Sissy Anal Training Stories

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Betrayed by Her Stockings

by NylonDreams on Aug 31, 2020
Loving Wives

Betrayed by her Stockings As he waited for the whore to come home, he reviewed their life together and the last month since he had discovered her adultery. He had thought he had found a kindred spirit, one who loved the same things he did sports, travel, eating out, walking, theme parks and nature. They shared the same sense of humour and loved to surprise...

Daddy and Little Meet First Time

by Hisgirl66 on Jun 1, 2020
BDSM

My Daddy and Owner set me a task to depict a first experience and how I envisage it. I wrote this for him, upon reading it, Daddy extended my task to posting the story publically as he enjoyed it and wanted to see others reactions to my task. I have never posted anything publically and I appreciate Daddy for pushing me to share this with the world. To add...

Terra Quest Ch. 18

by Kevintall on Oct 12, 2020
Sci-Fi & Fantasy

Cleo was a little disgusted with herself. 'I don't think what I did on that boat was right,' she thought as she sat on the bus on her way home from work, 'perhaps I shan't play that game any more.' But after she had eaten her supper and had a bath she decided to give it one more try. 'Perhaps the next level won't be as pervy,' she thought as she sat on he...

Born to Be Ch. 06

by DamienDeath20 on Mar 9, 2020
Transgender & Crossdressers

A.N. Here we are again with more Born To Be!! :D Thank you all for waiting for these things to be updated, plenty more chapters are on the way! The Following Contains: Big black lady fucking her little white boy up with a strap-on. Ever seen ultimate surrender? Expect that up ahead ;) Enjoy the chappyyyy! ***** For a long time, Ashley actually con...

Life as a New Hire Ch. 41

by FinalStand on Sep 25, 2017
Sci-Fi & Fantasy

Editing magic performed by KJ24 and Shyqash, plus contributions by the regular gang of brigands and neer-do-wells Love is like a crossbow quiver. You only have so many bolts to shoot before it runs out ***** {11 pm, Monday, August 25th ~ 14 Days to go} {Late that night with Hana} "So, who was the guy who gave you this?" I looked over at Hana while runni...

Th Undercover

by o_girl on Sep 12, 2018
BDSM

I have always had a fascination of Pauline Réage's 'The Story of O' -- and the film(-s) -- and the Crepax Comic about it. In the following I have tried my hand in a sort of updated 'fantasy' over the same subject. I hope you will enjoy it -- and excuse errors etc. as English is not my native tongue. You are welcome to repost, but please have the courtesy to...

Dominating Annie

by altcontrol on Sep 13, 2017
Anal

[Authors note: I write the sort of stories I want to read, I hope you enjoy them too!] * You hear the normal story all the time. It could be a drunken romp where two blushing newbies try it out on a whim. Maybe it happens on a night of slow seduction, planned for months, when a long married couple try and reinvent their sex life with new penetration. This...

Camilla Ch. 024

by MawrGorshin on Sep 13, 2017
First Time

Camilla removed the come-soaked paper towels from the bed and threw them away; then she slept for a few hours, waking up around 4 PM. She looked at the hidden camera in the hole in the wall above the head of the bed, and saw the camera move slightly. "He's ready for yet another show," she said, then she put more paper towels in the middle of the bed. After t...

My Good Fortune

by Gaucueret on Sep 14, 2017
Anal

What can I say? I love anal! I really do! I don't even know how I grew to love it. It just happened. I remember seeing it for the first time in a video and thinking it was interesting. Before I knew it though, it was in every other video I watched. I mean, I love regular fucking as well, but there's an animal quality to anal that pussy fucking can't seem to...

The Right Side of the Hill

by Penelope Street on Sep 19, 2017
BDSM

(c) 2005 by Penelope Street There it was again. For the fourth consecutive week the same ad had appeared in the personals section of The Scene, a local rag dedicated to the seedier edge of society. I routinely perused the personals. Once in a while, I stumbled upon an arousing one. Most often though, I found the racy little blurbs amusing instead of excitin...