Sissified Stories

213 results
Orientation
Length
Source
Infinite Scroll

Robin and Jimmy Olsen - Sissies Ch. 04

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

The Date Continues (finally) ***** Just as Ollie and John began to wonder what was keeping their dates, they spotted the delectable pair of sissies returning from the rest room. When they reached the table, both men stood. Their politeness was rewarded by a brief kisses from the pretty lads. Each girlyboy also managed to run her hands across the crotch of...

Lucian Ch. 10

by angiquesophie on Sep 14, 2017
Transsexuals & Crossdressers

How to win a fight if all you know is to be charming, sweet and graceful? The room was large and stately. It was a drawing room, really, with paneled walls and high, shuttered windows. The scent of polishing wax reminded Lucian of Bobs working hard to clean it. Maybe the place served as a conference room; or even a boardroom with its huge, shining table...

Mistress Kate Pt. 01

by corduroysissy on Feb 7, 2018
Transsexuals & Crossdressers

L. Jordan Bains wasn't sure of what to expect when he stepped into the large wood paneled office, but he knew whatever it was it wouldn't be good. He was in a lot of trouble, the Leprechaun wasn't known for having a forgiving nature. Jordan had never seen him, he only knew him by reputation, when you hung around the poker tables of Waller City you heard all...

Dr. Hottie's Story

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

Stuck in my office again. Tired, stressed, hungry, a little bored...I hate admin. Working as a doctor has its rewards. But the long hours and endless paper-work are not one of them. Hubby, though he's patient and understanding, is getting increasingly frustrated. It's affecting our intimacy - especially our sex life which is now frequently no more than once...

You Can Always Say No Ch. 02

by AngelCherysse on Sep 25, 2017
Transsexuals & Crossdressers

We had had 'The Talk' in the afterglow of that first evening of sex in our newly-revised relationship, less than a month before we exchanged vows. There is nothing more abjectly terrifying – for either person – than laying bare your soul at such an intimate level. He admitted his wants, needs, and desires; I reciprocated. He did, indeed, have a 'sissy' strea...

Hausfrau

by Vera_Garden on Sep 16, 2017
Transsexuals & Crossdressers

The night they came back from Octoberfest, she burnt all his clothes. Gerrig and Margarethe agreed a week before that they'd both wear traditional dresses to the famous German beer festival in Munich. "Gerrig, I only have one dirndl. Why don't you wear your lederhosen you wore last year? The way your thighs and butt look in the tight leather, it gives me id...

Wet Dream Pt. 03

by sissymissyct on Jan 28, 2020
Fetish

Gayle finished ordering items on line and checked the cam to be sure Georgia was asleep. The wetness in her panties told her what she needed to do. The payback for all those years that bastard cheated on her and how he had no idea what was coming to him, just made her pussy so wet. She was soon in bed enjoying her favorite toy. "I can't believe I slept so l...

A California Stop Pt. 03-05

by needyone16 on Jun 9, 2020
Fetish

Intro: One should read Part 1 &2 to get the whole gist of this story; however, if you didn't here's the nickel version. Richard and Jessica had been involved with a mutual friend, Abigail, who would orchestrate all their trysts. Without warning, things came to an end as Abigail left for the Pacific Northwest. Richard and Jessica were stunned. This is th...

New Gurl in Town Pt. 01

by GavinIsaNuisance on Jul 6, 2020
Transgender & Crossdressers

This work is entirely fictitious. Any similarities to actual persons living or dead is purely coincidental and entirely unintentional. All characters portrayed in a naked/sexual nature are 18 and up. *** The city of Los Angeles, California. A place once regarded as the focal point for entertainment and movie stardom now reduced to an over-taxed, grimy, dru...

slave stacie's Journey Ch. 01

by SirCarl on Sep 17, 2017
BDSM

This story chronicles the adventures of slave stacie, which is a sub story of the larger narrative of SirCarl and His "littleone." This series is about stacie, a new slave; she will have much to learn before Sir renames her thereby making her part of His ever-growing family. All participants are over the age of 30 (even a true Dominant knows never to reveal...