Cuck Sissy Stories

7,847 results
Orientation
Length
Source
Infinite Scroll

Blindfolded Surprise

by LilithsCuck on Oct 6, 2020
Fetish

Ken sat cross-legged in the middle of the room, unsure of where Lilith and Matt were in the room. Lilith had blindfolded Ken before making him disrobe. Ken couldn't see the look on Lilith or Matt's faces when he took of his underwear, but he could hear Matt's snicker as the small steel cage flopped out from behind the elastic of his underwear. Lilith laug...

My Sissy Cuckold Life

by SissyCuckMike on Jan 2, 2021
Fetish

Hello everyone, my name is Mike and i am now a sissy cuckold. If you don't know what a sissy or a cuckold is i will explain, a sissy is like a cross-dresser but usually dresses up in pink frilly women's clothing and cuckolding is similar to a hotwifing where she goes out on dates and fucks other men without her husband/boyfriend around but with cuckolding it...

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Fucked a New Hotwife Pt. 01

by MattieG on Sep 14, 2017
Loving Wives

Last night I met a new Hotwife/Cuck couple for the first time. He is very submissive to her, and she was craving someone very dominant that she could let go with. We had chatted by text for a couple of days and I figured we would meet in a few days have coffee and maybe meet and play in a couple weeks. With all of the talk her cuck was super excited and was...

A Pro-Wrestling Cuckold Ch. 07

by longhairedcuck on Mar 3, 2020
Fetish

It didn't matter to Darren that I hadn't come in 5 weeks. He insisted on keeping me caged for a week longer even though I was supposed to be let out earlier. He broke the news to me one fine Saturday morning after he'd stayed over at our place. I stood there gaping as he calmly told me about my prolonged chastity. "But, but..." "No buts cucky. This is ex...

The Ultimate Cuck Experience

by Joggles44 on Mar 12, 2021
Cheating Spouses

(UPDATE: Custom names for all main characters have been successfully added! Enjoy!) (Note from the author: Hello! Hope you enjoy my story. Before you start reading let me clarify that this story is set to "private", meaning no one can edit it or add chapters but me. I'd like to keep the writing to myself while the project is developing. HOWEVER, I...

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The Two-Month Break Clause Pt. 02

by TheBiGuy on Mar 25, 2019
Fetish

After my first post, I received several comments. Some of the comments were positive and others negative. Any comments that were constructive, I will take the criticism and learn to incorporate those suggestions into the subsequent chapters and other stories I write. One of the comments was about numbering the story as Part 1 or some variation like that. Tha...

Cuck Husband

by SatinSlip on Oct 15, 2017
BDSM

We didn't choose this lifestyle. It was forced upon us. Well, perhaps that's not quite true. Maybe best to say that my wife and I were forced to confront who we truly are. My wife is way out of my league. I'm a nerdy, small accountant. About my only good feature is my nice ass. Though even that's a bit too feminine. My wife, Cherry, on the other hand is...

Meet the Danvers Ch. 02

by eeric on Nov 26, 2019
Interracial Love

Jim Danvers sat behind his desk on the third floor. He had been the office manager for the last five years, and the last couple of years had been quite profitable for the company. "Have to congratulate you again Jim, another year, and we've seen nothing but increased revenue streams and productivity from your floor." Charles Vanderholm stood up. The man wa...

A Pro-Wrestling Cuckold Ch. 06

by longhairedcuck on Nov 4, 2019
Fetish

We walked up the driveway, silently, the nervous excitement palpable in the air and in us. I gave Lily a once over, she looked incredible, dressed in a quaint top and shorts. Her long blond hair flowing down her back in loose curls, all the way to her ass. I stared at her bottom longingly. Darren had forbidden me to touch it, deeming it as his 'property'. O...

Find the Cheerleader, Save the World

by Sissyhalo on Sep 16, 2017
Transsexuals & Crossdressers

It started with my brother Holt. A year younger than me he's...he's turned into a fucking cuck sissy faggot. I'm serious and I'm not just spouting off. Holt's always been a dense guy but this...he starts hanging with this loser from high school and I mean a loser. AV club, geek stuff, nothing in Holt's yearbook that said anything but loser, geek and loser...