High Heels Training Stories

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Infinite Scroll

Future Anal Slut

by scarlettesubgirl on Sep 14, 2017
Anal

It was dark in the room and she was alone. The scent of the floral candle lingered in the air as did the heady musk of sex. If she weren't blindfolded, she'd be able to look on the rumpled sheets that further attested to the fucking she had received at the hands of her new Master and Mistress, who had continued their fun long after they'd bound her arms behi...

Supply and Demand

by Joe Average on Sep 13, 2017
Erotic Couplings

Brian sat at his kitchen table, reading the morning paper. A feature article on health and relationships mentioned that oft-sited statistic about most men daydreaming about sex about 2,000 times a day. Brian sniffed. Not him. His experience with women was so limited, he dreamed about merely TALKING to a woman about 2,000 times a day. Brian was twenty-six, an...

Mistress M Ch. 01: Garden of Eden

by Toby_dog on Dec 24, 2019
Transgender & Crossdressers

This is my first full foray into the world of D/s. I hope, through my research, that I have done justice to the subject. I wrote another story posted on the Incest board. Titled "Sarah, My wife". You can read that to see my first attempt at this alternative lifestyle genre. This is the introductory chapter, so there is no great amount of sex. As with any st...

The English Ranch Pt. 01 Ch. 04

by slave_william on Sep 15, 2017
BDSM

(Warning –this and later chapters describe William's participation in Pony play and describes heavy BDSM and pain scenes which may not be enjoyed by all readers. Do Not Read if you cannot handle this type of fantasy and please remember, it is fantasy. If you do not enjoy this story or any of my writings, I'm certain that there are thousands of other stories...

Donna's Ultra-High Heels Bk. 02 Ch. 11

by SHAFERLINE on Sep 15, 2017
Fetish

Author's Note 'Donna's Ultra-High Heels, Book 2' is a continuation of Book 1 and can be read without reading the first book, although it is highly recommend that Book 1 be read first since it would be helpful in understanding the character development of the main players. I tried to make the transition to Book 2 as seamless as possible by briefly summarizi...

A Year Ago Ch. 04

by MadQuill on Sep 25, 2017
Transsexuals & Crossdressers

This is an evolving story of sensual investigation. Please review the first three parts of the first Phase . . . * When I returned home the evening I had visited the Mall the exercise gear I'd ordered was waiting. Once in the house I saw myself in the mirror at the entry. Only a week ago when I looked into a mirror I'd made the leap, not out of narcissism...

The Awakening of a Sissy Pt. 03

by sissyjolie4u on Jan 20, 2020
Transgender & Crossdressers

As i was watching the video of Mistress and I for the 3rd or 4th time, my phone rang. "Hello my sweet Joey, how are you doing? I so enjoyed spending our time together, I'm so proud of you and the progress you are making. Are you still in your pink bra and pantie? That is such a sexy look for you, it makes you look so soft and feminine. Tomorrow we will build...

Mandy's Morning

by DominicDarling on Sep 14, 2017
BDSM

7:27am - Darlington Marketing Services, the boss's office I like to be in the office early, sit at my desk and sip my first coffee of the morning uninterrupted by the usual comings and goings of the office. Today I'm the first in so I fire up the espresso machine and flick on the screens beside my computer to see what today will have in store. I know I'm no...

Training Day

by TubOfLove on Sep 14, 2017
Erotic Couplings

As far as he knew it started with a simple flirt. A comment was made by Megan, our training manager, about stuffy executives as she passed by my office on her way to a meeting. Heading to the same meeting, I exited behind her and joined the conversation with something playful like "I think you'd find me pretty open-minded." She slowed her pace, breaking from...

Mr. White's Cum Sluts

by flashgordon562006 on Sep 13, 2017
Group Sex

This is the final sequel to "My daughter gets her first fucking" & "Turning Diane into a cum slut". ********* Over the course of the next couple of weeks things went well for Diane. She moved most of her personal items to the mansion. She had a large bedroom that she put her own personal touches to make it feel like home. Diane called me every day to say...