Sissified Stories

213 results
Orientation
Length
Source
Infinite Scroll

Young Sissy Ch. 03

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

"Pleez...por favor...pretty pleez...fuck me..." I looked up at her with tears in my eyes, pleading to be penetrated. I didn't have to beg...nothing in the world would have stopped Lola from spraying her seed deep inside my ass...but I know it's what they wanted to hear. I regretted it immediately...well almost immediately...nothing can take away from the pur...

New Gurl in Town Pt. 02

by GavinIsaNuisance on Oct 5, 2020
Transgender & Crossdressers

This story and its contents is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and entirely unintentional. All persons depicted in a naked/sexual manner are 18 and up. Andy begins his sissy adventures as Bianca, but will he be able to woo his crush Riley, or will he be forced to be Carol's bitch forever? We...

Mistress Morgan's Sissy Husband

by corduroysissy on Dec 10, 2017
Transsexuals & Crossdressers

Morgan Ashley was a very pretty lady, not movie star glamorous mind you, but far prettier than anything her wimpy husband Robin would normally attract. Having just stepped out of the shower she was wearing a red mid-wale corduroy bathrobe and her long red hair was wrapped in a towel. She was seated in the living room armchair with a cigarette perched between...

Reach Out For The Sunrise Ch. 07

by SadieRose on Sep 12, 2017
Novels and Novellas

© BELLORA QUINN & SADIE ROSE BERMINGHAM 2010 More apologies for the delay, again... I know, I know! We edit too slowly but we're both in full time employment and it's hard sometimes to find the space to just sit down and work on (in)decent smut. There is a warning of consenting sexual violence with this chapter. If you don't like it, please don't read...

Ella Cucks Her Patient Ch. 05

by CuckFantasy69 on Jun 17, 2019
Group Sex

I highly recommend you read the previous chapters for the full erotic experience. *********************************************** My 4th week of chastity was complete as I arrived at Ella's apartment eager for release. As I was about to knock on the door Ella opened it and threw herself on me. She gave me a big hug saying "I've missed you so freaking much...

House Rules Ch. 09

by EROTICbearscribe on Jan 22, 2020
Transgender & Crossdressers

AUTHOR'S NOTE: This story contains characters and references to events in two previous stories I have written: Just Across The Hall and PIXIE: Sissy Stripper. It is not necessary to have read these two story chains. This chapter of House Rules could stand on its own for entertainment purposes. If, however you want context, please read the other two stories f...

Compromised

by HorribleHenry on Jul 6, 2020
Transgender & Crossdressers

STORY OUTLINE/SYNOPSIS On holiday in Jamaica Sandy Armstrong's eyes lingered too long on three feminine items in a display window. By biometric means he was singled out as a possible sissy or the like, and the information sold to an international organisation. Sandy receives a surprise visitor at his flat in London, a shemale, who seduces him and he eventu...

The Society Ch. 02

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

The French maid outfit was just a little loose. I was borrowing Corinna's dresses until I was fitted for my own uniforms and outfits. Actually Corinna and I were close to the same dress size yet our body types were different. I had a more feminine build with flared hips and hard round buttocks while Corinna's more muscular build created a deeper V shaped upp...

Dominating Ken Pt. 09-10

by oneguy4fun on Sep 26, 2017
BDSM

PART 9: THE POWER OF THREE Kimmee's (Ken's) heels clicked across the marble floor of the hotel lobby. He was in a hurry to go nowhere. He figured if he walked fast enough no one would notice the secret underneath the feminine facade. Mistress Kareena had done such a fabulous job at hiding his masculinity and highlighting his feminine qualities that someone...

A Merry Christmas Lock In

by Louise69 on Dec 25, 2017
Transsexuals & Crossdressers

Dear Reader, this is my penultimate submission, but one that I wrote a year ago. It's one of my favourites and is more of a gentle erotic story than some of my hardcore ones. I wanted it to titillate, but be suitable for a read next to your Christmas tree. I also wanted it to be filled with a little more hope than some of my recent output. Transgender or tra...