High Heels Training Stories

211,551 results
Orientation
Length
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Infinite Scroll

Trapped and Trained Ch. 01

by SissyIndy on Sep 25, 2017
Transsexuals & Crossdressers

I responded to an ad on Craigslist from some guy asking for help to move some furniture. He was paying pretty well and, after I practically laughed at him for asking if I could lift the furniture, he agreed to have me over to get it done. We moved everything around for what felt like hours, often moving the same piece of furniture to what seemed like the sam...

Brazilian Beauties

by mshsrfc on Aug 18, 2017
Fetish

CHAPTER ONE Donna Floriella Deoporto Norvona de Sante Cruxes stood on the deck of the SS Pogona as it finished docking in Rio de Janeiro. She scanned the waiting crowd, searching for a first glimpse of her husband to be. The year is 1881 and Floriella is a 'Letter Bride' -, the marriage had been arranged between the two families via agents, photographs and...

Neighbors Pt. 01: The Training Rack

by edgeslaveboi on May 7, 2019
BDSM

Right now: I am in a small basement room, bright with studio lighting. I am naked save for a thick leather hood, stiff latex corset around my middle, thigh-high latex stockings, and leather heels. The hood, corset, and stockings are shiny black, the heels sports-car red, though I cannot see them. Or much of anything. I am in a hands-and-knees posture, m...

Sara Jane Submits Ch. 01

by Subone1 on Dec 2, 2019
Fetish

I have always been sexually submissive, hence my username on this website. I have found, however, that as I get older, I have begun to lean toward the Dominant side. I am 62, financially secure, and still in decent shape for my age. I retired from my 9-5 job last year because I was burnt out and financially could afford to make the transition. My wife, unfor...

Bank Teller Turned Hooker Ch. 02

by SweetTastnNess on Dec 2, 2019
Group Sex

Chapter 2 - A NEW JOB Tuesday was the big day. I was starting my new job. Not that it was a career or anything, but it was better than some of my previous jobs. I had worked at Carl's Jr. (Hardee's in the rest of the U.S.) when I was in high school and the previous summer I had worked in the customer service department at a department store. The only thing...

Imperial Prostitute Tenel Ka Ch. 05

by HandcuffGirl on Sep 12, 2017
Celebrities & Fan Fiction

Authoress's notes: This story overlaps with the last chapter of Imperial Prostitute SX-51472 ZERO. It should be considered a sequel to that story. Please read and enjoy all of my stories! Also, please leave me feedback, public or via email. Chapter 5 of 5 On board Moff Fel's flagship, Bloodfin. . . "Good afternoon, Your Excellency," Tenel Ka said as she...

Trapped and Trained Ch. 05

by SissyIndy on Sep 25, 2017
Transsexuals & Crossdressers

There I was, Saturday morning, back in the driveway of my quote/unquote "Master", as he liked to call himself. I turned off the key to the ignition of my car and prepared to step out. He had sent me an email the previous night telling me to show up in the outfit that I had left in during our last session. I looked down at myself and shivered as I saw the s...

Candi's Conversion Ch. 03

by CandiCumminz on Oct 3, 2018
Transsexuals & Crossdressers

Please read Parts 1 & 2 first. - Candi has had a long night and tomorrow she begins her sissy life properly. First thing? Shopping of course! - I hadn't slept well. I'd gone to bed horny and frustrated, and Lucy's screams of ecstasy in the other room weren't helping. Just as I'd got to sleep, a few hours after I'd crawled into bed, a loud phone notif...

B & D Training

by L Peters on Sep 13, 2017
BDSM

She walked into the room slowly, the terry cloth bathrobe cinched up tight. Her face was over done as requested, too much blush and lipstick, gaudy eye shadow and thick eye liner. The cheap blonde wig made her look like another person all together, and that was the point. I wanted her to feel like a different woman; a stranger in her own skin, able to break...

Sexbot Inspector Training

by Cathbad on Oct 31, 2015
Science Fiction

Congratulations on completing your theoretical foundation courses. Everyone here today passed and gets to advance to the next stage. Today you begin your practical training. In future you will be assigned sexbots to test. But today you will be given a choice of sexbot. Once in the testing chambers you will be on your own, apart from the sexbot of course. R...

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