Sissy Halloween Stories

12,071 results
Orientation
Length
Source
Infinite Scroll

I Love You Because

by _Lynn_ on Sep 11, 2017
Non-Erotic

Note from Jake Rivers This is my sixth semi-annual "invitational". The initial one was based on the Statler Brother's song, "Bed of Rose's". The second used the Marty Robbins El Paso trilogy: "El Paso", "El Paso City", and "Faleena". The third had stories based on the various versions of "Maggie May" or "Maggie Mae". The fourth invitational was based on any...

Weekend Slaveboy

by MsCarol on Nov 26, 2017
BDSM

As Kevin was driving home from work on Thursday he got a text message from his Mistress reminding him that this weekend was going to be a celebration of his six month anniversary as her weekend slave. And that she planned to raise the stakes of what he would have to endure if he wished to continue serving her. While continuing his drive home to his apartmen...

The Sibling Diaries Ch. 03

by Intimate Confessions on Sep 11, 2017
Chain Stories

Full chain & introduction can be found at this link. UNITED AIRLINES FLIGHT 2069 FROM DENVER TO SAN FRANCISCO Now here it is four years later and Gretta has moved in with me. She’s been here for a few months and she’s started to settle in. I find it ironic that I’m sitting in coach on a flight returning to San Francisco as I take this story up. After a...

A Happy Trouple

by Dennis_Kiros on Sep 14, 2017
Fetish

You should probably skip this story, if you don't like to read about men engaging in sexual activities with other men. ***** 1 Breaking up is never easy, but sometimes it's inevitable and absolutely necessary. I wasn't happy when Brit and I broke up, but I think both of us were relieved that our one-year-long relationship had finally come to an end. We w...

Trojan Whores

by Wholemanz on Sep 19, 2017
Transsexuals & Crossdressers

Proofed by Maggie Finson DECLARATION: This story is an original literary work. I wrote a story just to stretch my creative muscles. All characters, Sirens, and rapists in this work are fictional. Any resemblance to anyone living, dead, or born in the future, is purely coincidental. WARNINGS: Contains transgender themes, Sci-Fi, explicit sex, mild violence,...

Letting Go

by Iread2relax on Sep 12, 2017
Romance

Hi everyone. This is a story that I worked on towards the end of my break. I just had a chance to polish it up and post it. I'm placing it under romance. I hope you enjoy. I want to thank Andi for checking behind me. Any errors found are not because of this wonderful person. I'm not perfect so I'm sure you will spot a few mistakes. Please don't let them ru...

Not Drunk - Plastered

by Tomsparty on Sep 15, 2017
Transsexuals & Crossdressers

I was to marry on Saturday week and didn't want a stag night. The very idea of getting blindingly drunk with a loud, raucous bunch of mates unpalatable. I told my best man it wasn't required and to say nothing to my fiancé, Lily. Over the years I made many girlfriends and still secretly saw them on a platonic basis. I preferred their company to guys. One ni...

Red Wine On Her Yellow Dress

by Winterfrog on Sep 17, 2017
Loving Wives

Many thanks to snowbear for the editing of this story. * ROBIN'S STORY It was a bad day. It really was a very bad day for me, indeed. I had lost my job and I had lost my apartment. Though none of these matters were my fault, they happened with the worst possible timing. Only one week ago my girlfriend of one and a half years and I had agreed that we wer...

Daddies New Girlfriend Ch. 02

by LilLindaMelons on Oct 8, 2019
Transgender & Crossdressers

Part 2 AKA A walk in the park After the torrid love making session he had enjoyed with his Father just over a week ago, Jerry knew his life would never be the same. That night Doug had tenderly held his special Gurl against his chest and had warned his son that if he ever caught him dressed up as Cynthia again he would not be able to control himself becau...

Guarded Ep. 03

by GCStargazer on Dec 23, 2019
NonHuman

Leo strode over to the check-in desk of the hotel lobby. He was still in his leather pants, his jacket open and plainly exposing his sculpted muscles for all to see. The front desk girl gave a polite bow to him not seeming the slightest bit surprised by the display. "Good evening Mr. Montone, your room is ready for you already. The penthouse suite on the top...