Sissy Bbc Chastity Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Sissification 101: Ch. 02

by silkstockingslover on May 18, 2020
Toys & Masturbation

Summary: Both Eric(a) and Joan discover the joys of toys. Thanks to the real Eric who requested and helped plot this lengthy story. Thanks to Tex Beethoven and Robert for editing this story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose wat...

Solo Submission

by Subkoksukr4u on Jul 31, 2019
Loving Wives

He couldn't wait for her to leave for school. He worked from home and loved to play when ever he had the chance. Sex between them was almost non existent anymore but she still gave him blowjobs when ever he asked. That was part of the problem, Matt didn't want to ask for sex, he wanted it forced on him. He dreaded taking control all the time, he was secret...

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...

Anklet Adventure Pt. 04

by dometoo on Nov 27, 2018
Interracial Love

Editor's note: this story contains scenes of incest or incest content. *** The last time Lynda and I returned from our romantic getaway cruise, she came back black bred and knocked up, cuckolding me and keeping me in chastity much of the time. I'm now the proud father of a three-month-old black boy, Mark, her bull's namesake; with strong prospects of havin...

Sailing Away Ch. 23

by Jasmyn_White on Jun 1, 2020
Fetish

Lacy, done with her recollection of the trio of BBC, asks, "what do you think?" "I think it went spectacularly well, and I'm glad you enjoyed so much." "Oh, I surely did my bitchboi. And I've got just the way to reward you. In a sense." I knew you had something afoot. "Let me see your cock, sweetie, I want to unlock you so you can shower." Doing as told...

Naruto the Cuckold

by SwotchItUp69 on Apr 22, 2025

"Naruto, from now on you're going to be nothing but my submissive sissy slut. You will serve me and do as I say. So I demand that you call a meeting with the former Raikage, A." Hinata tells Naruto. "Y-yes, Hinata" Naruto says hesitantly. "IT'S YES GODDESS" Hinata yells. "Yes, Goddess" Naruto replies. "That's more...

Twist

by Seurat on Sep 12, 2017
BDSM

Once, long ago, I got fed up with the way femdom, forced transgender, and loving wife stories with BDSM basis ended; they had grown very predictable. In fact, a few authors had posted short lists of vignettes which, unintentionally, encompassed all of the common endings which I had grown to abhor. My own list, a response to the predictability of those storie...

Adult Trip Pt. 04

by cuckcpl4play on Jul 18, 2018
Interracial Love

Master released me from the tree and quickly positioned both hubby and me on our knees next to one another. He handed me a brief and simple contract and ordered me to read it aloud. Obediently I read the contract as demanded. "You have agreed to be Master's dirty married white whore for the remainder of Master's trip, subsequent trips to this hotel where...

The Inner Slut Ch. 07

by sub2femdom on Aug 22, 2018
Fetish

Chapter 7 - Lexi's Training Two weeks have passed. Amy is proud of Lexi's progress. They've spent about two hours each night practicing makeup, walking in heels, poses, and attire. Lexi even acts more feminine, especially when Mike is around. More than once, Amy has noticed Lexi staring at Mike, specifically at Mike's cock when it shows through his shorts...

Extreme Cuckold Fantasy Ch. 02

by Revan7 on Jul 29, 2019
Interracial Love

Prologue It's been two years since David and Jenny had started to fantasise about cuckolding. Two years after that jenny was pregnant with one of four black man's baby. They were on week away from a villa holiday in Spain with these four black men and were about to go out and get queen a of spades tattoos for Jenny. Jenny was pregnant with a black man's bab...