Chapter 6: Weekend at Brian’s

Parked outside of her brother’s apartment, Kirstin took a deep breath. It was Friday afternoon, not Sunday, and she knew that things were going to be a bit different. She was not exactly sure how, but after the last time she had been over and had stayed the whole day, she could sense he was getting ready to change things up again.

Last Sunday had been very similar to the first time he had her do a strip tease a few weeks ago. She had probably not gotten a lot better at being a stripper, but she had begun to discern what he really liked, and she had gotten almost as much money the second time as she had the first. Sunday had been the third time she was there and had stripped before cleaning, and she had changed up the order of things, putting the slutty heels that her brother liked too much on first. She had noticed that his eyes were often drawn to her heels, and he had made more than one comment about her toes

That was the reason for her hesitation. Her toes. After she had stripped, and he had cum once watching her, she had proceeded to clean up his apartment like she usually did. Cleaning the kitchen, he had watched as always, cumming again as she scrubbed the floor. She had started to take a little more time with that task, though it was still more than a little awkward to know he was looking at her bottom like that. But it was later, after she was done, that the ‘toes’ issue came up.

It had started out innocently enough. Brian suggested she stay for a few more hours, cook dinner, and offered a nice bonus for the extra time, so she had agreed. He had her get dressed in one of the lingerie outfits she had worn previously once she was done with her chores, and the afternoon was pleasant, watching some television, and waiting for dinner time. She was stretched out, her feet still in heels resting on a small footstool, when she had noticed Brian watching her feet as she slowly tapped in time to the background music. She had not argued when he asked her to turn and put her feet in his lap, and when she saw his arousal, she knew that she was likely going to get another bonus. He didn’t touch her though, other than to position her feet a couple times, but it was not long before he had reached down to once again play with himself, the third time that day. She continued to try and watch the show as he moved her feet away briefly while he pulled his shorts down, placing them back on his lap, inches away from his exposed cock.

She had not been able to stay completely disinterested, and she watched as he stroked himself, his eyes never leaving her feet. As he sped up, she could tell that he was getting close, and she started to pull away a little, to give him some room. Suddenly, his free hand had grabbed her ankle, turning and pulling the toes against his cock, the sole of her shoe pressing against his flesh as he began to spurt, albeit in a lesser flood than earlier in the day. She had pulled away, harder, eventually getting her feet back, but not before he had coated them with his spend. Flabbergasted, she had glared at him, waiting for his apology, but when he had simply looked up and smiled, telling her she had pretty feet, she had gotten up and stormed off to clean up.

Even though he had apologized, and even kicked in another fifty dollars, she had still been a bit steamed all through preparing dinner and even during their meal. His continued acceptance of what had happened as perfectly natural, if perhaps somewhat shocking, continued to worry her. When he had suggested she come on Friday and stay for some serious cleaning on Saturday, she had agreed, albeit reluctantly. She had come to depend on his financial assistance, and the thought of some extra money was enough for her to forgive his previous behavior.

Sitting in her car, getting ready to go in, she knew that her behavior, her coming back, was giving at least tacit approval to what he had done. Unsure if she was ready to deal with that fact, she hesitated for ten long minutes before giving in with a sigh and heading up to the walk. So, her brother liked feet, she had known that. And if she was not really crazy about it, he had cared to show it, it was not really all that different than before. His ‘stuff’ had gotten on her more than once, though it had not quite been that much, or that much on purpose.

Seeing Kirstin’s car pull up to his apartment, Brian felt a tightening in his chest he hadn’t experienced for some time. The tasks he put his sister to had come in waves, first with an initial rise when he would get a sense of her tolerances for what he wanted to do. This eventually built to the act he wanted her to perform, or something similar to it if she wouldn’t accept the specific favor he wanted, which was the crest of the wave. And finally, the long, slow downward landing back to the baseline, when the act that had once seemed impossibly taboo was now just a normal course of action for the siblings.

It was always the crest that was the most intense and, probably for both of them, uncomfortable. And they were now he understood, approaching one of the crests. Despite sometimes feeling like he essentially owned her, Brian still realized that his sister could walk out of their arrangement at any time. And while he did feel that he had successfully eroded this independence to a significant degree, he was sure that she was not yet fully broken. This crest, he thought to himself, would remedy that.

He had prefaced what he had planned for this weekend with the idea that he needed a deep cleaning in the apartment. Kirstin would arrive on Friday, and spend two nights with him, finally leaving on Sunday evening. What his sister may or may not have understood was that the real objective of this weekend was not to clean, but to keep her in a submissive state for an extended period. No longer would she have her freedom after a few short hours. She would experience for the first time being submissive for days on end.

He had spent many hours researching submission and how to influence someone to be more submissive. Today, he would experiment with one of the ideas he had come across. Sitting a few feet from the entrance of his apartment, with their backs pointing towards the door so that they could almost be walked into, were a pair of steep, black, strappy heels. This wasn’t unusual, except for the large, metal buckle that clasped around the ankle and closed around a metal hoop. The metal hoop, Kirstin would discover, would be for the small padlocks he would install once her feet were secured in her new shoes.

“Hey there, Kirstin.” he said as the door, unlocked as usual for her, gently swung open. “I hope you’re not too upset about what happened last week. Today’s a really big opportunity for you, so I think it’d be best if you focused on the future. Once you get the door shut, why don’t we skip the strip today and instead get you straight into these heels? This weekend is going to be a little different than what you’re used to.”

Kirstin closed the door behind her and looked at the shoes he had left just inside the door. As she stepped towards them, she kicked off her sandals and wriggled her toes. “It’s ok, Brian, you just surprised me. Besides, who else are you going to get to clean as well as I do, hmm?” she said, trying to make light of what had happened, not even speaking about it directly. She could see the heels he had left for her were as high as any to date, and as she leaned on one foot, she slipped her other foot into the steep shoe, trying to balance carefully and slip them on like she assumed he wanted. It was harder than it looked, and she had to hold onto the side of the entranceway as she slid her second foot into place. Wobbling a little until she felt her balance return and her muscles adjust to the steep pitch of the sole of the heels, she stepped to the side and turned her back to the wall, letting herself lean against it as she reached down to do up the straps. She was not really sure why he was having her start like this, but as long as he was paying, she did not really care what order things happened in anymore.

Finished, her breath coming back to her quickly as she stood back up, she made her way to where Brian sat, and asked “So, where did you want me to start?”

It never got old for him. No matter how many times he saw her do it the act of watching Kirstin, whose style was normally fairly plain, if not outright prudish, put on a pair of overtly sexual heels. And to be frank, these heels weren’t just sexual. They were whorish. They were the heels worn by sex workers. And by sex slaves. He found every inch of his older sister arousing in some form or fashion, and steep high heels seemed to enhance her already potent sexual charms immensely. Not only were her pretty feet pinched and pointed by them, but her calves would work just a little harder with every step, definition appearing in them that was not evident when she was flat footed. Perhaps most enticingly of all was how the curves of her hips and her big, wide bottom became ever rounder and more prominent once she was in her heels. He had once read that if a woman wore high heels for too long, the tendons in her calves would begin to shorten, at which point walking about flat footed would become uncomfortable, if not even painful for her. He had been disappointed that Kirstin had continued to prefer flip flops and sneakers to high heels when she wasn’t working for him and he had begun to think that if he couldn’t change her tastes through occasional exposure, perhaps he could change them by making her preferred footwear painful. And it was partly with this in mind that he had concocted his plan for this weekend.

“Well, Kirstin, I think the best place to start is with the rules for this weekend.” he crossed his arms and leaned against the wall, letting his eyes enjoy the view of her body. The clash of her regular street clothes against the black leather heels had an arousing effect in its own unique way. “As we discussed, I want you to stay here working until Sunday night. That means it’s going to be an enormous paycheck, but it also means you’re on the clock for the whole time.” He paused for a moment, preparing his next words in his mind one last time. “I think we can agree,” he coughed slightly into his hand, “that the nature of your work has evolved over the past few months. So I just want us to both have the same understanding that when I say you are on the clock, it means that you’re not only cleaning, but also providing the other, more sexual services as well. If I want a strip show the very first thing tomorrow morning, you will give it to me. If I ask you to expose yourself to me, you’ll stop what you’re doing, flaunt what I have asked you to flaunt, and only resume whatever it was you were doing when I tell you I am satisfied.” He took another moment, trying his best to gauge his sister’s reaction. “I feel it’s only fair that such a big payout requires some premium service.”

“Consider the heels as a physical symbol of the role of Sexy Sister Maid, if you will.”

Reaching into his pocket with one hand, he produced two brass locks and a small key on a loop. “If this all sounds agreeable to you then come, put these locks on your high heels. I will take them off for you when you are done with work on Sunday night. But until then, it will be completely at my discretion as to when you have the heels on or off.”

The idea that he wanted, or expected, her to be in full on sexy maid mode all weekend did not surprise Kirstin. She was a bit taken aback when he talked about continuing all through Sunday night, though she had no real objection. It would likely mean quite a bit extra money, and 2 days or three was not that much different. She would have to get her laundry done during the week, but other than that, she knew she could spare the time. The words he had said ‘big payout’ resonated within her mind and she was already thinking about what bill or bills she might be able to pay off after this weekend. She stepped forward, not really thinking much about the locks - she knew he’d take them off if she needed,. ‘Why wouldn’t he? She thought to herself, coming to a stop in front of him.

“Okey doke boss” she said, smiling a little, making a bit of a joke out of being locked in.

The soft clicks of the locks closing echoed slightly, and as he sat back up straight, she asked again. “Um, so, where first? Or did you want me to, you know, get out of these?” Her hand waved along side her body, highlighting her casual clothes. She knew he liked the stripping, but he had said something about tomorrow, and she did not see another outfit or anything, so she was not sure if she was just supposed to start out normal. Thinking that was likely the case, she looked towards the closet where her cleaning supplies were kept, glancing back at him as she waited for his direction, or directions.

Brian felt a thrill of excitement as the locks clicked into place, trapping Kirstin’s feet into the heels and by extension, her body into servitude. He was pleased to see that these heels worked nicely on her, lifting her up with a slight forward pitch. The straps crisscrossed her pale feet and pinched her exposed toes at the end.

“Yeah, start with the cleaning just the way you are.” he said with a confirmatory nod towards the closet. “We’ll have plenty of time for fun.”.

Brian had noticed that his sister was often at least a little bit wet during her dances and he was determined to find out what exactly about their activities was arousing her. Was it the domestic servitude that got her off? The thought of a nude, heeled woman performing housework while being ogled flying in the face of every modern movement and arousing some dark corner of her in the process? Or was it the dancing? Did the act of willfully trying to get someone off in turn get her going? Or was it the sight of watching him stroke that got Kirstin’s lips wet?

He let her clean for a bit while he casually went about his business in the living room. He did not hide his enjoyment of seeing her in her heels, even if she was clothed. But every now and again, he would stop her midway through her work and ask her to expose her pussy to him. He would occasionally ask to see her breasts as well, but he was mostly curious about the state of her wetness. He hadn’t expected it, but the random acts of exposure before a return to her fully covered state aroused him quite a bit. “Mmm, you know, this kind of thing is sexy as fuck. Just watching you lift your shirt like that or hike your shorts down just enough ... I’d love to try this sort of thing when we’re out and about sometime.”. He flashed a naughty but still playful smile before leaving her to her chores once again.

After she was halfway done with her chores, he told her she could finish the rest of her work naked. No need for an elaborate strip show, just finish her work naked. “If you need any help getting your shorts over the heels, let me know.” he said before returning to the living room.

Periodically, Brian continued to check on Kirstin, keeping an eye on her pussy to check for any dampness. He was determined to find out what had made her wet in her previous dances, and then use that as a lever on her in addition to the money.

Kirstin tossed her bra on top of her shirt, running her hands along the underside of her breasts to ease the slight itch her bra had left her with. The frequent stops to ‘show off’ for Brian had been an interesting change, she had thought, noting he had (not surprisingly) seemed quite interested in having her expose her pussy and lower body most frequently. Unsnapping her shorts, she started to work them down over her hips, dragging her slightly damp panties along with them, when she stopped, realizing he might have been passively requesting to help. Smiling at his obvious interest, though he had not seemed overtly aroused yet, she walked into the living room, her shorts ½ over her hips, the only covering left on her body. Moving to stand in front of his spot on the couch, she pushed her shorts lower, leaving them stretched tight across her upper thighs, saying “It would be easier if you slip them over the heels, they are quite large compared to leg openings...”. As her shorts fell around her ankles, she felt that familiar, secret tingle when she caught his eyes on her exposure. More and more she had come to associate being looked at with some measure of enjoyment, though she knew that much of it was also that odd feeling she had whenever she had simply done as he ordered. The strip teases had been different, and while she had enjoyed the teasing, and the effect she’d had on him, her true enjoyment continued to be acting like she was now, following his orders, putting herself under his control. Every time he had wanted her to expose herself, she had felt a renewed urge to do whatever he wanted. Telling herself she wanted to be the best ‘sexy’ maid in order to get the best rewards, she knew that part of her continued to enjoy the way he controlled her, so to speak.

As Brian worked the shorts from his sister’s broad hips, he found himself falling into one of his sexual reveries that only she could put him in. The feeling of her pale legs beneath his fingers was incredible, but it was also the very first time he had been this close to her sex. As she stood before him and he sat forward to get the shorts off of her, his face was mere inches from the dark thatch of hair that covered her wet lips. He swore he could smell her. His cock hardened immediately as he breathed her in, fantasizing about licking her wetness before pushing himself into her warmth.

As her second foot slid from the shorts, he sat back on the sofa, completely erect. He admired her ample backside as she sauntered back to the last of her chores. When she left the room and he could hear her heels clicking throughout the rest of his apartment, he closed his eyes, reached down, and rubbed himself in anticipation of what was coming next.

Standing still while he took his time, carefully lifting one foot at a time to work the fabric over each heel, Kirstin could feel his hands, warm on her skin, sending tiny tingles up her legs. Moving back, she squatted down to grab her shorts, holding them in her hand as she went back to the kitchen. Tossing her shorts on top of the small pile of her clothes on the table, she grabbed the bucket and put it in the sink, running some water to get it warm. Shifting from foot to foot, she could feel her muscles flexing as she continued to get used to the high heels. Tsking as she finished filling the bucket, she headed to the laundry, realizing she had forgotten to move the washed items into the dryer.

Minutes later, she was about finished with her ‘usual’ cleaning. She had gotten so used to working and being nude around her brother, that his frequent checks on her had barely registered with her. She sat back on her heels, looking at the clean floor and felt good about a completed task, idly running a hand up to wipe away a little perspiration from beneath her full breasts.

“Kirstin! Are you all set?” her brother’s voice called from the living room. The sound of some sort of dance track was pulsing behind his voice as he spoke, followed by the muffled sound of voices from the TV. “I want you to come watch something with me.”

When she arrived, Brian was sitting on the couch, his shorts pitched up slightly. “Oh, good.” Brian said when Kirstin entered the room. “I wanted to watch this with you. Take a seat.” he nodded to the sofa next to him but before she took a seat, he looked down at her heeled feet and patted his crotch. “I like it when you put them up here.” he murmured, his request not actually coming in the form of a request.

A beautiful woman was on the television at the head of a classroom. She was dressed too sexily to be a teacher on anything other than a porn flick, and the acting fell in line with this assumption. The teacher’s students had found naughty pictures of her online and now there would be hell to pay. The teacher was flustered and protesting, but this was porn, so the protestations were paper thin and by the time she was undoing her shirt she was purring like a kitten. Surely, no woman could enjoy being coerced into stripping that readily, Brian thought to himself with a smirk. As the teacher began to strip for her class, Brian turned to his sister. “Watch this, she has some amazing moves I’d love for you to try.”

Not sure what her brother wanted at the moment, Kirstin willingly sat down on the couch, eager to take a little break. Eyeing his lap, she did not protest when he requested her to prop her feet up again, though she felt an odd nervousness. As she made herself comfortable on the couch, stretching out naked next to her clothed brother, she caught his appraising look more than once, and she wondered if she was perhaps not making the wisest of choices.

Turning her attention to the TV and away from her brother’s lap and his hand now resting on her ankle, his fingers idly playing with one of the straps of her heels, she saw a woman begin to strip and she looked back at her brother, curious to understand what it is he wanted her to learn. She watched as the ‘teacher’ stripped down to her underwear, not doing anything she thought was all that unusual. When they showed the students watching, she could see the boys’ obvious arousal, and when one of them pulled out his hard prick, she felt an answering twinge inside of her own body. There was something about an exposed, hard, cock that she could not help but react to. Over the last weeks, the frequent sight of Brian’s thick staff had given her plenty to think about in her quiet moments, and even though it was her brother’s cock, the sight was something she knew she enjoyed.