Sissy Bondage Stories

20,137 results
Orientation
Length
Source
Infinite Scroll

OMG Mom!

by TheSecretlyUnlikelyDuck on Feb 5, 2019
Interracial

You pull into the driveway of 15 Preston Road at around 3pm on a friday afternoon. The light of the late spring sun pours over you as you come to a halt, parked behind the red BMW belonging to Mary Lange. She is a gorgeous blonde, who looks far younger than her actual age of 39, and is unarguably the head of the Lange household. You don't see her husband's c...

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Jolene's Momma Pt. 01

by ValoryG on Jul 27, 2020
Transgender & Crossdressers

(The names and locations in this story are completely fictional and have no connection with any person living or dead.) My name's Chris. Wife Jolene and I have been married six years now. Live in the small city of Centertown, Ohio. It probably got that name because it's about half way between Columbus and Cincinnati. Being from a midwestern small town, the...

Miss A's New Play Thing

by Pornenthusiest on Oct 8, 2019
BDSM

Chapter 1: Sexual Awakening Alex's morning ritual had changed lately. Typically he would start his day by slamming his alarm clock, getting out of bed, brewing coffee and taking a shower. But now, Alex was generally restless, always waking before his alarm could rouse him. He would rush to his computer immediately checking his messages, today was no differe...

Caged Sissy's Release

by thesebreasts95 on Dec 2, 2019
Transgender & Crossdressers

"Perfect" I say, as I enter the room. "Good girl". You're kneeling in front of me, just as I had instructed you to; eyes to the ground, hands on your thighs, collared. You're such a pretty sight. The little black dress you're wearing is tight, making your fake tits look so big and full. I walk forwards towards you, bending down, cupping your chin, tilting...

Rubber Femdom World

by Rubberfoot on Oct 15, 2020
BDSM

Something strange was happening in the small college town of Little Gadsden. None could say what was causing it, but the one thing that was certain was that it started after the comet crashed near the town. Little Gadsden was a small place, of no more than a few hundred inhabitants, so the event was the most talked about thing for weeks, even though nothing...

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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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Ms. Alexandria - Interview No. 02 Pt. 02

by gasissynora on Dec 3, 2019
Transgender & Crossdressers

This is the third part of the Ms. Alexandria series and part two of The Second Interview. I believe it will stand alone, but will make more sense if you read the earlier parts of the story, particularly Part 2a. This part starts with the last paragraph of the previous part. Ms. Alexandria: The Second Interview -- A day out. Part 2b Mistress walks up behind...

Transforming Brent Pt. 05

by sissymissyct on Dec 2, 2019
Fetish

I awoke early, partially due to the pressure of morning wood in the chastity. Once I settled down, I showered and slipped on a robe and quietly made my way to the kitchen. I quickly familiarized myself with the layout and, finding what I needed, started cooking a nice breakfast for my mistresses and myself. Ham and cheese omelet, OJ, toast and sausage, along...

Tales of Sub Asian Sissy Ch. 03

by subASIANsissyJADE on Apr 23, 2019
Transgender & Crossdressers

(Thanks so much for taking the time to read my story! This is just my third post and I'd love to hear any feedback, questions or comments. Also, please feel free to contact me if you just want to chat with a very submissive asian sissy. XXX, jade) *** While it's only about fifteen minutes away, the drive back to my apartment seemed to take forever. I had t...

For His Mistress's Pleasure Ch. 02

by femmepen on Sep 12, 2017
BDSM

I heard a car coming up the alley and moved to the left a little to be hidden from sight, though with all the shrubbery I knew I was out of view. Her silver BMW drove right past the patio into the spacious garage as I looked down afraid to meet her sunglassed glance. The engine was turned off as the solid sound of the door opening sent shivers up my spine. T...