Cuckholding Stories

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

Post Cuckold Insecurity

by MasterfulMistress on Sep 17, 2017
Loving Wives

After My Cuckholding Introduction Wow, what a night of revelations that turned out to be. Attending our first sex club event with our swinging friends Dave and Linda was indeed an undreamed of sexual feast. I witnessed my Amy fucked with the most staggeringly big cock imaginable. To see her cunt stretched beyond the wildest of imaginations being both amazin...

The Babysitter Has A Dick

by mr.z on Feb 29, 2020
Transsexual

Ricky Sampson is your average 18 year old boy. He lives with his parents and baby brother in a house in Nevada where he goes to school and works part time at a water park, it's Nevada the town gets really hot all year round. Ricky looks like a typical computer science nerd, with his glasses, black hair and pasty white skin but he wants to be anything but a s...

Open in Reader

Pokemon Sex Arena

by Devious on Nov 18, 2018
Fan Fiction

Welcome to the world of pokemon... just not as you may know it. First, pokemon are more anthropomorphic than animal. And second, they have actually taken over the world, and you are an unfortunate victim of this fact. While most humans are allowed to live comfortable lives or kept as pets, you on the otherhand, are a slave. And your home is the arena. A plac...

Open in Reader

Kira's First Errands Ch. 02

by dan57 on Sep 17, 2017
Loving Wives

It had been six months that Dan, Tom and Kira had initiated this bizarre game of part time marriage, at Dan's whim. They had been on vacations in Florida when he made a joke telling Kira she acted as the wife of their close friend Tom. He was still a bachelor and, from time to time, she helped him for his laundry, sewing back buttons, shopping for him or occ...

The Adventures of Joe the Pirate

by Noira on Sep 14, 2017
Humor & Satire

Author's note: warning, sarcasm ahead. Do not read if you are easily offended by stories that do not take themselves, or anything else, seriously. Written with the intent of getting as many Lit categories in one story as possible. — It was a brilliant day in Brilliantville, and Joe the Pirate sprawled out on his quilt, which happened to be made of various...

Consumed Ch. 03

by NotWhatSheSeems on Sep 3, 2017
Erotic Horror

De Valmont was able to ignore the sounds coming from the bedroom very easily. Claire tended to scream during their violent sex, so her pitiful cries could be easily overlooked. The servants were very well trained. No one asked any questions or went anywhere near the Master Suite. Or perhaps they were just frightened of him. That is the thought that made hi...

Crossdresser Gets His Ch. 02

by CourtStJester on Sep 12, 2017
Transsexuals & Crossdressers

She certainly had a busy night. Between the time she came home and found her husband in her clothes and the time they woke up, she had fucked him with her 10-inch dildo four times. He was barely able to tolerate the first two times, and the third and fourth were excruciating. Sometime after that, his wife either pulled the dildo out of his ass or he expelled...

Aphrodite's Curse Ch. 015

by Gaius8666 on Sep 15, 2017
BDSM

Persephone towered over the trembling Demetrius, her dreadful and frightening beauty making him even harder than before. "What foolish man would dare to set foot in the land of the dead!" She yelled, purposely making her voice as intimidating as possible as she got off on seeing humans tremble in her presence. "What is your name!" She demanded as poor Demet...

Adult Resort - Dream Pt. 01

by hotorangecouple on May 22, 2018
Loving Wives

Trying to get back to writing stories about our life and fantasies. No comment because we all know how that goes with anonymous. ***** I had this dream the other night. Let me give you a little background. My wife is sexy. I mean just sexy. Long legs, great little ass. Beautiful. I'm NOT a boob guy, but her boobs are just amazing also. Blue eyes, beautiful...

The Trap Ch. 01

by MrDeviant on Sep 16, 2017
NonHuman

I'd been riding forever it seemed. Ten days on the road, with all the necessary stops, and I was stuck on the dullest road in the dullest state in the U.S.---Oklahoma. If boredom earned me money I'd be a fucking trillionaire by now. Flat and only broken by the occasional oil rig, I rode on working my way to my ultimate goal--my brother's house in New Mexico....