Plug Training Stories

51,411 results
Orientation
Length
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Infinite Scroll

Mike's Performance Evaluation Ch. 02

by mistressjanem on Sep 17, 2017
BDSM

It had been a week since his first performance evaluation and training session. The department was empty, as most everyone had either left on time to start the long weekend early, or taken today off entirely. Mike closed the last file on his desk, leaned back in his office chair, and sighed deeply. Since his first and only training session a couple of week...

Submission Pt. 03

by aleigh10170609 on Apr 10, 2018
Fetish

Annie stood in the shower after she turned the water off. She was shocked that Alex had taken it as far as he had. She was used to a little love tap here or there during sex, but he'd never spanked her before. She was so embarrassed that she had let him, but more...she'd been wet as soon as he told her what to do—standing in the middle of the kitchen as he s...

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...

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...

Sheila's Training Ch. 01

by CeliaisAliena on Sep 15, 2017
Anal

Not for nothing are "Ghost World" and "The Doom Generation" my favorite films. I was made for a stark black bob long before I ever got one, before I saw those movies and even before I discovered black hair dye. Without it I might have ended up looking something like Lotte Lenya in "From Russia With Love." Goddess bless Manic Panic!! It's more than the hair,...

Enduring Dreams of Submission Ch. 16

by Player One on Sep 19, 2017
BDSM

What a wonderful evening the three of us had. First, a dinner of fantastic charcoal broiled ribeye steaks, cheese stuffed potatoes, and broccoli smothered in butter and lemon juice. We also had two glasses of an astonishingly wonderful red wine that Master Bill said was a home brewed private stock that would challenge any of the world's best but would remain...

Breaking Drake Ch. 10

by TheDragoness on Sep 15, 2017
Novels and Novellas

*** Author's note. This intro to this chapter is mostly story building. This is so that the powers Raell and future character have makes sense. I am limiting the background information, but if you want more information, message me. Thanks!*** Drake stayed curled up, sobbing softly, for a few more minutes. He was filled with self-pity, wishing to have his...

Anal Training - Lesson #02

by Jack597 on Sep 14, 2017
Anal

We decide to meet at a hotel, as both of our houses are busy lately with the kids being at home and our spouses off. It's been a while and both of us are anxious to get together. You've been using your butt plug trainer for a few weeks and now think you're ready for the next phase. I know I'm ready to take you there. We meet in the downstairs lounge for som...

Jessica's Anal Training

by rockbohunk on Sep 13, 2017
BDSM

Jessica was a young submissive with a lot to learn. Although she tried to please Rick, she had always refused his anal advances. Rick had heard enough of Jess's excuses, today was training day. Jessica completely undressed for Rick as he handed the leather wrist and ankle restraints to her. Jess strapped on her ankle restraints just like the many times t...

Anastasia's Journey Ch. 03

by DJMarie on Sep 14, 2017
BDSM

Hank led Anastasia into the house and straight to a room that contains many things that are familiar and yet unfamiliar to Anastasia. There is what looks like a doctor's examination table only lower with stirrups in the center of the room. There is what appears to be an IV stand next to it. There is also something that looks like a traction handle above the...