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If the Shoe Fits By Cheri Amour Kathleen O'Connell stood just outside the doorway to her palatial bedroom, taking in the exciting tableau before her. She was easily visible to the room's only occupant, her stepson Andrew Dupre, but she had no fear of him seeing her. For he was kneeling in a reverent posture in front of the wide open doors of the spacious walk-in closet opposite her vantage point. One might have said he was praying, but for the fact that he was completely naked and he was holding one red high- heeled pump up to his face, while his other hand stroked his rampant erect penis which was pointing down toward a similar red shoe on the floor in front of him. Kathleen felt a sense of power building in her as she listened to the sounds of the young man sniffing the scent of the shoe he held close to his nose, while his other hand worked to bring his hard, red cock to what looked to be an imminent orgasm. Kathleen smiled in triumph as her suspicions of her stepson's secret activities were confirmed. She had made sure to tell Andrew that she was going into the city on a shopping trip before departing the house about an hour before. The eighteen-year old had responded with only a casual grunt when she had told him where she was going. She had actually driven away from the house, but then returned, parking down the driveway and quietly letting herself in the back door. Now she had proof of his inclinations and she had already made plans for using them to control the boy for her pleasure. For his part Andrew was oblivious to his surroundings as the sight, smell and feel of his stepmother's shoes engulfed him. Kathleen had been his father's trophy wife, years younger than her husband. In fact, she was only ten years older than Andrew himself. Andrew had to admit Kathleen was beautiful with her striking figure, midnight-black hair and opalescent blue eyes, but he had never really warmed to her. She was too young to seem like a parent, but too old to be a friend to the only child. So he had tolerated her for his father's sake. Since the death of his father in a car accident eight months ago, he had coexisted with her, since the will left her in control of his father's estate until he turned 21. That seemed unfair to him, but Kathleen was a lawyer and seemed to have influenced his father into writing what other lawyers he had consulted said was an unbreakable last will and testament. In truth he couldn't complain, since Kathleen had continued to pay his tuition to a top boarding school in Massachusetts and had allowed him plenty of spending money while he was there. He was now home following graduation and spending the summer until college. He had been admitted to an Ivy League school, which Kathleen had agreed to pay for from his father's medical equipment company fortune. And he was determined to use the times when Kathleen was out of the house to pursue his own pleasure. He had had many such opportunities in the last few weeks. He often found himself alone in the house, since his stepmother spent much of her time out shopping to add to her already extensive wardrobe. That pleasure had come to revolve around the infinite variety of shoes Kathleen owned. She was almost always dressed in the finest fashions with coordinated accessories, including her many pairs of boots and shoes, which she always kept lined up neatly in her large bedroom closet. Andrew had never felt aroused by a woman's shoes until his last Christmas break six months ago, when, bored and alone, he had been rambling through the house out of boredom. After wandering into Kathleen's bedroom, he felt impelled to peak into her closet. When he opened the closet doors on that fateful day, he was struck by the endless diversity of shoes, boots and sandals he found. The thought struck him that all men's shoes were much alike. In fact, they were boring in their similarity. But now, the rainbow of colors and textures, the differing heel-heights and the uncountable straps, buckles laces and zippers before him were mesmerizing. And the subtle scents he breathed in from the shoes seemed to cause a tingling in his groin. Dazzled by the display, he slowly knelt and reached out to a pair of black ankle boots with three-inch heels and side zippers and ran the tips of his fingers over the ebony suede leather. He gasped at the sensuous feel that seemed to shoot straight from his fingers to his groin. He couldn't help himself as he swiftly unzipped his trousers and pulled out his already rampant penis. It was beating like a second heart as he stroked himself and within seconds his semen jetted out onto the floor of the closet. He seemed to have no strength left afterwards and he could only remain kneeling and gasping for breath after his exertion. Finally, he was able to rise, but then he realized he had to clean up his mess if he did not want his stepmother to notice the spots on the carpet. He managed to sponge the spots clean and the carpet had dried by the time Kathleen returned home. But since that time, whenever he was home from boarding school Andrew would explore the erotic possibilities of the shoes. He was careful to always clean up after himself and return the shoes to the precise positions they had been in when he started. His pretended indifference to visits home had become a complete sham. He had become insatiable. As often as he could, he worshipped those shoes. They had indeed become fetishes for him, imbued with power to give him the greatest pleasure he had ever known. Kathleen smiled broadly as she thought back over the preparations she had made for this moment. Quietly, she stepped through the door and into the bedroom. Her soft steps making no sound on the thick carpet. In truth, she could have made any amount of noise and Andrew, consumed by the feelings of sexual arousal coursing through his body, would never have noticed. Indeed, he simply remained kneeling and stroking himself until Kathleen was right behind him. Then in an instant, his world was shattered as his stepmother reached out and seized his right earlobe with a crushing grip. Andrew shrieked in sudden agony, dropped the shoe he was sniffing and reached up to try to relieve the terrible pressure on his ear. But suddenly, his left arm was being wrenched up behind his back by his unknown assailant, who proceeded to push his upper body forward until his head touched the floor. As he was still kneeling, he found himself unable to move. He could not straighten his body against the pressure. He could only cry out in pain and fear and beg his assailant to release him. Then came words he dreaded. "So, you disgusting pervert," his stepmother hissed at him, "this is how you spend your time while I am gone. I suspected as much! Lately, you seem to have been careless covering up your activities. I've noticed strange spots on my some of my shoes when I put them on. Spots that looked liked dried semen. I didn't have much difficulty figuring out whom those spots could have come from. Well, if you like my shoes so much, I will see to it that you get your fill of them. Stand up!" With that Andrew felt the pressure ease enough for him to slowly get to his feet. But the grip his stepmother had on his ear and wrist never relaxed as she used them to propel him toward her large four-poster bed. He stumbled before her until suddenly she was sitting on the side of the bed and he was across her lap. She had to let go of his ear and he gasped in relief, but she maintained her hold on his wrist, forcing it across his back and pulling him into her body so he could not squirm off her lap. He did not notice Kathleen reach down and pull an object from under the bed until she flourished it in front of his face. "Perhaps you'd like a sample of this," she said, brandishing a pink leather slipper. "It is probably not as sexually exciting to you as a high-heeled shoe, but I think it will give you a powerful lesson just the same." With that, she began to spank his bare bottom with the slipper. It was quite flexible, with a thick, smooth sole. As Andrew soon learned, it stung his quivering naked flesh as his stepmother smacked him with it again and again. He soon felt its sting building and heat rising in his ass cheeks. He tried to squirm free, but with his arm locked painfully against his shoulder, he could not evade the blows as they rained down. In seemingly no time at all, he was choking out sobs while hot tears of pain and humiliation ran down his face. He was reduced to abject pleading for mercy from the fire in his flesh. But his stepmother never slowed in her spanking. "Well Andrew," she taunted him, "you say you have learned your lesson, but I will be the judge of that. This will not stop until I am satisfied that you will never again touch my shoes without permission. But don't worry. I will make sure that permission is granted to you often. In fact, I will insist that you worship my foot-ware at all times. You will become the meekest, most obedient slave to my shoes that you can be." Finally, the beating ended with Andrew slumped helplessly across Kathleen's lap. As the blows against his buttocks ceased, he hoped his humiliation was over, but he soon found it was only just starting. Still wrenching his arm, Kathleen again caught his ear in a painful grip. Forcing him to rise, she marched him over to the mirrors covering the doors to her closet. Turning him to face away from the mirrors, she forced him to turn his head so he could see the reflection on his flaming butt cheeks. And flaming they were, as red as the setting sun and seemingly as hot as its surface. Already some of the redness was darkening to black and blue as Andrew contemplated his well-bruised behind. He again began to sob as he realized the pain he was feeling would not soon ease. Suddenly Andrew was propelled toward the foot of Kathleen's king-size bed. She forced him to sit on the edge, eliciting a howl from him as his ass cheeks made contact with the satin coverlet. Keeping the pressure on his earlobe, Kathleen reached down between the footboard and the mattress and pulled up a wide leather collar secured to each side of the bed by heavy golden chains. She quickly wrapped the collar around her helpless stepson's neck and buckled it securely. Hanging from a ring on the front of the collar was a small padlock, which she used to lock the strap on the collar so it could not be removed except with a key. Andrew found himself a prisoner chained to the foot of the bed. Looking both right and left, he saw that his chains were attached to heavy eyebolts driven into the stout bedposts. He tried to remove the tight fitting leather collar from around his neck, but the padlock prevented that. He could feel the chains were clipped to heavy D-rings on the side of the collar. A similar ring dangled in front, underneath his chin. He obviously was not going to be moving around unless he could drag the heavy bed with him. That did not seem likely, so he was a naked prisoner to his stepmother until she wanted to release him. As he looked up at her, she smiled in satisfaction as she read the defeat, pain and fear in his eyes. "Darling," she sneered at him, "You seem to be ready to start your training as my foot slave. Don't worry, it will not be too painful if you cooperate and I can assure you that you will have all the exposure to my shoes that you could possibly want. So why don't we begin? First though, I should tell you that your collar can only be unlocked by a key which is in safekeeping outside this room. So if you try to resist, you will only be harming the one person who can set you free. Then you would be trapped here quite a long time, since you could not summon any help, nor could you move very far due to the short length of your chains. I trust you see the hopelessness of your position without me. So let's not have any nonsense or disobedience, shall we?" With that Kathleen walked over to the nightstand, pulled out a multicolored handful of material and threw it on the bed. Andrew turned to see a pastel pile of nylon stockings near the foot of the bed. His stepmother then walked to the closet, looked down as though selecting something and then picked up a pair of white sandals. Andrew gave an involuntary shudder as he beheld these shoes, with their thin sole, three-inch heels and thin white straps at the toe, instep and ankle. Kathleen smirked as she knelt before her captive and grasped his foot to guide it into the sandal. She then tightly buckled the ankle strap so the shoe was secured. She repeated the process with his other foot and then stood up to admire her handiwork. "Well, dearie," she said, "such delicate shoes for your pretty feet. Those straps look so soft, thin and weak. They seem the essence of femininity, but like a woman, they are strong enough to hold you. I can assure you they will not come off. You are trapped in them until I allow you to take them off. And that will not be for some time. Now I have other shoes for you to wear, but obviously not on your feet." "Wha, uh, what do you mean?" Andrew managed to ask. But that only got him a swift slap in the face and a stern answer from Kathleen. "Silence, slave. You will only speak when I give you permission to due so. And then you will always respectfully address me as 'Mother.' After all, I am your parent and guardian until you are of age. So I am your mother in every sense except the biological one and what does that count for these days? As for my meaning, you don't have to worry. I will not leave you in any doubt about that. So let's proceed and remember, 'slaves must be seen and not heard.'" Kathleen returned to the closet and this time selected a pair of shiny black lace-up calf-length boots. Standing in front of her thoroughly cowed stepson, she placed the boots on the bed beside him and firmly ordered him to extend his right hand. When he hesitated, she reached out and grasped his hand, bending it back painfully against his wrist and pulling it toward her. She then reached out and took one of the boots off the bed. Maintaining her iron grip on his hand, she forced it into the boot, pushing it in until his fingers were jammed into the toe as far as they would go. She quickly released his arm and then pulled the laces of the boot as tightly as she could, starting at the bottom and proceeding to the top, were she tied them securely in a double knot. She then repeated the process with his left hand, although this time with his cooperation, sliding the boot easily onto his hand, pulling the laces taut and firmly knotting them. Andrew looked down at the bizarre display of his hands trapped in the boots. His fingers were jammed so snuggly in the toes of the boots that he could not move them at all. Similarly, his wrists were immobilized by the stiff leather and the tight lacing. He suspected that even were he to pull on the knots with his teeth, they would not be easy to loosen. He realized that without help he could not release his hands. Again, Kathleen had demonstrated the power of women's shoes to him. The light and seemingly fragile boots, the essence of femininity, were as strong and binding as handcuffs. Yet the feel of their smooth leather on his hands, wrists and forearms was strangely arousing. He looked down at his hands and feet in their feminine bondage and a feeling of complete helplessness washed throughout his body. But he could also feel an erotic thrill. His penis was red, erect and throbbing, reminding him how close to orgasm he had been before Kathleen had interrupted his masturbation. Glancing up at her he saw a wide smile of triumph on her face as she too realized how turned on he was by his shoe bondage. But Kathleen was not yet done with her new foot-slave. Turning to the closet, she picked up the red pumps he had been fondling and placed them on the bed beside the pile of nylon stockings. Grinning wickedly, she quickly took one of the nylons and tied a slip knot in the middle of it. She then reached down and seized Andrew's quivering penis and pulled it through the loop. She also pulled his cock and balls through it and then tightened it, causing his swollen testicles to bulge even further, while his penis became even harder with the tight knot restricting his circulation. Finally, she picked up one of the red pumps and holding it with the sole and heel toward her, slipped the shoe on her stepson's cock. She then wrapped the ends of the nylon around and around the shoe, trapping him inside it. She finished by tying a tight square knot in the stocking. The shoe now hung between his legs in an obscene display. Andrew realized that he could not untie the stocking with his useless hands stuffed in the boots. Neither could he touch or rub his cock, since it was secured inside the red pump. "There now, darling," Kathleen purred at him, "the loop should keep you from losing your erection, but you cannot touch yourself to bring yourself any sexual relief. Quite a dilemma, isn't it? But now, it seems we have one shoe left. What should we do with that? I know, open your mouth." Andrew again hesitated at that command and again he received a stinging slap on the cheek. He quickly opened his mouth in as wide a gape as he could manage while Kathleen took the other red pump and stuffed the toe into his mouth. This pressed the shoe against his face and his nose. He breathed in the powerful scent of leather and the acrid odor of Kathleen's foot. Even this seemed to increase his sexual tension as Kathleen proceeded to wind a stocking around his head several times and then secured the shoe in place with another tight knot in front of his face. He could barely see through the stocking and he was securely gagged by the toe of the shoe in his mouth. Every breath he took brought in the overpowering odor of leather and sweat and he had the taste of the leather in his mouth constantly. It was another demonstration of the power of the female shoe to overwhelm his senses. Kathleen stepped back to admire her work. She nodded in satisfaction at her stepson. With the shoes on his hands, face and genitals, he looked grotesque, but he was obviously aroused by the assault on all his senses except hearing. Taste, touch, smell and sight were receiving stimulation from his foot-ware bondage. Looking down at him in contempt as he sat on the edge of the bed before her, Kathleen felt triumphant. "You look lovely, darling. I'll just leave you alone for a while to enjoy your situation. I will be back later to continue your training. You will soon be the sweetest, most obedient foot slave in the world. Don't go away now. Not that you can, of course. Just think about all the shoes and boots you will have access to as my slave. As long as you do everything I say, that is." With that, she reached out to stroke his cheek. He flinched, expecting a slap. That brought a laugh from her. "I am glad to see you are afraid of me already. Just think about your spanking and what you can do to earn rewards, instead of punishment from me. I will still punish you whenever I want, but you might make things easier on yourself by always obeying me instantly." With that, she turned and walked out the door to the bedroom. Andrew heard a click as a deadbolt was turned to secure the door. That was another preparation Kathleen had made to control him. Now he was not only chained to the bed, but he was locked into the bedroom. All he could do was sit and bask in the sensations of the shoes Kathleen had secured to his body. Three hours later Andrew remained a prisoner in his stepmother's bedroom. He had discovered his chains were too short to allow him to stand upright. All he could do was sit on the edge of the bed, lie back on it with his legs dangling, or kneel on the floor in front of it. With his hands confined inside their boots, he could not unclip his chains from his collar, nor could he untie the stockings holding the shoe stuffing his mouth. For the same reason, his genitals remained trapped inside the red pump. All in all, he was thoroughly miserable, from his aching jaws to his burning bottom, to his feet in their unaccustomed stiff, narrow high heels. But the worst part of his ordeal was the isolation. As all prisoners do, he was discovering that his fear that his captor would never return was worse than the fear of her coming back to torment him again. Either way he could not stop thinking about Kathleen and what she had in store for him. She was fast becoming an obsession and his anxiety was constantly rising. In short, he was becoming vulnerable to her manipulations. Like many prisoners, his own thoughts were breaking his will more than any torture could have. At last Andrew heard the lock in the bedroom door click. The door opened and Kathleen entered pushing a serving cart with her left hand. In her right, she gripped a springy black whip, about three feet long and with a leather lash on its end. Andrew felt his heart begin to race at the sight of it. Stopping with the cart near the side of the bed, she looked down on him with a broad smile of contempt on her face. "Well, dear," she said with a sneer, "I think it is time to start your training. I hope you have been considering the consequences of disobeying me, so that we will not have any disturbing incidents while you are learning to be a perfect foot-slave. But if you deserve it, you can be sure this whip will bite. So it will be much easier all around if you just do as you're told from the start. So let's begin. First of all, whenever I enter this room, you will immediately kneel on the floor by the bed. You will bend forward from the waist and place the shoe on your face flat on the floor, so the sole and heel are placed the same way they would be if the shoe were on your foot. Then you will place your hands beside your head. This is to show your Mistress how you desire to place yourself in a vulnerable position to please her. You will remain kneeling like that until I give you the command 'sit.' At that point you may sit on the edge of the bed with your feet flat on the floor, legs together, hands crossed in your lap and your head bowed submissively... Again you will not move without permission. Finally, if I give the order 'lie back,' you will lay your upper body back on the bed, with your hands beside your head and your legs spread widely apart. You will look straight up at the ceiling, never at me. Do you understand?" At his nod, Kathleen's whip stuck like a snake, sharply stinging his arm. "Well, you idiot, if you understand, why aren't you already kneeling? I told you that would be the first position to assume whenever I enter the room. So move it!" Andrew had barely begun to move when he felt the bite of the whip again, this time on his bare thigh. Frantically, he almost dived to the floor. He placed the shoe gag as flat on the floor as he could, but Kathleen was not satisfied. She pushed the back of his head down with her own high-heeled shoe. The pressure was so great that Andrew could barely breathe. Just as he thought he would pass out, she eased the force just enough to let him gasp in some air. "When I come through that door, darling, you had better be in this position before I take one step into the room. Do you understand?" Andrew could only grunt in assent, but his Mistress did remove her shoe from his head. He gulped in deep breaths of air, but otherwise did not move. He heard nothing for a long time, but he knew Kathleen was towering over him and contemplating her power. After what seemed an age, she spoke. "Well, dear, perhaps you are not totally worthless after all. But we shall see. We will practice all three positions for a while to see how long before you catch on. If you are a slow learner, then so much the better for me and the worse for you. My whip will get quite a workout in that case. Shall we begin? Sit!" Andrew scrambled up onto the bed as fast as he could. But still fell short of Kathleen's expectations when he didn't put his legs together tight enough. It was hard to do that with the shoe dangling between them, but with some practice, he learned to do it acceptably. That was followed by practicing the command "lie back" until that position was perfect. But if Andrew thought Kathleen would be satisfied, he was badly mistaken. For she began shouting the orders at him in rapid succession. Andrew had to practically throw himself from lying on the bed, to sitting, to kneeling. He was soon gasping for breath, since he could not breathe easily through his shoe gag. And the whip seemed to be constantly flicking out to torture him, while his Mistress yelled out the commands like a drill sergeant. Finally, though, he was left sitting on the edge of the bed, panting and feeling like bees had been stinging him all over. Kathleen said nothing as she let him rest there. Finally she reached over to the cart she had pushed into the room and lifted a heavy gold chain, like the ones shackling him to the bed, from it. This chain had a single padlock on the end, which she used to attach it to a ring on the front of his collar. Then she unclipped the side chains from his collar. Andrew was now free from the bed, but he was leashed like a pet, ready to respond to more commands from his Mistress. He now learned a new command, "arise," which meant to stand straight up, heels and legs together, hands at his sides and his head bowed submissively. This was followed by a sharp tug on his leash along with the order "come." Kathleen had no need to explain what that meant as she led him toward the bathroom adjoining her bedroom. Andrew stumbled along behind her, clumsy in his unaccustomed high heels. But he managed to walk into the bathroom without falling, as Kathleen led him up to the toilet. Turning to face him, she addressed him with humiliating words. "Well, slave, since you don't have the use of your hands, it would seem that you will not be able to do the simplest tasks without my help. So it looks like I will be pottie training you for some time. At least you will now learn the correct way to do your business, sitting down, as a proper slave should. So let's begin." With that, she reached down and untied the knot in the nylon stocking trapping his penis inside its shoe covering. She unwrapped the shoe and slipped his penis free, but she did not remove the stocking from the base of his genitals. She simply held the loose ends in her hands and directed him to sit on the toilet. He complied quickly, but when she told him to urinate, he was so embarrassed and humiliated, he couldn't. She told him she could wait all day if necessary and finally, he was able to "tinkle," as she referred to it. When he was done, she took a piece of tissue from the roll and carefully wiped his penis dry. Andrew felt his face burning with embarrassment at this new humiliation, but he was quite helpless to stop her. She then ordered him to rise and soon she had re-secured his penis inside its shoe covering. "Time for din-din," she announced as she led him back into the bedroom. Andrew felt a gleam of hope that his hands would be freed to allow him to eat, but his hopes soon disappeared as Kathleen spread a sheet of newspaper on the floor and placed two bowls from the serving cart on it. Andrew could see that one bowl contained what appeared to be beef broth, a steaming clear brown liquid, while the other was about half- full of what seemed to be water. Kathleen now untied the shoe gag from around his head and Andrew felt great relief in his aching jaw. But he knew better than to say anything. But Kathleen did not intend to grant him any further freedom. "Oh, dear," she said with mock concern. "It looks like your hands are still useless to you. I guess you will just have to get down on your hands and knees and drink your broth and water like a dog. Since you are now my pet as well as my slave, you should get used to acting like one. So why don't you get started." Andrew could see his only choice was to comply or go hungry, so he carefully got down on all fours, crawled up to the bowls and started to lap the liquids. The broth was bland and needed salt and the water was lukewarm, but he was hungry and tried to drain both bowls. Mostly he succeeded in making a mess of his face and the newspaper, since his unpracticed attempts to eat this way spilled more than he ended up swallowing, but eventually he seemed to fill his stomach. Obviously, by eating this way gaining weight would not be a problem. Finally he finished and Kathleen allowed him to lift his face so she could wipe it with a white cloth napkin. Ordering him to stand, she replaced the bowls on the cart, crumpling the newspaper into one of them as she did so. Andrew hoped she would not gag him again, but his hopes were dashed as she quickly forced the pump into his mouth and tied it in place with the stocking. Kathleen was determined to keep him constantly aware of the power of the shoes to control his behavior. They were to become an extension of her authority and dominion over him. "Now darling, wasn't that nice? That's going to be your diet while you are in training. So you won't have to worry about losing your girlish figure, will you? Now we have the rest of the afternoon left, so I think we will start practicing your pretty feminine walk. Since you will only be wearing the finest in ladies' footwear from now on, it's only right that you be able to walk gracefully in your high-heeled boots, shoes and sandals. Right now you're wearing three-inch heels, which will be the minimum height from now on. There is just one more thing we have to do to ensure your steps are always short and mincing like a real woman's." With that, she again turned to the cart and picked up a thin gold chain. At her command to "sit," Andrew perched on the edge of the bed as he had been trained. Kneeling down, Kathleen attached clips on the ends of the chain to his ankle straps. She then arose and ordered him to stand. Pulling his leash, she directed him to the side of the bed, where there was a large open, area in front of the room's windows. She had him walk around her in a circle, as though he were a horse being trained to pace. She constantly reminded him to stand straight, hold his chin up and point his toes outward as he walked. He had to take small steps due to the confining ankle chain and he soon learned to move his hips from side-to-side with each stride. Kathleen was constantly pointing out flaws in the femininity of his walk and her whip often stung him when he did not comply fast enough with her instructions. Andrew soon grew tired at the unaccustomed exercise, but he could make no verbal protests at all. Kathleen kept him at it for two hours, with only one five-minute break. Finally, she allowed that he might be getting the hang of it and she concluded the lesson. Andrew was drooping with fatigue and breathing as deeply as he could with the shoe wedged in his mouth. He hoped Kathleen did not have any other torments planned and in this he was fortunate, as she led him back to the bed, clipped his chains to his collar and unlocked his leash. "Now, pet, you can rest for a while. I know you won't do anything foolish, will you? But then, you seem to be somewhat confined at the moment. I will let you enjoy my shoes until dinnertime. You can think about how feminine you will be as your training progresses. Until then, my sweet little foot-slave, keep thinking of the many ways you will be able to please your Mistress." Giving him a pat on the head, she left the room, pushing the cart before her. Once again Andrew heard the click of the lock and knew himself to be completely helpless and at the mercy of his stepmother. He knew that his obsession with shoes had led him to be discovered by her and he also knew she was determined to use that obsession to control him forever. He was literally trapped in shoes, but the feelings they aroused were so overpowering, that he was powerless to resist. He knew he was already a willing slave to women's foot-ware. Hours later Andrew was kneeling on the bed between the wide spread legs of his stepmother. He was free of his shoe gag, but only so he could use his mouth to thoroughly lap Kathleen's cunt. He was laboring to please her, since she still had her whip and Andrew knew she was only too willing to use it on him if he displeased her. He was also still chained, but this time to the head of the bed. Andrew had had a long, hard day. At dinnertime, Kathleen had again freed him long enough for him to relieve himself in the bathroom and to eat another meal doggie- style, from two bowls on the floor. Then she had left him alone again until now. It was late in the evening and she was again training him, this time to give her oral sex. She had been giving him verbal directions and he had seemed to learn quickly, because she was now silent except for sighs of contentment. Finally she gave a loud moan, pushed his head firmly into her pussy and became extremely wet. Andrew lapped at her fluids as she directed him so as not to miss a drop. Kathleen released the pressure on his head and sank back on the bed, totally satiated. She beamed at the abject slave kneeling between her legs. She knew she had captured him through his foot fetish and she intended to maintain her ownership over him forever. But this was only his first day of training. She intended to maintain her absolute control for at least another two weeks, until Andrew was completely broken in. Yes, she thought with a satisfied smile, until he was broken in like a new pair of shoes, smooth, soft and compliant. Always at hand for her use. She had many plans for the next two weeks. She had already pointed out to him the thin mat on the floor beside her bed where he would spend the night after being dismissed from his duties in her bed. He would lie there each night, chained to the headboard and still wearing her shoes on his feet, hands and genitals. She would not require him to be gagged at night, unless he needed extra punishment for not pleasing her sexually. That would give him plenty of incentive to make her cum again and again. If he needed to answer a call of nature during the night, she would have to unlock his chain and help him to the bathroom as she did during the day. But that would just give her more chances to humiliate him, so she did not think he would be awakening her very much. During the days he would be confined to the bedroom, of course and she would see to it he got lots of practice in walking in high heels, as well as in other areas of feminine deportment. And best of all, at noon every day, she would take him across her lap for a quite long, painful spanking on his bare bottom with a shoe or slipper. She shivered in anticipation. And after that, who could say? She might ease up on his instruction in slavery, but she knew he would come to love the pain and humiliation as much as he feared it. He would be hers forever, unable to even think about escaping his Mistress. Two weeks later Andrew was still in his position at the end of the bed. It was late in the evening and he was simply awaiting Kathleen's return. She had not told him this was to be a special day and he had spent it as he had all the others since his enslavement. His Mistress had awakened him and taken him to the bathroom for his morning cleaning. After allowing him to relieve himself, she had stripped him of everything except his locked collar and chain leash, which she had used to secure him to a towel bar while she bathed him like a young child. She scrubbed him thoroughly, giving special attention to his ass, cock and balls with the soapy washcloth. Even though this aroused him terribly, she had not allowed him any sexual release. In that today was like any other day of the last weeks. After drying him, she shaved his face and even brushed his teeth for him. He was treated as a helpless little baby in the bathroom at all times. These feelings of infancy were augmented by the complete hairlessness of his body from the neck down. Kathleen had had plenty of time to remove all his body hair, even the hair covering his genitals. She had left him with only a triangle of hair just above his penis, like a woman's pubic patch. She had taunted him that since he liked women's shoes so much, he should try to emulate the female in all ways. Another way in which to shame and degrade him. She then led him back to the bedroom, where she wrapped a tight black waist cinch around him and fastened it tightly with the many hooks in front. Andrew had to breathe in as much as he could and stand up as straight as possible to narrow his waist enough for the garment to fit him. But Katherine showed not a sign of pity for him as she hooked the front together from top to bottom. She then directed him to smooth a pair of smoky gray seamed nylons up his legs and attach them to the four garter straps dangling from the waist cinch. He meekly complied with motions he had been practicing under her guidance for the last two weeks. He nearly fainted with desire when he saw the boots she brought out to place on his feet. They were mirror bright black boots that extended to just below his knees. They were laced boots and Kathleen carefully pulled the laces taut all the way to the top and knotted them tightly. These boots also had two-inch platform soles and wicked six- inch heels. Andrew and his Mistress both knew that he would be able to walk quite well in these extreme boots due to the instruction and practice he had received in the last weeks. For his hands, Kathleen selected black suede ankle boots with side zippers and stiletto heels. She forced his hands into them and then to insure he could not remove them, she wrapped wide black tape around the tops and up unto his wrists. Finally, she selected a gleaming black Mary Jane style shoe with a single strap across the instep and forced his long, hard cock into it. As usual, a nylon stocking was looped around the base of his cock and balls, then wrapped around the shoe, imprisoning him inside it. It dangled lewdly between his legs, the heel sticking outward to direct attention toward his trapped and helpless genitals. With that the foot-slave was ready to get down on his hands and knees and eat his breakfast like a pet from two bowls on the floor. After his meal Andrew had been gagged with the twin shoe to the one he wore just below his tuft of pubic hair. The rest of the day had passed as all the other days of Andrew's enslavement had, including his hard, bare-bottomed spanking at noon. Now he simply waited for his Mistress, seated on the end of the bed with his legs in their ebon boots crossed demurely in front of him. This was another feminine posture he had been instructed in by his dominant stepmother. She was being quite thorough in feminizing him as well as reinforcing his foot fetish. Suddenly he heard the door start to open and instantly he was on his knees on the floor, an instinctive reaction to present himself as his Mistress wished him to. Unchaining him from the foot of the bed, Kathleen ordered him onto it, on his hands and knees facing the head. He wasted no time complying and she then attached the chain from that end of the bed to his collar. For a long time after that, nothing happened. Andrew knew Kathleen was looking down at him, but she said not a word, so he did not move a muscle. Even though the silence stretched for what seemed like hours, he knew that only when she commanded him could he move without being punished. Finally Kathleen spoke. "Tonight you have been a slave for two weeks and even though your training is nowhere near complete, you have pleased me by your desire to obey me and quickly learn your new role in life. Starting tomorrow, you will no longer be confined to this room. In fact, you will learn to be my male maid, so you will need access to the whole house as you learn your duties. And your movements will not be confined as completely as they are now. After all, you will need the use of your hands, won't you? But I definitely love to see you sucking on the toe of a shoe like the one in your mouth right now, so get used to it. For you, talking is permitted only when I speak to you first, so a shoe gag will help you remember that. Then there is the matter of your dress. If I approved of your progress, you will be allowed to wear more garments until you are fully uniformed as a maid. Part of your training will include makeup application, hair styling and speaking (when permitted) in a feminine voice. So you are going to be a busy little girl. But don't worry, I will instruct and guide you every step of the way. As rewards for good behavior, you will even be granted access to your favorite foot-ware, just as you are now. Right now, though, I will discontinue your daily spankings. But you will still be punished for any infractions of my rules. So you can see, you have a lot to look forward to, my pretty little foot-servant. Now I do think you deserve some reward for the last two weeks, so spread those smooth sexy legs nice and wide for your Mistress!" With that, Kathleen reached between her slave's legs, pulled his shoe- encased penis roughly back with one hand and untied the nylon wrapping with the other. Discarding the nylon, she held his cock firmly with her right hand. She began to stroke it with her fingers and thumb and was gratified to feel it grow in her hand, becoming even harder and hotter. The shoe she held in her left hand, its toe near the head of her slave's defenseless cock. While manipulating him, she began to taunt him. "It has been a long time since you've cum, hasn't it, slave? Well, I am going to bring you off now and all your sweet juice will be caught in the shoe I am holding. Then we will repeat the procedure, darling, until I decide you have been thoroughly drained. After the first couple of times, you might start to slow in your reactions, but don't worry. I have all night to make you cum again and again. After awhile you might not like it so much, but that hardly matters, does it? No, only your Mistress's desires are important to you now, so we will continue until I am satisfied that you have no more love juice to give. And every drop will be contained in this beautiful shoe you love so much. Then, I will remove your shoe gag and make you drink all your nectar. I will love holding the vessel above your wide-open mouth and pouring it in a thick stream into you while you swallow every drop. Then you will lick the inside of the shoe thoroughly so as not to waste any liquid at all. Umm, how you will learn to love the taste of your own sperm. After that, you might be a bit tired, but I will still require you to pleasure me with that sweet mouth of yours before I dismiss you for the night. Oh look, dear, you're starting already!" It was true, for Andrew was making humping motions against his Mistress's hand as his cum boiled out from deep in his balls. He could feel the jet passing through each millimeter of his penis as Kathleen firmly held him and guided the stream into the shoe she held. Afterwards Andrew's head slumped and he gulped huge breaths as his body felt completely spent as though he had just run a marathon. But Kathleen never slowed at all in her manipulation of his organ. She massaged his balls as well as his cock and Andrew could feel himself getting hard again within just a few minutes. It was obvious his Mistress intended to milk him repeatedly. Sarah smiled a broad smile of triumph as she felt her slave's reawakening cock in her hand. Andrew groaned as he realized his owner and Mistress intended to keep her word. For her abject slave, it was going to be a long night. THE END

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One Shoe GumshoeChapter 4 Up in the Air

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One Shoe GumshoeChapter 5 Down to Earth

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One Shoe GumshoeChapter 6 A Pompous Penguin

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One Shoe GumshoeChapter 8 To Dance to Reality

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One Shoe GumshoeChapter 9 Life Before Mary

“I JOINED the Metropolitan Police as a temporary officer helping typing up policeman’s reports, bagging and processing Crown evidence,” I said to Mary after the all-clear sirens had sounded and guests were permitted to return to their rooms or suites for the remainder of the night. We had changed into our bed wear and donned respectable dressing gowns supplied to the suite and resting in her sitting room. Mary was curled up with her legs comfortably tucked under her on a chaise langue, and I...

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One Shoe GumshoeChapter 10 Mortlake Mystery

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One Shoe GumshoeChapter 11 77 Denmark Hill

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One Shoe GumshoeChapter 12 Number 77

THEY welcomed us with open arms at the estate agents. I assumed that houses and flats were hard to shift with so much uncertainty about the future and the war going against the allies quite so badly. Also, all the breadwinners of new or growing families were being conscripted, so there were fewer opportunities for families to obtain mortgages from banks or building societies. Although the bombing had caused homelessness elsewhere, the war had bypassed this little corner. We had peered...

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One Shoe GumshoeChapter 13 Breaking and Entering

OUTSIDE the estate agents’ premises I gently took Mary’s arm, fearful that she might faint. She looked close to tears. “Do you want to sit down? There’s a tea shop open over there.” She shook her head, but seemed unable to speak. “Do you still want to go to the shop and try and look at the flat next door?” She nodded. We were there in a minute or so and the mainly glass door covered in whitewash opened quickly using the key and I pushed her inside. As soon as I closed the door behind us...

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One Shoe GumshoeChapter 14 Encounter With Curly Cavenagh

MARY sat down on Gold’s bed with me to survey what we had collected from our survey of the two-and-a-half floors of the flat, it really wasn’t much at all. There was an empty trunk and two suitcases in the unfurnished bedroom up in what was once the loft; they were locked but I opened them and they were indeed empty. All we had gathered was the framed photo, of course, a diary, a pair of reading glasses and an unmarked cigarette lighter that Mary thought she recognised. “If you think I look...

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Shoe Salesman Chapter 2

It had been a couple of weeks since the sexy shoe sale and Jim was getting horny thinking about sex with that older woman. He was at the store when she came in and sat down. “Jim I need some shoes. I want you to pick out the sexiest pair you can.” “Oh, okay. How about some really high heels?” “Sure if you think they are sexy.” He went in back and got out a pair of 5” black stilettos with ankle straps. The sort of shoe you call “fuck me”shoes. “Here lets see how they fit.” He took...

4 years ago
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The Shoe Salesman and the Hot Mom

All good. Her dark eyes were hot today, her pony tail of her dark hair was tight and taut, revealing the glowing bright and soft skin of her neck. She looked down at her little skirt and tried to pull it over her knee a little more. It didn’t make any difference. She’s not used to wearing such a short skirt. Looking beyond her knees, she saw her bare legs and wondered if she should have worn an open-toe set of heels instead of the white heels with the covered, blunt nose that she wore...

3 years ago
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Patriciyas shoe story

Being a shoe fetishist I came across a sissy named Patriciya, full time trans and a little shoe hoarder. When we first met and she opened her closet, aka shoe vaultthe look and smell of used stripper heels made me hard and I made her my sissy shoe bitch. She was inexperienced, but willing to experiment, which I found hot andhotter yet, she was into heels and boots almost as much as me. I made her send me sexy pics while I was at work and even made her wear heels and a chastity during a drink...

3 years ago
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35 Year Old Mom Is Seduced By The Young Shoe Clerk

“I really need new shoes? These are falling totally apart.” I told my husband.“Why don’t you go looked for some new ones?” he said.“You are right! I hadn’t bought a new pair of shoes in two years. It is very hard to teach my aerobics class with this pair.” I said.I had the day off so I decided to go to the mall to look for some new shoes. I had figured their was several shoe stores in the mall and I was sure I would find a pair. I put on my summer dress since it was a very hot day outside and...

Quickie Sex
4 years ago
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Uther

Uther By Ellie Dauber (c) 2006 Introduction According to the legends of King Arthur, Merlin changed Uther Pendragon into a double for Duke Gorlois, so he could spend the night with Ygraine, the Duke's wife. Ygraine and Gorlois had three daughters: Elaine, Morgause, and Morgan le Faye. During their time together, Ygraine became pregnant with the child who was to become King Arthur. Uther's men killed Gorlois that same night. This is my TG (of course) version of what...

3 years ago
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Melissa Shoe Store Owner

Melissa: Shoe Store Owner I've been stuck in my boy clothes all week, working long hours. But I have also been planning my weekend excursion. I have found out about a shoe store in a mall across town that carries large sizes. I have been looking forward all week to Saturday to turn Melissa loose. I had to work Saturday as well, but I made my escape by 3. Home, shower and shave my legs and face. Already I felt like a new woman. First I painted my toenails a bright red. Then I pulled...

2 years ago
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One Two Buckle My Shoe

….one two buckle my shoe…. Bowed and bent, in constant genuflection before women, was not a man's naturalstate. Having spent so much of the day compressed like a caryatid, his back bentor buckled, so often on his knees as he forced fat feet into shoes which womenwould insist on having a size too small, Steve felt like some kind of PrinceCharming... but with only ugly sisters to attend to. His back ached through having to bow low over these vain obese women, hislegs were stiff from his...

2 years ago
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Shoe shopping with Mom

Shoe Shopping with MomSue, 43 years, housewife and motherMary, 69 years, pensioner, mother, grandmotherIt was a hot summer day in july and Sue gets visited by her mom. It was at the end of the month, and Sue was a little bit pissed off,because it was summer and hot outside, but she didn’t have some money to buy open shoes that she wanted all the time.She told her mom that she would like to have some flat and open shoes but that she don’t have the money.Her mom deiced, to go with her to the city...

3 years ago
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Shoe shopping with Mom

Shoe Shopping with MomSue, 43 years, housewife and motherMary, 69 years, pensioner, mother, grandmotherIt was a hot summer day in july and Sue gets visited by her mom. It was at the end of the month, and Sue was a little bit pissed off,because it was summer and hot outside, but she didn’t have some money to buy open shoes that she wanted all the time.She told her mom that she would like to have some flat and open shoes but that she don’t have the money.Her mom deiced, to go with her to the city...

4 years ago
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Aunt Cassies Taboo Urges Vol I Aunt Cassies Shoe

I reached my hand down under the covers, finding a wet spot right where the blanket had been lying against me. I ran a finger through my slit, pulling out a small, sticky white glob. Bryan stirred next to me on the bed, and I briefly considered rousing him for round two, though I ultimately decided against it and committed instead to double-clicking my own mouse. Still, my thoughts still drifted to the young man who was lying asleep next to me. I thought of the way his fingers squeezed my...

2 years ago
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Carruthers Bride

The the wind howled around the quayside as I stepped onto terra firma for the first time in weeks, the wind threw sharp shards of ice to sting our faces as we looked up at the sails as they were finally furled and stowed as our captain grinned at our discomfiture, "Au revoir!" he joked as if he knew we should soon be recalled. Those such as were left, and we were few enough, I shuddered. My best uniform packed securely in my Valise, awaited me, and just a few more duties before I...

3 years ago
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Kryssi the Bimbo Watches Porn and Goes Shoe Shopping

Hiya everyone, did you miss me? Like, so much has happened in the past few weeks that my head is buzzing. Before you worry, Matt and I are, like, totally OK; and people still think I’m that Bimbo Baggins character. But so many cool and fun things have happened to me that if I don’t talk about it I’ll explode.To start with my old boss at the restaurant told me that he couldn’t let me work there anymore. I had no idea that his wife was his boss! You see, what had happened was that I was going...

Exhibitionism
3 years ago
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The shoe store

She was starting a new job Monday and was very excited. She would no longer be a waitress for minimum wage and her college education was finally going to pay off. Her new company gave her a bonus for signing on with them and she had spent it on a new wardrobe for work.She only had one more stop and that was to buy new shoes for work. The company was very specific that skirts and high heels were mandatory for all managers. She was going to be a manager, high heels would be fine with her.She...

1 year ago
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Motherless Vintage

Do you know of the porn site Motherless.com? You should. I’ve reviewed it a few times on my site, The Porn Dude, although it was for different genres every time. This time around, I’m going back to this place and looking at a specific and niche little category many of you are just begging me to cover. We’re looking at vintage porn today. While it doesn’t have the same resolution and quality as the porn you can find today, it’s definitely a genre of porn that has a lot of personality to it and...

Vintage Porn Sites
3 years ago
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Althea

I should have known better. I should have remembered that old saying, "If it looks too good to be true, it is." I was in love. She was damned near all I thought about with the exception of my studies and it didn't make sense to me. I prided myself on my intellect and my ability to think logically, but there wasn't anything logical about the way I felt about Althea. She was beautiful, smart and very popular and I was not. I wasn't a bed looking guy, but I was nothing exceptional. I was...

4 years ago
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SHOE STORE SEXPERIENCESs

SHOE STORE SEXPERIENCE-my firstAfter graduating from a rural High School, I worked for my uncle at his shoe store in the city. I needed a summer job to pay for university so it was an ideal fit. Since I was 18, and not a minor, he could leave the store for me to run. He liked to golf and if it was a nice day, he would leave when the urge hit him and I would not see him until the next day. I enjoyed working in the store. It wasn't so much the selling of shoes that got me all hard and excited as...

1 year ago
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Motherless Images

Motherless. A one-word website title that says everything it needs to say. This is a site where the rules are, more or less, completely thrown out the window, morality means absolutely nothing, and there is nobody to save you from it. Hedonism is God here.The site likely is also called this due to the fact that the girls who end up on motherless.com likely have no positive female influence in their lives to keep them from it. Motherless is the place parents spend their whole lives fearing that...

Porn Pictures Sites
1 year ago
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Motherless Amateur

I always considered Motherless the “4chan” of porn. Not only because Motherless was somewhat popularized there, but because Motherless also encourages users to share their own content in a very open way. This means minimal bullshit like moderation and censorship, and a strong “anything goes” attitude that leads to free and extreme content. It encourages people to create and upload their own homegrown content, like videos of their girlfriend pissing or spycam videos of their cousin....

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