High Heels Training Stories

211,551 results
Orientation
Length
Source
Infinite Scroll

From Stephen to Stephanie Pt. 05

by nikkiwest101 on Sep 12, 2017
Transsexuals & Crossdressers

Chapter one The preparations for my wedding proceeded apace, I was never allowed to see my wedding dress and was kept hooded during all of the fittings for it, these fittings were numerous and each time the skirt was made tighter, I wondered how on earth I would be able to walk in it. My training in every area increased, my voice coach visiting daily, my co...

Sonya Loses Her Virginity

by huge_penis on Sep 12, 2017
First Time

If you are interested in editing my stories, please contact me. I RECOMMEND THAT YOU READ VASELINE CH. 1 AS WELL. ALL CHRACTERS ARE 18 YEARS OF AGE OR OLDER. PLEASE ENJOY! Hi! My name is Sonya Singh and I am a 19 year old, single, completely whitewashed Indian girl. I live with my parents and my sister who is a year younger than me. My dad is an entre...

The Hottest Fire Ch. 10

by velvet hammer on Sep 14, 2017
Novels and Novellas

Chapter 10. Barbara’s Advanced Training That afternoon Ludlow took Barbara to London in the Jag, to a certain Victorian row house in Kensington. There he introduced her to the Iron Lady. The Iron Lady looked very elegant in a simple blue dress with a double strand of pearls around her neck; a golden silk scarf about her shoulders was held in place by a came...

Sara Jane Submits Ch. 02

by Subone1 on Dec 2, 2019
Fetish

I woke up to use the restroom, it was 5:30 AM and still dark outside. As I swung my legs out of bed I almost stepped on Sara Jane! She was asleep on the floor next to my bed, curled up like a little puppy. She had her hair up in a towel on top of her head from the shower, not a stitch of clothing on her wonderful young body. "Jesus Sara, what are you doing?...

Renee's Auction as a Pain Slut

by soppingwetpanties on Dec 26, 2017
BDSM

Warning: This story contains graphic scenes depicting nonconsensual sex and pain, including caning. This installment completes the trilogy of stories. If you want additional background on Renee, please read Renee's Seduction and Submission (Book One) followed by Renee's Seduction and Submission. Dedicated to sue -- you wanted to make sure I got it right. h...

Always Read Before You Sign Ch. 02

by Reaver90 on Apr 6, 2020
Transgender & Crossdressers

Sam stood outside Miss Turner's front door. The weekend was hell was for him. He couldn't sleep, he had to sit down on the toilet and pee like a girl and more importantly, he couldn't jack off. The young man feared what the beautiful woman but deadly woman had in store for him. He took a heavy breath and knocked on the door. He waited for a few seconds as t...

The Training Ch. 01

by Speakeasy on Sep 12, 2017
BDSM

I saw this ad on a D/s website, repeated here without editing: "married for six months , originally from Ukraine, 24 years of age, nice looking and my husband is from UK. He likes to get me trained to be his submissive. Never tried it for real except back homewhen I was getting my spankings. Need me to be his slut, asks me to dress very daring, and he even...

Linda and the Lash Ch. 04

by adoration on Sep 14, 2017
BDSM

Towards the end of breakfast the following morning - Carmen and I sat naked, the men in thongs - Brad looked at Gary with what I thought was a malicious grin. "What say we give Linda a double F?" he asked. The term "double F" meant nothing to me, but Gary was obviously fully aware of what his host was talking about. "What a wonderful idea," he said, pouring...

Anari's Predicament Ch. 01

by ScarlettSlave on Sep 17, 2017
BDSM

Anari found the building, on her first visit, cold and uninviting. Truth be told, if there were a possibility of running away from her desperate situation she would have done. She had found herself getting deeper and deeper in a clinging quicksand of debts, from which there was little escape. She shuddered as she remembered the expression on her bank manager...

Layin’ Leylin Ch. 03

by Irish Moss on Aug 28, 2017
Erotic Couplings

Disclaimer: This is a story in which a fictional character cheats on his wife. If you find this sort of thing offensive, I recommend not reading any further. You have been warned, so please don't send me feedback or post comments telling me how wrong it is for men to cheat. This is fiction. Although Leylin is based on a real person, to the author's knowledge...