Ultimate Sissy Weekend Stories

84,140 results
Orientation
Length
Source
Infinite Scroll

Making Holly

by Sissyhalo on Sep 19, 2017
Transsexuals & Crossdressers

My name's Jamie and I moved back to my hometown. I had a lot of bad memories here and most of them stemmed from being bullied in high school and a lot of that came from Holt Thompson. A loud mouthed jock in school he was the center of the basketball team and really, really arrogant. I was a geek, a comic kid and dungeons and dragons kid and all that stuf...

A sissy visits the Headmistress

by maturesubmale_for_F on May 12, 2020
Transgender & Crossdressers

1. Miss Stern delivers both punishment and pleasure I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the...

Wife in Control Ch. 04

by wifetoy on Sep 25, 2017
Fetish

This is the fourth chapter of my wife's execution of the punishment poem I submitted to her suggesting ways to atone for my inability to control my orgasm. Please review the earlier chapters for the full poem and the humiliations I have been forced to endure because of my failure. I did not think she would actually perform all of these cruel punishments on m...

Appointment by Card Only Ch. 06

by Sputnik57 on Sep 17, 2017
BDSM

His landlord was not best pleased when Bruce announced his immediate departure, but was happy to hand him a bill requesting three months rent in lieu of his vacation without notice. He packed his laptop and the few items of decent clothing and sparse possessions into a sports bag and slung it into his car, then drove back to the house, his mind racing; he co...

The Dominatrix

by magicrub on Sep 17, 2017
BDSM

The dominatrix looked stunning standing there before him. "Out of your clothes bitch!" she demanded. "You know what your purpose is here." He undressed as fast as he could, nearly tearing his clothes off. "On your knees slave!" she demanded as soon as his clothes were removed. "I gave you no permission to stand before me." She circled him, eyeing him as s...

XXX-Women Ch. 03

by scatwoman on Sep 14, 2017
Celebrities & Fan Fiction

NOTE: is you just wanna get to the nasty stuff, you can skip the marked-off section that deals with the background and set-up... * * * * * The Premise: XXX-Women After founding the original X-Men, Professor X was often found to be missing or believed to be dead or off on some secret mission he told no-one about. In truth, Professor X was training an enti...

Simone

by Sissyhalo1 on May 11, 2020
Transgender & Crossdressers

I'm so sick and tired of my life. It was like I'm cursed. I wasn't a great looking guy in high school with bad skin and bad grades because well... I was poor. My old man was a night watchman and mom was a stay at home mom because she was poor and had no real education past junior high when she started popping us out. So everything was tight and for the m...

The Sissy Models

by neverless on Mar 12, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** "It's not something I've ever done," Daddy said, with a frown though the fact he hadn't laughed it out of hand meant I knew I had a good chance of persuading him. "There's a first time for everything," I answered. "What if someone recognises us, Ricki?" he asked. "They won't"...

Sarah's Sister-in-law

by SarahCD on Jun 11, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change...

Office Cumslut Ch. 01

by DrLuverotica on Sep 12, 2017
Loving Wives

FRIDAY MORNING "Are you going to work dressed like that Jo?" My wife was dressed in black, sexy high heels, black stockings with a pink 1920s style pencil line up the back of them, pink frilly satin panties (she hates thongs) and matching push up bra. "Yes I am hubby," she purred, as she pulled a navy blue, short pleated skirt over her hips. "Is there s...