Sissy Halloween Stories

12,071 results
Orientation
Length
Source
Infinite Scroll

Girls only costume party

by latexdoll on Oct 31, 2008
Science Fiction

"This Halloween we will be hosting the first ever "All Whores Eve." No one will be admitted to the party unless they come in their best sexy, slutty, costume. The cover is only $20 which gets you in the door, entered in the costume contest, and see a special live performance by pop sensation Gwen Stefani starting at 8 pm, and she has promised...

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Connie Goes to College Ch. 03

by cmorehead on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. In my last chapter, Jeff and I had just made love for the very first time and I w...

Stood Up Pt. 01

by LadyJae01 on Jan 21, 2020
Transgender & Crossdressers

I hate bars, especially being alone in one. So, I make the best of being stood up. I pretend like I meant to be here, all dressed up, in a slinky, off the shoulder red dress, by myself. I migrate from the bar to an open booth, so I can people watch more easily. As I walk, I have to tug my dress down my thighs as it tries to ride up. Nothing is ever quite lo...

Sissy Arlene's Soul Mate Ch. 02

by SissyArlene on Jul 10, 2019
Transgender & Crossdressers

Note to reader; This is part of the ongoing story of sissy Arlene. To get a full sense of this Saga, you need to read the 3 parts of "SIssy Wants Her Wife's Boyfriend," and then read "Sissy Arlene's Soul Mate." And now, "Sissy Arlene's Soul Mate chapter 2." ***** I awoke to the smell of coffee and bacon. My first thought was that my wife had slipped out...

Halloween Pool Party Pt. 06

by sissymissyct on Sep 14, 2017
Fetish

I was exhausted and slept until 5pm when I was awakened by a gentle kiss from Miss Annie. She took off my headphones and rocked my shoulder a bit. "Come on my sweet sleepy sissy, it's time to get you up and about. We have a fun evening planned for you baby girl". I rubbed the sleep from my eyes and saw Miss Annie's beautiful face looking down at me. "lets ge...

On Your Knees Ch. 05

by JinkiesFarie on Sep 16, 2017
BDSM

He grabbed his shaft as he sat in his office, shame burned in his cheeks. This was his place of work, but the thoughts of Nicole were so powerful, so overwhelming--he couldn't help himself. During his lunch period, he had locked himself in there instead of taking the usual route into the school's cafeteria. Nicole penetrated his thoughts. In his little fan...

Kasey's Confession Ch. 19

by KaseyLegs on Sep 13, 2017
Transsexuals & Crossdressers

I woke up very early in the morning, having fallen asleep in my bathtub. The water had turned ice cold, which along with the discomfort of having my head planted in the corner of the tiled wall, had jolted me into an early awakening. Tuesday was Lisa's funeral, and I had the day off for it. In the morning, after getting some more sleep back in my bed, I wou...

Transforming Brent Pt. 03

by sissymissyct on Oct 8, 2019
Fetish

Over the next few days I removed most of my male clothing from the house and donated it to Goodwill. I met Wendy as she got out of work each day and we went shopping. The first time was for regular clothing. Skirts, dresses and blouses, leggings and shoes and regular lady's sportswear. Thursday it was lingerie night. I ended up with multiple bras and camiso...

Nina Dresses me as a Girl

by Bakeboss on Sep 14, 2017
Transsexuals & Crossdressers

I cannot believe a whole year has passed but as I look at the calendar, I see Halloween is approaching and that is when it all started. The company my wife works for decided to have a costume party, well not the company, but my wife's boss decided. Nora was bugging me for costume ideas and I just told her I would wear any costume she decided on. You see that...

Laying Down Some Tracks

by nolfon1 on Sep 19, 2017
Transsexuals & Crossdressers

I never expected what was to come of me, and even now, I'm still shocked by what I did. My name is Shawn, and I was just out of college and had a really hard time finding a job. I spent four years studying to be a teacher, yet I only ended up working at a fast food place and playing guitar for a band. The story takes place in early November, but it really...