Anal Plug Training Stories

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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...

Making Francesca Ch. 06

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

The next morning Justin woke Frank up, "Rise and shine sleepy head. Mistress Celia has decided that you can bathe yourself now since you've been such a good girl. Now let's get cracking." With that Justin reached down and unlocked the chain from Frank's ankle that was attached to the wall. He then clipped the leash on to Frank's collar and led him into the...

Maggie's New Life Ch. 04

by sadkins116 on Nov 20, 2018
Illustrated

Editor's note: this story contains scenes of incest or incest content. This story was inspired by the recent news about the NXIVM secret society, DOS. The lead character, Maggie, is desperate to rejuvenate her marriage to her husband of many years. She is befriended by a couple who are members of the cult. By the time Maggie realizes what the cult really is...

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...

Winning the Blonde Goddess Ch. 02

by spankednaked on Apr 30, 2018
BDSM

Fairhaven is a very multicultural city. Even the most casual of observers will notice that we have a considerable number of citizens who are of Chinese ancestry here. If you are somewhat more observant you will also notice that we have a sizable number of people living here who are Honduran, Korean, Nicaraguan, Russian, Salvadoran, Thai and Vietnamese. I...

Let's Go to the Movies Pt. 01

by coquette_redux on Mar 2, 2020
BDSM

God, this plug is so fucking heavy. She shifted in her seat for the 300th time since climbing into the passenger seat. She'd already been wearing it for half an hour and she could only be grateful that he hadn't tasked her to do something like grocery shopping with the plug the plug in...again. But sitting on it for this long wasn't much more comfortable....

Anal Training

by lydiayokomoto on Sep 19, 2017
Anal

Sex between my husband and me was wild for a while but, as I think happens to most couples, life, kids and finances wore us down and we returned to a normal once or twice on the weekend schedule. After my oldest started kindergarten, I started to work part time to help with the finances to at least reduce that part of the stress in our lives. Because I had a...

Rose Meets Her Master Ch. 01

by vickygirl on Sep 11, 2017
BDSM

I didn't need the money, but I made a profile on the sugar daddy website anyway. In the about me section, I wrote "Young female slave looking for master. Inexperienced, needs training". It wasn't long before I got a message in my inbox from a tall, attractive man with an incredible smile. "Saw your post. I'd be interested training you, and I'll pay you $100...

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...

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...