Sissy Humiliated Stories

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My Mistress is My Wife Ch. 02

by slavetohiswife on Sep 14, 2017
Fetish

I'd spent what seemed like forever locked away in my cock cage, looking at and downloading porn for Mistress while she slept. I felt like the slightest touch to my cock would cause me to explode. I had tried and tried to touch myself the whole time but the cage more than served it and Mistresses purposes. I was only able to get so hard and my balls ached. I...

Humiliated Sissy Slut

by Allice on Sep 16, 2017
Transsexuals & Crossdressers

I have been dressing as a woman at home in private for many years. No one has ever seen me dressed as a sissy slut before but I do it to feel sexy. I know I would never pass as a woman for I am 6 feet tall, 170 lbs and at the age of 45 not a real trim body. My girlfriend Rachel who lives with me is must younger at the age of 35 with a young trim body that h...

I Learned My Lesson Well Ch. 02

by Angelscuck on Sep 14, 2017
Transsexuals & Crossdressers

As I told you in part 1, Angel really taught me a lesson regarding cumming without her permission. I was so grateful that I hadn't lost her to a superior black stud, I was even afraid to masturbate to porn on the internet. We have two computers, hers and mine, next to each other in our office. She told me she had forwarded an email to me from one of her gi...

Sissy Amy Loves Mummy Belinda Ch. 02

by Sissy Adele Howells on Sep 17, 2017
Fetish

Mummy Belinda Beynon was now in complete control, as she pushed my pram down the road. I snuggled against my satin sheets and was very content. Mummy Belinda removed my dummy every five minutes, wetting it with her saliva, before putting it back into my mouth. Staring up into Mummy Belinda's pretty face, was a dream come true. She would tease me, by blowing...

Mistress In Control

by polishjoe on Sep 17, 2017
BDSM

Last Friday evening when I got home Mistress informed me that tonight was going to be a very hot night but I did not realize until later just how hot things were going to get. Mistress had dinner ready and she told me she wanted us to eat quickly so we could get straight to the "activities" she had planned. I thought it curious because Mistress usually did...

April Fool Office Sissy

by lululuvsblack on Apr 10, 2018
Transsexuals & Crossdressers

"Dear Colleagues This week, in order to help with our efforts to raise money for charitable causes, we have decided to mix up our usual policy of dress down Fridays. This Friday we are instead instigating a "dress up Friday" in which staff are strongly encouraged to come to the office dressed in the office attire of the opposite gender (that's suits and tie...

The Cuckold is Black This Time

by Samuelx on Sep 11, 2017
Transsexuals & Crossdressers

After months of hesitation and much soul-searching, a momentous decision finally got made. The big Black dude burst into Mistress Chocolate's den in downtown Ottawa, Ontario, and told her of his rather unusual request. The six-foot-tall, gorgeous Black Canadian female dominant listened to him, and then agreed to make his most forbidden fantasy come true. It...

The Awakening of a Sissy Pt. 08

by sissyjolie4u on Mar 30, 2020
Transgender & Crossdressers

It was only a matter of minutes before Mistress pulled the car into a long driveway. My mind was still processing the idea that I was now on hormones. Once we were parked, Mistress had me grab my bag and follower her on the path to the house. She clearly knew this pace well, as she walked right into the house, with me following closely behind. As soon as we...

Mistress Kate Pt. 02

by corduroysissy on Mar 7, 2018
Transsexuals & Crossdressers

When he arrived home from Regan O'Reilly's office Jordan was still in a daze. He needed a drink, no scratch that, he needed a bottle. In a matter of a couple hours he'd gone from having his life threatened, to getting a blowjob from the Leprechaun, to being ordered into sissy sexual servitude by Mistress Kate. She was actually expecting him to be her fucking...

Miss Guided Pt. 02

by MissMarianne on Mar 26, 2019
Transgender & Crossdressers

I arrived at Dr. Bill's office and he greeted me and we sat chit-chatting together for about ten minutes. Then, Charles and Emily arrived. Dr. Bill addressed us all. "I have read Dr. Price's diagnosis and report and I concur with her findings and recommendations. It's probably best that Dr. Price tell us about them herself. Dr. Em began saying, "Well, f...