Sissy Chastity Cuck Stories

13,492 results
Orientation
Length
Source
Infinite Scroll

Aprons For Gayle Ch. 09

by Addicted2Writing on Sep 26, 2017
BDSM

AUTHOR'S NOTE: Gayle is the young American woman who has taken on a six month contract to be a submissive maid to Hamish while living in a Scottish castle. This is in order to pay her mother's medical bills. We left our heroine on Wednesday night after recouping from stinging nettles and a disheartening call home for the first time. ***** CHAPTER NINE TH...

India: Wife's Forced Awakening!

by Makarand Kakkad on Sep 18, 2017
Loving Wives

Our Kinky Money Lender Takes My Wife! I was in deep trouble. I had taken huge loans from Jaichand, a shrewd money lender in Indore. Jaichand was an old man, but reputed to be extremely crooked and violent. I had not been able to repay him back, despite being warned a lot of times by him. Now he had sent a message that he was coming to meet me in the office...

The Prom Date Ch. 03

by Kellog on Sep 16, 2017
Exhibitionist & Voyeur

Chapter III: A Kellog Serial "Hi, guys and gals," Cindy said into the video camera. From the background behind her, it was apparent that she was sitting in a car. "It's me again. Time for our next update. Thanks for checking in. "For those of you who are bidding, thank you and keep up the good work. But we're not even halfway where we need to be. I figure...

Payback Ch. 01: Entrapment Begins

by Sucker4Gurls on Sep 19, 2017
Transsexuals & Crossdressers

The phone started ringing at 9:44 pm. That seemed awful late for a non-emergent call, but I let it ring anyway. "Call from San Diego, Kaw," it said, and again, "Call from San Diego, Kaw. I guess the telephone voice machine didn't know that CA stood for California not "Kaw." I get so many crap robo calls that I only answer calls that my system identifies by s...

Mild-Mannered Man Transformed

by JMaxwell69 on Sep 14, 2017
BDSM

Only here could you see the Abominable Snowman walking hand-in-hand with a Wood Nymph. Steve Batson, on the other hand, wore khaki pants, a button-down shirt, and a navy sport coat. As he strolled down the convention center hallway occasionally weaving through the clustered crowds that were milling about on the dark and geometrically-patterned hotel-grade ca...

Lessons

by Kau_Wela on Sep 17, 2017
BDSM

It had been a long hard day. Calls poured in all morning and the paperwork had piled up twice as fast. Thankfully it was now over. I sighed and put the last of the documents away. I sat back at my desk and leaned back in the chair. Trigg stood on my right. I smiled up at him and he beamed. He bowed slightly and remained standing. I looked at him and got an...

Minerva

by Falcinator on Sep 17, 2017
BDSM

Author's note: This is the edited second edition. This was the first story I ever submitted to Literotica, so it astonished me it wasn't as bad as I feared it would be. There was originally going to be a sequel. Guess that never happened. Original note: This story is intended as humor, not as material for a quick wank, so be warned. It's not meant to be...

The Club Pt. 02

by CindersCinders on Sep 16, 2017
BDSM

The following week had somehow dragged and flown by at the same time. We were both incredibly excited at the prospect of a room at The Club and I'd shown you the pictures of what might be in store for us. Your response had been amazing and utterly arousing, fucking me hard in front of the PC as you stared at the different rooms. There were about a dozen ro...

The Devil in Hannah Prynne

by JulianDelacourt on Oct 8, 2019
First Time

This story is an entry in the Summer Lovin 2019 contest. Please vote. Thanks and enjoy! No one has to tell me how badly I fucked up. On the second night home of my summer vacation from university, I go to a house party with my best friend in high school, Darby, get wasted, and throw up on my front yard where my mom finds me curled up asleep at 6:30 in the m...

Lost in a Female's Pleasure Pt. 09

by LucysFox on Oct 7, 2019
Transgender & Crossdressers

Synopsis: Damien was looking forward to a relaxing weekend free from his abusive father but things quickly took a downward turn when he got kidnapped. It appeared that maybe it was for the best, or at least not as bad as staying with his dad would be. Things start to become more complicated though as Damien reaches the brothel and panics, resulting in the f...