Butt Plug Chastity Stories

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Teased, Denied and Sissified Ch. 04

by subbieman on Sep 12, 2017
Fetish

Quick Recap It had been nearly two weeks since Ashley caught me trying on her panties and I was now wearing a fresh new pair every day along with a bra as she encouraged me to find my "inner-sissy" and explore my fetish. I had also learned that she obtained more pleasure from her toys than my cock and, as part of this "exploration," she had decided it was b...

Scenes from a Marriage Pt. 02

by DopamineFan on Mar 3, 2020
BDSM

If you've read the first part of this story, you know that my wife and I had just recently discovered that we both love it when she dominates me. It had been a week and a half since our first scene. We'd been continuing to talk a lot about what we enjoyed and what we didn't, and she had been spending a lot of time online reading and learning about D/s. We ha...

Almost Damsel Almost in Distress

by shawnavinyltv on Jun 19, 2018
Transsexuals & Crossdressers

Finally! I had the day off from work and I planned to spend it indulging two of my favorite activities... crossdressing and self-bondage! I've been dressing since I was 10 years old, and about the only thing that was more exciting than getting all femmed up... was locking myself into some strict bondage and struggling to get free! I lived in a small apartme...

Teaching a Colleague

by MisstressMadaline on Feb 26, 2019
BDSM

This is the third in a series but has been written so that it can be enjoyed both on its own and as a sequel. Have fun! _*_*_*_ I could feel her eyes on me. It felt as though they hadn't moved for the last two weeks. True to my word, I hadn't even acknowledged her. I glanced up and saw her eyes flicker down quickly, as though she had been caught stealing....

Master Jakob and Seth Ch. 08

by and9993 on Aug 14, 2018
BDSM

Chapter 8 - Plugged and Milked Training Day 5 - Wednesday I woke up next to him with one of his arms still holding me. I stayed motionless. I knew it was time to get up and start my morning routine but I wanted to stay in this moment as long as possible - being held with his cum still inside me. I reflected on the decision to commit to him. Although there...

A Slave Meets his Goddess

by atrickofthelight on Sep 17, 2017
BDSM

He awoke from his long nap when the plane touched down, and felt his stomach tingle. It wasn't from the landing, though: after several months of chatting with his Goddess, today was the day he would meet Her. He shifted in his seat, the butt-plug becoming uncomfortable after several hours' wear, and waited impatiently for the plane to taxi to the walkway whi...

Feminizing First Step Ch. 05

by antares34 on Mar 30, 2020
Transgender & Crossdressers

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. Chapter 5 Today began like any other. I awoke in my bed with my wireless earbuds still in my ears. The sissy hypnosis audio track was gently playing...

Sissy Girl Forever Pt. 01

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

The call from Mistress Andrea made my day. I hadn't seen her for over a week and was looking forward to playing with her & having my chastity finally removed. You should know that Mistress and I have known each other for many years and have I always enjoyed being her sissy sub. Lately she has been training me to be more feminine in appearance. I have been r...

The Visitor Ch. 02

by RobertoTropical on Sep 18, 2017
BDSM

Later that afternoon I found myself securely spread-eagled face-down on our bed with my mid-section raised by three pillows. As the two of them were tying me down, M. asked Emma if she wouldn't mind removing the giant steel butt plug. "Won't he feel empty and denied if we take that pleasure away from him," Emma asked. "You need for him to get something out...

Hotel Porter to Private Maid Ch. 02

by KinkyBiLad on Sep 12, 2017
Transsexuals & Crossdressers

Thank you for your comments and feedback about my first chapter in this series. I hope you enjoy this one just as much. Please leave comments and tell me what you think. Thanks KinkyBiLad "Next time I want you on your knees when I come up here" Matthew shouted, as he swung the paddle one more time on to Alexi's ass. Alexis couldn't do anything, her hand...