If the Shoe Fits: A Shoe Fetish Story


If the Shoe Fits: A Shoe Fetish Story

Summary: Shoe obsession leads to submissive sexual exploration.

Note 1: This is dedicated to Kevin, who requested this fantasy.

Note 2: Thanks to Tex Beethoven for editing this story.

If the Shoe Fits: A Shoe Fetish Story

There are two things I love to do every day: work out and jerk off… although it’s usually 1. Jerk off, 2. Work out, and 3. Jerk off again. Repeat as needed.

I work out at a local gym run by two of the nicest and hottest people I’ve ever met: Mike and Roxy Jackson. They also happen to be my next door neighbours. Well, actually my parents’ next door neighbours I suppose, since I only live there in the summer… the rest of the year I’m away at college.

I’m 21, pretty good looking, with blond hair and blue eyes, 5’7″, in great shape, and I have an impressive 8-inch cock that had gotten me pretty popular in my college life. Yet my most constant jerk off fantasy was Roxy.

Roxy was in her mid-thirties, tiny at 5’1″, and weighed only around 115 pounds. Yet she had a huge bust, that looked out of place on her petite but muscular physique. She had long, raven-coloured hair, and piercing dark brown eyes. She had a few tattoos as well, as she found a way to mix sexy and tough in a way I hadn’t ever seen before. Her attractiveness was enhanced by the fact that whenever she wasn’t working out at the gym, she always seemed to be wearing nylons, which really showcased her amazing legs, as well as high heels that added five inches to her height.

Her husband Mike was all muscle… shaved head… tons of tats… and super friendly… considering that he looked like he could crush you with just his hands. In fact he probably could… he just wouldn’t.

Anyway, I’d met Mike and Roxy many times, but I’d never really hung out with them much… due to our age difference I suppose… although I’d learned that my parents had been hanging out with them a lot ever since I’d moved away from home.

This summer I resumed working out at their gym, partly to stay in shape, and partly to eyeball Roxy, who wore heels, nylons and short skirts at work (unless she was working out)… I assume because she knew she had an amazing body so why not flaunt it… but I imagine her outfits also brought in some horny guys, and perhaps also horny lesbians.

She often wore wedges, often with open toes, so I could keep an eye on her cute toes, and I imagined sucking them into my mouth, or better yet, wrapping them around my cock.

An aside: I can ejaculate amazing cum shots… I have a cannon of a cock… having a personal best of shooting my cum as far as six feet… since as a dedicated jerkoff artist and a wannabe athlete, I constantly practiced my craft and measured the results.

Twice during the first two weeks I was home, my parents went next door for the evening… my mother dressed in sexy attire, which was very unlike what she typically wore. It was strange, but I didn’t put much thought into it. I was just happy for them they were going out… even if I was surprised they didn’t get home until after two in the morning… about four hours past my mom’s typical bedtime (she was normally early to bed and early to rise).

It was a couple days after my parents had left for a week-long trip to the lake for their twenty-sixth wedding anniversary getaway, when there was a knock at the door.

I opened it, and saw Mike and Roxy standing there. I politely invited them in, even as I took a sly glance at Roxy’s very ample cleavage and down to her feet… disappointed to see that she was in jeans and not nylons… but on the other hand, she was wearing what I think were 6-inch platform open-toed wedges… which meant I could see her freshly-painted red toenails, which were far from disappointing.

Mike asked, “Will you do us a favour, Kevin?”

“Sure, anything at all,” I said, actually hoping to do anything at all for Roxy. Suck on her toes, lick her pussy, worship her tits, eat her ass, whatever. And the word ‘whatever’ encapsulates a very long list. This was a woman who deserved to be worshipped for an eternity!

“We’re heading out of town for the weekend to a fitness conference, and we were hoping you could drop over a couple times or so and check on Bella,” Mike requested.

“Sure, no problem,” I agreed, Bella being their Siamese cat.

“Come on over right now if you would, and we’ll give you a key and show you where everything is,” Mike said.

“Sure,” I agreed, and I followed them across, my rear-view vantage giving me an amazing and lengthy look at Roxy’s ass as I did. Her usual skirts always presented me with ample opportunities to admire her legs and feet, but her jeans right now allowed me to admire a part of her body I seldom got to see showcased. She really did have a perfect body.

Roxy gave me a tour of the house, seeming to notice me admiring her kemalpaşa escort tits, ass and feet, but not saying anything about it… although her warm smile implied she knew… and enjoyed the attention.

Anyway, I returned with their keys and a hard-on… which I dealt with the minute I was back in my bedroom.

Day 1

The next afternoon I went and checked on Bella. I fed her, gave her fresh water and some pets, which she seemed to enjoy.

I was about to leave, when curiosity got the best of me, and I decided to look around after seeing a couple pairs of Roxy’s sexy shoes by the front door. I knew it was wrong, yet I couldn’t’ resist.

I went into their bedroom, feeling a little guilty at what I was doing, but I was being led by my lower head.

I looked in her dresser drawer, and found sexy panties and thongs, garter-belts and stockings.

I noticed their laundry hamper, and walked over to it, finding only a few items, including a blue pair of panties… the ones she must have been wearing yesterday while touring me around the house in those wonderfully tight jeans. I brought them to my nose and sniffed.

The scent was light, but it had me in complete lust.

I went to her walk-in closet, saving the best for last. I opened the door, and stared at four shelves, filled with some of the sexiest shoes and boots I’d ever seen… recalling seeing her wearing a few of the many pairs.

My entire body was trembling with excitement, as I bent down and picked up the pair of wedges Roxy had been wearing yesterday.

Before I even realized I was doing it, I had moved her shoe to my nose and was smelling the essence of her beautiful size six feet.

I inhaled deeply, as if I was taking my last ever breath, which made my cock harden like a steel beam.

I rubbed my cock through my shorts as I continued smelling her unique… exotic… enticing… scent.

Knowing she wouldn’t know I’d taken it since they’d be gone for a couple of days, I grabbed one of the wedges, put it in a grocery bag, and returned home.

Once there, I opened my laptop, turned on some hot hardcore porn with a girl in heels and nylons getting fucked, and I got undressed. I stroked my cock with one hand, while I licked and sniffed the sole of Roxy’s freshly worn heel… and I came within about thirty seconds. Pathetic… but the sweet, sweet, yet tangy taste of Roxy sweat was just too much. Truth be told, I hadn’t really watched any of the video I had turned on.

Feeling guilty, I put the wedge back in the bag and decided to return it tomorrow.


Day 1… later that night.

Although I didn’t need to check on the cat again, I did need that other wedge. So I went over, petted the cat briefly just to convince myself I was actually doing the job I’d been requested to do, and retrieved the other heel… hoping for a fresh scent and taste. I quickly left like a twisted thief in the night, and returned to my bedroom for a second round of erotic shoe play.

This time I didn’t even bother to put any porn on, as I sniffed and licked the second wedge while furiously stroking my cock, and I did something I’d only done one other time… at my friend’s house and into his mother’s heel… I aimed my cock into her other heel… so many times had I fantasized about her slipping her foot inside of it and sliding into my cum.

Pounding my cock, I focused on spewing a massive load into her wedge. I lasted a little longer than last time… by maybe a minute… before exploding all of my white seed inside her wedge.

Once again, once my orgasm had subsided, I felt guilty.

This was so wrong.

I grabbed some tissue and cleaned the wedge as best I could, as I shook my head at how I had just disrespected Roxy.

Day 2

I’d like to say I fed the cat, gave her a few pets, returned the wedges and left… actually I did all those things… although I did something else before the leaving part.

I went back into Roxy’s bedroom and into her laundry basket, dug deeper, and found a pair of her pantyhose, which I put in my pocket. I grabbed another pair of wedges, taking a whiff and discovering she had recently worn these ones as well, and I headed back home.

In my bedroom, I put on some porn again, and being curious, having always wondered and been tempted, but never before actually following through, I got undressed and slid into the sheer, silky pantyhose. It took some time, as I discovered it wasn’t remotely like pulling on a pair of pants.

Once they were on, I rubbed my hands up and down my legs, in awe of how silky sheer they were, and how sexy the pantyhose made me feel. I couldn’t explain it, but in a sudden moment of clarity I felt an awakening of my feminine side; something I hadn’t known I had.

A little unnerved by that, I rubbed my very hard cock (which wasn’t at all feminine of course) through konak escort the sheer nylons, and I wondered what it would be like to stroke my hand up and down Roxy’s amazing legs… plus her perfect ass, and especially her sexy as fuck feet.

Feeling so horny, I pulled the pantyhose down a bit to release my cock, as I sniffed and licked inside Roxy’s six-inch left wedge.

Again I stroked my cock, as I licked the sole hungrily as if it were a melting ice cream cone, while I jerked my cock inside the other wedge.

I held back as long as I could… which was perhaps only two minutes… a new record because of the Roxy wedge in my hand… before erupting a huge wad inside of it.

Still horny, still crazed with lust, a new twisted idea popped into my head. Something I’d never seen in a porn film, or even pondered until this very moment… WHAT WOULD IT FEEL LIKE TO STICK MY HARD ROD INTO THE TOE OF THIS SEXY SHOE AND ACTUALLY FUCK IT LIKE A PUSSY?

The question now in my head, I needed to find out the answer.

Using my own freshly deposited first load, I squeezed the head of my cock between the thin toe straps, and began slowly moving the wedge back and forth on it.

As strange as it might sound to anyone who hasn’t done this, the sight of my cock moving back and forth inside that beautiful shoe was insanely sexy.

It felt a little like being inside a woman’s pussy… yet also completely different.

Because it was so taboo… so wrong… so kinky… it actually felt better than it should have.

Yet although it was an amazing sensation, I didn’t want to use the shoe as a masturbation device, I wanted to actually fuck the shoe.

I wanted to fuck the wedge like it was a pussy… like it was part of a woman.

I wanted to truly fuck it.

I went to the bathroom and placed the wedge on the sink, which just happened to be the perfect height, and I began to fuck it.

I smelt the one wedge, Roxy’s sweet scent adding to the stimulation and my exhilaration as it filled my nostrils, sending my entire body into overdrive.

I tightened the strap for maximum friction, as I pictured Roxy’s sexy feet encased in mocha-coloured stockings.

I lasted a little longer than I might have because I’d just come, but in a few minutes, I was unloading a second load into Roxy’s surrogate pussy. It felt so amazing… it felt like I had just actually fucked a girl.

Spent, I cleaned my cum out her shoe, and went across the room to do some online gaming.

Yet around midnight my cock was hard again, so I figured the Jacksons’ cat could use an extra treat.

So, I went back to their house, and after giving the cat a treat… so I could at least defend honestly why I was there this time if challenged… I went back into their bedroom.

I rummaged through Roxy’s dresser again, more thoroughly this time, and I found so much sexy lingerie there, including mocha-coloured old-fashioned pantyhose with a seam down the back, garter-belts and stockings, and even crotchless pantyhose. Fuck, the thought that at any time I’d seen her she could have been wearing crotchless pantyhose under her skirts and dresses, had me ready to bust a nut again.

I went into the closet, grabbed a pair of red six-inch pumps… there is just something fucking sexy as hell just about red heels, but six-inch ones?

So horny, I climbed out of my shorts and underwear, lay down on their bed, and sniffed inside the heels while I slowly stroked myself.

Her scent was so exotic… so subtle… but also captivating. I could imagine what it would be like to sniff those heels the very moment she had slipped her moist feet out of them.

I loved the smell of a pussy, but there was just something I couldn’t explain that really revved my engines, as I became entranced by the scent of her heel.

The red pump didn’t have an open toe, so I couldn’t fuck it. I could have gone and found another pair, but instead I got on my knees on the bed and sniffed one of the shoes while pumping my cock, and again aiming for the open target.

As usual, I didn’t last very long before shooting a big load directly into the shoe.

Spent, I quickly got dressed, but exhausted, I ended up crashing on their bed instead of going home.

Day 3

I was awakened at noon, when my phone rang. I was confused about my surroundings until I realized where I was.

I panicked; they were coming home today.

I reached for my phone and said, “Hello.”

“Hi, Kevin, ” a sexy feminine voice greeted me.

“Oh, hi,” I said, instantly wide awake. It was Roxy.

“We’ll be home in about three hours; can you please check in on Bella once more?” Roxy asked.

“Sure,” I agreed.

“Thanks. We owe you,” Roxy said.

I thought of the many ways she could repay me, but I answered simply, “Oh, it’s been no trouble at all. Happy to do it.”

“I’m glad. See you soon,” she said.

“Sounds good,” I replied.

“Have kuşadası escort fun,” she said, then she hung up.

Realizing I had limited time remaining alone with her shoes, and figuring I should heed her advice and ‘have fun’, I went back into her closet, and found another sexy pair of shoes: these ones were black, open-toed five-inch sling backs.

Realizing this might be my last chance to do this forever, I decided to go all in. I grabbed a pair of her crotchless pantyhose, and after getting completely naked, I put on the mocha pantyhose and began caressing my legs. Fuck, it’s a real shame that pantyhose are considered a female only piece… like who the fuck decided that?

Same with heels!

I grabbed the shoes, and went into their master bathroom.

I stroked my cock slowly… allowing some precum to leak out, as I sniffed one heel while I placed the other on the bathroom sink.

The sweet scent had my balls boiling, and I used my pre-cum to lube the peep toe opening. It was a tight fit, tighter than the MILF ass I’d fucked when I picked her up at a bar a couple weeks ago, but once I was in, I slowly fucked it.

God, it was heaven.

I wanted to really enjoy this fucking, knowing I had a couple of hours before I had to make sure everything was back in place, so I took my time.

At least I did at first.

After a few minutes, I couldn’t control myself any longer, and I began to really pound that heel, using both of my hands to hold it in place.

“Oh fuck,” I groaned, as I exploded my load inside my creative fuck toy.

“Shit,” a male voice… not mine!… said from behind me.

I looked up into the mirror, even as more of my cum spewed into the shoe, to see Mike and Roxy standing in the doorway, staring at me with looks of disbelief on their faces.

“Huh,” Roxy said, looking at me, with not with the complete shock and disgust I’d expect, but… ‘intrigue’ would be the word I would use.

“I-I-I’m s-s-so s-s-sorry,” I stammered, every word stemming from my being caught in the act in the most humiliating fashion ever… even making Jim fucking a pie in American Pie seem tame in comparison… a movie series my buddies and I had watched again just a couple weeks ago.

“May I please have my shoes back?” she asked surprisingly mildly, as she slipped out of the wedges she was wearing and revealed her newly painted toes, once again ruby red, encased in sheer black nylons… making my cock, still throbbing, leak out a little more cum.

“S-s-sure,” I stammered, completely humiliated, and yet now becoming a little confused by their unfussed reaction.

I pulled my cock slowly out of the shoe, and handed her the cum-filled heel.

“The other one too, if you please,” she ordered politely, but nonetheless it was an order.

“Yes ma’am,” I replied, also handing her the clean shoe… which was now super clean after my tongue-licking.

I watched in shocked awe, still wearing her crotchless pantyhose as she slipped into her heels… deliberately sliding one of her stockinged feet right into my big… fresh… hot… load.

Roxy walked over to her bed and sat down next to me asking point blank, “How long have you wanted to fuck me, Kevin?”

“Yes, how long have you wanted to fuck my wife?” Mike reiterated, having been completely silent this entire time until now. Unlike hers, his tone was a little scary.

“Um, I, um…” I struggled to find an answer.

“Relax, son. It’s not a trick question with a calamitous answer. Everyone wants to fuck my wife,” Mike elaborated, suddenly sounding far less scary.

“Not everyone,” she said coyly, as she dangled the heel containing my cum from her toe.

“No, maybe not the priests and nuns of this world,” he chuckled, seeming amused and relievedly okay about my obsession with his wife.

“Actually, I have had a nun or two go down on me, but I’ve only fucked one priest,” she pointed out, still dangling that shoe like a hypnotist’s watch… that impious visual making my cock flinch, dying to hear those stories.

“See? Everyone does,” Mike laughed as I remained outwardly stoic, and hard in every way conceivable.

“So, what were you thinking about while you fucked my shoe?” Roxy asked, looking directly at me, and glancing down to my hard cock, which was still raging… and which had no intention of going down anytime soon.

“You,” I answered sheepishly.

“Of course. But what about me?”

“Yeah, f’rinstance were you thinking about fucking my wife?” Mike asked in a stern tone that scared me a little bit again… okay a lot… since he could break me in two without even breaking a sweat.

“N-n-no,” I lied.

“You don’t want to fuck me? Not even a little?” she asked with a bit of a pout.

“Oh,” I groaned, giving her my answer without actually answering.

“Or to eat my pussy?” she continued, obviously really enjoying the power she wielded over me.

“I, um….”

“Or perhaps… and I think this one should be closest to home… to slide your cock between these sexy nylon-clad feet?” she asked, as she dropped both of her heels to the floor, leaned back on her bed a bit, and offered up both of her soles… including the one that was cum-coated. The black nylon made my white goo on it very visible.

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