Ultimate Sissy Weekend Stories

84,140 results
Orientation
Length
Source
Infinite Scroll

Naked at the Christmas Party

by BobDogwood on Sep 13, 2017
Exhibitionist & Voyeur

Dorothy was more than kind enough to lend Derek – that's Derek, she lent Derek the car. I'm stressing this because I didn't want anybody to think that she let me drive her car. Besides never having driven a car before, I had no driver's license. Everything went fine, although it must have surprised a lot of motorists when they saw a great big roly poly Sant...

Princess's Night Out

by Subboi23 on Mar 17, 2020
Fetish

As Her laughter fades down the hallway, Her dog Titan barks twice. A quick ruff ruff. i think he is confused by his freedom, as i lay locked in his crate. i can hear him walking around, but am unable see him. i am blindfolded with my hands cuffed behind my back. The only clothes i have on are a pair of soft pink panties. My tiny little dick is locked in chas...

The Transition Ch. 02: Jamie

by Quantarx on Jul 6, 2020
Transgender & Crossdressers

Greetings and thanks again for reading my story. Please be patient and allow this story to grow. As always I really appreciate any feedback you leave in the comment section down below. Be sure to follow me if you like the story so you don't miss any future chapters. ************ My voice trembled as I forced out the words " Hey Mark this is Jamie, did you...

Roots Ch. 01

by Alexis_White on Jul 29, 2019
Erotic Couplings

Author's Note: all characters are at least eighteen years old. ***** Chapter One Friendship I can't remember how we became friends. If someone asked, I would say that our parents were friends before, and we became friends by association. If someone thought that my explanation was faulty, they would press me for a better answer. It just didn't seem possi...

One Step Too Far Ch. 03

by LanaChu123 on Dec 9, 2019
Transgender & Crossdressers

"Lana... Lana..." "Lana?" My eyes fluttered open sleepily. Ms Garvey calling out to me as she undid my foot bindings with the wrist bindings already undone by either side of the bed. I rubbed my wrists and could see the hosiery ripped where bindings had been at my feet. "Sorry to wake you up but I think it is better to get on a schedule." I sat up cross-le...

Satan's Script

by SevMax2 on Jul 14, 2020
NonHuman

"You're a hard man to find, you know?" I heard behind me, turning around to see her there. My little sister, Stephanie. The only part of my growing up that I remembered fondly. The only person growing up, including our parents, who didn't treat me like dog shit. Suffice it to say that my overall first impression of the much vaunted traditional, nuclear fam...

Whitewash High: Rising Sun Ch. 12

by EnglishTeacher on Jul 20, 2020
Interracial Love

Nik slipped out of his quiet apartment, mask already on, and casually walked down the stairs to an awaiting car. Musashi and Ryuji both leaned up against the expensive, luxury car. "Sleep well? The girls told me you were insatiable on set. You're getting your groove back," Musashi joked, pointing to the passenger seat. "He fucked half-a-dozen girls in a si...

Okaikei

by bleepblorper on Apr 3, 2019
Anal

Note: This is the last chapter in the trilogy starting with Worth Every Yen and continued in A Few Yen More. It will not make sense without having read those first. ***** The alarm on my phone wakes me far too early to a room that's still dark. I turn my head to the left, then the right, hearing the bones in my neck pop. The noise seems loud to me, but it...

A Chance Encounter Ch. 02 - My First Rodeo

by fexhominum on Jul 15, 2020
Fetish

THE NEW GIRL A brunette with exotic features answered the door. She opened the door halfway, and leaned out from behind it. She stared blankly at me for a moment. Finally, she spoke. "Yes?" "I have an appointment." I said, meekly. "Come in, pig." I opened the screen door and stepped into the house. She was wearing a green scotch plaid flannel shirt. A m...

Freja and Jeanie Ch. 03

by BiscuitHammer on Sep 14, 2020
Romance

Freja & Jeanie Disclaimer: Welcome to Freja & Jeanie. This story is part of my larger story cycle, commonly known as "The Alexaverse." As always, many thanks and gratuitous panty-shots courtesy of Freja and Jeanie are directed at my long-suffering editor and Beta-reader, who makes sure my grammar is on point. Constructive reviews and critiques are w...