Bbc Sissy Chastity Stories

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Orientation
Length
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Infinite Scroll

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...

Sam's New Position Ch. 02

by worzel on Dec 11, 2018
Fetish

Sam woke with a start, She couldn't see, everything was black! Her arms were painfully pulled back, and tied like a strappardo but taking her weight. her legs weren't touching the ground, They were pulled apart by a spreader bar and tied off a few inches off the bed where Sam had been told to sit many hours before. The past week had been absolute hell for...

A Date with My Wife

by MisterEEE on Apr 17, 2019
Loving Wives

"Strip". I was shocked. Rarely did my wife look or talk like this. I had just come home from work to an unusually quiet house; the kids were nowhere to be seen or heard. They were probably out playing with friends. I wandered into the laundry room; empty. The kitchen and living room were equally quiet. I started down the hallway and noticed the bedroom light...

Be Careful with Your Cell Phone

by redwolf555 on Jun 19, 2019
Fetish

Steve was having a good day at the store that he managed. The store, a dollar discount store, was busy so time was moving along. A new employee had started last week and was doing very well. During a busy moment, Steve had set his cell phone down under the front counter to deal with a situation. Normally, Steve would never do that. There were things on the c...

Liz

by SEVERUSMAX on Jun 12, 2019
Interracial Love

I hadn't seen or heard from Liz in a good, long while, so running into her in the mall was a bit of a shock, given how much it was out of the blue. It was also a little jolt to see the engagement ring on her left hand, not that I resented her presumed marital bliss. I hadn't been invited to her wedding yet, but I would have been more shocked if I had. Old fl...

Katt's New Toy Ch. 01

by econut on Sep 11, 2018
BDSM

SMACK! Katt's hand came down swiftly, squarely hitting her target. A muffled wail emanated from beneath her buttocks as the body of her subject bucked, his legs spasming in front of her. Katt smiled and laughed openly. She was truly enjoying herself. Ostensibly, she was punishing her slave for cumming without permission, but truthfully, she just really like...

Better as Emmy Ch. 01-05

by cactusaur on Jun 8, 2020
Transgender & Crossdressers

Hi everyone! It's been a while since I've posted any new stories here, but a fan reached out for a continuation and cross-over of the Emmy's New Kinks and Better as Riley stories. This new story builds on the characters, themes, and storylines from Emmy's New Kinks and Better as Riley. I recommend reading those before diving in here. Themes: Feminization, t...