High Heels Stories

202,281 results
Orientation
Length
Source
Infinite Scroll

Professor Li's Pantyhose Ch. 01

by fanofpantyhose on Sep 26, 2017
Fetish

I first met professor Li in my computer science class. It was not the first class of the semester, as she had a teaching assistant take care of it initially, but she showed up in person for the first time in early October. She was rather small and had a very slender figure. Her hair was quite short, but not too short, and her eyes showed clearly her enthusi...

Aunt Cathy Ch. 1

by HIHEELS on Sep 13, 2017
Fetish

My Aunt Cathy had fascinated me all my like and I had only just turned seventeen. She was single and worked in a ladies department store selling women's clothing and lingerie. Cathy was in her early forties but looked like she was in her thirties. She is petite - 5' 3" and a little over 100 lbs. She had a nice figure and beautiful legs and feet which is wha...

Kitty's AssKissing LegBoy Pt. 02

by KittyZateez on Aug 28, 2018
Fetish

I had just made my LegBoy play with himself and beg me to kiss my ass, but of course I just had to be true to form, so I diverted his attention away from that desire back down to my legs and high heels instead...right where I wanted it! He was once again down on his knees in front of me with his erection sticking out toward me proudly, and I snatched the pa...

Spanking Gloves F/m

by hall2226 on Sep 12, 2017
BDSM

The phone rang three times before it was answered. "Bournemouth 448981." "Hello Mrs. Temple. It's Charles Leyton here. How are you?" Charles realised as he heard himself speak that his voice sounded strained and oddly high pitched. A brief pause ensued, as if the receiver of the call was collecting her thoughts. "Charles dear, how nice to hear from you....

The Teasing Air Hostess Ch. 03

by footslave85 on Sep 26, 2017
Fetish

Chapter three I arrived home and immediately dropped everything, practically ran to by bedroom and was naked in seconds lying on my bed. I had the stocking draped over my face and reached down to massage my already hard cock. I had been stoking for about 5 seconds when my phone beeped. I instantly remembered that I was supposed to wait for instructions and...

My New Life in Lingerie

by Everyday2 on Jul 14, 2020
Transgender & Crossdressers

It started innocently enough. There was that time many years ago when I saw a pair of my wife's panties in the laundry hamper. I couldn't help myself and decided to try them on. They were amazing! The way they hugged my ass and balls is impossible to describe. I left them on most of the day as my wife was gone to work. Walking in the panties made me hard, an...

Created in the Image of a Superior Being Ch. 02

by alyssawinters on Apr 15, 2020
Transgender & Crossdressers

'Created in the image of a superior being.' pt 2 Philip Meyer needed to counter balance the dominance he recently experienced from Gloria. He had been cultivating the twenty-something male bike messenger Brendan for some time. His shock of unkempt red hair reaching his shoulder the thin framed 25 year old male locked up his bike on the street pole before wa...

Pretty Lady in High Heels

by Girl Friend on Sep 24, 2019
Fetish

Ceinwyn had received the wedding invitation over a week ago and she was still undecided as to whether she should attend. Never mind that she had no one else to bring along as her date. But that was no surprise as she was shy and rarely went out. She rifled through her closet and picked out a red dress with ruffles. She imagined it would do if she decided t...

Donna's Ultra-High Heels Bk. 02 Ch. 06-08

by SHAFERLINE on Sep 15, 2017
Fetish

(Authors Note for Book 2, Chapter's 6 – 8) Donna's Ultra-High Heels Bk. 02; Ch. 06-08 is a continuation of Donna's Ultra-High Heels Bk. 02; Ch. 04-05 (duplicated in that submission) which followed Donna's Ultra-High Heels Bk. 02; Ch. 01-03 as separate submissions. These three separate Bk. 02 submissions all followed Donna's Ultra-High Heels Bk. 01 which wa...

Kitty's AssKissing LegBoy Pt. 04

by KittyZateez on Sep 12, 2018
Fetish

My legs were sticking straight up in the air as I laid back on the bed. My LegBoy was standing in front of me, naked except for the pair of sexy, satiny pink sissy panties he had on, which covered up his achingly erect cock. His wrists had been cuffed behind his back to restrain him and prevent him from pleasuring himself, and the pantyhose leash was still a...