Chapter 1: It started so simply

It was a grey, rainy February day when Kirstin’s beat up old coupe pulled up to the curb outside his apartment. For the past few weeks she’d been doing chores for him and they’d found a nice, easy rhythm. Brian watched from the window for a moment, before heading to the kitchen to wait for her like he usually did. Every Sunday, she stopped by, cleaned for an hour, and took a nice, easy thirty-five dollars home. While it was little more than chump change to Brian with his coding job at a major internet company, but for Kirstin, he knew it made the difference between paying the monthly minimum on her loans, credit cards, and other expenses, or incurring more late fees and falling further behind.

As usual, he left the door to his second floor apartment unlocked. As she closed the door behind her, he waited dressed like always, wearing navy pants, brown shoes and a checked shirt while he shuffled through some papers at the small kitchen table of his one bedroom apartment. “Hey there, Kirstin, how’s it going?” he asked with a smile.

He rose from his seat and approached her, planting his hands on his sides. He was usually very relaxed and informal, but today he was a little anxious. “Everything good?” he asked, grasping at words to make some conversation with her. “Thanks for coming by. This really helps a lot.” he added, giving an uncomfortable laugh, before moving his hands across his chest, not to know quite what to do with them. ‘Get a grip’ he told himself, she had no way of knowing what he was going to suggest today.

Kirstin smiled, greeting her brother informally with a wave. “Good, another day, another bill to pay, you know!” She had to make jokes. She’d gotten so far behind since college that it was almost an embarrassment. Brian had literally been a life saver when he offered her a little bit of money to clean once a week.

With her soft cotton top hugging her torso, she moved easily to the closet, getting her supplies. Bent over, he assumed she was oblivious to the view her denim shorts provided. Brian was in the ‘safe’ category, and she rarely, if ever, thought about what she wore around him. She could scruff out if she wanted to, he wouldn’t have minded - though since she was getting paid, she usually tried to wear something easy to work in, but was not in dire need of cleaning.

“You know it helps me way more than it helps you!” she said, starting with some simple pickup and organizing, dusting as she went, knocking any minor debris to the floor to be later picked up by the small vacuum he kept in the closet.

Brian forced a small smile at Kirstin’s comment and watched as she started getting her supplies. In a lot of ways, it made him feel bad that his sister thought they had such a great deal worked out. He got his place cleaned and she got money. What she didn’t realize was that he got a bit more out of the deal too, and this weekly view of her bent over, bottom pressed out into the air was one of the things that he enjoyed the most, especially with today’s denim jean shorts she was wearing. He felt his blood begin to flow as she began to straighten back up.

When he first started noticing girls, Brian had noticed Kirstin. He couldn’t really explain why he was fixated on her instead of their other sisters. He just was. Usually, he could hide his attraction pretty well, only getting a little flustered if some slipup gave him an unexpectedly nice view. But today was different. Today, his palms were already a bit sweaty and he just couldn’t find the right words. The reason? He had been thinking about a plan. He’d been thinking about it for weeks. And the plan he’d been thinking about for weeks was a plan to satisfy a hunger he’d had for years. But now that he was at the point he had thought about for a long time, he could not believe how taxing it was to actually initiate it.

“Uhh, hey, Kirstin...” he trailed off slightly, leaning against the doorway to the small living room she had started to clean. “Would you mind doing me a pretty big favor? I mean, I would plan on paying you, of course, so I’m not sure it’d really be a favor.” He glanced towards his bedroom attached to the far end of the living room. “It’s not that big a deal and you wouldn’t have to do it if you didn’t want to. I was just thinking that maybe you could help me out and I could help you out at the same time. What do you think?”. He was being awkward. Skittish. And he hated to admit it to himself, but he was a little scared of how this might go.

Her long black hair tied back in a casual ponytail while she worked, Brian hoped Kirstin was oblivious to the look of apprehension on his face. He knew these past few weeks had been nice for her, and while thirty-five dollars a week was not going to get her rich, it helped. A lot more than she probably cared to admit.

Stopping what she was doing for a moment when he had begun to speak, Kirstin furrowed her brow, trying to figure out just what it was he was asking. Beaming a smile, she answered easily, “Of course, you know I would help you with anything. Um, as long as it’s not some place dark and creepy and full of spiders!”.

He couldn’t help but grin at his sister’s obvious revulsion to the memories of the crawlspace. He, on the other hand, had much nicer memories of crawling around behind her, both of them on all fours, whenever they had to fish out old lawn furniture and various bits and bobs over the years. Snapping back to the task at hand though, he wiped the grin from his face. He had always felt like there was a power imbalance between them after college. Kirstin struggled, barely getting by, and was financially a mess. He, on the other hand, had been earning well and socking money away. Despite this, he did not always feel like the imbalance was necessarily in his favor. He was secretly, madly, and totally inappropriately attracted to her, which didn’t help matters when he was around her. Somehow, even with all of her struggles, she still remained the golden girl of the family. In this moment, he needed to remind himself of the very real and pragmatic fiscal imbalance between him. Remind himself that he had the power in this arrangement.

“No dark, creepy places, Kiki.” he said with a laugh, using his childhood nickname for her. “But you might wish it was. It’s kind of a weird request, but a friend of mine is trying to start a high heel line. She was hoping to get testers to get feedback on a few models she’s basing her heels off of and I was wondering if maybe you’d be up for testing them out. The minimum test time is to wear them and walk around for an hour, so I was thinking it’d be efficient for you to, assuming you’re open to it, wear them while you clean? You can then fill out a little survey form for her and I’d pass it along to her.” he swallowed hard, running through the lie in his head and praying he had told the story convincingly. “What do you say?”

“Oh, shoes? I love shoes, though high heels are not maybe the best for all jobs, this one is really not all that hard. Besides, I had to wear them on job interviews. I don’t mind filling out her survey and stuff, not at all!” Kirstin seemed only mildly surprised at his request...

For a second, Brian simply didn’t react. Was it that easy? Of course, he didn’t really know a shoe designer. He worked in tech and he’d never once mentioned knowing anyone or anything about the fashion industry. But somehow, Kirstin seemed to have just bought right into it. How he loved her at that moment.

“Okay. Let me just go grab them for you.” he replied, blinking. He disappeared into the bedroom and emerged a moment later with a pair of heels that seem like a prop from a porn set.

Sheepishly, he extended the heels with one hand, letting them dangle in the air. The shoes were made of black leather, and were as steep as can be with strappy lashings running across the feet and lower ankle. Clocking in at least four inches, though possibly five, they screamed ‘fuck me’.

“Her line has a very specific, um, style to them. Hence why she’s having trouble finding people to test them and give feedback on them. But I figured that since it was paying, you might be open to it.” For a moment, Brian wondered to himself if she’d balk now that she saw the shoes. But the thought of her saying yes and strutting about in them for an hour began to get the blood really flowing in his body.

Kirstin blinked, looking at the rather high heels, and seemed to be uncertain for a moment “Oh, wow, those are, I mean, I can see why she, um, I” she paused, “I mean I don’t know if I’ve ever even worn any like this”. Taking the shoes from him she held them, turning them from side to side and took a closer look. Sitting down on a nearby chair, she slipped her memory foam sandals off and wriggled her toes experimentally. “It, um, well, I might take a bit longer to clean with these on, these are kind of high” she said, undoing the straps and figuring out the best way to slip it onto her foot.

Just watching Kirstin put the shoes on was doing such things for Brian’s long term fantasy life that he could barely keep himself contained. Her denim shorts dug into her upper thigh a bit as she leaned forward messing with the shoe. Her chest heaved in a way that many would find distracting, though as with all the last few weeks, it seemed Kirstin was oblivious to any looks or reactions her ‘safe’ brother might make. Finally getting the shoe on, she set it down on the ground, wobbling a bit as she repeated the process with the other shoe. Grunting a little as she really had to bend down over her knees to get the buckles tight, she sat back up with a woosh, her face red from the exertion. Brian could not take his eyes off of her. He quickly stopped staring when she spoke again, sounding a little out of breath from all the bending.

“Oh, well, here goes nothing!” she said, making a joke as she levered herself up onto her feet, her calves stretching as she stood on tiptoe, her feet braced by the slanted sole of the shoes.

“Don’t worry at all about measuring the cleaning time today. Since you’re helping out my friend, we’ll just stop at the hour mark regardless of what’s been done.” Brian suggested with a smile. He stood a few feet away, watching his sister figure out the heels. As she did, his pulse quickened. On one hand, her focus on the heels had let him absolutely consume her body with his eyes. On the other hand though, was the fact that his own sister was putting on a pair of high heels that he found by googling ‘sluttiest heels’. He couldn’t believe it, but she was about to walk around his apartment in a pair of shoes made for hookers, strippers, and porn stars.

As she rose unsteadily to full height in the heels, his jaw dropped. “W-woah, Kirstin. They actually really work on you.” He shook his head, collecting himself. “Uh, I mean, like, I’m amazed you can already stand in them. Just uh, be careful cleaning, OK? Do you feel safe? You feel comfortable?” He asked, just trying to make conversation as he eyed her long legs and beautiful feet propped up in the whorish heels, his cock beginning to grow in his pants.

“Oh, it’s ok, like I said, I’ve got to move slowly for a bit. I can do it though, see?” Kirstin said, taking another step forward, and bending down slowly to grab her dust towel. Slowly, tottering slightly, she returned to clearing the dust and straightening the small knick-knacks around the room. “Wooo” she said, turning and putting her hands on her hips as she looked to see if she had missed anything.

The whole thing was almost too much for Brian. Her body, usually a treat even in flip flops was elongated and enhanced by the heels. With a slight catch though, he realized that watching her struggle to move in the heels, clumsy but somehow sexier because of it, was giving him an enormous erection. “Umm, hey, I’m just going to sit over here but I’ll keep an eye on you to make sure you don’t fall or get hurt or anything.” he murmured, trying his best to be furtive in his enjoyment of his sister’s body.