Sissy Butt Plug Stories

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Orientation
Length
Source
Infinite Scroll

Sissy Dust Pt. 01

by Sissyhalo on May 29, 2018
Transsexuals & Crossdressers

All characters are over 18 years of age. ***** I'm not a genius or anything but I did get a decent job out of university with my bachelors of chem and started working in a cosmetics company. No not the testing division but in formulations. And it's a boring job really past the actual chem coolness of seeing reactions happen in new things and the way thin...

Behavior Modification Institute Ch. 13: Final

by NancyPan on Sep 25, 2017
Fetish

Thanks to all of you who encouraged me to continue writing this story. Stay tuned for new stories. Please vote! All respectful feedback appreciated. ***** "Wake up, Nancy. Rise and shine. Time to get up, sissy." I hadn't heard the key turn in the door lock, and I hadn't heard Ms. Jensen enter my room. I sat bolt upright, then remembered that I was wearin...

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...

Meeting Miss Kate

by princess_nicole on Sep 16, 2017
Transsexuals & Crossdressers

been reading on this site a lot, my Mistress had me write a story of my own for Her, and i thought i'd post here. it's my first attempt, i know it's not terribly long, but hopefully some of Y/you will like it. ---------------------- i had been talking with my new Mistress online and via text message for about a month and a half now. my first Mistress reall...

Lexi's Date

by Sissy_Sammi_ on Dec 24, 2017
Transsexuals & Crossdressers

As Lexi scrolled through the photos of lewd sissies, she felt her sissy cock press against its pink cage. She wiggled her butt against the chair to feel the plug that was in her. She felt the soft panties against her smoothly shaven bum, and smiled her pink lipstick covered smile. She checked the time, 1:23 AM, and decided that she needed to finish up and ge...

Slave History

by timeagain93 on Sep 17, 2017
BDSM

These are my recollections of my slave history. Four Goddesses have dominated me. I'm writing this to let my current Mistress understand my story. Mistress D read "Variations" magazine and spanked me with a wooden spoon. She tied me naked to a chair and blindfolded me. She made me sit there in silence. I was wearing her panties while talking on the phone w...

Anal Training Ch. 02

by Catchandrea2397 on Jan 20, 2020
Transgender & Crossdressers

Are you ready to be a good obedient sissy pet? Well shall we begin day 2 of training. Have you got everything I asked for last time? Good. Today you'll need: - Bra and panties - Lube - Butt Plug - Vibrator Get these things and lay them out on the bed. Go shower. I want you nice and clean. Clean now? Good. Now I want you to crawl naked to the...

The Dominatrix Order Pt. 04 Ch. 03 - Femdom

by Jwwsmith on Apr 23, 2019
Fetish

Sixteen days before the next supply of Medication 42 was due to be manufactured, General Callisto paid another visit to Femininus. Upon the General's arrival, she was nonplussed when she received an invitation to have drinks with Isabella at her castle. She arrived at Isabella's residence that morning, dressed in a modest black knee length dress. Servant Bul...

Dominating Ken Pt. 05-08

by oneguy4fun on Sep 26, 2017
BDSM

PART V TEASED AND ENTRAPPED! Monday evening Kareena logged on and was delighted to see an e-mail from Ken. She had instructed him not to write until her present arrived and she knew that it had not arrived. She was curious as to what he had to say. She wasn't even halfway through the e-mail and her pussy was hot and beginning to dampen. It was obvious that...

Neighbourhood Terror to Sissy Pt. 24

by Fibaro on Sep 14, 2020
Transgender & Crossdressers

Chapter 26 Marcy was a nerve wreck walking out in public dressed as she was carrying the big pink bags stuffed to the brink. The street was relatively calm yet coming out of the outrageous store with those bags she instantly drew everyone's attention. The bus stop was right outside the store and yet those few steps towards it were the most embarrassing step...