Since I already have this on AO3, why not also post it here...?

Inspired by sleein's beautiful artwork with Dave in high heels.


It was a day like any other day. No wait, no it wasn't.

Kanaya Maryam liked to consider herself a reasonably sane person. She has had her fair share of experience in life and it wasn't so often that she would openly admit to being left utterly speechless.

But this was no ordinary day. It was no longer possible to consider the present day able of being categorized as "ordinary". Not when a group of loud, obscenely cheerful young men had just come in front of her boutique.

Men. Coming to a women's boutique. All by themselves.

They looked positively giddy and Kanaya was so stunned she was actually afraid of what might be happening, until she spotted someone familiar among them. She knew that type of pale hair, having seen it so very many times on a lovely girl. Who happened to be the aforementioned shop owner's girlfriend. Who also happened to know someone else with the exact same shade of hair – who was her girlfriend's twin brother.

Dave Strider was in front of his sister's girlfriend's boutique.

Right as she was taking note of all this, Dave came to stand in front of Kanaya, all the other men now flocked behind him. She noticed that they were warily eying the front of her boutique from time to time; Kanaya quietly bristled at that – men. So utterly ridiculous, afraid of even looking at something lest it emasculates them.

But Dave (her love's twin brother) was there, so she refrained from visibly showing any kind of hostility, wary of possible disapproval from his side. She didn't know him very well and wasn't sure what kind of person he was. Dave was Rose's sibling and by the looks of it, –despite all their teasing and barbs towards each other-, they seemed very close and caring deeply for each other; all the more reason for Kanaya to try not to leave a bad impression.

At least he didn't act the same way as all the other men behind him, she appreciated that. They started nudging the blond young man with their elbows and snickering – no, they were positively giggling, like a bunch of silly little schoolgirls.

Dave ignored them all and just took one more step forward, now face to face with his twin's newest girlfriend. Ever so casually, he placed his hands in his pockets.

"Hey, Kanaya." He greeted her, deadpan and poker-faced. Murmurs promptly erupted behind him.

"Hello Dave." She responded ever so politely, trying not to let her questioning gaze slip past his shoulder. "What brings you here? And your companions…?" She hesitantly added the last bit, as she was now aware of the slight tension in his jaw, his straight posture and feet spread shoulder width.

"I lost a bet." Confusion seemed to be on today's list of flavors quite frequently, as that brought Kanaya out of her stupor and brought her into another one.

"You… lost a bet?" she blinked at the seemingly random statement. Dave nodded once and took a glance behind his shoulder before turning again towards the stunned woman.

"These guys" he pointed with his thumb to the group of men -now shuffling awkwardly- right behind him. "…got the idea to make the loser wear high heels for the rest of the night."

"Wear high heels?" and the blond nodded and repeated "For rest of the night."

"For the rest of the night?" she echoed, eyebrows high on her forehead and he nodded again. "Why?" and Dave shrugged.

"Something about wearing girly stuff for a few hours being a suitable punishment…" Oh. Kanaya could feel her temper rising at that; she was so close to sending a furious glare towards the group. Stupid misogynistic baboons… The nerve

But

Her mind blanked as she suddenly realized what that meant.

" You… lost a bet...?" and Dave nodded – ever so patient - once more. So that meant that he…

"Since I'm gonna be wearing a pair, I thought I might as well look for some nicer ones. I figured you knew more about this than I do, so might as well check out your fine establishment."

Oh.

Kanaya Mariam would admit that she had been left utterly speechless this time. For many reasons.

"You… want my help…?" she winced at her own wording. Men are prideful beings, regardless of their own awareness of it. She did not want to embarrass Dave, especially in front of this rowdy bunch. But he did not seem all that bothered and he just shrugged one more time.

"If I have to do it, might as well pull all the stops. Thought a women's touch might be better, since I barely know how to go about this kind of stuff." She felt a new wave of warmth for the man in front of her after hearing that.

"But what about Rose?" she couldn't help but ask. Surely – despite their sassy way of speaking towards each other – she would be the first for him to go to.

"Nah, haven't you seen her style? She always wears flats - and besides" he pointedly glanced over the woman's shoulder towards her boutique "…you're the one with the resources."

Oh.

Kanaya found herself smiling at Dave's words.

"Well then" she turned towards her shop, her gaze still towards the blond "it would be my pleasure to help." She beckoned him and he hesitated only for a second before following her. The rest of the men tried to further be amused of the situation and hollered after Dave. "Hey Strider, make it good will ya, we'll be waiting for you back at my place!" Dave waved at them without turning around; his back postured like the one of a resigned man accepting this small sting to his pride. As she opened the door for her new client, and Kanaya knew that she started to genuinely care about Rose's brother; she certainly wanted to help the young man in any way she could. Once he crossed the threshold, she sent a withering glare towards the bunch of fools still waffling in front of her shop before closing the door behind her, bell merrily chiming.

The silence of her shop enveloped them right after that.

Kanaya would admit that the entire situation was fairly odd, but she was also genuinely excited. So she turned towards Dave as she got back into her "workplace" role.

"So is there any specific type of footwear that you're supposed to be wearing?" Her mind was already working, looking over the length of his body to come up with suitable possibilities.

Dave combed through the hair on the back of his neck; he seemed thoughtful, a bit lost. "I don't think they actually thought that much, just a pair of heels to break my legs with." Kanaya nodded, no longer bothering to get annoyed at the wording. "So no kitten heels, got it." Dave's face got thoughtful "I'm not sure what kind those are but yeah, they sound tame." She nodded in approval. He quickly responded at that.

"Heck no, I'm not getting the easy way out. Bring out the big guns." His sudden fiery tone surprised her, getting her out of her inner fashion-related musings. His face seemed blank as always, but she saw the slight press of his lips and a fierce, competitive grin slowly crept up her face at his next words.

"If they want a show, then that's what they'll fuckin' get." He was in a defensive posture, yet confident - arms crossed in front of his chest red on red, bold, fiery and passionate-…

It suddenly came to her like a light bulb turned on right above her head.

"I've got it, dear." She slipped into the next room ("Staff Only") thus she didn't get to see Dave's slight jump and the rise of his eyebrows over his shades in surprise at the term of endearment. Kanaya was on a roll, the perfect item for him burning in her mind as she dug through the boxes lined up on the shelves. Come on, come on, she knew she had them somewhere…

"Ah, yes; there they are!"

Dave dared to peek his head into the room and Kanaya turned towards him with a triumphant smile on her face. "What size are you, Dave?"

"Uh, six and a half." She nodded and turned back towards the stack of boxes she just got off the shelf and started to look for the right one. "Right, I assume your foot is more long rather than wide, am I right?" Dave glanced at her curiously.

"Wait, does that even matter?" and now Kanaya slightly shrugged one of her shoulders as she kept searching.

"It actually depends on the model, like for any other shoe actually." He stayed silent but she wasn't bothered by it, too preoccupied by her own thoughts, bordering on positively gleeful. She sprang to her feet, thrusting a nondescript rectangular box in his arms.

"Try these on!" and then grabbed his arm, practically dragging him by the wrist in her energetic pace, back towards the other side of her shop. She placed him right next to a stool and told him to wait there as she headed towards someplace else. Dave proceeded to stand there with the box in his hands, feeling a bit overwhelmed by the absurd way the day had been developing so far.

Kanaya came back with a flat packet in her hands, and he knew as much from living with his sister to recognize a pair of stockings when he saw one. His sibling's girlfriend seemed to get out of her own enthusiasm a bit, just enough to see that he was really trying to adjust to all of this and she looked at him carefully for his reaction as she raised the packet slightly.

"I thought it might be more comfortable for you to wear them with something, the shoes would slip on much easier" she added helpfully and he couldn't help but nod. Kanaya smiled warmly at him again and such open display of affection was really new (and kind of unsettling) to him.

"Not to mention the fact that they would look great with them." She added as she was handing him the pair of stockings. "Trust me on this when I say that these will suit you." Dave looked at her, all her features so kind and genuinely caring and he could see why Rose would be drawn to this certain woman. He said nothing but Kanaya certainly saw the slight curving of his lips, the deep breath coming through his lungs and when he nodded she knew he was genuinely grateful for her help. The blond then seated himself on the stool and started unlacing his shoes.

As he was about to open the box, Kanaya froze as she realized something.

"Dave. Those stockings are thigh high. You'll have to take off your pants to put them on."

And so he did. He took them off without any complaint and didn't flinch while left in his orange boxer briefs in a women's shop. He then sat back down and listened to Kanaya as she taught him how to properly roll up the stockings in order to not damage the fabric.

His legs were long and thin, just the right amount for the stockings to make Dave look as slender as a model on the catwalk. Especially with those heels.

Oh dear. It was actually coming out better than she had expected.


Kanaya walked with Dave on the street, him with the box in his hands – both shoes and stockings inside. She agreed to accompany him to his friend's house, where he was going to act out his punishment from the bet. Apparently the owner of the house was having a small party there. She was going to stay and support Dave while he was in the presence of in front of that foolish group and she would certainly not take "no" for an answer.


"Aww c'mon Strider, where's your part of the deal?" a man whined loudly as he came into the room, Kanaya in tow. Several voices were raised over the music blasting through the speakers, exclaiming indignantly.

"Yo Strider, you lost the bet dude!"

"Yeah, take it like a man!" Kanaya clenched her jaw, willing herself to not get involved.

"Chill man" the blond next to her responded. "I just couldn't walk all the way here in my getup. It would take forever, not to mention it would totally ruin the footwear." The group of men chuckled at that and Dave then turned towards the nearest room and closed the door behind him. Kanaya quietly seated herself on a vacant armchair a bit further away from the bunch, patiently waiting for him to come out.

After less than a minute, one of the men waiting outside knocked loudly on the door, yelling at Dave to come out already. The doorknob twisted from the other side and the door creaked open slowly; everyone practically holding their breath, not knowing what they'll see.

Once Dave got back, Kanaya smirked as the atmosphere within the room changed.

A constant buzz was within the space yet none of the obscenely loud voices as before. It was like they were trying to be amused, but they really couldn't.

Because Dave Strider was hot as Hell in high heels.

He already practiced walking with them inside Kanaya's boutique and Dave was now casually striding (hah, good one) across the room in a shiny new pair of fire truck red four inch heels. He was, once again, in his underwear, only with his shirt still on; but it didn't seem to matter, not with the distraction of his mile-long legs covered mid-thigh in a pair of black opaque stockings. All of the men were now gaping like fishes, eyes drawn to the movement of his lower body, the shape of his toned calves subtle and firm, the skin right above the stocking in contrast with the dark fabric - yet utterly attractive as well all on its own.

Kanaya already had admitted to herself that he was just as beautiful as his sister was.

His sense of balance was amazing, having just worn that pair for the first time in the very same day and now – now he lifted his leg behind him, and grabbed onto the stiletto by the heel to adjust it on his foot. No leaning on anything while doing it. Kanaya herself gaped at that; Dave was ridiculously, perfectly balanced while standing on one leg like a stork, the foot on the ground even daring to lean only on the sharp heel of the shoe for three full seconds. Even women with lifelong experience wearing such shoes would have a hard time doing that and Kanaya was too stunned to get mad at his total disregard towards the safe keeping of those shoes.

He took a few more steps nonchalantly and then turned towards her and he actually looked relaxed, he was comfortable.

"Hey Kan" she had never gotten a nickname before, but Kanaya knew he was addressing her.

"Yes dear?"

Dave Strider then cocked his hips, and their narrowness did not deter from the utter beauty of him wearing black thigh highs and stilettos in deep bright red.

"I don't know about anybody else, but right now…" he did not let it be expressed by his face but she could sense the large smirk he had on the inside as he said "I actually feel pretty damn manly."

Kanaya let her own smirk show and it was practically villainous.


Dave bonding with Kanaya over how lame everyone else is - totes my headcanon.