High Heels Training Stories

211,551 results
Orientation
Length
Source
Infinite Scroll

Ava’s Surprise Submissiveness Pt. 03

by SHAFERLINE on Sep 19, 2017
BDSM

Prologue Part 1 of this story introduced Scott Walker and Ava Booker who met at lunch in a mall restaurant when Scott took the last seat at the bar next to Ava. He was a manager at a large pharmaceutical company in town and Ava was an assistant to a vice president at a large advertising agency. They both had come to the mall to do some Saturday shopping and...

Slut Job Advertisement

by Decadent5 on Sep 17, 2017
BDSM

New submissive slut Job Posting Open position for two (2) bisexual submissive sluts. 8 Hours a day/ 3 work days a week with one weekend off every month. The remaining 3 weekends will be 24-hour days. sluts applying for the open position will read and be prepared to have body modified to meet needs of job description. While prior experience is helpful, it...

Training Day

by LoneStarDamsel on Sep 16, 2017
Anal

I sat uncomfortably in the waiting room. I shifted my weight from one side to the next. The beautiful room was filled to capacity with gorgeous woman each studying the latest in high-fashion magazines and catalogs. Finally the woman behind the window called my name for my appointment. I was unsteady in my 4-inch heels and my blouse seemed unusually taut acro...

My New Maitresse Ch. 02

by Cagedcompliance14 on Sep 14, 2020
BDSM

My high heels clicked down the hall to the guest room where I saw a small green army surplus hammock in the middle of the room. As I laid down I wondered to myself why had I so meekly accepted Emma's terms? This was insane I am sleeping in a french maid dress and a cock cage. I think deep down I felt terrible for cheating on Emma and felt I deserved some of...

Donna's Ultra-High Heels Bk. 02 Ch. 09-10

by SHAFERLINE on Sep 14, 2017
Fetish

Authors Note: The following is a continuation (Chapters 9 and 10) of Book 2 of "Donna's Ultra High Heels" which followed Book 1 of the same name, all in the fetish category. It is recommended that this series be read in order. ***** Chapter 9 After arriving back at Ken's apartment from the visit to the Chatsworth's Mansion, Donna and Ken hurried to the...

Laura Lake's Trip to the Mid-East Pt. 02

by SHAFERLINE on Sep 15, 2017
BDSM

Prologue Laura Lake and her junior assistant Johnny Jordan were reporters for the Metro Star News published in St. Louis and had been on an undercover assignment in the small Mid-Eastern country of Arabica. As the result of being set up, they had both been captured during a trip to a remote desert by slave traders. Because both Lara and Johnny possessed so...

Nancy's Summer Job Pt. 04

by SHAFERLINE on Sep 17, 2017
BDSM

Prolog Nancy Nichols had just finished her junior year at UNLV and decided to stay in town during the summer and take a couple of courses to relieve her crowded senior year schedule, rather than return to her parents' home in Chicago. She had applied and gotten a part time job at "Monica's Stilettos and Lingerie" which was a shoe store that also sold vintag...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

Not So Fun Games Ch. 03

by StoryTeller07 on Sep 19, 2017
BDSM

Not So Fun Games Ch. 03 Fully trained to obey For once she was pleasured rather than being simply taken, and the satisfaction he gained from her body added to her enjoyment. It was a wonderful night. She awoke early waiting for her Master to stir. Tethered to the end of the bed, she rested her chin on the edge, gazing up at him in admiration. If her husb...

From Stephen to Stephanie Pt. 03

by nikkiwest101 on Sep 12, 2017
Transsexuals & Crossdressers

Chapter one As we drove towards the airport my mind was a mass of emotions, the last ten days had been a complete transformation in my life, one of the things I was struggling to understand was how permanently sexually aroused I was, it seemed that I was enjoying expressing my feminine side, something I still wanted to fight against. I found this really...