Roommate Cuckold Stories

20,909 results
Orientation
Length
Source
Infinite Scroll

Bruce

by captivate on Sep 2, 2017
First Time

The year was 1972. It was the sexual revolution all over America. On college campuses, sex was everywhere. There was no fear of disease because anything could be cured with a painful shot and a supply of antibiotics. People passed each other, eyes met, and they went home together. Jane's housemates were no different. A few had steady boyfriends, but mostly...

Jack & Jill Party

by Sunlover on Aug 31, 2017
Group Sex

I had no idea what might come of the ad I placed in the Yahoo personals seeking participants in a jack and jill party for the region I lived in. I was also a little concerned about whether people could indeed restrain themselves and simply keep the meeting to a masturbation activity. For those of you who are not familiar with a jack and jill party, it simply...

Four Friends in a Parking Lot

by SilverCatEyes on Sep 1, 2017
Humor & Satire

After work one day Brandon, Chuck, Quinton, and myself were talking in the parking lot sharing stories of sex gone wrong. Everyone agrees that they should be shared and perhaps warp the readers as bad as it did them. But, since I wasn't there, I can't really stretch them into full blown stories. Just pass along what I "lucky" enough to hear. I swear to you e...

Little Sister Ch. 11

by Da_Vida on Sep 16, 2017
Transsexuals & Crossdressers

When Ralph and Jean arrived at Denise's condo Jean retrieved a key from his purse and opened the door. Denise came out of her bedroom in her pajamas where she apparently had been sleeping. Denise placed her hand in front of her mouth and yawned as she walked toward Ralph and Jean. Denise came up to Ralph and took hold of his upper left arm with her right han...

The Healthclub

by wfm1969 on Aug 31, 2017
Group Sex

I met Lisa at the health club. For weeks we kept bumping into each other during our workouts. We'd make small talk about nothing for a couple of minutes, but would go our separate ways. She was cute with an engaging smile and bright green eyes that lit up. I was secretly captivated by her and would plan my workouts around the time I expected to see her. One...

How I Became Vanessa Ch. 03

by vanessa_brown on Aug 30, 2017
Transsexuals & Crossdressers

Hello dear readers, I strongly encourage you to read the previous two chapters of this story to fully grasp the sudden changes which affected my life. * At home, Elena was waiting for me but she wasn't alone, her boyfriend was there too. He was a tall black guy named Jeff. I told them all the things that happened at July's, blushing as Jeff was watching m...

Bad Romance: Move Along

by Samuelx on Sep 12, 2017
Non-Erotic

Step one, I exit Loblaws, where I just spent the past eight hours. Working the eleven to seven overnight shift isn't easy. I yawn as I exit the store, my dark security uniform getting wet fast as it starts to rain. Wonderful. It was dry all night and as I head home, it starts to rain. That's just the kind of luck I've got, ladies and gentlemen. I walk out of...

Caden's Adventure

by DaddysBadLilGirl on Aug 18, 2017
Fetish

Courtney ran down the hall, late again, to class. She stopped outside of the door and quickly smoothed her white button down shirt, red and brown plaid skirt and her left knee sock. She hated the uniform, but it was required for the private college. Unfortunately, she had grown after her parents bought her uniform for this year and the skirt was a bit shor...

Living Life with Faith Ch. 01

by triplehigh on Sep 14, 2017
First Time

All characters are over 18. This is my first submission, so feedback of any kind would be greatly appreciated. CHAPTER 1 It was cold again, the temperature couldn't decide whether it wanted to be frigid or warm. Today was especially frigid. It was 8 am and Reece was out running as he normally did every other day, breath leaving his mouth in billowy wisps....

Dormroom Performance

by davion2308 on Sep 13, 2017
Erotic Couplings

*Please, please, please give me feedback on the story. Tell me why it worked and what you would have rather seen. Why do I suck at writing? Why am I good. Thanks and enjoy! * Dana stumbled into her darkened dorm room. It was well past 1:00 a.m., late Saturday night. Melissa, Dana's roommate, was a large pile of covers on the bottom bunk. Melissa's boyfrien...