Anal Plug Training Stories

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Infinite Scroll

Early Training

by lilsubalex on Sep 11, 2017
BDSM

It has been a long time since i've thought back to the beginnings of my training as a submissive. When i think about it, there were so many things and many that i'd forgotten! It was only an online relationship ... so all by my own hand... but was emotionally very attaching. i'm still amazed at how much so. Very early on my first instruction was to complete...

Mistress & Her Madam Ch. 01

by BlackBandit20 on Sep 17, 2017
BDSM

I got the text message... "You are to be trained, take the necessary steps...arrive at 9p at the usual locale. When you arrive; undress and come to the training room. Kneel and await your instructions." It excited me to know that my Mistress deemed me worthy of training, as it has been sometime since I had any training at her hand. I raced through a host of...

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...

Chronicles of the Special Stretch

by AngelPie4Mongo on Sep 14, 2017
Anal

CHRONICLES OF THE "SPECIAL" YOGA STRETCH My boyfriend/ live-in lover/ best friend of three years had mentioned anal sex many many times. We had tried it 2 or 3 times and had to stop because it was VERY painful for me! A few weeks ago, I had a short discussion with him that I didn't know if we'd ever be able to have anal sex unless I went through some "anal...

Return to "Weekend School" Ch. 10

by cynthiablaine7 on Nov 7, 2017
BDSM

This story does involve bodily functions so if that is not something you find compatible with your interests, read no further. It features spanking and caning, so has been placed in the BDSM category but has equally significant Fetish contents. All characters are over 18. ***** Melody Haynes, in her early 50s, awakened and was surprised momentarily to find...

Pleasure Cult Boot Camp

by fannypack on Sep 16, 2017
BDSM

"I signed up for this," she told herself. But standing naked in the tiled room surrounded by trainers, Red was beginning to feel doubtful. This was not the time for fears though, it was too late. Last night she had come to the convention and followed all the procedures: signed consent, video consent, verbal agreement to all parts of the training. And the las...

Kinky Couple Ch. 02: The Contract

by c1999 on Sep 17, 2017
Fetish

Authors Note Please be aware that while this series of stories will get VERY dirty/kinky, some chapters will be milder than others. The specifics of each chapter will be listed in the preface so that you will know what the story contains. Constructive comments are always welcome, especially from women as I'm always curious if I've captured anything that mig...

Her Favorite Anal Tease

by EclecticDiversity on Sep 16, 2017
Anal

He sat in the chair, naked except for a leather cock-ring that separated his balls, holding onto this thighs, so that his ass was totally exposed and puckered up, waiting for her kiss. She was in her endless teasing mode; as much as he loved it, she needed to do this more than his desire. Annie was 5'4", 38-25-37 and the most natural of Redheads – Nature's M...

A Proper Young Woman's Guide to Anal Etiquette Ch. 04

by lordodie on Sep 18, 2017
BDSM

Disclaimer: The following is a work of pure sexual fantasy and is intended for adult audiences ONLY. If you are under the age of 18, please stop reading NOW and go tell your parent and/or guardian that you need stricter internet supervision. Any physical resemblance to a real person that any fictional character herein may bear is probably intentional and is...

My Little Kink

by greeklovevanc on Sep 16, 2017
Anal

I consider myself not a bad looking guy, with full dark brown hair and about 5' 10" tall. I'm lean from all the triathlon training and obviously fit. I have no trouble conversing with the ladies and have a few female friends, both at work and at the Triathlon club. But because of my daytime job and triathlon training I have never found time to fit in a relat...