Sissy Anal Training Stories

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Infinite Scroll

The Business Trip

by WRJames on Sep 13, 2017
Anal

"I can't believe I let you talk me into this." Eileen was starting to sweat seriously now. It had been chilly in New York, even colder on the plane. Her little white ribbed turtleneck had been just right. But now, in the middle of the Arizona desert, she was dying. "I thought it was your idea," Tom countered. Actually, it had been the two of them. They had...

From Intern to Sex Slave

by HandcuffGirl on Sep 19, 2017
BDSM

Authoress's notes: For those of you who've read my Imperial Prostitute & Jedi Submissive series, this story will seem a bit familiar, as I was looking at a non-Star Wars version of that story line. For everyone else, please read and enjoy all of my stories, and please leave me feedback, public or via email. * Trish Ivory strode confidently into the off...

Amber's Enslavement Ch. 01

by dweaver999 on Sep 12, 2017
Sci-Fi & Fantasy

Chapter 1 Awakening The girl started to wake up. She was young, at least in the eyes of some cultures. In the eyes of others, she was well into adulthood. On her home world, she was considered to have just barely reached the age where she could make life altering decisions for herself. The people who brought her here always took those who were legal on the...

Sex Wrestling Couples

by Femfightfan on Sep 26, 2017
Fetish

Laurie and Don had been living the life most young couples could only dream about. Travelling the world vacationing in the most exotic locations the world had to offer, dining in the world's finest restaurants, and just living a care free life for the most part, the young couple had no thoughts of saving for the future. Don was a pilot for one of the more su...

Ann: The Married Years Ch. 21

by mimaster on Jun 11, 2019
BDSM

© 2019, All rights reserved -- mimaster ~*~*~*~*~*~*~ Ann could feel something tugging at her neck but she didn't understand, at least at first. Opening her eyes, she was startled by her surroundings. Everything seemed shaded in a deep blue, like she was wearing a pair of tinted sunglasses. Her pupils were having trouble adjusting. "Where am I?" she whisp...

Ah...Does Size Matter...

by Kalimaxos on Mar 9, 2020
Loving Wives

This story is the property of the writer Kalimaxos. This is a bit longer than I usually write but breaking it up does it no justice. I hope you read through it. It's not a cuckold fest, not a swinger story. But it's the story of a woman from her point of view. It's a tribute to a young woman of my youth I never had a relationship with but found later fro...

Happy Anal Slut

by wiley4377 on Dec 17, 2017
Anal

Two years after Wiley was seduced and discovered anal lust, he was receiving hard cock three to four times a week. His two male bulls would call and visit his place over the garage. Sometimes he would fuck both the same day but never together. This is one day in the life of horny Wiley. Finally, Wiley's first year of college was over. He was relaxing at th...

My First Anal Sex

by subwryter on Sep 13, 2017
Anal

4pm... One of the things I want to experience the most is anal sex. Haha, I've just admitted to myself that I want anal sex. Now it is just a matter of bringing it up to my husband. He isn't the most adventurous man. I met him at a high school reunion. I hadn't known him at all in high school but he did admit to seeing me around. "I remember you having lon...

The Sim

by justsomeguy42 on May 26, 2018
Fetish

Disclaimer. I'm extremely into anal and free use so my stories will practically always involve them as well as rough/abusive sex , humiliation and demeaning of women, if that's not your cup of tea, give this story a pass. So I caved in, after hearing everyone gush about the VR Sim that just got released, I decided to finally give the thing a go. I made my w...

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Sally’s Wish, Anal Education

by HeyAll on Sep 19, 2017
Anal

Part 1 of 3: Sally's Wish Sally updated her wish list at the very last minute. It was an annual thing her friends liked to do. Instead of having to buy everyone a bunch of gifts, each person would be secretly assigned to one person. They were all career oriented adults, so the price limit was $300. Not too high. Not too low. Her wish list was fairly bas...