Sissy Transformation Stories

14,811 results
Orientation
Length
Source
Infinite Scroll

The Sissy Models

by neverless on Mar 12, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** "It's not something I've ever done," Daddy said, with a frown though the fact he hadn't laughed it out of hand meant I knew I had a good chance of persuading him. "There's a first time for everything," I answered. "What if someone recognises us, Ricki?" he asked. "They won't"...

From Son to Sissy

by sinnyginny on Jul 27, 2020
Transgender & Crossdressers

A little backstory to this, alot of this story is based on one of my friends and what their journey was like as they were coming to understand their true sexuality, and a lot of it is their fantasy. All characters in this story are 18 years of age or older. I had always known i was different from all my other friends. It was when i turned 18 that i had rea...

Miss Annabelle Ch. 02

by Timewarp10 on Oct 16, 2018
BDSM

As Annabelle's first term at University drew to a close, I had become her slave: cleaning floors, laundry, ironing, cleaning her shoes, making her bed, sorting her clothes and other household chores. Each day was filled nonstop with toil, from early morning to late night, stopping only when she had gone to bed to sleep, and even then I would have to be alert...

The Computerized Bed

by submissive~pet~ on Sep 14, 2017
Fetish

The year is 2020 all sorts of new inventions have been created. The time machine in which John Paul traveled was from the year 2002. He had no idea what was in store upon his arrival to the future. His machine carried him into a large bedroom. It was a very lovely room done in pinks and light blues. The bed was enormous in size, 4 times the size of any he...

End Scene

by felicia_rene on Sep 28, 2020
Transgender & Crossdressers

This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy Description: When a rich wife discovers that her husband married her for her money and to add insult he turned out to be gay. ROLL CAMERA My rich wife had me over a barrel after finding out about my affair with my handsome boy toy assistant. She took a...

Mommy Adriana and the Video Booth

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

Dear Readers, I never imagined to get so far but funnily the more I write the more ideas I get. I hope you still enjoy the ride. * I closed my eyes. Not wanting to see people staring at the bound and gagged bundle which I had no doubt they were, especially when we stopped at red lights. In fact I didn't see where we were going. The only thing I...

Zoey's Basement Transformation Pt. 02

by SissyStoryTime on Sep 11, 2017
Transsexuals & Crossdressers

"Stand up," the whip crack of Mia's voice caused Zoey to flinch, but she didn't move from where she kneeled. With a sigh, Mia grabbed the leash attached to her chastity cage and started to give it a firm pull. Zoey quickly found her motivation, legs scrambling beneath her to find purchase. In her haste she slipped, almost falling back down. "Slower," Mia sa...

High School Dilemma Ch. 04

by LaurenWestley on Sep 15, 2017
Fetish

(Authoress's note: of course all disclaimers are still in place regarding characters etc. This particular episode is very XXX with pee scenes etc. However, I do know many parts of my stories will not appeal to all of you. I only wish there is enough to make each of you happy. To those who have given me constructive criticisms as well as those with praise tha...

Pay for Pleasure - Prequel

by Pleasure_the_slut on Sep 16, 2017
Transsexuals & Crossdressers

I had written about how Sandy turned me into a $50 whore before writing about how I got to that point with her. I was cruising an online posting for sex one Thursday evening and I came across a posting for TV looking for big cock. Well that got my attention, I'm 8" and very thick. So, I shot a reply right away. Not a minute later Sandy and I started chatti...

Zoey's Basement Transformation Pt. 03

by SissyStoryTime on Sep 11, 2017
Transsexuals & Crossdressers

Zoey couldn't believe the cruelty of her Mistress. She shook her head desperately, feeling exhausted and sore everywhere from the waist down from already having so many awful things done to her. She didn't know if she could survive this fresh hell. Mia moved away from the tied girl, her helpless form bent over and restrained at waist height. "Aww, what's t...