Sissy In Chastity Fucked Stories

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A Very Public Sissy Adventure

by DivinaTellsAll on Jun 4, 2019
BDSM

At Madame Vega's instruction I had spent the last hour edging myself. This is not always an easy task for a sissy who is not allowed to stroke her clitty. The edging was primarily accomplished by the use of a vibrating wand inserted in my fuck hole, and an Hitachi wand that I could rub my clitty on, as I teased my fuck hole deep inside. I had been banned fro...

Shopping and Sucking

by Subkoksukr4u on Mar 2, 2020
Fetish

Matt was in the kitchen as usual preparing breakfast. He'd been instructed to prepare all the meals according to a specific menu plan each day. He finished the sauce for the eggs Benedict got on his knees and waited. He was wearing frilly pink crotchless panties and a matching bra, his bright pink CB 6000xs chastity device was barely peeking out between...

Transforming Brent Pt. 02

by sissymissyct on Jul 10, 2019
Loving Wives

Kept in Loving Wives to annoy the tiny dicked anonymous reviewers that love to trash everything they read (after they wank to it). *** I woke up Sunday morning with a painful erection in my chastity and the pumps still attached to my breasts. I reached down trying to find a way to ease the pain in my penis. Nothing seemed to help. Maybe Wendy will be up so...

Transforming Brent Pt. 03

by sissymissyct on Oct 8, 2019
Fetish

Over the next few days I removed most of my male clothing from the house and donated it to Goodwill. I met Wendy as she got out of work each day and we went shopping. The first time was for regular clothing. Skirts, dresses and blouses, leggings and shoes and regular lady's sportswear. Thursday it was lingerie night. I ended up with multiple bras and camiso...

The Inner Slut Ch. 07

by sub2femdom on Aug 22, 2018
Fetish

Chapter 7 - Lexi's Training Two weeks have passed. Amy is proud of Lexi's progress. They've spent about two hours each night practicing makeup, walking in heels, poses, and attire. Lexi even acts more feminine, especially when Mike is around. More than once, Amy has noticed Lexi staring at Mike, specifically at Mike's cock when it shows through his shorts...

Mistress Emma's Revenge

by sissymissyct on Oct 15, 2017
Fetish

Hi I'm Ken. Well I was, now I'm called Brenda. Here's a bit of my story for you. I hope you don't make the same mistakes I did. Because until I got caught misbehaving by my mistress, life was pretty good. At 38, I had a great job as an office manager in charge of 25 or so employees, mostly women, a really good salary, a nice office and plenty of job securit...

Luke Powers: Black Master Pt. 03

by scatwoman on Sep 16, 2017
Interracial Love

Brad's Ruined Honeymoon Starring: Brad Whitebread, Chastity Belle, Wesley Whitebread, Luke Powers and a special guest appearance by Mishi herself! (See the "XXX-Women" series, "Misadventures of Mishi" series and "The Perils of Greggie-Poo" for more Luke Powers & Mishi action!) Directed by Mishi. Most of you are familiar with Mishi favorite boytoy porno...

Mistress Monique Pt. 02

by bleedndkn on Sep 25, 2017
Fetish

This wasn't even my fantasy, I thought as I purchased the clamps, butt plug, heels and maid dress online with expedited shipping. The next day I brought the items in a backpack to Mistress Monique's apartment while she was at work. I put everything on then placed the butt plug in my ass and tightened the nipple clamps painfully so they wouldn't fall off, th...

The Birthday Party

by today_i_am26 on Jul 27, 2020
BDSM

Chapter 1 - The Negotiation We sat, the four of us, in a coffee shop on the high street. To the causal onlooker, we probably looked like university students meeting their parents for a catch up. The reality was something quite different. My Wife, Goddess, Dominant, Keyholder, had answered an online advert on my behalf; a couple looking for a Sissy to att...

The Sexy Cuckold Couple Pt. 08

by cuckcpl4play on Sep 19, 2017
Fetish

As I drove home from work, I could not stop thinking about how our lives as slave and slut had escalated so quickly. What felt like days ago, I was a powerful executive about to obtain my new and even more respected position, but instead I was driving home soaked in my colleagues urine as the new office demoralized submissive. My wife, who was the love of...