Red Stilettos

by Thesandman

Caution: This Sex Story contains strong sexual content, including Masturbation, Exhibitionism, Voyeurism, .

Desc: Sex Story: Larry and Dave discover the urban legend about working in a shoe store is true.

Let me begin by saying, I have worked in a shoe store now for several years, and never not once have I ever encountered a woman whose pussy I ever saw, let alone flashing me her panties, or crotch just for the sake of doing so. I would dare say, for all the stories I'd heard told about this happening, that ninety-nine percent of them where pure fantasy and over active imaginations. Even Larry one of the guys I worked with who was ruggedly handsome and good-looking had only had one instance where he swore the young woman actually flashed her panty-less crotch at him, and that was subject for debate.

And not that I didn't wish for it to happen. I certainly did, especially with the number of very attractive and good looking women who came into the store and tried on countless pairs of shoes. But every single one of them was conscious of the way they sat if they actually came in wearing skirts, mostly ... women wore shorts or slacks, and the opportunity for something like that to actually happen never really presented itself.

And then I met Mrs. Anderson.

Over the course of time I had gotten to know a few regular customers on a first name basis, and I was always very much aware of brand new customers coming into the store that I had never seen before, especially when they tended to be attractive ones, like Mrs. Anderson.

When I saw her enter the store I knew immediately there was something particularly interesting and attractive about her. Maybe it was the look in her eyes that told me that. I'd always been a fairly good judge of character on the one hand, but there was always something about the way a person looked at you that said a lot before they'd even spoken a single word. As I learned later when running her credit card after selling her a couple of pairs of shoes, Jackie Anderson as she was called, was a very attractive looking woman. I guessed her to be in her mid to late forty's though she could easily have passed for ten years younger than that, something I managed to discover when checking her personal ID against her credit card while finalizing her purchases. But I digress here.

It was midweek in the middle of the day. Larry had just left a few minutes ago for his lunch break leaving me to handle the store all by myself, which usually wasn't all that difficult as most of our business took place in the early afternoon when the two of us were together, or when the store Manager came in for the afternoon to late evening shift when most of the sales were made. Up until now, all we'd had was a handful of window shoppers with no one actually buying anything. When Mrs. Anderson came in, I knew without any doubt I was about to make my first sale of the day as she scrutinized two particular styles of shoes, and then approached me with them.

"Do you have these in my size?" she asked politely.

I've always been fairly accurate in my estimation of a woman's shoe size having done it for so long now. But it was a hard and fast rule that we always ... always ... measure the woman's foot anyway for a number of reasons. First, not every shoe will fit a woman's feet perfectly, even if it is supposed to be her size. Secondly, it's a waste of time to drag out several pairs of shoes in differing sizes, a luxury we can't afford especially when it gets particularly busy. But thirdly, for myself anyway, I like taking the time to fit a woman's foot, adds more of a personal touch for one thing, and for another, seeing a woman's foot, how she takes care of it, tells me a lot about her.

You'd think I had a foot fetish because of where I worked, or why I enjoyed actually holding or touching a woman's foot. Don't get me wrong, I enjoy that, it can indeed be very intimate. But no ... I am in fact a boob man, always have been, always will be. And Mrs. Anderson had a nice looking pair of breasts too! So surprisingly, it wasn't the urban legend of getting a peek up her skirt, or in her spreading her legs to expose herself to me that I was expecting, well actually hoping for anyway. I'd actually seen more cleavage in this business than I had the other, and as Jackie leaned over examining her foot off to one side, I got one of the best two second glimpses at tit flesh than I'd had in a long, long time. Her blouse bellowed out just enough in front to give me the two second peek at the very lacy bra she was wearing that barely concealed two very delectable looking orbs that were barely contained within it.

It was at that moment of course that she chose to stand up in order to see how they felt as she walked in them, making her way over towards the mirror to see how she looked in them as well. From my perspective, they looked great on her, especially with her well toned and muscled calves that hinted at her in either once being a dancer, or very possibly still athletically running.

"I like these, so for sure this pair, but I'd also like to try on a couple of pairs of sandals," she informed me. I'd already measured her foot for a size six and a half, and knew upon doing so that the pair of sandals she'd brought over to me and had expressed some interest in that we no longer had in her size. I then recommended a couple of other styles and mentioned I'd go get them and bring them out to her. She smiled at that, and then asked.

"May I ask where the ladies room is?"

All we had was a unisex single bathroom, but at least it was clean. I directed her towards that, disappearing myself into the back stock room to pick out a few different pairs of sandals in her size. I watched her walk off, once again admiring the view as she did. Like I said, she was a very attractive looking woman with dark brown shoulder length hair, around five and a half feet or so, a more than ample bosom and almost emerald green eyes that I found most alluring ... next to her smile. By the time I'd returned with four or five pairs of shoes, she was again waiting for me having settled herself back in her seat. As I slipped on the first pair for her to look at, I caught a faint sound that caused me to look up and about confusing me. I couldn't tell what it was, or where it was actually coming from. Initially, I even wondered if my ears were ringing.

"Anything wrong?" she asked causing me to refocus my attention back to her.

"Oh, no ... nothing. Just thought I heard something," I told her politely as I slipped on the first sandal, lifting her leg slightly in order to do so, though like I said, even with the skirt she had on, I was still sitting up way too far to have seen anything, nor was I really trying to either. But again ... I could hear this odd little sound, and quickly looked about wondering where on earth it was coming from.

"I'm not sure about this style," she said once again standing up in order to have a look at herself in the mirror. When she did, the noise stopped though I once again looked about wondering at the source. Dissatisfied with their appearance, she returned in order to try on the next pair. As I again lifted her leg briefly in order to remove the ones she had on ... the sound returned. And this time I knew exactly where it was coming from!

We repeated this process once more, but she finally settled on the pair of black stiletto heels she'd first tried on, and the second pair of sandals we'd tried. I checked her out ... literally at the counter, just as Larry returned from his lunch break. He checked her out too as she passed by him on her way out of the store, but not before turning to smile and thank me for helping her.

"Man ... you're never going to believe this," I began telling my friend. And I was right ... he didn't.

Two weeks passed, and then she once again came into the store, almost exactly at the same time and day she had the last time. Larry had just left for lunch, and I couldn't help but wonder if she hadn't been waiting for him to do that before coming into the store.

"Hi again Mrs. Anderson," I said in greeting her. I of course had remembered her name from the last time. She smiled broadly at that, and told me it was ok to call her Jackie. She then informed me she was there to pick up and try on a new pair of running shoes, so I was correct in my assumption that she did that, and quickly pointed out several pairs of good running shoes she might be interested in. I noticed she was wearing a reasonably short denim skirt with a matching jacket that she wore over what appeared to be a rather tight, form fitting white tank top beneath it. As it was a warm summer's day, we quite naturally had the air conditioning on. Even so, as she sat she removed her jacket placing it on the chair beside her. Almost immediately I saw the twin points of her nipples suddenly harden, pressing against the thin tightly molded material of her top. It was evident she wasn't wearing a bra, a surprise as she had fairly large breasts to begin with, though not overly so. But usually, I didn't see a lot of women running around without a bra on when she had breasts of that size, even though they'd been mostly hidden beneath the matching jacket she had worn in.

Once again she asked to use the restroom, heading off towards it as I again headed off back into the stockroom for shoes in her size. But this time, I remained there, peeking out around the corner, waiting for her return, and damn glad that I did so.

Jackie came out, settled herself down in her seat, and then quickly looked around. Satisfied no one was looking perhaps, even though I was, and could clearly see her from my vantage point, I then watched as she hurriedly ran her hand up between her legs. It was clearly evident she was doing something to herself, and I could only imagine what it might be, wondering if I would again hear that same interesting little sound I had heard the last time.

Moments later I returned carrying several pairs of shoes for her to try on and look at. I was pleased to see that she was wearing the sandals I had sold her the last time. As I lifted her foot, slipping the sandal off, I once again heard what I now knew to be the soft gentle hum of a vibrating toy between her legs. Rather than look confused or even pretend I couldn't hear it, I simply looked her right in the eyes and smiled. As I did, I placed my thumb squarely against the heel of her foot, and then slowly ran it up through her arch, massaging it as I did that.

"As with anything, it's important that you always have adequate support," I began saying now looking directly at her chest, her nipples very erect, twin little pin-points of arousal pressing against the almost painted on material of her tank top, the swells of each breast clearly showing above the somewhat low neckline. "Even when you don't necessarily need it," I finished still continuing to run my thumb deeply against the arch of her foot. "That does sound important," she said continuing to smile, though I heard a brief audible sigh as I continued massaging the sole of her foot.

"What you need is something nice and hard ... yet firm," I continued adlibbing this as I went, watching for her response, still hearing the faint hum of the toy which I now knew was buried deeply inside her. "But at the same time, something that is flexible and more than adequate for your needs."

I was blatantly fondling her foot, and she knew it, but allowed me to continue to do so. She even shifted her position somewhat, allowing me an even better advantage while continuing the massage and caress, though I now had and was given that "urban" moment, much to my surprise. I could see clearly between her legs, her short skirt bunching and riding up her thighs. I realized upon doing so, she wore no panties whatsoever, though if she had been when first coming into the store, she had obviously taken them off in the bathroom, which is when I also realized she must have inserted the toy. What I saw ... was a small silver end, a thin lead wire attached to it, leading away up through her waistband. I knew then she had the remote portion of it secreted away elsewhere, no doubt in one of her back pockets on the skirt, which I'd, noticed earlier.

"It's good to work out any soreness or stiffness before trying something new on for the first time," I then instructed. "Always good to get nice and loosened up a little."

"Yes ... it is," she agreed, hearing the pleasured tone in her voice. I wondered if she knew I had actually seen her toy partially buried inside her, and then lifted her foot just a little more working on her toes now, giving me an even greater angle at her crotch in doing so.

"Feel good?" I now asked, her eyes searching mine for a response.

"Very," she sighed pleasurably. "I always enjoy a good rub," she then added allowing the innuendo to hang there for a moment. "Don't you?"

"Oh yes ... as often as possible," I told her, feeling my cock already stiffening inside my pants, almost uncomfortably so now. "You take excellent care of your feet," I now mentioned replacing the foot I'd been working on, picking up the other, though I accomplished in doing what I'd set out to do too, the sudden shift in position revealing even more of her thigh, and now an even more obvious glimmer at the silver end of the toy barely hidden now beneath the hem of her skirt which had hiked upwards considerably.

"Thank you, I keep them nice and soft by putting a lot of lotion on them," she told me almost seductively.

"Yes, a nice creamy, natural lotion is always best for the feet," I agreed. Sliding my fingers between her toes as though fucking them, softly, sensually.

"The more natural, the better," she responded back.

"Couldn't agree more, and this one feels like it could use some too, it's a bit dryer than your other foot."

She pursed her lips in a small pout. "I didn't bring any with me," she stated. "I don't suppose..."

"Not something we keep in stock here I'm afraid," I said apologetically once again looking at her breasts, her nipples if anything even harder and more pronounced than they were before. I heard her giggle, almost demurely. "What?"

"I probably shouldn't be telling you this, but since I feel so comfortable with you," she began telling me, and continued before I could respond in kind. "But my husband lubricates my feet with his own particular brand of lotion ... if you know what I mean, so perhaps that's why they are as soft and smooth as they are. Though admittedly ... that foot seems to be a little neglected at the moment."

"I would imagine that IS good for the feet, amongst other things," I said smiling back at her.

"Yes, I uh ... enjoy using it there too," she told me. I felt her pull her foot away at that point, somewhat surprised as she did as she severed the contact between us, and in doing so, leaving me in a somewhat awkward state as I knelt there in front of her. There was no way I could stand without revealing the massive erection I was now sporting, so I did the only thing I could think of to do, and that was to reach over and grab one of the shoes from the box sitting next to me.

"Before you try that on me..."

I looked up at her, her face was one of pure lust.


"Maybe ... you wouldn't mind applying a little of that same kind of lotion my husband uses," she boldly stated letting me know in an instant we were past giving innuendos here, or dancing around the subject as we had been. "How long do we have?" she then added.

I glanced at my watch, Larry wasn't due back for another twenty minutes, though that didn't mean he still couldn't return at any moment, he'd done that before. But even more importantly, were the other customers. Two had come in, looked about, and then left since she'd got here. No doubt there'd be more too, and I couldn't very well just take my cock out, jerk off onto her foot in hopes of getting away with it ... or could I?

"You ... keep an eye on the door, let me know if anyone comes in," I told her, as I reached down, still squatting in front of her, unzipping my fly. She squealed with delight at the sight of my rigidly hard cock as I fished it out and began pumping it. As I began working my prick, I saw her reach behind, a moment later retrieving what I'd confirmed earlier. With the remote now in her hand, she turned up the control to the highest setting, the whir, hum and vibration of the toy inside her cunt now readily apparent.

"Hurry!" she half demanded. "I won't last long at this setting, and I want to feel your spunk spurting against me when I come!"

I was nervous as hell, yet excited beyond belief. Never before had I ever done anything as outlandish as this inside the store. Kneeling there before her, a bird's eye view of her gorgeous bare pussy, her slit now glistening with moisture as it seeped out of her, fisting my prick with the danger of Larry, or worse ... customers who could step inside the store at any moment now.

Ironically, depending on how you wanted to look at it, I was almost there already.

"Here it comes!" I announced, leaning forward a little, holding onto her foot, my prick tip pressed against it as I began squirting out what felt like a gallon of rich creamy juice against the sole of her foot.

"Yes! Yes! Yes!" she cried out in delight, her eyes wide watching, and feeling my spunk bathing her foot entirely. She came as I did ... thrashing about in her chair for a moment. Had anyone come in, there'd have been no doubt in their minds ... and certainly not in Larry's as to what had just happened. Thankfully, she turned off the toy, composing herself as I hurriedly slipped my cock back inside my pants. But her foot was still drenched, covered in thick gobs of gooey cum-cream. "Hmmm, now ... rub it in," she asked softly, pleasurably. "Too bad we didn't save some for the other foot ... but, perhaps next time. Next week?" she asked obviously still aroused.

"Yeah, we'll do the other foot next time if you'd like," I responded quite contentedly.

"What about the other guy?" she then asked.


"Yeah ... would he be inclined to help out?"

"Oh ... I don't think there's any doubt about that," I told her. "I'm sure he'd be more than delighted to see to your other foot while I do the other one, if you'd enjoy that."

"I would," she said smiling. "Next week then, same time?"

"We'll be here," I said grinning back, already wondering what Larry would think when I told him, or even if he'd believe me when I did.

Jackie took the shoes without even trying them on, sliding her still cum covered foot back into her sandal. She followed me up to the register as I worked up the purchase, which again is when Larry walked in. Jackie smiled at him, giving him pause for a moment as he smiled back, and then looking at me curiously. I knew he remembered her from before.

"Next week then," she said winking at me, and then winking at Larry, which really confused him, causing me to laugh.

"Ok ... so maybe you were telling the truth last time she was here," he said after she'd left. Which is when I then told him what had just happened.

This time ... he believed me.

Larry and I were both with customers when she came in, though I had already gotten the feeling that the woman I was helping was mostly window-shopping, so I hurriedly excused myself and approached Jackie. She greeted me with that award-winning smile of hers and actually leaned forward giving me a brief kiss on the cheek. As she did that, I felt the press of her full breasts against my arm. I could have stood there forever, feeling the electrical charge between us, but there were still customers inside the store.

"Have a seat, we'll be with you as soon as we can," I told her. She immediately headed back towards the restrooms as Larry finished ringing up his sale at the register. I stood by watching my non-sale browse for a moment longer, finally walking out as Larry rejoined me, the two of us standing there looking over towards the restroom.

"Damn ... this is for real?" Larry asked as we headed back towards the seating area.

"I wasn't kidding my friend, but we're going to still have to be careful and keep an eye on the door here ... but yeah, she loves cum on her feet just like I told you!"

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Story tagged with:
Masturbation / Exhibitionism / Voyeurism /