Sissy Butt Plug Stories

100,438 results
Orientation
Length
Source
Infinite Scroll

Cockland Island Pt. 05

by Sissyhalo1 on Feb 3, 2020
Transgender & Crossdressers

Waking up like that I think my brain wanted not just more but to place everything that happened to me in an order that I could handle. So deeper into sissyness it was. Playing with my butt plug until I was edging myself and losing myself in it. Abby showed up. Rolled a joint and watched me. "C'mon Nikki, up, let's get you fed and working out." It was h...

Renee's Training

by UniversalReader on Sep 26, 2017
Transsexuals & Crossdressers

AU: The age of the characters in this story are not listed so that you can make the age fit you're desired age group. Assume by default that all characters are over 18. Nathan was an average teenage boy. He was slightly shorter compared to most of his friends at school; but other than that he was average height. He was thin, he wasn't very muscular but h...

Tales of Sub Asian Sissy Ch. 01

by subASIANsissyJADE on Apr 3, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** (I'm new here and this is my first post! I'd soooooo love to hear any feedback, questions, or comments! Many thanks, xxx, Jade) ***** I wore exactly what he demanded - he told me to dress like a regular girl... he told me he had nosy neighbors and, being a married man, he...

Family Chastity Story Ch. 02

by antares34 on Jul 3, 2019
BDSM

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+. ***** Having grown bored with how things were progressing with my sissy son, I have recently ventured into a new and fun project –filming and distribu...

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...

Sissy's First

by CDJessie on Mar 7, 2018
Transsexuals & Crossdressers

This is a work of fantasy. (I wish my gf would do something like this to me.) *** I'm woken up to the blinding sun after Sarah rips open the curtains to our hotel room window. We were up half the night fucking our brains out, and I was pretty hangover "Fuck, you couldn't wake me up like a normal person instead of blinding me?" I ask. "Don't take that fuck...

High School Dilemma Ch. 03

by LaurenWestley on Sep 15, 2017
Transsexuals & Crossdressers

(Authoress's note: of course all disclaimers are still in place regarding characters etc. This particular episode is very XXX with pee scenes etc. I suggest those who don't like this kind of story not to read on. I know I make both grammatical and punctuation mistakes. I promise all of you I will try harder every time to get it right. Hey what else can a sub...

Neighborly Relations Pt. 02

by grizzley123 on Jan 15, 2019
Fetish

NOTE: I always appreciate comments. You can read my slightly longer message on the first part of the story, but the gist is... I like my themes, you might like other ones. But I always enjoy comments, regardless of their content. **************** It helps to read part one where my neighbor starts to take control of me by using his incredibly hot step-daugh...

Ms. Alexandria - Interview No. 02 Pt. 02

by gasissynora on Dec 3, 2019
Transgender & Crossdressers

This is the third part of the Ms. Alexandria series and part two of The Second Interview. I believe it will stand alone, but will make more sense if you read the earlier parts of the story, particularly Part 2a. This part starts with the last paragraph of the previous part. Ms. Alexandria: The Second Interview -- A day out. Part 2b Mistress walks up behind...

AliExpress and Sissy Downfall Pt. 08

by His_fag_wife on Jul 10, 2018
Transsexuals & Crossdressers

Emma's gaze swung around the room taking in as much of the contents of the room as she could. So many of the items being completely unrecognizable to her. "Close your mouth my dear little slut or I may have to put something in it." "Yes Master, sorry Master, it is just an amazing collection." "It is, isn't it and we'll get Charlie to choose your new plug...