Sissy Anal Training Stories

79,685 results
Orientation
Length
Source
Infinite Scroll

Buttermilk Pancakes Pt. 01

by numonebun on Jul 13, 2020
Anal

** Warning: Starts off slow, but so should anal :) ** The evening sun was slightly peeking through the dark curtains of their living room. It was Friday and they were spooning on the couch, watching cozy movies. "I'm getting hungry," he said as he pulled her deep into him and nuzzled his face into her hair from behind. "Do you want to cook or get something...

Blood and Ice Ch. 15

by shadow_raider on Sep 26, 2017
NonHuman

Chapter Fifteen: The Black Castle We headed back to the castle. Nothing was said. We got back and realised everyone had been silent. Peter pulled me into a hug, "Are you okay? I was worried!" "I'm fine Peter, are you?" He nodded, we kissed, and he slid his arms around me and started to kiss deeply sliding his tongue in my mouth. I felt a tap on my sho...

Master Takes His slut's Soul Ch. 08

by little-nymphe on Sep 26, 2017
BDSM

The story continues, I truly hope you have enjoyed reading the previous chapters. My chapters can be read in sequence, but they also each can stand alone on their own. Please enjoy and let me know what you think by your feed back and voting. Thank you, Little-nymphe Morning sunshine stirs me from my deep slumber. As I move to turn over to see what time it...

Billionaire and the Sisters Ch. 50

by SteveWallace on Sep 25, 2017
Group Sex

A note to readers: This is a long story that unfolds chapter by chapter through the eyes of two protagonists -- Mark and Elsa, and as in many of my other stories involves a growing spate of horny characters. Every ten chapters or so I will provide a short summary at the start of that episode to bring new readers up to date (see below). This story could appe...

My Berlin Summer Ch. 05

by cece3457 on Sep 17, 2017
BDSM

The trainer barked out a short, authoritative command in a language I did not understand. I looked at him in shock, not understanding what was required of me. I was standing before him, naked. In his left hand was one end of a six-foot, light chain leash. The other end was attached to a choke collar around my neck. In his right hand was a long, flexible swit...

Four F Girl Ch. 03

by SplendidSpunk on Sep 13, 2017
BDSM

I followed William to his mechanic and after transferring my possessions to William's car we headed off to lunch. There was no real conversation during this time other then remarking about how little I had brought with me. William and I ate lunch in a nice restaurant and he ordered for both of us. He explained as we entered the restaurant that I was only to...

Barbie's Service Ch. 01

by ts_candi on Sep 16, 2017
Transsexuals & Crossdressers

I looked at the letter in my hand, and read it again. "Dear Mr. Wu, we regret to inform you that you have not been selected for training for the Marine Corps. However, taking into account your desire to serve, we offer you the opportunity to train at the Prissy Boot Camp, following which, you will be posted depending on your aptitude. Contact Maj. Shirley at...

A Slave's Exam Pt. 01

by siannoncranberry on Jan 22, 2020
BDSM

This story is part 1 in a series. While all stories may be read independently they are best enjoyed as a collection. The first portion of this series sets the stage of a two day training extravaganza between a slave, her Master, and a Domme they often play with. These works are fiction, but inspired by real events between a D/s couple and friends. All partie...

Desperate Demi Ch. 03

by MTL17 on Sep 26, 2017
Celebrities & Fan Fiction

Disclaimer: This is a work of fiction. I do not know or own Demi Lovato, Selena Gomez, Taylor Swift, or any celebrity for that matter. I do not make any money from the writing of this story. ***** "Harder! Come on Dems, wreck that big fat ass of yours!" Taylor was very used to walking in on her girlfriend Selena getting ass fucked, but she didn't think sh...

Play Testers Wanted Pt. 03

by Lost Boy on Jul 30, 2019
Celebrities & Fan Fiction

All characters are 18 years old or older. Sorry for the delay. While editing this piece I decided to add content to flesh things out and not leave parts of Booker's training and quests down to a simple time jump. I hope you enjoy. ***** Home Sweet Home: It only took a few hours to get Snow's tower the way I wanted it. The perpetual thunderstorm outside ke...