Sissy Transformation Stories

14,811 results
Orientation
Length
Source
Infinite Scroll

How I Became Sissy Willow Ch. 02

by willow619 on Sep 12, 2017
Transsexuals & Crossdressers

"Now the preliminaries are over, and it's time for the entertainment part of our evening!" That was what Fern, my wife, said to me as I lay on the bed after I had been fucked by our newly mutual lover, Jason. I was dressed in pink panties, bra and slip, and a floral sundress. A blonde wig with long curls was on my head, completing the transformation. Fer...

Bottom Kim

by Master Jim on Sep 13, 2017
Transsexuals & Crossdressers

Kim was tied down and helpless. She was stretched out on her back on the bed, with her hands tied over her head to the headboard, and her legs secured with a spreader bar. She was blindfolded, and had a phallic ball gag in place in her mouth. The lights were low in the room, not that she could really tell: just a couple of scented candles. Kim herself had o...

The Proof is in The Pudding

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

When my girlfriend of two years mentioned she liked to watch female impersonators perform, I seized the opportunity to confess my lifelong addiction to cross-dressing. The expected reaction of disbelief was no surprise but her reply of, "Well, let me see you dressed," was although welcomed, a bit of a setback. I'd not planned the truth to be revealed at suc...

A good fuck

by sissygasm on Feb 10, 2016
BDSM

This story will contain : bdsm, fantasy and sifi elements, gay sex, sissifacation, transformations and various other kinky things. You have been warned. First a description of the world this story will take place in: In this world things are simple, there was a natural order to the way the world worked: real, strong, masculine men were at the top and then as...

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Discovering Mistress Sarah's World

by oneguy4fun on Sep 11, 2017
Transsexuals & Crossdressers

Chapter 1: Meeting Mistress Sarah Joe's heart pounded fiercely as he stood at the door to his Mistress's house. He did not expect to be so nervous at his first meeting with her. After all he had known her for over a year. Mistress Sarah had been gracious enough to allow him into her world. He was fortunate to fall under the control of such a beautiful domin...

Alex to Alexis Ch. 02

by TransPrincessMorgan on Sep 25, 2017
Transsexuals & Crossdressers

Again, thanks to Jack Murphy for being an amazing volunteer editor! Enjoy! Chapter II: Acceptance This didn't sound good. Led by his mother's hand, Alexis clattered to the darkened playroom, to open the door to find the room unusually bare. The piano was still there, the wardrobe was still there; no television, no chairs... A weird piece of furniture domin...

Intervention

by Angelscuck on Sep 13, 2017
Transsexuals & Crossdressers

My fiancée's girlfriends were becoming a little apprehensive about the changes Angel was exhibiting since we had started dating. They had noticed her attire had become much more suggestive, and her make up more severe. There were other changes too. She was now sporting a tattoo on her right shoulder, an angel/mermaid holding a heart with my name on it. Sh...

A Girl And Her Sissy

by TollWard on Sep 18, 2017
Transsexuals & Crossdressers

Life is good. Life is really, really good. As I write this I'm sipping on a very expensive wine and wearing a very expensive dress while sitting in my very expensive apartment. I no longer work, having not needed to earn my own income for little more than a year now. That probably leads you to wonder how I pay for all my nice things. Well while I enjoy my lu...

Lois Lane's Night Out

by exxxidor456 on Aug 13, 2017
Fan Fiction

As with all my stories, I welcome other authors to add chapters! Remember to like and bookmark your favorite chapters! Regular chapters with 5+ likes get a sequel, chapters with 10+ likes get two. End chapters get an epilogue with 10+ likes. Chapters with the most likes & bookmarks get updated first! All characters in this story are at least 18 years old...

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Pokemon Grunt

by Cantalope on Sep 25, 2018
Fan Fiction

Things had been rough lately. It wasn't all one thing, though plenty of them were enough to put you down in the dumps, it was the combination of all the things together. You were having a hard time keeping your life together and all this stupid world seemed to care about was pokemon and training to fight with them. What about goddamn health care huh!? Sure t...

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