Stiletto Boots Stories

41,602 results
Orientation
Length
Source
Infinite Scroll

The Care Girls Ch. 06

by Tomsparty on Sep 15, 2017
Transsexuals & Crossdressers

Chapter 6 - Alone in the house. Later that day you pop round to Becky's. It felt great telling your mother that you where going to see the best looking girl at school. She was so proud of you - little did she know. Becky was not along in her house but her parents don't mind as she leads you upstairs to her bedroom. You're amazed at all her beautiful clothe...

Turneffe College Ch. 02

by pollyannaowt on Mar 3, 2020
BDSM

Turneffe College - Chapter 02 - by Polly+Anna (2568 words) Bondage 101 (1/28/20) Last semester Beth had taken Ms. Billingsley's 'Dress for Success' class, and she really enjoyed it. Andrew, her boyfriend, was impressed by the change in her appearance. She was used to wearing four and five-inch pumps and strap heels, and she had a pair of three-inch demi-boo...

All Tied Up

by redpan on Sep 17, 2017
BDSM

Sally walked into the room. I was watching TV and didn’t really take much notice until that is she stood in front of me. She had her long blond hair tied back in a pony tale, pulled tight from her fore head. She was wearing her red and brown Basque and leather micro skirt. I could see the tops of her fishnet stockings peak from under the hem of the skirt. On...

Seeing Jane

by djm298 on Oct 8, 2019
Erotic Couplings

Jane and I had been working together for about six months. She was transferred from the Chicago office for a project that was dragging on interminably. She is very effective in her work, approaching everything she does with great initiative and a professional attitude. Her credentials are exceptional - top undergraduate and graduate education, top tier firms...

Jackie's Shoes Ch. 01

by addscribbler on Aug 18, 2017
Fetish

The day had started and proceeded as any day usually did. I had taken a run first thing, put on my suit and worked for the day, and before I was going to head home to watch some sci-fi reruns, I thought I would hit up the mall for some window shopping and a smoothie. I ended up finding a quiet spot on a bench in front of a woman's shoe store. After I sat do...

Shades of Black

by lululuvsblack on Sep 16, 2017
Transsexuals & Crossdressers

My name is Luke, but you can call me Lulu, and my favorite color is black. Most people don't have a favorite color, not really, but I'm not most people, so believe me when I say I have a very strong attachment to black. Just let me take you through a typical day and you'll see what I mean. I wake up early, while the night sky is still black outside and get...

The Weekend Slave Ch. 01

by cybergirlsex on Sep 13, 2017
Fetish

This is my first story...Let me know if you want me to continue it! * "Oh, come on guys, don't make me take it off." The fair haired young man shivered slightly, dramatically. "It's cooold. I'm really not attractive when I'm cold. Ya know what I mean?" He smirked slightly. Well, that was what they got when they played strip poker as Fall ended and Winter b...

Watching Susy Ch. 03

by 123z on Dec 3, 2019
Exhibitionist & Voyeur

"Well? How do I look?" My wife Susy entered our bedroom flaunting her astonishing figure in the racy all black outfit I had purchased from Ann Summers online. My jaw dropped as I took in her seriously erotic biker look. The brunette babe had a black leather jacket with one long sleeve, one short and stand up puff shoulders. It closed across her bosom fro...

Interview with a Pussycat Doll

by JonB1969 on Sep 19, 2017
Celebrities & Fan Fiction

My editor came into my cubicle, all six foot plus of him, and said, "Dude, I can always count on you to be playing something from The Pussycat Dolls." I cracked a grin. "Always." "What is it about them, anyway?" "Dude, like you have to ask?" I started to launch into a detailed explanation. But he made a stop gesture. "Dude, forget it, I'm just razzing wi...

The Man Who Fucked His Way Across... Ch. 01

by Hugopossetposset on Sep 2, 2017
Fetish

The Man Who Fucked His Way across Chelsea and Back Again Ch. 01 One day I became Hugo Posset. How, I can't tell you, but that doesn't matter. I became Hugo Posset, a well respected London art gallery owner, good looking, a mere 22 years of age with a big cock. Before I was Hugo, I was an East End barrow boy, with a penchant for posh girls and an insatiable...