Roommate Cuckold Stories

20,909 results
Orientation
Length
Source
Infinite Scroll

Becoming a College Cuckold Ch. 01

by notreallife13 on Aug 8, 2018
Erotic Couplings

My sophomore year of college was the beginning of major changes in my life, and it's crazy to think about how things spiraled out of control as fast as they did. My name is John and I go to a university in Miami. I had a successful first year in the dorms but they tend to be more expensive than living off campus, and while I wasn't much for parties, I was ex...

The Anklet Contract

by Joncarver on Jan 28, 2020
Loving Wives

My dear, We have discussed this before and I wanted to present to you a contractual agreement between you and I that specifies some rules between us. As you know I enjoy the cuckold lifestyle and enjoy some of the games we play. This contract will take it further to give you more control to empower you to embrace your own inner slut and inner strength. You...

Kim's Journey Ch. 06

by lilyandstoney on Sep 19, 2017
Exhibitionist & Voyeur

With the advent of the internet, I read about many people who think cuckoldry is a relatively new phenomenon. They are very mistaken. As an eighteen‐year‐old college student, I had no idea what cuckoldry was and if someone had tried to explain it to me, I would have never believed them. My summer experiences with both Mark and Corey and with Maurice and Gail...

How Blondie Became a Hotwife

by raven2018 on May 4, 2020
Loving Wives

#1 in the new Blondie Saga Beautiful young Southern wife eagerly agrees to cuckold her voyeur husband The Blondie series of stories are taken from actual events that transpired much as depicted. The main characters are based on real persons and their behaviors are generally authentic. Their dialogue has been reconstructed from a fully fallible memory, yet...

Cuckold For My Wife & Her Sis Ch. 01

by Anal Slave on Sep 14, 2017
Fetish

This story is how I met my wife Susan and how Susan and her sister fucked me and abused me. It all started back when I was eighteen I had two women that lived next door to me and they loved to fuck and suck all the men around the neighborhood. I remember the first time I watched the oldest one Susan, give her boyfriend a blow job out by the pool. She had hi...

I Make Believe I'm a Cuckold Ch. 03

by donaldelliott11 on Feb 3, 2020
Transgender & Crossdressers

This is the third chapter of "I Make Believe I'm a Cuckold." You should read those first. [Writers love feedback. Please comment on and rate this story. About 99 readers out of 100 do *NOT* bother to do either. Comments help me improve my writing; ratings help other readers find what they will most enjoy reading.] +++++++++++++++++ Wednesday morning afte...

Does she cheat?

by hottiemorgan on Feb 17, 2015
Cheating Spouses

Morgan sighed, "her we go again", she thought as she watched two men push he boyfriend. Naturally, her boyfriend's buddy Bill had gotten them in trouble. Bill was always too loud, and too obnoxious, and tonight he had hit on one of these guys girlfriends as the bar closed. She watched as her boyfriend began to push back, acting with whatever bravad...

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Brad's Return Ch. 01

by grizzley123 on Sep 29, 2020
Loving Wives

Brad's Return, Chapter 1 ****************************************************** This is a continuation of the "Brad's Suggestion" stories I wrote a while back. It has similar cuckold and bisexuality themes, along with some lesbian and light BDSM fun thrown in. It emerged from my never-ending desire to put off the real work I should be doing. I hope you enj...

Cuckold Email

by lbenton on Dec 2, 2019
Loving Wives

Author's note I would like to thank Andrew John for all the time he spent editing this story. He did a fabulous job correcting my spelling and making a so, so piece of literature into a real story. thank you, Andrew John. *** Cuckold email Chapter one: The bar I am driving my pickup on the way home from downtown Albuquerque. My beautiful wife of over fi...

Limits

by The Style Guy on Apr 14, 2020
Loving Wives

Author's Notes: Recently, TheMarlboroMan, one of my favorite authors, has introduced right-wing politics into his stories. The overall political bent got me thinking about stereotypes and how they might play out within the cuckold lifestyle. As I outlined this story, Chris, a Trump supporter and Rush Limbaugh fan and his business partner Ben, a long time B...