High Heels Training Stories

211,551 results
Orientation
Length
Source
Infinite Scroll

It Was HIS Idea

by Leggy_Teaser on Sep 17, 2017
Loving Wives

This is my first attempt so go easy LOL. * It all started some years back I suppose. I am in my late thirties, size ten, sometimes twelve, with a decent pair of legs if I may say so myself and ee size boobs. My husband also says I have a great arse so I'm happy to believe that LOL. I can't really remember how my husband broached the subject that he wanted...

Seven Days: Day 02

by HappyGerman on Sep 16, 2017
Sci-Fi & Fantasy

8:00 AM Shannon awoke, still groggy from the previous night. The men of the village had carried her to a tent and laid her on a bedroll for the night. It was reasonably comfortable, more so at least than the hard ground, and she slept peacefully. Before she could close her eyes to go back to sleep, the Chief walked into her tent. She gaped at him, as he was...

HermmmmmAfrodite Ch. 03

by MrDeviant on Sep 17, 2017
BDSM

Ch. 03: Mistress Diana She was at least 5' 10" tall with the most radiant long hair I've even seen going all the way to her knees and dressed to kill in an all leather outfit that matched her ebony skin tone so well she appeared nude even close up. That description fit all of my five Mistresses, but Mistress Diana, originally known to me only as my 5th Mist...

The Witch Ch. 06

by LunaticLorraine on Sep 26, 2017
BDSM

Authors note - Thanks to everyone who read the previous chapters. I have tried to make this one longer for you. Hope you enjoy :) Chapter Six – Training My training started the next morning. I was very nervous, but excited at the same time. We woke up and had a wash and Alicia got dressed. She then sat me down in the sitting room to explain the rules to...

Office Workload Ch. 04

by Dstorm93 on Jul 6, 2020
Erotic Couplings

Characters in this chapter: The Author (me): A 27 year old single male who just got a new job after few months finding for one Miss Jenna: The General manager of human resources in the company. Mrs Patel: The supervisor who is assigned to guide the author on the daily routine of a HR personnel Cleaner: A cleaner lady who cleans the office during break ti...

Roommate's Toys and Lingerie

by Roxyfox_y on May 12, 2020
Toys & Masturbation

Finally finding myself alone in my apartment for the afternoon I was ready to have some fun. My roommate has been home for most of the lockdown and I've been confined to my own room for my solo experiences. She told me this morning she was headed off to a friend's house for the afternoon. I knew it was time to expand my little world. I know it probably is...

Recruiting of a Sissy Maid Ch. 15

by Sissy_Chantel on Dec 22, 2017
Transsexuals & Crossdressers

Chapter Fifteen: Life Changes but Normalizes Monday morning, Carl and Chantel are up and at it, breakfast in the hotel restaurant and then a shopping excursion to an are Jewelry store for Carl to buy Chantel her engagement ring. Dressed sharply but casually Carl in a white button down shirt, Khakis and black walking shoes. Chantel a white turtle neck, black...

Unconditional Love and Support

by BrettJ on Sep 16, 2017
Novels and Novellas

Hello to all of you out there reading this. My name is Elyse James and this particular tale will begin several stories about my husband Roger and our life together. To begin, it is essential to our shared history that you all know I fell in love at first sight with my husband. We were introduced at a school Christmas party and when I looked into his dark br...

Training Day at the Ladies Club

by lesliejones on Sep 17, 2017
BDSM

[Reading my story, "Toilet Training Elizabeth", will provide some useful background for this story. Those who do not wish to read about bodily functions should read no further. All the characters are over 18 years of age.] After her presentation to the Ladies Club on How to Toilet Train Your 25-Year-Old, during which Kendall humiliated her 25-year-old ba...

Cathy and Chris Ch. 02

by Crazeems on Sep 18, 2017
Romance

The barbecue sizzled and made the kind of smells that only his father-in-law was able to produce from the thing. Jeff was one of the few men he knew, himself included, that was actually able to cook food on the things without the usual drama, and with the added benefit of the food actually tasting excellent. His children frolicked in the garden with his in-...