Trampling Heels Stories

81,118 results
Orientation
Length
Source
Infinite Scroll

The First Christmas

by Torianne on Sep 17, 2017
BDSM

Author's note: This story is a culmination of mine and my sister Sara's minds as we worked for our first Christmas with our Master. "Are you almost finished down there? The top half still needs your attention." He slapped the crop across her bare ass at medium strength, a simple emphasis to finish her task and move on to the next. She hung the last orname...

Road Trip

by NorthCoaster on Sep 13, 2017
Group Sex

As he exploded in her mouth she felt the car slow a bit, bearing to the right. She wiped the last remnants of his pleasure from her chin and sat up, taking a look at the rest area around them. They both needed to compose themselves so he picked a remote parking space in the RV lot and put the car in park. To their mutual chagrin, a small Winnebago pulled int...

Anna Saves the Company Ch. 01

by dan09 on Sep 13, 2017
Loving Wives

Anna thought she had the perfect life, at 27 years of age she was young, beautiful and intelligent. Married to her husband of 2 yrs, they both had good jobs and made each other very happy. They weren't rich by any means but they both had good salaries and were particularly careful with their money. This however was about to be put in jeopardy, as the world b...

Fun with Dick and Jane Ch. 04

by DesperateHousewhores on Sep 19, 2017
Group Sex

Chapter 4 The Meet n' Greet Jane looked at Dick and nervously, smiled, and said, "OK then, let's go!" Dick smiled at Jane. "Are you sure?" "I'm nervous, but let's go see what it's like," Jane said. "Besides, what's the worst that can happen? It's in a bar so it's not as though anyone is going to jump us," Jane added. Dick agreed and they both began to...

In The Beginning...

by NYCSeparatedWM50 on Sep 13, 2017
Romance

I remember how it started. First there were enormous boxes that were glorified typewriters, handling "word processing." Along came spreadsheets, and then games on CD-ROMs, like primitive DVDs. Dial-up modems that hissed and chirped in the night. Each little advance led to another, like a natural evolution, and then one day we found ourselves in chat rooms,...

n Island Escape Ch. 03

by lustprincess on Sep 17, 2017
BDSM

Bree woke up with a cramp in her back and tried to stretch out. Then, she realized that she couldn't move any of her limbs. Frantically, she tried to sit up to see what was restraining her- rope tied to the head and footboards of the bed. Max had tied Bree spread eagled and was nowhere to be seen. All she could do was lie there, helpless and exposed to the w...

Tami Monroe And Racquel Darrian

by 123z on Sep 17, 2017
Celebrities & Fan Fiction

Note- Another entry in my legendary pornstar dream team. ***** Tami Monroe stretched out her arms and gave a yawn. Her eight hour shift at the Tisch Hospital on First Avenue had gone by without any bother and she waited patiently for her relief. The last time she had checked on her two patients half an hour before they were both sound asleep. The former p...

Collared and Owned

by HoldsTheLeash on Sep 17, 2017
BDSM

Her phone buzzed in her lap as she received a new text message. Her heart jumped into her throat, hoping it was her Master. But she was driving home from a short day at work and was always nervous to text and drive. But if it was Master, she had better reply, or she would get punished. And not in the way that pleased her. He would humiliate her, use her in u...

Terry's Descent Ch. 05

by jack.joyce on Sep 15, 2017
Transsexuals & Crossdressers

Early Hours I woke, cold and aching, on the guest room floor. The sounds of sex were still coming from the master bedroom. I could not help but sob as I felt the uncomfortable dampness of cum in my underwear, and the taste of my own ass in my mouth. I picked myself off the floor and cleaned up somewhat, my tiny dick twitching as I looked at my slutty demea...

A Dream Comes True

by dalespeer on Sep 12, 2017
Transsexuals & Crossdressers

AUTHOR'S NOTE - This story is my first fictional foray into the world of Crossdressers, Shemales and Transsexuals. All comments will be appreciated of those who submit them. * I was sitting in my home... if you could call it that. It was an apartment in a complex that looked so run-down it wasn't funny... and it drove away most of those who wanted to rent...