High Heel Boots Stories

195,962 results
Orientation
Length
Source
Infinite Scroll

These Boots Were Made for Licking

by Raven_Darkwood on Oct 29, 2018
BDSM

Legs intertwined, tangled in sheets, they laid in the afterglow of their most recent passion. As they often did during their cooldown, they found themselves flipping through pictures of beautiful women online. Scrolling down, at the sound of the "ooooh" escaping the lips of his love, he stopped on the picture of beautiful goth woman. Upon seeing her ivory sk...

Pussy in Boots?

by PnkOcelot on Sep 13, 2017
Toys & Masturbation

I was on my lunch-break when I saw them, the most beautiful shoes in the world. They were red, a shade darker than blood, and they captivated my. They were exquisitely shaped, the heels were tall and elegant, then curving down, with the grace of a wave, to the toe. The detail was gorgeous: at first they looked plain red, but as I walked closer to the window...

The Podiatrist

by anaflowerchild on Aug 18, 2017
Fetish

He was up to his neck in loans, $100,00 to be exact, when he graduated Podiatry school. He had been there for four years and was well schooled in surgery math and chemistry. So he shared an office on 9th Avenue with another young fledgling. Business was slow for a while until his partner, with computer skills put up a wonderful web site, bringing patients in...

Dominated and Humiliated

by Slaveformistress on Aug 31, 2017
Fetish

It all began when he was browsing the magazines in the local newsagents. The one he wanted had sold out and he was searching for an alternative. Suddenly one caught his eye. It was entitled 'Slave' and bore a picture of a man, entirely nude except for a tight thong and a dog collar. Attached to the collar was a leash, tightly held by a tall blonde in latex....

Wife Converts Husband Ch. 02

by bisexual_slut on Sep 25, 2017
Transsexuals & Crossdressers

This story is totally fictional and any resemblance to anyone is purely coincidental. We end up going to a big lingerie shop and buy several pairs of g-strings, booty shorts, bra's, corsets, suspender belts and stockings of all colours and styles, which Shelley thought would best suit me and a pair of breast forms to give me real looking breasts. We then we...

Foot Boy

by DrJR on Sep 17, 2017
BDSM

This is a true account of how I became the foot/shoe/boot slave to a very attractive young lady. The lady in question was the Assistant to the Dean of Students at the university where I taught. I am a 62 year old, retired college professor. I have a PhD in Communications and had taught at the university level until my retirement, a few years ago. For as lo...

A New Pair of Shoes

by CheriSM on Sep 25, 2017
Erotic Couplings

It had been a while since I'd had a date and the sexual need was getting to me. I decided to go strolling and see if I could find someone willing to play along with me. I showered and shaved, paying special attention to my pussy to make sure everything was clean and ready. As I went through my closet, I settled on a black dress that fell to about mid thigh...

Schoolgirls are Real Bitches

by SPARTAN047 on Sep 14, 2017
NonHuman

On request by anonymous feedback from Literotica as a (sort of) thank you. Amazing This story (I've read both of your dark elf stories) is pretty amazing. Best I've read in a while actually, you've gotten yourself another fan! If you do take requests, I'd love to see more about this setting. Specifically, perhaps even the flat girl who enjoyed humiliation...

Torrid Lady Victoria Ch. 05

by 123z on Feb 25, 2019
BDSM

Kent, September 1921. xxx When her Ladyship, Victoria Ponsonby Smythe, looked back on the last five years she had to chuckle. What had been a spur of the moment event, her bare handed spanking of a clumsy maid in her service, had actually been a life changing moment. In a loveless and sexless marriage to sixty year old Lord Henry, the now forty year old we...

My Girlfriend's Little Sister

by JSamuels58 on Oct 12, 2020
Fetish

I had just gotten into a huge fight with my parents so I called my girlfriend to see if I could spend the night at her house. She said of course I could, but she has work until 11 that night, but I can just let myself into her house since her parents love me anyways. It was about 7:30 so I made my way to her house and knocked on the door. I was greeted by h...