Cruel Mistress Stories

42,761 results
Orientation
Length
Source
Infinite Scroll

The Slave and the Sissy

by Sputnik57 on Sep 12, 2017
Transsexuals & Crossdressers

She had always been very rough with him, the big woman, but this morning was exceptional, and different. She had come home late from her usual soiree with other local mistresses and had whipped him mercilessly for no apparent reason; she had woken him during the early hours several times, tormented him and had her arse licked while she applied her dildo or h...

Madame F Pt. 01

by Delirious_Capitulation on Dec 2, 2019
BDSM

There was no going back. Well, I suppose, looking back, that I could just have said 'No, I've changed my mind', and left. But at the time, it seemed inevitable. There we were, the three of us, giggling, nervous, blushing, looking at the others and alternately thinking 'what a slut!' and 'god her tits are lovely -- I wonder if mine are good enough?' Each o...

stef's Slavery Ch. 01

by hisemerald on Sep 17, 2017
BDSM

stefaan took a deep breath as he stood to de-plane. Valerie had been his Mistress for about 2 years, though they had known each other for three. She was everything to him and so he left his own country to stay with Her for the next 2 years. She had taught him as well as possible, taking over his life as best She could with an ocean separating them. This was...

Mistress Milks Me

by RobinTVDaniels on Sep 15, 2017
BDSM

It was a bright sunny spring day and I had gotten up early and made my self as sissy as possible for my mistress. I touched up my shaved body to make sure not a hair was anywhere on me. I gave myself two enemas to make sure my ass was clean in case my mistress might want to use me in some way. (I always hope for the best lol) I had put on my sexiest panties...

The Auction Pt. 01

by phoenixcinders on Jun 5, 2019
Transgender & Crossdressers

Sorry I haven't posted in a while. I fell into a slump, but I'm back with a brand new story. All characters involved in sex are 18 or older. This story contains feminization, slavery, anal sex, transgender, sissy, blow job, cum swallowing and vampires. You have been warned. If you don't like the tags, don't read it and move on. Other than that, feel free to...

Cheryl's Passion Ch. 06

by Schlank on Sep 25, 2017
BDSM

The next time I woke up it was 6:59 a.m. I was lying naked in bed, and there was still a stainless-steel shackle locked tightly on my ankle. April and her mother were both standing above me, wearing identical bathrobes. "So, what did you think of my slave?" April asked her mother. "She was incredible," her mother replied, smiling, "Thanks for sharing her w...

Slim Girl to Fat Bitch Ch. 04

by robin35 on Sep 16, 2017
Fetish

Gladys led Bev up the stairs and asked for a tour of the upstairs. Bev was happy to show her the house. It was something that she was proud of. She had worked hard on the house over the years and it was considered to be the home that she built. She gave Gladys a quick tour and then Gladys said. "Which is the Master Suite?" Bev led her down the corridor to...

Freedom and the Widow Ch. 12

by Sputnik57 on Sep 14, 2017
BDSM

Dominique brutally dominated and humiliated the hapless wretch in many ways, finishing the session by cruelly pressing the spiked heel of her stilettos into his balls till he begged her for mercy, then having her two assistants bind and gag him, leaving him like a carcass at butchery in the middle of the stage. Sated for a while, she left to join her guests...

At Her Disposal Ch. 06

by Sputnik57 on Sep 14, 2017
BDSM

The mule was flanked by the two victorious horsewomen, and the hanged male's journey to meet his purchaser began, his cock erect and rubbing at the silken bondage with the movement of the mule as he squirmed, his anus tingling at his divine sense of helplessness as it clenched and dilated on the stimulating plug as the two women whipped mule and enslaved ars...

Frustration Pt. 03

by kalkstein1970 on Sep 25, 2017
BDSM

The rest of that evening passed in a haze of sexual torment and sweet agony of submission, teasing, and denial. You stripped out of your evening dress to reveal a skimpy little black thong and matching black mesh half-cup bra - your outfit for the rest of that evening, one that drove me mad with lust, watching helplessly as you paraded your long legs, tight...