Butt Plug Training Stories

119,106 results
Orientation
Length
Source
Infinite Scroll

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...

Covid 19 - Pete Turned into Charleigh Pt. 04

by His_fag_wife on Jul 27, 2020
Transgender & Crossdressers

Red unlocked the locks, unclasped the clasps on the box and then popped the lids back on the two bottles of poppers, but popped them in place for later. After this first session being so much of a hit, she thought Charleigh might be in the box for some time, every day for the coming weeks, if the lockdown remained in place for that long. At least then the du...

The Normal Life, or Not? Ch. 01

by Denialxx on Feb 11, 2019
BDSM

The moment he walked through the door, she called. Alfred calmly walked toward the voice. "Strip." He does what is commanded of him. He kneels at her feet, hands behind his head as she taught him on the ride to the house, and waits. Mistress Erica knew he would submit. She already held his ready-made harness in her hand. She fastens the shoulder straps on...

A New Level of Submission

by Muffins127 on May 15, 2018
Anal

*Hello Mysterious reader, this is my first work so I'd appreciate any and all feedback, and ultimately, hope you enjoy the first part of this story. Big thanks to Sexyvibe who did a wonderful job editing my poor comprehension of the English language. I wrote this initially for my wife when she first started her training, to give her an idea of what was expe...

Anal Training - Lesson #01

by Jack597 on Sep 13, 2017
Anal

I hear your knock at the front door and open it to a vision of pure sex. Dressed in a short skirt, nylons and platform heels, you are the picture of classiness and sluttiness perfectly combined. Your skirt matches the color of your lipstick, and your dangly white earrings match your belt and platform heels. You're also wearing a very low cut top that exposes...

Making Francesca Ch. 05

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

It seems that I finally have gotten the time to finish posting this story. If you have not read the first four chapters, I highly recommend it as the story will make much more sense. Enjoy. As he sat there on the thin mattress, pondering his new outlook on life, Justin appeared with his supper. Justin opened the door to the cell and placed a folding chai...

Putamia

by DoxyTrainer on Jan 15, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** This is not a "pure" BDSM story, I did not intend it to be. It doesn't follow the "rules" even though I know them well. This story needed telling and is only for entertainment. Comments are welcome. *** The ringer jolted me from sleep. "Who is it?" I flailed for my glasses o...

Mistress Valeria Pt. 03

by BootyAllDay on Jun 25, 2019
Transgender & Crossdressers

This is part 3 of my Mistress Valeria series and I truly suggest reading parts 1 and 2 before this one if you have not done so. Thanks all for the support and feed back on the first 2. I believe this should be the best part. This is still around 90% accurate and I am looking to drag it out a little more by being more descriptive and let the story come to me...

Dinner with Sir

by sanbam469 on Aug 31, 2017
Exhibitionist & Voyeur

Got a call from my Dom with instructions about the tasks that I am to complete before I go to his house for additional training. The following tasks are as follows: He has ordered our dinner from a 4 star restaurant and I am to pick it up. When I leave the house to the restaurant I am to be wearing a very short black spaghetti strap dress. This dress must b...

Becoming An Anal Slave

by DJMarie on Sep 25, 2017
BDSM

I have always had a penchant for almost anything anal. I had met a man who claimed to have the same enjoyment in that regard. He told me he was a dominant, and me, being the naïve young girl that I am really had no idea what that meant. We began dating, and I had told him that I wanted to take things slowly, not rush into anything. So we began to see each ot...