Stiletto Boots Stories

41,602 results
Orientation
Length
Source
Infinite Scroll

Cassandra Ch. 02

by AngelCherysse on Oct 13, 2020
Transgender & Crossdressers

The days and weeks seemed to fly by. My new position at Barnes and Bidwell was a dream come true. It provided me with a cute income to cover my personal expenses (Melissa took care of most everything), exactly fit my bubbly, flirtatious personality, and offered me unlimited opportunity to meet - and have - men! Melissa did everything in her power to reinfo...

Uncontrollable

by Kroschsteven on Sep 14, 2017
Erotic Couplings

I drove over slowly. It wasn't my normal pace, not even an inch of the six foot frame was exactly sure why I was going, or if I really even wanted to go. I had made the drive many times, but that was five years ago. After she ended it, I was hurt. Whoever said that love hurts was so wise, and must have been here too....my respect for her at the time made m...

Daddy's Day of 'Fourplay' Ch. 01

by PixieTink on Sep 24, 2019
Group Sex

I was face-down on the king size bed, my legs and arms splayed obscenely in a manner devoid of all modesty. Muscles screaming and bruises blooming like medals etched on skin, my rag-doll body remained motionless in the precise position it had finally been left after the most incredible and somehow still unbelievable day Iā€™d ever experienced. My mind drifte...

Biker Party

by ukswinger on Sep 13, 2017
Group Sex

Everyone had been waiting for this party, it was looking like a hot summer and we always had a good time when the mood was right. My fella Tom had his new Harley working just right for the run to the coast, the tent was all packed and we were ready. We set off to meet the others at the local pub everyone turned up including a few new faces. The atmosphere wa...

Tables Turned Ch. 08

by mw0212 on Aug 31, 2017
Fetish

Chapter 8 ā€“ 'Let the Games Begin' Jack sat at his desk, phone in hand, his eyes transfixed to his PC monitor. A small window on his screen displayed the image that was laying less than ten feet away from him. His lips curling up to a wry grin, he started to type. Helena Sharp cautiously pulled on her leather glove. She was nervous because she had never con...

Birthday Toys Ch. 01

by Ally_boy on Sep 17, 2017
BDSM

He heard the door open and shivered in anticipation. Who was entering the large, wooden floored room? His Mistress, the woman he had married three years earlier as a naive eighteen year old, six years her junior. Perhaps her older sister, 'Big Sister', thirty years old and with a vicious temper, only matched by her imaginative depravity, or could it be 'Moth...

Abduction

by Theguywhowrites on Sep 16, 2017
BDSM

I was took out from the van by two women. They both wore latex nurse outfits, thigh high boots and black latex gloves. They dragged me inside the mansion and as we walked along the hallway. I saw various paintings on the wall and a few men giving blowjobs to women who wore strap-ons. We stopped at a wooden door. The redhead opened the door and they dragged m...

She Looks Like Sex in Boots

by Itsalljustforfun on Sep 13, 2017
Erotic Couplings

"Morning David, how are you?" "Fine thanks, and you?" "Really good, beautiful morning." This brief exchange takes place as we approach each other across her gravel drive. I'd initially been Debbie's twice a week handyman and gardener for two years at her large 18th century country house before she'd moved into this rented house a year ago. Since then I'...

Laurie's Lesson

by Vertex on Sep 16, 2017
Transsexuals & Crossdressers

Laurie had a secret! Underneath her shiny pantyhose and soft panties was a cock. She was not a girl, but this was not Laurie's secret either. It was something entirely different! She liked to dress like a slut in shiny fetish clothes and boots. She wore way too much makeup and always went for the shiniest, brightest and sluttiest shade of lip gloss. Yes she...

Presentation

by WillSeeking on Sep 13, 2017
Erotic Couplings

Maybe it is my conscious maybe I am not confident enough in believing I can have the attention, yearning and love of such a beautiful soul. Dreamt that you and I were working together. With you being the boss our budding relationship was a close secret. A few big wigs from corporate had come down for whatever reason. From a distance I had watched you greet t...