Mistress Sissy Stories

31,338 results
Orientation
Length
Source
Infinite Scroll

Mistress Emma's Revenge

by sissymissyct on Oct 15, 2017
Fetish

Hi I'm Ken. Well I was, now I'm called Brenda. Here's a bit of my story for you. I hope you don't make the same mistakes I did. Because until I got caught misbehaving by my mistress, life was pretty good. At 38, I had a great job as an office manager in charge of 25 or so employees, mostly women, a really good salary, a nice office and plenty of job securit...

Sorry Sissy You Lose Pt. 01

by LittleDickSissy on Jan 15, 2019
Fetish

Mistress called her sissy to her chamber, "Slave - you are to come here and upon entering crawl on all fours." Slave did as instructed without hesitation. He was athletic and manly, but his little dick was weak and it drove him to submit to her. Her power was her pussy, her body, her attitude. He knew his needle dick didn't fill her pussy let alone stretch...

A New Life Ch. 03

by sissycinnamonswirl on Sep 18, 2017
Transsexuals & Crossdressers

"Click on this link, sissy. I want to show you something," Mistress Sally said. And I happily followed instructions believing it to be some aspect of sissy porn like a caption, or little GIF video. I couldn't have been more right...or more wrong. My newly painted red lips parted in shock as my computer opened a new browser that showed what seemed to be an a...

Training of Mistress' New Sub Day 01

by naughtyboy082 on Sep 19, 2017
BDSM

As Mistress Sharon has requested, a written story... THE FIRST MEETING MISTRESS SHARON sends out a late night text that her new submissive has been waiting for anxiously all week long as he sought to prove his obedience and worthiness. "Congratulations, sub! You have successfully completed your probationary period...official training begins in the morning...

From a Husband to a Dutiful Sissy Ch. 04

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

A quick note about this chapter. It runs a tad long as I want it to really set things up for Chantel's future, not just some sissy maid for her now Mistress wife, as cool as that can be, but to develop a more varied sissy, crossdressing, maid and slut story. I hope it works for my readers. ***** Chapter Four: Moving on to reinforcing my new lifestyle Satu...

Cum at the Mall

by bottomhub on Jun 11, 2019
Transgender & Crossdressers

"Eat that pre-cum, sissy," -- I masturbated furiously in the passenger seat of her car. I was wearing panties under my jeans, and Mistress knew this; she found it amusing. So would some of the passers by if they only knew what was going on. I could barely keep up with the complications. "And don't waste any!" she continued, sternly slapping her right index...

The Awakening of a Sissy Pt. 05

by sissyjolie4u on Feb 3, 2020
Transgender & Crossdressers

There I was, on my knees, in very skimpy feminine undergarments, locked in a room in the back of an ABS, with 6 men and my Mistress. This was the start of what was to be the other portion of my punishment. Mistress walked toward me with that evil grin of hers. As she was approaching me, she said, "Jolie, these men are here to assist me with your punishment...

The Awakening of a Sissy Pt. 07

by sissyjolie4u on Mar 9, 2020
Transgender & Crossdressers

I was a giddy as a school girl knowing that I would be sleeping with Tim, Curiosity was building inside me. I was going to sleep with a man for the very first time. What was the special surprise that Tim had planned for me. All night long, as we watched sissy porn, Mistress kept harassing my pussy with various levels of my trainer. I was happily enjoying us...

My Little Slut Ch. 02

by Sweetblood03 on Sep 12, 2017
Fetish

"My apologies, Mistress." He pulls up the flimsy black knickers over his softened cock, bends his head and begins to lick the pooled cum off my sleek black boots. "You realize that this means a day with the cage on for your forgetfulness, don't you, pet?" I reach down to stroke his cheek while his tongue works over the leather catching every last drop of c...

Julie's Collaring Ceremony Pt. 02

by julieaugust72 on Dec 25, 2019
BDSM

Welcome to my branding ceremony...Part 2 At this point I have just been branded. When my Master branded me I passed out and shit myself. I woke up with 2 women, Sue and Barbara, cleaning me and explaining the same thing happened to them when they got branded. What follows is the next part of the story. Enjoy and please send me comments. That is how I will l...