Jackie's Shoes Ch. 01

The day had started and proceeded as any day usually did. I had taken a run first thing, put on my suit and worked for the day, and before I was going to head home to watch some sci-fi reruns, I thought I would hit up the mall for some window shopping and a smoothie.

I ended up finding a quiet spot on a bench in front of a woman's shoe store. After I sat down I found that it was probably the best spot in the mall for a guy such as me to sit. I have a bit of a thing for women's high heel shoes. No I'm not one of those guys that likes to stroll around in them, I prefer to look at them and adore them while they are on women's feet.

Berry Madness goes well with indulging in a voyeuristic shoe fetish I found out. I sat there for quite some time, enjoying the wide variety of women and the shoes they were trying on. If I had a preference, I would say that stiletto heel really gets me going, and there were many to ogle while I sat there. Woman after woman went in and paraded around, all the while blissfully unaware of the effect they were having on the my crotch.

Nearing the time I had planned to leave, a particularly stunning woman with long black cascading hair entered the shop. She casually walked in wearing a somewhat business like pencil skirt and a matching yet revealing top. She wore a sexy pair of black satin peep-toe stilettos, lemme tell you, the whole package made my cock jump. She checked out the new stock and some of the older stuff as well, picked up a few, smiled and then walked behind the counter to chat with the woman tending the store. After a hug and some smiling banter I concluded that they must have been good friends. A few minutes of catching up saw them turn their attention in my direction. The stunning woman grinned and they let out a chuckle. It seemed as though my time sitting there had not gone unnoticed.

I began to gather my things as the woman walked out from behind the counter and made a bee-line for me. As I stood up to leave she blocked my escape route. She was a towering woman, a good 6'2" in her shoes. "Have you been enjoying yourself?" she asked me.

"Umm sorry what? I was just leaving, didn't mean to interrupt your shopping" I said in a panic.

She smiled, grabbed my upper arm, and said "My friend has told me you've been sitting here staring at the women for quite some time".

"I was just enjoying an after-work smoothie and found the bench to sit on. It just so happened that the store is frequented by a lot of attractive women and me being a guy, yes I enjoyed it quite a bit".

She laughed and tossed her hair. "Well, come join me back in the shop for a few minutes".

Silently I allowed myself to be pulled into the store by the woman that was making me as still as a flagpole. I was taken past the displays right to the counter. She introduced me to Stacey, who turned out to be the owner and then introduced herself as Jackie. She then told Stacey to grab a few boxes and ring them up. "I'll tell you what, since I can see how you are enjoying me, let's make a deal" she said staring at the very visible bulge in my pants. "Put these on your credit card and I'll model the shoes for you as a way to pay you back".

I laughed in an awe-struck way and said "Are you kidding me? Those are $400".

"Believe me, it's worth it" Stacey said leaning over and smiling.

"Just do it, or stop wasting my time" said Jackie, apparently getting impatient.

Like a mindless idiot, I did it, I pulled out my credit-card and paid. The strange thing was that I sort of enjoyed it, and it kept me hard so maybe I was doing something right.

Since the mall was closing and we needed to get out and leave Stacey to do her thing, Jackie and I exchanged numbers and I gave her my address. She said she would be over shortly since she lived not too far from me and needed to go feed her fish or something. With that she hip bumped into my raging hard-on and smiled wickedly.

I went home in a daze, unsure of what had just happened. I was oddly excited and my heart was racing to see Jackie once again, modeling the shoes that made me weak.

After an hour or so, there was a knock at the door, I eagerly answered it. I managed to stutter a hello to which she grinned and stepped in. She was wearing a long coat and as I glanced down I saw she was wearing a sexy pair of high-heeled boots, the ones I had purchased for her earlier. Seeing them made my cock twitch.

After she walked in I offered her a glass of wine and made some uncomfortable chit chat about the weather and the neighborhood. I could help but stare at her, all of her. Seeing my obvious gawking, she removed her jacket and sat down on the sofa with a smile.

She was wearing a short black skirt with black fishnets. The stiletto heeled boots came to her knee and were made of a patent leather like material. She also had on a black long-sleeved sweater with a bit of a turtle neck, and it did absolutely nothing to hide her enormous tits. She had also done her hair since the last time we chatted, it was long, black, and flowed easily over her shoulders revealing just a peek of her supple neck. The makeup she wore was the perfect accompaniment for her outfit, dark smoky eyes, deep bold red lipstick, and an overall look of a power-slut that seemed to only have one thing on her mind.

"So what do you think?" she said, tapping a French-tipped fingernail on the top of her boot.

I managed to stutter out "Wonderful..." in an uncomfortable tone.

Jackie laughed and took a sip from her wine glass. Trying to relax I took a seat on the love seat adjacent to the sofa and had a decent gulp of wine myself.

Looking out the window into the night she stood up and then turned her gaze on me. I sat frozen by her beauty and the intimidation she bore into me. She sauntered over to where I was sitting, lifted her leg, and placed the boot between my thighs. I looked up at her and with a swift motion she thrust the boot into my crotch. I winced in pain but did not move. I could feel her wiggle foot against my hardon, it was a new but definitely exciting feeling.

"Boy, do you see what being nice to women brings?" she whispered.

I nodded and choked out a "Yes Maam".

She responded with a disappointed look and said "Just Jackie for now boy".

Again, I simply nodded.

After she had finished her wine she looked down at me and pressed her boot into my hardon again. "You are quite the sick little fucker aren't you... take it out and show my how much you enjoy my company."

I unzipped my pants and struggled to take out my rock hard cock, now pulsating in anticipation of attention. Considering she would not move her boot, it was a tough process. My member stood ready and waiting just above her boot, oozing precum.

"Wrap your hand around it and stroke it for me"

In a flash my hand obeyed her command. I was so close to cumming already it would only take a few strokes to paint her boot with my semen.

"STOP" she said in a stern voice. "Don't touch it again until I say you can, tonight, it is my cock."

My hand fell to my side and my cock twitched in disappointment, I had been mere moments from relief. She was indeed an interesting woman, I was beginning to wonder why I had never met someone like this before.

She pulled her foot out from my crotch and stood before me staring me down. "Good boy, now, I will be right back, do not touch that cock or you will never see me again - our little fun gone forever." With that, she placed her empty wine glass on the coffee table, picked up her bag, and strode out of the room to the washroom down the hall.

I sat there for what must have been 20 minutes with my raging hardon jutting out of my pants while I listened to the occasional sound from down the hall. Just when I was starting to think about touching myself I heard Jackie emerge from the washroom.

Into the living room she walked, the hottest thing I'd ever seen. She had put her hair up into an updo, adjusted her makeup into an even more evening whore look, and had removed much of what she wore. I sat staring at a statuesque goddess clad in a red and black corset, thigh high fishnet stockings, and a new pair of shoes – black and red platform stiletto peep toes, the perfect CFM shoes. My cock leaped when I saw her, and she definitely noticed.

Jackie stood in front of me and grinned. She posed a few seductively dominating stances and turned to once again sit on the sofa. "Bring me another glass of wine boy, and leave that cock the way it is remember."

I quickly nodded and got up to get her glass and walk back to the bottle. My pants began to fall while I walked and after I had refilled her glass I reached to pull them up but she interrupted me and said "Don't you think about it, if they fall they fall, you will walk with them at your ankles if you can't keep them up."

I removed my hand and headed back to give her the refilled white wine she seemed to be enjoying. Half way to her, my pants were at my ankles and my stiff cock was leading the way ahead. It was deeply embarrassing and I'm sure my facial colour showed it, not to mention my renewed stiffness.

"Thank you boy" she said as I passed her the wine, "and take off those pants altogether now".

"Yes Jackie" I said quickly removing my slacks and tossing them into the corner.

"Get rid of those socks you idiot" she said, clearly unimpressed as the apparent cardinal sin.

"Yes Jackie", and I sent the socks the corner as well.

She then pointed to the ground in front of her crossed legs with a stern, cold look in her eyes. Taking her instruction, I fell to my knees on the spot where she was pointing. We sat frozen for several minutes, her sipping her wine and looking out the window with me staring at her up and down struggling to avoid touching my hardon.

"Do you like the way I look boy? Do you enjoy looking at me and thinking those naughty thoughts your are having? she said in a calm tone without looking at me.

"Yes Jackie, quite."

"Good, and I want to make sure you fully enjoy yourself to my satisfaction. You are going to masturbate now, onto my shoe that you so thoroughly enjoy, then you are going to lick it off."

I coughed in uncomfortable silence, internally disgusted and managed to choke out a "Yes Jackie..."

"Then do it."

Gripping my cock I worked it fast and furious, staring at her shoes. I was enthralled by her stockings, her shapely legs, the colour of her corset, and the vision her face was. She had become my living fantasy. My hand was a blur as the anticipation of climax had been built for a solid hour.

She was looking at me now, I could see her breathing deeply. I watched her chest heave between glances at her ankles or shoes. I had become a fetish crazed beast, what had she done to me?

With a grunt and an orgasmic full body spasm, I came an enormous load onto her shoe, painting and coating it with a thick layer of my passion. In my post-cum bliss I stared into her eyes – then, she rose her eyebrow and looked at her shoe.

Cringing, I bent over to her shoe, pressing my tongue into the patent leather. With every lick and suck I felt diminished as a man, but to my surprise, I was getting hard again...

Jackie smiled and I could hear her laugh under her breath, a wonderful, girlish laugh of eager amazement, because she knew at that moment, she owned me through and through.