High Heels

I was around eighteen at the time. I was going through my rebellious, pot smoking phase and never really wanted to be around my family, so I basically lived with my best friend, Jon. 

He lived in a condo downtown. We just hung out, smoked, and played video games all day and night. 

It was a lot of fun.

This story takes place during the summer post junior year. As I said, I was essentially living at Jon’s place at this time. So, let’s get to the point.

Jon’s mother was a smokeshow. Her name was Donna. She was probably in her mid-forties at the time, so pretty old for a smokeshow, but man was she fine.

Honestly, think Sharon Stone. 

That is an accurate description of how hot she was.

She had mid-length blonde hair, a fit body, roughly C cups, a tight ass, toned legs, and the sexiest, most beautiful size seven feet. 

Despite her age, they were so soft looking and just plain lovely to behold. She also was always perfectly pedicured.

She was a high-end business woman, always wearing form fitting female suits and all manner of heels.

It was the heels I loved most.

However, as hot as she was, she was a complete bitch. You have not met a bitchy woman until you have met this one. She was super uptight from her job. 

She was up Jon and I’s asses all the time. If she knew half the shit we got up to Jon would have been grounded for years. 

Hell, she probably would have grounded me too. However, honestly this just made her hotter in my eyes.

Watching this intensely authoritative milf with amazing feet yell at us got me hard every time. 

One day after she finished yelling at us for God knows what (it is far too long ago to remember those specifics) Jon was super pissed off and decided to go take a shower. 

Jon took really long showers, especially when he was pissed off. Donna had run to the store (right down the street) to grab a couple things.

As Jon was in the bathroom, a crazy idea came over me. I was rarely alone in the house, but still I was shocked that I had not thought of this before. 

I decided to go into Donna’s room and take a look at and maybe even touch the heels I so enjoyed staring at on her beautiful feet.

I snuck quietly into her room, terrified of getting caught. What if Donna came back in? Or Jon got outof the shower? But I was lost to reason at this point.

I opened her closet and there was her collection of heels in all their glory. 

I went through them slowly, caressing them, bringing some to my nose and smelling them, the sweat and perfume so intoxicating. 

It felt so good to be able to finally smell the feet I had fantasized about for months.

I finally found a pair that was familiar. It was a pair she wore quite regularly and was also one of my favorites. 

They were a pair of beige open toe shoes with a decent heel on them. Whenever she wore them they displayed all ten of her perfectly pedicured toes.

I picked them up and took my dick out. I had not originally been planning on masturbating but I could not help it at this point. 

I put one heel to my face, burying my nose where I could see the imprint of herbig toe. I started intensely licking the indent. I could taste the sweat and suede mixed together. 

It was amazing!

I put the other on my dick and started furiously rubbing it against the head of my dick so hard that it hurt.

But the pain was nothing compared to the pleasure as I continued rubbing. I was imagining Donna was there rubbing her heel clad foot all over my hard cock.

As I continued to rub I knew I was close to cumming. I did not know what to do as I had not brought tissues or anything with me. 

As risky as it was, I knew what I must do. I took the shoe away from my face and I held both heels right in front of me and shot a huge load of cum right into them, drenching them. 

I watched it seep in and fill the indents made by her perfect toes.

As the euphoria began to fade I immediately started to panic. 

What was I going to do? What if she noticed? Would she know it was me? Of course she would. Who else could it be? Her own son? No, she would obviously know it was me.

I pulled up my pants and ran out into the kitchen and grabbed a roll of paper towels. 

Returning to Donna’s room, I wiped up the cum as best I could. However, by this point it had for the most part soaked into the suede of the shoes. 

I put the shoes back where I had found them, positioning them slightly differently so they were partially hidden from view.

I slipped from the room, threw out the paper towels and sat down on the couch. 

I was still terrified, but hopeful that once the cum dried it would be indistinguishable from the sweat already staining the shoe.

Despite my fear, the fact that I had just came in Donna’s heels, my best friend’s bitchy businesswoman milf of a mother turned me on immensely. 

I was already getting hard again. 

Moments later, Donna came back through the door carrying groceries. I immediately ran to help her, carrying the bags to the kitchen.

Shortly afterwards, Jon got out of the shower and he and I went up to his room to smoke and game and what not.

A few days later, as Jon and I ate breakfast I could not help but smile. My cock was growing rock hard as I watched Donna leave for work wearing that very pair of heels that were now soaked in my cum. 

In the months that followed I probably came in every heel that Donna owned.

She had to have noticed at some point, but she never said a word. She did however wink at me once when she got home from a shopping trip and I saw her unload a new shoe box, filled with brand new heels. 

Needless to say, those were came in as well.

Story by Kai

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