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.

.... There is more of this story ...

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Story tagged with:
Masturbation / Exhibitionism / Voyeurism /