Rubber Boots Stories

55,431 results
Orientation
Length
Source
Infinite Scroll

Julie's First CD Night on the Town

by juliegomez on Sep 14, 2017
Transsexuals & Crossdressers

There was a parking lot that was out of the way where I changed into my set of girl clothes for my night of adventure. The nylon underwear was tight and sleek, I had a raging hard on as I drove into town. I had been planning this night out for quite a long time and was hoping to get my butt well and truly fucked before the evening was over. In town there wa...

A Painful Test

by ChristopherDB on Sep 19, 2017
BDSM

Previous stories in this series: Off-Road Goddess, Paddled in the Boondocks, Lunch With A Dominatrix * It was late on a Saturday afternoon that I drove to the east side of the city, following directions that had been given to me by Miss Julia. Near the industrial park where she worked, I turned onto a state highway and continued east just until signs of ci...

Stage 01

by Capt. Stable on Sep 17, 2017
BDSM

Stage One: The Doctor's Orders She knew she had done wrong, but most importantly she knew she'd be in trouble. Those boots had clearly been left out for cleaning, but she was so enthralled with her new present, a pair of beautifully high ballet boots, she just had to 'wear them in'. And so she sat upon the corner of the bed, decadent in her sleek shiny ball...

Meeting The Master

by clcarne on Sep 13, 2017
BDSM

I met the Master when I first came to work for his company. He seemed stern and cool, but was very fair to me. I had started college at seventeen and finished early. By the time I was twenty-six, I was hired to be his personal council. My childhood was a nightmare and I think he became a father figure to me. Then he took me to Asia, and introduced me to the...

Crystal's Show

by With_Lust on Sep 15, 2017
BDSM

This is a fantasy for those over 18. It is not true, the characters don't exist. * Her sub was tied diagonally to the king sized bed. Hands stretched above his head. Feet tied to the opposite corner so she could have his six foot, frame displayed for her pleasure. Mistress Crystal had made his blue eyes irrelevant with black silk wrapped tightly around hi...

Play Time

by ViperVenom on Sep 14, 2017
BDSM

"I've got special plans for this weekend," Biri purred. It didn't take too much imagination for Leif to determine what those plans would be. His girlfriend's outfit made some very clear statements in that regard. "Can you even breathe in this, sweetie?" "As long as I don't laugh," she chuckled and let her latex-gloved hands slide along the skimpy rubber d...

Bi-Fun: DP

by latexcd69 on Aug 29, 2017
Fetish

My first three-way was absolutely amazing. I would have never thought it would be with my girlfriend and cousin, but I suppose that makes it even more interesting. Everything seemed to run so smoothly when we did it that we all wanted to do it again. Whenever we'd talk about, it never seemed awkward. A few weeks had passed with several failed attempts at r...

Identity Ch. 01

by rachelg on Sep 17, 2017
BDSM

(C) 2006 Rachel Gumm. You may freely distribute this story digitally, but only in full, crediting me as the author. I welcome feedback. You can e-mail me at the address in my profile. I haven't written part two yet, but if I get enough e-mails showing a desire for it, I'll write it soon. * Kevin felt himself get an erection as he looked at his now safely...

The Meeting Pt. 04

by Sprock123 on Jan 7, 2018
Transsexuals & Crossdressers

From part three... I was flabbergasted, as he reached for me and pulled me into his arms and kissed me again, gently then passionately. We spent a long time just stroking and caressing each other through the rubber of our macs. He spent what seemed like ages just stroking my body through the basque and then my legs through the leather of the boots. I spent...

Michelle's Hotel Bondage Experience

by michellelakes69 on Sep 13, 2017
Transsexuals & Crossdressers

As a timid and closet cross-dresser, my biggest fantasy was to have a sordid meet in a hotel room, where I left what happened up to another person, with only major limits discussed and agreed first. After months of search and waiting for the right person to come along, I finally met 'Sylvia' online, and I had finally decided to take the plunge to meet up wit...