Stiletto Boots Stories

41,602 results
Orientation
Length
Source
Infinite Scroll

Project: Broadsword 00

by BootsToBed on Sep 16, 2017
BDSM

DISCLAIMER: At no point is this story meant to reflect real life events or encourage anybody to try and make it into real life events. If you are easily offended by descriptions of an adult nature then you're obviously on the wrong website. So if you like it, please leave a comment. If you don't like it, nobody is forcing you to read it. Prologue In the co...

Stiletto Spree

by BrettJ on Sep 14, 2017
Mature

If you read through this one, you might spot some old friends. But don't blink, or you'll miss them! Enjoy readers!~~BrettJ * Mattie Addison looked down at the small plastic object her mom had just placed in her hands. "What is this?" She asked as she looked up at her parent. "What does it look like?" Cybil replied to her daughter. "It looks like your Pl...

Mistress Jodie

by pete1229 on Sep 15, 2017
BDSM

I am not sure why I tried this, but I was feeling like I needed to take a risk and see what could come of it. I guess I should begin by saying, by nature I am a very submissive man when it comes to the bdsm lifestyle. So when I decided to wear a collar I had fashioned out of a leather strap, metal o-rings and a few other assorted items, out to my local super...

The Transformation of Ms. K

by parkerkwon on Feb 25, 2019
Transgender & Crossdressers

By day I'm an average Korean guy, a bit on the fat side, my whole life I haven't been very attractive to women. I'm very timid and shy as a boy, very much a beta. I never even had sex until after college and my dating life has always been pathetic. I've always had a bit of a tight rubber and latex fetish, as I became older I began buying some pieces of lat...

An Ever Changing Story

by Helenthemaid on Sep 16, 2017
Transsexuals & Crossdressers

Caught Out and Permanently Punished I was wearing a ultra short black leather mini skirt, a tight leopard print low cut top, which revealed my cleavage entrapped by my pink lacy bra (with matching panties). The straps of my 6 inch leopard stiletto heels were securely padlocked around my ankles. Recently I had been often going to the local park dressed in...

Star Wars: Imperial Hospital Visit

by HandcuffGirl on Dec 24, 2019
Celebrities & Fan Fiction

Authoress's notes: The following story takes place soon after the Fate of the Jedi series. Please read and enjoy all my stories, and feel free to leave me feedback, public or private. Imperial Hospital Visit "Hello, Mrs. Fel-Solo," the perky young receptionist greeted her as Jaina stepped off the turbolift. "Colonel Fel is still in room seven-oh-four," sh...

The Man Who Fucked His Way Across... Ch. 02

by Hugopossetposset on Sep 2, 2017
Fetish

The Man Who Fucked His Way across Chelsea and Back Again - Part 2 INTERVIEW I was invited to see the head designer, Liza Blow at Vagina Shoes after a successful phone call. I forwarded some of my friend's best sketches by email and she phoned me back a few weeks later. Jefferson, who let me borrow one of his portfolios, was a Cordwainer's graduate and spec...

Pinky - Bowing Out

by mshsrfc on Sep 16, 2017
Fetish

Pinky checked everything was laid out on the dining table in the correct order, getting dressed was going to be hard enough without struggling to find any parts of the outfit. Her boyfriend Jerry, correction, her Master (she would really have to get used to thinking of him as such) was relaxing in an armchair with a little smile on face. The reason he was s...

Pussy In Boots

by Natalya on Sep 11, 2017
Fetish

Around a month ago I came home from work, tired and just ready to slump down in front of the TV all night. I knew that my husband wasn't home yet, we both worked Saturday's, so I headed straight upstairs to the bedroom, ready to relax in a warm bath. I headed into the en-suite bathroom and started the water running. I quickly slipped off my work clothes and...

The Spanking Couples CFNM Party

by reddbunnz on Sep 17, 2017
BDSM

Chapter One: Two days after one of the monthly Spanking Parties, Debbie and Marion were sitting in Marion's home office discussing their sexual appetites. Both were dressed as normal when relaxing in one of their respective houses. Both had casual clothes – for them, at least. Both sported normal, everyday bras and tops, but were butt naked below the waist...