Sissy Clitty Stories

9,676 results
Orientation
Length
Source
Infinite Scroll

A Sissy Fantasy

by Sissy_Jeanette on Mar 30, 2020
Transgender & Crossdressers

My darkest fantasy has come true. I'm now a slave to a dominant couple. My ex-wife and her new boyfriend have taken me in, and in return I am dressed as a girl always and their maid and sex slave. Frilly panties, stockings and skirts, babydoll t-shirts, and a blonde wig are parts of my new uniform. Also I now wear a stainless steel chastity cage now encasing...

Sissy Maid to Be... Ch. 02

by missjennymaid on Sep 10, 2018
Transsexuals & Crossdressers

I would recommend reading Chapter 1 to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jeremy is get...

Discovering Amber Ch. 06

by Ms_Allison on Feb 12, 2019
Transgender & Crossdressers

Mistress notes: Once you understand them sissies are rather easy to manipulate and control. It's just a matter of finding which buttons are the ones that need to be pressed and when to press them. amber has a weakness for lingerie, heels, and humiliation. Additionally, she was very easily brought to her knees at the promise of an orgasm. Getting dressed up...

Smoking Blues

by sissymissyct on Mar 26, 2019
BDSM

"Hey Bren," called my assistant Sarah. The home office called while you were out smoking. You Better call Mr. C back. He didn't sound happy!" "Okay, thanks dear. I will call him back straight away," I replied as I headed to my office. As I was opening my door Sarah continued. "You know, you really have been taking a lot of smoke breaks lately. We are all co...

Sissy Training Vol. 01

by depositdutchess on Nov 27, 2017
Fetish

Being feminine is taught. Correcting your nasty masculine behavior with feminine manners and class is what you need. Being a sissy is your new reality. I am going to make you the pretty little girl you have always dreamt of being. You need to be taught ho live your every day life properly. You can only dream of being as sexy, girly and attractive as a real w...

Ultimate Sissy Weekend Ch. 03

by SissyTwinkleToes on Jan 13, 2020
Transgender & Crossdressers

Before today, Susie had only ever spanked herself. Nothing could have prepared her for the 220 spanks she'd received earlier, her first serious sissy spanking. Still her butt burns, even in its new pink poofy diaper. And now it's joined by fresh welts and lines on her inner thighs from the cruel canings of the redhead's ruler, as she happily decorates the tw...

Humiliated by Wonder Woman

by littleerection on Sep 17, 2017
BDSM

So it's a nice day today. I decide to go outside to get some fresh air and go for a walk. I wanna soak in the early spring cool breeze. I find myself going through the woods. Eventually I end up near the end and I see her past the trees standing alone on the cliff: The one and only Wonder Woman, looking out over the town! I couldn't believe my eyes! I've alw...

Danni Ch. 02

by Coder3445 on Jan 20, 2020
Transgender & Crossdressers

This story starts where the last left off, read Danni to understand what is going on in this story. Of course all character are above the age of 18. The following story contain feminization and female domination. * Also another description Tara, Danni's Mother Unlike Danni Tara had tanned skin, she was five foot four inches tall. She had green eyes and...

A Week End with Mistress Pt. 01

by gasissynora on Oct 16, 2018
Transgender & Crossdressers

Dear readers this is my first story and I hope you enjoy it. Your comments and suggests will be most helpful. I am planning on continuing the story if the feedback is positive. This story is based in part on facts and part on fiction. I will leave it to the reader to decide which is which. ***** We had just finished dinner and I was in the den getting rea...

Sissification 101: Ch. 03

by silkstockingslover on Jun 8, 2020
Transgender & Crossdressers

Sissification 101 Ch 03 Summary: Eric(a) gets pegged for the first time. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose watching hypno-sissy porn by a very supporti...