Dildo Training Stories

67,245 results
Orientation
Length
Source
Infinite Scroll

Aficionado Gets in Trouble Ch. 02

by His_fag_wife on Jun 12, 2019
Transgender & Crossdressers

Mark cleared the clothes from the table, he wanted a truly clear picture of Pete being used in the stockade, knowing he'd get some great footage for his website selling the stockade frames, it would help sell some more without giving away Pete's identity from the side view. But he'd also get some head on footage for posting on the internet should Pete fail t...

The Program Ch. 02: Power Transfer

by bdsmtrainer88 on Sep 13, 2017
BDSM

Jess looked over her new pet. He was prepped with the ball gag in his mouth, collar and leash, anal hook strung up to the collar and locked in a chastity cage with a humbler. Eric was hers to do as she pleased. She stood over him fully clothed fighting the urge to strip down and just enjoy his hansom body. No, she has to have some restraint... she recalls ba...

Training of J Ch. 01

by Hologram22 on Sep 17, 2017
BDSM

Chapter 1: The Training Begins J bit her lip as she waited in anticipation. That was the worst part for her, the anticipation, worse even than the sharp pain that inevitably came. At least the pain faded in a predictable manner, and no matter how bad the pain was, she knew that there was no real, lasting damage done. But where the pain faded, the anticipati...

Training

by icklemepickleme on Sep 11, 2017
BDSM

Her tight, rear hole was stuffed full to capacity by the large toy. It was short by the typical standards of toys, going by the adage of bigger, aka longer, was better. Rather, it was a mere five inches in length, but it more than made up for that lacking with a diameter of almost two and a half inches. It had a short, rounded head that didn't allow her hole...

Betty Boots' Big Bust

by tomthumper on Sep 13, 2017
Humor & Satire

Betty Boots had just finishing re-applying her lipstick after Mr. Largeski's training session when she heard a crash from the back of the Fantasy Factory warehouse. "Golly!" Betty leapt to her feet, spilling her fashion magazines over the floor. There was another thunk and then Betty was sure she heard voices. She gulped and tugged her little white t-shirt...

The Training of Michael Ch. 05

by TheLadyVictoria on Sep 17, 2017
BDSM

jacob talked as he worked, patiently teaching michael what he would need to know to properly serve Mistress. "This time, you will stand in one of the niches...I'll show you which one...and watch. You will stand very still and watch. Just don't let any of the Ladies catch you looking directly at Her!" True to his word, jacob took michael to the dining room a...

Melanie Ch. 04

by StoryTeller07 on Sep 14, 2017
BDSM

Roberta arrives on the scene: Roberta felt pleased with her performance convincing Eddy to accept the hastily invented story. She had pretended to be in trouble, needing to escape the area, and was now in a plane being sent to a rich mans home as a servant. That's what Eddy had told her, but she knew the truth. The two stupid oafs had told her all about t...

Experiment 239 Ch. 04

by AmethystMelange on Nov 8, 2017
BDSM

Anthony was noticing a difference in Sophie this week, a difference that made his heart pound and his emotions soar, that made looser pants a necessity with how often Little Tony was standing at attention. She was as sassy as always, but there was a certain... air about her. As if she was happy in a way that she'd never been before. As if she felt content an...

Joanna's Contribution

by clarepanties on Sep 17, 2017
BDSM

A Contribution from Joanna: (as an adjunct to "Matt becomes Mattie"). * Mattie has asked me to consider writing something for you, the reader, especially about my experiences and feelings as regards the education that I have had from my now friend, Duncan. I am not as emotional as Mattie and tend to write in a more matter of fact style focusing on the ev...

The Masked Woman and the Mistress

by soppingwetpanties on Sep 14, 2017
BDSM

Warning: This story contains graphic scenes depicting humiliation and pain. This is a work of fiction. Names, characters, businesses, places, merchandise, companies, events and incidents are either the products of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coinciden...