Sissy Halloween Stories

12,071 results
Orientation
Length
Source
Infinite Scroll

Trick or Treating a Witch

by nvioxos on Sep 1, 2017
Group Sex

In her usual indolent way, Eve crawled right on me. I could see her hips move left and right as she was getting closer. She kissed me knowing I loved the taste and smell of her cum-covered, puckered lips; this was our ritual after a blowjob. She was a woman who loved giving head and swallowing more than she loved anything else; you could say she lived to suc...

Kasey's Legs Ch. 08

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

For the rest of my day at work, after getting my face fucked by Ken, the president of Goodrich Logistics, in Mr. Jones' office, I kept to myself. The guys continued making remarks, gestures and references to the home movie I'd made. They'd all obviously seen the movie by that afternoon. I'd seen Steve in the break room with his laptop and other guys gather...

Emily's Girlfriend

by bluesbirds on Feb 26, 2019
Transgender & Crossdressers

Emily and I stepped out into the street, into the cool air, and looked at each other, exhausted. We had been finishing a major paper for school for almost the entire day, stuck inside the library. Emily had snuck in a bottle of wine and pulled it out as we were finishing the revisions, and soon we were flirting with each other, relieved from completing the a...

The Tales of Crissy the Sissy

by EPCene on Oct 5, 2020
Transgender & Crossdressers

Chapter 01 Halloween night 'Those guys are real fucking assholes,' Chris Masters thought as he walked alone down the crowded street. He had known most of them for the better part of a year and never thought they could do this to him. They had met at work. Chris was the new guy and was instantly brought in to meet the rest of the middle management team. Th...

Groomed to Depravity Ch. 03

by ssamlee2000 on May 11, 2020
Transgender & Crossdressers

Mohamed sent me a link to a voice training regime for trans girls and gave me three days time to learn how to talk "properly". He said he'd call me today for my test. I skipped class again and stayed home awaiting the call. If I didn't answer or failed the test, he threatened to "make me regret it" the next time we met. All day I practiced my voice for fear...

Catwoman Prowling

by cindy_4u on Sep 14, 2017
Erotic Couplings

2 years back for Haloween I was dressed slutty as usual. My costume for that year was Cat Woman. A tight body suit held with a clasp behind my neck, a zip on my ass to keep it tight around my waist and criss-cross strands that exposed my back and abs. Boots, mask, whip, the works. The tight body suit complemented my tiny frame to show every one that I had n...

Just Look at Me Now Ch. 04

by GFfan on Jul 15, 2020
Transgender & Crossdressers

Let's see... where was I at the end of chapter three? Oh yes: seated on a footrest wearing lingerie and my pink collar, with my eyes adjusting to the bright light now that my blindfold had been removed—and adjusting to the sight of Jude's strap-on in front of my face. "Have you ever given another guy head?" Jude asked. "No, never!" "How about getting a bl...

2016 Literotica Reader's Choice Awards Winners

by Literotica on Sep 16, 2017
BDSM

The stories and authors below were chosen by our readers as the best of 2016, in voting which took place here. Though these are not the only wonderful authors and stories on Literotica, they are worthy of praise and recognition. Thanks to all of the writers for providing us with hours of hot reading, and to all of the readers for your input, support, and a...

The Halloween Parade Transformation

by rutger5 on Oct 24, 2017
Transsexuals & Crossdressers

Story is for Lit Halloween contest and contains themes of non-consensual sex and reluctance. (An original story -- Copyright 2011) * It started over a bet but it ended in a most surprising way and totally changed my life. I was a sophomore attending NYU in the heart of New York City when it occurred. Originally I'd come from Ohio but by my second year of...

The Doll Maker

by Fibaro on Jan 22, 2020
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** (This story was one I wrote and posted on Halloween. It's a bit more gruesome than my other works as a result.) *** Intro Carl had always been different, he was a quiet somewhat effeminate looking boy, taking mainly after his mother. From an early age he had loved playi...