Chastity Belt Anal Stories

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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...

College Ponygirls Ch. 05-06

by Sarahcheer on Sep 12, 2017
BDSM

Chapter 5: First Day Training Sarah and Emily had slept for a full day in their bindings, and were awoken at night by Ms. Westgate and her trainers. The girls had spent the previous 4 days in sleep deprivation chairs, and had been forced to the point of exhaustion. Their minds had been invaded by a new mind control program, and both girls had become reprogr...

Helping a Friend's Loneliness Ch. 01

by Bibliophile on Dec 3, 2019
BDSM

Author Note: I'd completed three chapters for the girl that could not cum and I think that is enough to ask for from any interested reader, but there was more to write for pun'kin in my imagination and I also saw a way to tie her new goal in with another heroine from the past that I couldn't resist. But since the first problem is solved (finding a selfish v...

A Trip to Remember Ch. 01

by marykay9 on Sep 16, 2017
Transsexuals & Crossdressers

I live in Los Angeles and don't get much of a chance to practice my hobby of cross dressing. Once per year however, my company sends me to an industrial convention and I take full advantage of the opportunity. This year I was to travel to San Antonio, Texas, to attend a conference at a large hotel located on the River Walk. I packed two bags, one with my b...

A Platonic Relationship Ch. 06

by The_Technician on Apr 8, 2019
Sci-Fi & Fantasy

PLATO is the most powerful computer ever... grown, but he has been able to hide that power from everyone except Marcella and Richard. In this final chapter, he is forced to reveal the full extent of his power. This story stands- more or less- on its own but might make more sense if you have read the previous chapters. This final chapter again gets a littl...

Letter from Thomas Circle

by justincbenedict on Dec 3, 2019
Anal

Dear Shoeblossom Mistress Spurs is the most imaginative dominant I've ever known. I have been with various Masters, Mistresses, Dominas and Goddesses throughout Europe, Saudi Arabia and these United States, and except for one I met in Gstaad, there's never been one quite like Spurs. Spurs is only about five foot one, but she has ample breasts and fire-engi...

LustJail at Fetish&Bondage Expo

by LockUpTheWolf on Jun 9, 2020
BDSM

I was in a pub with a few friends, Molly amongst them. We had a long-lasting friendship, with, sometimes, benefits. Don't get me wrong - we were not in a permanent arrangement of this kind, but we sometimes would booty call each other. It lasted a few years but never when one or both of us were in relationships. We learned what we liked and we experimented t...

Allie's Encounter on Craigslist

by allycd on Sep 13, 2017
Transsexuals & Crossdressers

Let me start off by saying this is a 100% true story. I know there's some that will try and pretend to be real but are in fact not. There's no real way for me to prove it, but nonetheless I just wanted to share my experience. About a week ago I posted an ad on craigslist "19 y/o Asian CD looking for a dominant top", asking for their pictures and stats. Aft...

Infidelity and Chastity Ch. 04

by rockbohunk on Sep 15, 2017
BDSM

"I guess that you will either have to ask me for help when I am here, or jump in the shower." Sara shook her chains and looked up at Rick, "Please Ricky, I promise not to do it again. Please?" "Promise?" Rick asked. "Like you promised not to cheat, or to lie? You should be damn lucky that it's not the middle of summer. You would be tied outside to your Pil...

Arcadia Castle Ch. 09

by Hal1031 on Jun 26, 2019
BDSM

Chapter 9: A Visit to Dr. Chastity Each of the chapters in this series may be enjoyed as standalone stories, but the events and characters are richer within the context of the whole story. ------- I was startled to find Cole stretched out on my lounger the next morning, his intense gaze trained on me as I attempted to stir myself awake. "That's a lit...