Trans On Sissy Stories

357,668 results
Orientation
Length
Source
Infinite Scroll

Recruiting of a Sissy Maid Ch. 10

by Sissy_Chantel on Nov 23, 2017
Transsexuals & Crossdressers

Chapter Ten: Changes Continue for Chantel as Her Relationship with Carl Grows. Awake and having a great breakfast superbly made by Carl, Chantel enjoys her morning with him. He has her in one of his robes as they talk about things and their future together. After breakfast Carl says, "Put on a pair of my jeans with your white satin blouse, you can wear yo...

Jasmine - Sissy Slut Transformation Pt. 02

by BillyBaroo4you on Aug 31, 2020
Transgender & Crossdressers

A Sissy Boy Transformation (Continuation of Part I) Part II - A "Real Sissy Girl" Now Jazzy looked down at the table than in the mirror, then slowly began to apply her makeup, heavy amounts of it to get that bimbo presentation that Mistress wanted so bad. Sparkling hot pink lip gloss, she was wet by the thought of it. Pressing it to her lips, the butterfli...

Did that Really Just Happen?

by AnnaV on Dec 2, 2019
Transgender & Crossdressers

I'd been out with one of my best friends. We'd had a few drinks and ended up in this little bar with some cracking looking women. There was one woman in particular who we both fancied. She was very pretty, but not especially my type as she barely had any tits. Nice enough and eventually she went off with my mate, leaving me alone in the bar. It was too earl...

The Vixen

by TheEroticProspero on Oct 11, 2017
Transsexuals & Crossdressers

Simon first saw her as he walked through one of the rougher streets in town. He couldn't help but stare at her long red hair, sharp facial features, milky white skin and the tight velvet jacket she wore over an even tighter leather dress. He looked her up and down, admiring her modest but perky bust, her thin but shapely body and her simply perfect legs. Si...

Uncovering the Sissy Beneath Pt. 03

by jefferyscott745 on Jun 25, 2019
Transgender & Crossdressers

Disclaimer: This story contains extreme fetishes including BDSM and forced seduction. It is also purely fictional. This is part three of my previous work. Be sure to read parts one and two if you wish to understand the background of this section. *** I hesitate to follow him out of the bedroom, as my anxiety is out of control. "Have I just been kidnapped...

Being Mindy Ch. 03

by mindyrose on Sep 15, 2017
Transsexuals & Crossdressers

I started going to the gym regularly and it gym proved to be not only good for my body, which was down to 120 pounds and my skin was softer than ever, but also my sex life. The bar was always full of available guys, both customers and staff, who always made me feel feminine and horny. It didn't hurt my popularity at the bar being a slut that was always willi...

Mary Becomes a Whore

by Juggerhead on Jul 30, 2019
Transgender & Crossdressers

Mark was like any other ordinary 25 year old guy with a regular 9-5 job as an office executive in an finance company. He was fair, around 5 feet five inch tall and had a slender frame. Often his friends and colleagues would ridicule him for his height and thing body. He had a boring life and didn't indulge in partying or clubbing. After his divorce he went o...

Panty Posers Ch. 03

by EROTICbearscribe on Sep 14, 2020
Transgender & Crossdressers

It was early on Sunday morning. I awoke needing to pee and slipped out of bed, doing my best not to wake Daphne. I could hear him breathing deeply next to me most of the covers on his side as usual. My roomie was lying on his stomach, his head under his pillow. He looked so sexy lying there. I felt the warm rays of the sun on my back as I breathed in his cu...

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

Gothic Sissy Snowbunny

by Satanicsissybitch on Mar 2, 2020
Transgender & Crossdressers

Don't ask me why but I've recently decided to come clean. To the world, my readers, my friends and most importantly, to myself. I can't hide or pretend anymore and I've decided to just put it all out there for the world to see and, believe me, it's extremely difficult for me to tell the story I am about to tell you. First, I think it's probably important t...