Sissy Fantasy Stories

87,403 results
Orientation
Length
Source
Infinite Scroll

BLACKEDmailed Into Being a Sissy

by AnonWriter on Jun 17, 2019
Fetish

Author's note: I've hit serious writer's block with Tales of Feminization, so I decided to try something a little slower and more limited in scope. I'll be focusing on one primary storyline at first, slowly branching out with other choices. You'll notice some chapters will have multiple choices, but this is just to act as a reminder for me for future content...

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The Male Fantasy

by TheKink on Feb 28, 2021
Fetish

This introduction will be short as I feel I have explained what this "book" will contain. However, if you are into aggressive and often times degrading sexual encounters that involve: Futa, sissy, straight, gay or bisexual characters.. then this story will hopefully be to your liking. • Stories will most often be in 2nd person. Please leave suggest...

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Sarah Gets to Write Her Own Story

by SarahCD on Jan 6, 2020
Transgender & Crossdressers

If you are an adult, looking for some kinky fun, live in the San Francisco peninsula and would like to star in a re-enactment of one of my experiences, contact me. My experiences here show what I like to do. We can write our own scenario and then act it out. I'd love to help you make your fantasy a reality. Now for my latest adventure, I found a Classified...

A Husband Named Cathy

by cathynylons on Sep 25, 2017
Transsexuals & Crossdressers

When my wife Jane first found out about my naughty little secret she flew into a rage and launched into a tirade calling me a lying, duplicitous, deviant, degenerate pervert sissy faggot. She stormed out of the house slamming the door behind her. About an hour later she returned and had calmed down. In a very apologetic tone she said that she was sorry and...

Pimped Out Sissy Bitch

by Gemsissy on Jan 12, 2018
Fetish

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit. I glanced at the phone....

Sissy Crissi Ch. 01

by sissycrissi on Sep 11, 2017
Transsexuals & Crossdressers

Chapter 1 -- One Dreamy Night Like most Friday nights, my roommate Erika would be gone tonight. She and her new boyfriend, Leroy, were taking off for a private weekend. Erika and I had met about two years prior, when we were introduced by a mutual friend. Being fresh off a divorce, I was in need of a place to stay, and Erika was in need of someone to help w...

Erin Ch. 15: Perfect Sissy Cuckold

by Graves94 on Nov 16, 2020
Fetish

Erin Ch. 15: A Perfect Sissy Cuckold By Jonathan Quincy Graves {Note: This is the fifteenth in a multi-part story series cataloging the progressive evolution of a relationship between a dominant woman who provides leadership and discipline for her husband. Each installment can stand alone, but they read much better if you start at the beginning. Go to: Eri...

Finally Found Her Ch. 02

by hyperpress on Aug 18, 2017
Fetish

Switching from "you" to "she" for effect. She moved from the vanity chair to the bed. I've covered the bed with pillows and the room is lit with candles. "You're such a good little girl, now go get us a bottle of wine," she is lovely on the bed. I'm standing at the bedside and your mouth is irresistible and I bend at the waste to kiss you. Softly we kiss a...

Tales of Sub Asian Sissy Ch. 01

by subASIANsissyJADE on Apr 3, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** (I'm new here and this is my first post! I'd soooooo love to hear any feedback, questions, or comments! Many thanks, xxx, Jade) ***** I wore exactly what he demanded - he told me to dress like a regular girl... he told me he had nosy neighbors and, being a married man, he...

The Unsuspecting Candidate Ch. 02

by missvicky53 on Sep 11, 2017
Fetish

Part 2 Helen continues Mike's training, this time in a French Maid's uniform The aftershocks of his climax were still coursing through his body as I teased him. "Did you have a nice cum, sissy?" I cooed at his still bound form. "Do you want me to release you now?" "Yes, please," he replied. "I'd like to get dressed now." "And get dressed you shall," I tea...