Chastity Cruel Stories

25,831 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

The Keyholder Ch. 10

by AndreaJordan on Dec 11, 2018
BDSM

Amy was trembling as she hurried to the train, her leather boots clipping loudly, and her white cotton trousers feeling warm and tacky as they stretched to contain her long striding legs. Ben had slipped the only key to his ankle shackles somewhere inside her trousers and she hoped like hell that the key was still in there. If not, Ben was fucked. She slippe...

Seduction at Belinda's House Ch. 06

by AndreaJordan on Aug 21, 2018
BDSM

The room seemed very quiet and empty once Belinda had walked away. She had left the small hatch open, giving James a four inch by four inch view out of the trunk, but even that only seemed to add to her cruelty. He focused on Belinda's clothes that she had strewn over a nearby chair, one of the many stripteases that she treated him to yesterday. Pale silk bl...

Locktober

by Raklos on Sep 26, 2020
Fetish

Welcome to Locktober. A month of denial with your privates locked away and inaccessible. This game adds a bit of spice to the experience by teasing you a little every day, under the watchful eye of a cruel but fair dominant. Remember: read just one chapter a day and don't clear your internet cookies this month. Start Game Mode and begin your adventure in fru...

Open in Reader

My Wife-His Toy Ch. 01

by wifetoy on Sep 12, 2017
BDSM

The office was quiet as I worked late to finish a project. After all there was no reason to go home to the empty house. Bzzzzzzzt, "Shit" I cried as the jolt of electricity suddenly coursed through the composite fiber chastity device that had imprisoned my touch starved cock for the past six months. This was the master's cruel signal to check the secret em...

Letter from Hartford

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: Miguel awaits me, as he and his assistants prepare the cocaine with baking soda. Mig gives orders mostly, and the fellows chop and mix the drugs, and suddenly, there I am in my snug little Hello Kitty top and cargo pants. I've been out shopping with Miguel's Platinum Visa, and I grin at him loopily. "Remy, honey how are you?" Mig smil...

Howie Hangs

by justincbenedict on Aug 7, 2019
BDSM

Giulia ran her long dark nails up and down Howie's swelling cock. He was hanging just above the floor with his hands tied to the rafters of the barn. Giulia and Howie loved going up to his parent's country place. Howie's folks summered in Miami now, and so the farm was deserted. Giulia shook her thick ash blonde hair and re-adjusted her sunglasses. She to...

Destroyed by text. Pt. 06

by Need_to_serve on May 12, 2020
BDSM

Saturday: Walter 2:12am: 'Hi John. You don't know me, but Goddess Pam instructed me to text you. If you don't respond within 5 minutes to my texts, I have to report you to Goddess Pam. Regards, Walter.' John 2:16am: 'Hi Walter. I've responded. Now can I go back to sleep? Pam's got me working 8/8 shifts every single day, so I really need to get some sleep....

Transgender Avis's Incredible Power

by justincbenedict on Jul 4, 2018
Transsexuals & Crossdressers

Skokie, Illinois, 2009 Aiken Aycock was sad to be losing her brother Aiden to the operation. He was a great guy, but he gave Aiken the beatings and torture she needed. But he'd finally gotten the money to do the big change. Aiken had really enjoyed supporting Aiden, letting him live in her apartment...stripping naked when she got home, and taking a few fro...

The Dominatrix Order Pt. 03 Ch. 03 - Findom

by Jwwsmith on Mar 11, 2019
BDSM

One evening later that week, Isabella called upon Plaything and many of the other servants and slaves to clean the halls of her castle. Isabella wore her sheer silk black robe, the front of which she left open, revealing her lavender lace push up bra and matching G-string panties. Daniel thought it incredibly cruel of her to wear such revealing lingerie in f...

Creating a Monster

by justincbenedict on Sep 19, 2017
BDSM

2006 I wait on my knees, with the steel chastity tube locked between my legs, for Bootsie's return. How will she come back? Freshly fucked or with semen residue on her glossed lips? Have I made a mistake by relinquishing all control of my marriage? 2003 "Oh Silas, honey. That's the cutest thing I've ever seen!" Bootsie's enthusiasm was bubbly as she lock...