Sissy Halloween Stories Stories

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Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

The Halloween Dangler

by weftandwarp on Sep 16, 2017
Romance

The Difficult Seduction of the Halloween Dangler, Snake Cracker, Bull Dropper and Pacifist Contender. * Christie was ready. Dressed in black with a tall conical hat and carrying a straw broom. She'd even had time to paint her face black. And her legs. And her arms. She'd been ready for a while, was extremely excited, and I was the slow poke. I didn't reall...

A Sissy Saga Ch. 18

by Snurge on Sep 15, 2017
Novels and Novellas

Miriam observed the assessor from the Historic Buildings Commission with a measure of disapproval. When he'd first arrived she'd believed her luck had changed and he was about to reverse a previous decision and tell her that financial help was about to arrive by way of a grant. That was not what had happened. "I was on my way to Chance Hall," rumbled Mr Cra...

I Fell in Love with a Ghost

by qhml1 on Sep 19, 2017
Romance

This is not a Halloween story. I just added the bit at the end in honor of the holiday. Hope you enjoy. ................................................ He just showed up one day, and the bar owner did everything but kiss his ass in front of everyone. He even set up a small table in the back near the restrooms, and no one was allowed to sit there except h...

Redeemers of the Fallen

by GayTripper on Oct 8, 2019
Erotic Horror

+++++ Redeemers of the Fallen +++++ The following is my entry for the 2019 Halloween Story Contest. This is of course the sequel to the First Place winner from the 2016 contest, Sisters of the Fallen. While not strictly necessary to enjoy this new tale, I highly encourage you to read "Sisters" first so the personalities, histories, and motivations of the pr...

Huntress of the Fallen

by GayTripper on Oct 6, 2020
Erotic Horror

+++++ Huntress of the Fallen +++++ The following tale is my entry in the 2020 Halloween Story Contest. It acts as both a sequel and the final act of a trilogy that began with the 2016 Halloween Contest First-Place Winner "Sisters of the Fallen" and continued in the 2019 Halloween Contest First-Place Winner "Redeemers of the Fallen". I hold no expectation of...

Questions That I Don't Have Answers

by SusanJillParker on Sep 16, 2017
Humor & Satire

SusanJillParker has lots of questions but no answers. Help. I need help. Being that there are lots of wicked smart and/or educated people who read the sexy stories posted on Literotica, I need your help. I need answers. I have lots of questions that I don't have the answers. In search of answers, I need answers. With all of these unanswered questions hurti...

'Ween Contest

by Nathan_Brazil on Sep 3, 2017
Erotic Horror

Greetings to everyone! Yes, this is my entry into the Halloween contest. It's sort of a Satire/Celebrity/Erotic Horror piece with some gay sex, group sex, oral, and even some implied fisting. Yes, something for almost everyone in the Literotica family! Oh yeah, there's some Fetish too. I hope everyone loves it and I get to sell the film rights! * "Oh look!...

How I went from Domme to Slut Ch. 08

by Ms_Allison on Jul 11, 2018
BDSM

I would like to thank mymantoy999 for his editing and insight in getting this story up on Lit. I value your take on the stories as well as your conversation! Thank you Sweetie! ***** It was safe to say my state of dress bled over from my private life to my work life. It wasn't that I was wearing slutty outfits at work or anything completely inappropriate b...

The Vacation from Hell Pt. 03

by JamesMiehoff on Dec 11, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...