Cruel Mistress Stories

42,761 results
Orientation
Length
Source
Infinite Scroll

Bi The Lake

by desirea69er on Sep 1, 2017
Group Sex

Jessie was sitting out by the lake just relaxing catching some rays, boats and water skiers going by occasionally. Gavin watches from the distance knowing he brought his wife here to be seduced by his mistress. Jody approaches the dock where his mistress awaits. She has her own plans of seduction. She reaches with her hands upon Jessie’s shoulders introduci...

A Day for Firsts

by kinkroulette on Sep 14, 2017
First Time

The day had finally arrived, the day that I had been looking forward to for so long. Today... was the day I was going to lose my virginity! And, as the ache in my dick reminded me, it was the day my Mistress would free me from this cage. It had been a month since the unmarked box had appeared on my doorstep, a gift from my partner (and Mistress!) Elise for...

A Gift for His Mistress

by justboycrazy on Sep 1, 2017
Group Sex

Mike came home from work with a gift for his mistress. The gift was a tall, blonde hunk named Nick. Once Mike and Nick arrived at his house, Mike was excited about seeing the look on Jana's face. Jana came down the stairs and saw Mike and her gift. Mike said, "Nick, this is Jana, my mistress." She said, "Hi, Nick. Mike, he's really cute." Jana got a look...

White Slaves of Eban Ch. 06

by Karenkay on Aug 30, 2017
Interracial Love

Katie nervously entered the lounge shutting the door behind her. She stood with her hands toward her back leaning against a wall as she closed her eyes and began to sob. How could she do this so easily? She acted like a total slut out there for that man! That's what she was trained to do wasn't it? She opened her eyes and walked over to the sinks and start...

First Time with Jessica

by magicrub on Sep 16, 2017
Transsexuals & Crossdressers

"Hello Darling, I'm Jessica." "Hi, Nice to meet you, I'm Rob." "Can I offer you a drink?" asked Jessica, noticing he was pretty nervous. "Sure, that would be great," he responded as he watched her cute ass sway into the kitchen. They made small talk for a while than her congenial tone changed. "Well, let's get to it. You ready to become my little slut b...

Strip ...

by seekingsusie on Sep 16, 2017
Transsexuals & Crossdressers

"Strip. Get off all those ugly man clothes. Now." I looked around, saw the bathroom and started toward it and heard her stomp her feet. I looked back and saw her grimly shaking her head and pointing to the floor near her left foot. I stood in the designated spot and the look on her face was grimmer yet. She moved her hand slightly, indicating DOWN. I kneel...

Pleasurably Agony

by Enigma_Fetishist on Jan 28, 2020
Fetish

Names, places and events are fictional. *** The Bull leans leisurely back in his chair. His legs stretched over the side of the chair. "Hmmm love seeing a professional at work." He growls approvingly. "Hmm just doing what brings me pleasure." She laughs as the Vixen struts back to him. Her long legs encased in thighhigh boots, shreds of what were a pair...

A Sissy Fantasy

by Sissy_Jeanette on Mar 30, 2020
Transgender & Crossdressers

My darkest fantasy has come true. I'm now a slave to a dominant couple. My ex-wife and her new boyfriend have taken me in, and in return I am dressed as a girl always and their maid and sex slave. Frilly panties, stockings and skirts, babydoll t-shirts, and a blonde wig are parts of my new uniform. Also I now wear a stainless steel chastity cage now encasing...

The Boyfriend

by hydrangealawrence on Oct 21, 2019
Transgender & Crossdressers

I sit on the bed, anxiously waiting for Miles to come out of the bathroom. I'm wearing the leather corset and knee-high boots he asked for. We've been dating for about eight months, and he recently told me there was something special he wanted to do in bed. I'm always open to trying new things, and I really like him. But his refusal to tell me what exactly...

Aaralon's Discoveries

by Sixth on Apr 18, 2002
Fantasy

Aaralon was nervous; he was not only disobeying conventional wisdom by attempting a summons but he was flaunting the strict rules of the boarding school by doing so. He was twenty years old and had been in College of Light Shadow for the last fifteen of them, he couldn't really remember what his parents looked like and all that really seemed to matter about...

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