Sissy Boots Literotica Stories

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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...

Maid on Boxing Day

by Belongs2Beth on Sep 14, 2017
BDSM

Authors note: This story is an immediate sequel to my first story "Carol's Christmas". The events of this story deal with the younger man named Marcus who Mrs. Carson initiated into the mysteries of sex and submission in "Carol's Christmas". * Marcus was sweating bullets as he rang the door. He burned for Mrs. Carson...Mistress Carol...and needed to be wi...

Torturous Boots Ch. 03

by Fetish114 on Sep 17, 2017
Fetish

Pete was extremely satisfied with what he had done to both James and Marco and he knew neither of them would dare tell any of the other gang members what he put them through out of pride. Neither would risk the humiliation. The next day Pete was all dressed in his leather and boots and enjoyed time at home chatting online to friends and perverts whom he'd se...

Torturous Boots

by Fetish114 on Sep 17, 2017
Fetish

A story about perverted revenge Pete wasn't your average 19 year old boy. Unlike hanging out with guys and chasing girls Pete enjoyed dressing up in women's high heel boots and wearing sexy feminine leather. He was very much into the whole fetish S&M scene and enjoyed purvey nights at domination clubs and fetish balls. Pete lived with an old lady called S...

Sissy and Missy

by ChristopherDB on Feb 12, 2019
BDSM

Copyright 2019 Christopher D.B. * The central vacuum system made barely a sound as I made my way through the apartment. It was spacious and occupied the entire third floor. Although fully furnished and containing some of Countess Tori's personal items, she only stayed here a few nights a week. My feet were hurting, as the toe box on my pumps fit a little...

Sissy Shopping

by Candour on Sep 25, 2017
BDSM

My first story, finally edited and tidied up. I hope you enjoy it, I enjoyed writing it. --------- You were standing in your local department store in the make up section, looking for foundation. Not too sure what you are doing, and must have looked a little lost as one of the sales girls came up quietly behind you. She was a delightfully pretty 18 year ol...

A Sissy Saga Ch. 08

by Snurge on Sep 15, 2017
Novels and Novellas

In the gymnasium a practise was in progress. "One, and two, and three and four," Hardwick's voice brayed above the tinny jink, jink, jink of an elderly piano. Ten students arranged in a double row of five were dancing to the beat as he called it. It was part of Hardwick's routine. Groups of them came to him daily, either for dance, deportment or gymnastics...

Sissy Prince: Origin Ch. 03

by SatinSlip on Feb 13, 2018
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** Olivia pulled off his scratchy wool tunic. It had covered him to just below his cute girly ass. It was uncomfortable to wear, made by Orcs. Yet for some reason it turned him on. His tiny sissy bump was now revealed to the world. It was erect, yet not quite two inches long. He...

Sissy and Paul

by slowhand1234 on Apr 22, 2019
Exhibitionist & Voyeur

Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married sev...

Abuse my Sissy bitch

by Red10Dog on Mar 3, 2020
Fetish

This is a story from the sissy's wife. Telling you a story that happen a few weeks ago and it was orgasmic! So late one Saturday night I put my sissy bitch in a teddy, nylons, cock cage and a jeweled anal plug under his pants and shirt and headed out to the casino. I am not ready dress him out in public yet, but I am getting close. I decide to slut mysel...