High Heels Training Stories

211,551 results
Orientation
Length
Source
Infinite Scroll

Von Estate Stories... Amanda

by greasy963 on Sep 16, 2017
Fetish

I should have posted this story before the conversion of Kathy, but I got wrapped up in it. Hope this bridges the gap from Christina to Kathy and fills in some holes. ***** Christina had just taken her new role in the business structure of the Von Estates. She was working to stream line the import and the movement of finances though their accounts. She had...

Total Woman Pageants 06

by bhuff on Sep 16, 2017
Novels and Novellas

Victor's doorbell rang. He opened to find his latest tutoring subject. She wore a leather neck collar with silver rings peeking beneath her shoulder length red tresses. Her outfit was a tight fitting sleeveless black dress, cut low in the cleavage and high on her thighs. Her strappy black heels held ankle rings with little locks for closures. She carried her...

Donna's Ultra-High Heels Bk. 02 Ch. 06-08

by SHAFERLINE on Sep 15, 2017
Fetish

(Authors Note for Book 2, Chapter's 6 – 8) Donna's Ultra-High Heels Bk. 02; Ch. 06-08 is a continuation of Donna's Ultra-High Heels Bk. 02; Ch. 04-05 (duplicated in that submission) which followed Donna's Ultra-High Heels Bk. 02; Ch. 01-03 as separate submissions. These three separate Bk. 02 submissions all followed Donna's Ultra-High Heels Bk. 01 which wa...

First Time Sissy - The Bike Path

by Phillysissylexi on Jun 15, 2020
Transgender & Crossdressers

My roommates had gone away on a trip for a week, so I had the house to myself for a few days. I had been waiting for a moment like this. As soon as they left I went to my closet to find all my girly clothes, toys, makeup, heels, and lingerie. I couldn't contain myself. I was so excited to turn myself into a sissy. I turned on some sissy hypno to listen to wh...

The Diary of Jewel Delacroix Ch. 12

by BJGoodhead on Dec 24, 2019
Transgender & Crossdressers

The following contains themes of forced feminization, reluctance, non-consent, and other adult topics, so before we begin here are the usual disclaimers. This is porn, you must be over 18 to read this. If not, go away and come back when you are old enough. If you are old enough and this style of erotica isn't to your liking, then go find some erotica that is...

The Project Pt. 04

by Chloecrownofthorns on Jan 20, 2020
Transgender & Crossdressers

"What did Delilah put in that last drink?" Chris thought. "Perhaps I had too many, but what crazy dreams I had! They seemed so vivid and real!" Chris's dick swelled as he recalled the previous night and a wave of pain hit him. He reached down to touch his dick but found nothing to grab. Panicked he ripped the covers off and looked down. "Oh no, no, no!" H...

Trapped and Trained Ch. 02

by SissyIndy on Sep 25, 2017
Transsexuals & Crossdressers

I drifted in and out of consciousness over the next hour, periodically snapped back into reality when the dildo assaulting my mouth would pause deep in my throat and eject a fresh deposit of cum into my bowels. Looking up at the television display of my abuse I would normally have been turned on by the sight of this brunette in a pink corset and black stocki...

Always Read Before You Sign Ch. 03

by Reaver90 on Apr 6, 2020
Transgender & Crossdressers

"Wakey wakey sleepy head," Paula said. Samantha groaned. "What time is it?" "It's seven in the morning," Paula replied. "It's time for your boosters." Samantha got up slowly and yawned. She felt the two pricks on her arm. "All done," Paula said. "I would let you sleep for longer. But I've got to go out." "To the office and do shopping, yeah?" Samantha r...

Nancy's Summer Job Pt. 03

by SHAFERLINE on Sep 17, 2017
BDSM

Chapter 6 After getting home, Nancy, for the fourth evening in a row, changed into her home training outfit that consisted of the padded panties, corset, and shelf bra with a thin white front buttoning blouse, short shorts, wide belt, and of course, her 6 inch heeled training pumps. She had decided to wait till after Jim got there to wrap her nipples since...

Another Submissive Slut Ch. 04

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

She was leading me unerringly to my place. How did She know where I lived, I wondered briefly before the effort of walking with such a large plug in sissy hole forced my attention else where. Panting more from nerves than the walk I quickly opened the door to the building to get us in and off the street. Almost immediately my landlady was upon us. I nearly s...