Roommate Cuckold Stories

20,909 results
Orientation
Length
Source
Infinite Scroll

Alison's Younger Man

by LiChelle on Sep 12, 2017
Mature

“Mr. Thompson? Are you home? Hello? Mr. Thompson, it’s Alison Campbell. Hello?” Alison Campbell, real estate agent to the extraordinary, lifetime member of the Million Dollar Club, let herself into the condo of Peter Thompson, the writer to whom she had made her latest sale. She had knocked and then used the key she had come to deliver. Not that this was co...

The Roommate Ch. 02

by Cordellia on Sep 15, 2017
Transsexuals & Crossdressers

I woke up on the couch in the middle of the night, about 1am. My head ached. My back was even worse. On the coffee table lay a tipped wine glass, stained red, alongside four empty bottles of pinot noir. My chest felt tight. I reached up and felt the strap of a bra. What? The activities of the night before came flashing back. The dressing up. The make-up. T...

Franchise Ch. 02

by Sylvan on Sep 12, 2017
Group Sex

As time went on, Phil spent more time with Lisa and Kaori, and they spent less time with their usual friends. Phil was immediately more popular, but still didn’t hang out with Lisa’s crowd, since he was already getting all he wanted from them–the love of their women. This development didn’t sit well with some of Phil’s friends. Namely Caitlin. They were si...

Sally's First Black

by twistedgraygoat on Sep 25, 2017
Interracial Love

First let me introduce myself to you. I am Sally and I am white. Last fall I passed my 30th year and I don't think I have fully experienced life to this point. I am not a virgin and am sexually active when I want to be. In fact, I love sex. I have never been married but have had several really deep and meaningful relationships. I have a body which I see as d...

College Hi-Jinx Ch. 04

by BrettJ on Sep 15, 2017
Novels and Novellas

Chapter 4: Taking On All Cummers Lindsay licked her sister's pussy until it was almost raw and sensitive. The rest of the curvy brunette's body had been paid equal attention, she hadn't enjoyed this many orgasms in a long, long time. "So, have I thanked you enough for sending me to Madeline? Lindsay giggled, finally coming up for air. "Uh-huh!" Sonia gasp...

Fair Play

by AmysNewFreedom on Sep 13, 2017
Erotic Couplings

Standing in the pale moonlight cast from the four open windows in the middle of my bedroom, my skin shines alabaster, taking on an unearthly shimmer as I slowly turn in front of the mirror. Flaws hidden in the soft glow, the curves accentuated by the gentle light, my eyes roam everywhere over the vision in the mirror. Taking in the line of my jaw as it sweep...

One Fine Orgy

by mysteriouswoman on Sep 19, 2017
Group Sex

I had heard stories but had not believed them to be true. Yet what was happening before my very eyes was indeed true, and astonishing. This frat party had developed into a full fledged sex orgy. I was 19 and a student at a prominent university in New Orleans. My roomies and suite mates had told me that sometimes, frat parties turned into fuck fests, but I...

Office Teen Ch. 02

by MrPetersPenname on Sep 19, 2017
Erotic Couplings

My next encounter with Claire was about a month later. She had turned 19 since then and I had recommended her for a full-time job as a coordinator in a different department with our company. I'm told she had backed down on her college course load to work with us full-time. To the wise elders it looked as if she might go husband hunting instead of getting a l...

Three Hippy Chicks

by Hornyman69WithU on Sep 13, 2017
Group Sex

I hitch-hiked alone to an outdoors Allman Brothers concert in Atlanta and wound up sitting next to and passing my pipe back and forth with what appeared to be three sisters, lovely young things very close in age. As Duane Allman and Dicky Betts were trading guitar licks as only they could, I could not take my eyes off these girls--classic hippy chicks weari...

American Pornstar

by fireaway on Sep 12, 2017
Interracial Love

Diary p.2: "Now I have found myself in a bizarre situation. My so-called normal life spiraled out of control in the last two months. I am writing this in hopes that one day I can make sense of all this. Tomorrow I will go in for my first shoot. I don't know how I got myself into this mess exactly but I will try my best. I feel scared and so helpless, but I c...