Sissy Plug Stories

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Infinite Scroll

Sissy Stretching for Princess T

by Subboi23 on Apr 15, 2020
Fetish

I balance my phone up against my dresser, take a deep breath and wait patiently for further instructions. I had already received orders to be dressed in my pink negligee with no panties (or underwear of any kind) on and my butt plug inserted by 7 pm. I was in position 10 minutes early and was attempting to clear my mind and focus solely on obeying whatever o...

Domina Katarina Goes Shopping

by pbs444 on Sep 17, 2017
BDSM

Several days ago, there was an e-mail in my inbox. It was of course from my Domina, Katarina, because the e-mail account is for her exclusive use, when she wishes to communicate with me. Because I am her sissy slut, and from time to time she finds ways for me to prove my usefulness to her. The e-mail read: "Hello, sissy slut, I have decided I wish to go...

Re-tooled

by Sissyhalo on Mar 13, 2018
Transsexuals & Crossdressers

Re-tool your life. Re-tool yourself. Sick of not getting what you should? Sick to fucking hell of all these assholes getting with hot people they really don't deserve? Sick to hell of Liberals and Feminists making impossible to jump through hoops so that only the privileged people get to be happy? Sick of being a goddamned incel? Look we all know that...

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...

Halloween Pool Party Pt. 05

by sissymissyct on Sep 14, 2017
Fetish

We arrived home and Annie greeted us warmly, then stepped back to get a good look at me from head to toe, having me turn to see the full look. Satisfied with what she saw, I was told to bring in my clothes, put them away and then pick something pretty to wear as dinner would be ready shortly. Miss Maddy and Annie headed into the main house and I went about m...

The Office Ch. 04

by EasilyConfused on Jan 23, 2018
Transsexuals & Crossdressers

There were six screens in total, one for each of those being monitored. Their heart rate, blood pressure and neural receptors all key indicators. The technician made gentle adjustments to the controls in response to certain measurements that she noticed on each of the screens before her. Behind her a woman in a business suit watched on. Paula Hamilton was sk...

My Wife Takes Me Much Farther

by Godscountry on Sep 26, 2017
Transsexuals & Crossdressers

It's been three weeks since my wife turned me out at her book club and turned me into a cumslut. That event seems to have really opened up my wife's imagination and made her hunger for more dominance over me. For the last three weeks, she's kept me locked in chastity, even though our deal was that I would be released after the event. She's also made me kee...

A sissy visits the Headmistress

by maturesubmale_for_F on May 12, 2020
Transgender & Crossdressers

1. Miss Stern delivers both punishment and pleasure I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the...

Covid 19 - Pete Turned into Charleigh Pt. 02

by His_fag_wife on Jul 13, 2020
Transgender & Crossdressers

Again it was as though she'd slapped him back into reality, just as she intended, she'd noted his angry response earlier that day and wanted to trigger him again, but trigger him much more this time. She simply would not accept rudeness or attitude from him. Pete had to realize that as Charleigh took over his psyche, that she would need to be more and more s...

Tales of Sub Asian Sissy Ch. 03

by subASIANsissyJADE on Apr 23, 2019
Transgender & Crossdressers

(Thanks so much for taking the time to read my story! This is just my third post and I'd love to hear any feedback, questions or comments. Also, please feel free to contact me if you just want to chat with a very submissive asian sissy. XXX, jade) *** While it's only about fifteen minutes away, the drive back to my apartment seemed to take forever. I had t...