Sissification 101 Stories

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Finding Our Heaven Ch. 00: Prologue

by GoddessFrigga on Mar 7, 2018
Transsexuals & Crossdressers

Author's Note: This is a total and complete wish-fulfillment fantasy about what I wish would happen in my own life. If it's too sunshine and roses at the end, it's because given the chance I would create this sort of life for myself, and I'd want a "happily ever after." If you're looking for the usual femdom, sissification garbage, and a protagonist so stupi...

Step by Step Sissification Ch. 02

by satinmarabana on Sep 16, 2017
Transsexuals & Crossdressers

Over the years, I've been with a few different sissies who were in different stages of their exploration and this gave me the opportunity to participate with them and learn a lot. I've also spoken with a couple dozen sissies on literotica who shared their own fantasies and desires. This story is sort of a distillation of my favorite stuff. -- "Oh, well,...

My Sexual Fantasies

by Submissive Timmy on Sep 16, 2017
Letters & Transcripts

My Sexual Fantasies (OD Repost) I wrote this in November 2002 for my online journal on Open Diary. I'm posting this simply to have something posted. I do intend to actually write eventually. ***** I have a penis. Isn't that amazing? I also have two testicles. The flu had a stranglehold on them and killed my sex drive. But, I've since driven the flu off wi...

Forgotten Hero

by Lustful Majesty on Dec 31, 2020
Cheating Spouses

The world outside of this dungeon no longer exists to you. Your life out there has become foreign from the indeterminate number of weeks that you’ve been down here struggling to keep your wits. Deviant monsters who want nothing more than to abuse your prone body lurk down every hall, and there is a constant test of faithfulness to your wife who awaits your r...

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RRRing, Ring, Mistress Calling

by lushusboobs on Aug 30, 2017
How To

Part 1: Phone Domination Isn't For Losers As a phone sex Mistress, I hear a lot of excuses as to why people choose not to call ranging from "Why pay when I can get it for free?", "Phone sex is for losers", "I can't get turned on by it." to "I want the real thing, not a fantasy." They are entitled to their opinion, however, I think that many people are close...

Breeding Natalia

by sweetsatine on Jul 3, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** Nathaniel Geller had been a young, up-and-coming salesman at MedZ who'd shown great potential. In just a few years, he made his way from ambitious college graduate to savvy junior manager. Risky ventures that others were skeptical of luckily always seemed to turn out succes...

NaNoWriMo 2020: Chyoa Edition

by grimbous on Oct 31, 2020
Miscellaneous

November is fast approaching which means NaNoWriMo season will soon be upon us. For those that don't know about it NaNoWriMo (National Novel Writing Month) is a creative writing challenge whereby a writer tries to write a 50,000+ word novel in the month of November. Our challenge here will be a different one but in the same spirit of encouraging writing and...

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Sissy for Marcus

by jackjones123hip on Jun 5, 2018
Transsexuals & Crossdressers

Hey readers! This is my first story on this site. I hope you get as hot reading it as I did writing it. The first chapter is sort of setting the scene, but the action will come pretty soon. I'd love feedback in the comments! Xoxo *** Hi! I'm Jack. I'm 5'2 with pale white skin, a super slim body and a mop of dirty blond hair. At school I always thought I wa...

No Choice

by AZgirlMichelle on Sep 16, 2017
Transsexuals & Crossdressers

You act as if this is news to you. I'm surprised that you would even question the fact. This isn't a bedroom game. It never was. I have a plan and you WILL follow it. Choice? What choice? Whatever gave you the idea you had a choice? I told you that things would change if you wanted to live with me. I told you it was my way or the highway. And what did you s...

Flowers For Pansy

by AmberFemXD on Sep 16, 2017
Transsexuals & Crossdressers

Daffodils were Pansy's favorite. To this day she is still a silly little flower gurl wanting, waiting, craving for another man to bring a fresh bouquet. But today was not an ordinary day. With the vacuum grinding and sucking and growling the knock on the door was just slightly audible. The little sissy . . . excuse me, pansy (she just loved being called a pa...