Literotica Heels Stories

351,886 results
Orientation
Length
Source
Infinite Scroll

My Heels

by shoeslayer on Sep 16, 2017
Fetish

Another day, my lover is already on his way to work as a locomotive electrician for the railroad. The sun shines through the curtains of my bedroom and the birds are chirping. I am in a great frame of mind today, last night my lover told me what my heels do for him. The way he told me he, was getting me turned on! and his husky voice had a lot of feeling w...

Masturbating to a Woman in Heels

by Sexybeast8899 on Aug 28, 2018
Fetish

About two years ago I placed an ad on Craigslist. The ad was placed in the casual encounters section. The ad was asking if someone would let me masturbate in front of them. I asked in the ad that the woman be willing to wear high heels and let me look at their legs while I masturbate. I'm an attractive man. I'm about 6'1". I have a good body. I'm fit and I...

The Garage Sale

by Iamhypnobyheels on Dec 2, 2019
Fetish

I enjoy going to garage sales. It's something to do on a quiet Thursday or Friday afternoon when the wife is still at work. And you never know what you may find. For me, old baseball cards, usually thrown into a box without thought. For 5 bucks, you may get $500 or more in value. The owners just want them out of their house. Last Thursday I was doing what...

Snapped!

by Redheelfantasy on Sep 16, 2017
Fetish

As I gazed from the entrance of the parking garage to the marble floor of the catwalk, all I could think of was the heels I was wearing. Being a pharmaceutical representative, I had to attend many a conference and meet with local doctors and fellow nurses. The convention this quarter was in a suburb of Chicago, and this meeting would allow me the opportunity...

Cottaging CD

by Highheelfun on Sep 16, 2017
Transsexuals & Crossdressers

I'm now in my fifties but for as long as I can remember, I've had a fetish for heels and nylon stockings. When my parents were out I would sneak into my mother's wardrobe and try on her stockings and high heels. I sometimes used to dress further with her girdles and party dresses. This always ended with my cock being rock hard and me wanking, trying to make...

Co-Worker in Come-Fuck-Me Heels

by Sexybeast8899 on Aug 22, 2018
Fetish

I have worked with Katie for about 5 years. We work at different offices in different cities. I talk to her on the phone about once a week. Katie is in her late 20's. She is married and has two kids. She is about 5'7" and weighs about 120-130 pounds. She has a very good body. She has long brown hair and brown eyes. Katie works in our headquarters and I w...

New Management

by 510col on Apr 1, 2020
Fetish

Chapter 1 Monday AM Helen got out of bed and showered ready for work. She was looking forward to the day ahead with some trepidation as her office, something of an outpost of empire, was expecting a new boss to be appointed. A thrusting young manager was being sent from Head Office to get their business back on track. They say that a new broom sweeps clean,...

Shopping Trip

by PhRedSonya on May 21, 2019
Erotic Couplings

Author's note: This story is dedicated to my sweet friend Michael. *** I sit at my makeup table making myself ready, and I have to continually be mindful of my hand wanting to drift down to my crotch and begin rubbing myself. We have been emailing quite steadily and finally we are going to meet in person, so you can take me high heel shopping. The fact t...

Chris & Cindy

by cbf316 on Sep 16, 2017
Exhibitionist & Voyeur

Cindy who was a teacher at Chris's school was none to happy with him. About a month ago out of the blue, he broke up with her niece Lisa and Cindy was none too happy in the way he did it. He blew her off a week before her prom and Lisa had taken over two months to recover from the blow. Now Chris didn't know that Cindy and Lisa were cousins. Cindy was a f...

Admiring a Woman Shoe Shopping

by Sexybeast8899 on Jul 17, 2018
Fetish

I've often find it very interesting how women can have so much power over men using their sexuality. I think every person has things that turn them on. We all have things that bring us to that point where we are paralyzed by lust. For me, this happened about a month ago. I needed a new pair of dress pants and headed to a department store called Kohl's. I wa...