Stiletto Boots Stories

41,602 results
Orientation
Length
Source
Infinite Scroll

Two Trannies and the Beast

by roberty on Dec 31, 2017
Transsexuals & Crossdressers

So at last I'd found a lover, named Roy. Roy loved to watch, and I loved it when he watched, so it was a great match. Last night Roy lay like a conqueror on his bed, the one with a floor to ceiling mirror behind it, and watched as I performed in nothing more than a garter belt and stiletto heels, both cherry red, which he had bought for me on an internet s...

House of Syn Ch. 01

by MSTarot on Aug 31, 2017
Fetish

(I ask that any who even think of following this type of fetish go get a blood pathogens test done for both partners. The risk to your health is incredibly great. With that note of warning enjoy the story) Chapter 01: Father of Syn Pulling the car to a halt in the parking lot of my club I shut off the old beast and open the door. It protests being opened...

She Didn't Have To Lie

by DeniseNoe on Sep 2, 2017
Fetish

Taylor saw a trick. A green Honda Civic was slowing down and, yes, the guy was nodding at her. She walked to the driver's window as fast as she could, though slower than usual because of the irritation on the ball of her left foot. "Can you tell me which way to Kroger's?" he asked. Damn. She knew and gave the fucker directions. A pretty, slightly built Af...

Amazing Matinee

by ten_amazing_touch on Sep 15, 2017
Fetish

The service manager at the dealership gave Gary the bad news. It would be 4 or 5 hours before his car was ready. He decided to kill the time at the mall instead of hanging around the dealership. It was close by and the day was pleasant, so Gary didn't mind the walk. He could think of a better way to spend a rare Monday away from the office, but it was still...

Jennifer Gets Dirty

by sexy_jessie on Sep 17, 2017
Celebrities & Fan Fiction

This story is a follow up to my earlier celebrity story "Comforting Jennifer" in which (fictional) tennis star Jennifer Stanton is comforted in a very special way by Anna Kournikova. You don't need to read that story to get this one but please do anyway because I like my stories to be read. Jennifer Stanton's career and popularity had gone from strength to...

Mark & Maggie

by Secret Places on Sep 17, 2017
Loving Wives

It wasn't that there marriage was loveless, they more than definitely had love for each other, it was more that they had fallen into a state of routine which became increasingly difficult to fall out of. Maggie was 24 and seemingly in her prime of life, her long slender legs were what drew Mark's attention every time she walked by in her short "business" s...

Charity Slave Auction Ch. 08

by Kay_Evans100 on Feb 3, 2020
Fetish

Charity Slave Auction Chapter 8 Kay is at a large English Country house for a black-tie charity event which has a theme of fantasy fashion and has also been persuaded by her friend John to model some of the fashions in the fund-raising slave auction. She has taken part in four rounds so far and is now in the final five; the final winner receives a prize of...

Derek & Amy: Boys Night in

by Kalira on Sep 16, 2017
Transsexuals & Crossdressers

Tonight is the night Matt learns how to be a true lover. Before, he had his wife Amy to hold his hand when they played with Mistress Derek but tonight, he's all on his own. Before Mistress Derek arrives, Amy prepares Matt using the instructions she received from him. Matt is to be dressed in a sheer, pink babydoll top with fluffy breasts and matching panties...

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...

Breaks the Day Up Nicely

by NeilMc123 on Nov 4, 2019
Exhibitionist & Voyeur

I'd been out most of the morning, getting my pampering completed, Nails, Hair, Bikini and Body Waxing, and spent an outrageous amount of Jeff's money on some very salacious sexy underwear. Jeff does like the soft latex and faux leather look and he'll be pleased to know my latest purchases will not disappoint him. In my shopping bags were a very provocative q...