Ultimate Sissy Weekend Stories

84,140 results
Orientation
Length
Source
Infinite Scroll

A Birthday to Remember! Ch. 02

by searic on Sep 11, 2017
Transsexuals & Crossdressers

We did not speak until I had opened the door to my room and followed my wife/Mistress in. Setting my single suitcase down, I knelt in front of her. She extended her hand, and I lovingly kissed it. "What are your favorite sissy drawings called?" my love and Queen asked. Somewhat taken aback, I nonetheless was immediately able to answer. "Prissy's Sissies, o...

Sissy Boy Secretary Ch. 06

by Hotenuf4u on Sep 19, 2017
Fetish

When we got to the car Elaine said, "This won't do, you are missing something Sissy Boy. Kneel down here," as she pointed to a place just behind her car. I immediately knelt down, hoping no one would see. "Lisa my little Slut, remove your stockings and garter belt," it wasn't a question. As Lisa was getting done removing the items, smiling at Elaine as she...

Humiliated Stable Sissy

by SissyTwinkleToes on Oct 5, 2020
Transgender & Crossdressers

After a long week at work, I was looking forward to a quiet weekend of relaxing in front of the TV with a beer, but my fairy godmother had other ideas. "Good morning sissy," came her stern voice as soon as I woke up Saturday morning. I whimpered, immediately knowing I was in for a humiliating weekend. She frowned, not pleased with my whimpering. She's an ol...

The Proof is in The Pudding

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

When my girlfriend of two years mentioned she liked to watch female impersonators perform, I seized the opportunity to confess my lifelong addiction to cross-dressing. The expected reaction of disbelief was no surprise but her reply of, "Well, let me see you dressed," was although welcomed, a bit of a setback. I'd not planned the truth to be revealed at suc...

Kim's Facial Abuse

by Master Jim on Sep 16, 2017
Transsexuals & Crossdressers

Kim wanted his cock in her mouth so bad, she could taste it. She had hardly been able to sleep the past few nights. She was waiting for Thursday afternoon, when she knew he would be coming over to use her. Master Jim had been wanting to put his cock in her mouth so bad, he was about to explode. He had hardly been able to sleep the past few nights. He was go...

Why Do You Want It?

by MistressMtoyou on Sep 13, 2017
BDSM

Have you figured it out yet? Have you figured out which of your little insecurities is the one that drives you to submit? You've spent hours on the internet reading stories about dominating women bending weak men to their will. You should surely have some idea about submission and why you want it. Have you noticed the way the men give themselves to their Mi...

Sissy Girl Forever Pt. 01

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

The call from Mistress Andrea made my day. I hadn't seen her for over a week and was looking forward to playing with her & having my chastity finally removed. You should know that Mistress and I have known each other for many years and have I always enjoyed being her sissy sub. Lately she has been training me to be more feminine in appearance. I have been r...

Karate Girls Ch. 1

by jabberwok on Sep 17, 2017
BDSM

It was my senior year in High School. Things were looking good. I was going to be on the honor role. College was a surety! All is well. Both my parents worked as reporters for a nationwide newspaper. My dad came home in November with his big break. A sixth month Africa on-site story about Witchdoctors and their "supposed" cures. The newspaper offered the tr...

Big U Pride Ch. 03: The Squad Forms

by latinarita4 on Jul 27, 2020
Transgender & Crossdressers

Remember to check on parts 1 and 2 before you read this! Also, please rate and review my stories! I love hearing feedback from readers! If you have suggestions, just send them right along! Maybe your suggestion will be featured in a future chapter... ________________ Most days at the campus health center were typically light affairs. Usually it's the rout...

The Babysitter Takes Over

by sissysherry2 on Mar 13, 2018
BDSM

"I know your secret." These were the words that I had both dreaded and longed to hear from my babysitter. Let me start at the beginning. I am single and have a couple of kids at home who aren't quite old enough to be on their own when I have business obligations. I share custody with my ex, who left me to be with another man, who happened to be black. I ge...