Turned Sissy Stories

282,204 results
Orientation
Length
Source
Infinite Scroll

A Perverse Plan

by Candyboi on Sep 25, 2017
Transsexuals & Crossdressers

It started off with little things, small suggestions, that quickly snowballed into perversion. My wife Carla, who for the first decade of our marriage displayed little interest in kinky sex games became a hot wife virtually overnight with total control over me... Carla is 44, has a very curvaceous ass, 34DD tits, and works as a doctor at the local hospital....

Sissy Boy Secretary Ch. 03

by Hotenuf4u on Sep 19, 2017
Fetish

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you! After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in...

The Prostate Exam Pt. 04

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by not being able to resist pushing back against her finger, forcing her finger deeper into asshole. At that point his female doctor had decided to test just how submissive he was. She gave him the option to back out if he...

The Snow Sissy Ch. 01

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

Somewhere, in the frozen northern regions of our great globe, in the shivering mountains, there is a school of demon. Now, we all know what demons look like – they are creatures of immense, horrifying beauty. Even with their skin (which can range from Jet black, through fiery red, to the purest alabaster white) they possess inhuman and powerfully seductive b...

Sissy Crissi Ch. 03

by sissycrissi on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 3 -- Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upwa...

Sissy Boy Secretary Ch. 04

by Hotenuf4u on Sep 19, 2017
Fetish

Arriving at the office 15 minutes early, walking past three of the other secretaries, noticing them smiling and giggling when they glanced my way. Elaine must have told them of my secret desire to wear panties. Today's choice was the white lace thong pair, which felt good as they rubbed against me as I walked. Feeling my face turning red, I walked faster to...

Tales of Sub Asian Sissy Ch. 04

by subASIANsissyJADE on May 6, 2019
Transgender & Crossdressers

(Thanxxx so much for taking the time to read me stories! This is just my fourth post and I'd absolutely love any feedback... also, please feel free to reach out if you just wanna chat with a very depraved and submissive Asian sissy) ***** Dave threw my dress at me. "Hurry the fuck up, you stupid slut. My wife gets home in a couple of hours and I need to cl...

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...

Halloween Pool Party Pt. 06

by sissymissyct on Sep 14, 2017
Fetish

I was exhausted and slept until 5pm when I was awakened by a gentle kiss from Miss Annie. She took off my headphones and rocked my shoulder a bit. "Come on my sweet sleepy sissy, it's time to get you up and about. We have a fun evening planned for you baby girl". I rubbed the sleep from my eyes and saw Miss Annie's beautiful face looking down at me. "lets ge...

Ms. Alexandria - Interview No. 01

by gasissynora on Dec 3, 2019
Mature

I am sitting by myself in what appears to be a restaurant/bar that caters to women. I have been exchanging emails with Ms. Alexandria concerning a position she has open for a couple of weeks. She wanted to meet me here at "La Femme" to interview me about the position. I am sitting at a table in the back of the bar area waiting for Ms. Alexandria to arrive....