The day Joe had long dreaded had finally arrived. His grandmother, the family matriarch who had ruled everyone around her with an iron fist, had passed on, and Karen, the woman who had been hired as his grandmother's paid companion, would be leaving. Joe had always been shy and hapless when it came to women, and now he was facing a lifetime of loneliness in the big house that he knew would now be his.
As he sat in his grandfather's old chair and listened to Karen moving around upstairs, Joe remembered when he had first met her. His grandmother had given him the task of finding her a companion, and Joe had interviewed nearly a dozen young women who seemed perfectly acceptable to him, only to have his grandmother rudely reject them without any explanation.
When Karen had showed up for an interview, Joe had expected his grandmother to send her away as well. Her references were highly suspect, and when he asked her about them, she had simply given him a little smile, leaned in towards him and said, "Maybe I should talk to your grandmother." Joe knew a dominant woman when he saw one and was sure that the two women would clash. To his surprise they had hit if off immediately.
Although the job of paid companion included cooking meals and doing light housework, Joe was soon dismissed to cook them lunch and then clean the house. In the days that followed, Joe would often be upstairs dusting or polishing furniture and hear the sounds of his grandmother's voice, raspy with age, followed by the delightful sound of Karen's laughter bubbling up the stairs. Karen was soon ordering him around as well, and when he passed through the living room on the way to the kitchen, Joe could feel her eyes on him, and he knew that she saw right through him.
Joe was abruptly brought out his reverie by a sharp pain in his right ear. He was startled to realize that Karen had come down the stairs without his realizing it and was standing right next to him. She had flicked her finger against his ear rather sharply to get his attention. "I see you're daydreaming again," Karen said, "I suppose you're going to be pretty useless without a woman to tell you what to do."
Karen was standing right next to him, and Joe started blushing. Karen just laughed and told him to follow her. "I'll give you something to keep you occupied for a little while."
He followed her downstairs to the laundry room, noticing that she was carrying a pillowcase full of dirty clothes in her hand. Joe had been doing most of the laundry, but Karen had always washed her own clothes and left her panties and stockings hanging up to dry from the several lengths of clothesline that were strung across the basement room.
Joe had been fascinated by her lingerie and the way that he couldn't help but brush against her underwear to get to the washing machine and dryer. He had soon started feeling them and rubbing them against his face, but she kept the dirty clothes in a hamper in her room, so he had never smelled her scent on them.
He had really wanted to try on a pair of her panties but was terrified that she'd find out and tell his grandmother, so he had secretly taken a pair and hidden them in one of his drawers shortly after his grandmother had passed away. He had been planning on wearing them while he jerked off after Karen had left.
Karen led him over to the corner of the basement and dumped out her dirty panties on top of the dryer. "I want you to wash these for me, and if you do a good job, I might just stick around for awhile and give you some more things to do," she said.
Joe started right for the washing machine to open it, but she grabbed the waistband of his gym shorts and yanked him back over to the dryer. "You'll wash these by hand, one at a time," she said, grabbing a plastic washtub and putting it in the laundry room sink. She added some soap and water and told him to get started.
Joe took a pair of bikini panties from the top of the pile and briefly stared at them before putting them into the washtub. He heard Karen's laughter behind him. "Fascinating aren't they?' she said. "I bet you've been fondling the clean underwear that I've left hanging down here to dry."
Unable to control his embarrassment, Joe blushed furiously as Karen enjoyed his discomfort. She moved around behind him and, reaching around him, took his hands in hers and plunged them into the soapy water. "This is how you are going to wash my panties from now on," she whispered in his ear as she moved his hands in the washtub.
The feeling of her hands over his and her body so close started to get Joe aroused. He started to pull his hands out of the water, but Karen pushed them back in and shoved him tight up against the sink. "You're not going anywhere until you finish your job," she said.
He could feel her breasts on his back and her hips grinding him against the sink. He started to moan and closed his eyes as his dick became fully erect inside his shorts.
As Joe started to instinctively hump the sink Karen took her hands out of the water, dried them on the back of Joe's t-shirt and reached over and took a pair of her panties off the pile of dirty clothes. When Joe started to moan again, she hooked a finger inside his cheek and pulled hard with one hand while she stuffed the dirty panties into his cheek with her other hand. Working quickly, she grabbed another pair and did the other cheek. She had no intention of letting him cum anytime soon, so she took a half step back and brought her knee up sharply between his legs, crushing his balls.
Joe went down like a sack of dirty laundry himself, smacking his chin on the lip of the sink in the process. Karen grabbed him by his hair and hauled him back up, ordering him to get back to work washing her panties. While Joe resumed his job despite the agony in his testicles and the pain in his chin, she went over to the workbench and snagged a roll of black electrical tape and used it to secure the panties in his mouth by wrapping the tape around his head.
With the panty gag firmly in place Karen stood behind Joe and stepped out of her high heels, kicking them aside. Joe started to turn at the sound, but she delivered a sharp smack to the side of his head and said, "Don't you dare take your eyes off your work!" Joe heard the unmistakable sound of a belt buckle being undone and realized she was taking off the skintight jeans she was wearing.
Joe was just starting to get excited at the thought that he might actually get laid for once in his life when Karen stepped up behind him again, reached around his head with her left hand and jammed another pair of panties up against his nose. "These aren't from the hamper little man." she said. "These are fresh from my body."
Joe inhaled so deeply through his nose that her scent made him dizzy. He could feel the warmth of her body still on the panties as Karen pressed them tight against his nose with her left hand and, with her right hand on the back of his head, began to smother him.
Karen kept her underwear tight against his nose until he began to panic and then eased up just enough to let him breathe through her panties, repeating the process several times. The underwear in his mouth had become soaked in his saliva by now, and he was tasting her and breathing her in at the same time. Joe thought he had reached the height of ecstasy, but now Karen took her right hand off the back of his head, reached into his shorts and began stroking him to the edge of an orgasm.
Just when Joe felt like he was going to explode, Karen stopped stroking him, reached down and grabbed the hair on his balls, pulling hard. "Oh no you don't," she said, "you don't cum anymore without my permission."
She began to alternate between stroking him and punishing him, bringing him to the edge every time and then pulling back and flicking her finger sharply against his balls or yanking on his pubic hair.
By the time Karen grew bored with torturing him his dick was slick with precum as was her hand. She dropped the panties that she had been holding over his nose the whole time and removed his gag. She made him lick her fingers clean and told him to get back to work. "I want those panties cleaned, rinsed and hanging up to dry when I come back down here," she said, gathering up her shoes and pants and heading for the stairs.
Joe managed to sneak a look at her naked ass as she was walking away. Without even turning her head, Karen seemed to sense that he was watching her. "Get back to work," she shouted, "and no jerking off!"
Joe worked quickly but carefully and was just hanging up the last of Karen's underwear when he heard her heels on the basement stairs. Turning around, he was amazed at her appearance. She had changed into a black leather miniskirt with a small matching top that showed off her considerable breasts. Her jet black hair, which had always been pulled back into a tight ponytail, was now flowing across her shoulders and she was wearing long, black leather boots that had sharp spikes for heels. He was so mesmerized by her transformation that he barely noticed the riding crop she held in one hand and the leather bag she was carrying in the other.
Karen dropped her bag and, crossing her arms, looked him over as if evaluating him for the first time. Under the weight of her stare Joe instinctively cast his eyes down to the floor, which seemed to earn him a slight murmur of approval from Karen.
"Now let's get something straight," she said. "If you don't wish to go any further, I will leave now and you will never see me again."
Karen knew damn well that that was the last thing that Joe wanted, but as he opened his mouth to answer her, she pointed the crop at him and told him to shut up. "If you want me to stay then you will strip naked, get on your knees and beg me not to leave," she said, pointing at the floor with her crop.
Joe shyness made him hesitate, but as Karen turned as if to leave, he pulled his t-shirt off, got out of his shorts and underpants and got down on his knees. As he started begging her to stay, she gave him a sharp crack with the riding crop. "If I stay, you will be my slave," Karen said, "and that means that you will address me only as Mistress Karen from now on."
Joe began to beg more properly and was instructed to clean his Mistress's boots. Joe seemed a bit at a loss as to how to clean her boots, so Mistress Karen said, "With your tongue you stupid shit!" She punctuated each word with a vicious crack of the whip and kept hitting him until he was groveling in front of her and licking her boots properly.
As Joe continued to lick her boots, Mistress Karen told him that the name Joe simply wouldn't do. "We'll need a proper slave name for you," she said. Looking down at his pale, naked body crouching in front of her, Mistress Karen noticed that all the hair on his body was as blond as the hair on his head. "I think I'll name you Teddy, since you look just like a little teddy bear," she said. With that she noticed that Joe was enjoying licking her boots a little too much, so she instructed him to stop worshipping them and to turn around facing away from her with his hands behind his back.
Joe heard the zipper on Mistress Karen's bag and then the clink of metal. He was tempted to turn his head, but he knew better by now. Mistress Karen quickly handcuffed his wrists and shackled his ankles. Joe heard her rummaging in her bag again and figured that she would be gagging him. Instead, Mistress Karen said, "Now Teddy, there's one more thing we need to clear up before we proceed." She walked around in front of him and displayed one last pair of panties.
Joe blushed scarlet at the sight of the underwear that he had stolen from her and hidden at the back of his own drawer. "Did you think I wouldn't miss them Teddy?" asked Mistress Karen. "Now tell me where you got them and don't fucking lie. I know you didn't take them off the line or I would have noticed right away." Embarrassed beyond belief, Joe admitted that he had gone into her drawer and stolen them while he was cleaning her room.
"Well I guess I'll have to teach you a lesson you won't ever forget," said Mistress Karen, "I can't have you going into MY personal space ever!" She hauled him to his feet and began pulling on his dick, forcing him to shuffle towards the workbench. Joe was so focused on not falling that he didn't immediately realize that she was leading him right into the vise that was attached to the edge of the table. Panicked, he tried to pull back, but Mistress Karen grabbed his balls with her other hand and pulled hard until she had his dick in the vise. Letting go of his balls but keeping a tight grip on the head of his dick she quickly spun the vise shut trapping his dick, tightening it more and more as his penis began to shrivel with fear.
With Joe's dick now securely caught in the vise, Mistress Karen went to work on his balls. She circled the thumb and forefinger of her left hand around his sack above the balls and began pulling down until his nuts were fully exposed. "You have no idea how made I am at you Teddy," she said as she grabbed some extra clothesline from the workbench and tied his nuts off.
Joe felt like his balls were being pulled off, and he watched in horror as Mistress Karen picked up an old wooden ruler from the bench. Bending it back as far it would go without breaking, she watched as is snapped forward into his swollen testicles with a satisfying smack. "They just don't make them like this anymore do they Teddy?" she said, as she proceeded to smack his balls over and over again. First she punished both balls at once, and then she began to angle the ruler so that she could focus on one testicle at a time. Joe had never been in such agony, and he begged her to stop.
To Joe's surprise she did. Releasing his squashed dick from the vise and untying his balls, she told him that he could stop whenever he wanted, but unless he let her finish punishing him, she would leave and never return. She gave him a safeword he could use if he really wanted to stop, but made it clear that stopping meant stopping for good. Joe's balls were still throbbing, but he couldn't bear the idea of her leaving, so he stood mute as she looked at him. "Good, we'll continue then," she said.
Leaving Joe still handcuffed and shackled in front of the workbench, Mistress Karen went back to her bag of goodies and pulled out some surgical gloves, lube and a shiny metal hook with a blunt point and a ring for attaching a rope at the other end. She brought them back to the bench and put them where Joe could see them. Snapping on the gloves, she said, "Now Teddy we're going to have to start getting your ass ready from my strapon, so I think we'll start by stretching it out a little bit." She lubed up her finger and, bending Joe over the workbench, began to work it into his anus.
Joe had never tried putting anything in his ass before, so he was entirely unfamiliar with the sensation. Although he tried to relax for his Mistress, his anus kept tightening up, and Mistress Karen decided he needed a little help. She put some lube on her other glove and started gently stroking his cock, which was just starting to recover from the vise. As Joe started to respond, she leaned over him and pressed her breasts into his back, murmuring into his ear that if he was a good slave he would experience things other people only dreamed about.
Joe finally relaxed and began to enjoy the sensation of her finger penetrating his ass while she stroked his cock. As his dick started to throb, he was sure she was finally going to let him cum as a reward for taking her finger. Mistress Karen had other ideas. She brought him right to the edge again before pulling back. Slipping her finger out she quickly grabbed the metal hook and began to slide the blunt end into his asshole. Joe felt the cold metal and clamped down involuntarily, so Mistress Karen began working on him again. It took a little longer with the metal hook, but eventually she worked it in while stroking him to the edge of an orgasm again.
As she left his dick throbbing with the need to let go, Mistress Karen fed a rope through the metal eye on the other end of the hook and then brought it up around his neck and pulled back sharply on both ends until Joe was standing up straight again. She kept tightening the rope until the hook was stretching his ass unless he arched his back. Then she tied the ends of the rope together making a loop from his neck down to the hook.
Joe couldn't really see what Mistress Karen was doing because he had to keep his back arched to minimize the pull on his asshole, but he heard the sound of the vise being spun open again. He assumed she was going to put his frustrated dick back in the vise and figured he could handle it a second time. It was only as she grabbed his dick in her right hand and the metal hook in her left hand, that he began to realize that she had something else in mind. Mistress Karen pulled him up on his toes and began maneuvering his balls into the vise.
Joe felt the cold steel on his scrotum as the vise spun shut. Mute with fear, he didn't think to use his safeword in time. Mistress Karen cranked the vise another turn and giggled as he screamed in pain and terror. Joe began to panic. Unable to pull out of the vise or come down off his toes, he started hyperventilating. Sensing that he might pass out, Mistress Karen let up a half turn on the vise and moved around behind Joe. Sliding her boots under his heels, she allowed him to rest for a moment.
"I've always wanted to have a man's balls in a vise Teddy," Mistress Karen cooed in his ear. "You're pleasing me very much," she said. Karen could see that he responded to her words of encouragement. As soon as his breathing returned to normal, she cranked the vise a full turn and step aside to watch. Joe let out a scream and started to pitch forward involuntarily, but the pain from the hook in his ass pulled him back Forgetting that Mistress Karen's boots were no longer under his heels, he started to come down off his toes and immediately felt like his balls were being ripped off as well as crushed by the vise.
Mistress Karen watched fascinated as he flailed about trying to find a way to minimize the pain. She let him suffer until she sensed that he would pass out and then stepped in and allowed him to rest on her boots again as she loosed the vise. Alternating words of encouragement with ball-crushing twists of the vise she kept torturing him until he was covered with sweat and seemed to be on the verge of throwing up. "You've done very well Teddy," she said as she released him from the vise, removed the hook and unshackled him. "There's just one more punishment and then we can begin your slave training."
Joe didn't think he could take much more, but he doubted that anything could be worse than having his balls crushed in a vise. Realizing that he desperately wanted to be Mistress Karen's slave, he didn't say anything. She let him towel off the sweat covering his body and, telling him to sit on the floor, gave him a long drink of water, patting him on the head like a favorite dog. "Just this one last thing Teddy," she said, "and then you will begin to learn the joy of really serving me."
Joe was starting to enjoy being called Teddy, and he was quite happy as Mistress Karen plucked some well worn ropes out of her bag and told him to lay spread-eagled on the floor. She tied his wrists to the sturdy wooden legs of the workbench and then tied his ankles and ran ropes from them to drainage pipes on either side of the basement. He was quite content to lay there as Mistress Karen went back to her bag, snapped on a fresh pair of gloves and brought out a small white jar.
Joe knew he'd seen the jar somewhere before, but he couldn't recall where at first. Mistress Karen unscrewed the lid and placed a big gob of a yellowish-brown substance on the first two fingers of her right hand. Waving the mustard-like concoction under his nose, she watched him carefully for a reaction. When Joe didn't say anything, she started smearing it on his cock and balls. Joe was still trying to remember where he'd seen the white jar when the burning began.