High Heels Training Stories

211,551 results
Orientation
Length
Source
Infinite Scroll

jenny Trains Her 'Slut-sis'

by slutty_jannelle on Sep 14, 2017
Transsexuals & Crossdressers

Although each story will stand on its own, the reader will enjoy the series more in sequence: "jenny's Education," followed by "jenny Gets a 'Sister." It seemed like she'd just gone to sleep when jenny shook Kay awake. "Time to get up, girl, We've got a big day ahead. Lots to do," jenny said, unceremoniously pulling the blanket off. Instinctively, Kay...

A Kennel Opens

by TheBitchWhisperer on Sep 14, 2017
Fetish

This economy is killing me. Or as the general parlance goes, "it fucking sucks." "I'm sorry, Kay, but we really just cannot afford to continue your contract." He looks genuinely pained, but I am looking for any falsity, pretense. "I'd be willing to cut my rates, as I have the last three years, but the margin is getting smaller," I offer. He smiles. "I app...

Being Holly

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

Okay like right off I want to make it clear it's Holly now and forever. Holt's fucking dead and I'm killing anything that's left. And that's a damned good thing. See Holt was an asshole, I...he...that person I was...I was raised by an asshole. My dad and he wasn't a nice guy. He was a jock, he was a mean jock raised by worse my grand dad. Holt was part...

Total Woman Academy 15a

by bhuff on Sep 14, 2017
Novels and Novellas

Karl heard a knock; it was his 2 o'clock appointment. "You may enter" he called. His next coaching tune-up appointment, topless, toned and pensive, glided meekly through the door. The buxom blonde student stood silently, head faintly bowed, shyly observing Karl's face for an indication of how to proceed. Karl let her wait while he surveyed her near nakednes...

Ava’s Surprise Submissiveness Pt. 01

by SHAFERLINE on Sep 19, 2017
BDSM

Ava's Surprise Submissiveness Pt. 1 Ch. 1-4 Chapter 1 Scott Walker was a manager for one of the large pharmaceutical companies in the metro area. He was twenty six years old and had split with his girlfriend about three months ago. He had been going with her for a little over a year when he decided that she was much too demanding in their relationship than...

Auctioned Teacher Ch. 01

by StoryTeller07 on Dec 28, 2017
BDSM

Suzanne is kidnapped and trained Suzanne carefully made the meeting arrangements, so as not to put herself in danger. Meeting a stranger was risky, though she needed to do it. Sharing intimacies of her life with a man on the internet, over the past few months, had been enjoyable, and a good release of tension. Having someone to share things with, a secret...

Making Francesca Ch. 05

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

It seems that I finally have gotten the time to finish posting this story. If you have not read the first four chapters, I highly recommend it as the story will make much more sense. Enjoy. As he sat there on the thin mattress, pondering his new outlook on life, Justin appeared with his supper. Justin opened the door to the cell and placed a folding chai...

Miss Guided

by MissMarianne on Mar 12, 2019
Transgender & Crossdressers

My name is Susan and my husband Charles, we are both 25 years old and have been married for one year. Recently Charles has been very depressed and He lost his job when the company moved to Malaysia. Lately his performance in bed has been sub-par and , in fact, he can't get it up most of the time. We feared he was becoming impotent but the doctor said the pro...

Kitty's AssKissing LegBoy Pt. 01

by KittyZateez on Aug 28, 2018
Fetish

My LegBoy has been tending to my sexy legs and high heels for several weeks now during repeated teasing and denial sessions. During that time, we have had many delicious and stimulating evenings together, and I am absolutely adoring the way he has been responding to my specialized erotic training! He is just so interested in me, so willing to obey my whims...

Total Woman Pageants 01

by bhuff on Sep 16, 2017
Novels and Novellas

Victor's doorbell rang. He opened to a short bronzed beauty, well rounded in all the right places. She wore a short skirt, sleeveless white blouse and stylish high heels. She handed Victor an envelope and said "This is my letter of introduction." Victor opened the letter and read: To: Victor, Senior Pageant Trainer From: Ms. Smith, Chairwoman, Total Woman...