Cruel Chastity Stories

25,831 results
Orientation
Length
Source
Infinite Scroll

Respect Ch. 02

by rachaelross on Sep 13, 2017
Loving Wives

I stood in front of the mirror in the bathroom, wiping the fog away so that small beads of water ran down my reflection. I touched myself, moving my hands lightly over my stomach, turning slightly to profile. I was large now, and round, swollen with the life inside me. I could feel my skin tight and smooth and firm, almost hard, and it was difficult to remem...

Family Issues Ch. 03

by allthatisfuta on Jan 31, 2018
Transsexuals & Crossdressers

First things first, I need to thank Madison (ThanatopicFolds). Your keen eye, your love for the written word, plus your generousness, were what this story dearly needed. I really hope you'll have a good trip, in whichever road you choose to take, mate. Family Issues - chapter 3 $$$$$$$$$$$$ The penthouse's door whined as Kevin pushed it, and he cringed. H...

Family Issues Ch. 09

by allthatisfuta on Jul 4, 2018
Transsexuals & Crossdressers

Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. As always, I need to thank, Stylus and Madison (ThanatopicFolds) my cool editors. This time they've made an extra effort and that's why I can post this episode so quickly. $$$$$$$$$$$$ "Margarita was never short of money. She could buy whatever she liked...

The Book Signing Pt. 03

by FOUNTAINPEN67 on Sep 12, 2018
Group Sex

We arrived back at the suite. It had been a loud ride up the elevator. We were all gropes, laughs, and jokes; somewhat cranked up by what had happened that day, (and now ready to unwind with considerably less clothes on us and considerably more room service in us). No sooner had the door to the room slammed behind us then we'd begun shedding clothes. We wo...

Beetlesmith's Ch. 24

by dresbach on Jan 2, 2018
Sci-Fi & Fantasy

The warning about the 'kitchen sink' at the beginning of the last chapter still stands. ** I am just a worthless liar. I am just an imbecile. I will only complicate you. Trust in me and fall as well. I will find a center in you. I will chew it up and leave. I will work to elevate you just enough to bring you down —Sober by Tool, Undertow ******** Jackie...

Life at Last Ch. 06

by lance gt on Sep 17, 2017
BDSM

As they drove back along the way they came, they passed by the store again and saw Vanessa and Chanelle still inside. "Stop here for a minute honey, I want to see what's going on in there." Trisha asked Katherine. Katherine pulled over directly across from the store and parked. They sat and watched as the two women argued and saw Vanessa push Chanelle a...

Teacher's Pet

by SeekerOfHerself on Sep 25, 2017
BDSM

Note: chapter I of my story "the Amphiboid" gives a bit of background on this, I'd recommend reading that even if chapter II onwards is not for you. I. I had planned to seduce my former teacher for a long time. My efforts at exposing myself to Miss Davis were quite forward and my new source of information led me to conclude that my scheme had sparked somet...

Angela's Education

by Xantu on Sep 13, 2017
BDSM

This is my first submission to Literotica. Like Angela I have much to learn. I look forward to your feedback. * Angela's heart jumped every time the phone rang. It had been over three weeks since she had heard from Devin. He had never neglected her this long before. His voice was dry and business like, "My flight arrives 9:57 pm tomorrow. I will be in Ne...

Prisoner Ch. 05

by angiquesophie on Sep 19, 2017
BDSM

Chapter Five. For the next few days, life was a bowl of soup. It had no shape, no focus, and no target. He'd returned to his apartment, hardly recognizing it as the place where he'd lived before. At first he'd tried to sleep. Then he'd tried to read, watch television, sleep, eat a sandwich, hear music, drink beer, sleep, watch television, and drink booze. T...

Sex and Vengeance Pt. 04

by Ekstatikoi on Jul 16, 2019
Novels and Novellas

Time for the content warning, folks. This installment features heavy duty BDSM and the big ol' lady dick from part 2. Oh, and adultery and heartbreak. So, you know. Watch out if you don't dig on those! ***** Each sip of the icy cocktail gave Karandreya a small shiver that had very little to do with the temperature. She'd ordered the first thing the beleagu...