Chastity Surprise Stories

139,463 results
Orientation
Length
Source
Infinite Scroll

Cuckold in Chastity

by at_yur_service on Aug 6, 2019
Loving Wives

Mark and Cynthia were out for a walk near their house when they ran across a young, fit asian woman they'd never met before. She introduced herself as Anna, and said that she and her husband Jason lived nearby. Anna proposed that they get together sometime, and they exchanged numbers. Later that week, Anna invited Mark and Cynthia over for dinner and drinks...

Collecting Catholics: Chastity

by Sosela on Sep 12, 2017
NonHuman

"You have to come see this!" Catherine giggled conspiratorially, looking left and right to make sure no teachers or nuns were around. Mt. St. Vesper Ladies Finishing School was quite strict, and the staff tended to spy on their students even though they were of legal age. It was a catholic college in all but name, and even though the Dean said that student...

We Rule the School Ch. 04

by TheWorldSpins on Sep 16, 2017
Group Sex

Katie Greenwood couldn't decide if she was looking forward to a confrontation or dreading a meeting with her ex. Last Halloween, Simon, the guy she thought was the perfect boyfriend, had more or less blackmailed her into a public, humiliating anal sex experience. She still wondered why she had gone along with the whole scheme. Simon's blackmail was based on...

Chastity's Lessons Ch. 03

by Goldeniangel on Sep 19, 2017
Interracial Love

Chastity had returned to Jeremy the very next day, eager for her next lesson... and her hot little pussy was eager for some more of his black cock. To her delight, he'd had something new to show her immediately, stripping her down and laying her down in their clearing, instead of fucking her immediately he straddled her head with his large black thighs and l...

An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...

A Slave's Journey Ch. 06 - The Facility

by punishedone on Apr 14, 2020
BDSM

Susanne went off to the yoga room while matt and I went to the wrestling room for a circuit training class. We arrived a few minutes early and I introduced matt to some of the other members and made idle conversation. While everyone waited for the class to begin I grabbed a bottle of water for myself and one for matt. As we drank before we started the class...

Romancing the Raptor

by Cashmere_Snow on Sep 15, 2017
NonHuman

Tiffany. Maria. Sandy. Destiny. Chastity repeated the names to herself as she directed a coy smile at the man she had brought back to her apartment. Tiffany. Maria. Sandy. Destiny. They were the names of the women he had raped and then sent to the grave in one case and into the ICU with the others. They were women like her—women who shared an... affliction...

The Release of Heidi's Rest Pt. 04

by BacchanaliaoftheRedWolf on Sep 23, 2019
Sci-Fi & Fantasy

Part the fourth - In which the circle is no longer needed. Sister Petra had been missing for two days now, and, as the Mother Superior laid out the morning sermon for her sole remaining Sister, she sighed. She could see the glances, not at her, nor at the symbol above them, the symbol of their faith, but the doorway. More specifically, the doorway to the h...

Becoming Friends Ch. 02

by mrbillcollecta on Sep 17, 2017
Loving Wives

"What time are we expecting Chastity over for drinks baby?" Stefan quizzed. "About 7 or so and she is bring the Margarita mix with her!" Kenya yelled from the bedroom. He replayed the events that unfolded before him in his own bedroom a few short hours ago. Seeing Chastity tugging and sucking on Kenya's huge 42DD tits was definitely the highlight of his da...

How I Became a Chastized Cuckold

by gizzard on Sep 26, 2017
Loving Wives

I have been married to my wife Angie for nine years and up to about two years ago we have led a pretty normal life. We did what most married couples did. We went to work, enjoyed each other's company, and found pleasure in each other's arms, remaining faithful to one another. We were very happy with the arrangement, until about two years ago when things were...