Sissy Halloween Stories

12,071 results
Orientation
Length
Source
Infinite Scroll

Broken on My Break

by TopSeeker on Sep 19, 2017
Transsexuals & Crossdressers

**Disclaimer, all people places and events in this story are completely fictional and made up by me. This story contains the following elements: non-consent, dominant shemales, spiked drinks, shemales/transgenders being the penetrative partner to males, many terms used which are derogatory both in general and specifically to trans-gendered individuals. Pleas...

Adam's Journey Pt. 28

by stormdog on Sep 15, 2017
Loving Wives

My orgasm had been so sudden and intense that it had even surprised me, and I was left gasping and shaken, my cock still deeply buried, motionless, inside of Sue's now liquid pussy. We laid that way for a minute, all three of us silent and unmoving, and when I could speak, for some reason the first thing I said was "Holy fuck! Rick, I just came in your wife!...

Indian Wife & Boss Ch. 03

by tantrik721 on Sep 25, 2017
BDSM

Meena was lying on her bed thinking about the recent events in her life. She was wondering what had happened to her, why she gets so easily seduced by other men. The fucking with guards could have been easily avoided if she had acted tough, but instead she was excited and horny by the touch of other men. She keeps reminding herself that she was blackmailed b...

Indian Wife & Boss Ch. 04

by tantrik721 on Sep 25, 2017
BDSM

Ravi felt guilty as he blamed himself for everything. Meena showed no pity on him rather creates situations where he feels even more remorseful. He was more caring, more loving towards Meena. He took care of most of the household chores and stopped bugging her for being late from office. Meena was enjoying this new found freedom. Kripa called her the next...

Changeling Ch. 01

by Michael142 on Sep 19, 2017
Fetish

Changeling Ch. 01 How I feminized my husband. Michael142 Note to readers: This is a story in four chapters; they are all completed, and I will post them in quick succession to avoid long waits for anyone interested in following them. It is is a story that touches on many categories of this site, including a loving Wife, trans-gender/cross-dresser, some ro...

Husband's Fantasy Backfires Pt. 08

by xleglover on Sep 26, 2017
Loving Wives

Chapter 15 The sun was rising as Darius pulled into the drive way of Jen's house. He looked over at Jen. She'd fallen asleep on the drive from his apartment. She looked a mess. Hair tousled, patches of dried juices on her face (his and Christy's), hickeys on her neck. She'd managed to put on her blouse and skirt before leaving his apartment, but the blouse...

Magic Words

by wetapap on Sep 16, 2017
Romance

********** There is no explicit sex in this story. I wish to thank the people who helped contribute to and edit this story, per their wishes, they remain anonymous. This story is totally fictitious; any resemblance the characters might have to persons living or deceased is purely coincidental. No part of this story may be published at any other site without...

A Vegetarian Virgin

by Bedu on Sep 14, 2017
Mature

Have you ever met a 27 year old woman who was a virgin? More intriguingly, imagine that this 27 year old virgin was shapely, very pretty, college educated and sophisticated in a northeastern pseudo-intellectual, ultra-liberal, politically correct kind of way. If that wasn't enough, she was also a vegetarian, of the most extreme variety. Imagine then that th...

Hazardous Waste Ch. 05

by NOIRTRASH on Sep 16, 2017
Loving Wives

All characters are adults. Reminder. This tale is noire, and noire is neither kind nor gentle nor uplifting. It's supposed to stun and sting and offend. ***** I got sick as shit one night so they tied my sixty-five year old ass up in a straight jacket and hockey mask, like I was Hannibal fucking Lector, and led me off to the infirmary with an armed escort...

What the Hell's Happening Ch. 08-09

by next2ArchStanton on Sep 19, 2017
Erotic Couplings

Are you still with us... Probably not... Perhaps you'd just like to skip forward to chapter 14 and find out What the hell's happening. Anyway here's chapters 8 & 9. Cheers, Arch. PS. Excuse the editing, still struggling with it on my own... for obvious reasons. ***** 8. IT SEEMED LIKE A GOOD IDEA... I knocked on the door with breakfast. "Uhh... come in!...