Sissy Fantasy Stories

87,403 results
Orientation
Length
Source
Infinite Scroll

Breaking with Traditions

by Canadagander on Sep 17, 2017
Loving Wives

Copyright © 2005. All characters, events, and text in this story are purely fictional, and are created by and the sole property of the author. All rights reserved. - - - - - - - - - - - - - - - - - - - - - - - Writer's Note: It's time for Canadagander to make a public disclosure, to come out of the writer's den, so to speak. 'Gander is not a real person....

Cuckold Hypno Assignment

by DivinaTellsAll on Jan 1, 2019
BDSM

My name is Divina. I serve Goddess K. and Madam Vega. I am on a journey to become their perfect sissy girl, and a cuckold slave to Goddess K (who is my wife). The following is a true story of an assignment given to me by Madame Vega, and carried out with Goddess K. Assignment: Watch cuckold hypnosis video pornography, with my chastity cage locked and and...

One Step Too Far

by SatinDreamGirl on Sep 16, 2017
Fetish

The clock on the bedside table clicked loudly in the otherwise quiet room. A soft buzz of cicadas outside drifted in through the small gap in the raised window. The room seemed to glow with pink from the afternoon sun. The room hadn't changed much since Rachel had begun her fashion phase in high school. Her closet (and the closet of the guest room) were stu...

A Sissy Fantasy

by Sissy_Jeanette on Mar 30, 2020
Transgender & Crossdressers

My darkest fantasy has come true. I'm now a slave to a dominant couple. My ex-wife and her new boyfriend have taken me in, and in return I am dressed as a girl always and their maid and sex slave. Frilly panties, stockings and skirts, babydoll t-shirts, and a blonde wig are parts of my new uniform. Also I now wear a stainless steel chastity cage now encasing...

My Glorious Transformation Pt. 01

by switchhitter420 on Sep 18, 2017
Transsexuals & Crossdressers

My first stab at erotic literature, let me know what you think! Part one of a serialized fantasy journey into sissy faggotry. ***** About ten years ago, I ended a pretty serious, 1-year relationship with a woman I had met while working at a bar. She was this classic beauty: elegant, dirty-blonde hair, thin frame, striking facial features, an amazing ass an...

Sissy Training

by kendra13 on Feb 13, 2018
Fetish

I am a blue collar manager type and live a pretty work a day life during the day, but at night, I have a rather interesting sideline. I am a sissy trainer. You see, many sissies are married and end up coming out to their wives. To most couples, this just creates a fun little fantasy for play during sex, but for some, it becomes more. For these couples, at so...

Black On Black Cuckolding : Hell

by Samuelx on Apr 3, 2019
Group Sex

Officially, we don't exist. That's what conventional wisdom tells us. If you were to type the words "Black Cuckolds" on Google, all you'd get are references to the standard-issue Cuckolding, which typically involves a big Black guy fucking a White woman while her husband or boyfriend, also White, watches. Nothing wrong with that if that's what moves you. My...

Black Cuckolding Dreams

by Samuelx on Sep 11, 2017
Group Sex

Sometimes what you're looking for is closer than you think. Take my fiancé and I for example. My name is Stacey Walton and I'm a young Black woman living in Milton, Massachusetts. I studied business administration at Bay State College and earned my MBA at the University of Massachusetts at Amherst. Presently I work for a real estate company in Brighton. I me...

Life With Miss Ida Ch. 03

by Sheermistress on Nov 30, 2017
Transsexuals & Crossdressers

After Miss Ida had calmed down from her orgasm and I had licked and sucked as much of her cum from her pantyhose as possible, I asked her to remove them. "But they're not that bad to wear Georgia and I know you love the feel of them so much, they're fine like they are, they're only a little torn, I can keep them on." "No Miss, I insist," I say, "Besides, I...

Planet Pretty Sissy

by Hayleykim on Aug 18, 2017
Fetish

Louise ordered her kinky slave to stand naked in front of her. He was in his late forties, about eight years older than the pretty blonde, who had him like putty in her hands. "Welcome to your ultimate fantasy. We don't take passengers on this parallel planet. Is that perfectly understood?" said Louise. "Yes of course, Louise," he replied in a stuttering w...