Cuckold Island Stories

24,566 results
Orientation
Length
Source
Infinite Scroll

Jackie Begins her Transition

by Sissy_Sammi_ on Feb 7, 2018
Transsexuals & Crossdressers

All characters are 18+ Also this is the 2nd part to this story. Reading the first, "Taking Mom's Place," makes it much more understandable and enjoyable. ***** After that second day with Martin, Jackie began to settle into her new rhythm. She began her actual transition, beginning to take testosterone suppressors and estrogen supplements, growing out her...

Cheating and Cleaning

by fallstaffer on Dec 21, 2017
BDSM

What should I have done after fifteen years and five kids? I ask because I really don't know. Should I have waited another fifteen years? What do you do when you tell your husband, "I want to be controlled. I want to be degraded and humiliated." I begged him to go out into the world and cheat on me. "Come back and tell me she was so much better than I am. Ma...

Medusa's Trophy

by SueDNimm on Apr 3, 2019
Sci-Fi & Fantasy

Author's forward: In Greek mythology and in almost all its modern manifestations, Medusa is a straight-up monster. This story portrays a different perspective. I hope you enjoy it. All characters are over 18 (especially Medusa) **** The slave winced as he stumbled along the stony gorge, following his master. After a fortnight trekking over this misty, bar...

A Stormy Night Pt. 01

by TruLuv26 on Jul 31, 2019
Romance

A/N: This story contains special fonts such as italics. Every person in it is eighteen and above. Lightning illuminates my curtains, swiftly followed by a deafening rumble of thunder. Raindrops hammer down on the house, as if attempting to penetrate through just to get to me, and I hug the blanket tighter around my body. What a great way to end my eightee...

A Pair of Au Pair Ch. 02

by BookWurm on Sep 17, 2017
Group Sex

If you haven't read Chapter 1 then you might wish to read it before continuing. It's just a suggestion. If you're more into the erotica, you didn't miss much, however if you crave more background of the characters you may wish to check it out. So here I was sitting poolside watching the two young French girls frolicking in the pool. Both Sophie and her fri...

Katie's Interracial Experience

by wakedad8 on Sep 12, 2017
Interracial Love

My wife and I have been married for 20 years and we are both in our mid 40's. Katie still looks quite hot even after having 2 kids. She is 5'-1", about 120 pounds, full B cup boobs, dark hair and eyes and is quite curvy. She is aging nicely with all the little lines, creases and sags in all the right places. I think it really gives her that COUGAR look. I...

The Last Sister

by blackmerida on Sep 12, 2017
Interracial Love

The Westervelt family sat around the dinner table quietly eating a Thanksgiving meal prepared by their mother. Jeannette, the oldest, sat beside her husband DeRay. Gillian, beside her boyfriend, Andre. Georgina, next to her boyfriend, Jalen. Finally, the youngest daughter, Laura, sat by her father whose head was face pointed straight down into his white mash...

First Day in the Caribbean 22

by Ennis Piceo on Sep 19, 2017
Erotic Couplings

"It has been a pretty good day, on the whole," Charlie thought to himself as he biked home. He hefted his rucksack and thought about the memory chip in the camera. He had been tempted to leave his bike at the bike shop with Jenny's just for the romance of it, but he was eager to get home and look at his photos with artistic and lascivious intent. He not only...

Life: It Only Gets Better Pt. 01

by Shadowforce1 on Sep 12, 2017
Interracial Love

As usual, my stories have women with bigger than average chest sizes. Also they have Interracial content. If this is not your thing, you have been warned. (Yes I know, it is in the interracial section but there are many people that still read and get angry that it is interracial in nature.) To see what the women look like see my profile. ***** The rhythmi...

Quetzalcoatl Ch. 04

by DetectiveSpecialist on Sep 26, 2017
Sci-Fi & Fantasy

4 I awoke to my mother banging around in the kitchen. "What's going on?" I asked still half asleep. "The wind is starting to pick up. I'll make some coffee. Maybe you should get up top." I found my clothes, got dressed and got out of bed. I had to squeeze past my mom in the small galley and it felt wonderful as our bodies pressed against each other. I he...