Cruel Mistress Stories

42,761 results
Orientation
Length
Source
Infinite Scroll

The Taking of Rebecca Ch. 03

by Helenveronica on Sep 19, 2017
Transsexuals & Crossdressers

Rebecca, has been taken three times in the ass over the last couple of hours and finds the butt plug to be a little uncomfortable. She wonders why are they keeping her plugged. She thinks to herself, the obvious reason is that they don't want her leaking, but to what end? She can't help wondering if there is another deeper or darker reason. Perhaps they wi...

Hooker

by oneiria on Sep 14, 2017
Erotic Horror

The Right Reverend Jimmy John Tanger smiled as he rolled down the passenger side window of his Escalade, and his eyes twinkled beneath the dark shades he wore in even the blackest of nights. The whore walked over to his car and leaned over to peer in. She was everything he had ever dreamed of and more. Her long, silky scarlet hair spilled over her breasts,...

The Journey Pt. 05

by MissYellowPanties on Nov 25, 2017
Transsexuals & Crossdressers

Job Interview I received more special commissions, perhaps the strangest for me was Head Mistress Kendra, who had me in her office dressed as a school girl, she could have had everything she took and willingly, for free in my bedroom, but she needed it to be in her office. Afterwards she told me how she had wanted me the first time I bent my bare ass over...

A Taste of Midnight

by Corpse_rider on Sep 16, 2017
Erotic Horror

As she stepped into the dark corridor leaving the cold night air behind her, Katy suddenly felt woozy, the effects of alcohol from the club catching up with her. 'You okay, luv?' her companion behind said with concern. Katy heard the front door close behind her, deepening the gloom in the corridor. She felt a frisson of apprehension but it was gone in an i...

Trip to the Playa Ch. 02

by Holly2 on Sep 17, 2017
BDSM

The next morning you wake to find me missing from the tent, with a note of some sort folded up lying on the top of my sleeping bag. You unfold the note – it’s a hand drawn map, with a short message scribbled on the bottom: “Meet me here at 10am.” Your penis hardens, as if in anticipation. You lie back down and begin slowly stroking it, thinking of how you en...

Beware of the Babysitter

by poboy789 on Sep 12, 2017
BDSM

This is my first attempt at writing something like this. Please let me know if it is liked and worth continuing. * Wednesday It had been a pleasant evening. The summer was winding down. My wife, Kate, and I had been at a party at a friend's home. We were returning home. I looked at Kate as we pulled into the driveway. What a remarkable woman. We had been...

A Reunion Ch. 03

by Syana on Sep 16, 2017
BDSM

She was humming to herself as she made her way downstairs. Reaching the living room, she saw that Jason was on the computer. She held back a chuckle when she noticed that he could barely concentrate on what he was reading. "Getting some good information there, hon?" she asked, startling him. She was standing behind him, her hands on his shoulders. "Uh, yea...

Louise Gets Shared

by LouLouRayne on Sep 17, 2017
BDSM

Louise stretches out in her double bed. She so enjoys lazy Sundays. She puts on her dressing gown and heads downstairs. But Sam's nowhere to be seen. So she puts the kettle on, reminiscing about Sam's hard cock filling her earlier that morning. Her mind wanders as the pressure in her pussy slowly builds. Her hands slide down to her breasts, caressing them so...

My Sister My Mistress Ch. 04

by debashritaslaveoftabassum on Feb 12, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** Please comment whether you like it or not as that is the only way I can know. *** I understood what she wanted me to do, but I really didn't know what I would offer her as a tribute. It did seem a little silly, but I knew that she was serious about the whole thing so I figured I...

Coast to Coast Pt. 04

by Phileas123 on Jul 6, 2020
Fetish

I immediately felt the pressure leaving my body, and as soon as I managed to get rid of the restraints, I rushed to the bathroom to do my thing, leaving Stephanie behind. Being free after all those hours was beautiful and I could relax myself. "Monica." She called as I flushed the toilet. "Yes?" "Could you please help me?" I was taken aback by the reque...