, milky white cheeks, and then she moves her strokes to his thighs. Feeling the light taps, he says to himself, “This isn’t so bad.”
His skin starts to warm a little, and suddenly, the crop strikes him hard across one ass cheek. James jerks, the pain searing his brain. Instantly, a dark blue stripe appears on his flesh. He tries to plead with her, “Ma’am, please forgive me. I will never disrespect you again.” She caresses his back with the crop. “I cannot forgive you yet James.” And, since you agreed to the punishment, you may not change your mind now.” He bites his lip, knowing he is sure to experience much more before she is finished with him. Again the crop strikes right next to the other mark, this blow harder than the last. James closes his eyes, trying to focus his mind, to be able to bear the pain. He remains silent now.
Another strike lands right next to the other two and then the other side…three strikes, hard, biting into his flesh.
Isabella momentarily walks away from him, letting his mind play the game it will play. James is sweating now, his mind a blur. He cannot think coherent thoughts as the secondary burn of the strikes remain potent and fresh in his mind. Isabella selects a heavy kangaroo hide flogger from the wall. She knows this one is the more severe her collection of floggers. The tails are cut in a v-pattern at the tips. This makes them more painful when hitting the flesh. She walks to him and trails the instrument over his back; the weight of the leather is cool and soothing. Suddenly without warning, she raises it and strikes him with force in the middle of his shoulder blades. The tails make a resounding thud as they impact his skin. It reddens immediately. It stings, but the sensation is much different from the crop. He actually enjoys the feeling. It is strong and a sense of warmth, not pain spreads over his skin. Again and again she strikes him, varying her speed and force. His skin starts to numb. Then she hit his thighs both of them twice each not quite as hard.
She drops the flogger and takes a deep drag as she walks up behind him. He can hear her heels clicking on the floor. She exhales and he feels the smoke on his back. He lets out an audible sigh as her nails trace the marks on his back. She is very pleased with them. Somehow, inside himself, he knows he has started a journey he does not want to return from. She has captured his mind and soul. He will follow her anywhere and endure anything she wishes. “You have some very nice marks slave”, she says to James. “Thank you Ma’am”, he quickly replies. She walks off and he wonders what could be next; will she let him go? Is it over? Does he want it to be? He is confused. He wants to leave, but cannot say it. He has to stay. He has to please her. She is away for at least ten minutes. He wonders if she has left him and for how long. He can feel his fingers growing cold from the weight and his legs ache. His ass and back are on fire. Yes, he loves it. It is all so strange and new to him, forbidden and taboo. Isabella walks back in and undoes the clips that attach him to the cross and then she leads him to a sofa. He follows her on shaky legs, is mind still foggy, as though he has been drinking.
She tells him to kneel and place his hands behind his neck with his eyes lowered. “This is my preferred position James when you are to wait.” He assumed the position gracefully, lowering himself to the floor at her feet. “This is the position of a slave; an obedient slave. Do you understand?” “Yes Ma’am”, he replies. “Knees parted more James.” He spreads his legs further slightly, feeling exposed and embarrassed. “You are open to me; willing, waiting, submissive. “You are here to serve me.” “Your ego is not welcome here nor your arrogance.” “Yes Ma’am.” I could not care less where you have been educated, or what you know. You are now my slave and the only thing you are to think of is serving me.” “Yes Ma’am”, James responds, sensing somehow he has found his destiny. Isabella picks up a large dildo; about 9 inches and he looks up without permission and is shocked! Knowing what is coming, he tries to salvage his male pride. “Ma’am, please no, I am not gay.” Isabella smiles at him as she tightens the straps to the harness. “We are all a little gay, dear boy. It is just deeply hidden She sits on the edge of the sofa smoking, her fake cock is sticking straight out. He is embarrassed. “Crawl to me James”, she orders him. He crawls slowly to her. “Ask me if you can suck my cock, James,” she says with an evil smile. His cheeks flush. “Please Ma’am, may I?” “May you what James?” “May I please suck your cock?” he asks feeling completely humiliated. Mmmmm yes my little bitch such a delicious mouth; it was made for cock sucking.” “Take my cock into your mouth and pleasure me slave.” He slides his lips to the head. Isabella hangs one leg over the side of the sofa and exhales smoke in his face. His cock hardens at that. He feels her cock hit the roof of his mouth. He backs off slightly; it is too big, too much. She grasps the back of his head and forces it forward, pushing her cock deep into his throat. He gags and struggles to breathe. She begins to slowly move her hips fucking his mouth. With each stroke his throat relaxes a bit. Soon she is sliding in and out with ease. James finds his mind floating and wondering, ” Is this what it is really like?” He pictures a real cock. “No I am not gay”, he tells himself. “Are you enjoying this James? Perhaps a real cock soon?” She is taunting him now.
He cannot speak his mouth is full. He nods his head, shamefully admitting a dark new desire. She has broken his will. Isabella rings a small bell from a table near the sofa. “Keep sucking me off boy, I am just ringing for my butler. James looks up trying to see what is happening, but he cannot move his head. She grasps the back of his head again, forcing him to slide up and down and again forcing her cock into his throat. He hears someone enter and some shuffling. He is very embarrassed. He is nude and sucking cock. He just wants to hide. “God, please make them go away,” he says to himself. He sees her nod at the unseen person and someone kneels down behind him. Strong, hardened male hands caress his ass cheeks. He feels a wet sensation run down between his cheeks and realizes it is lubricant! “Jesus, he is going to fuck me!” And a gentle probing as a large finger forces its way into his nether hole and explores him. “Keep sucking James”, Isabella says in a dreamy voice. Looking up, he sees her smoking sexily. “Relax and just go with it”, she tells him as she smiles at him. The finger is slowly pulled from in him and he relaxes his ass. He is starting to feel the femininity of the situation; imagining the feeling a woman feels. He feels something press up against his asshole again larger, harder than the finger. He realizes it is a cock, a real one. As it eases in, it hurts and James tenses for a moment, and then forces himself to relax. He knows it will hurt worse if he tightens up. He feels as though it is splitting him in two and moans into Isabella’s cock. Slowly, inch-by-inch, the huge phallus sinks deeper into him making him feel very full. Suddenly it is all the way in and still. James feels very full but continues sucking her cock. He is losing himself in this strange, new world. His jaw starts to ache. But, he finds himself picturing himself as a woman pleasing her two men. The man behind him grabs James’ hips and starts fucking, thrusting in and out. It hurts at first, then slowly
James realizes the stranger is enjoying his ass and it makes him feel good.
The pain is replaced by a warm glow; pain turns to pleasure. James starts to move his hips back to meet the man’s thrusts and he swallows Isabella’s cock deep with each plunge. “How does it feel to be a little slut, James; pleasing two men” she taunted. The man’s cock seems to grow larger and harder and he is moaning. James is now moaning like a cat in heat the cock feels so good in him; fucking him like a whore. He is depraved and loving it. Isabella eases her cock out of your mouth and removes the harness and pulls James’ face to her pussy. “Make me cum James”, she growls. He dives hungrily into her wet slit, licking between her lips; sucking hungrily and devouring it. His tongue laps at her clit, his fingers tracing her folds. He nibbles on her clit, biting it lightly, nursing and loving it. The cock in James’ ass is thrusting harder and more urgently now, and James redoubles his efforts on Isabella sucking her in frenzy; determined to please her. He takes her clit between his teeth, scraping, nibbling, sucking, and biting it lightly. He can feel her tensing up, her hips start to quiver and shake. She lifts her hips to his mouth and hears her breathing becoming labored. James is being fucked like an animal; panting and sweating the stranger rams into him, his cock growing larger. It is too much for Isabella and she feels herself tumbling over the edge toward a crashing orgasm. Every nerve in her body is alive with electricity.
At the same moment, James can feel the man tensing in him and then; a flood of warmth fills his insides. The man is cumming in him and filling him with his seed. He rams his cock in a final time, holding it deep inside as he shivers; the last strings of cum filling James. His ass contracts around him. Isabella pulls away from James and takes a deep breath to regain her composure and her power over her slave. James lips are coated with her sweet nectar and he feels the cock in him soften and slide from him. As the cock pops free, he feels emptiness inside. “Lower your eyes James. You are nothing more than a cumslut now and are not worthy of looking us in the eyes without permission” Isabella says to him. As the butler dresses he too lowers his eyes. “Oh my God, she had the butler fuck me,” he thought. “James why are you blushing?” “This woman is evil incarnated,” he thought to himself. He kept his head lowered until she spoke again. “You may look at me now slave. Are you embarrassed?” As James looked into her beautiful eyes, he was hypnotized by her beauty and power. “Yes Ma’am”, he responded meekly.
“I am giving you a week to think if you will come back here next Saturday night. I will not speak to my father during that time. It is a reprieve. Next week will be hard, but it will save your career. And, you will get to meet Max.” “Max”, James said in a questioning voice. “Yes dear, Max is a very special friend of mine who has a great interest in training people just like you…
