Sissified Stories

213 results
Orientation
Length
Source
Infinite Scroll

Money Shot Pt. 02

by GavinIsaNuisance on Jul 27, 2020
Transgender & Crossdressers

This story is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and completely unintentional. All persons depicted in a naked/sexual nature are 18 and up. Tanya introduces a newly sissified Danny into the world of erotic photography which gets them into a hot offer they can't refuse. Author's Note: So, I establ...

Wife in Control Ch. 07

by wifetoy on Sep 25, 2017
Fetish

This is the seventh chapter of my wife's fulfillment of the punishment poem I submitted suggesting ways to atone for my inability to control my orgasm. Please read the earlier chapters for the full poem and the humiliations I have been forced to endure because of my failure. I am grateful that my wife loves me enough to exercise the total control over me tha...

Robin and Jimmy Olsen - Sissies Ch. 06

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

"Miss Robin! Surely you can't be serious!" "Introduce us, Alfred! Just like any other guest arriving, we deserve to be introduced to the crowd!" demanded the lovely sissy! Robin and Jamie were dressed in very attractive summer dresses - Robin in blue and Jamie in green which accentuated his green eyes and emphasized his bright red hair! The dresses would ha...

My Father, The Maid

by SissyOona on Oct 16, 2018
Transgender & Crossdressers

I thought it was really weird when I received the random text from my step mother, even though I had known her for most of my adult life as my father's new wife we had never really been close. Hell, for that matter I had never really been close to my father either, he was always pulling long hours at the office when I was young, so he was never around. Nowad...

Flames of Necessity Pt. 09

by Sputnik57 on Aug 28, 2018
BDSM

Sheppard's cock boned rigid at being in the company of women he'd masturbated over, their debauched attitudes and righteous pomposity, even more surreal that it had been at a distance, now he was immersed fully within their atmosphere... and their captive. He stumbled humiliatingly on all fours as the delighted Ruby expressed her triumph over him with swift...

Two Nemos at The Falls

by XXscribbler on Dec 23, 2017
Erotic Couplings

Jesse was alone, and the restaurant not at all crowded. The couple arrived just as the waitress finished taking his order. They entered from behind him, almost brushed his arm enroute to their table some 20 feet away. The restaurant was laid out oddly: the new couple's table was oriented at about 45 degrees to Jesse's line of sight, making her fully visibl...

Illicit Desires

by MistressRogueSpider on Apr 20, 2020
Transgender & Crossdressers

It was a hotel room like any other hotel, located in the cheap district. $28.99 a night could get you four walls, a "clean" bed, and a small bathroom with a tub/shower combo. The size was about the size of a studio apartment or a really small living room. Paper-thin walls meant privacy was low; you could guarantee the neighbors could hear so much as a whispe...

Celeste Pharma Ch. 02

by HorribleHenry on Oct 19, 2020
Transgender & Crossdressers

CELESTE PHARMA CHAPTER TWO I spent a very bad night ruing the day and the hour I had met up with Damian and had found my way to Celeste Pharma's Research Centre in the town of Crabtree. In just the first day of the course I had been virtually stripped of my masculinity with the aid of a black demoness called Monika. According to her I had been rendered pe...

Walk-In Clinic

by ColinGraham on Sep 26, 2017
Transsexuals & Crossdressers

I don't know why I forgot to wear men's briefs that day, perhaps I was just so used to the comfortable feel of silk and lace that I didn't even think about it when I dressed. Or maybe I had an unconscious desire to be caught; to finally have my little secret uncovered. So here I sat at the walk-in clinic, debating whether to leave, or to risk the off chanc...

Flames of Necessity Pt. 02

by Sputnik57 on Feb 13, 2018
BDSM

Horace had awoken erect, his mind flooded with the teasing expectancy of the severities of submission he'd face while there, Gerda's expensive scent having a command and authority all of its own as he sniffed in the semi-darkness. His erection was maintained as he was dressed by two sultry but vigorously authoritative women, who took a perverse pleasure in b...