Sissy Cumdump Stories

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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...

Going Gurly Ch. 01: Cara's Clitty

by anna_subCD on Sep 16, 2017
Transsexuals & Crossdressers

My stories are all true recollections of events from my life, as accurately as I can remember them, with two exceptions: 1. The names of my partners have been changed for their privacy; and 2. I have omitted any references to safe sex, because reading about people fiddling about with condoms is not to my mind very sexy, and in stories you don't need to be...

World of Eroticia

by Nightflight406 on Apr 22, 2025

The World of Eroticia (Ee-rot-i-see-ah) is a beautiful place, full of tall mountains, green fields, sparkling oceans, and of course, quite a few attractive females. These lovely ladies hold a variety of positions, quest taking adventures, ruling queens, knowledgeable spellcasters, and ordinary civilians. While the fairer sex have the freedom to change their...

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Ultimate Sissy Weekend Ch. 06

by SissyTwinkleToes on Feb 4, 2020
Transgender & Crossdressers

Susie wonders if she'll ever get used to the horn honks. The gasps. The shouted comments. The whispers. The cruel laughter. She is stood with her sissy sister, Tinkerbell, in her pink OTT sissy dress she's been trapped in for over two days now, on the corner of the bad neighbourood where she now lives. It's 7:45, and she's been stood in public for almost two...

Tara has a Threesome

by SissyTara on Oct 13, 2017
Transsexuals & Crossdressers

I was lying in bed one morning. Dave stopped by on his way to work at the construction site down the street. I answered the door in purple bikini panties and a matching baby doll nightgown. We had fucked a few times since our first encounter when I had walked by the construction site. He stepped inside without asking and kissed me hard on the lips. I respond...

Going Gurly Ch. 02: Bondage Slut

by anna_subCD on Jan 5, 2018
Transsexuals & Crossdressers

My stories are all true recollections of events from my life, as accurately as I can remember them, with two exceptions: 1. The names of my partners have been changed for their privacy; and 2. I have omitted any references to safe sex, because reading about people fiddling about with condoms is not to my mind very sexy, and in stories you don't need to be...

Tara's Journey Continues

by SissyTara on Sep 16, 2017
Transsexuals & Crossdressers

After my experience with Raoul I had started to discover who I was. I was becoming more and more feminine. My long brown hair now had blonde highlights in it. I was wearing makeup regularly. And I dressed more and more femininely. I also decided I liked being the woman during sex and liked teasing boys. I went out for a walk one afternoon. I was wearing bl...

Jasmine - Sissy Slut Transformation Pt. 01

by BillyBaroo4you on Jun 1, 2020
Transgender & Crossdressers

A Sissy Cumslut Transformation Part I - The First Taste (of cum) Nervousness crept into his mind like a snake, slithering its way down toward his stomach. He felt scared, worried about the night ahead, worried about how this one night would change his young life forever. His gentle hands began to tremble as he applied the hot pink nail polish to his finger...

Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...

Groomed to Depravity Ch. 06

by ssamlee2000 on Sep 14, 2020
Transgender & Crossdressers

It was Mohamed's birthday today. In exchange for having "skipped on the job" on Saturday, I was to be the "entertainment" tonight for the party. I had my term exams this week, but I wasn't exactly in a position to say no. I'd already fallen so behind on the materials due to my weekend duties, I doubt one more night of studying would've helped me anyways. I...