Chastity Pegging Stories

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Discovering Mistress Sarah's World Pt. 08

by oneguy4fun on Sep 14, 2017
Transsexuals & Crossdressers

Part 8 -- Complete Surrender Chapter 21 Leaving Behind Joe's Life Mistress Sarah was very pleased with Josie's training and feminization. She was anxious to have complete reign over him so she sent him home a day early to pack up his things and prepare to leave behind his life in the Philadelphia suburbs. "I'm sending May with you Josie," announced Mistr...

Made to Obey Ch. 11

by madetoobey on Aug 21, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). I'd been forced into a chastity cage and made to wear panties all the time. Humiliation was now a frequent event. Esther, who had investigated my internet usage on my laptop to see if I'd visited shema...

The Life and Tines of Slave N Ch. 02

by Discordianknot on Sep 13, 2017
BDSM

Wherein I demonstrate the importance of rigorous and intentional conditioning of a slave for complete service. As I explained in the first part of this story, I do not often rely on chastity devices these days to control N's sexual behaviors, though that wasn't always the case as I'll explain shortly. I mostly rely on the "honor system" - by which I mean an...

Mistaken Identity

by kcwilder69 on Mar 25, 2019
Erotic Couplings

It was my first week at the new job, and I was drained from learning new protocols and procedures. And how would I remember the names of all the people I'd met? I parked the SUV in the driveway, looking forward to a warm dinner and a quiet evening. Approaching the house, I see it's dark. Why isn't Laurie home? She's always home by this time. I open the door...

Grace Under Fire Star Does Blacks

by Samuelx on Sep 17, 2017
Celebrities & Fan Fiction

Brett Butler looked at herself in the mirror. At the age of fifty three, she still looked good. Blonde-haired, blue-eyed and curvy. Blessed with Irish good looks that simply refused to fade. Unlike her star in the upside down world of Hollywood. That one faded so damn fast she went from being a household name to a nobody in no time. It had been so long since...

Black On Black Pegging: True Love

by Samuelx on Sep 11, 2017
Fetish

I don't know why he thought I wouldn't be able to handle it. I really hope he'll stop hiding stuff from me after this experience. Female on male strap-on domination, Afro-Caribbean style. Seriously. I honestly wish he told me about this really hot fetish of his sooner. My name is Malinda Lexington and I'm a short-haired, green-eyed and kind of chubby young B...

Learning to Let Go

by NRMathis on May 15, 2019
BDSM

Jonah could not remember a time when he was more nervous. Per his habit, he showed up far too early at the Cheesecake Factory, and was waiting at a table. For her. For the woman he had been chatting with online and exposing some of his deepest, most embarrassing fantasies to. The woman who wanted to meet him in person. The Domme who he wanted so badly....

Taming the Dom

by Ben Rosewood on May 31, 2019
BDSM

This story has been created with Game Mode in mind. For the best experience, please turn Game Mode on. Your best friend Eddie had said it was urgent. Upon receiving his text, you head to your normal meeting place, Godzilla's Pizza Dojo. The place is covered in framed monster-movie posters and arcade machines that Eddie has topped the high scoreboards on. You...

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An Anal Beginning Ch. 01

by caffinated on Sep 16, 2017
Anal

This is the beginning of a longer story. It is the first piece I am publishing in this format. Your feedback is welcome. John's deepest desires left him lost. He longed for something that went against every fiber of his being. John's girlfriend Heather had opened a door to his sexual exploration, and now John longed for more. His deepest desire was hard en...

Kinky Awakening Ch. 01

by rj1774 on Oct 13, 2017
Fetish

FYI, this story features CEI and pegging if you are uncomfortable with that click to next story. ***** My husband is a high powered attorney which allows me the luxury to stay home, volunteer, and keep up my hobbies. This made what I found even more concerning at first. He left in a hurry one morning and forgot to shut down his laptop. Not thinking anythin...