Sissy Halloween Stories

12,071 results
Orientation
Length
Source
Infinite Scroll

My Wife, My Tormentor

by Sissyjackie2008 on Sep 16, 2017
Transsexuals & Crossdressers

I am excited by the . One of the most humiliating experiences I sufferer was caused by my first wife. I had been a crossdresser since I was little. Actually my mother started me when she dressed me as a girl for Halloween. When at 7 I started to protest, She said she had no daughter and once a year I could let her have fun. I could never refuse her so I re...

House-Sitting Panty Lover Pt. 01

by sissydn on Sep 15, 2017
Transsexuals & Crossdressers

Finally Friday! The day I have been waiting for, for so long. A month ago my sweet and hot neighbours, Megan and Sophie, knocked on my door and asked if I would watch their house and feed their dog when they left for an extended weekend. I immediately replied yes and suggested I could do some house chores since I had no plans that weekend and were low on m...

Straight Crossdresser

by silkstockingslover on Oct 22, 2019
Transgender & Crossdressers

Summary: Guy dresses as a girl on Halloween and ends up performing as one. Note: This is a Halloween 2019 Contest story, so please vote. Thanks to: Tex Beethoven, and Robert for editing. * As I draped the sheer pantyhose onto my legs to finish off my Halloween costume, preparing for a night of cock sucking and bottoming at the annual Halloween men's onl...

Just Look at Me Now Ch. 05

by GFfan on Sep 14, 2020
Transgender & Crossdressers

ACT ONE: PARTY PREP "If the item is defective, you can return it for a full refund, but no, you cannot return it if it's simply too big. I'm sure you can understand why." This was the saleswoman's reply to the question I had been instructed to ask about an item Jude and Becky had assigned me to buy. "I doubt that will be a problem though," the clerk, Felic...

Textual Relations

by Pattyssissybitch on Sep 17, 2017
BDSM

PART I -- FRIDAY NIGHT My wife Patty had to go to Los Angeles for a weekend company annual retreat. When I dropped her off at the airport on Friday morning, she told me she had a surprise for me, and left it at that. I wondered all day what she was up to, and I had to wait until almost 4 in the afternoon to hear from her. When she called to tell me she'd ar...

'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!...

In For a Penny...

by TheHellWasIThinking on Sep 15, 2017
Fetish

To the reader: After I'd finished this story, I didn't know where to put it. It contains elements of several Lit categories, and I probably could have put it in any one of them. In the end, I decided to put it in Fetish, although it's very much a Loving Wives tale, as you'll soon see. NOTE: Every word of this is true. (Except for "Every word of this is true...

Kasey's Confession Ch. 23

by KaseyLegs on Sep 25, 2017
Transsexuals & Crossdressers

After Erica left me alone at the food court I sat quietly and nibbled daintily at my sandwich. I stared blankly at nothing in particular, but was jolted back to reality when Derek leaped out from somewhere inside the gate surrounding the food court's fountain and landed on the chair Erica had so recently occupied. "Riddle me this?" Derek asked. "What?" "R...

Kasey's Confession Ch. 09

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

I sat quietly in Mr. Smith's car on the ride home from our shopping trip. The events at the shoe store weighed heavily on my mind. The realization that I had just sucked off seven men in a storeroom was making me feel sick to my stomach. What made me even more nauseous was the fact that I had enjoyed it. "You are quite the prize," Mr. Smith told me as he dr...

Touch of a Hand

by Sabledrake on Sep 17, 2017
First Time

Here she was, naked in the dark. Cool but not cold. Her breathing shallow, her body motionless. Hearing distant sounds, and waiting. Eyes staring into the lightless black. Skin tingling. Anticipating the touch. The touch of a hand. ** As soon as he saw the girls running the ticket booth, Jeffrey decided that maybe this wouldn't be such a bad way...