Sissy Dare Stories

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Orientation
Length
Source
Infinite Scroll

Truth or Dare Takes a Turn Pt. 02

by Cutiepie183 on Sep 14, 2020
Transgender & Crossdressers

Morning rises and I must have eventually fallen asleep during the night as I am awoken by a swift and stubborn kick to the stomach. "Rise and shine sissy boy, you've got a lot to do today" sprooked Luke as he looked down at my filthy curled up body. I peel myself off the hard cold concrete of the patio and instantly feel the pain of my cock being squeezed...

Truth or Dare Takes a Turn Pt. 06

by Cutiepie183 on Nov 2, 2020
BDSM

I wake up in a small strange concrete room, still wearing the pink latex that Master Brent bought for me but this time without the hood or the gag. I look down and see masters foot on the concrete floor tapping. As I look further up I see his tall muscular body dressed in tight leather and the big smirk on his face as he says "well looks like our little bitc...

Neighbourhood Terror to Sissy Pt. 07

by Fibaro on Apr 23, 2019
Transgender & Crossdressers

Mark regained consciousness when Stephanie pressed her lips against his and started pushing his load of cum in his mouth. He had only just sucked a load off of Linda's toes and now he was swallowing yet another one. Every time he came here he seemed to get stuck with a taste of cum in his mouth. Only made worse by the way in which he was fed the load. Well a...

High Society Sissy

by beyondkink on Sep 11, 2017
Transsexuals & Crossdressers

I guess I can say I was one of the lucky ones. Fresh out of an ivy league school with a degree we were met with two different tales. "Sorry, you're over qualified," they said. Or we would hear, "We're looking for someone with more experience." An alum that I had befriend however was able to land me a waiter position in a posh New York country club that ca...

Neighbourhood Terror to Sissy Pt. 10

by Fibaro on Jun 10, 2019
Transgender & Crossdressers

Chapter 12 Mark had just about time to put his dildo down before the door to his room opened. His hand was still wrapped around the base, and well there was no real way he could ever hide anything of what had been going on. He was caught red-handed and could only really look at his girlfriend, or rather his ex-girlfriend in horror. After all, why else than...

Another Submissive Slut Ch. 04

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

She was leading me unerringly to my place. How did She know where I lived, I wondered briefly before the effort of walking with such a large plug in sissy hole forced my attention else where. Panting more from nerves than the walk I quickly opened the door to the building to get us in and off the street. Almost immediately my landlady was upon us. I nearly s...

Submitting to the Neighbour Lady

by Stillherer on Jun 8, 2020
BDSM

I went to high school with the Post twins in the late 60's. Tommy and Belinda Post. The Post twins were new to our area and it was rumoured that their father wasn't with them. It was our senior year and being 18 we just wanted it over with so we could get on with being adults. Belinda never gave me a second look but before he knew better Tommy struck up a te...

Hubby Drop To Thy Knees! Ch. 01

by Ashesh9 on Sep 17, 2017
BDSM

CH1. : HUSBAND, DROP TO THY KNEES!!! IMMEDIATELY! "Husband drop to thy knees!!! Immediately knave, dost thou comprehend???" her right hand shot out & expertly boxed the ears of the blond, blue eyed Greek God standing deferentially to Her Majesty's left!! Without demur he smoothly dropped to his knees at his Sovereign's Royal Command!!! The vast assemblage...

Husband, Drop to Thy Knees! Immediately! Ch. 01

by Ashesh9 on Mar 7, 2018
BDSM

"Husband drop to thy knees!! Immediately knave, dost thou comprehend???" her right hand shot out & expertly boxed the ears of the blond, blue eyed Greek God standing deferentially to Her Majesty's left!! Without demur he smoothly dropped to his knees at his Sovereign's Royal Command!! The vast assemblage watched the spectacle appreciatively: male phalli th...

Danni

by Coder3445 on Jan 6, 2020
Transgender & Crossdressers

This story is a complete work of fiction. In said work all characters are at least 18 years if age. This is my first story so constructive criticism is welcomed. Enjoy or not don't let me tell you what to do. *** Daniel had an issue, the issue being that when he had first started watching porn he like any other cis-gendered male had started with a voluptu...